JP2017521430A5 - - Google Patents
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- Publication number
- JP2017521430A5 JP2017521430A5 JP2017500926A JP2017500926A JP2017521430A5 JP 2017521430 A5 JP2017521430 A5 JP 2017521430A5 JP 2017500926 A JP2017500926 A JP 2017500926A JP 2017500926 A JP2017500926 A JP 2017500926A JP 2017521430 A5 JP2017521430 A5 JP 2017521430A5
- Authority
- JP
- Japan
- Prior art keywords
- amine
- aromatic
- ammonia
- molar ratio
- reaction
- 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.)
- Granted
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 19
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 6
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- -1 aromatic primary amines Chemical class 0.000 claims 3
- 150000003141 primary amines Chemical class 0.000 claims 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- 150000002485 inorganic esters Chemical class 0.000 claims 2
- 150000002895 organic esters Chemical class 0.000 claims 2
- 229940100684 pentylamine Drugs 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000004984 aromatic diamines Chemical class 0.000 claims 1
- XYRAAVXEJMXUOE-UHFFFAOYSA-N azane;4,5,7,9-tetrahydro-3h-purine-2,6,8-trione Chemical compound N.N1C(=O)NC(=O)C2NC(=O)NC21 XYRAAVXEJMXUOE-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 claims 1
- WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 claims 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2014/081945 | 2014-07-10 | ||
| CN2014081945 | 2014-07-10 | ||
| PCT/CN2015/083535 WO2016004867A1 (en) | 2014-07-10 | 2015-07-08 | Process for producing aromatic primary diamines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017521430A JP2017521430A (ja) | 2017-08-03 |
| JP2017521430A5 true JP2017521430A5 (enExample) | 2019-06-27 |
| JP6704896B2 JP6704896B2 (ja) | 2020-06-03 |
Family
ID=55063589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017500926A Active JP6704896B2 (ja) | 2014-07-10 | 2015-07-08 | 芳香族第一級ジアミンの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US10899726B2 (enExample) |
| EP (2) | EP3674285B1 (enExample) |
| JP (1) | JP6704896B2 (enExample) |
| KR (1) | KR20170027792A (enExample) |
| CN (2) | CN106488905B (enExample) |
| BR (1) | BR112017000203B1 (enExample) |
| WO (1) | WO2016004867A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6714072B2 (ja) * | 2016-03-29 | 2020-06-24 | 株式会社日本触媒 | 複素環を有するジアミン化合物の製造方法 |
| WO2018085957A1 (en) | 2016-11-09 | 2018-05-17 | Rhodia Operations | Process for production of aromatic compounds comprising at least two amine functions |
| EP3656766B1 (en) * | 2017-07-21 | 2021-09-15 | Mitsubishi Gas Chemical Company, Inc. | Method for producing 2,5-bis(aminomethyl)furan |
| WO2019073987A1 (ja) * | 2017-10-11 | 2019-04-18 | 三菱瓦斯化学株式会社 | ２，５－ビス（アミノメチル）テトラヒドロフランの製造方法 |
| US20210221782A1 (en) * | 2017-10-11 | 2021-07-22 | Mitsubishi Gas Chemical Company, Inc. | Method for producing 2,5-bis(aminomethyl)tetrahydrofuran |
| CN111097421A (zh) * | 2018-10-29 | 2020-05-05 | 中国科学院大连化学物理研究所 | 负载型金属催化剂及其催化醛类化合物制备伯胺的方法 |
| CN114602461B (zh) * | 2020-12-09 | 2023-04-07 | 中国科学院大连化学物理研究所 | 一种催化二元醛制备二元胺的方法 |
| CN117229239A (zh) * | 2023-08-10 | 2023-12-15 | 中科国生(丽水)新材料科技有限公司 | 一种2,5-呋喃二甲胺的制备方法 |
| CN117645587A (zh) * | 2023-11-28 | 2024-03-05 | 中科国生(杭州)科技有限公司 | 一种2,5-呋喃二甲胺的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2636051A (en) | 1948-04-05 | 1953-04-21 | Shell Dev | Preparation of diamine |
| DE2824423A1 (de) | 1978-06-03 | 1979-12-06 | Ruhrchemie Ag | Verfahren zur herstellung von diaminen |
| JPS60146885A (ja) | 1984-01-06 | 1985-08-02 | Mitsubishi Petrochem Co Ltd | フルフリルアミン及び／又はテトラヒドロフルフリルアミンの製造法 |
| JPS62446A (ja) | 1985-06-25 | 1987-01-06 | Mitsubishi Petrochem Co Ltd | 脂肪芳香族アミンの製造方法 |
| DE3822038A1 (de) | 1988-06-30 | 1990-03-01 | Hoechst Ag | Verfahren zur herstellung von 3(4),8(9)-bis-(aminomethyl)-tricyclo (5.2.1.0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decan |
| DE3917444A1 (de) * | 1989-05-30 | 1991-02-21 | Hoechst Ag | Verfahren zur herstellung von (alpha),(omega)-diaminen |
| JP3001685B2 (ja) | 1991-07-09 | 2000-01-24 | 広栄化学工業株式会社 | ジアミンの製造法 |
| AT399149B (de) | 1993-06-07 | 1995-03-27 | Chemie Linz Gmbh | Verfahren zur herstellung primärer amine aus aldehyden |
| JP3630709B2 (ja) | 1993-12-28 | 2005-03-23 | 株式会社クラレ | 脂肪族ジアミンの製造方法 |
| JPH10130210A (ja) | 1996-10-29 | 1998-05-19 | Kuraray Co Ltd | ジアミンの製造方法 |
| JPH10310559A (ja) | 1997-05-09 | 1998-11-24 | Kuraray Co Ltd | ジアミンの製造方法 |
| CA2419519A1 (en) | 2002-03-27 | 2003-09-27 | Kuraray Co., Ltd. | Process for producing diamines |
| DE102004023529A1 (de) * | 2004-05-13 | 2005-12-08 | Basf Ag | Verfahren zur kontinuierlichen Herstellung eines Amins |
| MX2007016493A (es) * | 2005-06-30 | 2008-03-10 | Dow Global Technologies Inc | Proceso para la aminacion reductora de aldehidos y cetonas a traves de la formacion de intermediarios macrociclicos de poliimina. |
| KR101199716B1 (ko) * | 2006-12-15 | 2012-11-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 알데히드 및 케톤의 환원성 아민화 방법 |
| DE102010030991A1 (de) | 2010-07-06 | 2012-01-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 2,5-Diformylfuran und seiner Derivate |
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2015
- 2015-07-08 KR KR1020177002283A patent/KR20170027792A/ko not_active Withdrawn
- 2015-07-08 CN CN201580037775.9A patent/CN106488905B/zh active Active
- 2015-07-08 EP EP20157956.2A patent/EP3674285B1/en not_active Not-in-force
- 2015-07-08 CN CN201911137833.1A patent/CN111116528B/zh active Active
- 2015-07-08 JP JP2017500926A patent/JP6704896B2/ja active Active
- 2015-07-08 WO PCT/CN2015/083535 patent/WO2016004867A1/en not_active Ceased
- 2015-07-08 US US15/324,932 patent/US10899726B2/en active Active
- 2015-07-08 BR BR112017000203-5A patent/BR112017000203B1/pt active IP Right Grant
- 2015-07-08 EP EP15819072.8A patent/EP3166921B1/en active Active
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2020
- 2020-02-04 US US16/781,356 patent/US11066377B2/en active Active