DE2044986A1 - - Google Patents
Info
- Publication number
- DE2044986A1 DE2044986A1 DE19702044986 DE2044986A DE2044986A1 DE 2044986 A1 DE2044986 A1 DE 2044986A1 DE 19702044986 DE19702044986 DE 19702044986 DE 2044986 A DE2044986 A DE 2044986A DE 2044986 A1 DE2044986 A1 DE 2044986A1
- Authority
- DE
- Germany
- Prior art keywords
- exchange resin
- solution
- perfluorocarboxylic
- perfluorocarboxylic acids
- anion exchange
- 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.)
- Granted
Links
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 20
- 239000003957 anion exchange resin Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 10
- 229920000126 latex Polymers 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004816 latex Substances 0.000 claims description 9
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 238000005185 salting out Methods 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 238000010828 elution Methods 0.000 description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 8
- 239000003456 ion exchange resin Substances 0.000 description 8
- 229920003303 ion-exchange polymer Polymers 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- PKERFCBWBFEXPH-UHFFFAOYSA-N chloroethene;1,1-difluoroethene Chemical compound ClC=C.FC(F)=C PKERFCBWBFEXPH-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- -1 perfluoro- Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000006467 substitution reaction 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
- C02F2001/422—Treatment of water, waste water, or sewage by ion-exchange using anionic exchangers
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/36—Organic compounds containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7248369 | 1969-09-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2044986A1 true DE2044986A1 (enrdf_load_stackoverflow) | 1971-03-25 |
| DE2044986B2 DE2044986B2 (de) | 1977-08-25 |
| DE2044986C3 DE2044986C3 (de) | 1978-04-20 |
Family
ID=13490598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702044986 Expired DE2044986C3 (de) | 1969-09-12 | 1970-09-11 | Verfahren zur Gewinnung von Perfluorcarbonsäuren |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2044986C3 (enrdf_load_stackoverflow) |
| GB (1) | GB1314607A (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014431A3 (en) * | 1979-02-02 | 1981-02-11 | Hoechst Aktiengesellschaft | Process for the recovery of fluorinated emulsifying acids from basic ion exchangers |
| WO2000001647A3 (de) * | 1998-07-06 | 2000-04-06 | Solvay Fluor & Derivate | Herstellung von fluoridarmen organischen verbindungen |
| US6252105B1 (en) | 1998-07-06 | 2001-06-26 | Solvay Fluor Und Derivate Gmbh | Synthesis of low-fluoride organic compounds |
| US6518442B1 (en) | 1998-06-02 | 2003-02-11 | Dyneon Gmbh & Co., Kg | Process for the recovery of fluorinated alkandic acids from wastewater |
| US6593416B2 (en) | 2000-02-01 | 2003-07-15 | 3M Innovative Properties Company | Fluoropolymers |
| US6613941B1 (en) | 1998-06-02 | 2003-09-02 | 3M Innovative Properties Company | Method for recovering fluorinated alkanoic acids from waste waters |
| US6706193B1 (en) | 1999-07-17 | 2004-03-16 | 3M Innovative Properties Company | Method for recovering fluorinated emulsifiers from aqueous phases |
| US6720360B1 (en) | 2000-02-01 | 2004-04-13 | 3M Innovative Properties Company | Ultra-clean fluoropolymers |
| WO2011101342A1 (de) | 2010-02-18 | 2011-08-25 | Lanxess Deutschland Gmbh | Behandlung von abwässern enthaltend fluorierte säuren oder deren salze |
| EP2431334A1 (de) | 2010-09-16 | 2012-03-21 | LANXESS Deutschland GmbH | Behandlung von Abwässern aus der Galvanikindustrie |
| WO2015053235A1 (ja) | 2013-10-10 | 2015-04-16 | 旭硝子株式会社 | 含フッ素乳化剤の回収方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100360484C (zh) | 2003-05-14 | 2008-01-09 | 国际壳牌研究有限公司 | 除去含卤素的有机化合物的方法 |
| WO2007043278A1 (ja) * | 2005-10-14 | 2007-04-19 | Asahi Glass Company, Limited | 塩基性陰イオン交換樹脂の再生方法 |
| WO2010018810A1 (ja) * | 2008-08-12 | 2010-02-18 | 和光純薬工業株式会社 | 前処理カラムの充填剤用ポリマー |
-
1970
- 1970-09-09 GB GB4308170A patent/GB1314607A/en not_active Expired
- 1970-09-11 DE DE19702044986 patent/DE2044986C3/de not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014431A3 (en) * | 1979-02-02 | 1981-02-11 | Hoechst Aktiengesellschaft | Process for the recovery of fluorinated emulsifying acids from basic ion exchangers |
| US6518442B1 (en) | 1998-06-02 | 2003-02-11 | Dyneon Gmbh & Co., Kg | Process for the recovery of fluorinated alkandic acids from wastewater |
| US6613941B1 (en) | 1998-06-02 | 2003-09-02 | 3M Innovative Properties Company | Method for recovering fluorinated alkanoic acids from waste waters |
| WO2000001647A3 (de) * | 1998-07-06 | 2000-04-06 | Solvay Fluor & Derivate | Herstellung von fluoridarmen organischen verbindungen |
| US6252105B1 (en) | 1998-07-06 | 2001-06-26 | Solvay Fluor Und Derivate Gmbh | Synthesis of low-fluoride organic compounds |
| EP1481958A1 (de) * | 1998-07-06 | 2004-12-01 | Solvay Fluor und Derivate GmbH | Herstellung von fluoridarmen organischen Verbindungen |
| US6706193B1 (en) | 1999-07-17 | 2004-03-16 | 3M Innovative Properties Company | Method for recovering fluorinated emulsifiers from aqueous phases |
| US6720360B1 (en) | 2000-02-01 | 2004-04-13 | 3M Innovative Properties Company | Ultra-clean fluoropolymers |
| US6593416B2 (en) | 2000-02-01 | 2003-07-15 | 3M Innovative Properties Company | Fluoropolymers |
| WO2011101342A1 (de) | 2010-02-18 | 2011-08-25 | Lanxess Deutschland Gmbh | Behandlung von abwässern enthaltend fluorierte säuren oder deren salze |
| EP2431334A1 (de) | 2010-09-16 | 2012-03-21 | LANXESS Deutschland GmbH | Behandlung von Abwässern aus der Galvanikindustrie |
| WO2012035087A1 (de) | 2010-09-16 | 2012-03-22 | Lanxess Deutschland Gmbh | Behandlung von abwässern aus der galvanikindustrie |
| WO2015053235A1 (ja) | 2013-10-10 | 2015-04-16 | 旭硝子株式会社 | 含フッ素乳化剤の回収方法 |
| US9708246B2 (en) | 2013-10-10 | 2017-07-18 | Asahi Glass Company, Limited | Method for recovering fluorinated emulsifier |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1314607A (en) | 1973-04-26 |
| DE2044986C3 (de) | 1978-04-20 |
| DE2044986B2 (de) | 1977-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |