Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1998-04-27
2000-12-19
Zitomer, Fred
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435128, 435183, 435191, 435227, C12P 740
Patent
active
061626244
DESCRIPTION:
BRIEF SUMMARY
This invention relates to processes for making aqueous solutions of ammonium acrylate and other acrylic monomers.
There is a major industrial need to produce aqueous acrylic acid, or a water soluble salt thereof such as ammonium acrylate or sodium acrylate, for instance for use as a polymerisable monomer. It is necessary that the aqueous solution should be as free as possible of impurities which are undersirable either from an environmental point of view or because they might interfere with subsequent polymerisation.
One common way of making acrylic acid industrially comprises hydrolysing acrylonitrile to form acrylamide and then hydrolysing the acrylamide to form ammonium acrylate or acrylic acid. Although most commercial processes of this type rely upon chemical hydrolysis, enzymatic hydrolysis is known for each stage (ie nitrile hydratase for converting nitrile to amide and amidase for converting amide to acid salt). The manufacture of acrylic acid by this technique is economically inconvenient, for instance because it requires an extensive amount of equipment for the two stages. Also extensive purification procedures are generally required. For instance it is essential to remove impurity amounts of acrylonitrile to very low levels and this may necessitate extensive distillation.
Another commonly used process for making acrylic acid is by hydration of propylene oxide. This avoids the need to conduct purification procedures in order to eliminate any acrylonitrile contamination but has the disadvantage that the process has to be conducted in complex, generally pressurised, apparatus.
There have been a few proposals in the literature for use of a nitrilase enzyme for converting aqueous acrylonitrile direct to aqueous ammonium acrylate. It is generally accepted that the direct conversion is more effective on aromatic than aliphatic nitriles, eg Stevenson et al, Biotech. and Appl. Biochem. 15, 283-302 (1992).
In one example of EP-A-444640 acrylonitrile at a concentration of below 200 mM was hydrolysed using nitrilase catalyst to achieve almost quantitative conversion to acrylic acid, together with some acrylamide contamination.
In JP-B-632596 a 2% acrylonitrile solution is utilised in one example and in another example a 25% acrylonitrile solution is hydrolysed to a 32.9% ammonium acrylate solution. In a further example a 15% (meth) acrylonitrile solution is utilised to give a 23% ammonium (meth) acrylate solution.
In Biotech and Appl Biochem 11, 581 to 601 (1989) it is stated that the particular enzyme discussed in that article has Km for acrylonitrile of 17 mM. No process conditions are given but this value necessarily indicates that a substantial amount of acrylonitrile will remain in the product. The article indicates the 4-6% acrylamide is formed. The same article also indicates that the enzyme discussed in that article has a much higher activity for benzonitrile than for acrylonitrile.
In J Bacteriol September 1990 page 4807 to 4815 the properties of R rhodochrous K22 are analysed and it is stated that this has Km for acrylonitrile of 1.14 mM. This value also indicates the necessary presence of substantial amounts of acrylonitrile in the end product. There is no information given as to the concentration of ammonium acrylate which can be obtained but the article does note that enzyme activity is rapidly lost at above 55.degree. C.
In Appl Microbiol Biotech 1990, 34, pages 322 to 324 a fed batch process of converting acrylonitrile to acrylic acid is described. The acrylonitrile has to be kept at a concentration below 200 mM (1.06%) and the product is said to contain 38% acrylic acid after 24 hours. The products were extracted by solvent extraction followed by evaporation and distillation.
These enzymic conversion processes provide a useful alternative to the two step enzymatic conversion (ie acrylonitrile to acrylamide and then acrylamide to ammonium acrylate) and the chemical conversion process, but all retain the requirement for extensive purification procedures to reduce acrylonitrile levels.
Accordin
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Hughes Jonathan
Symes Kenneth Charles
Ciba Specialty Chemicals Water Treatments Limited
Crichton David R.
Zitomer Fred
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