Dimethyl terephthalate → HCID 118047294, compound

HRID 1499973Notes

Reaction equation

HRID 1499973 reaction equation
[C:1]([O:13]C)(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][OH:19]>>[OH:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:4][CH2:5][CH2:6][OH:8])[C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([C:1]([OH:13])=[O:12])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 8441Dimethyl terephthalateHCID 90863-Amino-1-propanol

Product 1

HCID 118047294HCID 118047294, compoundYield 171.6%

Procedure

Into a 500 mL separable flask, 48.1 g of dimethyl terephthalate (manufactured by Wako Pure Chemical Industries, Ltd.) and 112 g of 3-amino-1-propanol (manufactured by Wako Pure Chemical Industries, Ltd.) were placed and subjected to heat drying at 135° C. for 6.5 hours under nitrogen gas stream. To the reaction mixture, isopropyl alcohol was slowly added to thereby provide 59.8 g of N,N-bis(3-hydroxypropyl)terephthalic acid amide, which is an amide group-containing diol. Under a nitrogen gas atmosphere, into a reactor equipped with a mixer, 8.72 g of N,N-bis(3-hydroxypropyl)terephthalic acid amide, 29.8 g of polyethylene glycol (trade name: PEG2000U, manufactured by NOF CORPORATION), and 50 g of dehydrated dimethylacetamide (organic solvent, manufactured by Wako Pure Chemical Industries, Ltd.) were placed and heated at 100° C. under stirring to thereby provide a uniform solution. To this solution, a solution prepared by dissolving 11.5 g of 4,4-diphenylmethane diisocyanate (manufactured by Wako Pure Chemical Industries, Ltd.) in 10 g of dehydrated dimethylacetamide was gradually dropped. After the dropping was completed, the solution was heated for an hour under stirring. The reaction solution was cooled to 80° C. and subsequently reprecipitation was caused with 620 g of acetonitrile. The solid precipitate was isolated by filtration and then washed twice with 160 g of acetonitrile. Thus, a polymer was obtained.

Workup

  1. temperatureto heat
  2. customdrying at 135° C. for 6.5 hours under nitrogen gas stream
  3. additionTo the reaction mixture, isopropyl alcohol was slowly added

Sources & evidence

ORD record
ord-06a76ad6da8e40e5b7e77724d0ece2a5
Source dataset
uspto-grants-2015_12
Patent number
US09203048B2

Reaction notes

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