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US 2003/0120087 A1Published application
Methods of making pyrrolidones
AssigneeBattelle Memorial Institute
InventorsTodd Werpy, John G. Frye JR., Yong Wang, Alan H. Zacher
Life of this patent
Estimating the term…
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.
Claims35
A method of making a compound having the formula:
- 4
- 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 reacting a composition comprising:
- a compound having the formula:
- 5
- 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 hydrogen,
- in the presence of water and a catalyst;
- 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.
10 more elements
A method of making a compound having the formula:
- 6
- 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 reacting a composition comprising:
- a compound having the formula:
- 7
- 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;
- and hydrogen;
- in the presence of a catalyst comprising a metal selected from the group consisting of Pd, Rh, Pt, Ru, Ni and Co;
- at a temperature of less than 220° C. and for a time of less than 10 hours;
- wherein compound (C) is obtained in a yield of at least 80%, based on the initial amount of (A).
9 more elements
A method of making a compound having the formula:
- 9
- 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:
- 10
- 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:
- 11
- 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
A method of making a compound having the formula:
- 12
- 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 reacting a composition comprising:
- a compound having the formula:
- 13
- 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 hydrogen,
- in the presence of water and a catalyst;
- to obtain a product mixture comprising a compound (C) precursor;
- separating the compound (C) precursor from the catalyst, or from hydrogen, or from both the catalyst and hydrogen, to form a separated compound (C) precursor;
- and
- hydrolyzing the separated compound (C) precursor.
13 more elements
Dependencies are inferred from the claim text.