Purification process by decomposition of haloalkanolic acid with

Details Purification process by decomposition of haloalkanolic acid with Purification process by decomposition of haloalkanolic acid with

1994-11-21

1996-05-21

Lilling, Herbert J.

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

Organic compounds

Carbohydrates or derivatives

435128, 435129, 435130, 435132, 435135, 435195, 435262, 435264, 25217412, 25217421, 25217422, 25218311, 252DIG1, 536 76, 536 82, 536 98, 562512, C08B 1120, C08G 6532, C12P 742, C07C32352

Patent

active

055191304

DESCRIPTION:

BRIEF SUMMARY
THIS INVENTION relates to a purification process.
In industrial processes materials may be encountered which contain unwanted haloalkanoic acids which contain 2 to 6 for example 2 to 4 carbon atoms or amides or esters thereof in which at least one carbon atom especially the .alpha.-carbon atom is bound to a halogen, especially chlorine, atom, which materials preferably contain only one halogen atom (herein referred to as HAAs), for example chloroacetic acid.
We have found that dehalogenase enzymes, especially those derived from Pseudomonas are remarkably effective in decomposing such substances in the presence of high concentrations of carboxymethyl cellulose, surface active agents and thioglycollic acid salts, in for example concentrations of 5%, 10% or more for example. 50% or more in water, all percentages being by weight.
Certain surface active agents (surfactants) are made by processes which comprise reacting active hydrogen atoms with haloalkanoic acids or esters or amides thereof as aforesaid. Such surface active agents may comprise carboxy alkyl groups or esters or amides thereof, for example groups of formula R(AO).sub.n OZCOOH in which R is an alkyl phenyl or preferably alkyl group containing 8 to 20 and preferably 9 to 18 carbon atoms, n has a value of 1 to 20 and preferably 11/2 to 20 and is preferably 2 to 12 and represents an average value, AO is one or more alkylene oxide groups which preferably comprise ethylene and/or propylene oxide groups and may consist essentially of such groups, and Z is an alkylene group having 1 to 4 carbon atoms, for example a CH.sub.2 group. Residues of the HAAs may remain in the product as an impurity however and it may be desired to remove them.
The invention comprises a process in which free haloalkanoic acids or esters or amides thereof as aforesaid are decomposed in the presence of a surfactant which comprises a carboxyalkyl group or an ester or amide thereof, carboxymethyl cellulose or of a thioglycollic acid salt by contacting it with a dehalogenase enzyme which may be a dehydrohalogenase enzyme.
The process is suitably carried out at a pH of 6 to 9 the temperature is suitably 15.degree.-40.degree. C.
Sufficient enzyme is preferably present to enable the process to be completed within two days. The rate may be increased by increasing the quantity of enzyme present, and the process may be completed more rapidly by this means.
The invention also comprises a process of producing a surfactant a thioglycollic acid salt or carboxymethyl cellulose which comprises reacting a substance having reactive hydrogen atoms with a haloalkanoic acid to form a carboxyalkyl derivative thereof and decomposing residual haloalkanoic acid in the product by contacting the product with a dehydrohalogenase enzyme.
If desired, small quantities of enzyme may be added to the relevant products before they are distributed and the decomposition of haloalkanoic acid may proceed during transport or storage of the product.
The enzyme may be produced using a bacterium which may belong to any genus but is suitably a strain of Pseudomonas, especially a strain of the species Pseudomonas putida or Pseudomonas fluorescens, preferably Pseudomonas putida NCIMB 12018.
5 stains of bacteria which can be used as sources from which the enzyme composition may be isolated have been deposited at the National Collection of Industrial and Marine Bacteria, PO Box 31, 135 Abbey Road, Aberdeen, Scotland, UK, and have been assigned the following accession numbers:


______________________________________ Deposited ______________________________________ 1 Pseudomonas putida NCIMB 12018 20.09.1984 2 Pseudomonas fluorescens NCIMB 12159 30.09.1985 3 NCIB 12160 30.09.1985 4 NCIB 12161 30.09.1985 5 Pseudomonas putida NCIB 12158 30.09.1985 ______________________________________
The enzyme may be isolated from bacteria, for example P. putida NCIB 12018, by techniques well known on the enzyme art, e.g. absorption, elution, and precipitation techniques. For example, cells of a suitable organism may be

REFERENCES:
patent: 4804629 (1989-02-01), Roy
patent: 5322782 (1994-06-01), Nakajima et al.
patent: 5372944 (1994-12-01), Swanson

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