Synthesis of chloroacetic acid

Preparation of chloroacetic acid

Chloroacetic acid is prepared by passing chlorine in to glacial acetic acid

Preparation of chloroacetic acid

Preparation of chloroacetic acid

The round bottom flask fitted with reflux condenser, protected from moisture with calcium chloride, and inlet tube reaching almost the bottom of the flask 100 g of glacial acetic acid and 10 g of sulfur are placed. Reaction flask is weight before the synthesis and a fairly rapid stream of dry chlorine is introduced and reaction flask is gently heated. The glacial acetic acid is kept gently boiling and the stream of chlorine continued until an increase in weight of about 38 g has taken place. This usually takes up to 10 hours but direct sunlight could accelerate this process. When reaction is complete the liquid is poured off from the sulfur and distilled. The first portions consist mainly of acetyl chloride, acetic acid. The fraction boiling at about 16o-190° C is collected and, after cooling, any liquid portion poured off and the solid then redistilled. Chloroacetic acid forms colorless sharp-smelling crystals with melting point 63° C, and boiling point 185-187° C. The yield of chloroacetic acid is 70-80 g.

Preparation of organic compounds, E. de. Barry Barnett, 50, 1912

IUPAC Name

2-chloroacetic acid

InChI

InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)

InChI Key

FOCAUTSVDIKZOP-UHFFFAOYSA-N

Canonical SMILES

C(C(=O)O)Cl

MeSH Synonyms

Acetocaustin, chloroacetate, chloroacetic acid, chloroacetic acid, aluminum salt, chloroacetic acid, ammonium (2:1) salt, chloroacetic acid, ammonium salt, chloroacetic acid, calcium (3:1) salt, chloroacetic acid, calcium salt, chloroacetic acid, potassium (2:1) salt, chloroacetic acid, potassium salt, chloroacetic acid, silver salt, chloroacetic acid, sodium (2:1) salt, chloroacetic acid, sodium (5:2) salt, chloroacetic acid, sodium salt, monochloroacetic acid

Depositor-Supplied Synonyms

chloroacetic acid, Monochloroacetic acid, Acetic acid, chloro-, Acide chloracetique, Chloroethanoic acid, Chloracetic acid, 79-11-8, Monochloroethanoic acid, Monochloressigsaeure, 2-chloroacetic acid, Monochloorazijnzuur, Acidomonocloroacetico, Monochloracetic acid, Chloroacetic acid, solid, .alpha.-Chloroacetic acid, Acide monochloracetique, Acetic acid, 2-chloro-, Chloroacetic acid solution, Monochloorazijnzuur [Dutch], Acide chloracetique [French], Acide chloroacetique, Kyselina chloroctova, Kyselina chloroctova [Czech], Monochloressigsaeure [German], Acide chloroacetique [French], Chloroacetic acid [BSI:ISO], Acidomonocloroacetico [Italian], 2-chloro-acetic acid, Acide monochloracetique [French], alpha-Chloroacetic acid, 2-chloro-ethanoic acid, Caswell No. 179B, Monochloroacetic acid [BSI:ISO], NSC 142, Acide chloracetique [ISO-French], Chloroacetic acid (80% or less), NCI-C60231, Chloroacetic acid, molten, UNII-5GD84Y125G, Monochloroacetic acid, solution, CCRIS 2117, HSDB 939, CHEBI:27869, FOCAUTSVDIKZOP-UHFFFAOYSA-N, Chloroacetic, EINECS 201-178-4, UN1750, UN1751, UN3250, EPA Pesticide Chemical Code 279400, BRN 0605438, Monochloracetic acidacide monochloracetique, AI3-25035, Chloroacetic acid, molten [UN3250] [Poison], Chloroacetic acid, solid [UN1751] [Poison], Chloroacetic acid, solution [UN1750] [Poison], Chloroacetic acid, liquid, CHLOROACETIC ACID CRYSTALLINE, Chloroaceticacid, cloroacetic acid, chloro acetic acid, chloro-acetic acid, Acetocaustin (TN), sJPhLQDIKTp@, 2-chloroethanoic acid, CH2ClCOOH, monochloro acetic acid, Aceticacid, 2-chloro-, CHLOROACETIC-ACID, alpha-chloro-acetic acid, DSSTox_CID_901, bmse000367, WLN: QV1G, Chloroacetic acid, solution, AC1L18XJ, AC1Q75JS, AC1Q75JT, DSSTox_RID_75855, NCIOpen2_002217, DSSTox_GSID_20901, C19627_ALDRICH, MLS001065621, BIDD:ER0630, CHEMBL14090, CHLOROACETIC ACID, ACS, 36544_RIEDEL, 442515_SUPELCO, LS-7, NSC142, 36544_FLUKA, C19627_SIAL, CTK2H7513, FOCAUTSVDIKZOP-UHFFFAOYSA-, NSC-142, MolPort-000-871-803, 5GD84Y125G, 402923_SIAL, NSC42970, 3926-62-3 (hydrochloride salt), Tox21_201114, ANW-56416, LMFA01090068, NSC-42970, AKOS000118920, MCULE-9228754880, RP18577, RTR-037847, UN 1751, CAS-79-11-8, NCGC00091473-01, NCGC00091473-02, NCGC00091473-03, NCGC00258666-01, AN-23978, SMR000568484, AB1002140, TR-037847, C2123, FT-0082724, FT-0623627, LT00789405, Chloroacetic acid, solid [UN1751] [Poison], C06755, Chloroacetic acid, molten [UN3250] [Poison], D07677, 33169-EP2292597A1, 33169-EP2301918A1, 33169-EP2305649A1, 33169-EP2311815A1, 33169-EP2374786A1, 44264-EP2289882A1, 44264-EP2289890A1, 44264-EP2292597A1, 44264-EP2298776A1, 44264-EP2301911A1, 44264-EP2308833A2, 44264-EP2311814A1, 44264-EP2374786A1, Chloroacetic acid, solution [UN1750] [Poison], 4-02-00-00474 (Beilstein Handbook Reference), 3B4-0485, I04-1105, InChI=1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5), R3W

Removed Synonyms

chloroacetate, Acetocaustin, chloroacetic acid, silver salt, chloroacetic acid, sodium salt, chloroacetic acid, calcium salt, CID300, chloroacetic acid, aluminum salt, chloroacetic acid, ammonium salt, chloroacetic acid, potassium salt, chloroacetic acid, sodium (2:1) salt, chloroacetic acid, sodium (5:2) salt, chloroacetic acid, calcium (3:1) salt, chloroacetic acid, ammonium (2:1) salt, chloroacetic acid, potassium (2:1) salt, C006972, MCA, CAA

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2 comments


    1. Post author
      www.PrepChem.com

      Hi,

      Sulphur is catalyst in the chlorination reaction or sulphur reacts with chlorine yielding sulfur chloride (or dichloride) which is the chlorinating agent.

      2S + Cl2 → S2Cl2 (or SCl2)

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