Process for making menthyl glutarate

Details Process for making menthyl glutarate Process for making menthyl glutarate

2011-06-14

2011-06-14

Zucker, Paul A (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

07960580

ABSTRACT:
A process for making menthyl glutarate is disclosed. The process comprises reacting excess glutaric acid and menthol to produce a mixture comprising monomenthyl glutarate (MMG) and dimenthyl glutarate (DMG), wherein the weight ratio of glutaric acid to menthol is from 1.0 to 1.6 and the resulting mixture comprises from 60 to 70 wt. % of MMG and from 30 to 40 wt. % of DMG.

REFERENCES:
patent: 3111127 (1963-11-01), Jarboe
patent: 7247743 (2007-07-01), Erman et al.
patent: 2007/0248717 (2007-10-01), Johnson et al.
Hiserodt et al., “Identification of Monomenthyl Succinate, Monomenthyl Glutarate, and Dimenthyl Glutarate in Nature by High Performance Liquid Chromatography-Tandem Mass Spectrometry,”J. Agric. Food Chem. 52. (2004) 3536.
Hilditch, “The effect of Contiguous Unsaturated Groups on Optical Activity. Part III. The Normal Series of Fatty Dibasic Acids,”J. Chem. Soc., (1909) 1578.
Paris, et al.,“Glutaric Acid and Glutarimide,”Organic Synthesis, Coll. vol. 4, (1963) 496.
Dewis, “Molecules of Taste and Sensation,”Chemistry and Technology of Flavours and Fragrances, D. Rowe, ed., CRC Press, Boca Raton (2005) Ch. 9, pp. 199-243.

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