EPICHLOROHYDRIN (EPKLOROHDRN)
Epichlorohydrine (Epiklorohidrin)
CAS NO:106-89-8
EC NO:203-439-8
Synonyms:
Epiklorohidirin; Epiklorohidrine; epichlorohydrine; Epichlorohydrine;Epiklorohidrin ; Epiklorohidrine; Epiclorohidrin; epichlorohydrin; Epichlorohydrin; Epiklorohidrine; Epiclorohidrine; Epichlorohidrin ; Epichlorohidrine ; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; Epiklorohidrin; Epiklorohidrine ;2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; 1-Chloro-2,3-epoxypropane; epichlorohydrine; Glycidyl chloride;Oxirane, epichlorohydrine; (chloromethyl)-1,2-Epoxy-3-chloropropane;2,3-Epoxypropyl chloride; 3-Chloropropylene oxide;Chloropropylene oxide; epichlorohydrine; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; Epichlorhydrin;106-89-8; epichlorohydrine; Epichlorhydrin;106-89-8; epichlorohydrine; 3 epichlorohydrine; -Chloro-1,2-epoxypropane;Chloromethyloxirane;Epichlorhydrine;Epicloridrina;Glycerol epichlorohydrin;Epichloorhydrine; Epichlorohydryna(CHLOROMETHYL)OXIRANE; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; Glycerol epichlorhydrin; epichlorohydrine; 3-Chloro-1,2-propylene oxide;(Chloromethyl)ethylene oxide;SKEKhG;alpha-Epichlorohydrin ; Epichlorophydrin; epichlorohydrine; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; epichlorohydrine; Oxirane, 2-(chloromethyl); epichlorohydrine; 3-Chloropropene-1,2-oxide;Propane, 1-chloro-2,3-epoxy-1-Chlor-2,3-epoxy-propan;1-Cloro-2,3-epossipropano ; epi-Chlorohydrin; epichlorohydrine; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin ; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; 1-Chloor-2,3-epoxy-propaan; epichlorohydrine; Rcra waste number U041;Epoxypropyl chloride;gamma-Chloropropylene oxide;Caswell No. 424.alpha.-Epichlorohydrin;Epicloridrina [Italian]; epichlorohydrine; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPKLOROHDRN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin;106-89-8; epichlorohydrine; Epichloorhydrine [Dutch];Epichlorhydrine [French];Epichlorohydryna [Polish];NSC 6747;Alyl chloride oxide.gamma.-Chloropropylene oxide;CCRIS 277 ;HSDB 39;Allyl epichlorohydrine; chloride oxide;(DL)-.alpha.-Epichlorohydrin;DL-a-Epichlorohydrin;Epoxy-3-chloropropane;(chloromethyl)-Oxirane;2-Chloromethyl-oxirane;(+/-)-2-(Chloromethyl)oxirane ;NCI-C07001(RS)-3-chloro-1,2-epoxypropane;Oxirane, epichlorohydrine; (chloromethyl)-;(+/-)-Epichlorohydrin;EINECS 203-439-8;UN2023;1-Chlor-2,3-epoxy-propan [German];RCRA waste no. U041 ; epichlorohydrine; 1-Chloor-2,3-epoxy-propaan epichlorohydrine; epichlorohydrine; [Dutch]; epichlorohydrine; 1-Cloro-2,3-epossipropano [Italian];EPA Pesticide Chemical Code 097201;BRN 0079785;oxirane, 2-(chloromethyl)-;(chloromethyl) Ethylene oxide ;epichlorohydrine; AI3-03545;CHEBI:37144;BRLQWZUYTZBJKN-UHFFFAOYSA-N;NCGC00091792-01;DSSTox_CID_566;Epichlorohydrin, >=99%;Epichlorohydrin-2-13C;DSSTox_RID_75662;DSSTox_GSID_20566;;13403-37-7 ;56227-39-5;ECH;Polidexide; epichlorohydrine; epichlorohydrine; Oxirane, (chloromethyl)-, (R)-;Polidexidi sulfas;9009-12-5CAS-106-89-8;C3H5ClO;Sulfate de polidexide;Sulfato de polidexido;5-17-01-00020 (Beilstein Handbook Reference) ; epichlorohydrine; CCRIS 6387; epichlorohydrine; Chloropropylene; epichlorohydrine; Polidexidi sulfas [INN-Latin];BRN 1420785;Chloropropyl epoxide;Sulfate de polidexide [INN-French];Sulfato de polidexido [INN-Spanish];2-chloromethyloxirane ; epichlorohydrine; -Epichlorohydrin;chloromethyl) Oxirane; epichlorohydrine; Cardolite NC-513;3-Chloropropyl epoxide;beta-epoxypropylchloride;Epichlorohydrin, 99%;Epoxy-3-chlor opropane;AC1L1PNR;AC1Q3UAD;; epichlorohydrine; epichlorohydrine; 3-Chloro-propylene oxide; epichlorohydrine; epichlorohydrine; Chloro-1,2-epoxypropan;eChloro-2,3-epoxypropane;Chloropropene-1,2-oxide;2-(chloromethyl)-oxirane;3-Chloropro pylene Oxide;2-(chloromethyl) Oxirane; ;epichlorohydrine; bmse000722;UNII-61TTR6T3SE; epichlorohydrine; epichlorohydrine; epichlorohydrine; WLN: T3OTJ B1G;(RS)-(chloromethyl)oxirane;3-chloro-1,2-epoxypropene;61TTR6T3SE;Chloro-1,2-propylene oxide;Epichlorohydrin Reagent Grade;1-chloro-2,3-epoxy-propane; epichlorohydrine; 1-Chloro-2,3-epoxy propone; epichlorohydrine; ( )-2-(Chloromethyl)oxirane;CHEMBL1421613;DTXSID1020566;CTK5A4812;NSC6747;MolPort-001-779-799;BB_SC-6806;NSC-6747; Tox21_111167; Tox21_200276 ; 6660AH; AR-1I7145; BBL012223; LS-409;MFCD00005132; epichlorohydrine; STL163564;Epichlorohydrin [UN2023] [Poison];AKOS000118974; epichlorohydrine; AKOS016039400;Epichlorohydrin [UN2023] [Poison];MCULE-9759519789;RP18559 ;TRA0067700;UN 2023;(+/-)-Epichlorohydrin, 99% 100g;NCGC00091792-02;NCGC00091792-03; NCGC00257830-01; BP-31004; epichlorohydrine; HE027244; HE293532; epichlorohydrine; HE315376;HE379166;KB-50544;SC-47193;(+/-)-Epichlorohydrin, analytical standard; KB-309491;LS-101030;TL8003414;E0012;FT-0625672;(+/-)-Epichlorohydrin, purum, >=99% (GC);5717-EP2269977A2; epichlorohydrine; Epichlorohydrine;Epiklorohidrin ; Epiklorohidrine; Epiclorohidrin; epichlorohydrin; Epichlorohydrin; Epiklorohidrine; Epiclorohidrine; Epichlorohidrin ; Epichlorohidrine ; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPKLORHDRN; epichlorohydrine; EPIKLORHIDRIN; Epiklorohidrin
Epichlorohydrine
Epichlorohydrin
(±)-Epichlorohydrin[1]
Epichlorohydrin skeletal structure
R-Epichlorohydrin-calculated-MP2-3D-balls.png
(R)-Epichlorohydrin
S-Epichlorohydrin-calculated-MP2-3D-balls.png
(S)-Epichlorohydrin
Names
Preferred IUPAC name
2-(Chloromethyl)oxirane
Other names
(Chloromethyl)oxirane
Epichlorohydrin
1-Chloro-2,3-epoxypropane
γ-Chloropropylene oxide
Glycidyl chloride
Identifiers
CAS Number
106-89-8 ☑
3D model (JSmol)
Interactive image
Beilstein Reference 79785
ChEBI
CHEBI:37144 ☑
ChEMBL
ChEMBL1421613
ChemSpider
13837112 ☑
ECHA InfoCard 100.003.128 Edit this at Wikidata
EC Number
203-439-8
Gmelin Reference 164180
KEGG
C14449 ☑
PubChem CID
7835
RTECS number
TX4900000
UNII
08OOR508C0 ☑
UN number 2023
CompTox Dashboard (EPA)
DTXSID1020566 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula C3H5ClO
Molar mass 92.52 g/mol
Appearance colorless liquid
Odor garlic or chloroform-like
Density 1.1812 g/cm3
Melting point -25.6 °C (-14.1 °F; 247.6 K)
Boiling point 117.9 °C (244.2 °F; 391.0 K)
Solubility in water 7% (20°C)[2]
Vapor pressure 13 mmHg (20°C)[2]
Hazards
Safety data sheet External MSDS
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
GHS hazard statements H226, H301, H311, H314, H317, H331, H350
GHS precautionary statements P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P281, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P308+313, P310, P311
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
332
Flash point 32 °C (90 °F; 305 K)
Explosive limits 3.8-21%[2]
Lethal dose or concentration (LD, LC):
LC50 (median concentration) 3617 ppm (rat, 1 hr)
2165 ppm (rat, 1 hr)
250 ppm (rat, 8 hr)
244 ppm (rat, 8 hr)
360 ppm (rat, 6 hr)[3]
LCLo (lowest published) 250 ppm (rat, 4 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible) TWA 5 ppm (19 mg/m3) [skin][2]
REL (Recommended) Carcinogen[2]
IDLH (Immediate danger) Ca [75 ppm][2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents.[4] It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.
Production
Epichlorohydrin is traditionally manufactured from allyl chloride in two steps, beginning with the addition of hypochlorous acid, which affords a mixture of two isomeric alcohols:[5][6]
Epichlorohydrin-manufacture-step1-2D-skeletal.png
In the second step, this mixture is treated with base to give the epoxide:
Epichlorohydrin-manufacture-step2-2D-skeletal.png
In this way, more than 800,000 tons (1997) of epichlorohydrin are produced annually.[7]
Glycerol routes
Epichlorohydrin was first described in 1848 by Marcellin Berthelot. The compound was isolated during studies on reactions between glycerol and gaseous hydrogen chloride.[8]
Reminiscent of Berthelot’s experiment, glycerol-to-epichlorohydrin (GTE) plants have been commercialized. This technology capitalizes on the availability of cheap glycerol from biofuels processing.[9] In the process developed by Dow Chemical, glycerol undergoes two substitution reactions when treated with hydrogen chloride in the presence of a carboxylic acid catalyst. This is the same intermediate formed in the allyl chloride/hypochlorous acid process, and is likewise then treated with base to form epichlorohydrin.[10]
GTE-Prozess.svg
Other routes
Routes that involve fewer chlorinated intermediates have continued to attract interest. One such process entails epoxidation of allyl chloride.[11]
Applications
Glycerol and epoxy resins synthesis
Epichlorohydrin is mainly converted to bisphenol A diglycidyl ether, a building block in the manufacture of epoxy resins.[12] It is also a precursor to monomers for other resins and polymers. Another usage is the conversion to synthetic glycerol. However, the rapid increase in biodiesel production, where glycerol is a waste product, has led to a glut of glycerol on the market, rendering this process uneconomical. Synthetic glycerol is now used only in sensitive pharmaceutical, and biotech applications where quality standards are very high.[13]
Minor and niche applications
Epichlorohydrin is a versatile precursor in the synthesis of many organic compounds. For example, it is converted to glycidyl nitrate, an energetic binder used in explosive and propellant compositions.[14] The epichlorohydrin is reacted with an alkali nitrate, such as sodium nitrate, producing glycidyl nitrate and alkali chloride. It is used as a solvent for cellulose, resins, and paints, and it has found use as an insect fumigant.[15]
Polymers made from epichlorohydrin, e.g., polyamide-epichlorohydrin resins, are used in paper reinforcement and in the food industry to manufacture tea bags, coffee filters, and sausage/salami casings as well as with water purification.[16]
An important biochemical application of epichlorohydrin is its use as crosslinking agent for the production of Sephadex size-exclusion chromatographic resins from dextrans.[17]
Safety
Epichlorohydrin is classified by several international health research agencies and groups as a probable or likely carcinogen in humans.[18][19][20] Prolonged oral consumption of high levels of epichlorohydrin could result in stomach problems and an increased risk of cancer.[21] Occupational exposure to epichlorohydrin via inhalation could result in lung irritation and an increased risk of lung cancer
Epichlorohydrin is a volatile and flammable, clear, colorless, liquid, chlorinated cyclic ether with an irritating, chloroform-like odor that emits toxic fumes of hydrochloric acid and other chlorinated compounds when heated to decomposition. Epichlorohydrin is used in the manufacture of epoxy resins, synthetic glycerin and elastomers. Exposure to epichlorohydrin irritates the eyes, skin and respiratory tract, and can cause chemical pneumonitis, pulmonary edema, and renal lesions. This substance also affects the blood. Epichlorohydrin is reasonably anticipated to be a human carcinogen and may be associated with an increased risk of developing respiratory cancer. (NCI05)
NCI Thesaurus (NCIt)
Epichlorohydrin is an epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine. It is an organochlorine compound and an epoxide. It derives from a 1,2-epoxypropane.
ChEBI
(Chloromethyl)oxirane, also known as alpha-epichlorohydrin or 1-chloro-2, 3-epoxypropane, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms) (Chloromethyl)oxirane exists as a liquid, soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, (chloromethyl)oxirane is primarily located in the cytoplasm (Chloromethyl)oxirane can be biosynthesized from 1, 2-epoxypropane.
Epichlorohydrin is a chlorinated epoxy compound used as an industrial solvent.EPICHLOROHYDRIN is a strong skin irritant and carcinogen.
(Chloromethyl)oxirane is used for cross-linking dextrose units in food starch (Chloromethyl)oxirane belongs to the family of Epoxides.
These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).Molecular Formula of EPICHLOROHYDRIN is C3H5ClO.
Epichlorohydrin is mainly used in the production of epoxy resins. Acute (short-term) inhalation exposure to epichlorohydrin in the workplace has caused irritation to the eyes, respiratory tract, and skin of workers.
At high levels of exposure, nausea, vomiting, cough, labored breathing, inflammation of the lung, pulmonary edema, and renal lesions may be observed in humans.
Chronic (long-term) occupational exposure of humans to epichlorohydrin in air is associated with high levels of respiratory tract illness and hematological effects.
Damage to the nasal passages, respiratory tract and kidneys have been observed in rodents exposed to epichlorohydrin by inhalation for acute or chronic duration. An increased incidence of tumors of the nasal cavity has been observed in rats exposed by inhalation.
EPA has classified epichlorohydrin as a Group B2, probable human carcinogen.
EPICHLOROHYDRIN is a clear colorless liquid with an irritating chloroform-like odor. Density 9.8 lb / gal. Flash point 87°F. Polymerizable. If polymerization takes place inside a closed container,
the container is subject to violent rupture. Irritates the skin and respiratory system. Toxic by ingestion. A confirmed carcinogen. Vapors heavier than air. Used to make plastics and as a solvent.
Colorless liquid with a slightly irritating, chloroform-like odor.Epichlorohydrin is colorless liquid.Odor of Epichlorohydrin is sweet, pungent or chloroform-like … generally perceived as a slightly irritating chloroform like odor.
Boiling Point of Epichlorohydrin is 241.7° F at 760 mm Hg.Melting Point of Epichlorohydrin -54.4 to -14.1° F.Flash Point of Epichlorohydrin 93° F and solubility
50 to 100 mg/mL at 72° F.Density of Epichlorohydrin 1.18 to 1.801 at 68° F.Epichlorohydrin can be oxidized by free radical process in liquid or gas phases; these reactions may occur as photochemically initiated atmospheric reactions.
The primary use of epichlorohydrin is in the production of epoxy resins used in coatings, adhesives, and plastics.
Epichlorohydrin is also used in the manufacture of synthetic glycerine, textiles, paper, inks and dyes, solvents, surfactants, and pharmaceuticals.
Epichlorohydrin is also listed as an inert ingredient in commercial pesticides.Industry Uses of Epichlorohydrin are adhesives and sealant chemicals,intermediates,solvents (which become part of product formulation or mixture).
Consumer Uses of Epichlorohydrin are Adhesives and Sealants,Paints and Coatings.
Unless ksi is specified, data are provided for the materials, standard condition (100 kPa at 25 ° C [77 ° F]).
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Information box resources
Epichlorohydrin (abbreviated ECH) is an organic chlorine compound, an epoxide. Despite its name, this is not halohydrin. This is moderately water-soluble, but most polar organic solvents that can be mixed with a sharp, garlic-like smell, colorless liquid. This is a chiral, usually like, racemic mixture of the current molecule enantiomers between the right hand and left hand. Epichlorohydrin is highly reactive electrophilic compound and glycerol, plastic, epoxy adhesives and resins and elastomers used in its production.
Synthesis of glycerol and epoxy resins
Epichlorohydrin is mainly converted bisphenol A diglycidyl ether, epoxy resins a building block in its manufacture. It is also the precursor to monomers for other resins and polymers. Another use is glycerol, a synthetic transformation. However, the rapid increase in biodiesel is a waste product of glycerol production, this process has led to an excess of glycerol in the non-economical rendering market. Synthetic glycerol is now used only in sensitive medicines and is in the case of biotechnology applications if the quality standards are too high.
Minor and niche applications
Epichlorohydrin is a versatile precursor to the synthesis of many organic compounds. For example, converted nitrate glycidyl, energetic binder used in explosive and propellant gas compositions. It is reacted with an alkali nitrate such as epichlorohydrin, producing sodium nitrate glycidyl nitrate and alkaline chloride. For this, cellulose, resins and dyes used as solvent have found use as an insect fumigant.
Polymers produced from epichlorohydrin, for example, paper reinforcement for the manufacture of polyamide-epichlorohydrin resins and water purification, such as tea bags, coffee filters, and sausage / salami casings used in the food industry.
The important biochemical application of epichlorohydrin is dextrans use as a crosslinking agent for the production of Sephadex size exclusion chromatography resins.
Safety
Epichloride is classified as possible or possible carcinogen in humans by many international health research institutions and groups. Long-term consumption of high levels of epichlorohydrin can lead to increased stomach risk and cancer risk. Occupational exposure to epichlorohydrin through inhalation may lead to increased risk of lung irritation and lung cancer.
Epichlorohydrin is a chlorinated epoxy component used as an industrial solvent. Epichlorohydrin is skin irritant and carcinogenic.
(Chloromethyl) oxirane is used for crosslinking dextrose units of the Epoxides family of oxyran in food starch (Chloromethyl).
These are compounds containing three ring atoms (one oxygen and two carbon atoms) a ringed ether. The molecular formula of epichlorohydrin is C3H5ClO.
Epichlorohydrin is mainly used in the production of epoxy resins. Acute (short-term) respiratory exposure to epichlorohydrin at the workplace caused irritation of the eyes, respiratory tract and workers’ skin.
In case of high exposure, people may experience nausea, vomiting, cough, lactating breathing, inflammation of the lungs, pulmonary edema and renal lesions.
Exposure to Epichlorohydrin in people in the air is associated with chronic (long-term) occupational exposure, high levels of respiratory diseases and hematological effects.
In rodents administered Epichlorohydrin by inhalation for acute or chronic periods, nasal passages, respiratory tract and kidneys were damaged. An increase in the rate of tumor of the nasal cavity was observed in inhaled rats.
EPA has classified Epichlorohydrin as a possible human carcinogen, Group B2.
Epichlorohydrin is a clear colorless liquid with a clear chloroform-like odor. Density 9.8 lb / gal. The flash point is 87 ° F. It can be polymerized. If polymerization takes place in a closed container,
The container is subject to severe tearing. Irritating to skin and respiratory system. Toxic when swallowed. Carcinogen detected. Used in plastic making and as a solvent.
Epichlorohydrin is a colorless liquid with a slightly irritant and chloroform-like odor. It can be oxidized by flux free radical treatment of epichlorohydrin. These reactions can occur in the form of photochemically initiated atmospheric reactions.
The primary use of epichlorohydrin is used in the production of epoxy resins used in coatings, adhesives and plastics.
Epichlorohydrin is also used in the production of synthetic glycerin, textiles, paper, inks and dyes, solvents, surfactants and pharmaceutical products.
Epichlorohydrin is listed as an inert ingredient in commercial insecticide. The use of Epichlorohydrin in the industry are adhesives and sealant chemicals, intermediates, solvents (part of the product formulation or mixture).).
Consumer uses of epichlorohydrin are adhesives and sealants, paints and coatings.
Epichlorohydrin is a volatile and flammable, clear, colorless, liquid, chlorinated cyclic ether with an irritating, chloroform-like odor that emits toxic fumes of hydrochloric acid and
other chlorinated compounds when heated to decomposition. Epichlorohydrin is used in the manufacture of epoxy resins, synthetic glycerin and elastomers. Exposure to epichlorohydrin
irritates the eyes, skin and respiratory tract, and can cause chemical pneumonitis, pulmonary edema, and renal lesions
Epichlorohydrin (chloromethyloxirane) is an organic substance , a chloro derivative of propylene oxide, with the formula CH 2 (O) CH-CH 2 Cl. It is widely used in organic synthesis,
used in the production of epoxy resins and glycerin. Highly toxic, irritant.
Epichlorohydrin is an epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine. It is an organochlorine compound and an epoxide. It derives from
a 1,2-epoxypropane.
(Chloromethyl)oxirane, also known as alpha-epichlorohydrin or 1-chloro-2, 3-epoxypropane, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms) (Chloromethyl)oxirane exists as a liquid, soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, (chloromethyl)oxirane is primarily located in the cytoplasm (Chloromethyl)oxirane can be biosynthesized from 1, 2-epoxypropane.
Preferred IUPAC name
2-(Chloromethyl)oxirane
Other names
(Chloromethyl)oxirane
Epichlorohydrin
1-Chloro-2,3-epoxypropane
γ-Chloropropylene oxide
Glycidyl chloride
Physical properties
It is a colorless mobile transparent liquid with an irritating odor of chloroform , poorly soluble in water , well in most organic solvents. Forms an azeotropic mixture with water with a boiling point of +88 ° C and contains 75% epichlorohydrin. Forms azeotropic mixtures with a large number of organic liquids. Epichlorohydrin is optically active due to the presence of an asymmetric carbon atom [4] .
Chemical properties
Epichlorohydrin is a chemically highly reactive compound with an active epoxy group and a mobile chlorine atom [5] .
Halogenation reaction
When chlorine interacts with epichlorohydrin under normal conditions, 3,3-dichloropropylene oxide (3,3-dichloroepoxypropylene) is formed [5] :
Hydrochlorination reaction
Easily adds hydrogen chloride at ordinary temperature both in solution and in anhydrous medium, with the formation of 1,3-dichlorohydrin [5] :
Dehydrochlorination reaction
In the presence of small amounts of alkali, epichlorohydrin easily attaches compounds containing one or more mobile hydrogen atoms to form chlorohydrins :
With an increase in the alkali concentration, the reaction proceeds with the elimination of hydrogen chloride and the reduction of the epoxy group, but in a different position :
Hydrolysis reaction
With an excess of alkali ( sodium carbonate is most often used ) and at a temperature of 100 ° C, epichlorohydrin is slowly converted into glycerin
Hydration reaction
in the presence of dilute inorganic acids ( sulfuric or orthophosphoric ), epichlorohydrin forms glycerol α-monochlorohydrin
As the temperature rises, the hydration of epichlorohydrin increases.
Esterification reaction
When epichlorohydrin interacts with alcohols , the epoxy ring opens with the formation of a hydroxyl group in position 2 and with the formation of an ether
Amination reaction
Epichlorohydrin already at ordinary temperature adds ammonia or amines with ring opening
Epichlorohydrin reacts with diphenylolpropane to form a polymeric diglycidal ether
Diglycidether
This reaction is an example of the production of epoxy resins , which have recently become very widespread due to their exceptional properties
Polymerization reaction
Epichlorohydrin is capable of polymerizing. Depending on the catalyst used, mobile liquids, high-viscosity oils or resin-like products are obtained
Application
It is used as an intermediate for the synthesis of glycerin derivatives , dyes and surfactants ; for the production of synthetic materials (mainly epoxy resins ).
Toxicology and safety
The general nature of the action
It has an irritating and allergic effect. In experiments on animals, it selectively affects the kidneys. Penetrates the skin .
Epichlorohydrin is a highly toxic and flammable compound . Epichlorohydrin vapors, when inhaled, even in small concentrations, cause nausea , dizziness and lacrimation , and with
prolonged exposure lead to more serious consequences (often severe pulmonary edema occurs ). Epichlorohydrin on contact with the skin and prolonged contact causes dermatitis,
(±) -Epichlorohydrin
Skeletal structure of epichloride
R-Epichlorohydrin calculated-MP2-3D-balls.png
(R) -Epichlorohydrin
S-Epichlorohydrin calculated-MP2-3D-balls.png
(S) -Epichlorohydrin
names
Preferred IUPAC name
2- (Chloromethyl) oxirane
Other names
(Chloromethyl) oxirane
epichlorohydrin
1-chloro-2,3-epoxypropane
γ-Chloropropylene oxide
glycidyl chloride
identifiers of Epichlorohydrine
CAS number of Epichlorohydrine
106-89-8 ☑
3D model (JSmol)
Interactive image
Chebi
Chebi of Epichlorohydrine : 37144 ☑
ChemSpider
13837112 ☑
AKA InfoCard 100.003.128
KEGG
C14449 ☑
pubchem CID
7835
UNII
08OOR508C0 ☑
InChI
InChl = 1 S / C3H5ClO / c4-1-3-2-5-3 / H3H, 1-2H2 ☑
Key: BRLQWZUYTZBJKN-UHFFFAOYSA-N ☑
InChl = 1 / C3H5ClO / c4-1-3-2-5-3 / H3H, 1-2H2
Key: BRLQWZUYTZBJKN-UHFFFAOYAY
Smiles
clcc1co1
Properties of Epichlorohydrine
Chemical formula of Epichlorohydrine
C-3 ‘H 5 ClO
Molar mass of Epichlorohydrine 92.52 g / mol
Appearance of Epichlorohydrine colorless liquid
Smell like garlic or chloroform
Density of Epichlorohydrine 1,1812 g / cm 3
Melting point of Epichlorohydrine -25.6 ° C (-14.1 ° C; 247.6 K)
Boiling point of Epichlorohydrine 117.9 ° C (244.2 ° F; 391.0 K)
solubility of Epichlorohydrine in water
7% (20 ° C)
Vapor pressure of Epichlorohydrine 13 mmHg (20 ° C)
hazards
Safety Data Sheet External product safety form
EU classification (DSD) (outdated)
Toxic T
NFPA 704
NFPA 704 four-color diamond
332
Flash point of Epichlorohydrine 32 ° C (90 ° F, 305 K)
Explosive limits of Epichlorohydrine 3.8% 21%
A lethal dose or concentration (LD, LC):
LC 50 (average concentration)
3617 ppm (rat, 1 hour)
2165 ppm (rat, 1 hour)
250 ppm (rat, 8 hours)
244 ppm (rat, 8 hours)
360 ppm (rat, 6 hours)
LC Lo (low pass)
250 ppm (mouse, 4 hours)
US health exposure limits (NIOSH):
PEL (Permission)
TWA 5 ppm (19 mg / m 3) [surface
Epiklorohidrin
Epiklorohidrin / ECHPropilenin klorlanmasndan yola çklarak elde edilen, epoksi reçinelerin ve epiklorhidrin lastiinin üretiminde kullanlan bileik.
Epiklorohidrin Kimyasal ad: Klorometilokziran
Epiklorohidrin Kimyasal formülü:
Epiklorohidrin Kaynama noktas: 116°C
Epiklorohidrin (ksaltlm ECH), bir organoklorin bileii ve bir epoksittir. Adna ramen halohidrin deildir. Keskin, sarmsak benzeri bir kokuya sahip, suda orta derecede çözünür, ancak çou polar organik çözücüyle karabilen renksiz bir svdr. [4] Genellikle sa ve sol elli enantiyomerlerin rasemik bir karm olarak bulunan iral bir moleküldür. Epiklorohidrin oldukça reaktif bir elektrofilik bileiktir ve gliserol, plastikler, epoksi yaptrclar ve reçineler, epoksi seyrelticiler ve elastomerlerin üretiminde kullanlr.
Üretim
Epiklorohidrin, geleneksel olarak alil klorürden, iki izomerik alkolden oluan bir karm salayan hipokloröz asit ilavesiyle balayarak iki aamada üretilir: [5] [6]
Epiklorohidrin -production-step1-2D-skeletal.png
kinci aamada, bu karm epoksit vermek için baz ile muamele edilir:
Epiklorohidrin -production-step2-2D-skeletal.png
Bu ekilde ylda 800.000 tondan (1997) fazla epiklorohidrin üretilmektedir. [7]
Epiklorohidrin Gliserol yollar
Epiklorohidrin ilk olarak 1848’de Marcellin Berthelot tarafndan tanmland. Bileik, gliserol ve gaz halindeki hidrojen klorür arasndaki reaksiyonlar üzerine yaplan çalmalar srasnda izole edildi. [8]
Berthelot’un deneyini anmsatan gliserolden epiklorohidrin’e (GTE) bitkiler ticariletirildi. Bu teknoloji, biyoyakt ilemeden elde edilen ucuz gliserolün varlndan yararlanmaktadr. [9] Dow Chemical tarafndan gelitirilen süreçte gliserol, bir karboksilik asit katalizörü varlnda hidrojen klorür ile ilendiinde iki ikame reaksiyonundan geçer. Bu, allil klorür / hipokloröz asit ileminde oluan ayn ara üründür ve benzer ekilde epiklorohidrin oluturmak için baz ile ilenir. [10]
GTE-Prozess.svg
Dier yollar
Daha az klorlu ara madde içeren yollar ilgi çekmeye devam etti. Böyle bir ilem alil klorürün epoksidasyonunu gerektirir. [11]
Bavurular
Gliserol ve epoksi reçineleri sentezi
Epiklorohidrin, esas olarak epoksi reçinelerin üretiminde bir yap ta olan bisfenol A diglisidil etere dönütürülür. [12] Ayn zamanda dier reçineler ve polimerler için monomerlerin öncüsüdür. Dier bir kullanm, sentetik gliserole dönütürmedir. Bununla birlikte, gliserolün bir atk ürün olduu biyodizel üretimindeki hzl art, piyasada gliserol bolluuna yol açarak bu süreci ekonomik hale getirmitir. Sentetik gliserol artk sadece hassas ilaç ve biyoteknoloji uygulamalarnda kalite standartlarnn çok yüksek olduu yerlerde kullanlmaktadr. [13]
Küçük ve ni uygulamalar
Epiklorohidrin, birçok organik bileiin sentezinde çok yönlü bir öncüdür. Örnein, patlayc ve itici bileimlerde kullanlan enerjik bir balayc olan glisidil nitrata dönütürülür. [14] Epiklorohidrin, sodyum nitrat gibi bir alkali nitrat ile reaksiyona girerek glisidil nitrat ve alkali klorür üretir. Selüloz, reçineler ve boyalar için çözücü olarak kullanlr ve böcek fümigant olarak kullanm alan bulmutur. [15]
Epiklorohidrinden yaplan polimerler, örnein poliamid-epiklorohidrin reçineleri kat takviyesinde ve gda endüstrisinde çay poetleri, kahve filtreleri ve sosis / salam klflarnn yan sra su artmada kullanlr. [16]
Epiklorohidrinin önemli bir biyokimyasal uygulamas, dekstranlardan Sephadex boyut dlama kromatografik reçinelerinin üretimi için çapraz balama maddesi olarak kullanlmasdr. [17]
Emniyet
Epiklorohidrin, birkaç uluslararas salk aratrma ajans ve grubu tarafndan insanlarda olas veya olas bir kanserojen olarak snflandrlmtr. [18] [19] [20] Yüksek seviyelerde epiklorohidrin’in uzun süreli oral tüketimi mide sorunlarna ve kanser riskinin artmasna neden olabilir. [21] Solunum yoluyla epiklorohidrine mesleki maruziyet, akcier tahriine ve akcier kanseri riskinin artmasna neden olabilir. [
Epiklorohidrin (ksaltlm ECH ) bir bir organik klor bileii, bir epoksit . Adna ramen, bu deil halohidrin . Bu orta suda çözünebilir, fakat bir keskin, sarmsak gibi bir kokusu olan, renksiz bir sv olduu karabilir çou polar organik çözücüler . Bu ise kiral genellikle gibi mevcut molekül rasemik bir karm sa elini ve solak arasnda enantiomerler . Epiklorohidrin oldukça reaktiftir elektrofilik bileik ve üretiminde kullanlan gliserol , plastik, epoksi yaptrclar ve reçineler ve elastomerler .
Gliserol ve epoksi reçineler sentezi
Epiklorohidrin esas olarak dönütürülür bisfenol A diglisidil eter , imalatnda bir yap blounu epoksi reçineleri . Ayn zamanda, dier reçineler ve polimerler için monomerlere öncüsüdür. Baka bir kullanm, sentetik dönüüm olan gliserol . Ancak hzl art biyodizel gliserol bir atk ürünüdür üretim, bu süreç ekonomik olmayan render piyasada gliserol fazlal yol açmtr. Sentetik gliserol imdi sadece hassas ilaç kullanlan ve biyoteknoloji uygulamalarnda kalite standartlar çok yüksek olmas halinde olan.
Epiklorohidrin Minör ve ni uygulamalar
Epiklorohidrin birçok organik bileiklerin sentezinde çok yönlü bir öncüsüdür. Örnein, dönütürülür nitrat glisidil , patlayc ve itici gaz bileimlerinde kullanlan enerjik balayc. Epiklorohidrin gibi bir alkali nitrat ile reaksiyona sokulmaktadr sodyum nitrat glisidil nitrat ve alkali klorür üreten. Bunun için çözücü madde olarak kullanlan selüloz , reçineler ve boyalar ve bir böcek fümigan olarak kullanm alan bulmutur.
Epiklorohidrinden üretilen polimerler, örnein, poliamid-epiklorohidrin reçineleri imalat için kat güçlendirme ve gda endüstrisinde kullanlan çay poetleri, kahve filtreleri, ve sucuk / salam muhafazalar gibi olan su artma .
epiklorohidrin önemli biyokimyasal uygulama dekstranlar Sephadex boyut dlama kromatografisi reçinelerin üretimi için çapraz balama maddesi olarak kullanmdr.
Emniyet
Epikloridin insanlarda olas veya muhtemel karsinojen olarak birçok uluslararas salk aratrma kurumlar ve gruplar tarafndan snflandrlr. epiklorohidrin yüksek seviyelerinin uzun süre azdan tüketim mide problemleri ve kanser riskinin artmasna yol açabilir. inhalasyon yoluyla epiklorohidrine Mesleki maruziyet akcier tahri ve akcier kanseri riskinin artmasna neden olabilir.
Epiklorohidrin, endüstriyel solvent olarak kullanlan klorlu bir epoksi bileendir. Epiklorohidrin, cildi tahri edici ve kanserojendir.
(Klorometil) oksiran, gda niastasnda (Klorometil) oksirann Epoksitler ailesine ait dekstroz birimlerini çapraz balama için kullanlr.
Bunlar üç halka atomlu (bir oksijen ve iki karbon atomlu) halkal bir eter içeren bileiklerdir. Epiklorohidrin’in moleküler formülü ise C3H5ClO’dur.
Epiklorohidrin esas olarak epoksi reçinelerinin üretiminde kullanlr. yerinde epichlorohydrin’e akut (ksa süreli) solunum yoluyla maruz kalnmas, gözler, solunum yolu ve içiler derisinde iritasyona neden olmutur.
Yüksek düzeyde maruz kalma durumunda, insanlarda bulant, kusma, öksürük, emzikli solunum, akcier iltihab, pulmoner ödem ve renal lezyonlar görülebilir.
Havadaki insanlardaki Epiklorohidrin’e maruz kalma kronik (uzun süreli) mesleki maruziyet, yüksek seviyelerde solunum yolu hastalklar ve hematolojik etkiler ile ilikilidir.
Akut veya kronik süreyle inhalasyon yoluyla Epiklorohidrin uygulanan kemirgenlerde burun pasajlar, solunum yolu ve böbrekler hasar görmütür. nhalasyon uygulanan sçanlarda burun boluunun tümör orannda art görülmütür.
Epiklorohidrin Renk APHA’dan ≤ 40
Epiklorohidrin viskozite mPa.s (25 ℃) 40-80
Epiklorohidrin Epoksi Deeri edeer / 100 g 0.35-0.40
Epiklorohidrin Hidrolize Edilebilir Klorür % ≤ 0.50
Epiklorohidrin norganik Klor mg / kg ≤ 50
Epiklorohidrin Nemli içerik % ≤ 0.10
EPA, Epiklorohidrin’i olas insan kanserojeni , Grup B2 olarak snflandrd.
Epiklorohidrin, berrak kloroform benzeri bir kokuya sahip berrak renksiz bir svdr. Younluk 9.8 lb / gal. Parlama noktas ise 87 ° F dir. Polimerletirilebilirdir. Polimerizasyon kapal bir kabn içinde gerçekleirse,
Konteynr iddetli yrtlmaya maruz kalr. Cildi ve solunum sistemini tahri eder. Yutulduunda zehirlidir. Kanserojen tespit edildi.Plastik yapmnda ve çözücü olarak kullanlr.
Epiklorohidrin hafifçe tahri edici ve kloroform benzeri kokusu olan renksiz bir svdr. Epiklorohidrin’in aki serbest radikal ilemi ile okside edilebilir.Bu reaksiyonlar fotokimyasal olarak balatlan atmosferik reaksiyonlar eklinde ortaya çkabilir.
Epiklorohidrin’in birincil kullanm, kaplamalarda, yapkanlarda ve plastiklerde kullanlan epoksi reçinelerinin üretiminde kullanlr.
Epiklorohidrin ayrca sentetik gliserin, tekstil, kat, mürekkep ve boyalar, çözücüler, sürfaktanlar ve farmasötik ürünlerin üretiminde de kullanlr.
Ticari böcek ilacnda inert bir bileen olarak Epiklorohidrin listelenmitir. Endüstride Epiklorohidrin’in kullanm, yaptrclar ve dolgu macunu kimyasallar, ara maddeleri, çözücülerdir (ürün formülasyonunun veya karmn parças haline gelir).
Epiklorohidrin’in tüketici kullanmlar ise yaptrclar ve szdrmazlk maddeleri, boya ve kaplamalardr.
XY215 Epiklorohidrin Polietilen Glikol Kopolimer CAS 39443 66 8 PEG DGE
Dietilen Glikol Diglisidil eter
1. Açklama
Kimyasal ad: Dietilen glikol diglisidil eter; PEG-DGE
Yapsal Formül: O (CH2CH) CH20 (CH2CH20) nCH2 (CHCH2) O
CAS Numaras: 39443-66-8
Fiziksel ve Kimyasal Karakter: renksiz ila hafif sar effaf sv
2. Teknik Veri Sayfas
madde birim Özellikleri.
Epiklorohidrin Renk APHA’dan ≤ 40
Epiklorohidrin viskozite mPa.s (25 ℃) 40-80
Epiklorohidrin Epoksi Deeri edeer / 100 g 0.35-0.40
Epiklorohidrin Hidrolize Edilebilir Klorür % ≤ 0.50
Epiklorohidrin norganik Klor mg / kg ≤ 50
Epiklorohidrin Nemli içerik % ≤ 0.10
3.Epiklorohidrin Uygulama
Epoksi reçine aktif seyrelticilerin çift ilevsellii, iyi esneklik, geni ve orta boy kurularda yaygn olarak kullanlan çeitli epoksi reçine döküm malzemelerinin, solventsiz kaplamalarn, emprenye tutkal ve damla kordon tutkalnn ve yaptrcnn hazrlanmas için kullanlabilir. tipi transformatörler, trafo yüksek gerilim anahtarlama bileenleri, mikro motorlar, kapasitörler ve dier elektronik bileenlerin üretimi; ayrca otomotiv elektronik boyasnn ana bileenleridir.
4. Epiklorohidrin Ambalaj
– 20 kg / varil veya 200 kg / varil veya 1000kgs / IBC kapta paketlenmitir
– Depolama ve nakliye, normal kimyasallarn temel gereksinimlerine uygun olmaldr.
– Serin, kuru ve iyi havalandrlan bir yerde saklayn. Tututurucu kaynaklardan, s ve alevden ve güne ndan uzak tutun.
– Nem emiliminden kaynaklanan olumsuz etkiyi önlemek için kullanmdan sonra yaltlm (skca kapatlm) muhafaza edilmesi gerekir.
Epiklorohidrin, ayrmaya kadar stldnda hidroklorik asit ve dier klorlu bileiklerin toksik dumanlarn yayan, tahri edici, kloroform benzeri bir kokuya sahip uçucu ve yanc, berrak, renksiz, sv, klorlanm siklik bir eterdir. Epiklorohidrin, epoksi reçineler, sentetik gliserin ve elastomerlerin üretiminde kullanlr. Epiklorohidrine maruz kalma gözleri, cildi ve solunum sistemini tahri eder ve kimyasal pnömoniye, akcier ödemine ve böbrek lezyonlarna neden olabilir.
Epiklorohidrin (klorometiloksiran), CH2 (O) CH-CH2CI formülüne sahip organik bir maddedir, propilen oksidin bir kloro türevi. Epoksi reçineleri ve gliserin üretiminde kullanlan organik sentezde yaygn olarak kullanlmaktadr. Oldukça toksik, tahri edici.
Epiklorohidrin, metil hidrojenlerden birinin klor ile ikame edildii 1,2-epoksipropen olan bir epoksittir. Bir organoklor bileii ve bir epoksittir. 1,2-epoksipropandan türemitir.
(Klorometil) oksiran, alfa-epiklorohidrin veya 1-kloro-2, 3-epoksipropan olarak da bilinir, epoksitler olarak bilinen organik bileikler snfna aittir. Epoksitler, üç halka atomlu (bir oksijen ve iki karbon atomlu) (Klorometil) oksiran, sv, çözünür (suda) ve son derece zayf bazik (esasen nötr) bir bileik (pKa’sna dayal olarak) olarak bulunan siklik bir eter içeren bileiklerdir. … Hücre içinde, (klorometil) oksiran, öncelikle sitoplazmada bulunur (Klorometil) oksiran, 1,2-epoksipropandan biyosentezlenebilir.
Fiziksel özellikler
Tahri edici bir kloroform kokusuna sahip renksiz, hareketli effaf bir svdr, çou organik çözücüde suda çok az çözünür. Kaynama noktas +88 ° C olan su ile azeotropik bir karm oluturur ve% 75 epiklorohidrin içerir. Çok sayda organik svyla azeotropik karmlar oluturur. Epiklorohidrin, asimetrik bir karbon atomunun varlndan dolay optik olarak aktiftir.
Kimyasal özellikler
Epiklorohidrin, aktif bir epoksi grubu ve bir mobil klor atomu ile kimyasal olarak oldukça reaktif bir bileiktir.
Halojenasyon reaksiyonu
Klor, normal koullar altnda epiklorohidrin ile etkileime girdiinde 3,3-dikloropropilen oksit (3,3-dikloroepoksipropilen) oluur [5
Hidroklorlama reaksiyonu
1,3-diklorohidrin oluumu ile hem çözelti içinde hem de susuz ortamda normal scaklkta kolayca hidrojen klorür ekler
Dehidroklorinasyon reaksiyonu
Az miktarda alkali varlnda epiklorohidrin, klorohidrinleri oluturmak için bir veya daha fazla mobil hidrojen atomu içeren bileikleri kolayca balar:
Alkali konsantrasyonundaki bir artla reaksiyon, hidrojen klorürün ortadan kaldrlmas ve epoksi grubunun indirgenmesiyle, ancak farkl bir konumda ilerler:
Hidroliz reaksiyonu
Fazla miktarda alkali (çounlukla sodyum karbonat kullanlr) ve 100 ° C scaklkta epiklorohidrin yavaça gliserine dönütürülür.
Hidrasyon reaksiyonu
seyreltik inorganik asitlerin (sülfürik veya ortofosforik) varlnda, epiklorohidrin gliserol α-monoklorohidrin oluturur
Scaklk yükseldikçe, epiklorohidrinin hidrasyonu artar.
Esterifikasyon reaksiyonu
Epiklorohidrin alkollerle etkileime girdiinde, epoksi halkas, 2. pozisyonda bir hidroksil grubunun oluumu ve bir eter oluumu ile açlr.
Aminasyon reaksiyonu
Zaten normal scaklktaki epiklorohidrin halka açklyla amonyak veya aminler ekler
Epiklorohidrin, polimerik diglisid eter oluturmak için difenilolpropan ile reaksiyona girer.
Diglisidether
Bu reaksiyon, istisnai özelliklerinden dolay son zamanlarda çok yaygnlaan epoksi reçinelerin üretimine bir örnektir.
Polimerizasyon reaksiyonu
Epiklorohidrin polimerize olabilir. Kullanlan katalizöre bal olarak mobil svlar, yüksek viskoziteli yalar veya reçine benzeri ürünler elde edilir.
Uygulama
Gliserin türevlerinin, boyalarn ve yüzey aktif maddelerin sentezi için bir ara ürün olarak kullanlr; sentetik malzemelerin üretimi için (esas olarak epoksi reçineler).
Toksikoloji ve güvenlik
Eylemin genel nitelii
Tahri edici ve alerjik etkiye sahiptir. Hayvanlar üzerinde yaplan deneylerde seçici olarak böbrekleri etkiler. Deriye nüfuz eder.
Epiklorohidrin oldukça zehirli ve yanc bir bileiktir. Epiklorohidrin buharlar, küçük konsantrasyonlarda bile solunduunda mide bulants, ba dönmesi ve gözya oluumuna neden olur ve uzun süre maruz kalndnda daha ciddi sonuçlara yol açar (genellikle iddetli pulmoner ödem oluur). Epiklorohidrin deri ile temas halinde ve uzun süreli temas yüzeysel nekroza kadar dermatite neden olur. Epiklorohidrin ile yaplan tüm çalmalar lastik eldivenlerde, lastik önlükte ve buharlarda güçlü gaz kirlilii durumunda – A snf bir gaz maskesinde yaplmaldr.
Épichlorohydrine
(±)-Épichlorohydrine
Image illustrative de l’article Épichlorohydrine
R-Epichlorohydrin-calculated-MP2-3D-balls.pngS-Epichlorohydrin-calculated-MP2-3D-balls.png
Énantiomère R de l’épichlorohydrine (à gauche) et S-épichlorohydrine (à droite)
Identification
Nom UICPA 2-(chlorométhyl)oxirane
Synonymes
1-chloro-2,3-epoxypropane
γ-oxyde de chloropropylène
chlorure de glycidyle
No CAS 106-89-8 (R,S)
No ECHA 100.003.128
No CE 203-439-8
PubChem 7835 [archive]
SMILES
[Afficher]
InChI
[Afficher]
Apparence liquide incolore
Propriétés chimiques
Formule brute C3H5ClO [Isomères]
Masse molaire1 92,524 ± 0,005 g/mol
C 38,94 %, H 5,45 %, Cl 38,32 %, O 17,29 %, 92.52 g/mol
Propriétés physiques
T° fusion -48 °C 2
T° ébullition 116,56 °C 2
Solubilité 6,59 g/100ml (eau, 25 °C);
Miscible avec l’alcool, l’éther, le chloroforme, le trichloroéthylène, le tétrachlorure de carbone; Immiscible avec les hydrocarbures de pétrole3
Paramètre de solubilité δ 22,5 MPa1/2 (25 °C)4
Masse volumique 1,18066 g·cm-3 à 20,0 °C2
T° d’auto-inflammation 415,6 °C 2
Point d’éclair 40,6 °C 2
Pression de vapeur saturante 1,333 kPa à 16,6 °C 2
Viscosité dynamique 1,03 mPa·s à 25 °C 2
Précautions
SGH5
SGH02 : InflammableSGH05 : CorrosifSGH06 : ToxiqueSGH07 : Toxique, irritant, sensibilisant, narcotiqueSGH08 : Sensibilisant, mutagène, cancérogène, reprotoxique
H226, H301, H311, H314, H331, H350,
[+]
SIMDUT6
B3 : Liquide combustibleD1A : Matière très toxique ayant des effets immédiats gravesE : Matière corrosive
B3, D1A, D2A, E,
NFPA 7047
Symbole NFPA 704.
332
Transport5
63
2023
[+]
Classification du CIRC
Groupe 2A,carcinogène
Inhalation TLV: 2 ppm
Peau 7.6 mg/m3
Écotoxicologie
DL50 90 mg·kg-1 (rat, oral)
154 mg·kg-1 (rat, i.v.)
150 mg·kg-1 (rat, s.c.)
113 mg·kg-1 (rat, i.p.) 8
LogP 0,45 8
Seuil de l’odorat bas : 0,93 ppm
Unités du SI et CNTP, sauf indication contraire.
modifier Consultez la documentation du modèle
L’épichlorohydrine ou épichlorhydrine ou 1-chloro-2,3-époxypropane, est un composé organochloré de formule semi-développée CH2CHOCH2Cl, liquide volatil toxique, incolore à forte odeur d’ail. Un atome de carbone de l’épichlorohydrine est chiral, il existe donc deux formes énantiomères de ce composé.
Sommaire
1 Utilisation
2 Production
3 Sécurité
3.1 Notes et références
4 Articles connexes
Utilisation
L’épichlorohydrine est utilisé dans la fabrication de résines plastiques, de résines échangeuses d’ions, de polyétherpolyols pour des mousses polyuréthane ignifugées, d’alkylglycéryléthersulfonates pour des détergents, d’élastomères (codes de polymère CO, ECO), de résines spéciales pour le traitement du papier, du glycérol et de ses dérivés10.
Production
L’épichlorohydrine est fabriquée à partir de chlorure d’allyle en deux étapes, d’abord, une hydrochloration utilisant l’acide hypochloreux, donnant un mélange d’alcools :
Epichlorohydrin-manufacture-step1-2D-skeletal.png
La deuxième phase aboutit à la formation de l’époxyde par traitement avec une base :
Epichlorohydrin-manufacture-step2-2D-skeletal.png
Sécurité
Inflammable
Peut provoquer le cancer.
Toxique par inhalation, par contact avec la peau et par ingestion.
Provoque des brûlures.
Peut entraîner une sensibilisation par contact avec la peau.
Des produits de décomposition dangereux se forment en cas de feu.
Identification
Description
Numéro UN : UN2023
Formule moléculaire brute : C3H5ClO
Principaux synonymes
Noms français :
1-CHLORO-2,3-EPOXY PROPANE (EPICHLORHYDRIN)
1-CHLORO-2,3-EPOXYPROPANE
2-CHLOROPROPYLENE OXIDE
CHLORO-1 EPOXY-2,3 PROPANE
CHLOROMETHYLOXIRANE
DL-ALPHA-EPICHLOROHYDRIN
Epichlorhydrin
EPICHLOROHYDRINE
GAMMA-CHLOROPROPYLENE OXIDE
Épichlorhydrine
Épichlorohydrine
Noms anglais :
Epichlorhydrin
Epichlorohydrin
Utilisation et sources d’émission
Fabrication de résines, fabrication de polymères
Apparence
Mise à jour : 1991-06-17
Liquide transparent, incolore à odeur chloroformique
Danger immédiat pour la vie et la santé 1
DIVS : 75 ppm
Propriétés physiques 2
Mise à jour : 1991-06-17
État physique : Liquide
Masse moléculaire : 92,53
Densité : 1,1812 g/ml à 20 °C
Solubilité dans l’eau : 70,00 g/l à 20 °C
Densité de vapeur (air=1) : 3,19
Point de fusion : -57,1 °C
Point d’ébullition : 115,00 °C
Tension de vapeur : 13,0 mm de Hg (1,73 kPa) à 20 °C
Concentration à saturation : 17100 ppm
Limite de détection olfactive : 25,00 ppm
Facteur de conversion (ppm->mg/m³) : 3,784
Taux d’évaporation (éther=1) : 17,00
Inflammabilité et explosibilité
Mise à jour : 1994-05-15
Inflammabilité
Ce produit est inflammable dans les conditions suivantes:
Peut s’enflammer s’il est chauffé modérément et en présence d’une source d’ignition.
Données sur les risques d’incendie 3
Mise à jour : 2016-01-12
Point d’éclair : 37,8 °C Coupelle ouverte, méthode Tag
Autre(s) valeur(s) : 31,11 °C Coupelle ouverte
T° d’auto-ignition : 416 °C
Limite inférieure d’explosibilité : 3,8% à 25 °C
Limite supérieure d’explosibilité : 21,0% à 25 °C
Techniques et moyens d’extinction
Mise à jour : 1994-05-15
Moyens d’extinction
dioxyde de carbone, mousse, poudre chimique sèche
Informations supplémentaires: Note: il est préférable de ne pas utiliser d’eau (réaction violente possible).
Techniques spéciales
Porter un appareil respiratoire autonome muni d’un masque facial complet. Si le feu a pris des proportions importantes ou si les contenants y sont exposés, quitter les lieux rapidement.