DE19533688A1 - Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung - Google Patents
Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-HerstellungInfo
- Publication number
- DE19533688A1 DE19533688A1 DE19533688A DE19533688A DE19533688A1 DE 19533688 A1 DE19533688 A1 DE 19533688A1 DE 19533688 A DE19533688 A DE 19533688A DE 19533688 A DE19533688 A DE 19533688A DE 19533688 A1 DE19533688 A1 DE 19533688A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- ion exchanger
- iron
- adipic acid
- vanadium
- 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.)
- Withdrawn
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 14
- 239000001361 adipic acid Substances 0.000 title claims description 11
- 235000011037 adipic acid Nutrition 0.000 title claims description 11
- 239000003054 catalyst Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000011084 recovery Methods 0.000 title description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 47
- 239000010949 copper Substances 0.000 claims description 33
- 150000002500 ions Chemical class 0.000 claims description 23
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 19
- 229910017604 nitric acid Inorganic materials 0.000 claims description 19
- 229910052742 iron Inorganic materials 0.000 claims description 18
- 229910052802 copper Inorganic materials 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- -1 iron ions Chemical class 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000003681 vanadium Chemical class 0.000 claims description 4
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical group NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229910052720 vanadium Inorganic materials 0.000 description 10
- 230000008929 regeneration Effects 0.000 description 9
- 238000011069 regeneration method Methods 0.000 description 9
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 9
- 230000001172 regenerating effect Effects 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- ZIXPVRHDBQPBDT-UHFFFAOYSA-N methylaminophosphonic acid Chemical compound CNP(O)(O)=O ZIXPVRHDBQPBDT-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical group [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical group [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 229910001456 vanadium ion Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 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
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19533688A DE19533688A1 (de) | 1995-09-12 | 1995-09-12 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
| ES96113887T ES2140001T3 (es) | 1995-09-12 | 1996-08-30 | Procedimiento para la recuperacion de catalizadores en la fabricacion de acido adipico. |
| DE59603546T DE59603546D1 (de) | 1995-09-12 | 1996-08-30 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
| EP96113887A EP0761636B1 (de) | 1995-09-12 | 1996-08-30 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
| US08/706,473 US5723098A (en) | 1995-09-12 | 1996-09-04 | Process for the recovery of catalysts in adipic acid production |
| CA002185089A CA2185089A1 (en) | 1995-09-12 | 1996-09-09 | Process for the recovery of catalysts in adipic acid production |
| JP25734896A JP3863950B2 (ja) | 1995-09-12 | 1996-09-09 | アジピン酸製造における触媒の回収方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19533688A DE19533688A1 (de) | 1995-09-12 | 1995-09-12 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19533688A1 true DE19533688A1 (de) | 1997-03-13 |
Family
ID=7771913
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19533688A Withdrawn DE19533688A1 (de) | 1995-09-12 | 1995-09-12 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
| DE59603546T Expired - Fee Related DE59603546D1 (de) | 1995-09-12 | 1996-08-30 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59603546T Expired - Fee Related DE59603546D1 (de) | 1995-09-12 | 1996-08-30 | Verfahren zur Wiedergewinnung von Katalysatoren bei der Adipinsäure-Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5723098A (enExample) |
| EP (1) | EP0761636B1 (enExample) |
| JP (1) | JP3863950B2 (enExample) |
| CA (1) | CA2185089A1 (enExample) |
| DE (2) | DE19533688A1 (enExample) |
| ES (1) | ES2140001T3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2226429C2 (ru) * | 1999-06-15 | 2004-04-10 | Родиа Полиамид Интермедиэйтс | Селективное отделение железа обработкой ионообменной смолой, содержащей группы дифосфоновых кислот |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6982234B2 (en) | 2000-06-01 | 2006-01-03 | Gtc Technology Inc. | Methods and apparatus for removing catalyst from oxidation reactor effluent |
| WO2001092195A2 (en) * | 2000-06-01 | 2001-12-06 | Gtc Technology Corporation | Methods and apparatus for removing catalyst from oxidation reactor effluent |
| US8277984B2 (en) * | 2006-05-02 | 2012-10-02 | The Penn State Research Foundation | Substrate-enhanced microbial fuel cells |
| CN101200335B (zh) * | 2007-10-19 | 2010-05-26 | 中南大学 | 一种含铜、钒废水综合回收方法 |
| WO2010078423A2 (en) * | 2008-12-30 | 2010-07-08 | The Penn State Research Foundation | Cathodes for microbial electrolysis cells and microbial fuel cells |
| CN104684644A (zh) | 2012-08-21 | 2015-06-03 | 陶氏环球技术有限责任公司 | 利用氨基酸洗脱剂从螯合树脂中洗脱金属离子 |
| US9546426B2 (en) | 2013-03-07 | 2017-01-17 | The Penn State Research Foundation | Methods for hydrogen gas production |
| WO2014173810A1 (de) | 2013-04-23 | 2014-10-30 | Basf Se | Verfahren zur entfernung von kupfer |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2897050A (en) * | 1954-04-28 | 1959-07-28 | Air Reduction | Separation of rare earth values by means of a cation exchange resin |
| US2858335A (en) * | 1954-08-18 | 1958-10-28 | Cp Hall Co | Purification of dicarboxylic acid |
| US3240556A (en) * | 1961-04-11 | 1966-03-15 | Regents | Process for the recovery of metal values |
| US4375552A (en) * | 1969-01-31 | 1983-03-01 | C. P. Hall Company | Nitric acid process for production of adipic acid from hydrocarbons |
| US3554692A (en) * | 1969-05-26 | 1971-01-12 | Celanese Corp | Recovery of copper and vanadium from a solution containing iron |
| US3983208A (en) * | 1975-01-27 | 1976-09-28 | Celanese Corporation | Recovery of vanadium and copper catalyst metals using ketones |
| US3965164A (en) * | 1975-01-27 | 1976-06-22 | Celanese Corporation | Recovery of oxidation catalyst metals from adipic acid production |
| DE4100505A1 (de) * | 1991-01-10 | 1992-07-16 | Basf Ag | Verfahren zur aufarbeitung von mutterlaugen, die bei der herstellung von adipinsaeure anfallen |
| US5182251A (en) * | 1991-10-10 | 1993-01-26 | Brigham Young University | Aminoalkylphosphonic acid containing ligands attached to solid supports for removal of metal ions |
| US5281631A (en) * | 1991-12-20 | 1994-01-25 | Arch Development Corp. | Phosphonic acid based ion exchange resins |
-
1995
- 1995-09-12 DE DE19533688A patent/DE19533688A1/de not_active Withdrawn
-
1996
- 1996-08-30 ES ES96113887T patent/ES2140001T3/es not_active Expired - Lifetime
- 1996-08-30 DE DE59603546T patent/DE59603546D1/de not_active Expired - Fee Related
- 1996-08-30 EP EP96113887A patent/EP0761636B1/de not_active Expired - Lifetime
- 1996-09-04 US US08/706,473 patent/US5723098A/en not_active Expired - Fee Related
- 1996-09-09 JP JP25734896A patent/JP3863950B2/ja not_active Expired - Fee Related
- 1996-09-09 CA CA002185089A patent/CA2185089A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2226429C2 (ru) * | 1999-06-15 | 2004-04-10 | Родиа Полиамид Интермедиэйтс | Селективное отделение железа обработкой ионообменной смолой, содержащей группы дифосфоновых кислот |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59603546D1 (de) | 1999-12-09 |
| CA2185089A1 (en) | 1997-03-13 |
| ES2140001T3 (es) | 2000-02-16 |
| JPH09124545A (ja) | 1997-05-13 |
| EP0761636A1 (de) | 1997-03-12 |
| EP0761636B1 (de) | 1999-11-03 |
| JP3863950B2 (ja) | 2006-12-27 |
| US5723098A (en) | 1998-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |