Carbon Dioxide → Sebacic Acid

HRID 1109609Notes

Reaction equation

HRID 1109609 reaction equation
[C:1](=[O:3])=[O:2].O[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=CC=2)(C)C)=CC=1.C(C1C=CC([OH:36])=CC=1)(C1C=CC=CC=1)(C)C.[Na][Na].C(Cl)(Cl)=O>C(Cl)Cl.C(N(CC)CC)C>[C:17]([OH:20])(=[O:36])[CH2:18][CH2:19][CH2:14][CH2:11][CH2:8][CH2:9][CH2:10][CH2:5][C:1]([OH:3])=[O:2]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 6371Phosgene3×HCID 6623Bisphenol AHCID 117424-CumylphenolHCID 141233Disodium

Product 1

HCID 5192Sebacic Acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A 2000 mL five neck Morton flask equipped with a bottom outlet was fitted with a mechanical stirrer, a pH probe, an aqueous sodium hydroxyde (50%) inlet tube, a Claisen adapter to which dry ice condenser was attached, and a gas inlet tube. The flask was charged with bisphenol A (71 g, 311 retool), triethylamine (0.9 mL), p-cumylphenol (2.0 g, 9 retool), methylene chloride (220 mL), and the disodium salt solution of DDDA described above. Then phosgene was introduced at a rate of 2 g/rain, while the pH was maintained at 8 by addition of caustic for 10 minutes; the pH was then raised and maintained at around 10.5 while phosgene addition continued for 10 additional minutes. The total amount of phosgene added was 40 g (400 mmol). The pH was adjusted to 11-11.5 and the organic phase was separated from the brine layer and washed with 2% hydrochloric acid (3×300 mL), and with deionized water (5×300 mL).

Workup

  1. customwas fitted with a mechanical stirrer
  2. temperaturewas maintained at 8 by addition of caustic for 10 minutes
  3. temperaturethe pH was then raised
  4. customthe organic phase was separated from the brine layer
  5. washwashed with 2% hydrochloric acid (3×300 mL)

Sources & evidence

ORD record
ord-e02405207701437aaa98001bab7212be
Source dataset
uspto-grants-1994_06
Patent number
US05321114

Reaction notes

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