US20020125122A1 - UV-activated chlorination process - Google Patents
UV-activated chlorination process Download PDFInfo
- Publication number
- US20020125122A1 US20020125122A1 US10/016,127 US1612701A US2002125122A1 US 20020125122 A1 US20020125122 A1 US 20020125122A1 US 1612701 A US1612701 A US 1612701A US 2002125122 A1 US2002125122 A1 US 2002125122A1
- Authority
- US
- United States
- Prior art keywords
- chlorine
- trifluoro
- process according
- liquid phase
- produce
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000005660 chlorination reaction Methods 0.000 title description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 56
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 56
- 239000000460 chlorine Substances 0.000 claims abstract description 56
- 239000007789 gas Substances 0.000 claims abstract description 15
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims abstract description 12
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims abstract description 12
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 10
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007858 starting material Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 6
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 claims abstract description 4
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 claims abstract description 3
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims description 8
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 abstract 1
- 230000001678 irradiating effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000011521 glass Substances 0.000 description 15
- 238000004817 gas chromatography Methods 0.000 description 9
- 230000005855 radiation Effects 0.000 description 9
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 8
- 239000005293 duran Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 229910020323 ClF3 Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 239000005388 borosilicate glass Substances 0.000 description 3
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940075417 cadmium iodide Drugs 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- DWRNSCDYNYYYHT-UHFFFAOYSA-K gallium(iii) iodide Chemical compound I[Ga](I)I DWRNSCDYNYYYHT-UHFFFAOYSA-K 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
Definitions
- the invention relates to a process for producing certain chlorine-containing alkanes through UV-light supported chlorination.
- Another object of the invention is to provide a process for producing chlorine-containing alkanes with a high reaction rate and high selectivity.
- the process is used to produce pentachloroethane from trichloroethylene, to produce 1,1,1,2-tetrachloro-2,2-difluoroethane from 1-chloro-1,1-difluoroethane, and to produce 1,1,1-trifluoro-2,2,2-trichloroethane from 1,1,1-trifluoro-2,2-dichloroethane.
- the molar ratio of starting compound to elemental chlorine ranges from 1:0.1 to 1:10 when attaching chlorine and from 1:0.01 to 1:5 when exchanging hydrogen for chlorine. If only one of two H atoms is to be exchanged in the exchange of hydrogen for chlorine, the ratio of starting compounds to chlorine falls in the upper range (lower chlorine content).
- the chlorine is used in an amount that is 0.9 times to 1.3 times the stoichiometrically required amount.
- Another variant of the invention concerns the purification of 1,1,1,3,3-pentafluorobutane (HFC-365mfc) with the aim of separating photochlorinatable olefinic impurities. It has been shown that the olefinic impurities, which are production-related, can essentially be selectively converted by the inventive photochlorination and separated in a simplified manner in the form of chlorination products.
- HFC-365mfc 1,1,1,3,3-pentafluorobutane
- radiation lamps e.g., Philips fluorescent tubes
- UV light of a wavelength at or above 280 nm ( ⁇ 280 nm).
- quartz glass the only prerequisite for this variant is that these lamps emit in the absorption range of the elemental chlorine.
- radiation lamps e.g., Hg medium or high-pressure discharge lamps, which also emit some lines in the range below 280 nm ( ⁇ 280 nm).
- borosilicate glasses This type of glass typically contains 7 to 13% B 2 O 3 , 70 to 80% SiO 2 , furthermore 2 to 7% Al 2 O 3 and 4 to 8% Na 2 O+K 2 O and 0 to 5% alkaline-earth metal oxides.
- Known trademarks for borosilicate glasses are Duran, Pyrex and Solidex. It is of course also possible to proceed by using on the one hand a radiation lamp that emits light above the indicated wavelengths and, in addition, glasses that are transparent for light above the indicated wavelength (i.e., that are non-transparent for light below the indicated wavelength).
- lamps e.g., Hg high-pressure discharge lamps, which due to a dopant emit primarily, or only, in the wavelength range at or above 280 nm.
- Hg high-pressure discharge lamps for instance, have a rather intensive band in the range of 254 nm which is filtered out, e.g., by borosilicate glass, as described above.
- this line is strongly suppressed. Surprising in these doped lamps is the frequently more than proportional increase in the conversion rate.
- HFC-365mfc can be purified in the liquid phase or in the gas phase.
- Pentachloroethane is advantageously produced in the liquid phase.
- CFC-112a, CFC-113a and HCFC-123 are advantageously produced in the gas phase. Continuous operation is especially facilitated by working in the gas phase.
- the process is advantageously conducted in a flow-through apparatus.
- the starting material (the corresponding hydrogen and halogen-containing starting compounds and chlorine) is continuously fed into the flow-through apparatus and the reaction product is continuously withdrawn in proportion to the amount introduced.
- the average residence time in the reaction vessel is preferably between 0.01 and 30 minutes, preferably between 0.01 and 3 minutes, particularly preferably between 0.5 and 3.0 minutes. Good results can be achieved even if the residence times are very short, e.g., between 0.04 and 0.5 minutes.
- the optimum average residence time which depends, among other things, on the lamp output and on the geometric parameters of the radiation apparatus (flow-through apparatus) can be determined by simple manual tests and analysis of the product stream, e.g., by gas chromatography.
- Apparatus double shell glass reactor (double shell for oil heating) with a submersible shaft made of Duran® 50 (400 ml reaction volume), equipped with a submersible Hg discharge lamp TQ 718 by Heraeus-Noblelight with water cooling.
- the 1,1,1-trifluoro-2,2-dichloroethane was evaporated with a pre-evaporator and was introduced from below as a gas into the reactor together with the chlorine (mixed).
- the product stream exited at the top.
- the reaction temperature was 110° C.
- the gas stream exiting the reactor was analyzed by gas chromatography (GC) (sampling in the gas collection tube).
- GC gas chromatography
- Tests 1 to 6 conducted with different chlorine feeds Test mole % Chlorine Conversion Rate 113a Selectivity 1 10 3.79 99.13 2 30 5.18 99.04 3 60 17.41 97.7 4 90 31.94 98.29 5 120 80.63 95.9 6 150 100 97.3
- Apparatus double shell glass reactor (double shell for oil heating) with submersible shaft made of quartz glass (400 ml reaction volume) equipped with submersible Hg discharge lamp TQ 718 of Heraeus Noblelight with water cooling.
- the 1,1,1-trifluoro-2,2-dichloroethane was evaporated and introduced from below as a gas into the reactor together with the chlorine.
- the reaction temperature was 110° C.
- a submersible Hg discharge lamp TQ 718 by Heraeus Noblelight was installed with a submersible tube made of Duran 50 glass. Irradiation thus took place at a wavelength of — >280 nm. The output was adjusted to 700 W.
- Test 12.2 62.0 kg educt treated with 110.9 g chlorine/test duration 5 hours.
- Test setup A 5 liter double shell vessel of Duran 50 glass with mounted reflux condenser, bubble counter and submersible tube with diffuser.
- the vessel also contained a water-cooled cooling coil.
- the vessel was irradiated from the outside with a Philips fluorescent tube (Philips reflector lamp No. 1099415, 40 Watts output).
- a submersible Hg discharge lamp TQ 718 by Heraeus Noblelight was installed with a submersible tube made of Duran® 50 glass. Irradiation thus took place at a wavelength of ⁇ >280 nm. The output was adjusted to 500 Watts.
- Test setup A 5 liter double shell vessel of Duran 50 glass with mounted reflux condenser, bubble counter and submersible tube with diffuser. The vessel also contained a water-cooled cooling coil. The apparatus was completely covered with aluminum foil.
- a mixture of 94.8 g (0.80 mole) 133a and a variable amount of chlorine were mixed and introduced in the form of a gas into a photochemical reactor holding 4.3 liters (diameter 100 mm, wall thickness 2 mm) made of Duran® 50.
- the reaction temperature during the 30-minute tests was 40° C.
- Irradiation was effected by 3 ⁇ 40 W UV lamps from Philips, type “Cleo Performance R-UVA 40 Watts” The lamps were cylindrically arranged around the photochemical reactor. The tests were evaluated by GC analysis of the reactor exhaust gas.
- Example 15 Feed: 94.8 g (0.80 mole) 133a, 5.67 g (0.08 mole) chlorine Result: Conversion: 13.98% Selectivity 123: 86% Selectivity 113a: 13%
- Example 16 Feed: 94.8 (0.80 mole) 133a, 17.01 g (0.24 mole) chlorine Result: Conversion: 25.2% Selectivity 123: 74% Selectivity 113a: 26%
- Example 17 Feed: 94.8 (0.80 mole) 133a, 34.03 g (0.48 mole) chlorine Result: Conversion: 38.8% Selectivity 123: 57.4% Selectivity 113a: 42%
- Example 18 Feed: 94.8 (0.80 mole) 133a, 51.05 g (0.08 mole) chlorine Result: Conversion: 45.8% Selectivity 123: 47% Selectivity 113a: 53%
- Example 19 Feed: 94.8 (0.80 mole) 133a, 68.06 g (0.96 mole) chlorine Result
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatment Of Water By Oxidation Or Reduction (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/627,755 US20040016633A1 (en) | 1999-06-16 | 2003-07-28 | UV-activated chlorination process |
| US11/008,109 US7282120B2 (en) | 1999-06-16 | 2004-12-10 | UV-activated chlorination process |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19927394.4 | 1999-06-16 | ||
| DE19927394 | 1999-06-16 | ||
| PCT/DE2000/001953 WO2000076945A2 (de) | 1999-06-16 | 2000-06-14 | Uv-aktivierte chlorierung |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE2000/001953 Continuation WO2000076945A2 (de) | 1999-06-16 | 2000-06-14 | Uv-aktivierte chlorierung |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/627,755 Continuation US20040016633A1 (en) | 1999-06-16 | 2003-07-28 | UV-activated chlorination process |
| US11/008,109 Continuation US7282120B2 (en) | 1999-06-16 | 2004-12-10 | UV-activated chlorination process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20020125122A1 true US20020125122A1 (en) | 2002-09-12 |
Family
ID=7911391
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/016,127 Abandoned US20020125122A1 (en) | 1999-06-16 | 2001-12-17 | UV-activated chlorination process |
| US10/627,755 Abandoned US20040016633A1 (en) | 1999-06-16 | 2003-07-28 | UV-activated chlorination process |
| US11/008,109 Expired - Fee Related US7282120B2 (en) | 1999-06-16 | 2004-12-10 | UV-activated chlorination process |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/627,755 Abandoned US20040016633A1 (en) | 1999-06-16 | 2003-07-28 | UV-activated chlorination process |
| US11/008,109 Expired - Fee Related US7282120B2 (en) | 1999-06-16 | 2004-12-10 | UV-activated chlorination process |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US20020125122A1 (de) |
| EP (1) | EP1189856B1 (de) |
| JP (1) | JP4891503B2 (de) |
| AT (1) | ATE312065T1 (de) |
| AU (1) | AU6148300A (de) |
| DE (2) | DE50011826D1 (de) |
| DK (1) | DK1189856T3 (de) |
| ES (1) | ES2251386T3 (de) |
| WO (1) | WO2000076945A2 (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6702929B2 (en) | 2000-12-15 | 2004-03-09 | Honeywell International Inc. | Purification of 1,1,1,3,3-pentafluorobutane |
| US20050087434A1 (en) * | 2003-10-22 | 2005-04-28 | Gregorio Tarancon | Method and apparatus for transforming chemical fluids using halogen or oxygen in a photo-treatment process |
| US7179949B2 (en) | 2000-08-10 | 2007-02-20 | Solvay (Societe Anonyme) | Process for obtaining a purified hydrofluoroalkane |
| US20100181186A1 (en) * | 2007-07-20 | 2010-07-22 | Solvay Fluor Gmbh | Process for obtaining a purified hydrofluoroalkane |
| CN114080377A (zh) * | 2019-07-01 | 2022-02-22 | 大金工业株式会社 | 烷烃的制造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2823206B1 (fr) * | 2001-04-05 | 2004-02-20 | Atofina | Procede photochimique semi-continu et dispositif pour sa mise en oeuvre |
| US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8975454B2 (en) | 2008-07-31 | 2015-03-10 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| BRPI0914033A2 (pt) * | 2008-10-13 | 2015-11-03 | Dow Global Technologies Inc | processo de uma etapa para a produção de de propenos clorados e fluorados e processo para preparar 2,3,3,3- tetrafluorprop-1 eno( 1,3,3,3- tetrafluorprop-1 eno (hfo-123ze) |
| EP2485996B1 (de) * | 2009-10-09 | 2016-06-15 | Blue Cube IP LLC | Verfahren zur herstellung chlorinierter und/oder fluorinierter propene |
| EP2485833A2 (de) * | 2009-10-09 | 2012-08-15 | Dow Global Technologies LLC | Adiabatische pfropfenströmungsreaktoren und verfahren zur herstellung eines chlorierten und/oder fluorierten propens und höheren alkens |
| WO2011044536A1 (en) | 2009-10-09 | 2011-04-14 | Dow Global Technologies, Inc | Process for the production of chlorinated and/or fluorinated propenes and higher alkenes |
| EP2485832B1 (de) | 2009-10-09 | 2016-11-23 | Blue Cube IP LLC | Verfahren zur herstellung eines chlorierten und/oder fluorierten propens in einem isothermischen multiröhrenreaktoren |
| WO2012166393A1 (en) | 2011-05-31 | 2012-12-06 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| CA2837292C (en) | 2011-05-31 | 2020-01-28 | Max Markus Tirtowidjojo | Process for the production of chlorinated propenes |
| EP2718249B1 (de) | 2011-06-08 | 2019-02-27 | Dow AgroSciences LLC | Verfahren zur herstellung von chlorierten und/oder fluorinierten propenen |
| US9233896B2 (en) | 2011-08-07 | 2016-01-12 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| EP2739596B1 (de) | 2011-08-07 | 2019-05-01 | Blue Cube IP LLC | Verfahren zur herstellung von chlorierten propenen |
| WO2013078035A1 (en) | 2011-11-21 | 2013-05-30 | Dow Global Technologies, Llc | Process for the production of chlorinated alkanes |
| JP6059246B2 (ja) | 2011-12-02 | 2017-01-11 | ブルー キューブ アイピー エルエルシー | 塩素化アルカンの製造方法 |
| JP6050375B2 (ja) | 2011-12-02 | 2016-12-21 | ブルー キューブ アイピー エルエルシー | クロロアルカンの製造方法 |
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| CN110128239A (zh) | 2011-12-22 | 2019-08-16 | 蓝立方知识产权有限责任公司 | 生产四氯甲烷的方法 |
| BR112014015123A2 (pt) | 2011-12-23 | 2017-06-13 | Dow Global Technologies Llc | processo para a produção de um ou mais alcenos ou compostos aromáticos |
| US9598334B2 (en) | 2012-09-20 | 2017-03-21 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| US9321707B2 (en) | 2012-09-20 | 2016-04-26 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| EP2900364B1 (de) | 2012-09-30 | 2018-06-13 | Blue Cube IP LLC | Wehrlöschung und verfahren damit |
| WO2014066083A1 (en) | 2012-10-26 | 2014-05-01 | Dow Global Technologies, Llc | Mixer and reactor and process incorporating the same |
| CA2893841C (en) | 2012-12-18 | 2018-07-24 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
| US9475740B2 (en) | 2012-12-19 | 2016-10-25 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| US9382176B2 (en) | 2013-02-27 | 2016-07-05 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| CN105026348A (zh) | 2013-03-09 | 2015-11-04 | 蓝立方知识产权有限责任公司 | 用于生产氯化烷烃的方法 |
| CN104058928B (zh) * | 2014-06-19 | 2017-11-21 | 巨化集团技术中心 | 一种含溴氟代烷烃合成中提高装置生产能力的方法 |
| JP7081596B2 (ja) * | 2017-06-27 | 2022-06-07 | Ａｇｃ株式会社 | ２－クロロ－１，１，１，２－テトラフルオロプロパンおよび／または３－クロロ－１，１，１，２－テトラフルオロプロパンの製造方法、ならびに２，３，３，３－テトラフルオロプロペンの製造方法 |
| WO2020024624A1 (en) | 2018-07-30 | 2020-02-06 | Fujian Yongjing Technology Co., Ltd | Manufacture process of hcfc-123 and/or hcfc-122 |
| WO2020098292A1 (en) | 2018-11-08 | 2020-05-22 | Fujian Yongjing Technology Co., Ltd | Method for manufacture of 1,1,1-trifluoro-2-chloroethane (hcfc 133a) and/or trfluoroethylamine (tfea) |
| JP7247045B2 (ja) * | 2019-07-26 | 2023-03-28 | 関東電化工業株式会社 | １，１，２－トリクロロ－２－フルオロエテン（ｔｃｆｅ）の製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB698127A (en) | 1951-03-14 | 1953-10-07 | Ici Ltd | Improvements in or relating to the production of tetrafluorodichloroethane |
| JPS5013179B2 (de) | 1972-08-31 | 1975-05-17 | ||
| US4060469A (en) * | 1976-12-21 | 1977-11-29 | Allied Chemical Corporation | Preparation of 1,1,1-trifluoro-2,2-dichloroethane |
| DE3371063D1 (en) | 1983-12-01 | 1987-05-27 | Dow Chemical Co | Process for the production of 1,1,2-trichloro-2,2-difluoroethane |
| US4948479A (en) * | 1989-06-07 | 1990-08-14 | Atochem North America, Inc. | Removal of unsaturated carbon compounds from 1,1-dichloro-1-fluoroethane |
| DE3923255A1 (de) * | 1989-07-14 | 1991-01-24 | Hoechst Ag | Verfahren zur herstellung von 1,1,1,-triflour-2,2-dichlorethan durch photochlorierung |
| US5336377A (en) * | 1991-12-18 | 1994-08-09 | Allied-Signal Inc. | Process for removing 2-chloro-1,1-difluoroethylene from 1,1,1,2-tetrafluoroethane and co-producing 2-chloro-1,1,1,2-tetrafluoroethane |
| CN1034999C (zh) * | 1993-07-05 | 1997-05-28 | 浙江省化工研究院 | 一种1，1，1-三氟-2，2，2-三氯乙烷的制备方法 |
| US5421971A (en) * | 1993-09-03 | 1995-06-06 | Alliedsignal Inc. | Hydrochlorofluorocarbons and hydrofluorocarbons and methods for producing the same |
| JPH08198783A (ja) * | 1995-01-18 | 1996-08-06 | Central Glass Co Ltd | １，１，１，３，３−ペンタフルオロブタンの製造方法 |
| US5944962A (en) * | 1995-10-03 | 1999-08-31 | Laroche Industries, Inc. | Process for photochlorination |
| EP0902776B1 (de) * | 1996-04-04 | 2002-06-19 | Honeywell International Inc. | Reinigung von 1,1,1,3,3-pentafluorpropan (r-245fa) |
| FR2754816B1 (fr) * | 1996-10-18 | 1998-12-04 | Atochem Elf Sa | Procede de purification d'hydrogenochlorofluoroethanes |
-
2000
- 2000-06-14 JP JP2001503414A patent/JP4891503B2/ja not_active Expired - Fee Related
- 2000-06-14 DE DE50011826T patent/DE50011826D1/de not_active Expired - Lifetime
- 2000-06-14 WO PCT/DE2000/001953 patent/WO2000076945A2/de not_active Ceased
- 2000-06-14 DE DE10029283A patent/DE10029283A1/de not_active Withdrawn
- 2000-06-14 ES ES00947799T patent/ES2251386T3/es not_active Expired - Lifetime
- 2000-06-14 AU AU61483/00A patent/AU6148300A/en not_active Abandoned
- 2000-06-14 EP EP00947799A patent/EP1189856B1/de not_active Expired - Lifetime
- 2000-06-14 AT AT00947799T patent/ATE312065T1/de not_active IP Right Cessation
- 2000-06-14 DK DK00947799T patent/DK1189856T3/da active
-
2001
- 2001-12-17 US US10/016,127 patent/US20020125122A1/en not_active Abandoned
-
2003
- 2003-07-28 US US10/627,755 patent/US20040016633A1/en not_active Abandoned
-
2004
- 2004-12-10 US US11/008,109 patent/US7282120B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7179949B2 (en) | 2000-08-10 | 2007-02-20 | Solvay (Societe Anonyme) | Process for obtaining a purified hydrofluoroalkane |
| US20070112231A1 (en) * | 2000-08-10 | 2007-05-17 | Solvay S.A. | Process for obtaining a purified hydrofluoroalkane |
| US7468467B2 (en) | 2000-08-10 | 2008-12-23 | Solvay S.A. | Process for obtaining a purified hydrofluoroalkane |
| US20090099394A1 (en) * | 2000-08-10 | 2009-04-16 | Solvay S.A. | Process for obtaining a purified hydrofluoroalkane |
| US7750195B2 (en) | 2000-08-10 | 2010-07-06 | Solvay S.A. | Process for obtaining a purified hydrofluoroalkane |
| US6702929B2 (en) | 2000-12-15 | 2004-03-09 | Honeywell International Inc. | Purification of 1,1,1,3,3-pentafluorobutane |
| US20050087434A1 (en) * | 2003-10-22 | 2005-04-28 | Gregorio Tarancon | Method and apparatus for transforming chemical fluids using halogen or oxygen in a photo-treatment process |
| US20100181186A1 (en) * | 2007-07-20 | 2010-07-22 | Solvay Fluor Gmbh | Process for obtaining a purified hydrofluoroalkane |
| CN114080377A (zh) * | 2019-07-01 | 2022-02-22 | 大金工业株式会社 | 烷烃的制造方法 |
| US20220119327A1 (en) * | 2019-07-01 | 2022-04-21 | Daikin Industries, Ltd. | Alkane production method |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050101811A1 (en) | 2005-05-12 |
| WO2000076945A2 (de) | 2000-12-21 |
| DK1189856T3 (da) | 2006-04-18 |
| EP1189856B1 (de) | 2005-12-07 |
| AU6148300A (en) | 2001-01-02 |
| DE10029283A1 (de) | 2000-12-21 |
| EP1189856A2 (de) | 2002-03-27 |
| US20040016633A1 (en) | 2004-01-29 |
| US7282120B2 (en) | 2007-10-16 |
| ES2251386T3 (es) | 2006-05-01 |
| JP2003502298A (ja) | 2003-01-21 |
| DE50011826D1 (de) | 2006-01-12 |
| ATE312065T1 (de) | 2005-12-15 |
| WO2000076945A3 (de) | 2001-05-31 |
| JP4891503B2 (ja) | 2012-03-07 |
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