Morpholine
Morpholine (1,4-tetrahydro-oxazine) is a simple heterocyclic compound with great industrial importance and a wide range of applications.
Morpholine is typically used as follows: rubber chemicals, 40%; corrosion inhibitors, 30%; waxes and polishes, 5%; optical brighteners, 5%; and miscellaneous, 20%
Morpholine and its derivatives have been used as rubber additives, corrosion inhibitors, solvents, optical brighteners, antioxidants, and in manufacturing a range of drugs and herbicides.
Morpholine is an essential building block for rubber chemicals and has many applications in other industries.
Morpholine is a common additive, in parts per million concentrations, for pH adjustment in fossil fuel and power plant steam systems.
Morpholine is a copper, iron, lead, zinc, and other metals corrosion inhibitor.
Morpholine is widely used in automobiles, mechanical instruments, and medical equipment.
In its gas-liquid state, Morpholine has lower toxicity towards the environment when compared to its forerunners like cyclohexylamine and dicyclohexylamine nitrite.
Morpholine is used as an intermediate chemical for water treatment, the production of pharmaceutical and agricultural products, and optical brighteners.
Morpholine is used in the following products: adhesives and sealants, coating products, inks and toners, anti-freeze products, biocides (e.g., disinfectants, pest control products), fuels, photo-chemicals, polishes and waxes, washing & cleaning products and paper chemicals and dyes.
Morpholine and derivatives may be used as an accelerator/catalyst in epoxy formulations or as catalyst/initiator in UV-curable acrylic-based systems for coatings and adhesives.
Morpholine is extensively used in the pharmaceutical industry as a building block for synthesizing various drugs, such as antibiotics, anticoagulants, and antidepressants. The growing demand for these drugs is expected to fuel the demand for morpholine.
Morpholine is an intermediate in producing various agrochemicals, such as herbicides, fungicides, and insecticides.
Morpholine is used as a corrosion inhibitor in water treatment plants, which helps prevent the corrosion of metal pipes and equipment.
With the growing demand for clean and safe water, the demand for morpholine in the water treatment industry is expected to increase in the forthcoming years.
Morpholine is used as a solvent and emulsifying agent in producing various personal care products, such as lotions, shampoos, and conditioners.
Morpholine manufactures paper, glass, soap, detergent, dye, and synthetic fiber.
Morpholine is used to manufacture analysis reagents for nitrogen determination.
Morpholine also finds applications in pharmaceuticals, tanning, textiles, household care, and ceramics industries.
Morpholine is commonly used as a chemical intermediate in corrosion inhibitors and steam boiler systems.
Applications of Morpholine also include; pharmaceuticals, textiles, rubber, catalysts, plasticizers, dyes, and agricultural and photographic chemicals.
Substance identity of Morpholine:
CAS no.: 110-91-8
EC / List no.: 203-815-1
Mol. formula: C4H9NO
Properties
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)[3]
Acidity (pKa): 8.36[4] (of conjugate acid)
Magnetic susceptibility (χ): -55.0·10−6 cm3/mol
SYNONYMS OF MORPHOLINE:
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
BASF 238
Diethylene imidoxide
Diethylene oximide
Diethylenimide oxide
Drewamine
Morpholin
Morpholine (8CI, 9CI)
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
APPLICATION OF MORPHOLINE IN WATER TREATMENT:
Morpholine is an organic amine used for boiler water treatment.
Morpholine increases the pH of boiler water to protect the boiler against corrosion.
Morpholine is an amine and does not add salt to the boiler water and thereby does not increase the TDS, which results in reduced blow down and fuel savings.
MORPHOLINE can be used in all types, sizes, and pressure of boilers.)
Key Features and Benefits
Prevents stress cracking corrosion
Does not add TDS
Reduces blow-down requirement
Saves power
Compatible with other treatment chemicals
Returns to the feed line with the condensate return so raise the feed water pH
Industrial applications of Morpholine:
Morpholine is used because its volatility is about the same as water.
Once added to the water, its concentration becomes distributed relatively evenly in both the water and steam phases.
Morpholine’s pH-adjusting qualities are distributed throughout the steam plant to protect corrosion.
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 slowly without oxygen at these steam systems’ high temperatures and pressures.
Organic synthesis
Morpholine undergoes most chemical reactions typical for other secondary amines. However, 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 preparing the antibiotic linezolid, the anticancer agent gefitinib (Iressa), and the analgesic dextromoramide.
In research and industry, morpholine’s low cost and polarity lead to its everyday use as a solvent for chemical reactions.
Rubber chemicals
Morpholine is an essential intermediate for rubber-processing chemicals, especially in the production of delayed-action rubber accelerators, which are added during the vulcanization process to reduce the possibility of pre-vulcanization during the mixing stages fabrication.
Morpholine-derived sulfur compounds give a high cure rate during vulcanization, with a reduced tendency to over-cure.
These include morpholinium N, N-oxydiethylenedithiocarbamate and 2-(N-morpholinothio)benzothiazole.
Morpholine derivatives, such as N, N1-dithiodimorpholine and N, N′-tetrathiodimorpholine, are also used to stabilize halogenated butyl rubber against heat-aging effects.
(ii) Corrosion control
Morpholine is used to control corrosion in condensate steam systems.
Morpholine neutralizes carbon dioxide and other corrosive acid components in steam and condensate, aids in maintaining the proper pH throughout the system, has a suitable vapor pressure and aqueous solubility, and is stable at temperatures up to 288°C.
Morpholine and its salts with fatty acids from animal and vegetable oils may be used as corrosion inhibitors for steel or tin plate to be used in contact with food.
Morpholine has been used as a corrosion inhibitor in the natural gas and pipeline industry.
(iii) Waxes and polishes
Morpholine reacts readily with fatty acids, forming emulsifying agents used to formulate water-resistant waxes and polishes for automobiles, floors, leather, and furniture.
As the film of polish emulsion gradually dries, morpholine evaporates to form a film highly resistant to water spotting and deterioration.
An example of this type of polish is a carnauba wax formulation with the following composition (in parts by weight): carnauba wax, 11.2; oleic acid, 2.4; morpholine, 2.2; water, 67.0.
A typical silicone automobile polish-cleaner is composed as follows (in parts by weight): silicone fluid, 4.0; oleic acid, 2.5; morpholine, 1.5; Stoddard solvent (see the monograph on some petroleum solvents, p. ), 19; kerosene (deodorized), 2; water, 57; abrasive, 14.
The following formulation is representative of silicone-containing furniture polishes (in parts by weight): silicone fluid, 5.0; VM & P naphtha (see the monograph on some petroleum solvents, p. 43) (high flash), 30.0; oleic acid, 2.5; morpholine, 1.5; water, 60.6; water-soluble resin, 0.4 (Dow Chemical Co., 1985).
(iv) Optical brighteners
Morpholine is an essential intermediate in the manufacture of optical brighteners.
The diamino stilbene triazine type brightener with morpholine as a substituent on one of the triazine rings is used in home laundry detergents since it is stable to chlorine bleaches.
(v) Miscellaneous
Morpholine and its salts have been reported to be used as components of protective coatings applied on fruits and vegetables.
Morpholine has been used in preparing pharmaceuticals, including such diverse products as analgesics, local anesthetics, respiratory and circulatory stimulants, antispasmodics, and soluble sulfanilamides.
Morpholine derivatives have been used widely in the textile industry as softening agents for cellulosic fibers, ingredients of rayon spinning baths, sizing emulsifiers, textile lubricants, whitening agents, and dyes.
Cosmetic products that may incorporate morpholine-based compounds include hair conditioners, deodorants, shampoos, mouthwashes, and cosmetic creams.
Stabilizers and antioxidants for lubricating oils, soluble oils for cutting tools, and carbon remover compounds have been prepared from morpholine.
Morpholine has a high selectivity and solvency for aromatics and can be used to extract benzene and xylene economically from petroleum feedstock. Other products synthesized from morpholine include ion-exchange resins, dyes for electrolytic recording inks, and photographic chemicals.
Synonyms: Diethylenimide Oxide, 1,4-oxazinane, tetrahydro-1,4-oxazine, Diethylene imidoxide, Diethylene oximide, Tetrahydro-p-oxazine, Morpholin.
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
Translated names of Morpholine:
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)
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
Morpholine
morpholine
MORPHOLINE-2,2,3,3,5,5,6,6-D8 (D, 98%)
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
Morpholin
Morpholine (8CI, 9CI)
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
ALTERNATIVE CHEMICAL NAMES:
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
OTHER PRODUCTS OF ATAMAN CHEMICALS THAT MIGHT BE OF INTEREST:
AEP
Aminoethylpiperazine
Aminopropylmorpholine
APDEA
APM
APMMEA
APMMEA-WB
CYCLOALIPHATIC AMINE
DETA
Diethylenetriamine
Dimethylaminopropylamine
Dimethylethanolamine
DMAPA
DMDPTA
DMEA
ECA-29
EDA
Ethylene carbonate
Ethylenediamine
Glycerine carbonate
Higher reactivity polyether diamine
Higher reactivity PTMEG based triamine
JEFFADD HEEU additive
JEFFADD series
JEFFAMINE D-2000 amine
JEFFAMINE D-205 amine
JEFFAMINE D-230 amine
JEFFAMINE D-400 amine
JEFFAMINE D-4000 amine
JEFFAMINE ED-2003 amine
JEFFAMINE ED-600 amine
JEFFAMINE ED-900 amine
JEFFAMINE EDR-148 amine
JEFFAMINE EDR-series
JEFFAMINE ED-series
JEFFAMINE M-1000 amine
JEFFAMINE M-2005 amine
JEFFAMINE M-2070 amine
JEFFAMINE M-600 amine
JEFFAMINE M-series
JEFFAMINE RFD-270 amine
JEFFAMINE T-3000 amine
JEFFAMINE T-403 amine
JEFFAMINE T-5000 amine
JEFFAMINE THF-100 amine
JEFFAMINE THF-170 amine
JEFFAMINE THF-series
JEFFAMINE T-series
MDEA
Methoxypropylamine
MMEA
Monomethylethanolamine
MOPA
MORPHOLINE
Morpholine
N-(2-Hydroxyethyl)ethylene urea
N, N-dimethyldipropylenetriamine
N-aminopropyldiethanolamine
N-aminopropylmonomethylethanolamine
N-aminopropylmonomethylethanolamine*
NEM
N-ethylmorpholine
N-methyldiethanolamine
N-methylmorpholine
NMM
PEG/PPG copolymer based diamine
PEG/PPG copolymer based diamine
PEG/PPG copolymer based diamine
Polyamine mixture
Polyetheramine
Polyoxypropylene diamine
Polyoxypropylene diamine
Polyoxypropylene diamine
Polyoxypropylene monoamine
Polyoxypropylene monoamine
Polyoxypropylene monoamine
Polyoxypropylene monoamine
Polyoxypropylene triamine
Polyoxypropylene triamine
Polyoxypropylene triamine
Propylene carbonate
PTMEG/PPG copolymer based diamine
Slow reactivity aliphatic polyether diamine
TEPA
TETA
Tetraethylenepentamine
Triethylenetetramine
Alkyl Alkanol Amines[-]
Methyl Monoethanolamine (MMEA)
Methyl Diethanolamine (MDEA)
Di – Methyl Ethanolamine* (DMEA)
Di- Ethyl Ethanolamine (DEEA)
Ethyl Monoethanolamine (EMEA)
Ethyl Diethanolamine (EDEA)
Mono-n-propyl Monoethanolamine (PMEA)
Mono-n-propyl Diethanolamine (PDEA)
Mono-n-Butyl Ethanolamine (BMEA)
Mono-n-Butyl Diethanolamine (BDEA)
Di-Butyl Ethanolamine (DBEA)
Poly Ethanolamine (PEA)
Tertiary Butyl Monoethanolamine (TBMEA)
Tertiary Butyl Diethanolamine (TBDEA)
Alkanolamines[-]
Triisopropanolamine-85% (TIPA 85%)
Monoethanolamine (MEA)
Diethanolamine (DEA)
Triethanolamine-Tech (TEA-85% min)
Triethanolamine-pure (TEA-99%)
Diethanolamine LFG (DEA-85%)
Morpholine & Substituted
Morpholines[-]
Morpholine
N-Methyl Morpholine (NMM)
N-Methyl Morpholine Oxide 50% (NMMO)
N-Ethyl Morpholine (NEM)
N-Formyl Morpholine (NFM)
Hydroxy Ethyl Morpholine (HEM)
N-Acetyl Morpholine (NAM)
N-Butyl Morpholine (NBM)
Specialty E.O./P.O. Products[-]
2-Phenoxy Ethanol
1-Piperidine Ethanol (2-Piperidino Ethanol)
Diethanol Isopropanolamine 85% DEIPA 85%)
N-2 Hydroxy Ethyl Pyrrolidine
N-Benzyl Ethanolamine (NBzEA)
E.O./P.O. Derivatives[-]
Polypropylene Glycol 200/400/600/800/4000/5000
Polyethylene glycol 425/900/2020/4000
APOL-61/62/64/68
Amines POLYOLS
Glycerol Polyol
Polyethylene glycol Adipates
Sorbitol mixture Ethoxylates
Alcohol Ethoxylates