IP Library Granted Patent US 7,482,495
Granted Patent B2
US 7,482,495 · App. 11/316,147 · Granted Jan 27, 2009

Process for making alkylene glycol ether compositions useful for metal recovery

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Quick Facts
Patent No.
US 7,482,495
App. No.
11/316,147
Granted
Jan 27, 2009
Kind
B2
Abstract

A process for making an alkylene glycol ether composition is disclosed. In one aspect, the process comprises reacting propylene glycol methyl ether (PM) with from 1.5 to 3 equivalents of propylene oxide (PO). The resulting alkoxylation mixture is distilled to provide a composition comprising at least 30 wt. % of TPM and less than 20 wt. % of DPM. In another process of the invention, DPM reacts with from 0.5 to 1.5 equivalents of PO in similar fashion to make an analogous product. Also disclosed are alkylene glycol ether compositions made by the process of the invention and use of the compositions in a method for recovering metals from metallic ores by froth flotation.

Claims (12)

1. A process which comprises:

(a) reacting propylene glycol methyl ether (PM) with from 1.5 to 3 equivalents of propylene oxide in the presence of an alkoxylation catalyst to produce an alkoxylation mixture comprising PM, dipropylene glycol methyl ethers (DPM), tripropylene glycol methyl ethers (TPM), and higher PM propoxylates; and

(b) distilling PM and DPM from the alkoxylation mixture to provide an alkylene glycol ether composition comprising at least 30 wt. % of TPM and from 4 to 12 wt. % of DPM.

2. A glycol ether composition made by the process of claim 1 .

3. A froth flotation method which comprises recovering a metal from a metallic ore in the presence of a frothing agent comprising the composition of claim 2 .

4. The method of claim 3 wherein the metal is selected from the group consisting of platinum and copper.

5. A process which comprises:

(a) reacting DPM with from 0.5 to 1.5 equivalents of propylene oxide in the presence of an alkoxylation catalyst to produce an alkoxylation mixture comprising DPM, TPM, and higher DPM propoxylates; and

(b) distilling DPM from the alkoxylation mixture to provide an alkylene glycol ether composition comprising at least 30 wt. % of TPM and from 4 to 12 wt. % of DPM.

6. An alkylene glycol ether composition made by the process of claim 5 .

7. A froth flotation method which comprises recovering a metal from a metallic ore in the presence of a frothing agent comprising the composition of claim 6 .

8. The method of claim 7 wherein the metal is selected from the group consisting of platinum and copper.

Assignments (20)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2005
From: FADAKAR, FARHAD
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 017409/0014 →