Citric acid and citramalic acid preparation

Details Citric acid and citramalic acid preparation Citric acid and citramalic acid preparation

1976-04-26

1977-05-10

Raymond, Richard L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260535P, C07B 300

Patent

active

040228231

ABSTRACT:
A process for the preparation of citric acid which comprises contacting an unsaturated compound selected from 3-methylene-1,5-pentanediol and its esters with a nitric acid solution in an amount of 2 to 50 mols of nitric acid feed per mol of unsaturated compound feed, and at least 0.005 mol percent nitrogen dioxide based on nitric acid, at a temperature between -10.degree. and 120.degree. C., to thereby oxidize said unsaturated compound to citric acid. Preferably the contacting of the unsaturated compound so as to synthesize citric acid is carried out in the absence of any substantial amount of vanadium as the presence of vanadium catalysts has been found to effectively prevent the recovery of good yields of citric acid from the process.
The citric acid synthesis preferably is carried out by an overall process wherein isobutene is reacted with two mols of formaldehyde to produce 3-methylene-1,5-pentanediol, which is then converted to citric acid by reaction with nitrogen dioxide
itric acid.
Citramalic production from 3-methyl-3-buten-1-ol is also disclosed.

REFERENCES:
patent: 2847464 (1958-08-01), Robertson et al.
patent: 2867657 (1959-01-01), Selwitz
patent: 35171059 (1970-06-01), Volker et al.
"Nitrogen Teroxide", Hercules bulletin (1968) pp. 34-61.

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