Toluene → 1-Hexene

HRID 329307

Reaction equation

HRID 329307 reaction equation
Cl[C:2]1(Cl)[C:6](Cl)=[C:5](Cl)[C:4](Cl)=[C:3]1Cl.[C:12]1(C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:17]=[CH:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:13]=[CH:12][CH2:17][CH2:2][CH2:6][CH2:5][CH:4]=[CH2:3]

Participants

4

Reactant 2

HCID 1140TolueneHCID 6478Hexachlorocyclopentadiene

Product 2

HCID 115971-HexeneHCID 194601,7-Octadiene

Procedure

A copolymer of 1-hexene and 1,7-octadiene (molar charge ratio 90:10) was synthesized according to the general procedure in Example I. It had an inherent viscosity of 3.5 dl./g. and 25 percent gel. A solution of 43.3 grams of this copolymer and 95 grams of hexachlorocyclopentadiene in 750 ml. toluene containing finely dispersed gel was heated at 110° C. for 24 hours. After cooling, the reaction mixture was precipitated in excess methanol. The yield of the product was 51.5 grams, inherent viscosity 1.5 dl./g., gel 16 percent. An acetone-extracted sample contained 14.1 percent chlorine, indicating that about 70 percent of the double bonds in the original copolymer had reacted with hexachlorocyclopentadiene.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was precipitated in excess methanol
  3. extractionAn acetone-extracted sample
  4. customhad reacted with hexachlorocyclopentadiene

Sources & evidence

ORD record
ord-cb1782b96a9f4168b86deed4a2a3e2ea
Source dataset
uspto-grants-1977_04
Patent number
US04020250

Linked notes

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