TWI298318B - Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine - Google Patents
Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine Download PDFInfo
- Publication number
- TWI298318B TWI298318B TW093105903A TW93105903A TWI298318B TW I298318 B TWI298318 B TW I298318B TW 093105903 A TW093105903 A TW 093105903A TW 93105903 A TW93105903 A TW 93105903A TW I298318 B TWI298318 B TW I298318B
- Authority
- TW
- Taiwan
- Prior art keywords
- aminomethyl
- catalyst
- cyclopentylamine
- temperature
- psi
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 45
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
- 239000003495 polar organic solvent Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- -1 2-(aminomethyl)-indole-cyclopentylamine Chemical compound 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229940100684 pentylamine Drugs 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 13
- NSMYBPIHVACKQG-UHFFFAOYSA-N 2-aminocyclopentene-1-carbonitrile Chemical compound NC1=C(C#N)CCC1 NSMYBPIHVACKQG-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- XBVZRFXCDCYXAX-UHFFFAOYSA-N cyclopentene-1-carbonitrile Chemical compound N#CC1=CCCC1 XBVZRFXCDCYXAX-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QLNNMIUPRPKARZ-UHFFFAOYSA-N n'-cyclopentylmethanediamine Chemical compound NCNC1CCCC1 QLNNMIUPRPKARZ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/455,706 US6924394B2 (en) | 2003-06-05 | 2003-06-05 | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200510275A TW200510275A (en) | 2005-03-16 |
| TWI298318B true TWI298318B (en) | 2008-07-01 |
Family
ID=33490004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093105903A TWI298318B (en) | 2003-06-05 | 2004-03-05 | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6924394B2 (enExample) |
| EP (1) | EP1644315B1 (enExample) |
| JP (1) | JP2006526622A (enExample) |
| KR (1) | KR101070547B1 (enExample) |
| CN (1) | CN100374409C (enExample) |
| AT (1) | ATE449755T1 (enExample) |
| BR (1) | BRPI0411263A (enExample) |
| CA (1) | CA2526656A1 (enExample) |
| DE (1) | DE602004024311D1 (enExample) |
| MX (1) | MXPA05012942A (enExample) |
| TW (1) | TWI298318B (enExample) |
| WO (1) | WO2004108655A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015027043A1 (en) * | 2013-08-21 | 2015-02-26 | Gi-Gasification International (Luxembourg), S.A. | Methods, systems, and apparatuses for low-temperature fischer-tropsch wax hydrogenation |
| CN115433095B (zh) * | 2021-06-01 | 2023-08-11 | 万华化学集团股份有限公司 | 一种环己胺衍生物及制备方法、一种环氧树脂组合物及制备方法和应用 |
| CN114835588B (zh) * | 2022-05-06 | 2023-05-26 | 万华化学集团股份有限公司 | 一种双氰乙基脂环胺加氢制备双氨丙基脂环胺的方法 |
| CN116178170B (zh) * | 2022-12-07 | 2025-02-18 | 万华化学集团股份有限公司 | 一种2-氨甲基环戊基胺的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2292949A (en) * | 1940-09-13 | 1942-08-11 | Du Pont | Process for catalytic hydrogenation |
| BE792649A (fr) * | 1971-12-13 | 1973-06-12 | Rhone Poulenc Sa | Catalyseur a base de nickel raney au fer |
| JP2001500139A (ja) * | 1996-09-10 | 2001-01-09 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘキサメチレンジアミンと２―アミノメチルシクロペンチルアミンとを含む混合物からの２―アミノメチルシクロペンチルアミンの分離 |
| DE19839338A1 (de) * | 1998-08-28 | 2000-03-02 | Basf Ag | Verbessertes Verfahren zur gleizeitigen Herstellung von 6-Aminocapronitril und Hexamethylendiamin |
-
2003
- 2003-06-05 US US10/455,706 patent/US6924394B2/en not_active Expired - Fee Related
-
2004
- 2004-03-05 TW TW093105903A patent/TWI298318B/zh not_active IP Right Cessation
- 2004-03-12 CA CA002526656A patent/CA2526656A1/en not_active Abandoned
- 2004-03-12 AT AT04720471T patent/ATE449755T1/de not_active IP Right Cessation
- 2004-03-12 WO PCT/US2004/007761 patent/WO2004108655A1/en not_active Ceased
- 2004-03-12 EP EP04720471A patent/EP1644315B1/en not_active Expired - Lifetime
- 2004-03-12 MX MXPA05012942A patent/MXPA05012942A/es active IP Right Grant
- 2004-03-12 DE DE602004024311T patent/DE602004024311D1/de not_active Expired - Lifetime
- 2004-03-12 KR KR1020057023100A patent/KR101070547B1/ko not_active Expired - Fee Related
- 2004-03-12 BR BRPI0411263-6A patent/BRPI0411263A/pt not_active IP Right Cessation
- 2004-03-12 CN CNB2004800155416A patent/CN100374409C/zh not_active Expired - Fee Related
- 2004-03-12 JP JP2006509246A patent/JP2006526622A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060017528A (ko) | 2006-02-23 |
| JP2006526622A (ja) | 2006-11-24 |
| CN1798727A (zh) | 2006-07-05 |
| ATE449755T1 (de) | 2009-12-15 |
| DE602004024311D1 (de) | 2010-01-07 |
| US20040249214A1 (en) | 2004-12-09 |
| WO2004108655A1 (en) | 2004-12-16 |
| CN100374409C (zh) | 2008-03-12 |
| CA2526656A1 (en) | 2004-12-16 |
| MXPA05012942A (es) | 2006-02-13 |
| TW200510275A (en) | 2005-03-16 |
| EP1644315A1 (en) | 2006-04-12 |
| EP1644315B1 (en) | 2009-11-25 |
| KR101070547B1 (ko) | 2011-10-05 |
| BRPI0411263A (pt) | 2006-08-01 |
| US6924394B2 (en) | 2005-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100553283B1 (ko) | 알파-,오메가-디니트릴을 수소화하는 철을 기재로 한 촉매 | |
| JP2004516308A (ja) | ニトリルおよびイミンの水素化により第一級および第二級アミンを製造する方法 | |
| JP2018008933A (ja) | ２−（３−（アミノメチル）−３，５，５−トリメチルシクロヘキシル）プロパン−１，３−ジアミン、その製造方法、および使用 | |
| JP2018008931A (ja) | ２−（３，３，５−トリメチルシクロヘキシル）プロパン−１，３−ジアミン、その製造方法、およびその使用 | |
| JP2004534778A (ja) | ジニトリルの環境調和型水素化プロセス | |
| US8415500B2 (en) | One-stage reductive amination | |
| TWI298318B (en) | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine | |
| KR20110086058A (ko) | 1,2-디아미노시클로헥산 및 화학적 방법 | |
| CN110078627B (zh) | 一种高收率合成h6mda的方法 | |
| RU2181358C2 (ru) | Способ получения сертралина из хирального тетралона | |
| EP1449825A1 (en) | High-selective production method of di(aminomethyl)-substituted aromatic compound | |
| JP5767220B2 (ja) | １つ又はそれ以上の脂肪族ジアミンを還元的アミノ化反応溶媒及び不純物から分離する方法 | |
| JP3528970B2 (ja) | シアノ基含有芳香族メチルアミンの製造方法 | |
| JPH09227468A (ja) | シクロヘキシルアミンおよびジシクロヘキシルアミンの混合物の製造法 | |
| JP3920524B2 (ja) | ビストリフルオロメチルベンジルアミン類の製造方法 | |
| JPWO1998033767A1 (ja) | シアノ基含有芳香族メチルアミンの製造方法 | |
| JP2006526622A5 (enExample) | ||
| CN115193436B (zh) | 一种镍钴金属骨架催化剂、制备方法及其应用 | |
| KR100722981B1 (ko) | 촉매 수소화 반응에 의한 트란스-4-메틸시클로헥실아민의제조방법 | |
| JPS6246535B2 (enExample) | ||
| JPH10204048A (ja) | 芳香族シアノメチルアミンの製造方法 | |
| JPS60260544A (ja) | １，４−ジアミノブタンの製造方法 | |
| JP4147809B2 (ja) | ハロゲン化芳香族メチルアミン類の製造方法 | |
| JPH0585991A (ja) | ３−アミノメチル−３，５，５−トリアルキルシクロヘキシルアミンの製造法 | |
| JPS59190975A (ja) | ２−アルキル−４−アミノ−５−アミノメチルピリミジンの製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |