IP Library Granted Patent US 7,045,639
Granted Patent B2
US 7,045,639 · App. 10/941,134 · Granted May 16, 2006

Method for purifying N-(2-hydroxyethyl)-2-pyrrolidone

Assignee: Lyondell Chemical Technology, L.P.
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Quick Facts
Patent No.
US 7,045,639
App. No.
10/941,134
Granted
May 16, 2006
Kind
B2
Abstract

A method for purifying N-(2-hydroxyethyl)-2-pyrrolidone (HEP) is disclosed. The method comprises crystallizing crude HEP to produce HEP crystals and a mother liquor, and separating the HEP crystals from the mother liquor. In one method of the invention, crystallization is induced by adding an HEP seed crystal to the crude HEP. In a preferred method, the crystallization is performed in the presence of 1–4 wt. % of added water. HEP can be successfully crystallized to a purity greater than 99.9%.

Claims (19)

1. A method which comprises: (a) crystallizing liquid, crude N-(2-hydroxyethyl)-2-pyrrolidone (HEP) by adding an HEP seed crystal to produce HEP crystals and a mother liquor; and (b) separating the HEP crystals from the mother liquor.

2. The method of claim 1 wherein the crystallization is performed at room temperature.

3. The method of claim 1 performed in the presence of 1 to 4 wt. % of water based on the amount of crude HEP.

4. The method of claim 3 performed in the presence of 2 to 3 wt. % of water based on the amount of crude HEP.

5. The method of claim 3 wherein the crude HEP/water mixture is chilled to less than −5° C. to induce crystallization.

6. The method of claim 5 wherein the crude HEP/water mixture is chilled to less than −10° C. to induce crystallization.

7. The method of claim 5 wherein the HEP crystals have a purity greater than 99%.

8. The method of claim 5 wherein the HEP crystals have a purity greater than 99.9%.

9. A method which comprises: (a) crystallizing liquid, crude N-(2-hydroxyethyl)-2-pyrrolidone (HEP) in the presence of 1 to 4 wt. % of water based on the amount of crude HEP at a temperature less than −5° C. to produce HEP crystals and a mother liquor; and (b) separating the HEP crystals from the mother liquor, wherein the HEP crystals have a purity greater than 99%.

10. The method of claim 9 wherein the crystallization is performed in the presence of 2 to 3 wt. % of water.

11. The method of claim 9 wherein the crystallization is performed at a temperature less than −10° C.

12. The method of claim 9 wherein the HEP crystals have a purity greater than 99.9%.

13. A method which comprises: (a) crystallizing liquid, crude N-(2-hydroxyethyl)-2-pyrrolidone (HEP) in the presence of 1 to 4 wt. % of water based on the amount of crude HEP to produce HEP crystals and a mother liquor; and (b) separating the HEP crystals from the mother liquor.

14. The method of claim 13 wherein the crude HEP is crystallized in the presence of 2 to 3 wt. % of water based on the amount of crude HEP.

15. The method of claim 13 wherein the crude HEP/water mixture is chilled to less than −5° C. to induce crystallization.

16. The method of claim 15 wherein the crude HEP/water mixture is chilled to less than −10° C. to induce crystallization.

17. The method of claim 13 wherein the HEP crystals have a purity greater than 99%.

18. The method of claim 13 wherein the HEP crystals have a purity greater than 99.9%.

19. The method of claim 13 wherein crystallization is repeated until HEP of a desired purity is obtained.

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 Sep 15, 2004
From: KAHN, ANDREW P.; CAREY, EDWARD P.
To: ARCO CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 015806/0618 →
Continuity (1)
Related Publication 20060058534A1 · Mar 16, 2006