Ethylene → 1-Decene

HRID 526659

Reaction equation

HRID 526659 reaction equation
C=C.[C:3]([OH:20])(=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\CCCCCC.[C:21](O)(=O)[CH2:22]CCCCCC/C=C\CCCCCCCC.[C:41](OC)(=O)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]=[CH2:50].C=CCCCCCC>>[C:3]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[CH2:41]=[CH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

7

Reactant 5

HCID 6325EthyleneHCID 81251-OcteneHCID 445638Palmitoleic Acid2×HCID 445639Oleic AcidHCID 1778877Methyl 9-decenoate

Product 2

HCID 133811-DeceneHCID 522255Ethyl 9-decenoate

Procedure

Ethenolysis comprises a cross-metathesis reaction involving ethene. According to some preferred embodiments of the invention, a mixture of ethyl esters of Palmitoleic acid (C16:1) and Oleic acid (C18:1) are subjected to conditions of ethenolysis to yield a mixture of α-olefins (1-Octene and 1-Decene) and Methyl 9-Decenoate. See FIG. 8. The 1-Octene is a product unique to ethenolysis of Palmitoleic acid (C16:1). In the inventive method, Ethyl 9-Decenoate and 1-Decene will also form from the mixture of Palmitoleic and Oleic acid ethyl esters. Prior art methods using Oleic acid esters (Methyl Oleate) as the starting material only produce Methyl 9-Decenoate and 1-Decene.

Workup

  1. customa cross-metathesis reaction
  2. customto yield

Sources & evidence

ORD record
ord-da14fc64f9344f40a488584c585d418d
Source dataset
uspto-grants-2016_05
Patent number
US09346729B2

Linked notes

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