Synthesis of epichlorohydrin

Preparation of epichlorohydrin

Alternative Names: 2-(Chloromethyl)oxirane; epichlorohydrin; 1-Chloro-2,3-epoxypropane; Glycidyl chloride; Oxirane, (chloromethyl)-;

Preparation of epichlorohydrin

Preparation of epichlorohydrin

200 g glycerine, which has been heated to remove water in open dishes until a thermometer placed in it indicated 170° C, are dissolved in the same volume of glacial acetic acid, and into this solution is passed a rapid stream of hydrochloric acid, generated and dried in the usual way, until the liquid is saturated at ordinary temperature. The solution is then warmed on the water-bath, and the passage of hydrochloric acid continued about 6 hours more. The mixture is allowed to stand for about 12 hours, and is then subjected to fractional distillation. At first a large amount of hydrochloric acid is evolved, then aqueous acetic acid distils over, and finally a mixture of 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol. The fraction from 160-220° C is collected by itself, and worked up for epichlorohydrin without further purification. From the fraction 110-160° C a small amount of the same product can be precipitated in oily form by the addition of water. The total yield of raw product amounts to about 120% of the glycerine used. The conversion of this product into epichlorohydrin is effected by treating it with aqueous alkali. 100 g potassium hydroxide are dissolved in twice that weight of water; the solution is cooled to room temperature, and it is then gradually poured into the raw mixture of 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol with continual shaking and cooling with water. The oily product changes into mobile epichlorohydrin. The conversion takes place at room temperature smoothly and pretty completely, but the alkaline solution must not be allowed to get very warm, because then the epichlorohydrin itself is further saponified. When the operation is finished the epichlorohydrin is repeatedly extracted with ether; the ethereal solution is dried with sodium sulfate and filtered; the ether is then evaporated, and the residue fractionated. The fraction boiling above 130° C is for the most part unchanged 2,3-dichloro-1-propanol, and is again treated with the solution of potassium hydroxide. Boiling point of epichlorohydrin 119° C. Yield about 45 g.

Introduction to the preparation of organic compounds, E. Fisher, 83-85, 1909

IUPAC Name

2-(chloromethyl)oxirane

InChI

InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2

InChI Key

BRLQWZUYTZBJKN-UHFFFAOYSA-N

Canonical SMILES

C1C(O1)CCl

MeSH Synonyms

Epichlorhydrin, Epichlorohydrin, Epichlorohydrin, (+-)-Isomer, Epichlorohydrin, (S)-Isomer

Depositor-Supplied Synonyms

EPICHLOROHYDRIN, 2-(Chloromethyl)oxirane, Epichlorhydrin, 1-Chloro-2,3-epoxypropane, Glycidyl chloride, Oxirane, (chloromethyl)-, 3-Chloropropylene oxide, 106-89-8, 1,2-Epoxy-3-chloropropane, Chloropropylene oxide, 2,3-Epoxypropyl chloride, Glycerol epichlorohydrin, 3-Chloro-1,2-epoxypropane, Epichlorhydrine, Epicloridrina, Epichloorhydrine, Epichlorohydryna, Glycerol epichlorhydrin, (CHLOROMETHYL)OXIRANE, Chloromethyloxirane, SKEKhG, 3-Chloro-1,2-propylene oxide, Epichlorophydrin, Oxirane, 2-(chloromethyl), (Chloromethyl)ethylene oxide, 3-Chloropropene-1,2-oxide, Epoxypropyl chloride, Propane, 1-chloro-2,3-epoxy-, alpha-Epichlorohydrin, 1-Chlor-2,3-epoxy-propan, 1-Cloro-2,3-epossipropano, 1-Chloor-2,3-epoxy-propaan, Chloromethyl, .alpha.-Epichlorohydrin, (+/-)-Epichlorohydrin, epi-Chlorohydrin, (+/-)-2-(Chloromethyl)oxirane, Rcra waste number U041, Alyl chloride oxide, .gamma.-Chloropropylene oxide, Allyl chloride oxide, (DL)-.alpha.-Epichlorohydrin, DL-a-Epichlorohydrin, (-)-Epichlorohydrin, Epoxy-3-chloropropane, Caswell No. 424, (chloromethyl)-Oxirane, Epicloridrina [Italian], Oxirane, (chloromethyl)-, (R)-, Oxirane,(chloromethyl)-, Epichloorhydrine [Dutch], Epichlorhydrine [French], NSC 6747, Epichlorohydryna [Polish], gamma-Chloropropylene oxide, RCRA waste no. U041, oxirane, 2-(chloromethyl)-, HSDB 39, (chloromethyl) Ethylene oxide, CCRIS 277, CCRIS 6387, CHEBI:37144, BRLQWZUYTZBJKN-UHFFFAOYSA-N, (RS)-3-chloro-1,2-epoxypropane, NCI-C07001, EINECS 203-439-8, UN2023, 1-Chlor-2,3-epoxy-propan [German], 1-Chloor-2,3-epoxy-propaan [Dutch], 1-Cloro-2,3-epossipropano [Italian], EPA Pesticide Chemical Code 097201, BRN 0079785, BRN 1420785, NCGC00091792-01, AI3-03545, DSSTox_CID_566, (R)-(Chloromethyl)oxirane, Epichlorohydrin-2-13C, DSSTox_RID_75662, DSSTox_GSID_20566, 56227-39-5, 9009-12-5, CAS-106-89-8, ECH, 5-17-01-00020 (Beilstein Handbook Reference), Chloropropylene, Polidexide, Polidexidi sulfas, Chloromethyl radical, Chloropropyl epoxide, 2-chloromethyloxirane, chloromethyl) Oxirane, Sulfate de polidexide, Sulfato de polidexido, Cardolite NC-513, 2-Chloromethyl-oxirane, 3-Chloropropyl epoxide, beta-epoxypropylchloride, Epoxy-3-chlor opropane, AC1L1PNR, AC1Q3UAD, 3-Chloro-propylene oxide, Chloro-1,2-epoxypropane, Chloro-2,3-epoxypropane, Chloropropene-1,2-oxide, 2-(chloromethyl)-oxirane, 3-Chloropro pylene Oxide, 2-(chloromethyl) Oxirane, bmse000722, WLN: T3OTJ B1G, (RS)-(chloromethyl)oxirane, E1055_ALDRICH, Chloro-1,2-propylene oxide, 1-chloro-2,3-epoxy-propane, 1-Chloro-2,3-epoxy propone, ( )-2-(Chloromethyl)oxirane, 240699_ALDRICH, 442580_SUPELCO, 481386_ALDRICH, Polidexidi sulfas [INN-Latin], CHEMBL1421613, 02578_FLUKA, CTK5A4812, NSC6747, MolPort-001-779-799, BB_SC-6806, NSC-6747, Sulfate de polidexide [INN-French], Tox21_111167, Tox21_200276, 6660AH, AR-1I7145, BBL012223, LS-409, STL163564, Sulfato de polidexido [INN-Spanish], Epichlorohydrin [UN2023] [Poison], AKOS000118974, AKOS016039400, Epichlorohydrin [UN2023] [Poison], MCULE-9759519789, RP18559, TRA0067700, UN 2023, NCGC00091792-02, NCGC00091792-03, NCGC00257830-01, BP-31004, HE027244, HE293532, HE315376, HE379166, KB-50544, KB-309491, LS-101030, TL8003414, E0012, FT-0625672, 5717-EP2269977A2, 5717-EP2270011A1, 5717-EP2272817A1, 5717-EP2272839A1, 5717-EP2272840A1, 5717-EP2272841A1, 5717-EP2275418A1, 5717-EP2277874A1, 5717-EP2277878A1, 5717-EP2280001A1, 5717-EP2280009A1, 5717-EP2280010A2, 5717-EP2284159A1, 5717-EP2284169A1, 5717-EP2287161A1, 5717-EP2287162A1, 5717-EP2292227A2, 5717-EP2292592A1, 5717-EP2292596A2, 5717-EP2292628A2, 5717-EP2295407A1, 5717-EP2295426A1, 5717-EP2295427A1, 5717-EP2295434A2, 5717-EP2295437A1, 5717-EP2298312A1, 5717-EP2298734A2, 5717-EP2298736A1, 5717-EP2298750A1, 5717-EP2298774A1, 5717-EP2298775A1, 5717-EP2301921A1, 5717-EP2301924A1, 5717-EP2301926A1, 5717-EP2301929A1, 5717-EP2301934A1, 5717-EP2301935A1, 5717-EP2301936A1, 5717-EP2301937A1, 5717-EP2301939A1, 5717-EP2305219A1, 5717-EP2305649A1, 5717-EP2305658A1, 5717-EP2305674A1, 5717-EP2305682A1, 5717-EP2308828A2, 5717-EP2308857A1, 5717-EP2308858A1, 5717-EP2308861A1, 5717-EP2308873A1, 5717-EP2308875A1, 5717-EP2308877A1, 5717-EP2308879A1, 5717-EP2311808A1, 5717-EP2311816A1, 5717-EP2311817A1, 5717-EP2311822A1, 5717-EP2311829A1, 5717-EP2311831A1, 5717-EP2311846A1, 5717-EP2314558A1, 5717-EP2314583A1, 5717-EP2314584A1, 5717-EP2314585A1, 5717-EP2316824A1, 5717-EP2316836A1, 5717-EP2371810A1, 5717-EP2371831A1, 5717-EP2372804A1, 5717-EP2374454A1, 5717-EP2378585A1, C14449, 23287-EP2270113A1, 23287-EP2270114A1, 23287-EP2272935A1, 23287-EP2275417A2, 23287-EP2277867A2, 23287-EP2280003A2, 23287-EP2280008A2, 23287-EP2280012A2, 23287-EP2284146A2, 23287-EP2284147A2, 23287-EP2284162A2, 23287-EP2284163A2, 23287-EP2285791A1, 23287-EP2286811A1, 23287-EP2292597A1, 23287-EP2295438A1, 23287-EP2298776A1, 23287-EP2301941A1, 23287-EP2305666A1, 23287-EP2308862A1, 23287-EP2308865A1, 23287-EP2314584A1, 204282-EP2277867A2, 204282-EP2280003A2, 3B4-0902, I14-0790, I14-1670, I14-2684, I14-22999, 109351-74-8, 13403-37-7, 36250-81-4, Starch, 2-(diethylamino)ethyl 2-((2-(diethylamino)ethyl)diethylammonio)ethyl ether, chloride, hydrochloride, polymer with (chloromethyl)oxirane

Removed Synonyms

Methyl, chloro-, (R)-Epichlorohydrin, Propane,3-epoxy-, (R)-(-)-Epichlorohydrin, |A-chloropropylene oxide, 2- OXIRANE, (S)-(+)-Epichlorohydrin, Epichlorohydrin, (S)-Isomer, UNII-08OOR508C0, Epichlorohydrin, (+-)-Isomer, CID7835, c0077, D004811, 51594-55-9, EPI, 108119-59-1, 3302-10-1, 55295-70-0, 6806-86-6

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