Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1994-01-21
1995-08-29
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568671, 568691, 568698, 568650, 568680, C06C 4100, C06C 4300
Patent
active
054462100
DESCRIPTION:
BRIEF SUMMARY
This application is 371 of PCT/EP92/01587 filed Jul. 13, 1992.
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for the production of polyol ethers by catalytic reaction of mixtures of polyols and carbonyl compounds with hydrogen at elevated temperatures and under elevated pressure.
2. Statement of Related Art
Ethers of polyols, for example glycerol ethers, are surface-active substances which have excellent detergent properties and which may be used, for example, as wetting agents (U.S. Pat. No. 2,932,670), emulsifiers (DE 11 00 035 A1)] or lime soap dispersants (U.S. Pat. No. 3,350,460).
Polyol ethers are generally produced by WILLIAMSON'S ether synthesis. In this process, polyols, for example glycerol, are reacted with alkyl halides in the presence of strong bases. According to DE-PS 615 171, alkali metal salts of alkyl sulfates may be used instead of the alkyl halides.
However, the known processes mentioned above all have the disadvantage that the production of the polyol ethers is accompanied by the accumulation of salts, for example potassium chloride or sodium sulfate, which cannot remain in the product, but instead have to be removed--in some cases with considerable effort.
Another serious disadvantage is that these salts are by no means pure, but instead are contaminated with significant quantities of product. Accordingly, the disposal of these waste materials is extremely expensive and adversely affects the profitability of the process.
Accordingly, the problem addressed by the present invention was to provide a process for the production of polyol ethers which would be free from the disadvantages mentioned above.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of polyol ethers which is characterized in that mixtures containing hydrogen or aliphatic hydrocarbon radicals containing 1 to 22 carbon atoms and 0, 1, 2 or 3 double bonds, pressure in the presence of a catalyst which is insoluble in the reaction mixture.
It has surprisingly been found that polyol ethers can be produced without the formation of salts as secondary products providing the polyols are reacted with aldehydes or ketones and the acetals or ketals intermediately formed are simultaneously subjected, i.e. without isolation, to catalytic hydrogenation.
Polyols are compounds which contain at least two hydroxy groups. Typical examples are ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycols having an average molecular weight of 300 to 1500, propylene glycol, polypropylene glycols having an average molecular weight of 300 to 1500, propane-1,2diol, propane-1,3-diol, butane-1,2-diol, butane-1,4-diol, average molecular weight of 300 to 1500, propane-1,2diol, propane-1,3-diol, butane-1,2-diol, butane-1,4-diol, glycerol, monoesters of glycerol with C.sub.6-22 fatty acids, diglycerol, oligoglycerols with an average degree of condensation of 3 to 10, trimethylol propane or pentaerythritol. It is particularly preferred to use glycerol.
The carbonyl compounds corresponding to formula (I) are known aldehydes and ketones which may be prepared by methods known per se. Carbonyl compounds corresponding to formula (I), in which R.sup.1 and R.sup.2 independently of one another represent C.sub.1-18 alkyl groups, are preferably used.
Typical aldehydes are, for example, formaldehyde, acetaldehyde, acrolein, propionaldehyde, butyraldehyde, croton aldehyde, caproic aldehyde, caprylic aldehyde, capric aldehyde, lauryl aldehyde, myristyl aldehyde, cetyl aldehyde, stearyl aldehyde, oleyl aldehyde, elaidyl aldehyde, linolyl aldehyde, linolenyl aldehyde, behenyl aldehyde or erucyl aldehyde.
Typical ketones are, for example, acetone and the various position isomers of butanone, pentanone, hexanone and octanone and also the fatty ketones obtained by pyrolysis of the alkaline earth metal salts of C.sub.12-22 fatty acids. It is particularly preferred to use acetone.
The polyols and the carbonyl compounds may be used in a molar ratio of 5:1 to 1:5 and pre
REFERENCES:
patent: 2932670 (1960-04-01), Blake
patent: 3350460 (1967-10-01), Lamberti
patent: 4088700 (1978-05-01), Watts
patent: 4479017 (1984-10-01), Ayusawa et al.
patent: 4484009 (1984-11-01), Ghenassia et al.
Verzele et al, J Chem Soc (1963) pp. 5598-5600.
Assman Georg
Hees Udo
Schuster Fritz
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
Richter Johann
Szoke Ernest G.
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