Synthesis of oxalyl chloride

Preparation of oxalyl chloride

Oxalyl chloride is prepared by the action of phosphorus pentachloride on oxalic acid.

Preparation of oxalyl chloride

Preparation of oxalyl chloride

The oxalic acid must be dry or the yield of oxalyl chloride is cut down to a minimum. Drying may be achieved in an oven at 110° C for 6-8 hours, having the oxalic acid spread out in thin layer. During the drying the oxalic acid tends to cake and so must be broken up in a mortar from time to time.

To round bottom flask which is cooled with ice-water bath 90 g anhydrous powdered oxalic acid are mixed with 400 g of  pulverized phosphorus pentachloride. The mixture is allowed to stand for 2-3 days at the room temperature until the mass is completely liquefied. The reaction products is fractionally distilled by collecting fraction between 60 and 100 °C. By repeated distillation oxalyl chloride is obtained completely free from phosphorus oxychloride. The yield of final product is about 50% which is a colorless liquid, with boiling 64 °C.

The war gases chemistry and analysis, by M. Sartory, 79, 1939

IUPAC Name

oxalyl dichloride

InChI

InChI=1S/C2Cl2O2/c3-1(5)2(4)6

InChI Key

CTSLXHKWHWQRSH-UHFFFAOYSA-N

Canonical SMILES

C(=O)(C(=O)Cl)Cl

MeSH Synonyms

oxalyl chloride

Depositor-Supplied Synonyms

Oxalyl chloride, Ethanedioyl dichloride, Oxalyl dichloride, Oxalic dichloride, Oxaloyl chloride, 79-37-8, Oxalic acid dichloride, Ethanedioyl chloride, Oxalic acid chloride, oxalylchloride, (COCl)2, Oxalyl chloride (6CI,8CI), UNII-R4Y96317DW, CTSLXHKWHWQRSH-UHFFFAOYSA-N, EINECS 201-200-2, BRN 1361988, oxaloylchloride, oxalyichloride, oxalyl-chloride, oxalyldichloride, oxalyl chlori de, Oxalyl chloride solution, SCHEMBL112, ACMC-209ph8, AC1L23JB, O8801_ALDRICH, KSC379I2L, 75760_ALDRICH, 221015_ALDRICH, 310670_ALDRICH, 320420_ALDRICH, AC1Q3G44, AC1Q3G45, O8801_SIAL, 75760_FLUKA, CTK2H9425, MolPort-000-871-963, BB_SC-7090, R4Y96317DW, STR00129, alpha-oxo-alpha-chloroacetyl chloride, AN-656, ANW-37290, BBL011493, STL146605, AKOS000121192, BCP9001041, MCULE-7263932124, RP19720, RTR-037858, BP-30173, KB-79727, LS-65546, InChI=1/C2Cl2O2/c3-1(5)2(4), TR-037858, O0082, 6140-EP2269990A1, 6140-EP2270006A1, 6140-EP2270010A1, 6140-EP2270011A1, 6140-EP2270014A1, 6140-EP2272516A2, 6140-EP2272517A1, 6140-EP2272822A1, 6140-EP2272825A2, 6140-EP2272834A1, 6140-EP2272839A1, 6140-EP2272840A1, 6140-EP2272845A2, 6140-EP2275102A1, 6140-EP2275404A1, 6140-EP2275407A1, 6140-EP2275410A1, 6140-EP2275412A1, 6140-EP2275414A1, 6140-EP2277867A2, 6140-EP2277875A2, 6140-EP2277877A1, 6140-EP2277878A1, 6140-EP2279741A2, 6140-EP2280000A1, 6140-EP2280003A2, 6140-EP2280006A1, 6140-EP2280007A1, 6140-EP2281818A1, 6140-EP2284171A1, 6140-EP2286811A1, 6140-EP2286812A1, 6140-EP2287153A1, 6140-EP2287165A2, 6140-EP2287166A2, 6140-EP2289868A1, 6140-EP2289885A1, 6140-EP2289890A1, 6140-EP2289892A1, 6140-EP2289893A1, 6140-EP2289894A2, 6140-EP2292228A1, 6140-EP2292593A2, 6140-EP2292596A2, 6140-EP2292620A2, 6140-EP2292621A1, 6140-EP2295410A1, 6140-EP2295411A1, 6140-EP2295414A1, 6140-EP2295425A1, 6140-EP2295429A1, 6140-EP2295432A1, 6140-EP2298731A1, 6140-EP2298735A1, 6140-EP2298747A1, 6140-EP2298750A1, 6140-EP2298764A1, 6140-EP2298765A1, 6140-EP2298766A1, 6140-EP2298772A1, 6140-EP2298776A1, 6140-EP2298778A1, 6140-EP2298779A1, 6140-EP2301911A1, 6140-EP2301929A1, 6140-EP2301930A1, 6140-EP2301935A1, 6140-EP2305250A1, 6140-EP2305640A2, 6140-EP2305643A1, 6140-EP2305647A1, 6140-EP2305648A1, 6140-EP2305651A1, 6140-EP2305652A2, 6140-EP2305660A1, 6140-EP2305667A2, 6140-EP2305672A1, 6140-EP2305674A1, 6140-EP2305675A1, 6140-EP2305677A1, 6140-EP2305682A1, 6140-EP2305684A1, 6140-EP2305695A2, 6140-EP2305696A2, 6140-EP2305697A2, 6140-EP2305698A2, 6140-EP2308562A2, 6140-EP2308812A2, 6140-EP2308828A2, 6140-EP2308833A2, 6140-EP2308838A1, 6140-EP2308839A1, 6140-EP2308841A2, 6140-EP2308848A1, 6140-EP2308851A1, 6140-EP2308854A1, 6140-EP2308861A1, 6140-EP2308869A1, 6140-EP2308873A1, 6140-EP2308874A1, 6140-EP2308879A1, 6140-EP2308880A1, 6140-EP2311814A1, 6140-EP2311818A1, 6140-EP2311829A1, 6140-EP2311830A1, 6140-EP2314295A1, 6140-EP2314576A1, 6140-EP2314583A1, 6140-EP2314585A1, 6140-EP2314586A1, 6140-EP2314593A1, 6140-EP2316824A1, 6140-EP2316836A1, 6140-EP2371811A2, 6140-EP2374790A1, 19047-EP2280000A1, 19047-EP2292589A1, 19047-EP2295415A1, 19047-EP2298746A1, 19047-EP2305647A1, 19047-EP2308880A1, 19047-EP2314576A1, 102284-EP2272841A1, 102284-EP2280001A1, 102284-EP2280008A2, 102284-EP2292593A2, 102284-EP2295425A1, 102284-EP2298746A1, 102284-EP2301922A1, 3B4-1042, I14-5821

Removed Synonyms

CID65578, 4-02-00-01853 (Beilstein Handbook Reference)

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