Synthesis of 3-chloro-1,2-propanediol

Preparation of 3-chloro-1,2-propanediol

To the mixture of  500 g of glycerol and glacial 10 g of acetic acid a gaseous hydrogen chloride is passed at 105-110° C until a weight increase of 190 g is achieved. Alternatively, gaseous hydrogen chloride is led into thoroughly dehydrated glycerol containing 2% of succinic acid for 8 h without heating, the heat of reaction alone causing the temperature to rise to 60-70° C. On distillation in a vacuum, mainly water passes over up to b.p. 114° C/14 mm, then between 114° C and 120° C 66 % or 360 g of 3-chloro-1,2-propanediol (b.p. 113.5710.5 mm).

Org. Syn., 2, 33 (1922).

Z. Phys. Chem., 94, 701 (1920).

IUPAC Name

3-chloropropane-1,2-diol

InChI

InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2

InChI Key

SSZWWUDQMAHNAQ-UHFFFAOYSA-N

Canonical SMILES

C(C(CCl)O)O

MeSH Synonyms

3 Chloro 1,2 propanediol, 3 Chloropropanediol, 3 Monochloropropane 1,2 diol, 3-Chloro-1,2-propanediol, 3-Chloropropanediol, 3-MCPD, 3-monochloropropane-1,2-diol, alpha Chlorhydrin, alpha Chlorohydrin, alpha-Chlorhydrin, alpha-Chlorohydrin, alpha-Monochlorohydrin, Glycerol, Glycerol alpha Monochlorohydrin, Glycerol alpha-Monochlorohydrin, U 5897, U-5897, U5897

Depositor-Supplied Synonyms

3-Chloro-1,2-propanediol, 3-Chloropropane-1,2-diol, alpha-Chlorohydrin, 96-24-2, Chlorodeoxyglycerol, Glycerol alpha-monochlorohydrin, Epibloc, 1,2-Propanediol, 3-chloro-, 3-Chloropropylene glycol, 3-Chloropropanediol, Glycerol chlorohydrin, a-chlorohydrin, Monochlorohydrin, 1-Chloro-2,3-propanediol, 1-Chloropropane-2,3-diol, Chloropropanediol, Glyceryl chloride, 1-Chloro-2,3-dihydroxypropane, alpha-Chlorohydrine, 2,3-Dihydroxypropyl chloride, Chlorhydrin, Glycerin epichlorohydrin, Monochlorhydrin, Glycerol 3-chlorohydrin, 3-CHLORO-1,2-DIHYDROXYPROPANE, 1-Chloro-1-deoxyglycerol, 3-MCPD, u 5897, .alpha.-Chlorohydrin, 1,2-Dihydroxy-3-chloropropane, alpha-Monochlorohydrin, 1,2-Propanediol, 3-dichloro-, 3-Chloro-1,2-propylene glycol, Caswell No. 214A, (RS)-3-chloro-1,2-propanediol, U-5897, Glyceryl alpha-chlorohydrin, Glyceryl-alpha-chlorohydrin, 3-Chloro-1,2-propandiol, 3-chloro-propane-1,2-diol, Glycerin alpha-monochlorhydrin, 3-Monochloro-1,2-propanediol, CCRIS 4607, CHEBI:18721, HSDB 2052, SSZWWUDQMAHNAQ-UHFFFAOYSA-N, (+-)-2,3-Dihydroxychloropropane, EINECS 202-492-4, UN2689, beta,beta’-Dihydroxyisopropyl chloride, EPA Pesticide Chemical Code 117101, BRN 0635684, AI3-11200, DSSTox_CID_664, alpha-Glycerol chlorohydrin, DSSTox_RID_75718, DSSTox_GSID_20664, 3-Chloro-1,2-propanediol-d5, (+/-)-3-Chloro-1,2-propanediol, CAS-96-24-2, C3H7ClO2, 3-Monochloropropane-1,2-diol, a-Monochlorohydrin, a-Glycerol chlorohydrin, PubChem21311, ACMC-209lvy, ACMC-209mmh, Chloro-1,2-propanediol, AC1L1OFP, AC1Q3TVO, .alpha.-Monochlorohydrine, AC1Q7BQ6, 3-chloro-1,2-propan-diol, glycerol |A-monochlorohydrin, 3-Chloropropandiol-(1,2), Chloro-1,2-dihydroxypropane, 3-chloro-1,2-propane diol, 3-chloro-1,2-propane-diol, SCHEMBL19213, Glycerol .alpha.-chlorohydrin, Glyceryl .alpha.-chlorohydrin, MLS000028887, C0639_SIGMA, 107271_ALDRICH, Glycerine alpha-monochlorohydrin, CHEMBL3185949, Glycerin .alpha.-monochlorhydrin, CTK3J4624, Glycerol-.alpha.-monochlorohydrin, MolPort-001-779-558, BB_SC-6682, 3-chloro-1,2-dihydroxy-n-propane, ACT05631, Tox21_202262, Tox21_302959, ANW-56378, AR-1H6490, BBL011374, SBB060480, STL146471, AKOS000121375, AKOS016370740, (.+/-.)-2,3-Dihydroxychloropropane, LS-2004, MCULE-7895191088, RP18990, RTR-031929, UN 2689, TRA-0189565, NCGC00249201-01, NCGC00256557-01, NCGC00259811-01, AK117071, AN-42782, BC204241, K736, KB-30774, OR012233, OR189219, OR260182, SMR000059152, .beta.,.beta.’-Dihydroxyisopropyl chloride, DB-028420, LS-120252, TR-031929, 3-Chloro-1,2-propanediol Monochlorhydrin, FT-0605055, FT-0605261, FT-0615294, ST51046658, C18676, 131143-EP2284146A2, 131143-EP2284147A2, 131143-EP2295399A2, 157414-EP2275417A2, 157414-EP2284162A2, 157414-EP2284163A2, 4-01-00-02484 (Beilstein Handbook Reference), I14-1465, I14-1681, S14-0919, 3B3-033312, Glycerol alpha-monochlorohydrin [UN2689] [Keep away from food], Glycerol alpha-monochlorohydrin [UN2689] [Keep away from food], 52340-46-2, 69420-22-0

Removed Synonyms

Chlorohydrin, |A chlorohydrin, |A-Chlorohydrin, alpha Chlorhydrin, alpha-Chlorhydrin, alpha Chlorohydrin, 3 Chloropropanediol, Chloropropylene glycol, ? CHLOROHYDRIN, 3 Chloro 1,2 propanediol, (R)-(-)-3-Chloro-1,2-propanediol, Glycerol alpha Monochlorohydrin, 3 Monochloropropane 1,2 diol, alpha-Monochlorohydrin, Glycerol, (S)-(+)-3-Chloro-1,2-propanediol, CID7290, (2S)-3-chloropropane-1,2-diol, c0078, c0268, U5897, C484750, D000517, 57090-45-6, 60827-45-4, 1072-62-4, 312745-09-8

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