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METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUNDS

Publication No. EP4212499

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App No. EP22213722

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Filed by Solstice Advanced Materials US, Inc.

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Filed on 2007-01-03

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Issued/Published on 2026-03-04

Official EPO Register

Publication No. EP4212499 A1

Application No. EP22213722 Filed: 2007-01-03

Grant Date 2026-03-04 Mention of grant

Active Oppositions 1 Active EPO Oppositions

Patent Abstract / Summary

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 CFaCCI=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, SbCls/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%.

IPC Classifications

C07C17/087, C07C21/18, C07C17/04, C07C19/01, C07C17/06, C07C19/10, C07C17/20, C07C17/21, C07C17/25

Priority Claims

US 200675548506P Date: 2006-01-03

Designated Contracting States (31 EPC States)

AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

Parties & Representation

Applicants

Solstice Advanced Materials US, Inc.

115 Tabor Road, Morris Plains, NJ 07950

Honeywell International Inc.

115 Tabor Road, Morris Plains, NJ 07950

Inventors (9)

MERKEL, Daniel

West Seneca, 14224

TUNG, Hsueh Sung

Getzville, 14068

VAN DER PUY, Michael

Amherst, 14221

MA, Jing Ji

Morristown, 07962

DUBEY, Rajesh

Buffalo, 14210

LIGHT, Barbara

Niagra Falls, 14305

BORTZ, Cheryl

N Tonawanda, 14120

PHILLIPS, Steven D

Buffalo, 14218

MUKHOPAHYAY, Sudip

Morristown, 07962

Representatives / Agents

Abthorpe, Mark

Kilburn & Strode LLP, Lacon London

Stepney, Gregory John

Withers & Rogers LLP, 2 London Bridge

Sarpi, Maurizio, et al

Studio Ferrario S.r.l., Via Collina, 36

Key Procedural Dates

Request-For-Examination 2024-01-19

First-Examination-Report-Despatched 2024-07-31

Mention Of Grant Published 2026-03-04

Patent & Non-Patent Citations

Cited documents and prior art referenced in search and examination reports.

16 Citations

Cited Patent Documents

US4900874

Espacenet

US2931840

Espacenet

US5162594

Espacenet

US75548506

Espacenet

EP4212499 2023-07-19

Espacenet

EP3336074 2018-06-20

Espacenet

EP2546225 2013-01-16

Espacenet

WO2007079431 2007-07-12

Espacenet

US2996555 1961-08-15

Espacenet

US2006106263 2006-05-18

Espacenet

EP0939071 1999-09-01

Espacenet

Non-Patent Scientific Literature (NPL)

- BANKS ET AL., JOURNAL OF FLUORINE CHEMISTRY, vol. 82, no. 2, 1997, pages 171 - 174

- HENNE ALBERT L ET AL: "Fluorinated derivatives of propane and propylene. VI", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 68, 1 January 1946 (1946-01-01), pages 496 - 497, XP002448570, ISSN: 0002-7863, DOI: 10.1021/JA01207A041

- PALETA OLDRICH ET AL: "Synthesis of perfluoroallyl chloride and some chlorofluoropropenes", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, SOCIETY FRANCAISE DE CHIMIE , PARIS, FRANCE, no. 6, 1 January 1986 (1986-01-01), pages 920 - 924, XP009088473, ISSN: 0037-8968

- MARIA O BURGIN ET AL: "UNIMOLECULAR REACTION KINETICS OF CF2CLCF2CH3 AND CF2CLCF2CD3: EXPERIMENTAL EVIDENCE FOR A NOVEL 1,2-FCL REARRANGEMENT PATHWAY", THE JOURNAL OF PHYSICAL CHEMISTRY A, WASHINGTON DC, US, vol. 105, 1 January 2001 (2001-01-01), pages 1615 - 1621, XP002448571, ISSN: 1089-5639, DOI: 10.1021/JP002511D

- "Fundamentals of Organic Chemistry, 3rd ed.", 1 June 2005, HIGHER EDUCATION PRESS , ISBN: 978-7-04-016637-8, article QIYI XING, PEI WEIWEI, XU RUIQUI, PEI JIAN: "Fundamentals of Organic Chemistry (English translation enclosed)", pages: 319 - 321, XP055822804

Official File Inspection EPC Art. 128 Public Dossier

Complete European Patent Register Dossier (148 Total Documents)

The full inspection file for Application EP22213722 contains 148 total documents, including all notices of opposition, proprietor counter-statements, examination communications, third-party observations, and procedural forms. Below are all major recorded procedural filings and publication specifications.

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METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUNDS

Patent Abstract / Summary

IPC Classifications

Priority Claims

Designated Contracting States (31 EPC States)

Parties & Representation

Applicants

Inventors (9)

Representatives / Agents

Key Procedural Dates

Patent Oppositions

Zhejiang Huanxin Fluoro Material Co., Ltd.

Legal Status & Event History

Patent & Non-Patent Citations

Cited Patent Documents

Non-Patent Scientific Literature (NPL)

Worldwide Patent Family

Complete European Patent Register Dossier (148 Total Documents)

Recorded Filings & Patent Specifications

European Patent Specification - Granted Patent (B1)

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