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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1486028Generated: October 30, 2026

Ethylene Glycol → 6-[[4-(5-carboxypentylcarbamoyl)benzoyl]amino]hexanoic Acid

https://huagongshe.com/reaction/1486028

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthylene GlycolHCID 174—
ReactantWaterHCID 962—
ReactantSulfuric AcidHCID 1118—
ReactantBis(2-hydroxyethyl) terephthalateHCID 13739—
Reactanthexanoic acid, 6-amino-, monosodium saltHCID 23663648—
Product6-[[4-(5-carboxypentylcarbamoyl)benzoyl]amino]hexanoic AcidHCID 5159834—

Reaction Conditions

Temperature87.5 °C

Reaction Steps

3.84 g (0.005 mole) of bis-hydroxylethyl terephthalate (BHET), 2.32 g (0.015 mole) of dried 6-aminohexanoic acid sodium salt, and 20 ml of ethylene glycol (EG) were put into a reaction bottle. The reaction bottle was heated at 85-90° C. for 14 hours in the presence of nitrogen gas, and then cooled to room temperature and 20 ml of distilled water was added into it. After the solid reactant was dissolved, sulfuric acid aqueous solution (0.1M) was added dropwise slowly into the reaction bottle until the pH value of the solution was 6. Next, after the reaction bottle was set aside at room temperature for 20 hours, a solid precipitate was observed and collected to a glass bottle. Then, the solid precipitate was washed with 3 times weight of distilled water and filtered, and repeated 4 times these washing and filteration steps. Next, the washed solid was dried in an oven at 80° C., obtaining a N,N′-bis(carboxypentyl)terephthalamide (BCTM). The above-mentioned reaction is represented as:

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09422398B2
Source datasetuspto-grants-2016_08
ORD IDord-05760cd292b2415885dcf5e98f276ce7
Source noteuspto-grants-2016_08