MORPHOLINE (MORFOLN)

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid makes the salt morpholinium chloride.

The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.

Morpholine appears as a colorless liquid with a fishlike odor. Flash point 100°F. Corrosive to tissue. Less dense than water and soluble in water. Vapors heavier than air. Used to make other chemicals, as a corrosion inhibitor, and in detergents. Morpholine is a saturated organic heteromonocyclic parent and a member of morpholines.

Morpholine is an important building block for rubber chemicals and finds a multitude of applications in other industries. It is used as an intermediate for water treatment, the production of pharmaceutical and agrocultural products as well as optical brightners.

Morpholine (1,4-tetrahydro-oxazine) is a simple heterocyclic compound that has great industrial importance and a wide range of applications. This chemical compound and its derivatives have been used as rubber additives, corrosion inhibitors, solvents, optical brighteners, antioxidants and in the manufacture of a range of drugs and herbicides.

PRODUCT USE

Solvent for resins, waxes, casein, dyes. Morpholine fatty acid salts are used as surface active agents and emulsifiers. Other morpholine

compounds are used as corrosion inhibitors, antioxidants, plasticisers. Morpholine compounds are also used as viscosity improvers,

insecticides, fungicides, herbicides, local anaesthetics and antiseptics. Morpholine has a volatility similar to water. It is therefore widely used

as a neutralising amine in combating carbonic acid corrosion in condensate return lines in steam boiler systems as well as in aqueous

hydraulic liquids and similar systems. Morpholine vapours protect silver and other metals against corrosion and tarnish by acid fumes such as

SO2 and H2S. Corrosion of metal aerosol containers and valves can also be prevented by the use of low levels of morpholine. Morpholine is

effective in hydraulic system fluids based on glycols, where various metals are in contact with the fluid at the same time. Morpholine

derivatives have been used as corrosion inhibitors in mineral lubricating oil, turbine oils, for protecting storage tanks, pipes and other devices

used in handling petroleum distillates, and for inhibiting the corrosive action of grease-proof paper on steel and other metals Intermediate

SYNONYMS

C4-H9-O-N, C4-H9-O-N, OCH2-CH2-NHCH2-CH2, “diethyleneimide oxide”, “diethylene imideoxide”, “diethylene oximide”, “diethylenimide

oxide”, Drewamine, “p-isoxamine, tetrahydro-“, “p-isoxamine, tetrahydro-“, 1-oxa-4-azacyclohexane, 1-oxa-4-azacyclohexane, “2H-1,

4-oxazine, tetrahydro-“, “2H-1, 4-oxazine, tetrahydro-“, “4H-1, 4-oxazine, tetrahydro-“, “4H-1, 4-oxazine, tetrahydro-“, “tetrahydro-1,

4-isoxazine”, “tetrahydro-1, 4-isoxazine”, tetrahydro-p-oxazine, tetrahydro-p-oxazine, “tetrahydro-2H-1, 4-oxazine”, “tetrahydro-2H-1,

4-oxazine”, “BASF 238”

CAS Number: 110-91-8;EINECS 263-172-8; IUPAC name: Morpholine. Other names:Diethylenimide oxide; 1,4-Oxazinane; Tetrahydro-1,4-oxazine; Diethylene imidoxide; Diethylene oximide; Tetrahydro-p-oxazine

Synonyms & Trade Names: Diethylene imidoxide, Diethylene oximide, Tetrahydro-1,4-oxazine, Tetrahydro-p-oxazine

Chemical formula: C4H9NO

Molar mass: 87.122 g·mol−1

Appearance :Colorless liquid

Odor: Weak ammonia-like or fish-like

Density: 1.007 g/cm3

Melting point: −5 °C (23 °F; 268 K)

Boiling point: 129 °C (264 °F; 402 K)

Solubility in water: miscible

Vapor pressure: 6 mmHg (20 °C)

Acidity (pKa):8.36 (of conjugate acid)

Magnetic susceptibility (χ): -55.0·10−6 cm3/mol

Main hazards: Flammable, Corrosive

Odor: characteristic

Use: Due to morpholine’s chemical stability and similar volatility to water, it makes an excellent corrosion inhibitor for steam boilers and water treatment systems. Morpholine is also used as a common emulsifier used in fruit waxes to protect against fungal and insect contamination. Morpholine can be used as a pH modifier for fossil and nuclear fuels, in rubber accelerants, as a descaling agent, antiseptic, textile printing and dyeing agent, antioxidant, deodorizer, and in medicines and pesticides.

Applications:Corrosion inhibitor in steam condensate ( Boiler), Optical brighteners, pharmaceuticals.

Morpholine is an organic chemical compound, which is used as a corrosion inhibitor, additive and used to synthesize other chemicals. The molecular formula of Morpholine is C4H9NO. Morpholine is a heterocyclic chemical compound, which has amine and ether functional groups. Morpholine is a base due to the presence of the amine. Morpholine is colorless and free of suspended matter. Morpholine is commonly used as a solvent in organic synthesis, reactions and chemical industry research due to its low cost and polarity.

APPLICATIONS

1. ADDITIVES AND CATALYSTS

Morpholine is used as an additive for adjusting pH in nuclear power plant steam systems and fossil fuels. Morpholine is also used for corrosion protection of boiler water stream systems in chemical plants. Morpholine is used for the preparation of alumina catalysts. They are prepared in the form of a gelling agent for the treatment of hydrocarbons.

2. ORGANIC SYNTHESIS

Morpholine is commonly used for the synthesis of enamines. It is an important ingredient to produce linezolid, which is an antibiotic used for treating infections caused by gram-positive bacteria. It is also used in gefitinib, a cancer drug. Morpholine is also used in the analgesic dextromoramide. Morpholine salts such as morpholine hydrochloride are used for the organic synthesis of intermediates.

3. AGRICULTURE

Morpholine in the form of a chemical emulsifier is used for the protection of fruits. This is achieved through the process of waxing, where a wax layer is applied onto the fruits. This coating protects fruits from insects and fungal infestation. Ergosterol biosynthesis inhibitors are the derivatives of morpholine, which are used as fungicides in cereals. Some of the morpholine based fungicides used on cereal crops are amorolfine, fenpropimorph and tridemorph.

4. RUBBER INDUSTRY

Morpholine is widely used as an intermediate in the rubber industry to produce rubber vulcanization accelerators such as DTOS, MDS and NOBS. Over 50% of the demand for morpholine is from rubber vulcanization accelerators, and about 30% of rubber vulcanization accelerators are used for NOBS.

5. METAL CORROSION INHIBITORS

Morpholine is used as a corrosion inhibitor for metals such as copper, iron, lead, zinc and other metals. It is widely used in areas such as automobiles, mechanical instruments and medical equipment. Morpholine in its gas-liquid state has lower toxicity towards the environment when compared to its forerunners like cyclohexylamine and dicyclohexylamine nitrite.

6. MANUFACTURING

Morpholine is used in the manufacture of paper, glass, soap, detergent, dye and synthetic fibre. It is used to manufacture analysis reagents for nitrogen determination. Morpholine also finds applications in pharmaceuticals, tanning, textiles, household care and ceramics industries.

SCOPE

In recent times, drug discovery efforts have unveiled numerous interesting morpholine based compounds. There is still a lot to be explored when it comes to the synthesis of drugs and intermediates. With the advancement in technology, morpholine will find more applications in various industries.

Uses

Industrial applications: Morpholine is a common additive, in parts per million concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH-adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants.

Morpholine decomposes reasonably slowly in the absence of oxygen at the high temperatures and pressures in these steam systems.

Organic synthesis

Morpholine undergoes most chemical reactions typical for other secondary amines, though the presence of the ether oxygen withdraws electron density from the nitrogen, rendering it less nucleophilic (and less basic) than structurally similar secondary amines such as piperidine. For this reason, it forms a stable chloramine.

It is commonly used to generate enamines.

Morpholine is widely used in organic synthesis. For example, it is a building block in the preparation of the antibiotic linezolid, the anticancer agent gefitinib (Iressa) and the analgesic dextromoramide.

In research and in industry, the low cost and polarity of morpholine lead to its common use as a solvent for chemical reactions.

Agriculture

As a fruit coating

Morpholine is used as a chemical emulsifier in the process of waxing fruit. Naturally, fruits make waxes to protect against insects and fungal contamination, but this can be lost as the fruit is cleaned. A small amount of new wax is applied to replace it. Morpholine is used as an emulsifier and solubility aid for shellac, which is used as a wax for fruit coating. The European Union has forbidden the use of morpholine in fruit coating.

As a component in fungicides

Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.

Description

This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.

Kingdom: Organic compounds

Super Class: Organoheterocyclic compounds

Class: Oxazinanes

Sub Class: Morpholines

Direct Parent: Morpholines

Alternative Parents: Oxacyclic compounds / Dialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives

Substituents: Aliphatic heteromonocyclic compound / Amine / Azacycle / Dialkyl ether / Ether / Hydrocarbon derivative / Morpholine / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound

Molecular Framework: Aliphatic heteromonocyclic compounds

External Descriptors: morpholines, saturated organic heteromonocyclic parent (CHEBI:34856)

Morpholine is a pale hygroscopic liquid with the chemical formula of O(CH2CH2)2NH free of foreign matter. It bears its characteristic amine odour that is detectable above 0.1 ppm concentration in boiler feed. It is a widely used neutralizing amine in combating carbonic acid corrosion in condensate return lines of steam boiler systems. It volatilizes and condenses with the steam from the boilers, thereby affording protection to the lines, which otherwise would be subjected to corrosion from the carbonic acid present in the steam condensate. Its vapours protect silver and other metals against corrosion and tarnishing by acrid fumes, such as sulphur dioxide and hydrogen sulfide.

Morpholine is used as a boiler water treatment additive in steam systems of power plants and refineries. It forms an even wax like coating as morpholine oleate. It prevents decomposition of a chlorinated hydrocarbon in a composition containing the chlorinated hydrocarbon and a large amount of water. It is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile boiler water treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly in the absence of oxygen at the high temperatures and pressures in these steam systems. Because of its volatility being the same as water, upon addition to water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH-adjusting qualities become more distributed throughout the steam plant to provide corrosion protection.

Key Features & Benefits of Morpholine:

Prevents corrosion due to stress cracking

Reduces blow down requirement

Compatible with other boiler water treatment chemicals

Returns to the feed line with the condensate return so raises the feed water pH

Corrosion of metal aerosol containers and valves can be prevented by use of low levels of morpholine. It increases the pH of boiler water to protect boiler against corrosion. Due to its amine based formulation, it does not add salt to the boiler and hence does not contribute to the TDS, which results in reduced blow down and fuel savings. Morpholine can be used in all types, size and pressure of boilers.

ATAMAN KIMYA provides high quality Morpholine for boiler water treatment globally.

www.atamankimya.com

Morpholine, an organic compound with both amine and ether groups, obtained by dehydrating diethanolamine with sulphuric acid. Morpholine can be adapted to many different activities for many important applications. Some of its different adaptation can be seen in following applications like it functions as an intermediate in the production of rubber chemicals even as optical brighteners. It acts as an effective corrosion inhibitor in steam boiler systems. Morpholines can utilized as pharma chemicals and antioxidants for lubricating oils.

Morpholines can be used as emulsifiers in waxes and polishes processing industries.

Morpholine is a very good pH adjuster which is very effective for nuclear power plants. One more reason for it to be used is because of its rate of vapourization which is quiet similar to water; so what happens is when it is added to water, it disperses accordingly in water in both of its liquid and vapour phases. It can also be used as an ingredient in fungicides and bactericides.

Key Features and Benefits

Prevents stress cracking corrosion

Reduces blow down requirement

Returns to the feed line with the condensate return so raises the feed water pH

Saves power & downtime

Compatible with other treatment chemicals

Versatile applications

Physicochemical Data

Properties: Typical Value

Form: Clear liquid

Appearance:Colourless

Odour:Amine like

Assay as Morpholine:99.0% min.

Solubility: Completely soluble with water

Application Areas

Rubber Chemicals:Delayed action accelator

Catalysts:Temperature sensitive polymerization inhibitor

Gelling agent

Optical Brighteners

Stabler than chlorine bleaches

Pharma Chemicals: Morpholine derivatives as analgesics and anesthetics

Choleretics, antispasmodics, analeptics, antimalarials

Corrosion Inhibitors:Neutralizing Amine

Antioxidants

Separating Agents: Wax Emulsifier

Self polishing waxes and polishes: Surface tension depressor

Scrubbing organic sulphur compounds from fuel gas

Purification procedures

Biocide

Bacteriostatic/ bactericidal properties

Anti-fungal

Processing Industries

Processing Industries (Non-food)

Water Treatment

Handling Measures and Precautions: DG Cargo. Morpholine is hazardous in nature. Proper human safety products such as splash goggles, lab coat, dust and vapour respirator, NIOSH approved gloves and boots should be worn while handling and applying chemicals. Splashes on the skin should be washed off with water immediately. In case of splashing into the eyes, flush them with fresh water and obtain medical attention. Should not be injected. Kindly refer SDS for more details.

Storage

Morpholine should be stored in original vented containers, away from heat, direct sunlight and combustibles. Store in a cool and dry place. Kindly refer SDS for details.

1-Oxa-4-azacyclohexane

2H-1,4-Oxazine, tetrahydro-

4H-1,4-Oxazine, tetrahydro-

BASF 238

Diethylene imidoxide

Diethylene oximide

Diethyleneimide oxide

Diethylenimide oxide

Drewamine

Morpholine

MORPHOLINE

p-Isoxazine, tetrahydro-

Tetrahydro-1,4-isoxazine

Tetrahydro-1,4-oxazine

Tetrahydro-2H-1,4-oxazine

Tetrahydro-p-oxazine

MORPHOLINE

Morfolin

110-91-8

1-Oxa-4-azacyclohexane

Tetrahydro-1,4-oxazine

Diethylene oximide

Diethylenimide oxide

Diethyleneimide oxide

Drewamine

Diethylene imidoxide

morpholin

Tetrahydro-2H-1,4-oxazine

Tetrahydro-p-oxazine

p-Isoxazine, tetrahydro-

Tetrahydro-1,4-isoxazine

BASF 238

Caswell No. 584

Morpholine, 4-soya alkyl derivs.

2H-1,4-Oxazine, tetrahydro-

4H-1,4-Oxazine, tetrahydro-

EINECS 203-815-1

UN2054

C4H9NO

EPA Pesticide Chemical Code 054701

BRN 0102549

Tetrahydro-4H-1-4-oxazine

61791-40-0

Morpholine [UN2054] [Flammable liquid]

Morpholine, 99+%, extra pure

CAS-110-91-8

MORPHOLINE,REAG

Tetrahydro-p-isoxazine

MORPHOLINE, PRACT

morphline

morpho line

morpholine-

EINECS 263-172-8

4H-1, tetrahydro-

PubChem15002

Morpholine

1,4$l^{2}-oxazinane

Tetrahydro-1, 4-isoxazine

Oprea1_317540

Tetryhydro-2H-1,4-oxazine

Tetrahydro-4H-1,4-Oxazine

4-27-00-00015 (Beilstein Handbook Reference)

Morpholine, analytical standard

morfoliin (et)

Morfoliini (fi)

morfolin (cs)

morfolin (hr)

morfolin (hu)

morfolin (no)

morfolin (sl)

morfolin (sv)

morfolina (es)

morfolina (it)

morfolina (pl)

morfolina (pt)

morfolina (ro)

morfolinas (lt)

morfoline (nl)

morfolín (sk)

morfolīns (lv)

morpholin (da)

Morpholin (de)

morpholine (fr)

morfolin (tr)

morfolin (türkçe)

tetrahidro-1,4-oxazina (es)

tetrahydro-1,4-oksazyna (pl)

μορφολίν (el)

мoрфолин (bg)

CAS names

Morpholine

IUPAC names

2-chloro-1-morpholin-4-ylethanone

4H-1,4-Oxazine, tetrahydro-

Morpholin

MORPHOLINE

Morpholine

morpholine

tetrahydro 1.4 oxazine

Tetrahydro-1,4-oxazine

Tetrahydro-2H-1,4-oxazine

Tetraidro-1,4-ossazina

Trade names

1-Oxa-4-azacyclohexane

2H-1,4-Oxazine, tetrahydro-

4H-1,4-Oxazine, tetrahydro-

BASF 238

Diethylene imidoxide

Diethylene oximide

Diethylenimide oxide

Drewamine

p-Isoxazine, tetrahydro-

Tetrahydro-1,4-oxazine

Tetrahydro-2H-1,4-oxazine

Tetrahydro-p-oxazine

102549 [Beilstein]

110-91-8 [RN]

203-815-1 [EINECS]

8B2ZCK305O

MFCD00005972 [MDL number]

Morfolina [Italian]

Morfolina [Portuguese]

Morpholin [German] [ACD/IUPAC Name]

Morpholine [ACD/Index Name] [ACD/IUPAC Name] [Wiki]

Morpholine [French] [ACD/Index Name] [ACD/IUPAC Name]

QD6475000

Tetrahydro-1,4-oxazine

UNII:8B2ZCK305O

Морфолин [Russian]

モルホリン [Chinese]

吗啉 [Chinese]

吗啡啉 [Chinese]

138048-80-3 [RN]

1-Oxa-4-azacyclohexane

2H-1,4-Oxazine, tetrahydro-

4-27-00-00015 (Beilstein Handbook Reference) [Beilstein]

4H-1,4-Oxazine, tetrahydro-

Diethylene imidoxide

Diethylene oximide

Diethyleneimide oxide

diethylenimide oxide

Drewamine

Morpholine-d8

N-Vinylbenzylmorpholine-divinylbenzene Copolymer

Oprea1_317540

p-Isoxazine, tetrahydro-

ST5213815

STR00194

T6M DOTJ [WLN]

Tetrahydro-1, 4-isoxazine

Tetrahydro-1,4-isoxazine

Tetrahydro-2H-1,4-oxazine

Tetrahydro-4H-1,4-Oxazine

Tetrahydro-4H-1-4-oxazine

Tetrahydro-P-isoxazine

Tetrahydro-p-oxazine

Tetryhydro-2H-1,4-oxazine

UN 2054

UNII-8B2ZCK305O

WLN: T6M DOTJ

Other identifiers

CAS number

1357848-50-0

CAS number

1357848-50-0

Deleted CAS number

147366-31-2

CAS number

147366-31-2

Deleted CAS number

613-028-00-9

Index Number

854893-20-2

CAS number

854893-20-2

Deleted CAS number

88542-81-8

CAS number

88542-81-8

Deleted CAS number

96122-95-1

CAS number

96122-95-1

Deleted CAS number

99108-56-2

CAS number

99108-56-2

Deleted CAS number

Morpholine is a heterocycle featured in numerous approved and experimental drugs as well as bioactive molecules. It is often employed in the field of medicinal chemistry for its advantageous physicochemical, biological, and metabolic properties, as well as its facile synthetic routes. The morpholine ring is a versatile and readily accessible synthetic building block, it is easily introduced as an amine reagent or can be built according to a variety of available synthetic methodologies. This versatile scaffold, appropriately substituted, possesses a wide range of biological activities. There are many examples of molecular targets of morpholine bioactive in which the significant contribution of the morpholine moiety has been demonstrated; it is an integral component of the pharmacophore for certain enzyme active‐site inhibitors whereas it bestows selective affinity for a wide range of receptors. A large body of in vivo studies has demonstrated morpholine’s potential to not only increase potency but also provide compounds with desirable drug‐like properties and improved pharamacokinetics. In this review we describe the medicinal chemistry/pharmacological activity of morpholine derivatives on various therapeutically related molecular targets, attempting to highlight the importance of the morpholine ring in drug design and development as well as to justify its classification as a privileged structure.

Morpholine

Morpholine is a colorless, hygroscopic liquid with a characteristic amine-like odor. It is completely miscible with water and a large number of organic solvents, and is itself a solvent for a large variety of organic materials, including resins, dyes, waxes, shellac, and casein.

Molecular Formula : C4H9NO

Usage

Morpholine are mainly used to manufacture rubber accelerant (such as NOBS, OTOS and MDS), sulfuration agent (like DT-DM), cleanser, descaling agent, anti rust, anti-scorching agent, antiseptic, surfactant, textile printing & dyeing agent, optical bleaching agent, chemical plating bath, antioxidant, hydrolyzing agent, initiator, developer, fruit preserving agent, deodorizer, brightener and organic solvents. It is widely used in many industries such as medicine, pesticide, animal medicine, petroleum and extraction of coke aromatic hydrocarbon.

Morpholine (Morfolin)

CAS: 110-91-8

EC NUMARASI: 203-815-1

synonyms :

Tetrahydro-1,4-oxazine;Dieilamite oxide,;Diethylenimide Oksit oxazinane tetrahidro oksazin;morpholine;morpholine hydrochloride;morpholine hydroiodide;morpholine phosphate;morpholine phosphate (3:1);morpholine phosphonate (1:1);morpholine sulfite (1:1)morpholine;MORPHOLINE;110-91-8;Tetrahydro-1,4-oxazine;1-Oxa-4-azacyclohexane;Diethylene oximide;Diethylenimide oxide;Diethyleneimide oxide;Diethylene imidoxide;Drewamine;p-Isoxazine, tetrahydro-;Tetrahydro-p-oxazine;Tetrahydro-2H-1,4-oxazine;morpholin;Tetrahydro-1,4-isoxazine;BASF 238;Caswell No. 584;2H-1,4-Oxazine, tetrahydro-;4H-1,4-Oxazine, tetrahydro-;NSC 9376;UNII-8B2ZCK305O;CCRIS 2482;HSDB 102;EINECS 203-815-1;UN2054;EPA Pesticide Chemical Code 054701;BRN 0102549;AI3-01231;CHEBI:34856;YNAVUWVOSKDBBP-UHFFFAOYSA-N;MFCD00005972;DSSTox_CID_5688;DSSTox_RID_77880;DSSTox_GSID_25688;CAS-110-91-8;morpholine-;Morpholine, 4-soya alkyl derivs.;1,4-oxazinane;EINECS 263-172-8;MP Morpholine resin;MORPHOLINE,REAG;4H-1, tetrahydro-;PubChem15002;Morpholine Reagent Grade;MORPHOLINE, PRACT;AC1Q1IAD;AC1Q1IBT;Morpholine, polymer-bound;WLN: T6M DOTJ;NCIMech_000154;NCIOpen2_007748;Oprea1_317540;Tetrahydro-4H-1-4-oxazine;Morpholine, 99% 100g;4-27-00-00015 (Beilstein Handbook Reference);KSC175A0J;BIDD:ER0297;ACMC-20997q;Morpholine, analytical standard;MP Morpholinomethyl polystyrene;8B2ZCK305O;AC1L1Q85;CHEMBL276518;DTXSID2025688;CTK0H5004;58464-45-2 (hydriodide);NSC9376;MolPort-000-871-528;10024-89-2 (hydrochloride);BDBM140983;LTBB000400;StratoSpheres^TM PL-MPH resin;NSC-9376;STR00194;ZINC1699948;Tox21_202450;Tox21_303240;ANW-16212;AKOS000118829;Morpholine, ACS reagent, >=99.0%;Morpholine, ReagentPlus(R), >=99%;MCULE-4684386765;NA 2054;NE10420;RP18481;RP18482;RTR-002202;TRA0022240;UN 2054;63079-67-4 (unspecified phosphate);ScavengePore^TM phenethyl morpholine;NCGC00249227-01;NCGC00256942-01;NCGC00259999-01;34668-73-0 (phosphate[3:1]);61791-40-0;76088-23-8 (sulfite[1:1]);AJ-30422EP2301353A1;59619-EP2305031A1;59619-EP2305034A1;59619-EP2305035A1;59619-EP2308852A1;59619-EP2371823A1;Morpholine, purified by redistillation, >=99.5%;US8916553, 419;I14-2694;J-522715;F2190-0339;I14-113943;InChI=1/C4H9NO/c1-3-6-4-25-1/h5H,1-4H;138048-80-3;147366-31-2;6LR;854893-20-2;88542-81-8;96122-95-1;99108-56-2;Morpholine, polymer-bound, 200-400 mesh, extent of labeling: 2.75-3.25 mmol/g loading, 1 % cross-linked ScavengePore(TM) phenethyl morpholine, macroporous, 40-70 mesh, extent of labeling: 0.7-1.5 mmol/g loading StratoSpheres(TM) PL-MPH resin, 50-100 mesh, extent of labeling: 3.0-4.0 mmol/g loading, 1 % cross-linked;110-91-8 [RN];203-815-1 [EINECS];MFCD00005972 [MDL number];Morfolina [Italian];Morfolina [Portuguese];Morpholin [German] [ACD/IUPAC Name];Morpholine [ACD/Index Name] [ACD/IUPAC Name] [Wiki];Morpholine [French] [ACD/Index Name] [ACD/IUPAC Name];UNII:8B2ZCK305O;???????? [Russian];????? [Chinese];?? [Chinese];??? [Chinese];102549 [Beilstein];147366-31-2 [RN];1-Oxa-4-azacyclohexane;2H-1,4-Oxazine, tetrahydro-;342611-02-3 [RN];4-27-00-00015 (Beilstein Handbook Reference) [Beilstein];4H-1,4-Oxazine, tetrahydro-;61791-40-0 [RN];88542-81-8 [RN];96122-95-1 [RN];99108-56-2 [RN];Diethylene imidoxide;Diethylene oximide;Diethyleneimide oxide;diethylenimide oxide;Drewamine;EINECS 203-815-1;EINECS 263-172-8;Oprea1_317540;p-Isoxazine, tetrahydro-;ST5213815;T6M DOTJ [WLN];Tetrahydro-1, 4-isoxazine;Tetrahydro-1,4-isoxazine;Tetrahydro-1,4-oxazine;Tetrahydro-2H-1,4-oxazine;Tetrahydro-4H-1,4-Oxazine;Tetrahydro-4H-1-4-oxazine;Tetrahydro-P-isoxazine;Tetrahydro-p-oxazine;Tetryhydro-2H-1,4-oxazine;UN 2054;UNII-8B2ZCK305O;WLN: T6M DOTJ1,4-Oxazinan;Morpholine;MORPHOLINE,ACS;1-Oxa-4-azacyclohexane;tetrahydro-1,4-oxazine;p-Isoxazine, tetrahydro-; BASF 238; Diethylene Imidoxide; Diethylene oximide; Diethylenimide oxide; Tetrahydro-p-oxazine; Tetrahydro-1,4-oxazine; Tetrahydro-2H-1,4-oxazine; 1-Oxa-4-azacyclohexane; 2H-1,4-Oxazine, tetrahydro-; 4H-1,4-Oxazine, tetrahydro-; Diethyleneimide oxide; Tetrahydro-1,4-isoxazine; Drewamine; NA 2054; UN 2054; NSC 9376;Diethyleneimide oxide; Diethylene imidoxide; Diethylene oximide; Tetrahydro-1,4-oxazine; Tetrahydro-p-oxazine ;BASF 238;DIETHYLENE IMIDOXIDE;DIETHYLENE OXIMIDE;DIETHYLENEIMIDE OXIDE;DIETHYLENIMIDE OXIDE;DIEYTHYLENE OXIMIDE;DREWAMINE;2H-1,4-OXAZINE, TETRAHYDRO-;4H-1,4-OXAZINE, TETRAHYDRO-;MORPHOLINE;1-OXA-4-AZACYCLOHEXANE;P-ISOXAZINE, TETRAHYDRO-;TETRAHYDRO-1,4-OXAZINE;TETRAHYDRO-2H-1, 4-OXAZINE;TETRAHYDRO-2H-1,4-OXAZINE;TETRAHYDRO-P-OXAZINE;tetrahydro-1,4-Oxazine;1-Oxa-4-azacyclohexane;C4H9NO;Diethylene imidoxide;Diethylene oximide;Diethyleneimide oxide;Diethylenimide oxide;Drewamine;Morpholine ON rasta resin;Morpholine, 4-soya alkyl derivs.;Morpholine, pract;Morpholine,reag;tetrahydro-1, 4-Isoxazine;tetrahydro-1,4-Isoxazine;tetrahydro-2H-1,4-Oxazine;tetrahydro-4H-1,4-Oxazine;tetrahydro-4H-1-4-Oxazine;tetrahydro-P-Isoxazine;tetrahydro-P-Oxazine;tetryhydro-2H-1,4-Oxazine;Tetrahydro-2H-1,4-oxazine / 1-Oxa-4-azacyclohexane;Morpholine-4-Carboxylic Acid (1-(3-Benzenesulfonyl-1-Phenethylallylcarbamoyl)-3-Methylbutyl)-Amide;Morpholine; p-Isoxazine, tetrahydro-; BASF 238; Diethylene Imidoxide; Diethylene oximide; Diethylenimide oxide; Tetrahydro-p-oxazine; Tetrahydro-1,4-oxazine; Tetrahydro-2H-1,4-oxazine; 1-Oxa-4-azacyclohexane; 2H-1,4-Oxazine, tetrahydro-; 4H-1,4-Oxazine, tetrahydro-; Diethyleneimide oxide; Tetrahydro-1,4-isoxazine; Drewamine; NA 1760; NA 2054; Tetryhydro-2H-1,4-oxazine;basf238;NA 2054;BASF 238;Drewamine;MORPHOLIN;Morpholine;1,4-Oxazinan;Morpholine (B);MORPHOLINE, ACS;Morpholine ,98%;4-(5-Nitropyridin-2-yl)morpholine 2-MORPHOLIN-4-YL-PYRIMIDINE-5-CARBALDEHYDE 4-MORPHOLINOBENZYLAMINE 6-MORPHOLINONICOTINALDEHYDE ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE ETHYL 3-PYRIDYLACETATE MORPHOLIN-4-YL-ACETIC ACID 6-MORPHOLINONICOTINOYL CHLORIDE 6-MORPHOLINONICOTINIC ACID 2-MORPHOLINOBENZOIC ACID 2-MORPHOLIN-4-YL-ISONICOTINIC ACID 4-MORPHOLINECARBOXAMIDINE 4-Acryloylmorpholine 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER 4-(MORPHOLINE-4-SULFONYL)-PHENYLAMINE 2-CHLORO-3-(4-MORPHOLINYL)QUINOXALINE Methyl 3-(morpholinomethyl)benzoate ,98% 3-Amino-6-morpholinopyridine 2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL 1-(4-AMINO-2,6-DICHLOROPHENOXY)-3-MORPHOLINOPROPAN-2-OL 2-(Morpholinothio)benzothiazole 4-Morpholinophenylboronic acid Adefovir dipivoxil 6-MORPHOLINONICOTINOHYDRAZIDE 6-MORPHOLINONICOTINONITRILE MORPHOLINE-4-CARBOTHIOAMIDE 3-MORPHOLINOPHENOL 1-[2-(MORPHOLIN-4-YL)-ETHYL]-PIPERAZINE 4-(Morpholinomethyl)aniline 2-(CHLOROMETHYL)-5-METHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE (6-MORPHOLINO-3-PYRIDINYL)METHANOL 4-Methylmorpholine N-oxide monohydrate 3-Morpholinobenzaldehyde 2-(MORPHOLINE-4-CARBONYL)-BENZOIC ACID 4-(3-MORPHOLINOPROPOXY)-3,5-DICHLOROBENZENAMINE N-Formylmorpholine 4-Bromophenethyl alcohol 5-BROMO-2-(MORPHOLIN-4-YL)PYRIMIDINE 4-(2-MORPHOLINOETHOXY)-3,5-DICHLOROBENZENAMINE;Dimethylmorpholine; 4-MORPHOLINOACETOPHENONE ;4-MORPHOLINOBENZOPHENONE; 4-MORPHOLINECARBONITRILE ;1-(4-Fluorophenyl)piperazine ;3-MORPHOLINO-1,2-PROPANEDIOL 4-[2-(PIPERAZIN-1-YL)-ACETYL]-MORPHOLINE Morpholine ;2,2,2-TRIBROMOETHYL PHOSPHOROMORPHOLINOCHLORIDATE ;N-Acetylmorpholine N-(1-Cyclohexen-1-yl)morpholine N-(1-Cyclopenten-1-yl)morpholine ;4-METHYL-1-OXA-4-AZACYCLOHEXANE; 3-(4-MORPHOLINO)PROPIONITRILE N-Aminomorpholine ;4-Phenylmorpholine ;N-Formylmorpholine ;N-Ethylmorpholine1,4-Oxazinan 1,4-oxazine,tetrahydro- 2H-1,4-Oxazine, tetrahydro- 4H-1,4-Oxazine, tetrahydro- ;BASF 238; basf238 ;Diethylenimide oxide diethylenimideoxide Drewamine morpholine,aqueousmixture,[corrosivelabel] morpholine,aqueousmixture,[flammableliquidlabel] NA 2054 p-Isoxazine, tetrahydro- Tetrahydro-1,4-isoxazine Tetrahydro-1,4-oxadine Tetrahydro-1,4-oxazin tetrahydro-2h-4-oxazine tetrahydro-4h-1,4-oxazine tetrahydro-4h-4-oxazine tetrahydro-p-isoxazin Tetryhydro-2H-1,4-oxazine AKOS BBS-00003660 Alphabetic Analytical Chromatography Product Catalog Analytical Reagents Analytical Standards Building Blocks 110-91-8 LABOTEST-BB LTBB000400 DIETHYLENEIMIDE OXIDE DIETHYLENE OXIMIDE DIETHYLENE IMIDOXIDE General Use Heterocyclic Building Blocks Morpholines METI – MZ Puriss p.a. ACS MORPHOLINE ON RASTA RESIN MORPHOLIN TETRAHYDRO-P-OXAZINE TETRAHYDRO-1,4-OXAZINE TETRAHYDRO-2H-1,4-OXAZINE Morpholine 99+ % morpholine sigmaultra MORPHOLINE, STANDARD FOR GC MORPHOLINE 99+% A.C.S. REAGENT MORPHOLINE, ACS MORPHOLINE, REDISTILLED, 99.5+% MORPHOLINE REAGENTPLUS(TM) >=99% MORPHOLINE, REAGENTPLUS, >=99% MORPHOLINE PESTANAL, 250 MG MORPHOLINE GC STANDARD MORPHOLINE [C4 H9 N O] Morpholine, extra pure, 99+% Morpholine, for analysis ACS, 99+% MORPHOLINE REAGENT (ACS) C4H9ON Diethyleneimide oxide, 1-Oxa-4-azacyclohexane;Diethylene imidoxide; Diethylene oximide; 1-Oxa-4-azacyclohexane; Tetrahydro-1, 4-oxazine;Diethyleneimide oxide; tetrahydro-p-isoxazine; MOR; Morpholine;Diethylenimide Oxide, 1,4-oxazinane, tetrahydro-1,4-oxazine, Diethylene imidoxide, Diethylene oximide, Tetrahydro-p-oxazine,Morpholin.;MORFOLIN;morfoln;MORFOLN;morfolin;MORPHOLINE;morpholne;MORPHOLNE;morpholine; mor folin; morfoline; morpholin; morpholne

Morpholine

Production

Morpholine is often produced industrially by the dehydration of diethanolamine with sulfuric acid:[6]

Morpholine from DEA.png

Uses

Industrial applications

Morpholine is a common additive, in parts per million concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH-adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly in the absence of oxygen at the high temperatures and pressures in these steam systems.

Organic synthesis

It is commonly used to generate enamines.[8]

In research and in industry, the low cost and polarity of morpholine lead to its common use as a solvent for chemical reactions.

Agriculture

As a fruit coating

Morpholine is used as a chemical emulsifier in the process of waxing fruit. Naturally, fruits make waxes to protect against insects and fungal contamination, but this can be lost as the fruit is cleaned. A small amount of new wax is applied to replace it. Morpholine is used as an emulsifier and solubility aid for shellac, which is used as a wax for fruit coating.[9] The European Union has forbidden the use of morpholine in fruit coating.[10][11]

As a component in fungicides

Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.

Amorolfine

Fenpropimorph

Tridemorph

EC NUMBER: 203-815-1

Appearance: Transparent liquid

Molecular formula: 2NH. O (CH2CH2)

Humidity: 0.5% max

Boiling range (5- 95%) 0C: 126-129 0C

Boiling point: 128.3 ºC

Freezing point: – 4.9 0C

Viscosity (200 C): 2.3 Cp

Lower explosion limit% (V / V): 1.8

Heat capacity (Cp): 173.89 J / (mol · K)

MORFOLINE is a light, viscous, oily liquid, colorless and transparent raw material with a unique amine odor.

It is used in many industrial areas, especially in water treatments. It is used as a good metal corrosion protector.

General Information of Morpholine

Morpholine, which has the chemical formula O (CH2CH2) 2NH, is a hygroscopic, weakly basic, oily, slightly aromatic volatile liquid and mixes with many organic solvents such as ethanol, methanol, acetone, ethers, BTX (used as a solvent of its own). It decomposes by giving toxic nitrogen oxides with heat and gives strong reactions with strong oxidations, resulting in danger of fire, and attacks copper and copper compounds. Solubility in alkaline solutions is limited.

Production and Reactions of Morpholine

Diethylene glycol can be prepared by reductive amination with hydrogen. Ammonia can be prepared by heating bis (chloroethyl) ether with a strong acid dehydrogenation of the diethanol amine

Usage areas of Morpholine

Water of Morpholine

Corrosion inhibitors are also used as intermediates in the steam boiler water treatment systems and in aqueous hydraulic fluids to protect metals from corrosion and dulling (darkening) with acid vapors.

Detergent of Morpholine

It is used as an additive in optical brighteners for chlorine bleaching for use in detergents.

Cosmetic of Morpholine

Is used in fatty acid salts for water-resistant emulsifiers and plasticizer formulations in cosmetic products. It is also used as an intermediate in quaternary morpholinium salts for hair conditioners and deodorant products.

Medicine of Morpholine

Drugs (analgesics, locust anesthetics, antibiotics, antimycotics and antiplat) are used as intermediates in the production of products.

Morpholine is a weaker base. The melting point is -5 ° C and the boiling point is 129 ° C. The density is 0.999 g / mL. A hygroscopic liquid, morpholine can be mixed with water and many organic solvents. A characteristic amine smell

It has. Under normal conditions, morpholine, which is highly stable, decomposes at the end of the overheating and ignites when it forms nitrogen oxide, entering into severe reaction with strong oxidants. It is a very stable and useful molecule.

Used as a solution for resins and paints. Alkyl derivatives are used as catalysts in the production of polyurethane foams. There are many more uses in the industry including food industry.

Experimental Properties of Morpholine

Physical Description of Morpholine

MORPHOLINE is a colorless liquid with a fishlike odor. Flash point 100°F. Corrosive to tissue. Less dense than water and soluble in water. Vapors heavier than air. Used to make other chemicals, as a corrosion inhibitor, and in detergents.

Morpholine, CAS Number 110-91-8, is a colorless, mobile, hygroscopic liquid with a characteristic amine-like odor. It is completely miscible with water and a large number of organic solvents, and is itself a solvent for a large variety of organic materials, including resins, dyes, waxes,shellac, and casein.Morpholine is an extremely versatile chemical with many important applications. It is used as an intermediate in the manufacture of rubber chemicals and optical brighteners. It is also used extensively as a corrosion inhibitor in steam boiler systems.Fatty acid derivatives of morpholine are used as emulsifiers in the manufacture of waxes and polishes.Other derivatives have found applications as bactericides,pharmaceutical chemicals, and antioxidants for lubricating oils. Morpholine derivatives are particularly useful in the textile industry, where they are employed as textile lubricants and sizing emulsifiers.Chemically, morpholine is an amino ether. The ether function of the molecule is typically inert and most of the reactions of morpholine involve the secondary amine group.

Catalysts of Morpholine

Morpholine has been employed as a catalyst for the condensation of aldehydes and ketones which contain active methyl or methylene groups. The condensates may

be hydrogenated to polyhydroxy compounds which can be sulfated to form surface-active agents.Small quantities of morpholine are used in the emulsion polymerization of monomers, such as butadiene and isoprene, as well as their copolymerization with styrene,acrylonitrile, and the like.Morpholine has been used as a temperature sensitive polymerization inhibitor. Small amounts permit complete impregnation of porous materials with molten vinylpyrroletype monomers just above their melting points, but still allow complete polymerization at slightly higher temperatures.Morpholine has also been used as a gelling agent in the preparation of alumina catalysts for the treatment of hydrocarbons. Catalysts of fine particle size suitable for fluidized solid techniques result from this procedure.

Morpholine is a permitted (FDA) in edible coatings for fruit and vegetables. Morpholine is a food contaminant arising from its use as a boiler water additive Morpholine is a common additive, in ppm concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly in the absence of oxygen even at the high temperatures and pressures in these steam systems. Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle, pictured at right, features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, when morpholine is neutralized by hydrochloric acid, one obtains the salt morpholinium chloride. Morpholine is widely used in organic synthesis. For example, it is a building block in the preparation of the antibiotic linezolid and the anticancer agent gefitinib (Iressa). Morpholine has been shown to exhibit anti-mycotic and anti-fungal functions (PMID 7279992 , 8077515 ). Morpholine belongs to the family of Oxazinanes. These are compounds containing an oxazinane moiety, which consists of a saturated aliphatic six-member ring with one oxygen atom, a nitrogen atom, and four carbon atoms. Isomers of oxaphospholane include 1,2-oxazinane, 1,3-oxazinane, and 1,4-oxazinane.

Product Features of Morpholine

Morpholine, also known as 1, 4-oxazepine and diethylenimine oxide, is a kind of colorless alkaline oily liquid. It smells of ammonia and has hygroscopicity. Morpholine could evaporate with water vapor and miscible with water. It is Soluble in acetone, benzene, ether, pentane, methanol, ethanol, carbon tetrachloride, propylene glycol and other organic solvents. Morpholine Vapor could form an explosive mixture with air and the explosion limit is 1.8% to 15.2% (volume fraction). Morpholine is a secondary amine, and at the same time it has the property of inorganic acid and organic acid, so that it can generate salt and amide.

Morpholine contains secondary amine groups and it has all the typical reaction characteristics of the secondary amine groups. It can react with inorganic acid to form a salt, and also can react with organic acid to form salt or amide. Morpholine can carry out alkylation reactions and it also carry out ketone reaction or Willgerodt reaction with ethylene oxide. Because of the unique chemical properties of morpholine, it has become one of the important petrochemical products with important commercial application. It can be applied to produce rubber vulcanization accelerators such as NOBS, DTOS and MDS. And it is also applied to produce anti-corrosives, anti-corrosion agents, detergents, detergents, analgesics, local anesthetics, sedatives, respiratory and vascular stimulants, surfactants, optical bleach, fruit preservatives, and textile dyeing auxiliaries. Morpholine also has a wide range of applications in the field of rubber, pharmaceuticals, pesticides, dyes, coatings and other industries. In medication it could be applied in the production of morpholine guanidine, virus Ling, ibuprofen, cough must, naproxen, dichloroaniline, sodium phenylacetate and other important drugs.

The two main production method of morpholine are DEA method (diethanolamine method) and DEA method (diethylene glycol method)

It is noteworthy that new polymer monomer acrylic morpholine has obtained a rapid development in recent years. Acrylic acid morpholine could be produced from the reaction between acrylic acid and morpholine. And acrylic acid morpholine is a kind of water-soluble monomer, and it is still water-soluble after the polymerization. So it could be applied for the modification of aqueous polymers. Besides, acrylic morpholine is widely used as a reactive diluent for UV curable resins. With the deepening of applied research, many new specific uses have been developed and it becomes polymer monomer with rapid development.

Chemical properties of Morpholine

It is colorless water-absorbing oily liquid and it smells ammonia. It is soluble in water and methanol, ethanol, benzene, acetone, ether, ethylene glycol and other commonly used solvents.

Uses of Morpholine

(1) For medicine, it used as the raw materials for rubber accelerator and fluorescent whitening agent.

(2) Morpholine is the intermediates of fungicide dimethomorph and flumorpholine and organophosphate insecticide phosalphos.

(3) Morpholine is Mainly used for the production of rubber vulcanization accelerator, but also for surfactant, textile auxiliaries, pharmaceuticals, pesticide synthesis. (4) Morpholine also used as a catalyst for polymerization of butadiene, corrosion inhibitors, optical bleach, the goods are dyes, resins, wax, early glue, casein and other solvents. At present, the total production of morpholine in the world is 3-4 million t/a.

(5) Morpholine salts are also widely used. Morpholine salts like morpholine hydrochloride (10024-89-2) are the organic synthesis of intermediates. Morpholine fatty acid salt can be used as the coating agent of fruits or vegetables epidermal coating agent, and it could inhibit the base respiration and prevent the epidermis from evaporation of water and epidermal atrophy.

(6) Morpholine is the main raw materials of accelerator NOBS. for analysis reagents and resins, wax, shellac and other solvents, used in the production of sodium sulfate. Water glass and ultramarine. Also used in the manufacture of glass. Paper. Detergent. Soap. Dye. Synthetic fiber. Tanning. Medicine and ceramics industries. Analysis reagents, such as nitrogen determination, dehydrating agent.

(7) Morpholine is used for the analysis of reagents and resins, wax, casein, shellac and a variety of solvents solvent.

(8) Morpholine could produce salt after reacting with inorganic acid, and it also could produce salt or amide after reacting with organic acid. It also can be alkylated, and it also could come up a ketone reaction or Willgerodt reaction with ethylene oxide.

Morpholine are mainly used to manufacture rubber accelerant (such as NOBS, OTOS and MDS), sulfuration agent (like DT-DM), cleanser, descaling agent, antirust, anti-scorching agent, antiseptic, surfactant, textile printing & dyeing agent, optical bleaching agent, chemical plating bath, antioxidant, hydrolyzing agent, initiator, developer, fruit preserving agent, deodorizer, brightener and organic solvents. It is widely used in many industries such as medicine, pesticide, animal medicine, petroleum and extraction of coke aromatic hydrocarbont.

In foreign countries, a great deal of morpholine is used for antirust, descaling and metal cleaning, especially for antirust and anticorrosive in high temperature conditions. In boiler maintenance fields, amount of morpholkine is also used as descaling agent. Owing to its unique chemical characters, morpholine has become one of the most important fine petroleum chemical products.

A colorless, hygroscopic liquid with a characteristic amine odor. Morpholine is miscible with water, but it evolves heat in the process forming a basic solution that can saponify dried oil films and aid in their removal. Morpholine is also used to dissolve resins, waxes, casein, shellac, and dyes. It can also act as a surfactant and emulsifier. Morpholine has been used as a corrosion inhibitor in fire sprinkler and HVAC systems. It has also been used as a vapor phase neutralizing/alkalizing agent, but it is not recommended because of its toxicity, disagreeable odor, and poor ability to provide residual alkalinity. Some materials treated with morpholine, such as leather and pyroxylin coated book covers, have exhibited color changes (Book and Paper Catalog)

Morpholine is a clear, colorless, volatile, hygroscopic liquid with a characteristic amine odor. It is miscible in water and most organic solvents. The mixture of morpholine and water does not have a constant boiling point. Therefore morpholine in aqueous solution is not easily separable by distillation or entraining. It is a heterocyclic chemical compound, which has both a secondary amine and an ether functional group; its molecule has a chair structure. Morpholine is chemically stable and is not expected to degrade in hot water, acid and alkali solutions. It forms morpholinium salts with mineral acids. It reacts with aldehydes and ketones with hydrogen atoms in alfa-position to form enamines.

MORFOLN

Görünü: effaf sv

Moleküler formül: 2NH. O (CH2CH2)

Nem: maksimum% 0.5

Kaynama aral (% 5-95) 0C: 126-129 0C

Kaynama noktas: 128.3 ºC

Donma noktas: – 4.9 0C

Viskozite (200 ° C): 2.3 Cp

Patlama alt snr% (V / V): 1.8

Is kapasitesi (Cp): 173.89 J / (mol K)

MORFOLINE, hafif, viskoz, yal bir sv, benzersiz bir amin kokusu olan renksiz ve effaf bir hammaddedir.

Birçok endüstriyel alanda, özellikle su artmnda kullanlr. yi bir metal korozyon koruyucusu olarak kullanlr.

Morfolin Hakknda Genel Bilgiler

O (CH2CH2) 2NH kimyasal formüle sahip olan morfolin, higroskopik, zayf derecede bazik, yal, hafifçe aromatik uçucu bir sv olup, etanol, metanol, aseton, eterler, BTX gibi bir çok organik çözücü madde ile karr (onun solventi olarak kullanlr). kendi). Toksik azot oksitleri s ile parçalayarak bozunur ve güçlü oksidasyonlar ile güçlü tepkiler verir ve yangn tehlikesine neden olur ve bakr ve bakr bileiklerine saldrr. Çözelti alkali çözeltilerde snrldr.

Morfolinin Üretimi ve Reaksiyonlar

Dietilen glikol, hidrojen ile indirgeyici aminasyon ile hazrlanabilir. Amonyak, bis (kloroetil) eteri, dietanol aminin güçlü bir asit dehidrojenasyonuyla stmak suretiyle hazrlanabilir

Morpholine kullanm alanlar

Morfolin Suyu

Korozyon önleyiciler, buhar kazan su artma sistemlerinde ve metalleri korozyona ve asit buhar ile donuklatrmaya (koyulatrmaya) kar korumak için sulu hidrolik svlardaki ara maddeler olarak da kullanlrlar.

Morfolin Deterjan

Deterjanlarda kullanlmak üzere klorlu aartma için optik parlatclarda bir katk maddesi olarak kullanlr.

Morfolin Kozmetik

Ya asidi tuzlarnda, kozmetik ürünlerdeki suya dayankl emülgatörler ve plastikletirici formülasyonlar için kullanlr. Saç kremleri ve deodorant ürünleri için kuarterner morfolinyum tuzlarnda ara madde olarak da kullanlr.

Morfolin laçlar

laçlar (analjezikler, çekirge anestezi, antibiyotikler, antimikotikler ve antiplat) ürünler üretiminde ara ürünler olarak kullanlrlar.

Morfolin daha zayf bir tabandr. Erime noktas -5 ° C ve kaynama noktas 129 ° C’dir. Younluk 0.999 g / mL’dir. Higroskopik bir sv morfolin su ve birçok organik çözücü madde ile kartrlabilir. Karakteristik bir amin kokusu

Var. Normal koullar altnda, oldukça kararl morfolin, ar snmann sonunda parçalanr ve azot oksit oluturduunda atelenir ve güçlü oksitleyiciler ile iddetli reaksiyona girer. Çok kararl ve kullanl bir moleküldür.

Reçineler ve boyalar için bir çözüm olarak kullanlr. Alkil türevleri, poliüretan köpüklerin üretiminde katalizörler olarak kullanlr. Gda sanayii de dahil olmak üzere sanayide çok daha fazla kullanm alan vardr.

Morfolinin Deneysel Özellikleri

Morfolinin Fiziksel Tanm

MORFOLN, balk benzeri bir kokuya sahip, renksiz bir svdr. Parlama noktas 100 ° F. Dokuya kar koroziftir. Suya göre daha az youn ve suda çözünür. Buhar havadan daha ar. Korozyon önleyici olarak ve deterjanlarda dier kimyasallar yapmak için kullanlr.

Morfolin, CAS Numaras 110-91-8, karakteristik bir amin benzeri kokusu olan, renksiz, mobil, higroskopik bir svdr. Su ve çok sayda organik çözücü madde ile tamamen karabilir ve kendisi reçineler, boyalar, mumlar, gomalak ve kazein gibi çok çeitli organik materyaller için bir çözücüdür. Morfolin birçok önemli uygulamayla çok yönlü bir kimyasaldr. Kauçuk kimyasallar ve optik parlatclarn üretiminde bir ara madde olarak kullanlr. Ayrca, buhar kazan sistemlerinde korozyon önleyici olarak yaygn ekilde kullanlr. Morfolinin yal asit türevleri, mum ve polis üretiminde emülsiyon yapc olarak kullanlr. Dier türevleri, yalayc yalar için bakterisidler, farmasötik kimyasallar ve antioksidanlar olarak uygulamalar bulmutur. Morfolin türevleri, tekstil yalayclar ve boyutlandrma emülsiyonlatrclar olarak kullanldklar tekstil endüstrisinde özellikle yararldr. Kimyasal olarak, morfolin bir amino eterdir. Molekülün eter fonksiyonu tipik olarak etkisizdir ve morfolin reaksiyonlarnn çou ikincil amin grubunu içerir.

Morfolin Katalizörleri

Morfolin, aktif metil veya metilen gruplar içeren aldehitler ve ketonlarn younlatrlmas için bir katalizör olarak kullanlmtr. Younlam maddeler

Yüzey aktif maddeler oluturmak üzere sülfatlanabilen polihidroksi bileiklerine hidrojenletirilebilirler. Mütale miktarlarnda morfolin, bütadien ve izopren gibi monomerlerin emülsiyon polimerizasyonunda ve bunlarn stiren, akrilonitril ve benzeri ile kopolimerizasyonu için kullanlr. Morfolin Scaklk duyarl polimerizasyon inhibitörü olarak kullanlmtr. Az miktarda gözenekli materyallerin ergime noktalarnn hemen üstünde ergimi vinilpirolite monomerleri ile emprenye edilmesine izin verir, ancak yine de biraz daha yüksek scaklklarda tam polimerizasyona izin verir. Morfolin ayn zamanda hidrokarbonlarn ilenmesi için alümina katalizörlerinin hazrlanmasnda jelletirici bir madde olarak da kullanlr. Akkanlatrlm kat teknikler için uygun olan ince partikül boyutu katalizörleri bu prosedürden sonuçlanr.

Morfolin meyve ve sebzeler için yenilebilir kaplamalarda izin verilen (FDA) bir maddedir. Morfolin, bir kazan suyu katk maddesi olarak kullanlmasndan kaynaklanan bir gda kirleticisidir Morfolin, ppm konsantrasyonlarda, hem fosil yaktta hem de nükleer enerji santrali buhar sistemlerinde pH ayarlamas için ortak bir katk maddesidir. Morfolin, volatilitesi su ile ayn olduu için kullanlr, bu yüzden suya ilave edildiinde, konsantrasyonu su ve buhar fazlarnda eit olarak datlr. Bu durumda, pH ayarlama nitelikleri korozyona kar koruma salamak için buhar tesisat boyunca datlr. Morfolin genellikle bu tür bitkilerin buhar sistemleri için korozyon korumas için kapsaml, uçucu bir muamele kimyas salamak için düük konsantrasyonda hidrazin veya amonyak ile birlikte kullanlr. Morfolin, bu buhar tesisatlarndaki yüksek scaklk ve basnçlarda bile oksijenin yokluunda makul derecede yava ayrr. Morfolin kimyasal formülü O (CH2CH2) 2NH olan organik bir kimyasal bileiktir. Sadaki resimde görülen bu heterosiklil hem amin hem de eter fonksiyonel gruplara sahiptir. Amin nedeniyle morfolin bir bazdr; Elenik asitine morfolinyum denir. Örnein, morfolin hidroklorik asit ile nötrletirildiinde, bir tuz morfolinyum klorür elde edilir. Morfolin yaygn olarak organik sentezde kullanlr. Örnein, bu, antibiyotik linezolid ve anti kanser ajan olan gefitinib (Iressa) ‘nn hazrlanmasnda bir yap tadr. Morfolinin, anti-mikotik ve anti-fungal ilevleri sergiledii gösterilmitir (PMID 7279992, 8077515). Morfolin, Oxazinanes ailesine aittir. Bunlar, bir oksazinan ksm ihtiva eden, bir oksijen atomu, bir azot atomu ve dört karbon atomlu doymu bir alifatik alt üyeli halkadan oluan bileiklerdir. Okzafosfolann izomerleri 1,2-oksazinan, 1,3-oksazinan ve 1,4-oksazinan içerir.

Bu bileik, morfolinler olarak bilinen organik bileik snfna aittir. Bunlar, srasyla oksijen ve azot atomlarnn srasyla 1 ve 4 pozisyonlarnda C4H9NO formülüne sahip alt üyeli bir alifatik doymu halkadan oluan bir morfolin yarm içeren organik bileiklerdir.

Morfolinin Ürün Özellikleri

Morfolin, ayn zamanda 1, 4-oksazepin ve dietilenimin oksit olarak bilinir, bir renksiz alkalin yal sv türüdür. Amonyak kokuyor ve higroskopik özellii var. Morfolin su buhar ile buharlaabilir ve suyla karabilir. Aseton, benzen, eter, pentan, metanol, etanol, karbon tetraklorür, propilen glikol ve dier organik çözücüler içinde çözünür. Morfolin Buhar havayla patlayc bir karm oluturabilir ve patlama limiti% 1.8 ila% 15.2 arasndadr (hacim fraksiyonu). Morfolin ikincil bir amindir ve ayn zamanda inorganik asit ve organik asit özelliine sahiptir, böylece tuz ve amid üretebilir.

Morfolin ikincil amin gruplar içerir ve ikincil amin gruplarnn tüm tipik reaksiyon özelliklerine sahiptir. norganik asit ile reaksiyona girerek bir tuz oluturabilir ve organik asit ile tepkimeye girerek tuz veya amid oluturabilir. Morfolin alkilasyon reaksiyonlarn gerçekletirebilir ve etilen oksit ile keton reaksiyonu veya Willgerodt reaksiyonu gerçekletirir. Morfolinin benzersiz kimyasal özellikleri nedeniyle, önemli ticari uygulamalarla önemli petrokimyasal ürünlerden biri haline gelmitir. NOBS, DTOS ve MDS gibi kauçuk vulkanizasyon hzlandrclar üretmek için uygulanabilir. Ayrca anti-korozif, korozyon önleyici ajanlar, deterjanlar, deterjanlar, analjezikler, lokal anestezi, sedatifler, solunum ve vasküler uyarclar, yüzey aktif maddeler, optik aartc, meyve koruyucular ve tekstil boyama yardmc maddeleri üretmek için de uygulanr. Morfolin ayn zamanda kauçuk, ilaç, böcek öldürücü, boya, kaplama ve dier endüstrilerde geni bir uygulama yelpazesine sahiptir. laçta morfolin guanidin, virüs Ling, ibuprofen, öksürük gerekir, naproksen, dikloroanilin, sodyum fenilasetat ve dier önemli ilaçlarn üretiminde uygulanabilir.

Morfolinin iki ana üretim yöntemi DEA yöntemi (dietanolamin yöntemi) ve DEA yöntemi (dietilen glikol yöntemi)

Yeni polimer monomer akrilik morfolinin son yllarda hzl bir gelime kaydettiine dikkat çekilmelidir. Akrilik asit morfolin, akrilik asit ve morfolin arasndaki reaksiyondan üretilebilir. Akrilik asit morfolin, bir çeit suda çözünür monomerdir ve polimerizasyon sonrasnda halen suda çözünürdür. Dolaysyla, sulu polimerlerin modifikasyonu için de uygulanabilir. Ayrca, akrilik morfolin UV ile iyiletirilebilen reçineler için reaktif bir seyreltici olarak yaygn olarak kullanlmaktadr. Uygulanan aratrmann derinlemesiyle birçok yeni özel kullanmlar gelitirilmi ve hzla gelien polimer monomer haline gelmitir.

Morfolinin kimyasal özellikleri

Renksiz su emici yal svdr ve amonyak kokar. Su ve metanol, etanol, benzen, aseton, eter, etilen glikol ve yaygn olarak kullanlan dier solventlerde çözünür.

Morfolin Kullanm

(1) laçlar için kauçuk hzlandrc ve flüoresan beyazlatma ajan ham maddesi olarak kullanlr.

(2) Morfolin fungisit dimetomorf ve flumorfolin ve organofosfat insektisid fosalfoslarnn ara ürünleridir.

(3) Morfolin Esas olarak kauçuk vulkanizasyon hzlandrc üretimi için deil ayn zamanda sürfaktan, tekstil yardmc maddeleri, ilaçlar, böcek öldürücü sentezi için de kullanlr.

(4) Morfolin ayn zamanda bütadien, korozyon önleyiciler, optik aartclarn polimerizasyonu için bir katalizör olarak da kullanlr; ürünler boyalar, reçineler, balmumu, erken tutkal, kazein ve dier çözücülerdir. u anda dünyadaki morfoline toplam üretim 3-4 milyon ton / a’dr.

(5) Morfolin tuzlar da yaygn ekilde kullanlr. Morfolin hidroklorür (10024-89-2) gibi morfolin tuzlar ara ürünlerin organik sentezidir. Meyvelerin veya sebzelerin epidermal kaplama maddesinin kaplama maddesi olarak Morfolin ya asidi tuzu kullanlabilir ve baz solunumunu engelleyebilir ve epidermisin suyun buharlamasn ve epidermal atrofi önleyebilir.

(6) Morfolin hzlandrc NOBS’un ana hammaddesidir. Reaktifler ve reçineleri analiz etmek için, sodyum sülfat üretiminde kullanlan mum, gomalak ve dier çözücüler. Su barda ve ultramarin. Ayrca cam üretiminde de kullanlr. Kat. Deterjan. Sabun. Boya. Sentetik elyaf. Bronzlama. Tp ve seramik endüstrileri. Analiz reaktifleri, örnein azot tayini, kurutucu madde.

(7) Morfolin, ayraç ve reçineler, mum, kazein, gomalak ve çeitli çözücü solventlerinin analizi için kullanlr.

(8) Morfolin, inorganik asit ile reaksiyona girdikten sonra tuz üretebilir ve ayrca organik asit ile reaksiyona girdikten sonra tuz veya amid üretebilir. Ayn zamanda alkilletirilebilir ve etilen oksit ile bir keton reaksiyonu veya Willgerodt reaksiyonu ortaya çkabilir.

Morfolin esas olarak kauçuk hzlandrc (NOBS, OTOS ve MDS gibi), sülfürletirici ajan (DT-DM gibi), temizleyici, kireç çözücü ajan, anti-kavurucu ajan, antiseptik, yüzey aktif, tekstil bask ve boya ajan, optik Aartma maddesi, kimyasal kaplama banyosu, antioksidan, hidrolize edici ajan, balatc, gelitirici, meyve koruyucusu, koku giderme maddesi, parlatc ve organik çözücüler. Tp, ilaçlama, hayvan tbb, petrol ve kola aromatik hidrokarbonun ekstre edilmesi gibi birçok sanayide yaygn olarak kullanlmaktadr.

Yabanc ülkelerde, yüksek scaklk koullarnda antirust, pas önleyici ve antikorozif olarak antifriz, kireç çözme ve metal temizleme için büyük miktarda morfolin kullanlr. Kazan bakm alanlarnda morfolkinin miktar da tufal giderme maddesi olarak kullanlr. Benzersiz kimyasal karakterleri nedeniyle, morfolin en önemli ince petrol kimyasal ürünlerinden biri haline geldi.

Karakteristik bir amin kokusu olan, renksiz, higroskopik bir sv. Morfolin su ile karabilir, ancak kuru bir ya filmini sabunlatracak ve bunlarn uzaklatrlmasna yardmc olan temel bir solüsyon oluturan ilem srasnda sy dönütürür. Morfolin ayrca reçineler, mumlar, kazein, gomalak ve boyalar çözmek için kullanlr. Ayn zamanda bir sürfaktan ve emülgatör olarak da ilev görür. Morfolin, yangn sprinkler ve HVAC sistemlerinde korozyon önleyici olarak kullanlr. Ayrca buhar faz nötralize edici / alkaliletirici bir madde olarak da kullanlr, ancak toksisitesi, rahatsz edici koku ve kalnt alkalilik temin etme yeteneinden ötürü önerilmez. Deri ve piroksil kapl kitap kapaklar gibi morfolin ile muamele edilen baz malzemeler renk deiiklikleri sergilemitir

Morfolin, karakteristik bir amin kokusu olan, berrak, renksiz, uçucu, higroskopik bir svdr. Suda ve organik solventlerin çounda karabilir. Morfolin ve su karm sabit bir kaynama noktasna sahip deildir. Bu nedenle, sulu solüsyondaki morfolin, damtlmas veya sürüklenmesiyle kolaylkla ayrlabilir deildir. Hem ikincil bir amin hem de bir eter fonksiyonel gruba sahip olan heterosiklik bir kimyasal bileiktir; Molekülünün bir koltuk yaps vardr. Morfolin kimyasal olarak kararldr ve scak su, asit ve alkali çözeltilerinde bozunmas beklenmez. Mineral asitlerle morfolinyum tuzlar oluturur. Enaminler oluturmak için alfa pozisyonundaki hidrojen atomlaryla aldehitler ve ketonlarla reaksiyona girer.

Morpholine

Identification

Nom UICPA tétrahydro-1,4-oxazine

No CAS 110-91-8

No ECHA 100.003.469

No CE 203-815-1

SMILES

[Afficher]

InChI

[Afficher]

Apparence liquide hygroscopique, incolore, d’odeur caractéristique1

Propriétés chimiques

Formule brute C4H9NO [Isomères]

Masse molaire4 87,1204 ± 0,0043 g/mol

C 55,15 %, H 10,41 %, N 16,08 %, O 18,36 %,

pKa 8,33

Moment dipolaire 1,55 ± 0,03 D 2

Diamètre moléculaire 0,542 nm 3

Propriétés physiques

T° fusion -5 °C1

T° ébullition 129 °C1

Solubilité dans l’eau : miscible1

Paramètre de solubilité δ 21,8 J1/2·cm-3/2 (25 °C)3

Masse volumique 0,9994 g·cm-3 5

T° d’auto-inflammation 310 °C1

Point d’éclair 35 °C (coupelle ouverte)1

Limites d’explosivité dans l’air 1,4-11,2 %vol1

Pression de vapeur saturante à 20 °C : 1,06 kPa1

Point critique 54,7 bar, 344,85 °C 6

La morpholine est un hétérocycle saturé porteur d’une fonction éther et d’une fonction amine secondaire. Cette dernière lui confère les propriétés d’une base. La morpholine donne aussi son nom à une classe de composés dont elle est l’élément le plus simple.

La morpholine se présente sous la forme d’un liquide huileux, incolore, avec une odeur caractéristique d’amine.

La morpholine est hygroscopique et totalement miscible à l’eau.

Propriétés chimiques

La morpholine présente les propriétés chimiques caractéristiques d’une amine secondaire. Cependant, la présence de l’oxygène dans l’hétérocycle a pour effet de réduire la densité électronique sur l’atome d’azote. Les propriétés nucléophiles et basiques de la morpholine sont donc moins marquées que pour les amines secondaires de structure proche (la pipéridine par exemple).

Synthèse

En laboratoire

Deux voies de synthèse de la morpholine

Dans l’industrie

La morpholine peut être synthétisée industriellement par réaction de l’ammoniac sur le diéthylène glycol en présence d’hydrogène et de catalyseurs :

Morpholine synthesis.png

Utilisation

La morpholine a un grand nombre d’utilisations :

comme intermédiaire dans l’industrie du caoutchouc ;

comme élément de synthèse dans la préparation de certains médicaments (exemple : l’antibiotique Linézolide) ;

dans la préparation de produits phytosanitaires (exemple : les fongicides Tridémorphe et Fenpropimorphe) ;

la synthèse de colorants.

Elle est aussi utilisée comme agent anticorrosion. Elle est par exemple ajoutée à l’eau qui circule dans les turbines à vapeur des centrales thermiques à flamme ou nucléaires12 pour maintenir un pH légèrement basique et prévenir la corrosion (pH de moindre corrosion requis). En maintenant un pH légèrement basique, elle limite l’effet corrosif de l’eau à haute température sur les pièces métalliques. Les avantages de la morpholine dans cette utilisation résident dans sa bonne stabilité chimique en l’absence d’oxygène et dans sa température d’ébullition suffisamment proche de celle de l’eau, ce qui garantit une distribution relativement homogène entre la phase liquide et la phase vapeur du mélange.

Utilisations

Propriétés physiques

Nom Substance Détails

Morpholine N° CAS 110-91-8

Etat Physique Liquide

Masse molaire 87,1

Point de fusion -5 à -4,9 °C

Point d’ébullition 128 à 130 °C

Densité 1

Densité gaz / vapeur 3

Pression de vapeur 1,1 kPa à 20 °C

8,3 kPa à 60 °C

40,9 kPa à 100 °C

Indice d’évaporation 0,46

Point d’éclair 31 à 35 °C (coupelle fermée)

38 à 43 °C (coupelle ouverte)

Température d’autoinflammation

275 à 310 °C

Limites d’explosivité ou

d’inflammabilité (en volume

% dans l’air)

Limite inférieure : 1,4 %

Limite supérieure : 11,2 %

Coefficient de partage noctanol / eau (log Pow)

-2,55 (mesuré à 25 °C)

Propriétés chimiques

Récipients de stockage

[1 à 6]

Intermédiaire de synthèse en chimie organique (par exemple, production de dérivés de la morpholine utilisés comme catalyseurs).

Inhibiteur de corrosion.

Fabrication d’azurants optiques et d’additifs pour caoutchouc.

Solvant pour résines, colorants et cires.

La morpholine étant inscrite à l’annexe III du règlement (CE) n° 2032/2003 (relatif aux produits biocides) de la Commission européenne du 4 novembre 2003, la mise

sur le marché de produits biocides contenant de la morpholine est interdite sur le territoire de l’Union européenne depuis le 1 e septembre 2006. r

[1 à 9]

La morpholine est un liquide incolore, huileux, hygroscopique, volatil et qui possède l’odeur de poisson caractéristique des amines (seuil olfactif = 0,01 ppm ou 0,036

mg/m ). Elle est miscible à l’eau (pH d’une solution aqueuse à 10 % = 11,2) et soluble dans de nombreux solvants organiques notamment l’acétone, l’éthanol et

l’éthylèneglycol.

À 20 °C et 101 kPa, 1 ppm = 3,62 mg/m 3.

[2, 3, 6]

Dans les conditions normales d’emploi, la morpholine est un produit stable et insensible à la lumière. Chimiquement, elle se comporte comme une amine secondaire.

La morpholine est une base qui peut réagir violemment avec les acides concentrés. Elle réagit également avec les acides gazeux tels que le sulfure d’hydrogène, le gaz

carbonique et le cyanure d’hydrogène pour former des sels de la morpholine.

La morpholine peut également réagir violemment avec des agents oxydants tels que les perchlorates, permanganates, nitrates, chromates, halogènes, peroxydes et

l’acide nitrique.

En solution aqueuse et en présence d’acide nitreux ou de nitrites, elle peut former de la N-nitrosomorpholine classée par le CIRC (Centre International de Recherche

sur le Cancer) dans le groupe 2B des substances « peut-être cancérogènes pour l’homme ».

Elle attaque le cuivre, l’aluminium, le zinc et leurs alliages.

La combustion de la morpholine libère, suivant les conditions réactionnelles, des composés toxiques notamment des oxydes de carbone et d’azote, du cyanure

d’hydrogène et des nitosamines.

[2, 6, 7]

Le stockage peut s’effectuer dans des récipients en acier.

Certains matériaux sont déconseillés : cuivre, aluminium, zinc et leurs alliages ainsi que certaines matières plastiques

Valeurs Limites d’Exposition Professionnelle

Substance Pays VME (ppm) VME (mg/m³) VLCT (ppm) VLCT (mg/m³)

Morpholine Union européenne 10 36 20 72

Morpholine Etats-Unis (ACGIH) 20 71 – –

Morpholine Allemagne (valeurs MAK) 10 36 – –

Méthodes de détection et de détermination dans l’air

Incendie – Explosion

Pathologie – Toxicologie

Toxicocinétique – Métabolisme

Chez l’animal

Absorption

Distribution

Métabolisme

Elimination

Des valeurs limites d’exposition professionnelle (VLEP) dans l’air des lieux de travail ont été établies pour la morpholine.

Prélèvement au travers d’un tube rempli d’un support adsorbant (résine XAD-7 ou polymère poreux Chromosorb P) imprégné par un acide minéral

(phosphorique ou sulfurique). Désorption et traitement par un ou des mélanges d’eau, de méthanol et de soude. Dosage par chromatographie en phase gazeuse

avec détection par ionisation de flamme ou thermoionique [9, 18].

Prélèvement au travers d’un tube rempli de gel de silice. Désorption par un mélange acétonitrile/chlorure de toluoyle en présence de soude ou de potasse.

Dosage par chromatographie en phase liquide avec détection UV [19].

L’utilisation d’un appareil à réponse instantanée équipé d’un tube réactif colorimétrique Gastec (Amines n° 180 ou n° 180L) est possible et permet de mesurer la

morpholine dans une gamme de concentrations [0,5-10 ou 9-180 ppm].

[3, 6, 7]

La morpholine est un liquide inflammable (point d’éclair compris entre 31 °C et 35 °C en coupelle fermée) dont les vapeurs peuvent former des mélanges explosifs avec

l’air.

D’autre part les oxydants puissants peuvent réagir vivement avec le produit.

En cas d’incendie où est impliqué ce produit, les agents d’extinction préconisés sont le dioxyde de carbone, les mousses et les poudres. En général, l’eau en jet direct n’est

pas recommandée car elle peut favoriser la propagation de l’incendie. On pourra toutefois l’utiliser sous forme pulvérisée pour éteindre un feu peu important ou refroidir

les fûts exposés ou ayant été exposés au feu.

En raison de la toxicité des fumées lors de la combustion de la morpholine, les intervenants qualifiés seront équipés d’appareils de protection respiratoire autonomes iso‐

lants et de combinaisons de protection spéciales.

La morpholine est bien absorbée par toutes les voies, distribuée principalement vers le foie et les reins et éliminée essentiellement dans les urines, sous forme

inchangée.

La morpholine est bien absorbée par voies orale, respiratoire et cutanée.

Chez le rat, 2 h après administration orale ou intraveineuse (iv), respectivement 29 ou 19 % des molécules marquées sont dans l’intestin et 26 ou 27 % dans les

muscles.

Chez le lapin, après injection intraveineuse de C-morpholine, les plus fortes concentrations sont retrouvées, après 30 mn, dans les reins, puis les poumons, le foie et

le sang ; la morpholine ne se fixe pas aux protéines sériques. Après exposition par inhalation (905 mg/m pendant 5 h), les plus fortes concentrations sont mesurées

dans les reins et les urines.

La quasi-totalité de la morpholine absorbée est excrétée sous forme inchangée chez le rat, la souris, le hamster et le lapin, quelle que soit la voie d’administration. En

revanche, chez le cobaye, un métabolite urinaire, représentant environ 20 % de la dose administrée par injection intrapéritonéale, a été identifié, le Nméthylmorpholine-N-oxyde ; il résulte d’une N-méthylation de la morpholine suivie d’une N-oxydation.

En présence de nitrites, 0,5 à 12 % de la dose de morpholine est transformé en N-nitrosomorpholine (NMOR), cancérogène, qui est éliminée dans l’urine sous forme

de N-nitroso-(2-hydroxyéthyl)glycine.

L’élimination plasmatique est biphasique chez l’animal (administration intrapéritonéale, ip), avec une demi-vie pour la 1 phase de 115-120 mn chez le rat et le

hamster, et 300 mn chez le cobaye.

La voie majeure d’excrétion est l’urine : 85-88 % d’une dose orale, ip ou iv, chez le rat sont éliminés en 24 h, 5 % supplémentaires dans les 3 jours suivants. Le chien

excrète 70-80 % de la dose par cette voie. La vitesse d’excrétion varie avec l’espèce (quantité éliminée dans les 6 premières heures : hamster > rat > cobaye > lapin) et

le pH (l’excrétion augmente si la molécule est neutralisée avant exposition par addition d’acide).

Chez le rat, 0,5 % de la dose ip est éliminé dans l’air expiré sous forme de CO et 1,7 % dans les fèces

En exposition prolongée, la morpholine est irritante et toxique pour les reins et le foie.

Une exposition prolongée par gavage pendant 30 jours induit, chez le rat (1600-8000 mg/kg/j) et le cobaye (90 450 mg/kg/j), des lésions sévères des tubules rénaux,

une dégénérescence graisseuse du foie et une nécrose de l’épithélium glandulaire de l’estomac.

Par inhalation, des rats exposés à 65 200 mg/m (18 000 ppm), 8 h/j meurent en 5 jours ; ils présentent des hémorragies pulmonaires, des lésions des tubules rénaux

et une dégénérescence graisseuse du foie. Lors d’une exposition prolongée (6 h/j, 5 j/sem, 0-25-100-250 ppm (0-90-360-900 mg/m ), 13 sem ou 0-36-181-543 mg/m ,

104 sem)), seules une perte de poids et une irritation du nez et des yeux sont notées à la plus forte concentration (inflammation de la cornée, inflammation et

métaplasie squameuse de l’épithélium des turbinates et nécrose dans la cavité nasale) chez les rats.

3 3

[10]

L’effet génotoxique de la morpholine est faible in vitro et douteux in vivo ; il augmente en présence de nitrite de sodium.

In vitro, la morpholine n’est pas mutagène pour les bactéries, avec ou sans activateurs métaboliques, ou les levures. Elle augmente légèrement le taux de mutants

dans les cellules de lymphome de souris sans activateur métabolique mais n’induit pas de synthèse non programmée de l’ADN dans les hépatocytes de rat en

culture. Elle est faiblement clastogène (augmentation faible des échanges entre chromatides sœurs) pour les cellules ovariennes de hamster chinois et augmente, à la

condition de ne pas être neutralisée, le nombre de foyers de cellules Balb/3T3 transformées.

In vivo, dans une étude peu documentée, une augmentation du nombre d’aberrations chromosomiques a été observée dans la moelle osseuse du rat et du cobaye

exposés pendant 4 mois à 8 ou 70 mg/m . Chez la souris, la morpholine (600 mg/kg, voie orale) administrée seule, n’augmente pas le taux de lésions de l’ADN (test des

comètes négatif) quel que soit l’organe ; en revanche, en présence de nitrite de sodium (100 mg/kg, voie orale) et de l’acidité du suc gastrique, il y a formation

endogène d’une nitrosamine. Cette dernière serait responsable de l’augmentation des lésions de l’ADN observée au niveau du foie uniquement

La morpholine est classée dans le groupe 3 (agents inclassables quant à leur cancérogénicité pour l’homme) par le CIRC et elle n’est pas classée par l’U.E. Elle n’est pas

cancérogène mais le devient en présence de nitrites.

Par voie orale, la morpholine n’est pas cancérogène pour la souris (env. 900 mg/kg/j dans la nourriture pendant 28 semaines) et le hamster (1000 mg/kg/j sur 1

génération) ; chez le rat (5-50-1000 mg/kg/j pendant toute la durée de la vie sur 2 générations), elle provoque 2 à 3 % de carcinomes hépatiques, d’angiosarcomes

pulmonaires et de gliomes malins.

Par inhalation, elle n’induit pas la formation de tumeurs chez le rat (0-36-181-543 mg/m , 6 h/j, 5 j/sem pendant 104 sem).

En présence d’un mélange morpholine + nitrite de sodium (5 g/kg de chaque dans la nourriture pendant 12 sem), les animaux développent des tumeurs

hépatiques. Il faut rappeler que la N-nitrosomorpholine, formée par la morpholine en présence de nitrite de sodium, est cancérogène par voie orale pour le foie, les

poumons, les reins, et les vaisseaux sanguins chez le rat, la souris et le hamster. Cette molécule peut se trouver sous forme d’impureté dans la morpholine.

Les principaux effets aigus décrits avec la morpholine sont des effets irritants de la peau, des muqueuses nasales et oculaires et des voies

respiratoires. Les effets de l’exposition chronique à la morpholine sont peu documentés ; il s’agit principalement de symptômes

d’irritation oculaire, respiratoire et rhinopharyngée ainsi qu’une vision bleutée décrits lors d’exposition à de fortes concentrations ou

lorsque le produit est chauffé. Dans une étude, il n’a pas été retrouvé d’augmentation significative du nombre d’aberrations

chromosomiques dans les lymphocytes circulants chez des travailleurs exposés à la morpholine. Aucune donnée n’a été publiée

concernant de possibles effets cancérogènes ou reprotoxiques chez l ‘homme.

[2, 3, 6, 14 à 17]

La morpholine est un produit corrosif [16]. En milieu professionnel, les sujets sont principalement exposés par voies cutanée et respiratoire. Le seuil olfactif est de 0,01

ppm ; à 4,4 ppm (soit environ 16 mg/m), la morpholine est perçue comme désagréable [15, 16].

Une exposition volontaire d’un sujet à 12 000 ppm de morpholine (43 000 mg/m , soit 600 fois la Valeur Limite Court Terme (VLCT) de 20 ppm) pendant 1,5 minute a

entraîné une irritation nasale et oculaire suivie de toux [3, 2, 15].

Lors d’exposition professionnelle à la morpholine à des concentrations n’entraînant pas de symptômes d’inconfort (concentration et durée d’exposition non

connues), ont été décrits une vision bleutée avec vue trouble et « halo » autour de la lumière (liés à un œdème cornéen transitoire) apparaissant 30 minutes à 1 heure

après le début de l’exposition, pouvant persister jusque 4 à 6 heures après arrêt de l’exposition [2, 14, 17] ; si l’exposition est plus importante, peuvent s’y associer

des irritations de la peau, des muqueuses nasales et oculaires et des voies respiratoires voire des nausées et des céphalées [2, 17].

Par contact cutané, la morpholine provoque, après un temps de latence de quelques heures, un érythème cutané avec œdème, brûlure et parfois phlyctène ; elle est

encore légèrement irritante en solution diluée à 2 % [2, 6]. Des signes d’intoxication systémique sont possibles à type d’asthénie, tremblements, hypersalivation et lar‐

moiements [14].

Les projections oculaires ou l’exposition à des vapeurs peuvent entraîner des signes d’irritation oculaire intense à type de larmoiements, rougeurs, douleurs

oculaires ; des atteintes graves de la cornée, avec œdème transitoire sont également décrites. Une cécité est possible après une brûlure sévère [3, 6].

[3]

Les effets de l’exposition chronique à la morpholine sont peu documentés. Ce sont principalement des symptômes d’irritations oculaire, respiratoire et

rhinopharyngée ainsi qu’une vision bleutée qui ont été décrits lors d’exposition à de fortes concentrations ou lorsque le produit est chauffé.

[2, 6]

Une étude ne retrouve pas d’augmentation significative du nombre d’aberrations chromosomiques dans les lymphocytes circulants de 24 travailleurs exposés à la

morpholine pendant 3 à 10 ans, comparés à des témoins ; les niveaux d’exposition étaient de l’ordre de 0,54 à 0,93 mg/m 3 [6].

[12, 16]

Aucune donnée n’a été publiée concernant de possibles effets cancérogènes chez l’homme.

À noter cependant que la morpholine peut être transformée en N-nitrosomorpholine au cours du process dans l’industrie du caoutchouc, et qu’un excès de cancers

chez les travailleurs de l’industrie du caoutchouc a été observé avec cette nitrosamine dans une étude (Fajen 1999 cité dans [16]).

Aucune donnée n’a été publiée concernant des effets sur la reproduction chez l’homme

MORPHOLINE (MORFOLN)

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