EPICHLOROHYDRINE

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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; epichlorohydrine; epichlorohydrin; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;EPIKLOROHIDRIN; (+-)-Isomer;Epichlorohydrin, (S)-Isomer ;EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; Epichlorhydrin; epiklorohidrin; epiklorhidrin; epiklorohydrin; epiklorohidrin; epiklor hidrin; epichlorohydrine; epiklorhidrin; epiklorohidrin; epichlorohydrine; epichlorohydrine; Epichlorohydrin;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; epichlorohydrine; EPİKLOROHİDRİN;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;EPİKLORHİDRİN; epichlorohydrine; EPIKLORHIDRIN; Epiklorohidrin

CAS NO:106-89-8
EC NO:203-439-8

Epichlorohydrine
Epichlorohydrine

(±)-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