Production of nylon 6,6 salt
AssigneeCelgene Corporation
InventorsSol J. Barer, Peter C. Maxwell, Jih-Han Hsieh
Life of this patent
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Abstract
This invention provides a process for producing nylon 6,6 salt which involves bioconversion of toluene to muconic acid in the presence of hexamethylenediamine to yield hexamethylenediamine muconate salt. Hydrogenation of this salt provides an aqueous solution of the desired hexamethylenediamine adipate salt.
Claims13
A process for the production of hexamethylenediamine muconate salt which comprises ( 1) feeding toluene to an aqueous fermentation medium containing hexamethylenediamine and a microorganism strain which metabolizes the toluene to muconic acid and has the following characteristics:
- (a) possesses catechol 1,2-oxygenase enzyme with activity that is not inhibited in the presence of a low level of muconic acid in a growth medium;
- (b) lacks active catechol 2,3-oxygenase enzyme;
- (c) lacks active muconate lactonizing enzyme;
- (d) cells are rod shaped, vigorously motile and polarly flagellated;
- and
- (e) cells grow well on p-hydroxybenzoate;
- and (2) separating the microorganism cells from the aqueous fermentation medium which contains hexamethylenediamine muconate salt product in solution.
A process for the production of hexamethylenediamine adipate salt which comprises (1) feeding toluene to an aqueous fermentation medium containing hexamethylenediamine and a microorganism strain which metabolizes the toluene to muconic acid and has the following characteristics:
- (a) possesses catechol 1,2-oxygenase enzyme with activity that is not inhibited in the presence of a low level of muconic acid in a growth medium;
- (b) lacks active catechol 2,3-oxygenase enzyme;
- (c) lacks active muconate lactonizing enzyme;
- (d) cells are rod shaped, vigorously motile and polarly flagellated;
- and
- (e) cells grow well on p-hydroxybenzoate;
- (2) separating the microorganism cells from the aqueous fermentation medium which contains hexamethylenediamine muconate salt in solution;
- and (3) subjecting the cell-free aqueous solution provided by step (2) to catalytic hydrogenation conditions to convert hexamethylenediamine muconate salt to hexamethylenediamine adipate salt.
A process for the production of hexamethylenediamine and hexamethylenediamine muconate salt which comprises (1) feeding toluene to an aqueous fermentation medium containing hexamethylenediamine and a microorganism strain which metabolizes the toluene to muconic acid and has the following characteristics:
- (a) possesses catechol 1,2-oxygenase enzyme with activity that is not inhibited in the presence of a low level of muconic acid in a growth medium;
- (b) lacks active catechol 2,3-oxygenase enzyme;
- (c) lacks active muconate lactonizing enzyme;
- (d) cells are rod shaped, vigorously motile and polarly flatellated;
- and
- (e) cells grow well on p-hydroxybenzoate;
- (2) separating the microorganism cells from the aqueous fermentation medium which contains hexamethylenediamine muconate salt in solution;
- (3) recovering the hexamethylenediamine muconate salt from a portion of the cell-free aqueous solution provided by step (2);
- (4) treating the recovered hexamethylenediamine muconate salt from step (3) with ammonia under amide-dehydration conditions to form muconitrile;
- and (5) subjecting the muconitrile to catalytic hydrogenation conditions to convert the mucononitrile to hexamethylenediamine.
Dependencies are inferred from the claim text.