Isoprene → HCID 86591155, compound

HRID 1831021Notes

Reaction equation

HRID 1831021 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[CH3:6][C:7](=[CH2:9])[CH3:8].C=CC=C.[Al+3].[Cl-].[Cl-].[Cl-]>O.CO.CCCCCCC>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:1]=[CH:2][C:3](=[CH2:4])[CH3:5].[CH3:8][C:7](=[CH2:6])[CH3:9]

Participants

8

Reactant 4

HCID 6557Isoprene2×HCID 78451,3-Butadiene2×HCID 8255Isobutylene2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 86591155HCID 86591155, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8900HeptaneSolvent

Conditions

Temperature
6.300000190734863 °C

Procedure

A reactor is charged with 6.34 parts isoprene, 255.8 parts isobutylene, 164.2 parts butadiene and 1000 parts by volume heptane. The mixture is allowed to reflux, 6.3° C. Over 2 hours, 2.9 parts AlCl3, 30.6 parts isoprene, 1188.4 parts isobutylene and 24.3 parts butadiene are added to the reactor maintaining the reflux at 6.3° C. The reaction mixture is drained into 100 parts methanol. After the bulk of the unreacted monomers has boiled off (overnight), 150 parts water are added to the crude reaction product. The mixture is stirred and then shaken in a separatory funnel. The aqueous layer is removed then the organic layer is washed twice more with 150 parts water and finally with 100 parts saturated aqueous NaCl solution. The organic phase is dried with MgSO4 and pressure filtered. Solvents are removed on a rotary evaporator. The yield of product is 1185.6 parts. The product has GPC {overscore (M)}n=3504 and {overscore (M)}w=14956. By 1H NMR the product contains 2.14% butadiene and 1.01% isoprene.

Workup

  1. temperaturemaintaining the
  2. temperaturereflux at 6.3° C
  3. additionare added to the crude
  4. customreaction product
  5. stirringshaken in a separatory funnel
  6. customThe aqueous layer is removed
  7. washthe organic layer is washed twice more with 150 parts water and finally with 100 parts saturated aqueous NaCl solution
  8. dry with materialThe organic phase is dried with MgSO4 and pressure
  9. filtrationfiltered
  10. customSolvents are removed on a rotary evaporator

Sources & evidence

ORD record
ord-8cb971ddb1584b4391b57f37adec4d27
Source dataset
uspto-grants-2006_06
Patent number
US07067594B2

Reaction notes

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