JP3863950B2 - アジピン酸製造における触媒の回収方法 - Google Patents
アジピン酸製造における触媒の回収方法 Download PDFInfo
- Publication number
- JP3863950B2 JP3863950B2 JP25734896A JP25734896A JP3863950B2 JP 3863950 B2 JP3863950 B2 JP 3863950B2 JP 25734896 A JP25734896 A JP 25734896A JP 25734896 A JP25734896 A JP 25734896A JP 3863950 B2 JP3863950 B2 JP 3863950B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ion exchanger
- reaction solution
- copper
- 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.)
- Expired - Fee Related
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 26
- 239000001361 adipic acid Substances 0.000 title claims description 13
- 235000011037 adipic acid Nutrition 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 13
- 239000003054 catalyst Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 47
- 239000010949 copper Substances 0.000 claims description 31
- 150000002500 ions Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 25
- 229910052742 iron Inorganic materials 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052802 copper Inorganic materials 0.000 claims description 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 13
- -1 iron ions Chemical class 0.000 claims description 13
- 229910017604 nitric acid Inorganic materials 0.000 claims description 13
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 150000003681 vanadium Chemical class 0.000 claims description 4
- 229910001431 copper ion Inorganic materials 0.000 claims description 3
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical group NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims description 3
- 229910001456 vanadium ion Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 229910052720 vanadium Inorganic materials 0.000 description 11
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229920005990 polystyrene resin Polymers 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
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VIHKPMPEMDBCOA-UHFFFAOYSA-N P(O)(O)=O.NC Chemical group P(O)(O)=O.NC VIHKPMPEMDBCOA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000001133 acceleration 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
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZIXPVRHDBQPBDT-UHFFFAOYSA-N methylaminophosphonic acid Chemical compound CNP(O)(O)=O ZIXPVRHDBQPBDT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003682 vanadium compounds Chemical class 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)
Applications Claiming Priority (2)
| 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 |
| DE19533688.7 | 1995-09-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH09124545A JPH09124545A (ja) | 1997-05-13 |
| JPH09124545A5 JPH09124545A5 (enExample) | 2004-09-16 |
| JP3863950B2 true JP3863950B2 (ja) | 2006-12-27 |
Family
ID=7771913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25734896A Expired - Fee Related 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 |
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) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2794991B1 (fr) * | 1999-06-15 | 2002-03-15 | Rhone Poulenc Fibres | Procede de separation du fer d'autres ions metalliques, et procede de recyclage des catalyseurs dans les reactions d'oxydation d'alcools en acide carboxylique |
| 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
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 |
| DE19533688A1 (de) | 1997-03-13 |
| US5723098A (en) | 1998-03-03 |
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