Isolation of products from selective dehalogenation of haloaromatics

US6303812A · kind A · utility

Assignee

• Occidental Chemical Corporation · US

Inventors

• Michael J. Fifolt · Grand Island, US
• Michael C. Savidakis · Niagara Falls, US
• Ronald F. Spohn · Getzville, US
• Daniel R. Thielen · Snyder, US
• William S. Derwin · Grand Island, US
• David C. Johnson · Eugene, US

Key dates

• Filing date: Feb 15, 2000
• Grant date: Oct 16, 2001
• Expiry date: Feb 15, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C67/48
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Disclosed is a method of isolating the aromatic product formed when a substrate having the general formula ##STR1## is dehalogenated, forming a product mixture of copper salts and aromatic product, where X is the halogen removed from the substrate to form the aromatic product, R' is COOH, COOR, COR, CN, COH(R).sub.2, or SO.sub.3 H, each R" is independently selected from halogen, R, or OR or two vicinal R" groups form one or more fused aromatic rings, R is alkyl from C.sub.1 to C.sub.18 or aryl from C.sub.6 to C.sub.18, and n is 1 to 4. Water in an amount about 1 to about 5 times the amount of the substrate is added to the product mixture, forming an organic phase that contains the aromatic product and an aqueous phase that contains the copper salts. If the density of the organic phase differs from the density of said aqueous phase by less than 0.1 g/cc, a suitable solvent is added to the product mixture in an amount sufficient to increase the differences between the organic and aqueous phases to at least 0.1 g/cc. The organic phase can be separated from the aqueous phase by decantation.