ES2554979T3 - Proceso para la preparación de fluoroalquenos C3-7 por deshidrohalogenación mediada por base de fluoroalcanos C3-7 hidrohalogenados - Google Patents
Proceso para la preparación de fluoroalquenos C3-7 por deshidrohalogenación mediada por base de fluoroalcanos C3-7 hidrohalogenados Download PDFInfo
- Publication number
- ES2554979T3 ES2554979T3 ES07848577.8T ES07848577T ES2554979T3 ES 2554979 T3 ES2554979 T3 ES 2554979T3 ES 07848577 T ES07848577 T ES 07848577T ES 2554979 T3 ES2554979 T3 ES 2554979T3
- Authority
- ES
- Spain
- Prior art keywords
- fluoroalkenes
- hydrohalogenated
- fluoroalkanes
- dehydrohalogenation
- mediated
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 title 1
- 230000001404 mediated effect Effects 0.000 title 1
- 239000002904 solvent Substances 0.000 abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 abstract description 4
- 239000002585 base Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SUAMPXQALWYDBK-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluoropropane Chemical compound FCC(F)(F)C(F)(F)F SUAMPXQALWYDBK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 description 1
- SMZHKGXSEAGRTI-UHFFFAOYSA-N 1,1,1-trichloropropan-2-one Chemical compound CC(=O)C(Cl)(Cl)Cl SMZHKGXSEAGRTI-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- 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
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
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)
- Catalysts (AREA)
Abstract
Un proceso de preparación de un compuesto de fórmula CF3CF>=CHX, en donde X es H o F, proceso que comprende deshidrohalogenar un compuesto de fórmula CF3CFYCH2X o CF3CFHCYHX, en donde Y es F, Cl, Br o I, en presencia de una base seleccionada de un hidróxido de metal alcalino y un hidróxido de metal alcalinotérreo, llevándose a cabo el proceso en un disolvente que comprende N-metilpirrolidona.
Description
acetona. En una vía de síntesis tal, la acetona puede clorarse (por ejemplo, usando cloro sobre un catalizador de cromia) para producir 1,1,1-tricloroacetona, que puede clorarse adicionalmente (por ejemplo, usando PCl5 -véase Advanced Organic Chemistry (Ed M B Smith y J March), Quinta Edición, página 1195) para producir 1,1,1,2,2pentacloropropano, como se ilustra a continuación.
Puede prepararse HFC-1225ye deshidrohalogenando un compuesto de fórmula CF3CFYCH2F o CF3CFHCYFH, en las que Y es F, Cl, Br o I, preferentemente F o Cl, lo más preferentemente F. Así, HFC-1225ye se prepara 10 actualmente lo más preferentemente por la deshidrofluoración de CF3CFHCF2H (HFC-236ea) o CF3CF2CH2F (HFC236cb), como se ilustra a continuación.
15 HFC-1225ye existe como dos isómeros geométricos, como se ilustra a continuación.
Tanto HFC-236ea como HFC-236cb pueden obtenerse de Apollo Chemicals Ltd. Alternativamente, HFC-236ea, por 20 ejemplo, puede prepararse convenientemente hidrogenando hexafluoropropileno del siguiente modo.
CF3CF=CF2 + H2 → CF3CHFCHF2
Los (hidro)fluoroalquenos que pueden prepararse por la presente invención tienen numerosas utilidades, por 25 ejemplo, como refrigerantes, monómeros, materias primas y disolventes.
La invención se ilustrará ahora, pero no se limita, por los siguientes ejemplos. La invención se define por las reivindicaciones que siguen a los ejemplos.
Ejemplos comparativos 1-7
Se cargaron disolvente (10 g), hidróxido de metal alcalino (10 g) y (si se usa) catalizador (0,25 g) a un recipiente de
35 Hastalloy C de 50 ml equipado con indicadores de temperatura y de presión y un agitador cruciforme. El recipiente se selló y la presión se probó con nitrógeno. Entonces se cargó una alimentación de o bien CF3CFHCF2H (HFC236ea) o bien CF3CF2CH2F (HFC-236cb) (10-15 g, 97 %) desde una pequeña bomba de alimentación y el contenido se calentó a 150 ºC durante los tiempos especificados en la Tabla 1 con agitación. Al final del experimento, los productos volátiles y cualquier alimentación sin convertir se recuperaron mediante destilación para el análisis por
40 CG-EM. Los resultados se ilustran en la Tabla 1.
7
Tabla 1: 236ea/cb → 1225ye
- Expt Nº
- Isómero HFC236 Disolvente Base Catalizador Tiempo (h) Conversión (%) Z1225ye (%) E1225ye (%) 1225 zc (%)
- 1
- ea agua KOH - 3,5 57,8 46,7 5,7 0
- 2
- ea agua NaOH - 4,5 20,8 14,9 1,7 0
- 3
- ea agua KOH - 19 21,4 15,9 1,3 0
- 4
- ea agua KOH 18-corona-6 2,5 57,5 49,3 4,1 0
- 5
- ea PEG300 KOH - 3 50,4 41 2,8 0
- 6
- cb agua KOH - 19 1,3 0,52 0 N/A
- 7
- cb agua KOH - 22 1,5 0,42 0 N/A
5 Se cargaron base, disolvente y catalizador, si se usó, al recipiente de reacción. El recipiente de reacción se selló, se probó la presión y se evacuó. Entonces se transfirió una cantidad previamente pesada de la alimentación orgánica al reactor. El reactor y su contenido se pesaron entonces antes de calentarse de temperatura ambiente a 150 ºC durante 45 minutos con agitación. Esta temperatura se mantuvo con agitación a 1500 rpm durante 6 horas. Después de este periodo, el reactor y su contenido se enfriaron a 10 ºC durante 30 minutos y la tasa de agitación se redujo a
10 200 rpm.
Al día siguiente, el reactor y su contenido se volvieron a pesar y a continuación el reactor se volvió a calentar a 50 ºC listo para la recuperación de productos. Los productos y cualquier material de partida sin reaccionar se recuperaron mediante destilación en una bomba de muestra previamente pesada y enfriada (-78 ºC) evacuada. El peso de los
15 productos recuperados se determinó antes de analizarse por CG-EM. La CG-EM se calibró usando muestras de alimentación y de producto si estuvieron disponibles. Se cuantificaron los desconocidos usando factores de respuesta relativa promedio. Los resultados se presentan en las Tablas 2-4.
8
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0625214 | 2006-12-19 | ||
| GBGB0625214.2A GB0625214D0 (en) | 2006-12-19 | 2006-12-19 | Process |
| PCT/GB2007/004840 WO2008075017A2 (en) | 2006-12-19 | 2007-12-18 | Process for the preparation of c3-7 fluoroalkenes by base-mediated dehydrohalogenatation of hydrohalogenated c3 -7 fluoroalkanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2554979T3 true ES2554979T3 (es) | 2015-12-28 |
Family
ID=37712338
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES21165666T Active ES2963129T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de 2,3,3,3-tetrahidrofluoropropeno |
| ES07848577.8T Active ES2554979T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de fluoroalquenos C3-7 por deshidrohalogenación mediada por base de fluoroalcanos C3-7 hidrohalogenados |
| ES15186285T Active ES2874904T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de 2,3,3,3-tetrafluoropropeno |
| ES21165589T Active ES2964858T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de 2,3,3,3-tetrahidrofluoropropeno |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES21165666T Active ES2963129T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de 2,3,3,3-tetrahidrofluoropropeno |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15186285T Active ES2874904T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de 2,3,3,3-tetrafluoropropeno |
| ES21165589T Active ES2964858T3 (es) | 2006-12-19 | 2007-12-18 | Proceso para la preparación de 2,3,3,3-tetrahidrofluoropropeno |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US8410325B2 (es) |
| EP (5) | EP2121548B1 (es) |
| JP (3) | JP5391076B2 (es) |
| KR (3) | KR101450159B1 (es) |
| CN (2) | CN101563308A (es) |
| AU (1) | AU2007336066A1 (es) |
| BR (1) | BRPI0720532A2 (es) |
| CA (1) | CA2673585C (es) |
| DK (2) | DK3872058T3 (es) |
| ES (4) | ES2963129T3 (es) |
| GB (1) | GB0625214D0 (es) |
| MX (1) | MX2009006433A (es) |
| PL (1) | PL2121548T3 (es) |
| RU (2) | RU2466121C2 (es) |
| WO (1) | WO2008075017A2 (es) |
| ZA (1) | ZA200904246B (es) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3304248B2 (ja) | 1995-10-31 | 2002-07-22 | シャープ株式会社 | 液体燃料燃焼装置 |
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| ES3036520T3 (en) | 2006-01-03 | 2025-09-19 | Honeywell Int Inc | Method for producing fluorinated organic compounds |
| WO2008030439A2 (en) | 2006-09-05 | 2008-03-13 | E. I. Du Pont De Nemours And Company | Dehydrofluorination process to manufacture hydrofluoroolefins |
| JP5416587B2 (ja) | 2006-10-03 | 2014-02-12 | メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ | プロセス |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| TW200831446A (en) * | 2006-11-15 | 2008-08-01 | Du Pont | Processes for producing pentafluoropropenes and certain azeotropes comprising HF and certain halopropenes of the formula C3HCIF4 |
| GB0625214D0 (en) * | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| GB0706978D0 (en) | 2007-04-11 | 2007-05-16 | Ineos Fluor Holdings Ltd | Process |
| US9035111B2 (en) | 2007-08-22 | 2015-05-19 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8710282B2 (en) | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| GB0806419D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| GB0806389D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| KR102663488B1 (ko) * | 2008-05-07 | 2024-05-10 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 2,3-다이클로로-1,1,1-트라이플루오로프로판, 2-클로로-1,1,1-트라이플루오로프로펜, 2-클로로-1,1,1,2-테트라플루오로프로판 또는 2,3,3,3-테트라플루오로프로펜을 포함하는 조성물 |
| GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| FR2933691B1 (fr) * | 2008-07-10 | 2012-11-09 | Arkema France | Hydro(chloro)fluoroolefines et leur procede de preparation |
| CN102131754B (zh) | 2008-08-26 | 2015-02-25 | 大金工业株式会社 | 共沸或类共沸组合物和制备2,3,3,3-四氟丙烯的方法 |
| FR2935700B1 (fr) * | 2008-09-11 | 2013-05-10 | Arkema France | Procede de preparation de composes trifluores et tetrafluores |
| FR2935703B1 (fr) * | 2008-09-11 | 2010-09-03 | Arkema France | Procede de preparation de composes fluores. |
| FR2935701B1 (fr) | 2008-09-11 | 2012-07-27 | Arkema France | Procede de preparation de composes fluores olefiniques |
| MX2011003633A (es) * | 2008-10-10 | 2011-05-02 | Du Pont | Composiciones que comprenden 2,3,3,3-tetrafluoropropeno, 2-cloro-2,3,3,3-tetrafluoropropanol, acetato de 2-cloro-2,3,3,3-tetrafluoropropilo o (2-cloro-2,3,3,3-tetrafluorop ropoxil) cloruro de zinc. |
| WO2010059493A1 (en) | 2008-11-19 | 2010-05-27 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| KR20110114529A (ko) | 2008-12-25 | 2011-10-19 | 아사히 가라스 가부시키가이샤 | 1,1-디클로로-2,3,3,3-테트라플루오로프로펜 및 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
| US8552227B2 (en) | 2009-01-05 | 2013-10-08 | E I Du Pont De Nemours And Company | Preparation of hydrofluoroolefins by dehydrofluorination |
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| KR20120016130A (ko) * | 2009-05-08 | 2012-02-22 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 하이드로플루오로올레핀 제조에서 모노플루오로아세테이트의 양을 감소시키는 방법 |
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| FR2948362B1 (fr) | 2009-07-23 | 2012-03-23 | Arkema France | Procede de preparation de composes fluores |
| FR2948361B1 (fr) * | 2009-07-23 | 2011-08-05 | Arkema France | Procede de preparation de composes fluores |
| FR2948360B1 (fr) | 2009-07-23 | 2011-08-05 | Arkema France | Procede de preparation de composes fluores olefiniques |
| US8779222B2 (en) * | 2009-08-31 | 2014-07-15 | Sumitomo Chemical Company, Limited | Method for producing 1,1,3-trichloro-1-propene |
| US20120214719A1 (en) * | 2009-10-26 | 2012-08-23 | Jose Luis Garcia Ojeda | Lubricating composition |
| JP5946410B2 (ja) * | 2010-02-19 | 2016-07-06 | ダイキン工業株式会社 | ２−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
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| FR2984886B1 (fr) | 2011-12-22 | 2013-12-20 | Arkema France | Procede de preparation de composes olefiniques fluores |
| WO2014046250A1 (ja) * | 2012-09-21 | 2014-03-27 | セントラル硝子株式会社 | １，２－ジクロロ－３，３，３－トリフルオロプロペンの製造方法 |
| US20140275651A1 (en) * | 2013-03-15 | 2014-09-18 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
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