Isoprene → Squalene

HRID 2051440Notes

Reaction equation

HRID 2051440 reaction equation
C=CC(=C)C.[CH3:6][CH:7]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][CH2:16][CH:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH3:29])[CH3:24])[CH3:18])[CH3:13])[CH3:8]>C([Li])(CC)C.C1C=C2C(C=C(C([O-])=O)C=C2)=CC=1.C1C=C2C(C=C(C([O-])=O)C=C2)=CC=1.[Ni+2].[Ni].C1CCCCC1>[CH3:35][C:33](=[CH:32][CH2:31][CH2:30]/[C:28](=[CH:27]/[CH2:26][CH2:25]/[C:23](=[CH:22]/[CH2:21][CH2:20]/[CH:19]=[C:17](/[CH2:16][CH2:15]/[CH:14]=[C:12](/[CH2:11][CH2:10][CH:9]=[C:7]([CH3:8])[CH3:6])\[CH3:13])\[CH3:18])/[CH3:24])/[CH3:29])[CH3:34]

Participants

7

Reactant 2

HCID 6557IsopreneHCID 8089Squalane

Product 1

HCID 638072Squalene

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 14647680Nickel naphthenateCatalystHCID 178418400CID 53628100CatalystHCID 8078CyclohexaneSolvent

Procedure

As the oligomer (D) represented by the formula: ##STR2## When m is 0 and R is ##STR3## is a hydrogenated product of polyisoprene. For obtaining a hydrogenated product of polyisoprene, it can be easily produced by carrying out anion polymerization of isoprene in a cyclohexane solution under the copresence of sec-butyl lithium catalyst and then hydrogenating the polymer in the presence of a nickel naphthenate catalyst. On the other hand, when m is 1, n and pare 2, and R is ##STR4## it is squalane obtained by hydrogenation of squalene with a nickel catalyst. Squalene which is a starting material of squalane is contained in liver oil of a deep sea shark, and it can be obtained by subjecting the unsaponified product of shark liver oil to fractional distillation, deacidification and further to fractional distillation in the presence of metallic sodium, or condensing farnesyl chloride or farnesyl bromide in the presence of metallic magnesium, or carrying out Wittig reaction on transgeraniol acetone.

Workup

  1. customcan be easily produced

Sources & evidence

ORD record
ord-0ae9cfcf42f54576a5cd4a03a0b92817
Source dataset
uspto-grants-1991_05
Patent number
US05018828

Reaction notes

Loading…