Method for producing fluorinated organic compounds

US8084653B2 · kind B2 · utility

Assignee

• HONEYWELL INTERNATIONAL INC. · US

Inventors

• Hsueh Sung Tung · Getzville, US
• Sudip Mukhopadhyay · Williamsville, US
• Michael Van Der Puy · Amherst, US
• Daniel C. Merkel · West Seneca, US
• Jing Ji Ma · West Seneca, US
• Cheryl L. Bortz · North Tonawanda, US
• Barbara A. Light · Niagara Falls, US
• Steven D. Phillips · Avon, US
• Rajesh Dubey · Maraimalai Nagar, IN

Key dates

• Filing date: Jan 3, 2007
• Grant date: Dec 27, 2011
• Expiry date: Oct 25, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C21/18
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl═CH2, preferably in a 80-96% selectivity. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.