61186-96-7Relevant articles and documents
Sustainable production of dimethyl adipate by non-heme iron(iii) catalysed oxidative cleavage of catechol
Jastrzebski, Robin,Van Den Berg, Emily J.,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.
, p. 2103 - 2109 (2015/04/14)
Adipic acid and its esters are important bulk chemicals whose principal use is in the production of the nylon-6,6 polymer. There is considerable interest in finding novel green routes from sustainable feedstocks towards these important intermediates. Herein, we describe the catalytic oxidative cleavage of catechol to muconic acids using a catalyst prepared in situ from iron(iii) nitrate, tris(2-pyridylmethyl)amine and ammonium acetate. An investigation of catalyst loading, temperature and oxygen pressure, allowed a turnover frequency of 120 h-1 to be obtained. The subsequent hydrogenation and transesterification of the obtained muconic acid products were shown to proceed well over commercially available supported catalysts. After vacuum distillation, dimethyl adipate could be isolated in 62% yield from catechol, thus demonstrating a green and sustainable route to this important bulk chemical.
Catalytic oxidative cleavage of catechol by a non-heme iron(iii) complex as a green route to dimethyl adipate
Jastrzebski, Robin,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.
supporting information, p. 6912 - 6914 (2013/07/26)
The catalyst system prepared in situ from iron(iii) salts, tris(2-pyridylmethyl)amine and a base readily catalyses the intradiol dioxygenation of pyrocatechol in methanol, to primarily afford the half-methyl ester of muconic acid. Dimethyl adipate is obtained by the subsequent, one-step catalytic hydrogenation/esterification, thus providing a green route to this important nylon precursor.
