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US 6,632,951 B2Granted
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.
Claims4
A method of making a compound having the formula:
- wherein
- R1, R2, R4, and R5 are, independently, H or a C1 to C6 alkyl or substituted alkyl;
- and R3 is H or a C1 to C6 alkyl or substituted alkyl;
- comprising a first step of reacting a composition comprising:
- a compound having the formula:
- 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 an ammonia source,
- in the presence of water, to form a compound having the formula:
- 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;
- 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 a catalyst.
16 more elements
Dependencies are inferred from the claim text.