DE60019649T2 - Verfahren zur herstellung von 1,1,1,3,3-pentachlorpropan - Google Patents
Verfahren zur herstellung von 1,1,1,3,3-pentachlorpropan Download PDFInfo
- Publication number
- DE60019649T2 DE60019649T2 DE60019649T DE60019649T DE60019649T2 DE 60019649 T2 DE60019649 T2 DE 60019649T2 DE 60019649 T DE60019649 T DE 60019649T DE 60019649 T DE60019649 T DE 60019649T DE 60019649 T2 DE60019649 T2 DE 60019649T2
- Authority
- DE
- Germany
- Prior art keywords
- pentachloropropane
- reactor
- vinyl chloride
- distillation
- iron
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 61
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 40
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 26
- 239000000047 product Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000006227 byproduct Substances 0.000 claims abstract description 18
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims description 28
- 229910052742 iron Inorganic materials 0.000 claims description 23
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 19
- 238000004821 distillation Methods 0.000 claims description 14
- 238000004062 sedimentation Methods 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 7
- 238000010926 purge Methods 0.000 claims description 7
- 239000011362 coarse particle Substances 0.000 claims description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000012263 liquid product Substances 0.000 claims description 2
- 229910001510 metal chloride Inorganic materials 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 abstract description 4
- 230000008020 evaporation Effects 0.000 abstract description 4
- 238000004064 recycling Methods 0.000 abstract description 3
- 229950005499 carbon tetrachloride Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000011084 recovery Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- XPIGFCKQOOBTLK-UHFFFAOYSA-N 1,1,3,3-tetrachloroprop-1-ene Chemical compound ClC(Cl)C=C(Cl)Cl XPIGFCKQOOBTLK-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 238000007033 dehydrochlorination reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- ZVQNCOZXOFKLAO-UHFFFAOYSA-N 1,1,1,5,5,5-hexachloropentane Chemical class ClC(Cl)(Cl)CCCC(Cl)(Cl)Cl ZVQNCOZXOFKLAO-UHFFFAOYSA-N 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229960002089 ferrous chloride Drugs 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- -1 haloalkane compound Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 3
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- JYBUJRUDSJVLBU-UHFFFAOYSA-N 1,1,1,2,2,3-hexachloropentane Chemical compound CCC(Cl)C(Cl)(Cl)C(Cl)(Cl)Cl JYBUJRUDSJVLBU-UHFFFAOYSA-N 0.000 description 2
- NPGZAFRXWIXMGZ-UHFFFAOYSA-N 1,1,1,3,3-pentachloropentane Chemical compound CCC(Cl)(Cl)CC(Cl)(Cl)Cl NPGZAFRXWIXMGZ-UHFFFAOYSA-N 0.000 description 2
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006284 Kharasch reaction Methods 0.000 description 2
- 229910000990 Ni alloy Inorganic materials 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 239000012256 powdered iron Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- POBGQHDEFZRTOP-UHFFFAOYSA-N 1,1,1,2,3-pentachloropentane Chemical compound CCC(Cl)C(Cl)C(Cl)(Cl)Cl POBGQHDEFZRTOP-UHFFFAOYSA-N 0.000 description 1
- MTBZFCJQMJGQRT-UHFFFAOYSA-N 1,1,1,3,5,5-hexachloropentane Chemical compound ClC(Cl)CC(Cl)CC(Cl)(Cl)Cl MTBZFCJQMJGQRT-UHFFFAOYSA-N 0.000 description 1
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 description 1
- MZKBMNSSGVXEMV-UHFFFAOYSA-N 1,1,3,3,5,5-hexachloropentane Chemical compound ClC(Cl)CC(Cl)(Cl)CC(Cl)Cl MZKBMNSSGVXEMV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US671993 | 1996-06-28 | ||
| US09/671,993 US6313360B1 (en) | 2000-09-29 | 2000-09-29 | Process for the manufacture of 1, 1, 1, 3, 3-pentachloropropane |
| PCT/US2000/032454 WO2002028806A1 (en) | 2000-09-29 | 2000-12-13 | Process for the manufacture of 1,1,1,3,3-pentachloropropane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60019649D1 DE60019649D1 (de) | 2005-05-25 |
| DE60019649T2 true DE60019649T2 (de) | 2006-01-19 |
Family
ID=24696710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60019649T Expired - Lifetime DE60019649T2 (de) | 2000-09-29 | 2000-12-13 | Verfahren zur herstellung von 1,1,1,3,3-pentachlorpropan |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6313360B1 (enExample) |
| EP (1) | EP1328496B1 (enExample) |
| JP (1) | JP2004524272A (enExample) |
| AT (1) | ATE293586T1 (enExample) |
| DE (1) | DE60019649T2 (enExample) |
| ES (1) | ES2237488T3 (enExample) |
| MX (1) | MXPA03002713A (enExample) |
| WO (1) | WO2002028806A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6500995B1 (en) * | 2001-06-14 | 2002-12-31 | Vulcan Chemicals | Water-enhanced production of 1,1,1,3,3,-pentachloropropane |
| US20050177012A1 (en) * | 2001-07-20 | 2005-08-11 | Pcbu Services, Inc. | Halocarbon production processes, halocarbon separation processes, and halocarbon separation systems |
| US7094936B1 (en) * | 2001-07-20 | 2006-08-22 | Great Lakes Chemical Corporation | Process for preparing halogenated alkanes |
| US20030028057A1 (en) * | 2001-07-20 | 2003-02-06 | Stephen Owens | Methods and materials for the preparation and purification of halogenated hydrocarbons |
| US6552238B1 (en) * | 2001-08-31 | 2003-04-22 | Vulcan Chemicals | Separation of heavy ends from streams of 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 |
| US20040225166A1 (en) * | 2003-05-05 | 2004-11-11 | Vulcan Chemicals A Business Group Of Vulcan Materials Company | Method for producing 1,1,1,3-tetrachloropropane and other haloalkanes with iron catalyst |
| US7112709B2 (en) * | 2003-09-09 | 2006-09-26 | Vulcan Chemicals | Method for reusing heavy end by-products in the manufacture of polychlorinated alkanes |
| US7265082B2 (en) * | 2004-08-04 | 2007-09-04 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,1,3,3-pentachloropropane and carbon tetrachloride |
| US20070106099A1 (en) * | 2005-11-10 | 2007-05-10 | Pcbu Services, Inc. | Production processes and systems |
| CN100427442C (zh) * | 2005-12-19 | 2008-10-22 | 浙江蓝天环保高科技股份有限公司 | 1,1,1,3,3-五氯丙烷的改进制备方法 |
| EP1908744A1 (en) * | 2006-10-06 | 2008-04-09 | SOLVAY (Société Anonyme) | Process for the preparation of halogenated hydrocarbons with at least 3 carbon atoms in the presence of Iron and a phosphite |
| US9738577B2 (en) * | 2006-10-11 | 2017-08-22 | Honeywell International Inc. | Process for the manufacture of 1,1,1,3,3-pentachloropropane |
| CA2708643C (en) | 2007-12-19 | 2017-05-30 | Occidental Chemical Corporation | Methods of making chlorinated hydrocarbons |
| JP2011057650A (ja) * | 2009-09-14 | 2011-03-24 | Tokuyama Corp | クロロプロペンの製造方法 |
| CN101913980A (zh) * | 2010-09-07 | 2010-12-15 | 西安近代化学研究所 | 1，1，1，3，3-五氯丙烷的生产方法 |
| KR20130122617A (ko) * | 2010-10-22 | 2013-11-07 | 가부시끼가이샤 도꾸야마 | 폴리클로로프로판을 제조하기 위한 연속 배치 반응 방법 |
| JP5642495B2 (ja) * | 2010-10-22 | 2014-12-17 | 株式会社トクヤマ | ポリクロロプロパンを製造するための連続バッチ反応方法 |
| JP5783707B2 (ja) * | 2010-11-15 | 2015-09-24 | 株式会社トクヤマ | ポリクロロプロパンを製造するための連続バッチ反応方法 |
| US9156752B2 (en) | 2011-01-04 | 2015-10-13 | Honeywell International Inc. | High purity E-1-chloro-3,3,3-trifluoropropene and methods of making the same |
| US8722946B2 (en) * | 2011-06-03 | 2014-05-13 | Honeywell International Inc. | Method for avoiding the generation of by-products during 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 |
| 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 |
| EP3808723A1 (en) | 2011-10-14 | 2021-04-21 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| CN103373894B (zh) * | 2012-04-13 | 2015-03-18 | 中化蓝天集团有限公司 | 一种制备c3饱和卤代烷烃的连续方法 |
| JP6158032B2 (ja) * | 2012-10-17 | 2017-07-05 | 株式会社トクヤマ | 反応ガスをリサイクルした塩素化プロパンの製造方法 |
| US8889930B2 (en) | 2013-01-22 | 2014-11-18 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons |
| US9289758B2 (en) | 2013-01-22 | 2016-03-22 | Axiall Ohio, Inc. | Processes for producing chlorinated hydrocarbons and methods for recovering polyvalent antimony catalysts therefrom |
| US9067858B2 (en) * | 2013-02-12 | 2015-06-30 | Occidental Chemical Corporation | Methods for recovering 1,1,1,2,3-pentachloropropane |
| US9139497B2 (en) | 2013-10-23 | 2015-09-22 | Axiall Ohio, Inc. | Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound |
| EP3142993B2 (en) | 2014-05-16 | 2022-01-12 | Occidental Chemical Corporation | Method for making 1,1,3,3-tetrachloropropene |
| FR3027304B1 (fr) * | 2014-10-16 | 2018-02-23 | Arkema France | Compositions a base de 1,1,1,3,3-pentachloropropane |
| US9896400B2 (en) | 2014-10-16 | 2018-02-20 | Spolek Pro Chemickou A Hutni Vyrobu A.S. | Process for producing a chlorinated C3-6 alkane |
| CN104496745B (zh) * | 2014-11-28 | 2018-05-04 | 巨化集团技术中心 | 一种合成氯代烃的制备方法 |
| CN104513127B (zh) * | 2014-11-28 | 2018-08-03 | 巨化集团技术中心 | 一种1,1,1,3,3-五氯丙烷的制备方法 |
| CN105418360B (zh) * | 2015-11-11 | 2017-09-08 | 西安近代化学研究所 | 一种制备1,1,1,3,3‑五氯丁烷的方法 |
| WO2017120264A1 (en) | 2016-01-04 | 2017-07-13 | Blue Cube Ip Llc | Improved processes for preparing halogenated alkanes |
| CN105859512B (zh) * | 2016-04-19 | 2019-01-22 | 浙江衢州巨新氟化工有限公司 | 一种1,1,1,3,3-五氯丙烷的制备方法 |
| US10787405B2 (en) | 2016-07-05 | 2020-09-29 | Occidental Chemical Corporation | Photochlorination of chloroform to carbon tetrachloride |
| PT3795554T (pt) | 2016-07-26 | 2024-10-29 | Occidental Chem Co | Método para produzir propanos halogenados |
| CN108033872B (zh) * | 2017-12-05 | 2021-07-09 | 安庆市华璞环保材料科技有限责任公司 | 一种清洁环保生产1,1’,2,3-四氯丙烯的方法及其设备 |
| WO2019195248A1 (en) | 2018-04-03 | 2019-10-10 | Blue Cube Ip Llc | Method for recycling catalyst in the production of chlorinated alkanes |
| CN111902385A (zh) * | 2018-04-03 | 2020-11-06 | 蓝立方知识产权有限责任公司 | 改进的制备卤化烷烃的方法 |
| CN113329986A (zh) | 2019-01-10 | 2021-08-31 | 西方化学股份有限公司 | 部分氯化的氯代甲烷光氯化成四氯化碳 |
| WO2025096368A2 (en) | 2023-10-30 | 2025-05-08 | The Chemours Company Fc, Llc | Compositions comprising 1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof |
| WO2025096370A2 (en) | 2023-10-30 | 2025-05-08 | The Chemours Company Fc, Llc | Compositions comprising 1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE22877T1 (de) * | 1983-07-06 | 1986-11-15 | Monsanto Co | Verfahren zur herstellung von monoaddukten von olefinen und damit reagierfaehigen telogenen. |
| EP0729932A1 (en) * | 1995-03-03 | 1996-09-04 | Central Glass Company, Limited | Method of producing halopropane |
| JP2000086545A (ja) * | 1998-09-18 | 2000-03-28 | Asahi Glass Co Ltd | １，１，１，３，３−ペンタクロロプロパンの製造方法 |
| BE1012268A3 (fr) * | 1998-11-05 | 2000-08-01 | Solvay | Procede de preparation d'hydrocarbures halogenes. |
| US6187978B1 (en) * | 1999-05-12 | 2001-02-13 | Alliedsignal Inc. | Continuous process for manufacturing halogenated compounds |
-
2000
- 2000-09-29 US US09/671,993 patent/US6313360B1/en not_active Expired - Lifetime
- 2000-12-13 JP JP2002532195A patent/JP2004524272A/ja active Pending
- 2000-12-13 MX MXPA03002713A patent/MXPA03002713A/es active IP Right Grant
- 2000-12-13 DE DE60019649T patent/DE60019649T2/de not_active Expired - Lifetime
- 2000-12-13 ES ES00989209T patent/ES2237488T3/es not_active Expired - Lifetime
- 2000-12-13 EP EP00989209A patent/EP1328496B1/en not_active Expired - Lifetime
- 2000-12-13 WO PCT/US2000/032454 patent/WO2002028806A1/en not_active Ceased
- 2000-12-13 AT AT00989209T patent/ATE293586T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004524272A (ja) | 2004-08-12 |
| MXPA03002713A (es) | 2005-07-25 |
| EP1328496B1 (en) | 2005-04-20 |
| EP1328496A1 (en) | 2003-07-23 |
| ES2237488T3 (es) | 2005-08-01 |
| ATE293586T1 (de) | 2005-05-15 |
| US6313360B1 (en) | 2001-11-06 |
| WO2002028806A1 (en) | 2002-04-11 |
| DE60019649D1 (de) | 2005-05-25 |
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| 8327 | Change in the person/name/address of the patent owner |
Owner name: BASIC CHEMICALS COMPANY, LLC, DALLAS, TEX., US |
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| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: OCCIDENTAL CHEMICAL CORP. (N.D.GES.D. STAATES , US |