Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Specific organic component
Patent
1995-05-31
1997-10-07
Lieberman, Paul
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
Specific organic component
510392, 435 74, 435174, 536 41, C11D 322, C12N 914
Patent
active
056748302
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the manufacture of alkylglycoside esters, in which an alkylglycoside and an acyl group donor are contacted with an enzyme catalyst.
Such a process is known from e.g. PCT patent applications WO-B-8901480 and WO-B-9009451, as well as from Synthesis, February 1990, pp. 112-115 and J. Chem. Soc., Chem. Commum., 1989, pp. 934-935.
In these publications, processes are described for the enzyme catalysed preparation of 6-0-acylglucopyranosides by simply mixing the starting alkylglycoside with a fatty acid at 70.degree. C. in the presence of an immobilized lipase. The water generated in the reaction is removed in vacuo. In this way, using a species of Candida antarctica, yields of 85-95% of the 6-0-monoesters were obtained. Although a suitable solvent, such as hexane or acetonitrile may be used, such solvent will generally inactivate the enzyme, and they are toxic, which is detrimental to the environment and requires a thorough purification of the end product, if this has to be used in food or cosmetic applications.
A problem in the processes thus described is the high viscosity of the alkylglycoside, which needs to be mixed with the molten fatty acid, which is very difficult and increases the total reaction time considerably. Also if the amount of acyl donor is increased relative to the alkylglycoside to increase the reaction efficiency, by-products, such as diesters tend to be formed in appreciable amounts.
There is therefore still a need for a process for the manufacture of alkylglycoside esters having a high monoester content at a high reaction rate, without the problems as outlined above.
It is an object of the present invention to provide a process for the manufacture of alkylglycoside esters, in which an alkylglycoside and an acyl group donor are contacted with an enzyme catalyst, in which in a relatively short time alkylglycoside monoesters of high purity are formed.
During extensive investigations it has been found that if the alkylglycoside and the acyl donor are mixed with a surface active material, preferably with an effective amount of the alkylglycoside ester formed, a stable micro-emulsion is formed, which is very easy to handle throughout the whole manufacturing process. By "a micro-emulsion" is understood throughout this specification and the attached claims a dispersed system stabilized by surfactants which could be micellar systems or true micro-emulsions. By changing the ratio of acyl donor to alkylglycoside it appeared to be possible to control the viscosity of the micro-emulsion, whereas the stability of the micro-emulsion could be controlled by the amount and (to a lesser extent) the type of surface-active material used. A molar ratio of acyl donor to alkylglycoside of 1.0-2.0 moles of acyl donor per mole of alkylglycoside is preferred.
It has been stated in U.S. Pat. No. 4,614,718 (Seino et al.) that sugar or sugar-alcohol fatty acid esters have been prepared by dispersing a lower alkyl ester of a fatty acid in a solution of sugar in a solvent, such as propylene glycol or water, with the aid of an emulsifier, such as soap, after which the solvent is removed before the transesterification reaction is started. This process is said to be known as the "microemulsion process" (see U.S. Pat. No. 4,614,718, Column 1, lines 17-22). This is a non-enzymatic process, however, and Seino et al. clearly state that this method exhibits serious disadvantages, such as the high reaction temperature, leading to discoloration and the use of solvents. The "micro-emulsion process" has been described in detail in Journal of the American Oil Chemists' Society, Volume 44, No. 5 (May 1967), 307-309. In this publication it has been described how sucrose dissolved in propylene glycol, methyl stearate, sodium stearate and potassium carbonate catalyst are combined to form a transparent micro-emulsion. On page 309 it has been stated that this micro-emulsion is formed at 130.degree.-135.degree. C., and that the micro-emulsion is not stable at room temperature.
In the process a
REFERENCES:
patent: 4614718 (1986-09-01), Seino et al.
patent: 4839287 (1989-06-01), Holmberg et al.
patent: 4959459 (1990-09-01), David et al.
patent: 5200328 (1993-04-01), Kirk et al.
Brenkman Tanja
Macrae Alasdair R.
Moss Richard E.
Fries Kery A.
Lieberman Paul
Unichema Chemie B.V.
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