JP2011530408A5 - - Google Patents
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- Publication number
- JP2011530408A5 JP2011530408A5 JP2011522611A JP2011522611A JP2011530408A5 JP 2011530408 A5 JP2011530408 A5 JP 2011530408A5 JP 2011522611 A JP2011522611 A JP 2011522611A JP 2011522611 A JP2011522611 A JP 2011522611A JP 2011530408 A5 JP2011530408 A5 JP 2011530408A5
- Authority
- JP
- Japan
- Prior art keywords
- represented
- ruthenium catalyst
- general formula
- heteroaryl
- solvent
- 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
- 239000003054 catalyst Substances 0.000 claims 15
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 12
- 229910052707 ruthenium Inorganic materials 0.000 claims 12
- 238000000034 method Methods 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 4
- -1 alkylheterocyclyl Chemical group 0.000 claims 4
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical compound [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- 150000003138 primary alcohols Chemical class 0.000 claims 2
- 150000003141 primary amines Chemical class 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- WYLYBQSHRJMURN-UHFFFAOYSA-N (2-methoxyphenyl)methanol Chemical compound COC1=CC=CC=C1CO WYLYBQSHRJMURN-UHFFFAOYSA-N 0.000 claims 1
- WZEYZMKZKQPXSX-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1.CC1=CC(C)=CC(C)=C1 WZEYZMKZKQPXSX-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- IIGNZLVHOZEOPV-UHFFFAOYSA-N 3-Methoxybenzyl alcohol Chemical compound COC1=CC=CC(CO)=C1 IIGNZLVHOZEOPV-UHFFFAOYSA-N 0.000 claims 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims 1
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 229910000074 antimony hydride Inorganic materials 0.000 claims 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 150000002527 isonitriles Chemical class 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8770808P | 2008-08-10 | 2008-08-10 | |
| US61/087,708 | 2008-08-10 | ||
| PCT/IL2009/000778 WO2010018570A1 (en) | 2008-08-10 | 2009-08-10 | Process for preparing amines from alcohols and ammonia |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011530408A JP2011530408A (ja) | 2011-12-22 |
| JP2011530408A5 true JP2011530408A5 (enExample) | 2012-08-09 |
| JP5738185B2 JP5738185B2 (ja) | 2015-06-17 |
Family
ID=41259988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011522611A Expired - Fee Related JP5738185B2 (ja) | 2008-08-10 | 2009-08-10 | アルコールおよびアンモニアからアミンを調製する方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US8586742B2 (enExample) |
| EP (1) | EP2307431B1 (enExample) |
| JP (1) | JP5738185B2 (enExample) |
| CN (1) | CN102203108B (enExample) |
| AU (1) | AU2009280778B2 (enExample) |
| CA (1) | CA2732947A1 (enExample) |
| WO (1) | WO2010018570A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004005108A1 (de) | 2004-02-02 | 2005-10-27 | Basf Ag | Verfahren zur Herstellung von Polyisobutenylphenolen |
| DE102011004465A1 (de) * | 2010-09-10 | 2012-03-15 | Evonik Degussa Gmbh | Verfahren zur direkten Aminierung sekundärer Alkohole mit Ammoniak zu primären Aminen |
| EP2629889B1 (en) | 2010-10-19 | 2019-04-03 | Yeda Research and Development Co. Ltd. | Ruthenium complexes and their uses in processes for formation and/or hydrogenation of esters, amides and derivatives thereof |
| DE102011075162A1 (de) * | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Verfahren zur homogen-katalysierte, hochselektiven direkten Aminierung von primären Alkoholen mit Ammoniak zu primären Aminen bei hohem Volumenverhältnis von Flüssig- zu Gasphase und/oder hohen Drücken |
| DE102011003595B4 (de) | 2011-02-03 | 2014-04-17 | Evonik Degussa Gmbh | Herstellung von in ihrer Hauptkette linearen primären Diaminen für Polyamidsynthesen |
| EP2678306B1 (de) | 2011-02-21 | 2017-06-21 | Evonik Degussa GmbH | Verfahren zur direkten aminierung von alkoholen mit ammoniak zu primären aminen mittels eines xantphos katalysatorsystems |
| EP2683707B1 (de) * | 2011-03-08 | 2015-05-13 | Basf Se | Verfahren zur herstellung von alkanolaminen durch homogen-katalysierte alkoholaminierung |
| WO2012119929A1 (de) | 2011-03-08 | 2012-09-13 | Basf Se | Verfahren zur herstellung von di-, tri- und polyaminen durch homogen-katalysierte alkoholaminierung |
| US8785693B2 (en) | 2011-03-08 | 2014-07-22 | Basf Se | Process for the preparation of primary amines by homogeneously catalyzed alcohol amination |
| US8912361B2 (en) | 2011-03-08 | 2014-12-16 | Basf Se | Process for preparing di-, tri- and polyamines by homogeneously catalyzed alcohol amination |
| US9193666B2 (en) * | 2011-03-08 | 2015-11-24 | Basf Se | Process for preparing alkanolamines by homogeneously catalyzed alcohol amination |
| ES2543309T3 (es) * | 2011-03-08 | 2015-08-18 | Basf Se | Procedimiento para la preparación de aminas primarias mediante aminación de alcohol bajo catálisis homogénea |
| AU2012224721A1 (en) * | 2011-03-08 | 2013-10-03 | Basf Se | Method for producing primary amines by means of homogeneously-catalysed alcohol amination |
| US8637709B2 (en) | 2011-03-08 | 2014-01-28 | Basf Se | Process for the preparation of primary amines by homogeneously catalyzed alcohol amination |
| WO2012154945A2 (en) | 2011-05-11 | 2012-11-15 | University Of Florida Research Foundation, Inc. | Ono pincer ligands and ono pincer ligand comprising metal complexes |
| JP6049878B2 (ja) * | 2012-07-23 | 2016-12-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | アニオン性配位子を有しない錯体触媒の存在下でのアンモニアを用いるアルコールの均一系触媒作用によるアミノ化法 |
| US8853400B2 (en) | 2012-07-23 | 2014-10-07 | Basf Se | Process for the homogeneously catalyzed amination of alcohols with ammonia in the presence of a complex catalyst which comprises no anionic ligands |
| CN103626995A (zh) * | 2012-08-21 | 2014-03-12 | 杜邦公司 | 由二醇和二胺制备聚酰胺的方法 |
| WO2015054828A1 (en) * | 2013-10-15 | 2015-04-23 | Rhodia Operations | Process for forming primary, secondary or tertiary amine via direct amination reaction |
| WO2015109452A1 (en) * | 2014-01-22 | 2015-07-30 | Rhodia Operations | Catalyzed amination of alcohols in aqueous medium |
| IL234478A0 (en) | 2014-09-04 | 2014-12-02 | Yeda Res & Dev | Ruthenium complexes and their use for the preparation and/or hydrogenation of esters, amides and their derivatives |
| IL234479A0 (en) | 2014-09-04 | 2014-12-02 | Yeda Res & Dev | A liquid hydrogen storage system based on a catalytic process for the preparation and hydrogenation of a cyclic peptide from 2-aminoethanol and 2-(methylamino)ethanol |
| EP3218350B1 (en) | 2014-11-10 | 2022-01-05 | Rhodia Operations | Process for forming amine by direct amination reaction |
| CN104804048B (zh) * | 2015-05-25 | 2017-09-22 | 洛阳师范学院 | N‑取代苄基氨基膦钳型环钌双膦化合物及其制备方法和应用 |
| DE102015217088B4 (de) * | 2015-09-07 | 2021-01-21 | Volkswagen Aktiengesellschaft | Verfahren zur Herstellung eines Halbzeugs aus einem polyamidhaltigen Verbundwerkstoff und daraus erhaltenes Halbzeug |
| CN107778182B (zh) * | 2016-08-29 | 2020-06-02 | 南京理工大学 | 一种合成n-烷基芳胺的方法 |
| EP3515885B1 (en) * | 2016-09-23 | 2023-12-13 | Umicore Ag & Co. Kg | Preparation of amino acids and amino acid derivatives |
| CN107245066B (zh) * | 2017-06-26 | 2019-10-18 | 浙江大学 | 一种选择性制备糠胺或四氢糠胺的方法 |
| US20240409494A1 (en) * | 2021-10-12 | 2024-12-12 | Huntsman Petrochemical Llc | Method of producing alkoxylated ether amines and uses thereof |
| CN114805259B (zh) * | 2022-05-09 | 2024-01-12 | 厦门大学 | 一种耐失活镍基催化剂上糠醇选择性胺化制备糠胺的方法 |
| JP2023177660A (ja) * | 2022-06-02 | 2023-12-14 | 旭化成株式会社 | ルテニウム錯体の製造方法、並びにルテニウム錯体及びこれを用いたジアミンの製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5912106B2 (ja) * | 1979-02-21 | 1984-03-21 | 花王株式会社 | 脂肪族アミンの製造方法 |
| DE19652350A1 (de) * | 1996-12-17 | 1998-06-18 | Studiengesellschaft Kohle Mbh | Neue Katalysatoren aus Übergangsmetallverbindungen und 4,5-Diphosphinoacridin-Liganden |
| WO2007104357A1 (en) | 2006-03-14 | 2007-09-20 | Jacobs University Bremen Ggmbh | Synthesis of amines with catalytic amounts of mild lewis acids |
| WO2007104359A1 (en) | 2006-03-14 | 2007-09-20 | Jacobs University Bremen Ggmbh | Synthesis of amines with ytterbium lewis acids |
| US8178723B2 (en) * | 2007-10-30 | 2012-05-15 | Yeda Research And Development Co. Ltd. | Process for preparing amides from alcohols and amines |
-
2009
- 2009-08-10 JP JP2011522611A patent/JP5738185B2/ja not_active Expired - Fee Related
- 2009-08-10 CA CA2732947A patent/CA2732947A1/en not_active Abandoned
- 2009-08-10 CN CN200980131089.2A patent/CN102203108B/zh not_active Expired - Fee Related
- 2009-08-10 AU AU2009280778A patent/AU2009280778B2/en not_active Expired - Fee Related
- 2009-08-10 WO PCT/IL2009/000778 patent/WO2010018570A1/en not_active Ceased
- 2009-08-10 EP EP09787521A patent/EP2307431B1/en active Active
- 2009-08-10 US US13/057,989 patent/US8586742B2/en active Active
-
2013
- 2013-10-18 US US14/058,191 patent/US8779136B2/en active Active
-
2014
- 2014-06-05 US US14/297,116 patent/US8889865B2/en active Active
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