IP Library › Granted Patent US 6,982,337
Granted Patent B1
US 6,982,337 · App. 10/900,963 · Granted Jan 3, 2006

Process for making N-vinyl-2-pyrrolidone

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Quick Facts
Patent No.
US 6,982,337
App. No.
10/900,963
Granted
Jan 3, 2006
Kind
B1
Abstract

A process for making N-vinyl-2-pyrrolidone (NVP) is disclosed. The process comprises dehydrating N-(2-hydroxyethyl)-2-pyrrolidone (HEP) in the presence of a catalyst and added water. Adding an effective amount of water into the dehydration process reduces the amount of N-ethyl-2-pyrrolidone (NEP) formed compared with the amount produced in the absence of the added water. Adding water can also sustain high conversions of HEP, minimize heavies formation, and improve selectivity to NVP. The process provides high-purity NVP and avoids a costly crystallization step.

Claims (9)

1. A process which comprises dehydrating N-(2-hydroxyethyl)-2-pyrrolidone (HEP) in the presence of a catalyst and added water to produce N-vinyl-2-pyrrolidone (NVP), wherein the water is used in an amount effective to reduce the amount of N-ethyl-2-pyrrolidone (NEP) produced compared with the amount of NEP produced in the absence of the added water.

2. The process of claim 1 wherein conversion of HEP is enhanced by adding the water.

3. The process of claim 1 wherein selectivity to NVP is enhanced by adding the water.

4. The process of claim 1 wherein production of nonvolatile by-products is reduced by adding the water.

5. The process of claim 1 wherein the water is added in an amount within the range of 0.5 to 20 wt. % based on the amount of HEP.

6. The process of claim 1 wherein the water is added in an amount within the range of 2 to 10 wt. % based on the amount of HEP.

7. The process of claim 1 wherein the catalyst is cesium on silica.

8. The process of claim 1 wherein the yield of NVP exceeds 80%.

9. The process of claim 1 wherein the amount of NEP produced is reduced by at least 50% compared with the amount of NEP produced in the absence of the added water.

Assignments (21)
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032123/0799 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: CITIBANK, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032125/0296 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032137/0156 →
APPOINTMENT OF SUCCESSOR ADMINISTRATIVE AGENT Recorded Jan 23, 2014
From: UBS AG, STAMFORD BRANCH
To: BANK OF AMERICA, N.A.
Reel/Frame 032137/0639 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: BANK OF AMERICA, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032138/0134 →
SECURITY AGREEMENT Recorded May 19, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 024402/0681 →
SECURITY AGREEMENT Recorded May 18, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024397/0818 →
SECURITY AGREEMENT Recorded May 7, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 024342/0801 →
SECURITY AGREEMENT Recorded May 6, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 024342/0421 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0856 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.; EQUISTAR CHEMICALS, LP
Reel/Frame 024337/0705 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0285 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0020 →
SECURITY AGREEMENT Recorded Oct 30, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 023449/0138 →
SECURITY AGREEMENT Recorded Apr 9, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
Reel/Frame 022708/0830 →
SECURITY AGREEMENT Recorded Aug 4, 2008
From: BASELL POLYOLEFINE GMBH; ARCO CHEMICAL TECHNOLOGY L.P.; ARCO CHEMICAL TECHNOLOGY, INC.; ATLANTIC RICHFIELD COMPANY; BASELL NORTH AMERICA, INC.; BASELL POLYOLEFIN GMBH; LYONDELL CHEMICAL COMPANY; EQUISTAR CHEMICALS, L.P.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021354/0708 →
GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AND PATENT APPLICATIONS Recorded Mar 26, 2008
From: BASELL POLYOLEFINE GMBH; ARCO CHEMICAL TECHNOLOGY L.P.; ARCO CHEMICAL TECHNOLOGY, INC.; ATLANTIC RICHFIELD COMPANY; BASELL NORTH AMERICA, INC.; EQUISTAR CHEMICALS. LP.; LYONDELL CHEMICAL COMPANY; LYONDELL CHEMICAL TECHNOLOGY, L.P.; LYONDELL PETROCHEMICAL COMPANY; NATIONAL DISTILLERS AND CHEMICAL CORPORATION; OCCIDENTAL CHEMICAL CORPORATION; OLIN CORPORATION; QUANTUM CHEMICAL CORPORATION; BASELL POLYOLEFIN GMBH
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 020704/0562 →
RELEASE OF LYONDELL CHEMICAL TECHNOLOGY, L.P. PATENT SECURITY AGREEMENT Recorded Mar 20, 2008
From: JPMORGAN CHASE BANK, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 020679/0063 →
SECURITY AGREEMENT Recorded Sep 15, 2006
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: JPMORGAN CHASE BANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 018260/0306 →
CHANGE OF NAME Recorded Jun 27, 2005
From: ARCO CHEMICAL TECHNOLOGY, L.P.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 016206/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2004
From: KAHN, ANDREW P.
To: ARCO CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 015639/0031 →