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Hydrochloric Acid → Gamma-Butyrolactone

HRID 34887
Notes
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Reaction equation

HRID 34887 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][CH2:2]1.[C:7]([Cl:10])(Cl)=[O:8].[ClH:11]>[Cl-].C[N+](C)(C)CC1C=CC=CC=1>[Cl:11][CH2:3][CH2:2][CH2:1][C:7]([Cl:10])=[O:8].[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6371Phosgene3×HCID 7302Gamma-Butyrolactone

Product 2

HCID 7302Gamma-ButyrolactoneHCID 783704-Chlorobutyryl chloride

Reagents, catalysts & solvents 1

HCID 5963Benzyltrimethylammonium chloride
Catalyst

Conditions

Temperature
130 °C

Procedure

430 parts of 4-butyrolactone and 47 parts of trimethylbenzylammonium chloride are initially taken in a 1 l stirred reactor which is equipped with a thermometer, inlet tubes for phosgene and hydrogen chloride and 2 low-temperature coolers set at -20° C. and -70° C. respectively. The mixture is heated to 130° C. 560 parts of phosgene and 120 parts of hydrogen chloride are passed in over 5.5 hours. Thereafter, nitrogen is passed in until the reaction mixture no longer contains any phosgene. Working up by distillation gives 620 g of 4-chlorobutyryl chloride and 30.5 g of butyrolactone. The distillation residue of 75 g, which consists of the catalyst and chlorobutyroyloxybutyryl chloride, can be reused for further batches. The yield of 4-chlorobutyryl chloride is 88 mol %, based on butyrolactone used.

Workup

  1. customset at -20° C. and -70° C.
  2. customare passed in over 5.5 hours
  3. distillationWorking up by distillation

Sources & evidence

ORD record
ord-6b818966f76a4387b4c35f6e99b7421f
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764309

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes