Patent classifications
C07C255/09
Process for the preparation of pregabalin
The present invention provides an improved process for the preparation of a compound of formula (I), which comprises the steps of: formula (I), (a) reacting isovaleraldehyde of formula (II) and alkyl cyanoacetate of formula (III) optionally in presence of salts of weak acid and weak base or weak base in a suitable solvent to get 2-cyano-5-methyl-hex-2-enoic acid alkyl ester of formula (IV); (b) reacting 2-cyano-5-methyl-hex-2-enoic acid alkyl ester of formula (IV) with a suitable cyanide source in water or in an organic solvent or mixture thereof to get 2-isobutylsuccinonitrile of formula (V); (c) obtaining optionally 2-isobutylsuccinonitrile of formula (V) by reacting isovaleraldehyde of formula (II) and alkyl cyanoacetate of formula (III) in presence of suitable cyanide source in water or in an organic solvent or mixture thereof in single step; (d) converting 2-isobutylsuccinonitrile of formula (V) to racemic 3-cyano-5-methyl-hexanoic acid or salt thereof of formula (VI) with a genetically modified nitrilase enzyme (Nit 9N_56_2) in water or optionally with an organic co-solvent at appropriate pH and temperature; (e) converting racemic 3-cyano-5-methyl-hexanoic acid or salt thereof of formula (VI) to racemic alkyl 3-cyano-5-methyl-hexanoate of formula (VII) by treatment with alcohol (R3OH) and acidic catalyst or alkyl halide (R3X) in presence of a base in a suitable solvent or a mixture of solvents thereof; (f) obtaining (S)-alkyl 3-cyano-5-methyl-hexanoate of formula (VIII) and (R)-3-cyano-5-methyl-hexanoic acid or salt thereof of formula (X) by enzymatic enantioselective hydrolysis in water or organic solvent or a mixture thereof from racemic alkyl 3-cyano-5-methyl-hexanoate of formula (VII); (g) obtaining optionally the compound of formula (VII) by racemizing unwanted (R)-3-cyano-5-methyl-hexanoic acid or salt thereof of formula (X) or substantially enriched (R)-3-cyano-5-methyl-hexanoic acid salt thereof of formula (X) in presence of a base in organic solvent or a mixture thereof; (h) converting (S)-alkyl 3-cyano-5-methyl-hexanoate of formula (VIII) to pregabalin of formula (I) by hydrolyzing ester group with suitable alkali or alkaline earth metal base followed by hydrogenation optionally in one pot in a solvent selected from water or other organic solvents or a mixture thereof in presence of a suitable hydrogenation catalyst. ##STR00001##
NON-AQUEOUS ELECTROLYTE ADDITIVE, AND NON-AQUEOUS ELECTROLYTE FOR LITHIUM SECONDARY BATTERY COMPRISING THE SAME AND LITHIUM SECONDARY BATTERY
The present invention relates to a non-aqueous electrolyte additive, and a non-aqueous electrolyte for a lithium secondary battery including the same and a lithium secondary battery, and particularly, to a non-aqueous electrolyte additive having a nitrile group and a propargyl group, and a non-aqueous electrolyte for a lithium secondary battery and a lithium secondary battery, which include the non-aqueous electrolyte additive so that capacity and cycle lifespan characteristics at high temperature can be improved.
COMPOUND FOR ORGANIC PHOTOELECTRIC DEVICE AND ORGANIC PHOTOELECTRIC DEVICE IMAGE SENSOR, AND ELECTRONIC DEVICE INCLUDING THE SAME
A compound for an organic photoelectric device includes at least one of a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2 and a combination thereof.
Systems and methods for producing nitriles
An aspect of the present disclosure is a method that includes a first reacting a molecule from at least one of a carboxylic acid, an ester of a carboxylic acid, and/or an anhydride with ammonia to form a nitrile, where the first reacting is catalyzed using an acid catalyst. In some embodiments of the present disclosure, the molecule may include at least one of acetic acid, lactic acid, and/or 3-hydroxyproprionic acid (3-HPA). In some embodiments of the present disclosure, the molecule may include at least one of methyl acetate, ethyl lactate, and/or ethyl 3-hydroxypropanoate (ethyl 3-HP). In some embodiments of the present disclosure, the anhydride may be acetic anhydride.
Systems and methods for producing nitriles
An aspect of the present disclosure is a method that includes a first reacting a molecule from at least one of a carboxylic acid, an ester of a carboxylic acid, and/or an anhydride with ammonia to form a nitrile, where the first reacting is catalyzed using an acid catalyst. In some embodiments of the present disclosure, the molecule may include at least one of acetic acid, lactic acid, and/or 3-hydroxyproprionic acid (3-HPA). In some embodiments of the present disclosure, the molecule may include at least one of methyl acetate, ethyl lactate, and/or ethyl 3-hydroxypropanoate (ethyl 3-HP). In some embodiments of the present disclosure, the anhydride may be acetic anhydride.
SYSTEMS AND METHODS FOR PRODUCING NITRILES
An aspect of the present disclosure is a method that includes a first reacting a molecule from at least one of a carboxylic acid, an ester of a carboxylic acid, and/or an anhydride with ammonia to form a nitrile, where the first reacting is catalyzed using an acid catalyst. In some embodiments of the present disclosure, the molecule may include at least one of acetic acid, lactic acid, and/or 3-hydroxyproprionic acid (3-HPA). In some embodiments of the present disclosure, the molecule may include at least one of methyl acetate, ethyl lactate, and/or ethyl 3-hydroxypropanoate (ethyl 3-HP). In some embodiments of the present disclosure, the anhydride may be acetic anhydride.
SYSTEMS AND METHODS FOR PRODUCING NITRILES
An aspect of the present disclosure is a method that includes a first reacting a molecule from at least one of a carboxylic acid, an ester of a carboxylic acid, and/or an anhydride with ammonia to form a nitrile, where the first reacting is catalyzed using an acid catalyst. In some embodiments of the present disclosure, the molecule may include at least one of acetic acid, lactic acid, and/or 3-hydroxyproprionic acid (3-HPA). In some embodiments of the present disclosure, the molecule may include at least one of methyl acetate, ethyl lactate, and/or ethyl 3-hydroxypropanoate (ethyl 3-HP). In some embodiments of the present disclosure, the anhydride may be acetic anhydride.
Method for preparing acrylonitrile dimer
Provided is a method of preparing an acrylonitrile dimer, the method including: supplying an acrylonitrile monomer, a phosphorus-based catalyst, an alcohol solvent, and an ionic liquid to a reactor to perform a dimerization reaction to prepare a single-phase dimerization reaction product (S10); supplying a reactor discharge stream including the dimerization reaction product to a first distillation column, separating the alcohol solvent and an unreacted acrylonitrile monomer from an upper discharge stream, and supplying a lower discharge stream including an acrylonitrile dimer, the ionic liquid, and the phosphorus-based catalyst to a second distillation column (S20); and separating an upper discharge stream including the acrylonitrile dimer and separating a lower discharge stream including the ionic liquid and the phosphorus-based catalyst, from the second distillation column (S30).
Method for preparing acrylonitrile dimer
Provided is a method of preparing an acrylonitrile dimer, the method including: supplying an acrylonitrile monomer, a phosphorus-based catalyst, an alcohol solvent, and an ionic liquid to a reactor to perform a dimerization reaction to prepare a single-phase dimerization reaction product (S10); supplying a reactor discharge stream including the dimerization reaction product to a first distillation column, separating the alcohol solvent and an unreacted acrylonitrile monomer from an upper discharge stream, and supplying a lower discharge stream including an acrylonitrile dimer, the ionic liquid, and the phosphorus-based catalyst to a second distillation column (S20); and separating an upper discharge stream including the acrylonitrile dimer and separating a lower discharge stream including the ionic liquid and the phosphorus-based catalyst, from the second distillation column (S30).
RECYCLED CONTENT ORGANIC CHEMICAL COMPOUNDS FROM WASTE PLASTIC
Processes and facilities for producing several types of recycled content organic chemical compounds from waste plastic. Processing schemes are described herein for converting waste plastic (or hydrocarbon having recycled content derived from waste plastic) into useful intermediate chemicals and final products. In some aspects, recycled content aromatics (r-aromatics) can be processed to provide recycled content benzene (r-benzene) and/or recycled content toluene (r-toluene), which can be further processed to form a variety of intermediate and final organic chemical compounds including, but not limited to, recycled content nylons, recycled content polystyrene. recycled content benzoic acid, and recycled content phenol.