JP2004534778A - ジニトリルの環境調和型水素化プロセス - Google Patents
ジニトリルの環境調和型水素化プロセス Download PDFInfo
- Publication number
- JP2004534778A JP2004534778A JP2003500042A JP2003500042A JP2004534778A JP 2004534778 A JP2004534778 A JP 2004534778A JP 2003500042 A JP2003500042 A JP 2003500042A JP 2003500042 A JP2003500042 A JP 2003500042A JP 2004534778 A JP2004534778 A JP 2004534778A
- Authority
- JP
- Japan
- Prior art keywords
- quaternary ammonium
- hydroxide
- dinitrile
- catalyst
- modifier
- 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- Withdrawn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
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 73
- 239000001257 hydrogen Substances 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 48
- 239000003607 modifier Substances 0.000 claims abstract description 42
- 230000008569 process Effects 0.000 claims abstract description 42
- 150000004985 diamines Chemical class 0.000 claims abstract description 21
- 125000005219 aminonitrile group Chemical group 0.000 claims abstract description 19
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 35
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 17
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical group [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 13
- 239000000908 ammonium hydroxide Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 229910021472 group 8 element Inorganic materials 0.000 claims description 8
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 7
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 6
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical group O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002407 reforming Methods 0.000 claims description 4
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 claims description 3
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 3
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 3
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 claims description 3
- 125000005496 phosphonium group Chemical group 0.000 claims 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 68
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 39
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 13
- 239000003518 caustics Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 10
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 229910052759 nickel Inorganic materials 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000010926 purge Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 8
- 230000007613 environmental effect Effects 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000000743 hydrocarbylene group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- -1 sodium hydroxide) Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000006104 solid solution Substances 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- YUXPYTMXIQEMOG-UHFFFAOYSA-N 8-aminooctanenitrile Chemical compound NCCCCCCCC#N YUXPYTMXIQEMOG-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- RSHBFZCIFFBTEW-UHFFFAOYSA-M tetrabutylazanium;thiocyanate Chemical compound [S-]C#N.CCCC[N+](CCCC)(CCCC)CCCC RSHBFZCIFFBTEW-UHFFFAOYSA-M 0.000 description 1
- OAEZRJNGCVFHCM-UHFFFAOYSA-N tetramethylazanium;pentahydrate Chemical compound O.O.O.O.O.C[N+](C)(C)C OAEZRJNGCVFHCM-UHFFFAOYSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/871,102 US6376714B1 (en) | 2001-05-31 | 2001-05-31 | Environmentally friendly process for the hydrogenation of dinitriles |
| PCT/US2002/016374 WO2002096862A2 (en) | 2001-05-31 | 2002-05-24 | Environmentally friendly process for the hydrogenation of dinitriles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004534778A true JP2004534778A (ja) | 2004-11-18 |
| JP2004534778A5 JP2004534778A5 (enExample) | 2005-12-22 |
Family
ID=25356731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003500042A Withdrawn JP2004534778A (ja) | 2001-05-31 | 2002-05-24 | ジニトリルの環境調和型水素化プロセス |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6376714B1 (enExample) |
| EP (1) | EP1392646A2 (enExample) |
| JP (1) | JP2004534778A (enExample) |
| KR (1) | KR20040004667A (enExample) |
| CN (1) | CN1531523A (enExample) |
| BR (1) | BR0210082A (enExample) |
| CA (1) | CA2444442A1 (enExample) |
| MX (1) | MXPA03010927A (enExample) |
| MY (1) | MY134178A (enExample) |
| PL (1) | PL364602A1 (enExample) |
| RU (1) | RU2003137530A (enExample) |
| SK (1) | SK14492003A3 (enExample) |
| TW (1) | TW593235B (enExample) |
| WO (1) | WO2002096862A2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008522969A (ja) * | 2004-12-07 | 2008-07-03 | インヴィスタ テクノロジー エスアエルエル | ジニトリル水素化方法における調節剤の使用 |
| JP2013528603A (ja) * | 2010-05-19 | 2013-07-11 | ビオアンブ，ソシエテ パ アクシオンス シンプリフィエ | ジアミノブタン（ｄａｂ）、コハク酸ジニトリル（ｓｄｎ）及びスクシンアミド（ｄａｍ）を生産する方法 |
| JP2013531624A (ja) * | 2010-05-19 | 2013-08-08 | ビオアンブ，ソシエテ パ アクシオンス シンプリフィエ | ジアミノブタン（ｄａｂ）、コハク酸ジニトリル（ｓｄｎ）及びスクシンアミド（ｄａｍ）を生産する方法 |
| JP2023519281A (ja) * | 2020-03-25 | 2023-05-10 | ベーアーエスエフ・エスエー | ラネーニッケル及び塩基性共触媒の存在下でアジポニトリルの水素化によりヘキサメチレンジアミンを調製する方法 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6569802B1 (en) * | 1999-11-30 | 2003-05-27 | E. I. Du Pont De Nemours And Company | Catalyst for selective hydrogenation of dinitriles |
| US7132562B2 (en) | 2003-11-12 | 2006-11-07 | Invista North America S.A R.L. | Use of modifiers in a dinitrile hydrogenation process |
| DE10361071A1 (de) * | 2003-12-22 | 2005-07-14 | Basf Ag | Nitrilhydrierung in Gegenwart Ionischer Flüssigkeiten |
| DE102006061533A1 (de) * | 2006-12-27 | 2008-07-03 | Saltigo Gmbh | Verfahren zur Herstellung von 2-Aminomethylpiperidin |
| WO2011159557A1 (en) | 2010-06-16 | 2011-12-22 | Bioamber S.A.S. | Processes for producing hexamethylenediamine (hmd), adiponitrile (adn), adipamide (adm) and derivatives thereof |
| JP2013533863A (ja) | 2010-06-16 | 2013-08-29 | ビオアンブ，ソシエテ パ アクシオンス シンプリフィエ | ヘキサメチレンジアミン（ｈｍｄ）、アジポニトリル（ａｄｎ）、アジパミド（ａｄｍ）及びそれらの誘導体の製造方法 |
| WO2012158182A1 (en) | 2011-05-17 | 2012-11-22 | Bioamber S.A.S. | Processes for producing butanediol and diaminobutane from fermentation broths containing ammonium succinates |
| US9464030B2 (en) | 2011-05-18 | 2016-10-11 | Bioamber Inc. | Processes for producing butanediol (BDO), diaminobutane (DAB), succinic dinitrile (SDN) and succinamide (DAM) |
| WO2012170060A1 (en) | 2011-06-10 | 2012-12-13 | Bioamber S.A.S. | Processes for producing hexanediol (hdo), hexamethylenediamine (hmd), and derivatives thereof |
| WO2013149373A1 (zh) * | 2012-04-01 | 2013-10-10 | 烟台万华聚氨酯股份有限公司 | 一种n-(2-氨乙基)-1,2-乙二胺的制备方法 |
| CN105555752A (zh) | 2013-09-13 | 2016-05-04 | 因温斯特技术公司 | 使二腈氢化以便制备二胺 |
| CN105658617A (zh) | 2013-09-13 | 2016-06-08 | 因温斯特技术公司 | 使二腈氢化以便制备二胺 |
| WO2015038679A1 (en) | 2013-09-13 | 2015-03-19 | Invista Technologies S.A R.L. | Catalyst preparation and hydrogenation process |
| WO2015038675A1 (en) | 2013-09-13 | 2015-03-19 | Invista Technologies S.À R.L. | Hydrogenation process for making diamine from dinitrile |
| CN105555753A (zh) | 2013-09-13 | 2016-05-04 | 因温斯特技术公司 | 从二腈制备二胺的氢化方法 |
| CN106536476B (zh) | 2014-04-25 | 2018-11-13 | 英威达纺织（英国）有限公司 | 通过使二腈氢化来制备二胺 |
| WO2015200630A1 (en) | 2014-06-27 | 2015-12-30 | Invista North America S.A R.L. | Integrated process for nitrile manufacture with enhanced liquid-liquid extraction |
| WO2017142898A1 (en) | 2016-02-16 | 2017-08-24 | Invista North America S.A R.L. | Promoter for selective nitrile hydrogenation |
| CN116535321A (zh) * | 2022-01-29 | 2023-08-04 | 北京旭阳科技有限公司 | 壬二腈加氢制备壬二胺的方法 |
| CN117603161A (zh) * | 2023-11-28 | 2024-02-27 | 万华化学集团股份有限公司 | 一种环己亚胺季铵碱、己二腈加氢制备己二胺的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE700877A (enExample) * | 1966-07-04 | 1967-12-18 | ||
| US3773832A (en) * | 1970-01-16 | 1973-11-20 | Du Pont | Hydrogenation of adiponitrile over alkali-modified cobalt catalyst |
| US4721811A (en) | 1985-08-26 | 1988-01-26 | W. R. Grace & Co. | Synthesis of aliphatic polyamines |
| US5900511A (en) | 1997-03-28 | 1999-05-04 | E. I. De Pont De Nemours And Company | Process for continuous hydrogenation of adiponitrile |
| JP2002543057A (ja) * | 1999-04-28 | 2002-12-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アミノニトリルの生成 |
| US6309758B1 (en) | 1999-05-06 | 2001-10-30 | W. R. Grace & Co.-Conn. | Promoted porous catalyst |
-
2001
- 2001-05-31 US US09/871,102 patent/US6376714B1/en not_active Expired - Lifetime
-
2002
- 2002-05-17 TW TW091110365A patent/TW593235B/zh not_active IP Right Cessation
- 2002-05-24 SK SK1449-2003A patent/SK14492003A3/sk not_active Application Discontinuation
- 2002-05-24 MX MXPA03010927A patent/MXPA03010927A/es unknown
- 2002-05-24 BR BR0210082-7A patent/BR0210082A/pt not_active IP Right Cessation
- 2002-05-24 EP EP02739372A patent/EP1392646A2/en not_active Withdrawn
- 2002-05-24 WO PCT/US2002/016374 patent/WO2002096862A2/en not_active Ceased
- 2002-05-24 JP JP2003500042A patent/JP2004534778A/ja not_active Withdrawn
- 2002-05-24 CN CNA028109155A patent/CN1531523A/zh active Pending
- 2002-05-24 CA CA002444442A patent/CA2444442A1/en not_active Abandoned
- 2002-05-24 KR KR20037015547A patent/KR20040004667A/ko not_active Withdrawn
- 2002-05-24 RU RU2003137530/04A patent/RU2003137530A/ru not_active Application Discontinuation
- 2002-05-24 PL PL02364602A patent/PL364602A1/xx unknown
- 2002-05-28 MY MYPI20021949A patent/MY134178A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008522969A (ja) * | 2004-12-07 | 2008-07-03 | インヴィスタ テクノロジー エスアエルエル | ジニトリル水素化方法における調節剤の使用 |
| KR101129878B1 (ko) * | 2004-12-07 | 2012-03-28 | 인비스타 테크놀러지스 에스.에이.알.엘. | 디니트릴 수소화 방법에서의 개질제의 사용 |
| JP2013528603A (ja) * | 2010-05-19 | 2013-07-11 | ビオアンブ，ソシエテ パ アクシオンス シンプリフィエ | ジアミノブタン（ｄａｂ）、コハク酸ジニトリル（ｓｄｎ）及びスクシンアミド（ｄａｍ）を生産する方法 |
| JP2013531624A (ja) * | 2010-05-19 | 2013-08-08 | ビオアンブ，ソシエテ パ アクシオンス シンプリフィエ | ジアミノブタン（ｄａｂ）、コハク酸ジニトリル（ｓｄｎ）及びスクシンアミド（ｄａｍ）を生産する方法 |
| JP2023519281A (ja) * | 2020-03-25 | 2023-05-10 | ベーアーエスエフ・エスエー | ラネーニッケル及び塩基性共触媒の存在下でアジポニトリルの水素化によりヘキサメチレンジアミンを調製する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002096862A2 (en) | 2002-12-05 |
| RU2003137530A (ru) | 2005-04-20 |
| KR20040004667A (ko) | 2004-01-13 |
| PL364602A1 (en) | 2004-12-13 |
| CA2444442A1 (en) | 2002-12-05 |
| TW593235B (en) | 2004-06-21 |
| CN1531523A (zh) | 2004-09-22 |
| US6376714B1 (en) | 2002-04-23 |
| BR0210082A (pt) | 2004-08-17 |
| SK14492003A3 (sk) | 2005-03-04 |
| MXPA03010927A (es) | 2004-02-17 |
| MY134178A (en) | 2007-11-30 |
| EP1392646A2 (en) | 2004-03-03 |
| WO2002096862A3 (en) | 2003-07-31 |
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