Method for production of 4-cyano benzoic acid or salts thereof
AssigneeBASF SE
InventorsDiego Ghislieri, Christian Willrodt, Christopher Koradin, Stefan Seemayer, Doreen Schachtschabel, Kai-Uwe Baldenius, Roland Goetz
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Abstract
Described herein are methods for the production of 4-cyano benzoic acid or salts thereof from terephthalonitrile using nitrilase as catalyst. Also described herein are compositions including 4-cyano benzoic acid.
Claims35
An isolated nitrilase capable of catalysing a reaction from terephthalonitrile to ammonium 4-cyano benzoic acid in an aqueous medium comprising water, nitrilase and terephthalonitrile and/or ammonium 4-cyano benzoic acid, wherein the concentration of ammonium 4-cyano benzoic acid in the aqueous medium after incubation is at least 5% (w/w) and the concentration of terephthalonitrile is below 1.0% (w/w).
An isolated nitrilase sequence selected from the group consisting of
- a. An amino acid molecule of SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22, and
- b. An amino acid molecule having at least 55% identity to the amino acid molecule of SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof, and
- c. An amino acid molecule encoded by a nucleic acid molecule of SEQ ID NO:
- 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof, and
- d. An amino acid molecule encoded by a nucleic acid molecule having at least 70% identity to SEQ ID NO:
- 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof, and
- e. An amino acid molecule encoded by a nucleic acid molecule hybridizing under stringent conditions to a fragment of at least 250 bases complementary to SEQ ID NO:
- 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- wherein the amino acid molecule as defined in b., c., d. and e. catalyzes a reaction from terephthalonitrile to ammonium 4-cyano benzoic acid in an aqueous medium.
A process for producing 4-cyano benzoic acid or salt thereof comprising the steps of
- i. Providing an aqueous medium comprising water, one or more nitrilase and terephthalonitrile,
- ii. Incubating the aqueous medium and
- iii. Optionally isolating the 4-cyano benzoic acid or salt thereof from the reaction mixture,
- wherein the one or more nitrilase is capable of catalysing the reaction from terephthalonitrile to ammonium 4-cyano benzoic acid in an aqueous medium comprising water, nitrilase and terephthalonitrile and/or ammonium 4-cyano benzoic acid, wherein the concentration of ammonium 4-cyano benzoic acid in the aqueous medium after incubation is at least 5% (w/w) and the concentration of terephthalonitrile is below 1.0% (w/w).
A process for producing 4-cyano benzoic acid or salt thereof comprising the steps of
- i. Providing an aqueous medium comprising water, one or more nitrilase and terephthalonitrile,
- ii. Incubating the aqueous medium and
- iii. Optionally isolating the 4-cyano benzoic acid or salt thereof from the reaction mixture,
- wherein the one or more nitrilase is selected from the group consisting of
- a. an amino acid molecule of SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof,
- b. an amino acid molecule having at least 55% identity to the amino acid molecule of SEQ ID NO:
- SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof,
- c. an amino acid molecule encoded by a nucleic acid molecule of SEQ ID NO 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- d. an amino acid molecule encoded by a nucleic acid molecule having at least 70% identity to SEQ ID NO:
- 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof, and
- e. an amino acid molecule encoded by a nucleic acid molecule hybridizing under stringent conditions to a fragment of at least 250 bases complementary to SEQ ID NO 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- wherein the amino acid molecule as defined in ii., iii., iv. and v. has an activity of converting terephthalonitrile to ammonium 4-cyano benzoic acid in an aqueous medium.
A recombinant construct comprising a nitrilase wherein the nitrilase is selected from the group consisting of
- a. an amino acid molecule of SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof,
- b. an amino acid molecule having at least 55% identity to the amino acid molecule of SEQ ID NO:
- SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof,
- c. an amino acid molecule encoded by a nucleic acid molecule of SEQ ID NO 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- d. an amino acid molecule encoded by a nucleic acid molecule having at least 70% identity to SEQ ID NO:
- 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof, and
- e. an amino acid molecule encoded by a nucleic acid molecule hybridizing under stringent conditions to a fragment of at least 250 bases complementary to SEQ ID NO 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- wherein the amino acid molecule as defined in ii., iii., iv. and v. catalyzes a reaction from terephthalonitrile to 4-cyano benzoic acid in an aqueous medium.
A composition comprising water, a nitrilase, terephthalonitrile and/or 4-cyano benzoic acid wherein the nitrilase is selected from the group consisting of
- a. an amino acid molecule of SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof,
- b. an amino acid molecule having at least 55% identity to the amino acid molecule of SEQ ID NO:
- SEQ ID NO:
- 2, 4, 6, 8, 10, 12, 14, 16, 20 or 22 or a functional fragment thereof,
- c. an amino acid molecule encoded by a nucleic acid molecule of SEQ ID NO 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- d. an amino acid molecule encoded by a nucleic acid molecule having at least 70% identity to SEQ ID NO:
- 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof, and
- e. an amino acid molecule encoded by a nucleic acid molecule hybridizing under stringent conditions to a fragment of at least 250 bases complementary to SEQ ID NO 1, 3, 5, 7, 9, 11, 13, 15, 19 or 21 or a functional fragment thereof,
- wherein the amino acid molecule as defined in ii., iii., iv. and v. catalyzes a reaction from terephthalonitrile to ammonium 4-cyano benzoic acid in an aqueous medium.
A composition consisting of
- a) 95 wt % to 99.5 wt % 4-cyano benzoic acid,
- b) 0.0 wt % to 0.5 wt % terephthalic acid,
- c) 0.2 wt % to 1.5 wt % chloride,
- d) 0.05 wt % to 0.2 wt % water, and
- e) and optionally up to 4.75 wt % other components.
A composition consisting of
- a) 95 wt % to 97 wt % 4-cyano benzoic acid,
- b) 0.0 wt % to 0.5 wt % terephthalic acid,
- c) 0.3 wt % to 1.5 wt % ammonium,
- d) 2.0 wt % to 0.4 wt % sulfate,
- e) 0.4 wt % to 1.0 wt % natrium, and
- f) and optionally up to 2.3 wt % other components.
A method for making an aqueous solution containing at least 5% (w/w) ammonium 4-cyano benzoic acid, below 1.0% (w/w) terephthalonitrile, and below 0.5% (w/w) terephthalic acid, comprising the steps of
- I. Providing an aqueous medium comprising water, one or more nitrilase and terephthalonitrile and
- II. Incubating the aqueous medium,
- wherein the nitrilase is capable of catalysing a reaction from terephthalonitrile to 4-cyano benzoic acid in an aqueous medium.
Dependencies are inferred from the claim text.