CA2526656A1 - 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
- CA2526656A1 CA2526656A1 CA002526656A CA2526656A CA2526656A1 CA 2526656 A1 CA2526656 A1 CA 2526656A1 CA 002526656 A CA002526656 A CA 002526656A CA 2526656 A CA2526656 A CA 2526656A CA 2526656 A1 CA2526656 A1 CA 2526656A1
- Authority
- CA
- Canada
- Prior art keywords
- aminomethyl
- cyclopentylamine
- psi
- palladium
- cyano
- 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.)
- Abandoned
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 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 20
- NSMYBPIHVACKQG-UHFFFAOYSA-N 2-aminocyclopentene-1-carbonitrile Chemical compound NC1=C(C#N)CCC1 NSMYBPIHVACKQG-UHFFFAOYSA-N 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 239000003495 polar organic solvent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 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
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000004971 Cross linker 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
- 239000004952 Polyamide Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 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
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 150000001768 cations Chemical class 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
- -1 extrudates Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- QLNNMIUPRPKARZ-UHFFFAOYSA-N n'-cyclopentylmethanediamine Chemical compound NCNC1CCCC1 QLNNMIUPRPKARZ-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/455,706 | 2003-06-05 | ||
| US10/455,706 US6924394B2 (en) | 2003-06-05 | 2003-06-05 | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine |
| PCT/US2004/007761 WO2004108655A1 (en) | 2003-06-05 | 2004-03-12 | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2526656A1 true CA2526656A1 (en) | 2004-12-16 |
Family
ID=33490004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002526656A Abandoned CA2526656A1 (en) | 2003-06-05 | 2004-03-12 | 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 |
| 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 |
| TWI298318B (en) | 2008-07-01 |
| BRPI0411263A (pt) | 2006-08-01 |
| US6924394B2 (en) | 2005-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |