Adipic Acid → 1,2,3-Propanetricarboxylic acid

HRID 1627404

Reaction equation

HRID 1627404 reaction equation
[C:1]([OH:10])(=O)[CH2:2][CH2:3]CC[C:6]([OH:8])=[O:7].[C:11]([OH:22])(=[O:21])[CH2:12][CH:13]([CH2:17][C:18]([OH:20])=[O:19])[C:14]([OH:16])=[O:15].C(C(O)=O)C(C(O)=O)C(C(O)=O)CC(O)=O.C1C(C2OC2)CC2OC2C1>>[C:6](=[O:8])=[O:7].[CH2:1]1[O:10][CH:2]1[CH3:3].[C:11]([OH:22])(=[O:21])[CH2:12][CH:13]([CH2:17][C:18]([OH:20])=[O:19])[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 196Adipic AcidHCID 7833Vinyl cyclohexene dioxideHCID 149251,2,3-Propanetricarboxylic acidHCID 155601,2,3,4-Butanetetracarboxylic acid

Product 2

HCID 149251,2,3-Propanetricarboxylic acidHCID 18518868Carbon dioxide propylene oxide

Procedure

After fixing a chain transfer agent to control a molar fraction of —COOH group to 45 relative to a molar fraction of the catalyst and then introducing adipic acid, 5.9 mg (Entries 1 to 5); tricarballylic acid, 5.1 mg (Entries 6 to 10); 1,2,3,4-butane tetracarboxylic acid, 4.7 mg (Entries 11 to 15)) into a reactor, vinylcyclohexene dioxide was weighed to numeral values listed in TABLE 3, relative to the molar fraction of the catalyst and then introduced (into the reactor). Then, polymerization was executed and the catalyst was removed according to the same procedures as described in Example 1, resulting in pure copolymer. TABLE 3 summarizes results of the polymerization. FIG. 2 shows GPC curves of a copolymer obtained by carbon dioxide/propylene oxide copolymerization in the presence of tricarballylic acid (C3H5(CO2H)3) and diepoxide, wherein reference numeral in each curve denotes an entry number in TABLE 2.

Workup

  1. additionintroduced (into the reactor)
  2. customThen, polymerization
  3. customthe catalyst was removed
  4. customresulting in pure copolymer
  5. customTABLE 3 summarizes results of the polymerization

Sources & evidence

ORD record
ord-c860c5f6b7434b09ad189e9abf9ee4fd
Source dataset
uspto-grants-2014_07
Patent number
US08785592B2

Linked notes

Loading…