epsilon-CAPROLACTONE → L-lactide epsilon-caprolactone

HRID 1438868Notes

Reaction equation

HRID 1438868 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

Conditions

Temperature
130 °C

Procedure

The procedure of Example II is repeated except that 500 grams of L-(-)-lactide, 55.5 grams of epsilon caprolactone and 5 ml of benzene containing 1 gram of stannous caprylate are placed in the ampoule, evacuated, sealed and heated for 18 hours at 130° C. and then 45 minutes at 160° C. The copolymer has GPC molecular weights of Mw = 223,000 and Mn = 35,700. The residual lactide comprises about 1.65 percent. Compression molded specimens are strong and transparent with a DTA melting point of 151° C. when fast cooled. Slow-cooled moldings are opaque and show an increased DTA crystallinity. The molded specimens have GPC molecular weights of Mw = 116,200 and Mn = 22,000. The residual monomer comprises about 1.8 percent. Physical properties are listed in more detail in Table 1.

Workup

  1. customevacuated
  2. customsealed
  3. custom45 minutes
  4. customat 160° C
  5. temperaturefast cooled

Sources & evidence

ORD record
ord-96625f2034a246b7b0e20e68188d5382
Source dataset
uspto-grants-1977_11
Patent number
US04057537

Reaction notes

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