IP Library Granted Patent US 7,858,381
Granted Patent B2
US 7,858,381 · App. 11/475,086 · Granted Dec 28, 2010

Process for preparing high-purity, halogen-free o-phthaladehyde

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Quick Facts
Patent No.
US 7,858,381
App. No.
11/475,086
Granted
Dec 28, 2010
Kind
B2
Abstract

Improved process for preparing high-purity, halogen-free o-phthalaldehyde, in which a) tetrahalo-o-xylene is hydrolyzed at a temperature of 155-160° C. and a pressure of from 2 to 5 bar, where appropriate in the presence of a phase-transfer catalyst, to o-phthalaldehyde, which b) is converted in an acidic alcoholic solution at a temperature of from 0 to the reflux temperature into the corresponding dialkoxyphthalane and, subsequently, c) an acetal cleavage is effected by acid hydrolysis at a pH >1.5 to pH 7, resulting in high-purity, halogen-free o-phthalaldehyde.

Claims (8)

1. A process for preparing high-purity, halogen-free o-phthalaldehyde, which comprises:

a) hydrolyzing tetrahalo-o-xylene at a temperature of 155-160° C. and a pressure of from 2 to 5 bar, optionally in the presence of a phase-transfer catalyst, to o-phthalaldehyde,

b) converting the o-phthalaldehyde in an acidic alcoholic solution at a temperature of from 0 to the reflux temperature into the corresponding dialkoxyphthalane and, subsequently,

c) cleaving acetals by acid hydrolysis at a pH between 1.5 to 7, resulting in high-purity, halogen-free o-phthalaldehyde.

2. The process as claimed in claim 1 , wherein step a) is carried out in a C 1 -C 4 carboxylic acid in the presence of a base and water.

3. The process as claimed in claim 2 , wherein the amount of carboxylic acid employed is between 4 to 20 mole equivalents based on tetrahalo-o-xylene.

4. The process as claimed in claim 1 , wherein step b) takes place at a pH of between 0 and 3.

5. The process as claimed in claim 1 , wherein step c) takes place at a pH of between 1.6 and 2.5.

Assignments (7)
RELEASE (REEL 032424 / FRAME 0001) Recorded Sep 28, 2017
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: DSM FINE CHEMICALS AUSTRIA NFG GMBH & COKG
Reel/Frame 044037/0879 →
NOTICE OF SUCCESSION OF AGENCY FOR PATENT SECURITY INTEREST PREVIOUSLY RECORDED AT REEL/FRAME (032424/0001) Recorded Jul 12, 2017
From: UBS AG, STAMFORD BRANCH, AS PRIOR AGENT
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SUCCESSOR AGENT
Reel/Frame 043165/0987 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2016
From: DPX FINE CHEMICALS AUSTRIA GMBH & CO KG
To: ESIM CHEMICALS GMBH
Reel/Frame 037650/0836 →
CHANGE OF NAME Recorded Feb 3, 2016
From: DSM FINE CHEMICALS AUSTRIA NFG GMBH & CO KG
To: DPX FINE CHEMICALS AUSTRIA GMBH & CO KG
Reel/Frame 037650/0811 →
RELEASE OF SECURITY INTEREST Recorded Sep 1, 2015
From: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: DSM FINE CHEMICALS AUSTRIA NFG GMBH & COKG
Reel/Frame 036466/0572 →
SECURITY INTEREST Recorded Mar 11, 2014
From: DSM FINE CHEMICALS AUSTRIA NFG GMBH & COKG
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 032424/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2006
From: GISELBRECHT, KARLHEINZ; REITER, KLAUS; HERMANSEDER, RUDOLF
To: DSM FINE CHEMICALS AUSTRIA NFG GMBH & CO KG
Reel/Frame 018019/0920 →