Itaconic acid → Lactic acid itaconic acid

HRID 1044466Notes

Reaction equation

HRID 1044466 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].OCC(CO)(CO)CO.[Sn+2]>O>[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]

Participants

6

Reactant 4

HCID 811Itaconic acidHCID 8285PentaerythritolHCID 104883Stannous cationHCID 107689L-Lactic Acid

Product 1

HCID 86597549Lactic acid itaconic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

Into a 2 liter Rotavapor equipment, used as the reactor, 437.5 g of L-lactic acid was added (88% water solution corresponding to 89 mole-%), 47.9 g of itaconic acid (9 mole-%), 14.5 g of pentaerythritol (2 mole-%) and 0.19 g of tin(II) octoate. Dry nitrogen was led into the reactor and a 500 mbar absolute pressure was established. The reactor vessel was partly immersed in an oil bath with a temperature of 90° C. The temperature of the oil bath was increased at a rate of 30° C./h to 120° C., and the reaction mixture was mixed by starting the rotation at a speed of 100 rpm. The temperature of the oil bath was evenly increased by 15° C./h until 180° C., where it was kept until the end of the polymerisation. The pressure was decreased every hour by the following steps: 500 (start)—500-450-400-350-290-190-140-90-60-50-40-30 mbar, at which pressure it was kept to the end of the polymerisation. Bubbling of nitrogen was continued throughout the polymerisation and the formed water was collected as it evolved. Total polymerisation time was 24 hours.

Workup

  1. customThe reactor vessel was partly immersed in an oil bath with a temperature of 90° C
  2. temperatureThe temperature of the oil bath was increased at a rate of 30° C./h to 120° C.
  3. additionthe reaction mixture was mixed
  4. customwhere it was kept until the end of the polymerisation
  5. waitThe pressure was decreased every hour by the following steps
  6. custom500 (start)—500-450-400-350-290-190-140-90-60-50-40-30 mbar, at which pressure it was kept to the end of the polymerisation
  7. customBubbling of nitrogen
  8. customwas continued throughout the polymerisation
  9. customthe formed water was collected as it
  10. customTotal polymerisation time

Sources & evidence

ORD record
ord-18c60520748747cdb4b8e368fa21c1d6
Source dataset
uspto-grants-2013_10
Patent number
US08563664B2

Reaction notes

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