Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-01-22
1998-08-11
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536120, 536124, 510108, 510470, C07H 100, C07H 1504, C11D 322
Patent
active
057928436
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for the production of alkyl and/or alkenyl oligoglucosides, in which glucose of a selected particle size is subjected to acidic acetalization with fatty alcohols in known manner, and to the use of this glucose for the production of alkyl and/or alkenyl oligoglucosides.
2. Statement of Related Art
Alkyl oligoglycosides, more particularly alkyl oligoglucosides, are nonionic surfactants which are acquiring increasing significance by virtue of their excellent detergent properties and their high ecotoxico-logical compatibility. The production and use of these substances have been described just recently in a number of synoptic articles, of which the articles by H. Hensen in Skin Care Forum, 1, (October 1992), D. Balzer and N. Ripke in Seifen-Ole-Fette-Wachse 118, 894 (1992) and B. Brancq in Seifen-Ole-Fette-Wachse 118, 905 (1992) are cited as examples.
They are normally produced from glucose which is acetalized with fatty alcohols in the presence of acidic catalysts. The catalyst is then neutralized, excess fatty alcohol is removed and the product is bleached.
Basically, acids are used as catalysts for the acetalization. Sulfuric acid, for example, is extremely effective in the condensation, but always leads to very dark-colored products which are difficult or impossible to lighten. In addition, a high content of unwanted secondary products, particularly polyglucose, is observed.
In the past, there has been no shortage of proposals for suitable acidic catalysts which it was hoped would control product distribution and, in particular, the reaction rate. For example, it is known from EP-B1 0 132 043 and EP-B1 0 132 046 (Procter & Gamble) that p-toluene sulfonic acid and, in particular, anionic surfactants in acidic form, such as for example long-chain alkylbenzene sulfonic acids, alkyl sulfonic acids and sulfuric acid semiesters of fatty alcohols and polyglycol ethers thereof, are suitable for this purpose. Similarly, U.S. Pat. No. 5,003,057 (Henkel Corp.) describes the use of naphthalene sulfonic acid. Finally, the acetalization of sugars in the presence of sulfosuccinic acid is known from EP-A 0 415 192.
However, all these known processes have the disadvantage that the reaction rate is still unsatisfactory compared with other industrial processes and results in long reactor possession times which adversely affect the economy of the process. In addition, experience has shown that the length of the reaction time gives rise to a deterioration in color quality, so that a reduction in the reaction time is desirable for this reason, too. So far as product distribution is concerned, the choice of the catalyst acid has proved to be of little relevance.
Accordingly, the problem addressed by the present invention was to provide an improved process for the production of alkyl and/or alkenyl oligoglucosides which would be free from the disadvantages mentioned above.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of alkyl and/or alkenyl oligoglucosides, in which glucose having a particle size distribution of at least 70% in the 20 to 300 .mu.m range and preferably 90% in the 20 to 200 .mu.m range is subjected to acidic acetalization with fatty alcohols in known manner.
It has surprisingly been found that the particle size of the glucose has a considerable bearing on the rate of the acetalization reaction and hence on color quality. At the same time, the process according to the invention significantly improves the selectivity of acetalization by increasing the percentage content of monoglucosides and reducing the percentage content of higher oligomers.
The invention includes the observation that glucose having a broad particle size distribution in the 20 to 200 .mu.m range shows an optimal reaction rate so far as typical evaporation capacities are concerned.
In addition, it has proved to be of advantage in the process according to the invention to use glucose of a quality which comprises
REFERENCES:
patent: 5536431 (1996-07-01), Carduck et al.
Eskuchen Rainer
Schulz Paul
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Kight John
Lee Howard C.
Millson Jr. Henry E.
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