JP2006526622A5 - - Google Patents
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- Publication number
- JP2006526622A5 JP2006526622A5 JP2006509246A JP2006509246A JP2006526622A5 JP 2006526622 A5 JP2006526622 A5 JP 2006526622A5 JP 2006509246 A JP2006509246 A JP 2006509246A JP 2006509246 A JP2006509246 A JP 2006509246A JP 2006526622 A5 JP2006526622 A5 JP 2006526622A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentylamine
- aminomethyl
- psi
- kpa
- temperature
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 claims description 7
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- NSMYBPIHVACKQG-UHFFFAOYSA-N 2-aminocyclopentene-1-carbonitrile Chemical compound NC1=C(C#N)CCC1 NSMYBPIHVACKQG-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- QLNNMIUPRPKARZ-UHFFFAOYSA-N n'-cyclopentylmethanediamine Chemical compound NCNC1CCCC1 QLNNMIUPRPKARZ-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
Applications Claiming Priority (2)
| 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 |
| PCT/US2004/007761 WO2004108655A1 (en) | 2003-06-05 | 2004-03-12 | Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006526622A JP2006526622A (ja) | 2006-11-24 |
| JP2006526622A5 true JP2006526622A5 (https=) | 2007-04-05 |
Family
ID=33490004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006509246A Pending JP2006526622A (ja) | 2003-06-05 | 2004-03-12 | ２−（アミノメチル）−１−シクロペンチルアミンの低圧製造法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6924394B2 (https=) |
| EP (1) | EP1644315B1 (https=) |
| JP (1) | JP2006526622A (https=) |
| KR (1) | KR101070547B1 (https=) |
| CN (1) | CN100374409C (https=) |
| AT (1) | ATE449755T1 (https=) |
| BR (1) | BRPI0411263A (https=) |
| CA (1) | CA2526656A1 (https=) |
| DE (1) | DE602004024311D1 (https=) |
| MX (1) | MXPA05012942A (https=) |
| TW (1) | TWI298318B (https=) |
| WO (1) | WO2004108655A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2918834C (en) * | 2013-08-21 | 2019-08-20 | 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 EP EP04720471A patent/EP1644315B1/en not_active Expired - Lifetime
- 2004-03-12 MX MXPA05012942A patent/MXPA05012942A/es active IP Right Grant
- 2004-03-12 BR BRPI0411263-6A patent/BRPI0411263A/pt not_active IP Right Cessation
- 2004-03-12 JP JP2006509246A patent/JP2006526622A/ja active Pending
- 2004-03-12 CA CA002526656A patent/CA2526656A1/en not_active Abandoned
- 2004-03-12 KR KR1020057023100A patent/KR101070547B1/ko not_active Expired - Fee Related
- 2004-03-12 AT AT04720471T patent/ATE449755T1/de not_active IP Right Cessation
- 2004-03-12 CN CNB2004800155416A patent/CN100374409C/zh not_active Expired - Fee Related
- 2004-03-12 WO PCT/US2004/007761 patent/WO2004108655A1/en not_active Ceased
- 2004-03-12 DE DE602004024311T patent/DE602004024311D1/de not_active Expired - Lifetime
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