Methanol → 1-Hexene

HRID 1583385Notes

Reaction equation

HRID 1583385 reaction equation
[Al](Cl)([CH2:4][CH3:5])[CH2:2]C.C(OP(O[CH2:16][CH3:17])(OCC)=O)C.CO.CN(C)P(=O)(N(C)C)N(C)C.[CH3:31][CH2:32][CH2:33][CH2:34][CH3:35]>>[CH2:31]=[CH:32][CH2:33][CH2:34][CH2:4][CH3:5].[CH2:31]=[CH:32][CH2:33][CH2:34][CH2:35][CH2:2][CH:16]=[CH2:17]

Participants

7

Reactant 5

HCID 887MethanolHCID 6535Triethyl Phosphate2×HCID 7277Diethylaluminum chloride2×HCID 8003PentaneHCID 12679Hexamethylphosphoramide

Product 2

HCID 115971-HexeneHCID 194601,7-Octadiene

Procedure

A solution of 54 grams (0.64 mole) 1-hexene and 3.8 grams (0.034 mole) 1,7-octadiene (molar charge ratio 95:5) in 80 ml pentane was polymerized with Et2AlCl/triethylphosphate/δ-TiCl3 catalyst (1.0 millimole δ-TiCl3). The molar ratio of Et2AlCl to δ-TiCl3 was 1.5:1 and of triethylphosphate to Et2AlCl was 0.7:1. After agitation for 24 hours at 25° C., the resulting copolymer was isolated by methanol coagulation and dried. The conversion to copolymer was 74 percent, with an inherent viscosity of 5.1 and zero percent gel. A copolymer prepared similarly but without triethylphosphate was obtained in 84 percent conversion. It had an inherent viscosity of 4.8 and 20 percent gel. These data show that triethylphosphate, like hexamethylphosphoric triamide, suppresses gel formation during polymerization.

Workup

  1. customdried
  2. customA copolymer prepared similarly but without triethylphosphate
  3. customwas obtained in 84 percent conversion
  4. customduring polymerization

Sources & evidence

ORD record
ord-8d3e2a4dab534f46911c4d0a3e635506
Source dataset
uspto-grants-1985_11
Patent number
US04551503

Reaction notes

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