epsilon-CAPROLACTONE → L-lactide epsilon-caprolactone

HRID 1438867Notes

Reaction equation

HRID 1438867 reaction equation
[CH3:1][C@@H:2]1[O:9][C:7](=[O:8])[C@H:6]([CH3:10])[O:5][C:3]1=[O:4].[C:11]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1C=CC=CC=1>[CH3:1][C@@H:2]1[O:9][C:7](=[O:8])[C@H:6]([CH3:10])[O:5][C:3]1=[O:4].[C:11]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10401epsilon-CAPROLACTONEHCID 107983Lactide, L-

Product 1

HCID 131710947L-lactide epsilon-caprolactone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The procedure of Example II is repeated except that 461 grams of L-(-)-lactide, 5.4 ml of benzene containing 1.1 gram of pure stannous caprylate and 81.3 grams of epsilon caprolactone are placed in the ampoule, evacuated, sealed and heated for 15.5 hours at 136° to 140° C. The copolymer has an outstanding combination of physical properties. The copolymer is a tough, strong, clear material. It has good impact resistance and a good combination of tensile strength and elongation properties. The copolymer has GPC molecular weights of Mw = 192,200 and Mn = 44,900. The residual lactide comprises 1.15 percent. Differential thermal analysis (DTA) of the copolymer reveals a moderate amount of crystallinity with a melting point endotherm at 133° C. Molded sheets of the copolymer are clear, colorless, supple and tough. Physical properties are listed in more detail in Table 1.

Workup

  1. customevacuated
  2. customsealed
  3. temperatureheated for 15.5 hours at 136° to 140° C
  4. customat 133° C

Sources & evidence

ORD record
ord-bfbd781829ba474ba06bcd96b37ad392
Source dataset
uspto-grants-1977_11
Patent number
US04057537

Reaction notes

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