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US 2007/0167655 A1Published application
Method for the production of tetrahydrogeranylacetone
AssigneeBASF SE
InventorsWalter Dobler, Nicolaus Bahr, Alois Kindler, Christian Miller, Axel Salden
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Abstract
The present invention relates to a process for preparing tetrahydrogeranylacetone (tetrahydropseudoionone) by aldol condensation of citral with acetone and subsequent hydrogenation. The invention further relates to the use of thus obtained tetrahydro-geranylacetone for preparing phytol, isophytol, tocopherol and/or tocopherol derivatives. In addition, the invention relates to processes for preparing tocopherols and/or tocopherol derivatives.
Claims25
A process for preparing tetrahydrogeranylacetone, comprising:
- I. an aldol condensation of citral with acetone in the presence of aqueous alkali comprising at least one alkali metal hydroxide to form a condensate comprising pseudoionone and
- II. a hydrogenation of the condensate.
A process for preparing tocopherols and/or tocopherol derivatives, comprising
- a) an aldol condensation of citral with acetone in the presence of a basic substance to form a condensate comprising pseudoionone,
- b) a hydrogenation of the pseudoionone present in the condensate to give 6,10-dimethyl-2-undecanone,
- c) a reaction of thus obtained 6,10-dimethyl-2-undecanone with acetylene in the presence of a basic compound to give 3,7,11-trimethyl-1-dodecyn-3-ol,
- d) a reaction of thus obtained 3,7,11-trimethyl-1-dodecyn-3-ol with hydrogen in the presence of a catalyst comprising palladium, silver and/or bismuth and carbon monoxide to give 3,7,11-trimethyl-1-dodecen-3-ol,
- e) a reaction of thus obtained 3,7,11-trimethyl-1-dodecen-3-ol with diketene or ethyl acetoacetate to give the corresponding ester,
- f) a rearrangement of the thus obtained ester to give 6,10,14-trimethyl-5-pentadecen-2-one by Carroll reaction,
- g) a reaction of thus obtained 6,10,14-trimethyl-5-pentadecen-2-one with hydrogen to give 6,10,14-trimethylpentadecan-2-one,
- h) a reaction of thus obtained 6,10,14-trimethylpentadecan-2-one with acetylene in the presence of a base to give 3,7,11,15-tetramethyl-1-hexadecyn-3-ol,
- i) a reaction of thus obtained 3,7,11,15-tetramethyl-1-hexadecin-3-ol with hydrogen in the presence of a catalyst comprising palladium, silver and/or bismuth and carbon monoxide to give 3,7,11,15-tetramethyl-1-hexadecen-3-ol and
- j) a reaction of 3,7,11,15-tetramethyl-1-hexadecen-3-ol to give tocopherol and/or tocopherol derivatives and
- k) if appropriate, an acetylation of the thus obtained tocopherol.
8 more elements
Dependencies are inferred from the claim text.