1-Dodecanol → TMC caprolactone

HRID 414424

Reaction equation

HRID 414424 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11][O:10]1.C(O)CCCCCCCCCCC>>[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11][O:10]1

Participants

4

Reactant 3

HCID 81931-DodecanolHCID 10401epsilon-CAPROLACTONEHCID 123834Trimethylene carbonate

Product 1

HCID 11275958TMC caprolactone

Conditions

Temperature
135 °C

Procedure

ε-Caprolactone (8.0 g, 0.070 mole), trimethylene carbonate (2.0 g, 0.020 mole), lauryl alcohol (0.283 g, 1.52×10-3 mole) and stannous chloride dihydrate (2.02 mg, 8.91×10-6 mole) were combined in a flask. The flask was flushed with nitrogen, evacuated and sealed. The flask was heated at 135° C. for 24 hours. The resulting polymer had a composition, as measured by 1H NMR, of 86 wt. % ε-caprolactone and 14 wt. % trimethylene carbonate. The ηinh of the copolymer was 0.26 dl/g (0.5 g/dl in HFAS).

Workup

  1. customThe flask was flushed with nitrogen
  2. customevacuated
  3. customsealed

Sources & evidence

ORD record
ord-112643679c0044b6956bcc0853d65c18
Source dataset
uspto-grants-1988_12
Patent number
US04791929

Linked notes

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