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Long Chain Branched Fatty Alcohols from Hydroformylation, their Mixtures, Derivatives and Use

IP.com Disclosure Number: IPCOM000246567D
Publication Date: 2016-Jun-17

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The IP.com Prior Art Database

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Clemens Schroeder: AUTHOR

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 chain length range C6 to C20 can be obtained by the Ziegler process from aluminium, hydrogen, and ethylene. In addition, -olefins can be obtained by ethylene polymerisation and converted into saturated linear primary alcohols or acids, with chain lengths in the range C20 to C60 (Unilin alcohols and acids).

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Long Chain Branched Fatty Alcohols from Hydroformylation, their Mixtures, Derivatives and Use

1.    Definition of Branched Alcohols and Mixtures Thereof

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 chain length range C6 to C20 can be obtained by the Ziegler process from aluminium, hydrogen, and ethylene. In addition, a-olefins can be obtained by ethylene polymerisation and converted into saturated linear primary alcohols or acids, with chain lengths in the range C20 to C60 (Unilinä alcohols and acids).

Multiple branched fatty alcohols are also known.  Such fatty alcohols are obtained by oligomerisation of propene and/or butene.  Normal chain lengths for such alcohols are C6 to C15 (e.g. isononanol, isodecanol and isotridecanol).

Semi-linear fatty alcohols such as NEODOL alcohols (in the C9 to C17 carbon range) can be synthesized by ethylene oligomerisation, followed by selective hydroformylation of the obtained α-olefins.  Such alcohols have a content of primary, linear, and saturated alcohols of approx. 80%.

The conventional oxo-alcohols (O-alcohols), LIAL , are generally produced by unmodified Cobalt catalysed hydroformylation of linear olefins C10-C17.  Olefin production is based on dehydrogenation of linear paraffins. Alternatively, olefins can be obtained from a Fischer Tropsch production process.  Linear paraffins production is based on extraction, by molecular sieves, from kerosene.  The C11-C18 fatty alcohols obtained by this process are semi-linear alcohols with a content of primary, linear and saturated fatty alcohols between 30% and 60%. It is known that this product can be split into linear and branched portions by partial crystallisation or distillation to yield branched alcohols or alcohol mixtures with less than 10% linear alcohols.

An alternative synthetic pathway to such branched alcohols is the unmodified Rhodium catalysed

hydroformylation of linear olefins C10-C17, resulting in lower primary, linear saturated alcohol content compared to the Cobalt process.  The unmodified Rh-hydroformylation process is therefore able to produce branched alcohols or alcohol mixtures with ≤10% linear primary alcohol content, without the process of partial crystallisation or distillation (as is necessary for the Cobalt process).

The C11 -C18 fatty alcohols or alcohol mixtures, obtained by either of the unmodified Co- or Rh-catalysed hydroformylation processes, comprise :

(a) equal to or less than 10 % by mass linear, aliphatic, preferably saturated alcohols or alcohol mixtures   with carbon chain lengths varying from C 11 to C18;

(b)  80 to 100% by mass of the alcohol with an aliphat...