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US 11,274,071 B2Granted
Synthesis of alkyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and derivatives by a non-continuous production process
AssigneeDsm IP Assets B.V.
InventorsMarcel Joray, René Tobias Stemmler
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Abstract
The present invention relates to the manufacturing of a process of alkyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and alkyl 2-acetyl-9,13-di-methyl-5-methylenetetradeca-8,12-dienoate as well as 6,10,14-trimethylpenta-deca-5,9,13-trien-2-one and 10,14-dimethyl-6-methylenepentadeca-9,13-dien-2-5 one and 6,10,14-trimethylpentadecan-2-one.
Claims8
A process for manufacturing a compound of formula (I):
- wherein the dotted line in formula (I) indicates a carbon-carbon double bond which is located at one of the two indicated positions, wherein
- the process comprises reacting at temperature of 77° C. to 87° C. a compound of formula (II) and a compound of formula (Ill):
- in a non-continuous process in the presence of either:
- i) a mixture of a rhodium complex and water-soluble phosphine salt of formula (IV-a) or (IV-b), or
- ii) a rhodium complex obtained from a reaction of a rhodium complex and water-soluble phosphine salt of formula (IV-a) or (IV-b):
- and in the presence of water and an organic solvent selected from the group consisting of C1-C5 alcohols, alkylethers of C1-C5 alcohols, C2-C6 alkane diols, monoalkylethers of C2-C6 alkane diols, dialkylethers of C2-C6 alkane diols, esters of C1-C6 carboxyl acids or diacids, lactones and lactames;
- wherein R1 is a C1-10-alkyl group, n is an integer of 1-4, and Mn+ is an organic or inorganic cation having a charge +n, and
- wherein
- the process achieves conversions and selectivities of the compound of formula (I) of higher than 90%.
6 more elements
Dependencies are inferred from the claim text.