Olefin metathesis for the commercial synthesis of civetone, muscone and exaltone from fatty acids
Olefin metathesis for the commercial synthesis of civetone, muscone and exaltone from fatty acids
A survey of syntheses of civetone is presented. A cost effective synthesis for the commercial manufacture of civetone via theolefin metathesis reaction followed by Dieckmann cyclisation has been successfully carried out and presented with the economics of the projected scale-up process. A new economical general route to w-alkenoic acids by pyrolysis of the polyester (e.g. dec-?-enoic acid and non-8-anoic acid) has been developed. The metathesis reaction has been further applied to the synthesis of dimethyl 1,16-hexadec-8-enedioate which is cyclised by Dieckmann reaction to give cyclohexadec-8-en-l-one. This is the intermediate for the synthesis of muscone and exaltone. An improvement in the Dieckmann reaction has been made to obtain higher yields by the chemical removal with potassium metal of the alcohol produced in the reaction. A new commercially attractive metathesis catalytic system (Et 3A1/SnC14/WC16) for the metathesie of w-alkenoic esters has also been developed.
University of Southampton
Bandaranayake, Aruna Dias
1981
Bandaranayake, Aruna Dias
Bandaranayake, Aruna Dias
(1981)
Olefin metathesis for the commercial synthesis of civetone, muscone and exaltone from fatty acids.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A survey of syntheses of civetone is presented. A cost effective synthesis for the commercial manufacture of civetone via theolefin metathesis reaction followed by Dieckmann cyclisation has been successfully carried out and presented with the economics of the projected scale-up process. A new economical general route to w-alkenoic acids by pyrolysis of the polyester (e.g. dec-?-enoic acid and non-8-anoic acid) has been developed. The metathesis reaction has been further applied to the synthesis of dimethyl 1,16-hexadec-8-enedioate which is cyclised by Dieckmann reaction to give cyclohexadec-8-en-l-one. This is the intermediate for the synthesis of muscone and exaltone. An improvement in the Dieckmann reaction has been made to obtain higher yields by the chemical removal with potassium metal of the alcohol produced in the reaction. A new commercially attractive metathesis catalytic system (Et 3A1/SnC14/WC16) for the metathesie of w-alkenoic esters has also been developed.
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Published date: 1981
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Local EPrints ID: 459570
URI: http://eprints.soton.ac.uk/id/eprint/459570
PURE UUID: f3ec9e7f-e387-4d62-b33c-783c461492aa
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Date deposited: 04 Jul 2022 17:14
Last modified: 04 Jul 2022 17:14
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Author:
Aruna Dias Bandaranayake
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