Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1991-09-10
1994-03-22
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435135, 435136, C12P 742, C12P 752, C12P 740
Patent
active
052963632
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the preparation of 2-(4-hydroxyphenoxy)propionic acid.
2-(4-Hydroxyphenoxy)propionic acid is a valuable intermediate, in particular for the preparation of herbicides.
Chemical processes for the preparation of racemic and of pure enantiomeric forms of 2-(4-hydroxyphenoxy)propionic acid have been disclosed. These processes start from hydroquinone and have the disadvantage that they give by-products whose removal, which is necessary, is laborious. This makes economic preparation impossible.
It has been disclosed that microorganisms are able to hydroxylate aromatic compounds. This usually produces dihydroxylated compounds or mixtures of various regioisomers (R. J. W. Byrde, D. Woodcook, Biochem. J. 65 (1957) 682).
The regioselective oxidation of 2-phenoxypropionic acid to 2-(4-hydroxyphenoxy)propionic acid by microorganisms has not hitherto been disclosed.
We have now found, surprisingly, that various microorganisms oxidize the valuable 2-phenoxypropionic acid to 2-(4-hydroxyphenoxy)propionic acid with high regioselectivity.
The present invention relates to a process for the preparation of 2-(4-hydroxyphenoxy)propionic acid by fermentation, which comprises oxidizing 2-phenoxypropionic acid or salts thereof under aerobic conditions in the presence of a microorganism.
A large number of microorganisms are suitable for the process, in particular fungi and bacteria. Utilizable fungi can be isolated, for example, from soil samples, in particular humus-containing soil samples. Particularly suitable for the reaction are Aspergillus niger strains. Also suitable are many fungi from the genera Beauveria, Paecilomyces, Sclerotium and Coprinus, which can be obtained, for example, from collections of strains and whose suitability for the hydroxylation can be determined in a straightforward preliminary test. Suitable bacteria can also be isolated from soil samples, inter alia. Particularly suitable bacteria are Streptomyces strains.
To carry out the process according to the invention, suitable strains are transferred to a nutrient medium containing 2-phenoxypropionic acid and incubated aerobically therein under conditions favorable for growth and production by the particular microorganism. The fermentation is carried out continuously or batchwise for 1 to 10 days.
The cells of the microorganism, which can also be used in the form of dormant, non-growing cells, are allowed to act directly on the substrate. All conventional incubation processes can be employed, but particularly preferred fermenters are in the form of deep, aerated and agitated tanks. Very good results are obtained by incubation of a liquid nutrient medium.
Suitable nutrient media contain sources of carbon and of nitrogen, and inorganic salts and, where appropriate, small amounts of trace elements and vitamins. Sources of nitrogen which can be used are inorganic or organic nitrogen compounds or materials which contain these compounds. Examples are ammonium salts, nitrates, corn steep liquor, brewer's yeast autolysate, soybean meal, wheat gluten, yeast extract, yeast, urea and potato protein. Examples of sources of carbon which can be used are sugars such as glucose, polyols such as glycerol, or fats such as soybean oil.
Examples of inorganic salts are the salts of calcium, magnesium, manganese,, potassium, zinc, copper, iron and other metals. A particularly suitable anion in the salts is the phosphate ion. Growth factors may be added to the nutrient medium, such as biotin, riboflavin or other vitamins.
The ratios of the said nutrients in the mixture depends on the type of fermentation and will be determined in the individual case.
Generally suitable for carrying out the process according to the invention are phenoxypropionic acid concentrations of about 1 to 100 g/l, preferably about 5 to 50 g/l.
The culture conditions are chosen so that the best possible yields are achieved. Cultivation is preferably carried out at from 20.degree. to 40.degree. C., particularly advantageously from 25.degree. to 30.degree. C. The p
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Fungal Detoxication, Byrde et al., Biochemical Journal 65 (1975) pp. 682-686.
Cooper Bryan
Hauer Bernhard
Ladner Wolgang
Siegel Hardo
Base Aktiengesellschaft
Lilling Herbert J.
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