WO1997007083A1 - Process for the preparation of halogenated alkanes - Google Patents
Process for the preparation of halogenated alkanes Download PDFInfo
- Publication number
- WO1997007083A1 WO1997007083A1 PCT/US1996/012341 US9612341W WO9707083A1 WO 1997007083 A1 WO1997007083 A1 WO 1997007083A1 US 9612341 W US9612341 W US 9612341W WO 9707083 A1 WO9707083 A1 WO 9707083A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- haloalkane
- stream
- catalyst
- product
- cocatalyst
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
Definitions
- the present invention relates to a process for the preparation of halogenated alkanes.
- the present invention provides a process for the highly selective preparation of haloalkanes in good yield.
- HCC-240 1, 1,1,3,3-pentachloropropane
- Kotora et al. "Addition of Tetrachloromethane to Halogenated Ethenes Catalyzed by Transition Metal Complexes", 77 J. Molec. Catal. 51 - 60 (1 92) disclose the preparation of HCC-240 from carbon tetrachloride and vinyl chloride using both cuprous chloride and Cu[(CH 3 -CN) ]ClO 4 complexes with an n-butylamine cocatalyst. Catalyst and cocatalyst removal is achieved by water wash which destroys the catalyst. Additionally, the use of perchlorates in the process poses handling problems because perchlorates are extremely explosive.
- the present invention provides a highly selective process for the production of halogenated alkanes in good yield in which process unreacted materials may be recycled. More specifically, the invention provides a process for producing halogenated alkanes which halogenated alkanes include, without limitation, prior art haloalkanes such as HCC-240 as well as haloalkanes not seen in the prior art such as pentachlorobutane (“HCC-360”) and heptachlorohexane (“HCC-580"). HCC-240, 360, and 580 may be used as intermediates for the production of
- HFC-245fa 1, 1, 1,3,3-pentafluoropropane
- HFC-365 pentafluorobutane
- HFC-587 heptafluorohexane
- the process of this invention uses a catalyst with an organic ligand cocatalyst, flash distillation of organic feeds, catalyst filtration and recycle, and vacuum distillation, optionally in the presence of a metal chelating compound, to produce and recover product in high yield.
- the process may be carried out in either a batchwise or a continuous system.
- the production system may be closed to provide complete recycle ofthe unreacted feed material haloalkane and haloalkene.
- the feed material, a haloalkane and a haloalkene are reacted in the presence of a catalyst and cocatalyst.
- a catalyst and cocatalyst The specific haloalkane and haloalkene used as feed material, as well as the catalyst, cocatalyst, and reaction conditions used will depend on the desired product. Suitable feed material is commercially available.
- Exemplary haloalkanes include, without limitation, carbon tetrachloride, 1,1, 1- trichloroethane, dichlorofluoromethane, 1, 1, 1 -trichlorotrifluoroethane, 1,1,2- trichlorotrifluoroethane, tetrachloroethane, pentachloroethane, and hexachloroethane.
- haloalkenes include, without limitation, vinyl chloride, 1,1- dichloroethene, trichloroethene, tetrachloroethene, chlorofluoroethene, 1,2- dichloroethene, 1,1-dichloro-difluoroethene, 1 -chloro- 1 -propene, and 1 -chloro- 1- butene.
- the preferred feed materials are carbon tetrachloride, available from Vulcan Chemicals, Birmingham, Alabama and vinyl chloride, available from PPG Industries, Pittsburgh, Pennsylvania.
- the mole ratio of haloalkane to haloalkene is from about 0.02 . 1 to about 50 : 1.
- the ratio is from about 1.2 : 1 to about 4.0 1 and more preferably from about 1.5 : 1 to about 2.5 : 1 haloalkane to haloalkene.
- the catalysts useful in the present invention include metal ions. Suitable catalysts include cuprous salts, organometallic cuprous compounds, iron powder, and iron chloride. Exemplary cuprous salts and organometallic cuprous compounds include, without limitation, cuprous chloride, cuprous bromide, cuprous cyanide, cuprous sulfate, and cuprous phenyl.
- the iron powder used in this invention is a fine powder of pure metallic iron, preferably with a particle size smaller than 325 mesh. Preferably, cuprous chloride or iron powder is used.
- the ccatalyst ofthe present invention is an organic ligand capable of forming a complex with the catalyst used and bringing the catalyst into solution.
- Suitable ligands include organic amines, such as, without limitation, tert- butylamine, n-butylamine, sec-butylamine, 2-propylamine, benzylamine, tri-n- butylamine, and pyridine.
- the preferred organic amine is tert-butylamine.
- the cocatalyst may be a nitrile including, without limitation, acetonitrile, propionitrile, n-butyronitrile, benzonitrile, and phenylacetonitrile.
- the preferred nitrile is acetonitrile.
- the cocatalyst may be an amide including, without limitation, hexamethylphosphoramide and dimethylformamide. Hexamethylphosphoramide is the preferred amide.
- the catalysts and cocatalysts useful in the present invention are commercially available.
- the catalyst-cocatalyst system is cuprous chloride - tert-butylamine or iron powder-hexamethylphosphoramide. Most preferably, iron powder-hexamethylphosphoramide is used.
- the catalyst and cocatalyst are used in amounts sufficient to catalyze the reaction ofthe feed material. Generally, the amount used is a mole ratio of catalyst to cocatalyst from about 0.01 : 1 to about 50 : 1, preferably from about 0 1 : 1 to about 3 : 1.
- the mole ratio of copper to t-butylamine is about 0.05 : 1 to about 2.0 : 1, preferably about 0.02 : 1 to 1.0 : 1, and more preferably about 0.1 : 1 to about 0.7 : 1.
- the mole ratio of iron powder to hexamethylphosphoramide may be about 0.05 : 1 to about 10.0 : 1, preferably about 1.0 : 1 to about 3.0 : 1, and more preferably about 1.5 : 1 to about 2.5 : 1.
- the preferred concentration ofthe catalyst in the reaction mixture is from about 0.01 to about 10 weight percent, preferably from about 1 to about 5 weight percent, and more preferably from about 1.5 to about 2.5 weight percent.
- the catalyst may be added to the reactor containing the haloalkane, haloalkene, and cocatalyst.
- the haloalkane and haloalkene may be added to a reactor containing the catalyst and cocatalyst.
- the catalyst, cocatalyst and haloalkane are mixed first, the mixture degassed by quick partial evacuation ofthe vapors, with or without cooling ofthe mixture, and the haloalkene is added to the mixture.
- the reactor is heated to a temperature of from about 40° C to about 180° C, preferably from about 85° C to about 110° C, with agitation and under the vapor pressure ofthe reagents.
- the reaction is carried out until a conversion higher than 95% is achieved, generally for a period of from about 6 hours to about 24 hours, preferably from about 6 hours to about 12 hours.
- the reactor pressure may fall.
- the temperature may be increased an additional 10° to 60° to improve conversion.
- the product stream from step (A) is flash-distilled to remove unreacted haloalkane and haloalkene feed materials and cocatalyst.
- the distillation may be performed in one or more distillation columns which are well known in the art.
- the flash distillation is conducted in two steps: first, flash distillation is conducted under atmospheric pressure at about 85° C followed by vacuum flash distillation to remove unreacted haloalkane, haloalkene, and cocatalyst.
- the vacuum flash distillation should be carried out until the pressure falls to 50 mm Hg at 80° C
- the distilled, unreacted haloalkane, haloalkene, and cocatalyst may be recycled back to the reactor.
- the "bottoms" stream, containing crude product and catalyst, from the flash distillation step (B) are filtered by any commonly known filter, preferably using vacuum or an inert gas pressure, such as nitrogen, to push the liquid through the filter.
- the catalyst may be recycled back to the reactor
- step (D) ofthe process ofthe present invention provides for the purification ofthe crude product by distillation. Fractional vacuum distillation is carried out at about 5 to about 50 mm Hg and a temperature of about 89° C to about 1 10° C to recover the product. It has been discovered that, when step (D) is carried out in the presence of a trialkyl phosphate such as tributyl phosphate or other metal chelating compound, the distillation yield of purified product is significantly improved. Although not seeking to be bound by any particular theory, it is believed that the tributyl phosphate acts to prevent the decomposition ofthe product haloalkane. Thus, in a preferred embodiment, step (D) includes the addition of an amount of a metal chelating compound sufficient to improve the haloalkane product yield. Preferably, 5 weight percent of tributyl phosphate is used.
- Example 2a Vacuum distillation as in Example 2a is continued with a two-stage oil vacuum pump. The material remaining in the distillation flask is distilled at 0.2 mm Hg and 84° C. 1.28 g pure heptachlorohexane is distilled. Four isomers, 1,2,2,4,4,5,5-heptachlorohexane, 1,1,1,3,3,5,5-heptachlorohexane, 1,2,2,3,3,5,5- heptachlorohexane and 1,1,1, 4,4,5, 5-heptachlorohexane are seen.
- Example 5 The solid -containing solution remaining in the distillation flask of Example 4 was removed to a Buchner funnel and filtered with No.1 Whatman filter paper The filtration was conducted using 60 mm Hg vacuum in an open system. The mother liquor consisted mainly of HCC-240. ICAP analysis indicated that it contained only 168 ppm copper catalyst.
- Examples 6 and Comparative Example 6 illustrate that the use of a metal chelating compound provides improved distillation yields and prevents the decomposition of product and tar formation.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50929897A JP3369187B2 (en) | 1995-08-14 | 1996-07-26 | Method for producing halogenated alkanes |
EP96925539A EP0850210B1 (en) | 1995-08-14 | 1996-07-26 | Process for the preparation of halogenated alkanes |
MX9800983A MX9800983A (en) | 1995-08-14 | 1996-07-26 | Process for the preparation of halogenated alkanes. |
AT96925539T ATE196457T1 (en) | 1995-08-14 | 1996-07-26 | METHOD FOR PRODUCING HALOGENATED ALKANES |
CA002229200A CA2229200C (en) | 1995-08-14 | 1996-07-26 | Process for the preparation of halogenated alkanes |
DE69610433T DE69610433T2 (en) | 1995-08-14 | 1996-07-26 | METHOD FOR PRODUCING HALOGENATED ALKANS |
AU66024/96A AU6602496A (en) | 1995-08-14 | 1996-07-26 | Process for the preparation of halogenated alkanes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/514,545 | 1995-08-14 | ||
US08/514,545 US5902914A (en) | 1995-08-14 | 1995-08-14 | Process for the preparation of halogenated alkanes |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997007083A1 true WO1997007083A1 (en) | 1997-02-27 |
Family
ID=24047660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/012341 WO1997007083A1 (en) | 1995-08-14 | 1996-07-26 | Process for the preparation of halogenated alkanes |
Country Status (13)
Country | Link |
---|---|
US (1) | US5902914A (en) |
EP (1) | EP0850210B1 (en) |
JP (1) | JP3369187B2 (en) |
KR (1) | KR100512292B1 (en) |
CN (1) | CN1199387A (en) |
AT (1) | ATE196457T1 (en) |
AU (1) | AU6602496A (en) |
CA (1) | CA2229200C (en) |
DE (1) | DE69610433T2 (en) |
ES (1) | ES2150686T3 (en) |
MX (1) | MX9800983A (en) |
TW (1) | TW363049B (en) |
WO (1) | WO1997007083A1 (en) |
Cited By (19)
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WO1998050329A1 (en) * | 1997-05-05 | 1998-11-12 | Solvay (Societe Anonyme) | Method for preparing 1,1,1,3,3-pentachlorobutane |
WO1998050330A1 (en) * | 1997-05-05 | 1998-11-12 | Solvay (Societe Anonyme) | Method for preparing halogenated hydrocarbons |
EP0889017A1 (en) * | 1997-07-03 | 1999-01-07 | SOLVAY (Société Anonyme) | Pentachlorobutane, process for its preparation and use, process for the preparation of 1,1-difluoro-2-trifluoromethylpropane and use of this compound |
WO1999007659A1 (en) * | 1997-08-08 | 1999-02-18 | Solvay (Societe Anonyme) | Method for preparing halogenated hydrocarbons |
BE1011142A3 (en) * | 1997-05-05 | 1999-05-04 | Solvay | 1,1,1,3,3-pentachlorobutane preparation method |
BE1011319A3 (en) * | 1997-05-05 | 1999-07-06 | Solvay | Method for preparing halogenated hydrocarbons. |
WO2000017137A1 (en) * | 1998-09-18 | 2000-03-30 | Asahi Glass Company Ltd. | Process for producing 1,1,1,3,3-pentachloropropane |
EP0999196A1 (en) * | 1998-11-05 | 2000-05-10 | SOLVAY (Société Anonyme) | Process for the preparation of halogenated hydrocarbons |
WO2000068172A1 (en) * | 1999-05-12 | 2000-11-16 | Alliedsignal Inc. | Continuous process for preparing halogenated compounds |
WO2001025175A1 (en) * | 1999-10-06 | 2001-04-12 | Solvay (Societe Anonyme) | Method for obtaining halogenated hydrocarbons in the presence of a co-catalyst |
US6369285B1 (en) | 1999-10-06 | 2002-04-09 | Solvay (Societe Anonyme) | Process for preparing halohydrocarbons |
WO2002102750A2 (en) * | 2001-06-14 | 2002-12-27 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3-pentachloropropane |
WO2008040803A1 (en) | 2006-10-06 | 2008-04-10 | Solvay (Société Anonyme) | Process for the preparation of halogenated hydrocarbons with at least 3 carbon atoms in the presence of iron and a phosphite |
EP2020236A1 (en) | 1999-10-25 | 2009-02-04 | Laboratoire Theramex | Contraceptive medicament based on a progestative and oestrogen, method for producing the same, and use |
WO2012067870A1 (en) * | 2010-11-17 | 2012-05-24 | E. I. Du Pont De Nemours And Company | Process for making hydrohalocarbons and selected compounds |
US20120172636A1 (en) * | 2011-01-04 | 2012-07-05 | Honeywell International Inc. | High purity e-1-chloro-3,3,3-trifluoropropene and methods of making the same |
WO2014127001A3 (en) * | 2013-02-12 | 2014-10-09 | Occidental Chemical Corporation | Methods for recovering chlorinated hydrocarbons |
EP2714632A4 (en) * | 2011-06-03 | 2015-02-18 | Honeywell Int Inc | Method for avoiding the generation of by-products during the production of haloalkane compounds |
US9738577B2 (en) | 2006-10-11 | 2017-08-22 | Honeywell International Inc. | Process for the manufacture of 1,1,1,3,3-pentachloropropane |
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US6688118B1 (en) * | 1996-03-01 | 2004-02-10 | E. I. Du Pont De Nemours And Company | Azeotropic compositions of cyclopentane |
US6518467B2 (en) | 2000-12-29 | 2003-02-11 | Honeywell International Inc. | Method of making hydrofluorocarbons and hydrochlorofluorocarbons |
US6534688B2 (en) | 2001-06-11 | 2003-03-18 | Vulcan Chemicals | Dehydrochlorination stabilization of polychlorinated alkanes |
US20050177012A1 (en) * | 2001-07-20 | 2005-08-11 | Pcbu Services, Inc. | Halocarbon production processes, halocarbon separation processes, and halocarbon separation systems |
US20030028057A1 (en) * | 2001-07-20 | 2003-02-06 | Stephen Owens | Methods and materials for the preparation and purification of halogenated hydrocarbons |
US7094936B1 (en) * | 2001-07-20 | 2006-08-22 | Great Lakes Chemical Corporation | Process for preparing halogenated alkanes |
US6720466B2 (en) | 2002-04-17 | 2004-04-13 | Vulcan Chemicals, a division of Vulcan Materials Company | 1,1,1,3,3-pentachloropropane process purge stream concentration using a secondary refluxed evaporator and secondary product recovery |
US7102041B2 (en) * | 2004-12-08 | 2006-09-05 | Honeywell International Inc. | Continuous process for preparing halogenated compounds |
US20070106099A1 (en) * | 2005-11-10 | 2007-05-10 | Pcbu Services, Inc. | Production processes and systems |
CN100406417C (en) * | 2006-11-17 | 2008-07-30 | 浙江蓝天环保高科技股份有限公司 | Method for preparing 1,1,1,3,3 - pentachlorobutane from materials of chloropropene and carbon tetrachloride under tempering and polymerizing catalyst |
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US10112166B2 (en) * | 2011-06-03 | 2018-10-30 | Honeywell International Inc. | Method for capturing and recycling iron catalyst used in the production of haloalkane compounds |
US8835702B2 (en) | 2011-06-03 | 2014-09-16 | Honeywell International Inc. | Method for mitigating the formation of by-products during the production of haloalkane compounds |
US9289758B2 (en) | 2013-01-22 | 2016-03-22 | Axiall Ohio, Inc. | Processes for producing chlorinated hydrocarbons and methods for recovering polyvalent antimony catalysts therefrom |
US8889930B2 (en) | 2013-01-22 | 2014-11-18 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons |
US9090531B2 (en) * | 2013-03-14 | 2015-07-28 | Honeywell International Inc. | Method for mitigating HCL generation during 1,1,2,3-tetrachloropropene purification |
US9139497B2 (en) | 2013-10-23 | 2015-09-22 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound |
JP6173908B2 (en) * | 2013-12-27 | 2017-08-02 | 株式会社トクヤマ | Method for producing chloro higher alkene |
ES2882035T3 (en) * | 2014-10-16 | 2021-12-01 | Spolek Pro Chemickou A Hutni Vyrobu As | Process |
US9896400B2 (en) | 2014-10-16 | 2018-02-20 | Spolek Pro Chemickou A Hutni Vyrobu A.S. | Process for producing a chlorinated C3-6 alkane |
US10793496B2 (en) | 2016-04-13 | 2020-10-06 | Spolek Pro Chemickou A Hutni Vyrobu A.S. | Process for producing a chlorinated alkane |
US11192841B2 (en) * | 2018-04-03 | 2021-12-07 | Blue Cube Ip Llc | Processes for preparing halogenated alkanes |
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JPH07103052B2 (en) * | 1987-09-01 | 1995-11-08 | 三井東圧化学株式会社 | Distillation purification method of neophyll halides |
-
1995
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-
1996
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- 1996-07-26 JP JP50929897A patent/JP3369187B2/en not_active Expired - Lifetime
- 1996-07-26 MX MX9800983A patent/MX9800983A/en unknown
- 1996-07-26 AU AU66024/96A patent/AU6602496A/en not_active Abandoned
- 1996-07-26 ES ES96925539T patent/ES2150686T3/en not_active Expired - Lifetime
- 1996-07-26 WO PCT/US1996/012341 patent/WO1997007083A1/en active IP Right Grant
- 1996-07-26 KR KR10-1998-0701089A patent/KR100512292B1/en not_active IP Right Cessation
- 1996-07-26 AT AT96925539T patent/ATE196457T1/en not_active IP Right Cessation
- 1996-07-26 EP EP96925539A patent/EP0850210B1/en not_active Expired - Lifetime
- 1996-07-26 DE DE69610433T patent/DE69610433T2/en not_active Expired - Lifetime
- 1996-07-26 CA CA002229200A patent/CA2229200C/en not_active Expired - Lifetime
- 1996-07-26 CN CN96197591A patent/CN1199387A/en active Pending
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US6399839B1 (en) | 1997-05-05 | 2002-06-04 | Solvay (Societe Anonyme) | Method for preparing halogenated hydrocarbons |
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WO2002102750A2 (en) * | 2001-06-14 | 2002-12-27 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3-pentachloropropane |
US6500995B1 (en) | 2001-06-14 | 2002-12-31 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3,-pentachloropropane |
WO2008040803A1 (en) | 2006-10-06 | 2008-04-10 | Solvay (Société Anonyme) | Process for the preparation of halogenated hydrocarbons with at least 3 carbon atoms in the presence of iron and a phosphite |
US7947856B2 (en) | 2006-10-06 | 2011-05-24 | Solvay (Societe Anonyme) | Process for the preparation of halogenated hydrocarbons with at least 3 carbon atoms in the presence of iron and a phosphite |
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Also Published As
Publication number | Publication date |
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ES2150686T3 (en) | 2000-12-01 |
DE69610433D1 (en) | 2000-10-26 |
US5902914A (en) | 1999-05-11 |
TW363049B (en) | 1999-07-01 |
KR19990036420A (en) | 1999-05-25 |
CA2229200A1 (en) | 1997-02-27 |
JPH11511164A (en) | 1999-09-28 |
EP0850210A1 (en) | 1998-07-01 |
CA2229200C (en) | 2008-02-26 |
MX9800983A (en) | 1998-04-30 |
EP0850210B1 (en) | 2000-09-20 |
AU6602496A (en) | 1997-03-12 |
JP3369187B2 (en) | 2003-01-20 |
DE69610433T2 (en) | 2001-01-18 |
CN1199387A (en) | 1998-11-18 |
ATE196457T1 (en) | 2000-10-15 |
KR100512292B1 (en) | 2005-11-24 |
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