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Branched alcohols and alcohol mixtures, their derivatives and use obtained from FT-feed stocks

IP.com Disclosure Number: IPCOM000030465D
Publication Date: 2004-Aug-16

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Abstract

Alcohol mixtures (branched FT-alcohols) containing alcohols of the formula RCH2OH, wherein R1 is defined as R-CH2-radical of the compound RCH2OH and (a) from more than 0 to 20% by mass of the alcohols with a hydrocarbon radical R are linear and aliphatic, preferably saturated, and comprise on the average 4 to 40, preferably 7 to 16, and more preferably 10 to 15 carbon atoms, (b)from more than 20 to 95% by mass of the alcohols with a hydrocarbon radical R comprising on the average 4 to 20, preferably 7 to 12 carbon atoms, and up to 3, preferably 1 or 2 tertiary carbon atoms, are aliphatic, preferably saturated, and none of the tertiary carbon atoms occurs in the 2- or 3-position in relation to the -OH group of the alcohol, wherein at least 80%, preferably at least 95% of all the tertiary carbon atoms in the mixture, are not directly adjacent, wherein preferably the tertiary carbon atoms, insofar as these are substituted with alkyl groups, the alkyl groups at more than 70% of all alkyl-branches of the mixture, preferably more than 80%, are methyl and/or ethyl and/or propyl groups, preferably methyl and/or ethyl groups, more preferably methyl groups, and (c) up to 40% by mass, preferably 25% by mass, and more preferably 15% are other alcohols, with on the average 4 to 40, preferably 7 to 16, and more preferably 10 to 15 carbon atoms,wherein the radicals R according to (a), (b) and the alcohols (c) supplement one another to up to 100% by mass, and derivatives of this alcohol mixture.

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Branched alcohols and alcohol mixtures, their derivatives and use obtained from FT-feed stocks

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 from kerosene. Here, the paraffin stream 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 stream 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 fatty alcohols have structural isomers. The average branching degree is approx. 50%, the same as for the conventional oxo-alcohols, but the branching does not only occur 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%                                ~80%                                     ~95%

   R,R´...