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

Temperature

87.5 °C

1 equivalent of 6-aminohexanoic acid (ACA), 1 equivalent of sodium hydroxide (NaOH), and suitable amount of water serving as solvent were added into a reaction bottle. After reacting for 2 hours, the reaction bottle was heated to remove the water, and then a solid mixture was obtained. Next, the solid mixture was dried at 90° C. for 12 hours in oven, and then solid 6-aminohexanoic acid sodium salt (ACA-Na) was obtained. Next, 0.97 g (0.005 mole) of dimethyl terephthalate (DMT), 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 5 times these washing and filtration steps. Next, the washed solid was dried in an oven at 80° C., N,N′-bis(carboxypentyl)terephthalamide (BCTM) was obtained after drying. The above-mentioned reaction is represented as:

1. temperaturecooled to room temperature
2. dissolutionAfter the solid reactant was dissolved
3. customcollected to a glass bottle
4. washThen, the solid precipitate was washed with 3 times weight of distilled water
5. filtrationfiltered
6. filtrationfiltration steps
7. customNext, the washed solid was dried in an oven at 80° C.

ORD record

ord-a82d963fd68346549cc95ae37089d78f

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422398B2