RU2552619C9 - Способ получения амида карбоновой кислоты из карбонильного соединения и цианистоводородной кислоты - Google Patents
Способ получения амида карбоновой кислоты из карбонильного соединения и цианистоводородной кислоты Download PDFInfo
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- RU2552619C9 RU2552619C9 RU2011126760/04A RU2011126760A RU2552619C9 RU 2552619 C9 RU2552619 C9 RU 2552619C9 RU 2011126760/04 A RU2011126760/04 A RU 2011126760/04A RU 2011126760 A RU2011126760 A RU 2011126760A RU 2552619 C9 RU2552619 C9 RU 2552619C9
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- Prior art keywords
- acid
- stage
- mixture
- ketone
- hydrocyanic
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- 238000000034 method Methods 0.000 title claims abstract description 65
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 238000005342 ion exchange Methods 0.000 description 1
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- 229910002096 lithium permanganate Inorganic materials 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
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- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
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- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940094037 potassium bromate Drugs 0.000 description 1
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- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical class [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
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- 229910001415 sodium ion Inorganic materials 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
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- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C07C231/065—By hydration using metals or metallic ions as catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| PCT/EP2009/064279 WO2010063520A1 (de) | 2008-12-01 | 2009-10-29 | Verfahren zur herstellung von einem carbonsäureamid aus einer carbonylverbindung und blausäure |
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| MX2008014641A (es) * | 2006-05-15 | 2008-11-27 | Evonik Roehm Gmbh | Proceso para preparar esteres alfa-hidroxicarboxilicos. |
| DE102006055428A1 (de) * | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von (Meth)acrylsäure |
| DE102006055430A1 (de) | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Carbonsäureamiden durch Hydrolyse von Carbonsäurenitrilen in Gegenwart eines Mangandioxid umfassenden Katalysators |
| DE102008001319A1 (de) * | 2008-04-22 | 2009-10-29 | Evonik Röhm Gmbh | Katalysator zur Umsetzung von Carbonsäurenitrilen |
| BR112013018092B1 (pt) | 2011-02-23 | 2021-04-27 | Evonik Operations Gmbh | Método para produção de 2-hidróxi-4-(metiltio) butano nitrila a partir de 3- (metiltio) propanal e cianeto de hidrogênio, e uso de um produto de reação, que contém mmp-cianidrina |
| CN102295571B (zh) * | 2011-06-01 | 2016-04-27 | 郭建行 | 甲醇或甲醛氨氧化合成酰胺的方法 |
| US10227284B2 (en) | 2014-09-10 | 2019-03-12 | Evonik Roehm Gmbh | Method for preparing alpha-hydroxycarboxylic acid esters in which ammonia is recycled |
| DE102016210285A1 (de) | 2016-06-10 | 2017-12-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylaten und Methacrylsäure |
| EP3392237B1 (de) | 2017-04-21 | 2019-10-02 | Evonik Degussa GmbH | Verfahren zur herstellung von acroleincyanhydrinen |
| EP3604222A1 (en) * | 2018-07-30 | 2020-02-05 | Evonik Operations GmbH | Process for the purification of hydrogen cyanide |
| CN112495391B (zh) * | 2020-12-21 | 2021-09-14 | 中国科学院山西煤炭化学研究所 | 一种适用于乙腈水合反应制备乙酰胺的负载型复合金属催化剂及其制备方法和应用 |
| US12492133B2 (en) * | 2021-11-17 | 2025-12-09 | Lg Chem, Ltd. | Method for purifying of waste water |
| EP4452919A1 (de) | 2021-12-23 | 2024-10-30 | Röhm GmbH | Verfahren zur herstellung von alkylmethacrylaten mit verbesserter ausbeute und verminderten emissionen flüchtiger organischer verbindungen |
| WO2023169810A1 (de) | 2022-03-11 | 2023-09-14 | Röhm Gmbh | Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie |
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| SU486506A3 (ru) * | 1969-10-21 | 1975-09-30 | Нитто Кагаку Кошо Кабусики Кайся (Фирма) | Способ получени ацетонциангидрина |
| EP0407811A2 (en) * | 1989-07-14 | 1991-01-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing methyl methacrylate |
| JP2002371046A (ja) * | 2001-06-11 | 2002-12-26 | Showa Denko Kk | ２−ヒドロキシカルボン酸アミドの製法 |
| DE102006055430A1 (de) * | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Carbonsäureamiden durch Hydrolyse von Carbonsäurenitrilen in Gegenwart eines Mangandioxid umfassenden Katalysators |
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| US3562320A (en) | 1967-04-25 | 1971-02-09 | Escambia Chem Corp | Process for producing methacrylic acid |
| DE2202660C3 (de) * | 1972-01-20 | 1983-12-29 | Skw Trostberg Ag, 8223 Trostberg | Verfahren zur Entfernung von Cyanidionen aus Abwasser |
| DE2527120A1 (de) | 1975-06-18 | 1976-12-30 | Roehm Gmbh | Verfahren zur herstellung von alpha-hydroxyisobutyramid aus acetoncyanhydrin |
| US4950801A (en) | 1989-01-19 | 1990-08-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing alpha-hydroxycarboxylic acid amide |
| JP2893730B2 (ja) | 1989-07-04 | 1999-05-24 | 三菱瓦斯化学株式会社 | メタクリル酸メチルの製造法 |
| JP2780373B2 (ja) * | 1989-09-07 | 1998-07-30 | 三菱瓦斯化学株式会社 | α―ヒドロキシカルボン酸アミドの製造法 |
| JP2827368B2 (ja) | 1989-12-19 | 1998-11-25 | 三菱瓦斯化学株式会社 | α―ヒドロキシイソ酪酸アミドの製造法 |
| US5387715A (en) | 1991-12-03 | 1995-02-07 | Mitsui Toatsu Chemicals, Inc. | Process for producing α-hydroxy-isobutyramide |
| JPH06172283A (ja) | 1992-12-02 | 1994-06-21 | Mitsui Toatsu Chem Inc | α−ヒドロキシイソ酪酸アミドの製造方法 |
| KR960000850A (ko) | 1994-06-06 | 1996-01-25 | 사토 아키오 | 메타크릴산메틸의 연속제조방법 |
| GB9719060D0 (en) | 1997-09-09 | 1997-11-12 | Ici Plc | Polymer composition |
| JPH11255710A (ja) | 1998-03-11 | 1999-09-21 | Mitsubishi Gas Chem Co Inc | メタクリル酸メチルの製造方法 |
| JPH11319558A (ja) | 1998-05-13 | 1999-11-24 | Mitsubishi Gas Chem Co Inc | シアンヒドリンの水和触媒 |
| DE102005023975A1 (de) * | 2005-05-20 | 2006-11-23 | Röhm Gmbh | Verfahren zur Herstellung von Alkyl(meth)acrylaten |
| DE102005023976A1 (de) | 2005-05-20 | 2006-11-23 | Röhm Gmbh | Verfahren zur Umesterung |
| MX2008014641A (es) | 2006-05-15 | 2008-11-27 | Evonik Roehm Gmbh | Proceso para preparar esteres alfa-hidroxicarboxilicos. |
| DE102007011706A1 (de) * | 2007-03-08 | 2008-09-11 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Alpha-Hydroxycarbonsäuren |
| DE102006055427A1 (de) | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Tetramethylglycolid |
| DE102006055428A1 (de) | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von (Meth)acrylsäure |
| DE102006055426A1 (de) | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Alkyl(meth)acrylaten unter Verwendung einer enzymatischen Cyanhydrinhydrolyse |
| DE102008001319A1 (de) | 2008-04-22 | 2009-10-29 | Evonik Röhm Gmbh | Katalysator zur Umsetzung von Carbonsäurenitrilen |
-
2008
- 2008-12-01 DE DE102008044218A patent/DE102008044218A1/de not_active Withdrawn
-
2009
- 2009-10-29 EP EP09751855.9A patent/EP2352720B1/de not_active Not-in-force
- 2009-10-29 JP JP2011538919A patent/JP5757874B2/ja not_active Expired - Fee Related
- 2009-10-29 CN CN200980148070.9A patent/CN102232064B/zh not_active Expired - Fee Related
- 2009-10-29 WO PCT/EP2009/064279 patent/WO2010063520A1/de not_active Ceased
- 2009-10-29 CA CA2745498A patent/CA2745498A1/en not_active Abandoned
- 2009-10-29 RU RU2011126760/04A patent/RU2552619C9/ru not_active IP Right Cessation
- 2009-10-29 KR KR1020117012447A patent/KR101696940B1/ko not_active Expired - Fee Related
- 2009-10-29 MY MYPI2011002496A patent/MY159638A/en unknown
- 2009-10-29 MX MX2011005476A patent/MX2011005476A/es not_active Application Discontinuation
- 2009-10-29 SG SG2011039518A patent/SG171871A1/en unknown
- 2009-10-29 BR BRPI0922626A patent/BRPI0922626A2/pt not_active Application Discontinuation
- 2009-10-29 US US13/131,462 patent/US8975440B2/en not_active Expired - Fee Related
- 2009-11-26 TW TW98140350A patent/TWI471291B/zh not_active IP Right Cessation
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| SU486506A3 (ru) * | 1969-10-21 | 1975-09-30 | Нитто Кагаку Кошо Кабусики Кайся (Фирма) | Способ получени ацетонциангидрина |
| EP0407811A2 (en) * | 1989-07-14 | 1991-01-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing methyl methacrylate |
| JP2002371046A (ja) * | 2001-06-11 | 2002-12-26 | Showa Denko Kk | ２−ヒドロキシカルボン酸アミドの製法 |
| DE102006055430A1 (de) * | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Carbonsäureamiden durch Hydrolyse von Carbonsäurenitrilen in Gegenwart eines Mangandioxid umfassenden Katalysators |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2011005476A (es) | 2011-06-16 |
| JP5757874B2 (ja) | 2015-08-05 |
| EP2352720A1 (de) | 2011-08-10 |
| TW201031622A (en) | 2010-09-01 |
| KR101696940B1 (ko) | 2017-01-16 |
| TWI471291B (zh) | 2015-02-01 |
| WO2010063520A9 (de) | 2011-06-03 |
| CA2745498A1 (en) | 2010-06-10 |
| KR20110090993A (ko) | 2011-08-10 |
| JP2012510485A (ja) | 2012-05-10 |
| RU2552619C2 (ru) | 2015-06-10 |
| CN102232064A (zh) | 2011-11-02 |
| SG171871A1 (en) | 2011-07-28 |
| US20110306784A1 (en) | 2011-12-15 |
| EP2352720B1 (de) | 2017-12-20 |
| RU2011126760A (ru) | 2013-01-10 |
| WO2010063520A1 (de) | 2010-06-10 |
| US20120232305A2 (en) | 2012-09-13 |
| DE102008044218A1 (de) | 2010-06-02 |
| US8975440B2 (en) | 2015-03-10 |
| CN102232064B (zh) | 2014-11-05 |
| BRPI0922626A2 (pt) | 2016-01-05 |
| MY159638A (en) | 2017-01-13 |
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| TH4A | Reissue of patent specification | ||
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20181030 |