Methanol → 1-Hexene

HRID 1583384Notes

Reaction equation

HRID 1583384 reaction equation
CN(C)P(=O)(N(C)C)N(C)C.[Al](Cl)([CH2:15][CH3:16])CC.[CH3:18]O.[CH3:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[CH2:20]=[CH:21][CH2:22][CH2:23][CH2:15][CH3:16].[CH2:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:18][CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 7277Diethylaluminum chloride2×HCID 8003PentaneHCID 12679Hexamethylphosphoramide

Product 2

HCID 115971-HexeneHCID 194601,7-Octadiene

Conditions

Temperature
25 °C

Procedure

A solution of 54 grams (0.64 mole) 1-hexene and 7.9 grams (0.072 mole) 1,7-octadiene (molar charge ratio 90:10) in 80 ml pentane was polymerized with the required amount of Et2AlCl/hexamethylphosphoric triamide/δ-TiCl3 catalyst (2.4 millimoles δ-TiCl3). The molar ratio of hexamethylphosphoric triamide to Et2AlCl was 0.7:1 and of Et2AlCl to TiCl3 was 1.5:1. After agitating for 24 hours at 25° C., the resulting copolymer was isolated by methanol coagulation and dried. The conversion to copolymer was 83 percent, inherent viscosity 3.5 and percent gel=0. A copolymer prepared similarly but without hexamethylphosphoric triamide was obtained in 95 percent conversion. It had inherent viscosity of 1.1 and 78 percent gel. These data show the remarkable ability of the modified catalyst to suppress gel formation during polymerization while producing a higher molecular weight copolymer.

Workup

  1. customdried
  2. customA copolymer prepared similarly but without hexamethylphosphoric triamide
  3. customwas obtained in 95 percent conversion
  4. customduring polymerization
  5. customwhile producing a higher molecular weight copolymer

Sources & evidence

ORD record
ord-ce7e1036e93749f2ba1abf4f76a828ad
Source dataset
uspto-grants-1985_11
Patent number
US04551503

Reaction notes

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