DE69712137T2 - Selektive Entfernung von Perfluorisobutylen aus halogenierten Kohlenwasserstoffströmen - Google Patents
Selektive Entfernung von Perfluorisobutylen aus halogenierten KohlenwasserstoffströmenInfo
- Publication number
- DE69712137T2 DE69712137T2 DE69712137T DE69712137T DE69712137T2 DE 69712137 T2 DE69712137 T2 DE 69712137T2 DE 69712137 T DE69712137 T DE 69712137T DE 69712137 T DE69712137 T DE 69712137T DE 69712137 T2 DE69712137 T2 DE 69712137T2
- Authority
- DE
- Germany
- Prior art keywords
- pfib
- activated carbon
- stream
- adsorbed
- perfluoroisobutylene
- 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
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 title claims description 106
- 150000008282 halocarbons Chemical class 0.000 title description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 122
- 238000000034 method Methods 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000007789 gas Substances 0.000 claims description 36
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 26
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000011261 inert gas Substances 0.000 claims description 8
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 5
- IMRLDNHHTCXOOR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propane Chemical compound FC(F)(F)C(C(F)(F)F)C(F)(F)F IMRLDNHHTCXOOR-UHFFFAOYSA-N 0.000 claims description 2
- 230000001172 regenerating effect Effects 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 description 36
- 238000011069 regeneration method Methods 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- 229910052799 carbon Inorganic materials 0.000 description 28
- 238000001179 sorption measurement Methods 0.000 description 22
- 238000003795 desorption Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000011148 porous material Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 8
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004341 Octafluorocyclobutane Substances 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 PFIB Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- ICXADQHBWHLSCI-UHFFFAOYSA-N dubinine Natural products C1=CC=C2C(OC)=C(CC(O3)C(C)(O)COC(C)=O)C3=NC2=C1 ICXADQHBWHLSCI-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 1
- RAEAYTICAPHWJW-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)C(F)(F)F RAEAYTICAPHWJW-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 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
- 229940043430 calcium compound Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 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
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000013022 venting Methods 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
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/690,923 US5705719A (en) | 1996-08-01 | 1996-08-01 | Selective removal of perfluoroisobutylene from streams of halogenated hydrocarbons |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69712137D1 DE69712137D1 (de) | 2002-05-29 |
| DE69712137T2 true DE69712137T2 (de) | 2002-11-07 |
Family
ID=24774511
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69730878T Expired - Lifetime DE69730878T2 (de) | 1996-08-01 | 1997-07-25 | Verfahren zur Umwandlung von Perfluorisobutylen zu CF3 CH2 CF3 |
| DE69712137T Expired - Lifetime DE69712137T2 (de) | 1996-08-01 | 1997-07-25 | Selektive Entfernung von Perfluorisobutylen aus halogenierten Kohlenwasserstoffströmen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69730878T Expired - Lifetime DE69730878T2 (de) | 1996-08-01 | 1997-07-25 | Verfahren zur Umwandlung von Perfluorisobutylen zu CF3 CH2 CF3 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5705719A (enExample) |
| EP (2) | EP0822170B1 (enExample) |
| JP (1) | JP4057103B2 (enExample) |
| DE (2) | DE69730878T2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6281395B1 (en) | 1998-04-03 | 2001-08-28 | E. I. Du Pont De Nemours And Company | 1,1,1,2,3,3,3-heptafluoropropane manufacturing process |
| US20020032356A1 (en) | 2000-07-14 | 2002-03-14 | Gelblum Peter Gideon | Synthesis of perfluoroolefins |
| US7317071B2 (en) | 2002-03-01 | 2008-01-08 | Daikin Industries, Ltd. | Process for producing fluoromonomer |
| JP5556177B2 (ja) * | 2007-09-04 | 2014-07-23 | ダイキン工業株式会社 | 含フッ素化合物の吸着方法と回収方法 |
| GB0918069D0 (en) | 2009-10-15 | 2009-12-02 | Ineos Fluor Holdings Ltd | Process |
| CN103073385B (zh) * | 2012-12-30 | 2016-01-20 | 江苏梅兰化工有限公司 | 一种吸收降解全氟异丁烯的方法 |
| WO2025019321A1 (en) | 2023-07-14 | 2025-01-23 | Claros Technologies Inc. | Methods and systems of pfas destruction using uv irradiation at 222 nanometers |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3696156A (en) * | 1970-04-03 | 1972-10-03 | Du Pont | Process for purification of fluoroperhalocarbons |
| DD221088A1 (de) * | 1983-09-12 | 1985-04-17 | Univ Schiller Jena | Verfahren und anordnung zur entgiftung von f-kohlenstoffhaltigen abgasen |
| US5300714A (en) * | 1990-05-18 | 1994-04-05 | Minnesota Mining And Manufacturing Company | Method of purifying saturated fluoroperhalocarbon liquids |
| GB9107344D0 (en) * | 1991-04-08 | 1991-05-22 | Ici Plc | Purification process |
| US5600040A (en) * | 1992-07-17 | 1997-02-04 | E. I. Du Pont De Nemours And Company | Separation of tetrafluoroethane isomers |
| US5420368A (en) * | 1994-06-29 | 1995-05-30 | E. I. Du Pont De Nemours And Company | Production CF3 CH2 CF3 and/or CF3 CH═CF2 by the conversion of fluorinated ethers |
| US5594159A (en) * | 1995-04-13 | 1997-01-14 | E I Du Pont De Nemours And Company | Producing CF3 CH2 CF3 and/or CF3 CH═CF2 by the conversion of alpha-hydroperfluoroisobutyric acid compounds |
-
1996
- 1996-08-01 US US08/690,923 patent/US5705719A/en not_active Expired - Lifetime
-
1997
- 1997-07-25 DE DE69730878T patent/DE69730878T2/de not_active Expired - Lifetime
- 1997-07-25 EP EP97112790A patent/EP0822170B1/en not_active Expired - Lifetime
- 1997-07-25 DE DE69712137T patent/DE69712137T2/de not_active Expired - Lifetime
- 1997-07-25 EP EP01201787A patent/EP1122232B1/en not_active Expired - Lifetime
- 1997-07-31 JP JP21893197A patent/JP4057103B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0822170A1 (en) | 1998-02-04 |
| DE69730878D1 (de) | 2004-10-28 |
| DE69712137D1 (de) | 2002-05-29 |
| JP4057103B2 (ja) | 2008-03-05 |
| US5705719A (en) | 1998-01-06 |
| JPH1067692A (ja) | 1998-03-10 |
| EP1122232A1 (en) | 2001-08-08 |
| EP0822170B1 (en) | 2002-04-24 |
| EP1122232B1 (en) | 2004-09-22 |
| DE69730878T2 (de) | 2005-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |