IP Library Granted Patent US 10,370,320
Granted Patent B2
US 10,370,320 · App. 16/221,881 · Granted Aug 6, 2019

Purification methods

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Quick Facts
Patent No.
US 10,370,320
App. No.
16/221,881
Granted
Aug 6, 2019
Kind
B2
Abstract

Provided are purification methods, comprising: (a) providing an organic solvent and a phenolic peroxide formation inhibitor, wherein the organic solvent has a first boiling point at standard atmospheric pressure (bp 1 ) and the phenolic peroxide formation inhibitor has a second boiling point at standard atmospheric pressure (bp 2 ) that satisfy the following inequality (I): bp 2 ≤(1.10)(bp 1 )  (I); and (b) heating the organic solvent and the phenolic peroxide formation inhibitor to a temperature causing the organic solvent and phenolic peroxide formation inhibitor to vaporize, and (ii) condensing the vaporized organic solvent and peroxide formation inhibitor to provide a purified mixture of the organic solvent and peroxide formation inhibitor. The methods find particular use in the purification of solvents that are useful in process chemicals for the manufacture of semiconductor devices.

Claims (14)

1. A purification method, comprising:

(a) providing an organic solvent and a phenolic peroxide formation inhibitor, wherein the organic solvent has a first boiling point at standard atmospheric pressure (bp 1 ) and the phenolic peroxide formation inhibitor has a second boiling point at standard atmospheric pressure (bp 2 ) that satisfy the following inequality (I):

bp 2 ≤(1.10)(bp 1 )  (I); and

(b) heating the organic solvent and the phenolic peroxide formation inhibitor to a temperature causing the organic solvent and phenolic peroxide formation inhibitor to vaporize, and (ii) condensing the vaporized organic solvent and phenolic peroxide formation inhibitor to provide a purified mixture of the organic solvent and phenolic peroxide formation inhibitor.

2. The purification method of claim 1 , wherein the purification method is a distillation process.

3. The purification method of claim 1 , wherein the purification method is performed under vacuum.

4. The purification method of claim 1 , wherein the organic solvent and the phenolic peroxide formation inhibitor are mixed prior to the step of heating.

5. The purification method of claim 1 , wherein the phenolic peroxide formation inhibitor has a second boiling point at standard atmospheric pressure (bp 2 ) that satisfies the following inequality (II):

(0.90)(bp 1 )<bp 2 <(1.10)(bp 1 )  (II).

6. The purification method claim 1 , wherein bp 2 is less than bp 1 .

7. The purification method of claim 1 , wherein the phenolic peroxide formation inhibitor is chosen from phenol, 2-methylphenol, 2-(trifluoromethyl)phenol, 4-methoxyphenol, 4-(trifluoromethoxy)phenol, 2,4-dimethyl-6-tert-butylphenol, 2,4-di(trifluoromethyl)-6-tert-butylphenol, 2,6-di-tert-butylphenol, 4-tert-butylpyrocatechol, and combinations thereof.

8. The purification method of claim 7 , wherein the phenolic peroxide formation inhibitor is chosen from 2-methylphenol, 2,4-dimethyl-6-tert-butylphenol, and combinations thereof.

9. The purification method of claim 1 , wherein the organic solvent is chosen from one or more of isoamyl ether, 2-butoxyethanol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, tripropylene glycol monomethyl ether, ethyl-3-ethoxy propionate, ethyl lactate, propylene glycol, tripropylene glycol, diisopropyl benzene, triisopropyl benzene, cyclopentanone, cyclohexanone and combinations thereof.

10. The purification method of claim 9 , wherein the organic solvent is tripropylene glycol monomethyl ether and the phenolic peroxide formation inhibitor is 2,4-dimethyl-6-tert-butylphenol, or wherein the solvent is dipropylene glycol methyl ether and the phenolic peroxide formation inhibitor is 2-methylphenol.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2019
From: RUDENKO, ANDREY; POHLERS, GERHARD
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 048135/0373 →