Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing sulfur-containing organic compound
Patent
1990-11-23
1993-08-31
Schwartz, Richard A.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing sulfur-containing organic compound
435156, 435171, 435135, C12P 102, C12P 762, C12P 722, C12P 1100
Patent
active
052408361
DESCRIPTION:
BRIEF SUMMARY
This invention relates to methylation of organic compounds.
At present the industrial esterification of carboxylic acids to form the methyl ester is normally effected by refluxing the carboxylic acid with methanol in the presence of mineral acid and separating the ester from the reaction mixture by fractional distillation. Methylation of phenols to form anisoles is normally performed industrially by refluxing dimethyl sulphate with the sodium salt of the phenol. The resulting anisole is separated from the reaction mixture by solvent extraction or distillation techniques. Both methylation of carboxylic acids and of phenols is therefore energy and capital intensive.
The object of the present invention is to provide a cheaper method of methylation.
According to the invention there is provided a method of methylation characterised in that an organic substance that is to be methylated is contacted with a methyl donor material in the presence of fungus or another organism into which an appropriate fungal gene is introduced.
The invention, therefore, is a biological system and it offers the possibility of preparation of methylated compounds at ambient temperatures using a gaseous halomethane. It is believed that this system is potentially cheaper to operate than the known techniques.
In a preferred embodiment of the invention a fungal preparation or immobilised enzyme preparation is produced using an appropriate fungus preferably selected from fungi which can biosynthesise chloromethane such as the Hymenochaetaceae, Polyporaceae and Corticiacae. Alternatively the invention employs an immobilised preparation of a bacteria into which a cloned copy of the fungal gene, or genes, coding for the methylation system has been introduced using standard genetic manipulation techniques. An aqueous solution of the organic substance to be methylated, for example a carboxylic acid or a phenol containing dissolved gaseous chloromethane are together cycled through the preparation. Insoluble methyl ester of the carboxylic acid or O-methyl phenol as the case may be, is formed and can be separated and the unreacted mixture re-cycled through the preparation. Additional starting materials can be added as necessary to the recycle stream.
The reaction is carried out at ambient temperature for example between 15.degree. and 25.degree. C. and preferably at a pH between 2 and 8.
The invention can be applied to a wide range of organic substances, particularly acids such as benzoic, furoic, phenylacetic, cinnamic, propionic, butyric, isobutyric, valeric, isovaleric, hexanoic and heptanoic acids and halo-, methyl and hydroxy-, methoxy- and cyano- substituted derivatives of acids.
The invention can also be applied to the methylation of many phenols and thiophenols including both halo- and methyl substituted compounds such as 2-, 3- and 4- fluorophenol, 2-, 3- and 4- chlorophenol, 2, 6- dichlorophenol, 2-, 3- and 4- bromophenol, 2-iodophenol and 2-, 3- and 4- methylphenol.
The methyl donor material may be a halo methane such as chloro-, bromo- or iodo-methane. As mentioned above a gaseous donor material is preferably used.
The following Examples further illustrate the invention.
EXAMPLE 1
The fungus Phellinus pomaceus (NCWRF.FPRL 33A obtained from the National Collection of Wood Rotting Fungi, Princes Risborough Laboratory, Building Research Establishment, Aylesbury, Bucks., England, or CBS 137.42 obtained from the Centraalbureau Voor Schimmelcultures, Baarn, The Netherlands, was used as a basis of the system.
A 2 mM solution of butyric acid containing 0.1 mM chloromethane buffered at pH 4.0 with 20 mM citrate buffer was incubated with 0.035 g of fungal mycelium for a period of 12 hours at a temperature of 25.degree. C. Methyl butyrate was formed at a rate of 245 nanomoles/g fungal mycelium/hour.
EXAMPLE 2
A 0.5 mM solution of benzoic acid containing 1.23 mM chloromethane and buffered at pH 4.0 with 20 mM citrate buffer was incubated with 0.035 g of fungal mycelium (Phellinus pomaceus, NCWRF.FPRL 33A or CBS 137.42) for a period of 12 hour
REFERENCES:
Harper, Science, 315: 55-57 (1985).
Harper et al., J. Gen. Microbiol., 132: 1231-1246 (1986).
Harper et al., J. Gen. Microbiol., 134: 2831-2839 (1988).
Schwartz Richard A.
The Queen's University of Belfast
Vogel Nancy T.
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