Methods of making pyrrolidones
AssigneeBattelle Memorial Institute
InventorsTodd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
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Abstract
The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
Claims27
A method of making a compound having the formula (C) below:
- wherein R1, R2, R4, and R5 are, independently, H or a C1 to C6 alkyl or substituted alkyl;
- and wherein R3 is H or a C1 to C6 alkyl or substituted alkyl;
- the method comprising reacting an initial compound with an alcohol and hydrogen in the presence of water and a catalyst, the initial compound having the formula (B) below:
- wherein R1, R2, R4, and R5 are, independently, H or a C1 to C6 alkyl or substituted alkyl, or wherein R2 and R4 together are replaced by a double bond;
- R3 is H or a C1 to C6 alkyl or substituted alkyl;
- and X and Y are, independently, OH, O−, or where X and Y together are a bridging oxo;
- and
- wherein the catalyst comprises carbon, metal oxide and at least one metal selected from the group consisting of Pd, Rh, Pt, Ru, Ni and Co.
A method of producing a compound having formula (C) below:
- wherein R1, R2, R4, and R5 are, independently, H or a C1 to C6 alkyl or substituted alkyl;
- and wherein R3 is H or a C1 to C6 alkyl or substituted alkyl, the method comprising:
- a first step of reacting a compound of formula (B)
- with ammonia in the presence of water, to form a compound of formula (A);
- a second step of extracting the compound of formula (A) into an organic solvent;
- and
- a third step comprising hydrogenating the compound of formula (A) that was extracted in the second step in the presence of the catalyst.
A method of producing N-methyl pyrrolidone comprising:
- providing a catalyst comprising a first metal, an oxide material comprising a second metal and a carbon support, the second metal comprising at least one member of the group consisting of Zr, Hf, Ta, Nb, Mo, W, Zn, Sn, V, Fe, U and Th;
- and
- flowing an aqueous solution comprising succinimide over the catalyst in the presence of hydrogen to catalytically hydrogenate the succinimide, the hydrogenation forming N-methyl pyrrolidone and 2-pyrrolidone, a product ratio of N-methyl pyrrolidone to 2-pyrrolidone being greater than 5:1.
A method of forming a pyrrolidone compound comprising:
- forming a solution comprising an initial compound having the formula below:
- providing the solution into a reactor containing a catalyst comprising a metal oxide, the metal oxide having at least one metal selected from the group consisting of Zr, Hf, Ta, Nb, Mo, W, Zn, Sn, V, Fe, U and Th;
- flowing hydrogen into the reactor;
- and
- reacting the hydrogen with the initial compound in the presence of the catalyst, the reaction converting the initial compound into the pyrrolidone compound.
The method of claim wherein R1, R2, R4, and R5 are all H.
Dependencies are inferred from the claim text.