JP4547256B2 - ヘキサフルオロプロピレンの合成 - Google Patents
ヘキサフルオロプロピレンの合成 Download PDFInfo
- Publication number
- JP4547256B2 JP4547256B2 JP2004517777A JP2004517777A JP4547256B2 JP 4547256 B2 JP4547256 B2 JP 4547256B2 JP 2004517777 A JP2004517777 A JP 2004517777A JP 2004517777 A JP2004517777 A JP 2004517777A JP 4547256 B2 JP4547256 B2 JP 4547256B2
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- lining
- reaction
- alloy
- tube
- 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
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 title claims description 23
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 62
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 40
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 35
- 238000000197 pyrolysis Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 21
- 239000011651 chromium Substances 0.000 claims description 19
- 229910052804 chromium Inorganic materials 0.000 claims description 18
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 18
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 229910000990 Ni alloy Inorganic materials 0.000 claims description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 8
- 229910045601 alloy Inorganic materials 0.000 description 33
- 239000000956 alloy Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 19
- 229910001026 inconel Inorganic materials 0.000 description 16
- 230000007797 corrosion Effects 0.000 description 15
- 238000005260 corrosion Methods 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000004341 Octafluorocyclobutane Substances 0.000 description 6
- 239000004035 construction material Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 6
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229910021563 chromium fluoride Inorganic materials 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 5
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 229910001063 inconels 617 Inorganic materials 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003466 welding Methods 0.000 description 3
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- -1 HCl or HF Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000374 eutectic mixture Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004812 organic fluorine compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- GQUXQQYWQKRCPL-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorocyclopropane Chemical compound FC1(F)C(F)(F)C1(F)F GQUXQQYWQKRCPL-UHFFFAOYSA-N 0.000 description 1
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- 229910018487 Ni—Cr Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 150000001845 chromium compounds Chemical group 0.000 description 1
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009683 ultrasonic thickness measurement Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000011800 void 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
-
- 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
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39191502P | 2002-06-26 | 2002-06-26 | |
| PCT/US2003/019913 WO2004002929A1 (en) | 2002-06-26 | 2003-06-25 | Synthesis of hexafluoropropylene |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005535639A JP2005535639A (ja) | 2005-11-24 |
| JP2005535639A5 JP2005535639A5 (https=) | 2006-07-13 |
| JP4547256B2 true JP4547256B2 (ja) | 2010-09-22 |
Family
ID=30000777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004517777A Expired - Lifetime JP4547256B2 (ja) | 2002-06-26 | 2003-06-25 | ヘキサフルオロプロピレンの合成 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6924403B2 (https=) |
| EP (1) | EP1515930B1 (https=) |
| JP (1) | JP4547256B2 (https=) |
| CN (1) | CN1319919C (https=) |
| DE (1) | DE60317199T2 (https=) |
| WO (1) | WO2004002929A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6958422B2 (en) * | 2003-12-17 | 2005-10-25 | E. I. Du Pont De Nemours And Company | Pyrolysis process |
| KR20120093202A (ko) * | 2009-10-09 | 2012-08-22 | 다우 글로벌 테크놀로지스 엘엘씨 | 단열식 플러그 흐름 반응기 및 염화 및/또는 불화 프로펜 및 고급 알켄의 제조 방법 |
| JP5782038B2 (ja) * | 2009-10-09 | 2015-09-24 | ダウ グローバル テクノロジーズ エルエルシー | 等温多管式反応器及び該反応器を組み込んだプロセス |
| JP5767231B2 (ja) | 2009-10-09 | 2015-08-19 | ダウ グローバル テクノロジーズ エルエルシー | 塩素化及び／又はフッ素化されたプロペン及びより高級なアルケンを製造するプロセス |
| US9056808B2 (en) | 2011-05-31 | 2015-06-16 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| KR20140068852A (ko) * | 2011-06-27 | 2014-06-09 | 식스포인트 머터리얼즈 인코퍼레이티드 | 전이금속 질화물을 함유하는 전극을 지닌 울트라커패시터 |
| US8907148B2 (en) | 2011-08-07 | 2014-12-09 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
| CN103717557A (zh) | 2011-08-07 | 2014-04-09 | 陶氏环球技术有限责任公司 | 生产氯化的丙烯的方法 |
| IN2014CN03748A (https=) | 2011-11-21 | 2015-09-25 | Dow Global Technologies Llc | |
| EP2785671B1 (en) | 2011-12-02 | 2017-03-01 | Blue Cube IP LLC | Process for the production of chlorinated propanes |
| 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 |
| JP6170068B2 (ja) | 2011-12-13 | 2017-07-26 | ブルー キューブ アイピー エルエルシー | 塩素化プロパン及びプロペンの製造方法 |
| CN104011000A (zh) | 2011-12-22 | 2014-08-27 | 陶氏环球技术有限责任公司 | 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 |
| EP2897930A1 (en) | 2012-09-20 | 2015-07-29 | Dow Global Technologies LLC | Process for the production of chlorinated propenes |
| EP2897932A1 (en) | 2012-09-20 | 2015-07-29 | Dow Global Technologies LLC | Process for the production of chlorinated propenes |
| JP6272878B2 (ja) | 2012-09-30 | 2018-01-31 | ブルー キューブ アイピー エルエルシー | せきクエンチおよびそれを組み込んだ方法 |
| EP2911773B1 (en) | 2012-10-26 | 2017-10-04 | Blue Cube IP 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 |
| WO2014100039A1 (en) | 2012-12-19 | 2014-06-26 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| JP2016507590A (ja) | 2013-02-27 | 2016-03-10 | ブルー キューブ アイピー エルエルシー | 塩素化プロペンを生成するための方法 |
| WO2014164368A1 (en) | 2013-03-09 | 2014-10-09 | Dow Global Technologies Llc | Process for the production of chlorinated alkanes |
| EP3662997B1 (en) | 2016-07-20 | 2021-03-17 | Umicore Shokubai Japan Co., Ltd. | Catalyst for purifying exhaust gas from internal combustion engine, and exhaust gas purification method using said catalyst |
| EP3696382A1 (en) | 2016-07-20 | 2020-08-19 | Umicore Shokubai Japan Co., Ltd. | Exhaust gas purification catalyst for internal combustion engine, and exhaust gas purifying method using said exhaust gas purification catalyst |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE23425E (en) * | 1951-10-30 | Polyfluorinated compounds | ||
| US2394581A (en) * | 1943-10-04 | 1946-02-12 | Kinetic Chemicals Inc | Pyrolysis of tetrafluoroethylene polymer |
| US2758138A (en) * | 1954-05-06 | 1956-08-07 | Du Pont | Pyrolysis process for making perfluoropropene from tetrafluoroethylene |
| US2970176A (en) * | 1957-10-31 | 1961-01-31 | Du Pont | Pyrolysis of fluorocarbons to hexafluoropropylene |
| NL122622C (https=) * | 1960-09-28 | |||
| US3446858A (en) * | 1963-03-30 | 1969-05-27 | Daikin Ind Ltd | Process for the manufacture of hexafluoropropene |
| US3873630A (en) * | 1972-06-12 | 1975-03-25 | Du Pont | Process for pyrolyzing tetrafluoroethylene to hexafluoropropylene |
| US5334783A (en) * | 1988-03-14 | 1994-08-02 | Hoechst Aktiengesellschaft | Process for the preparation of hexafluoropropene |
| DE58904105D1 (de) * | 1988-03-14 | 1993-05-27 | Hoechst Ag | Verfahren zur herstellung von hexafluorpropen. |
| US6013890A (en) * | 1997-10-20 | 2000-01-11 | Welding Services, Inc. | Dual pass weld overlay method and apparatus |
| US6540933B1 (en) * | 1998-06-02 | 2003-04-01 | E. I. Du Pont De Nemours And Company | Process for the production of hexafluoropropylene from CC1F2CC1FCF3 and azeotropes of CC1F2CC1FCF3 with HF |
-
2003
- 2003-05-07 US US10/431,407 patent/US6924403B2/en not_active Expired - Lifetime
- 2003-06-25 EP EP03762008A patent/EP1515930B1/en not_active Expired - Lifetime
- 2003-06-25 CN CNB038149206A patent/CN1319919C/zh not_active Expired - Lifetime
- 2003-06-25 WO PCT/US2003/019913 patent/WO2004002929A1/en not_active Ceased
- 2003-06-25 JP JP2004517777A patent/JP4547256B2/ja not_active Expired - Lifetime
- 2003-06-25 DE DE60317199T patent/DE60317199T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60317199T2 (de) | 2008-08-14 |
| DE60317199D1 (en) | 2007-12-13 |
| WO2004002929A1 (en) | 2004-01-08 |
| CN1319919C (zh) | 2007-06-06 |
| EP1515930A1 (en) | 2005-03-23 |
| US6924403B2 (en) | 2005-08-02 |
| US20040002621A1 (en) | 2004-01-01 |
| JP2005535639A (ja) | 2005-11-24 |
| CN1662480A (zh) | 2005-08-31 |
| EP1515930B1 (en) | 2007-10-31 |
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