Citric Acid → Itaconic acid

HRID 2275482Notes

Reaction equation

HRID 2275482 reaction equation
O.C(O)(=O)[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])O.[H][H].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>OCC(CO)O>[C:6]([OH:8])(=[O:7])[C:4]([CH2:9][C:10]([OH:12])=[O:11])=[CH2:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 178418361HCID 178418361, compound

Product 1

HCID 811Itaconic acid

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
204 °C

Procedure

The process of WO2010/059925 was reworked as follows (derived from Examples 1 and 12): 20 grams of glycerol reagent grade and 40 grams of citric acid monohydrate were mixed The mixture was brought under nitrogen to a temperature of 140° C. while stirring, and kept under nitrogen at that temperature for a period of one hour. The resulting prepolymer was heated to 204° C. for a period of one hour. Uncontrollable foaming took place resulting in an inhomogeneous foam. The material discolored to yellow and had poor mechanical properties. Combustion analysis showed a carbon content of 43.76% and a hydrogen content of 5.56%, showing that about 5-10% of the citric acid decarboxylated to form itaconic acid.

Workup

  1. customwas brought under nitrogen to a temperature of 140° C.
  2. customresulting in an inhomogeneous foam

Sources & evidence

ORD record
ord-09e8405abc144d9995e9ed39f9909a69
Source dataset
uspto-grants-2015_09
Patent number
US09127120B2

Reaction notes

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