Trichloroethylene → Biisocrotyl

HRID 66085

Reaction equation

HRID 66085 reaction equation
ClC=C(Cl)Cl.[CH3:6][C:7]([CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12])=[CH2:8].[Cl:14][C:15]([Cl:21])=[CH:16][CH2:17][C:18]([CH3:20])=[CH2:19]>>[CH3:6][C:7](=[CH:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH3:8].[Cl:14][C:15]([Cl:21])=[CH:16][CH:17]=[C:18]([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6575TrichloroethyleneHCID 123222,5-Dimethyl-1,5-hexadieneHCID 5561831,1-Dichloro-4-methyl-1,4-pentadiene

Product 2

HCID 12992BiisocrotylHCID 1087461,3-Pentadiene, 1,1-dichloro-4-methyl-

Procedure

A portion of the effluent from Example 6 was taken, containing 800 m mole trichloroethylene, 35 m mole 2,5-dimethylhexa-1,5-diene and 91 m mole 1,1-dichloro-4-methylpenta-1,4-diene. This mixture was subjected to fractional distillation, and about 600 m mole of trichloroethylene were removed slowly at ≯ 87° C. The residue was treated with p-toluene sulphonic acid (1% by weight) in an autoclave at 150° for 4 hours under autogeneous pressure. Essentially complete isomerisation of the dienes to their conjugated isomers was effected by this treatment. The mixture was fractionally distilled to yield 2,5-dimethylhexa-2,4-diene (28 m mole) and 1,1-dichloro-4-methylpenta-1,3-diene (80 m mole).

Workup

  1. distillationThis mixture was subjected to fractional distillation, and about 600 m mole of trichloroethylene
  2. customwere removed slowly at ≯ 87° C
  3. additionThe residue was treated with p-toluene sulphonic acid (1% by weight) in an autoclave at 150° for 4 hours under autogeneous pressure
  4. distillationThe mixture was fractionally distilled

Sources & evidence

ORD record
ord-22d8fa3d9f054464a658d6ff98f4a0b2
Source dataset
uspto-grants-1978_12
Patent number
US04130598

Linked notes

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