Mb. Polk et al., Nylon 66, nylon 46, and PET phase-transfer-catalyzed alkaline depolymerization at atmospheric pressure, POLYM-PLAST, 38(3), 1999, pp. 459-470
The depolymerization of PET, nylon 66, and nylon 46 at high temperatures in
an autoclave is well known in the patent literature. We sought to invent p
rocesses for the depolymerization of PET, nylon 66, and nylon 46 in alkalin
e solutions at low temperatures and atmospheric pressure. A method was deve
loped for the depolymerization of polyethylene terephthalate (PET) which in
volved the use of quarternary ammonium salt phase-transfer catalysts in sap
onification processes at atmospheric pressure and temperatures as low as ro
om temperature. Phenyltrimethylammonium chloride, hexadecyltrimethylammoniu
m bromide, trioctylmethylammonium chloride, and trioctylmethylammonium brom
ide were found to be effective catalysts for the depolymerization of PET in
5% aqueous sodium hydroxide solutions at temperatures as high as 80 degree
s C and atmospheric pressure to form terephthalic acid in yields as high as
93%. The catalyst could be recycled. The alkaline phase-transfer-catalysis
approach was then successfully applied for the depolymerizations of nylon
66 and nylon 46. Benzyltrimethylammonium bromide was discovered to be an ef
fective phase-transfer catalyst in 50 wt.% sodium hydroxide solution for th
e conversion of nylon 46 to oligomers. The collected nylon 46 oligomers wer
e repolymerized using solid-state polymerization techniques to form high-mo
lecular-weight nylon 46. Nylon 66 fibers were depolymerized in the presence
of benzyltrimethylammonium bromide in 50% sodium hydroxide to form oligome
rs and a monomer. Adipic acid was isolated.