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Cyclic alkyl alcohols and alcohol mixtures, their derivatives and use

IP.com Disclosure Number: IPCOM000030464D
Publication Date: 2004-Aug-16

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Madelein vd Merwe: ATTORNEY [+3]

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Abstract

Linear, saturated fatty alcohols of the chain lengths C8 to C22 can be obtained from natural fats and oils by hydrolysis or methanolysis followed by hydrogenation of the resultant acids or methyl esters. Even longer-chained, linear saturated fatty alcohols C22 to C40 are present in natural waxes, e.g. in beeswax or also in lignite waxes. Petro-chemically linear, saturated fatty alcohols in the C6 to C20 chain length range can be obtained by the Ziegler process from aluminum, hydrogen and ethylene. In addition, by ethylene polymerization and conversion of the obtained ALPHA-olefins, alcohols or acids with chain lengths in the range C20 to C60 can be produced (Unilin alcohols and acids).

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Cyclic alkyl alcohols and alcohol mixtures, their derivatives and use

SASOL GERMANY GmbH

Dr. Dirk Schär

SASOL

NORTH AMERICA

Charles Hammond

Linear, saturated fatty alcohols of the chain lengths C8 to C22 can be obtained from natural fats and oils by hydrolysis or methanolysis followed by hydrogenation of the resultant acids or methyl esters. Even longer-chained, linear saturated fatty alcohols C22 to C40 are present in natural waxes, e.g. in beeswax or also in lignite waxes. Petro-chemically linear, saturated fatty alcohols in the C6 to C20 chain length range can be obtained by the Ziegler process from aluminum, hydrogen and ethylene. In addition, by ethylene polymerization and conversion of the obtained a-olefins, alcohols or acids with chain lengths in the range C20 to C60 can be produced (Unilin alcohols and acids).

Semi-linear fatty alcohols such as Neodol® alcohols can be synthesized by ethylene oligomerisation followed by selective hydroformylation of the obtained a-olefins. Such modified oxo-alcohols (mO-alcohols) have a content of primary, linear, and saturated alcohols of approx. 80%.

The conventional oxo-alcohols (O-alcohols) are generally produced on the basis of kerosene. Here, the paraffin flow is isolated, dehydrogenated to olefins, and subsequently hydroformylated. The fatty alcohols obtained by this process contain approximately 50% primary, linear, and saturated fatty alcohols. It is known that this product flow can be split into linear and branched portions.

In addition to these generally mono branched fatty alcohols, multiple branched fatty alcohols are also known. Such fatty alcohols are obtained by oligomerization of propene and/or butenes. Normal chain lengths for such alcohols are C6 to C15 (e.g. isononanol, isodecanol and isotridecanol).

A new class of fatty alcohols became accessible by the hydroformylation of olefins that are obtained in the Fischer-Tropsch (FT) process from synthesis gas. In contrast to known fatty alcohols these FT fatty alcohols have structural isomers specialties. The average isomeric alcohol content is approx. 50% the same as the isomeric alcohol content for the conventional oxoalcohols, but as with oxoalcohol the isomeric alcohol is not derived from branching that occurs in the 2- or 3-position in relation to the hydroxyl group.

Table 1

Structure of oxoalcohols

                                               O- Alcohols                         mO- Alcohols                       FT- Alcohols

Linear Alcohols                         ~45%                                        ~80%                                     ~50%

Branched Alcohols                   ~55%                                        ~20%                                     ~50%

   R-CH2-CH2-OH                      ~45%                              ...