JP2002533319A - 低圧アミン反応器 - Google Patents
低圧アミン反応器Info
- Publication number
- JP2002533319A JP2002533319A JP2000589496A JP2000589496A JP2002533319A JP 2002533319 A JP2002533319 A JP 2002533319A JP 2000589496 A JP2000589496 A JP 2000589496A JP 2000589496 A JP2000589496 A JP 2000589496A JP 2002533319 A JP2002533319 A JP 2002533319A
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- concentration
- nitrile
- item
- local bulk
- 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- Withdrawn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
- 150000001412 amines Chemical class 0.000 title claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- 150000002825 nitriles Chemical class 0.000 claims abstract description 64
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000012429 reaction media Substances 0.000 claims abstract description 26
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 23
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 33
- 238000002156 mixing Methods 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 13
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 10
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical group N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 8
- 230000003068 static effect Effects 0.000 claims description 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 claims description 3
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 2
- 230000009849 deactivation Effects 0.000 description 15
- 239000007788 liquid Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- -1 tallowamine Chemical compound 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003889 chemical engineering Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 102100024522 Bladder cancer-associated protein Human genes 0.000 description 1
- 101150110835 Blcap gene Proteins 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 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
- 101100493740 Oryza sativa subsp. japonica BC10 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000012800 visualization 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11332998P | 1998-12-22 | 1998-12-22 | |
| US60/113,329 | 1998-12-22 | ||
| PCT/US1999/029394 WO2000037424A1 (en) | 1998-12-22 | 1999-12-10 | Low pressure amine reactor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002533319A true JP2002533319A (ja) | 2002-10-08 |
Family
ID=22348829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000589496A Withdrawn JP2002533319A (ja) | 1998-12-22 | 1999-12-10 | 低圧アミン反応器 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6281388B1 (https=) |
| EP (1) | EP1169296A4 (https=) |
| JP (1) | JP2002533319A (https=) |
| KR (1) | KR100676269B1 (https=) |
| CN (1) | CN1216032C (https=) |
| AU (1) | AU770554B2 (https=) |
| BR (1) | BR9916490A (https=) |
| CA (1) | CA2356560A1 (https=) |
| DE (1) | DE1169296T1 (https=) |
| ES (1) | ES2174776T1 (https=) |
| HK (1) | HK1041685A1 (https=) |
| IN (1) | IN221850B (https=) |
| MX (1) | MXPA01006522A (https=) |
| RU (1) | RU2233266C2 (https=) |
| WO (1) | WO2000037424A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US12617750B2 (en) | 2020-03-25 | 2026-05-05 | Basf Se | Process for the preparation of hexamethylenediamine by hydrogenation of adiponitrile in the presence of Raney nickel and a basic co-catalyst |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660887B1 (en) * | 2002-12-23 | 2003-12-09 | Solutia Inc. | Low pressure process for manufacture of 3-dimethylaminopropylamine (DMAPA) |
| RU2326108C2 (ru) * | 2002-12-23 | 2008-06-10 | Солютиа Инк. | Способ производства 3-диметиламинопропиламина (дмапа) при низком давлении |
| US7196223B2 (en) * | 2005-05-03 | 2007-03-27 | Solutia, Inc. | Higher alcohols for solvents in amine production |
| DE102005052457A1 (de) * | 2005-11-03 | 2007-05-10 | Basf Ag | Verfahren zur Synthese von DMAPA |
| RU2434676C9 (ru) * | 2006-03-10 | 2012-12-27 | Басф Се | Катализатор на основе смешанных оксидов для гидрирования органических соединений, способ его получения и способ гидрирования |
| JP5227309B2 (ja) * | 2006-05-09 | 2013-07-03 | ビーエーエスエフ ソシエタス・ヨーロピア | アミノアルキルニトリルおよびそのようなニトリルからのジアミンの製造法 |
| FR2905948B1 (fr) * | 2006-09-19 | 2008-10-24 | Rhodia Recherches & Tech | Procede de fabrication d'amines par hydrogenation de composes nitriles |
| FR2907781B1 (fr) * | 2006-10-27 | 2010-01-08 | Ceca Sa | Procede de synthese de diamines et/ou de triamines primaires de haute purete a partir d'acides dimeres ou trimeres |
| FR2921922B1 (fr) * | 2007-10-04 | 2009-12-04 | Rhodia Operations | Procede de fabrication d'amines par hydrogenation de composes nitriles |
| FR2935704B1 (fr) * | 2008-09-09 | 2010-08-27 | Rhodia Operations | Procede de fabrication d'amines |
| CN103502200B (zh) * | 2011-04-15 | 2016-01-20 | 兰蒂奇化工股份公司 | 用于生产六亚甲基二胺的改进的工艺 |
| JP6671350B2 (ja) * | 2014-08-28 | 2020-03-25 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | コバルト完全接触触媒を使用して第一級アミンを製造する方法 |
| KR102458721B1 (ko) * | 2017-11-29 | 2022-10-26 | 한화솔루션 주식회사 | 프탈레이트 화합물의 수소화 방법 |
| CN111995526A (zh) * | 2020-09-22 | 2020-11-27 | 江苏扬农化工集团有限公司 | 一种固定床加氢合成己二胺的方法 |
| US20240124386A1 (en) | 2022-10-14 | 2024-04-18 | Ascend Performance Materials Operations Llc | Process for producing hexamethylenediamine from caprolactam |
| WO2025119889A1 (en) | 2023-12-07 | 2025-06-12 | Basf Se | Process for manufacturing an aliphatic diamine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3056837A (en) * | 1959-04-24 | 1962-10-02 | Stamicarbon | Process for preparing hexamethylenediamine |
| BE758296A (fr) * | 1969-11-07 | 1971-04-01 | Rhodiatoce | Procede de fabrication d'hexamethylenediamine |
| US4395573A (en) * | 1981-11-23 | 1983-07-26 | Monsanto Company | Production and separation of amines |
| US4491673A (en) * | 1982-04-19 | 1985-01-01 | Monsanto Company | Production and separation of amines |
| FR2722784B3 (fr) * | 1994-07-21 | 1996-09-06 | Rhone Poulenc Chimie | Procede d'hydrogenation catalytique de nitriles en amines en presence d'un catalyseur de type nickel de raney dope |
-
1999
- 1999-12-10 JP JP2000589496A patent/JP2002533319A/ja not_active Withdrawn
- 1999-12-10 RU RU2001120344/04A patent/RU2233266C2/ru not_active IP Right Cessation
- 1999-12-10 ES ES99966130T patent/ES2174776T1/es active Pending
- 1999-12-10 CN CN998162892A patent/CN1216032C/zh not_active Expired - Fee Related
- 1999-12-10 EP EP99966130A patent/EP1169296A4/en not_active Withdrawn
- 1999-12-10 IN IN882CH2001 patent/IN221850B/en unknown
- 1999-12-10 AU AU21746/00A patent/AU770554B2/en not_active Ceased
- 1999-12-10 HK HK02103302.5A patent/HK1041685A1/zh unknown
- 1999-12-10 CA CA002356560A patent/CA2356560A1/en not_active Abandoned
- 1999-12-10 BR BR9916490-6A patent/BR9916490A/pt not_active Application Discontinuation
- 1999-12-10 KR KR20017008123A patent/KR100676269B1/ko not_active Expired - Fee Related
- 1999-12-10 WO PCT/US1999/029394 patent/WO2000037424A1/en not_active Ceased
- 1999-12-10 DE DE1169296T patent/DE1169296T1/de active Pending
- 1999-12-13 US US09/460,051 patent/US6281388B1/en not_active Expired - Fee Related
-
2001
- 2001-06-22 MX MXPA01006522 patent/MXPA01006522A/es not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US12617750B2 (en) | 2020-03-25 | 2026-05-05 | Basf Se | Process for the preparation of hexamethylenediamine by hydrogenation of adiponitrile in the presence of Raney nickel and a basic co-catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| IN2001CH00882A (https=) | 2007-04-27 |
| AU770554B2 (en) | 2004-02-26 |
| CN1216032C (zh) | 2005-08-24 |
| HK1041685A1 (zh) | 2002-07-19 |
| IN221850B (https=) | 2008-09-12 |
| CA2356560A1 (en) | 2000-06-29 |
| MXPA01006522A (es) | 2002-02-01 |
| EP1169296A4 (en) | 2002-11-06 |
| KR20010101316A (ko) | 2001-11-14 |
| WO2000037424A1 (en) | 2000-06-29 |
| MX232905B (https=) | 2005-12-13 |
| ES2174776T1 (es) | 2002-11-16 |
| DE1169296T1 (de) | 2002-08-22 |
| RU2233266C2 (ru) | 2004-07-27 |
| EP1169296A1 (en) | 2002-01-09 |
| BR9916490A (pt) | 2001-12-18 |
| CN1335833A (zh) | 2002-02-13 |
| AU2174600A (en) | 2000-07-12 |
| US6281388B1 (en) | 2001-08-28 |
| KR100676269B1 (ko) | 2007-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20061030 |
|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20080507 |