Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with nitro compounds

A liquid phase 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 a levulinic acid ester (I) with an alkyl nitro compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, in the presence of a solvent;
• wherein R2 is hydrocarbyl or substituted hydrocarbyl, C1-C18 unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, and wherein R4 is an alkyl group having from 1 to 30 carbons, and wherein R4 may be 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;
• and
• ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one pharmaceutically therapeutic agent.

A liquid phase 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 a levulinic acid ester (I) with an alkyl nitro compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, in the presence of a solvent;
• wherein R2 is hydrocarbyl or substituted hydrocarbyl, C1-C18 unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, and wherein R4 is an alkyl group having from 1 to 30 carbons, and wherein R4 may be 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;
• and
• ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one agrochemically effective agent.

A liquid phase 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 a levulinic acid ester (I) with an alkyl nitro compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, in the presence of a solvent;
• wherein R2 is hydrocarbyl or substituted hydrocarbyl, C1-C18 unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, and R4 is an alkyl group having from 1 to 30 carbons, and wherein R4 may be 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;
• and
• 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 liquid phase process for preparing an ink jet composition, the process comprising the steps of:

• i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting a levulinic acid ester (I) with an alkyl nitro compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, in the presence of a solvent;
• wherein R2 is hydrocarbyl or substituted hydrocarbyl, C1-C18 unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, and wherein R4 is an alkyl group having from 1 to 30 carbons, and wherein R4 may be 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;
• and
• ii) contacting 5-methyl-N-alkyl-2-pyrrolidine (VI) with at least one colorant.

A liquid phase 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 a levulinic acid ester (I) with an alkyl nitro compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, in the presence of a solvent;
• wherein R2 is hydrocarbyl or substituted hydrocarbyl, C1-C18 unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, and wherein R4 is an alkyl group having from 1 to 30 carbons, and wherein R4 may be C1-C3 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;
• and
• ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one refrigerant.