Benzene → Acetyl Tributyl Citrate

HRID 2186543

Reaction equation

HRID 2186543 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH:14]1[CH:19]=[CH:18][CH:17]=CC=1.[CH2:20]([OH:22])[CH3:21].[OH-].[K+]>[Sn].C(OCCCC)(=O)C.C(O)CCC>[CH3:17][CH2:18][CH2:19][CH2:14][O:10][C:9]([CH2:8][C:3]([O:4][C:20]([CH3:21])=[O:22])([C:5]([O:7][CH2:14][CH2:19][CH2:18][CH3:17])=[O:6])[CH2:2][C:1]([O:13][CH2:1][CH2:2][CH2:3][CH3:5])=[O:12])=[O:11]

Participants

8

Reactant 4

HCID 241BenzeneHCID 311Citric AcidHCID 702EthanolHCID 14797Potassium Hydroxide

Product 1

HCID 6505Acetyl Tributyl Citrate

Reagents, catalysts & solvents 3

HCID 5352426Tin atomCatalystHCID 2631-ButanolSolventHCID 31272Butyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

German Pat. No. 1 041 944 describes a process in which a citric acid ester is said to be prepared from a crude citric acid broth. Specifically, the authors describe a process for producing an ester of citric acid, in which a raw 30% citric acid broth is dehydrated with benzene and ethanol to a syrup. Butanol and butyl acetate, along with a tin catalyst, are added to the syrup and the mixture is heated to a temperature of 140-160° C., whereupon the reaction is halted with potassium hydroxide. The resulting reaction product is washed with sodium carbonate in water, and the crude mixture distilled. The authors report yielding acetyl tributyl citrate in the recovered material.

Workup

  1. customThe resulting reaction product
  2. washis washed with sodium carbonate in water
  3. distillationthe crude mixture distilled

Sources & evidence

ORD record
ord-bae6427c73664c1d8c019b4c4dc77073
Source dataset
uspto-grants-2002_06
Patent number
US06403825B1

Linked notes

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