# US 10,308,603 B2 · Process for the selective production of N-methyl-2-pyrrolidone (NMP)

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- Number: US 10,308,603 B2
- Document ID: US10308603B2
- Status: Granted
- Kind: B2
- Application number: 15/749,426
- Filed: 2016-05-17
- Published: 2018-08-09
- Granted: 2019-06-04
- Earliest claimed: 2015-07-31
- Assignees: Council of Scientific and Industrial Research
- Applicants: Council of Scientific & Industrial Research
- Inventors: Indrajit Kumar Ghosh; Suman Lata Jain; Praveen Kumar Khatri; Siddharth Sankar Ray; Madhukar Onkarnath Garg
- Web page: https://patentgrep.com/patent/US10308603B2

## CPC

- C07D 207/267: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
- B01J 29/061: {containing metallic elements added to the zeolite}
- B01J 29/076: containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J 29/90: Regeneration or reactivation
- B01J 35/615: {100-500 m2/g}
- Y02P 20/584: Recycling of catalysts
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

This invention relates to an improved process for the selective production of N-methyl pyrrolidone (NMP) from gamma-butyrolactone and monomethyl amine preferably in aqueous form in the presence of a catalyst under comparatively milder conditions than the processes well known in the prior art of literature. The process is economically viable as it provides higher yield and selectivity for NMP which reduces the cost of separation of NMP from GBL. The catalyst shows good recyclability without significant loss in catalytic activity and no frequent regeneration is required.

## Claims

### Claim 1

A process for selective production of N-methyl-2-pyrrolidone (NMP) comprising:
a) reacting feedstock monomethyl amine (MMA) and gamma-butyrolactone (GBL) in a single step in a continuously stirred tank reactor (CSTR) at a molar ratio of MMA to GBL in the range of 1 to 2, in the presence of catalyst wherein the catalyst comprises 5-15% of Al and consists of a bronsted acidic support which is a class of zeolitic material with SiO2 to Al2O3 molar ratio of 70 to 100 having specific surface area of 400 to 500 m2/g and modified by oxide of one or more metals selected from Zr and W to the percentage of metal loading of 1 to 30 parts by weight of the support with catalyst content between 1 to 10% of total feedstock, at operating condition of temperature 130 to 250° C. and pressure 5 to 70 at 500 to 1000 agitator speed, for a period of 30 to 180 minutes to obtain a reaction mixture;
b) cooling the reaction mixture to a temperature in the range of 20 to 25° C.;
c) separating the catalyst from the reaction mixture of step b) by known methods;
d) separating the product from reaction mixture of step c) by evaporation or distillation to obtain NMP at selectivity to ≥99% at a conversion of GBL to ≥98%; and
e) recycling the catalyst to reactor after repeating the steps a) to d) several times.

### Claim 2 (depends on 1)

The process of claim 1, wherein said MMA is in aqueous form.

### Claim 3 (depends on 2)

The process of claim 2, wherein said MMA is in concentration by weight of up to 40%.

### Claim 4 (depends on 1)

The process of claim 1, wherein percentage weight of metal loading in catalyst is 5 to 20.

### Claim 5 (depends on 4)

The process of claim 4, wherein percentage weight of metal loading in catalyst is 10 to 15.

### Claim 6 (depends on 1)

The process of claim 1, wherein the support used in the formulation of the catalyst has SiO2 to Al2O3 molar ratio of 80 to 90 and specific surface area of 420 to 450 m2/g.

### Claim 7 (depends on 1)

The process of claim 1, wherein amount of catalyst used with respect to the total feed is in a range of 1 to 5% by wt.

### Claim 8 (depends on 1)

The process of claim 1, wherein the catalyst used is in the form of powder to a particle size of 20-30 mesh.

### Claim 9 (depends on 1)

The process of claim 1, wherein the catalyst used for several runs is recycled back after stirring with a solvent at temperature 60-90° C. under reflux and drying in oven for a period of 6 to 12 hours at 80 to 110° C.

### Claim 10 (depends on 9)

The process of claim 9, wherein the solvent used for the washing of the catalyst for recycled use is a low boiling chemical.

### Claim 11 (depends on 10)

The process of claim 10, wherein the low boiling chemical is acetone, dimethylene chloride, benzene, or petroleum ether.

### Claim 12 (depends on 1)

The process of claim 1, wherein purity of NMP is 99.99%.

### Claim 13 (depends on 1)

The process of claim 1, wherein recovered unreacted monomethyl amine is recycled back.