Production of 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with cyano compounds
AssigneeE. I. Du Pont de Nemours and Company
InventorLeo Ernest Manzer
Life of this patent
Estimating the term…
Abstract
This invention relates to a process for producing 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with aryl cyano compounds utilizing a metal catalyst, which is optionally supported.
Claims21
A process for preparing a reaction product comprising 5-methyl-(N-methyl aryl)-2-pyrrolidone (III), 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone, or a mixture thereof, the process comprising the step of contacting levulinic acid (I) with an aryl cyano compound (II), in the presence of hydrogen gas and a catalyst, the catalyst being optionally supported on a catalyst support, and, optionally, said contacting is performed in the presence of a solvent;
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- wherein R1 is an aromatic group having from 6 to 30 carbons and R2 is a fully or partially reduced derivative of R1.
A process for preparing a reaction product comprising 5-methyl-N-alkyl-2-pyrrolidone (VI), the process comprising the step of contacting levulinic acid (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a catalyst, the catalyst being optionally supported on a catalyst support, and, optionally, said contacting is performed in the presence of a solvent;
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- wherein R3 is C1-C30 unsubstituted or substituted alkyl, C1-C30 unsubstituted or substituted alkenyl, C1-C30 unsubstituted or substituted alkynyl, C3-C30 unsubstituted or substituted cycloalkyl, or C3-C30 unsubstituted or substituted cycloalkyl containing at least one heteroatom.
A process for preparing a pharmaceutical composition, the process comprising the steps of:
- i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting levulinic acid (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, optionally, in the presence of a solvent;
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- wherein R3 is C1-C30 unsubstituted or substituted alkyl, C1-C30 unsubstituted or substituted alkenyl, C1-C30 unsubstituted or substituted alkynyl, C3-C30 unsubstituted or substituted cycloalkyl, or C3-C30 unsubstituted or substituted cycloalkyl containing at least one heteroatom;
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- ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one pharmaceutically therapeutic agent.
A process for preparing an agrochemical composition, the process comprising the steps of:
- i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting levulinic acid (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, optionally, in the presence of a solvent;
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- wherein R3 is C1-C30 unsubstituted or substituted alkyl, C1-C30 unsubstituted or substituted alkenyl, C1-C30 unsubstituted or substituted alkynyl, C3-C30 unsubstituted or substituted cycloalkyl, or C3-C30 unsubstituted or substituted cycloalkyl containing at least one heteroatom;
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- ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one agrochemically effective agent.
A process for preparing a cleaning composition, the process comprising the steps of:
- i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting levulinic acid (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, optionally, in the presence of a solvent;
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- wherein R3 is C1-C30 unsubstituted or substituted alkyl, C1-C30 unsubstituted or substituted alkenyl, C1-C30 unsubstituted or substituted alkynyl, C3-C30 unsubstituted or substituted cycloalkyl, or C3-C30 unsubstituted or substituted cycloalkyl containing at least one heteroatom;
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- ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with a compound selected from the group consisting of anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, glycols, glycol ethers, aliphatic alcohols, alkanolamines, pyrrolidones, water, and mixtures thereof.
A process for preparing an ink jet ink composition, the process comprising the steps of:
- i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting levulinic acid (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, optionally, in the presence of a solvent;
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- wherein R3 is C1-C30 unsubstituted or substituted alkyl, C1-C30 unsubstituted or substituted alkenyl, C1-C30 unsubstituted or substituted alkynyl, C3-C30 unsubstituted or substituted cycloalkyl, or C3-C30 unsubstituted or substituted cycloalkyl containing at least one heteroatom;
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- ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one colorant.
A process for preparing a refrigerant or air conditioning lubricant, the process comprising the steps of:
- i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting levulinic acid (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, optionally, in the presence of a solvent;
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- wherein R3 is C1-C30 unsubstituted or substituted alkyl, C1-C30 unsubstituted or substituted alkenyl, C1-C30 unsubstituted or substituted alkynyl, C3-C30 unsubstituted or substituted cycloalkyl, or C3-C30 unsubstituted or substituted cycloalkyl containing at least one heteroatom;
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- ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one refrigerant.
Dependencies are inferred from the claim text.