Itaconic acid → Lactic acid itaconic acid epsilon-caprolactone

HRID 1044468Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C@H:2]([CH3:4])[OH:3].[C:7]([OH:15])(=[O:14])[C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH2:9].[C:16]1(=[O:23])[O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.OCC(CO)(CO)CO.[Sn+2]>>[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:7]([OH:15])(=[O:14])[C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH2:9].[C:16]1(=[O:23])[O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Reactant 5

HCID 811Itaconic acid

HCID 8285Pentaerythritol

HCID 10401epsilon-CAPROLACTONE

HCID 104883Stannous cation

HCID 107689L-Lactic Acid

Product 1

HCID 86597550Lactic acid itaconic acid epsilon-caprolactone

Procedure

The polymerisation was performed like in Example 1, but the amounts of the ingredients were 794.7 g of aqueous L-lactic acid (81 mole-%), 72.5 g of itaconic acid (7 mole-%), 110.7 g of ε-caprolactone (10 mole-%), 22.0 g of pentaerythritol (2 mole-%) and 0.39 g of tin(II) octoate, and the polymerisation time was 26 hours.

Sources & evidence

ORD record: ord-c841103ab0fc40968928bd54a36c5fc9
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563664B2

Reaction notes

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