RU2014107102A - METHOD FOR PRODUCING FORMAMIDES AND COMPOUND ETHERS OF FORMIC ACID - Google Patents

METHOD FOR PRODUCING FORMAMIDES AND COMPOUND ETHERS OF FORMIC ACID Download PDF

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RU2014107102A
RU2014107102A RU2014107102/04A RU2014107102A RU2014107102A RU 2014107102 A RU2014107102 A RU 2014107102A RU 2014107102/04 A RU2014107102/04 A RU 2014107102/04A RU 2014107102 A RU2014107102 A RU 2014107102A RU 2014107102 A RU2014107102 A RU 2014107102A
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cycloalkyl
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amine
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Томас ШАУБ
Рокко ПАСИЭЛЛО
Марек ПАЗИЦКИ
Джузеппе ФАКИНЕТТИ
Дебора ПРЕТИ
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Басф Се
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Abstract

1. Способ получения производных карбоновой кислоты общей формулы (Ia)в которойR выбран из группы, включающей ORи NRR, причем Rпредставляет собой незамещенные или, по меньшей мере, монозамещенные С-С-алкил, С-С-циклоалкил, С-С-гетероциклил, С-С-арил или С-С-гетероарил, причем заместители выбраны из группы, включающей С-С-алкил, С-С-алкокси, С-С-циклоалкил и С-С-арил,Rи Rозначают независимо друг от друга водород, незамещенные или, по меньшей мере, монозамещенные С-С-алкил, С-С-циклоалкил, С-С-гетероциклил, С-С-арил или С-С-гетероарил, причем заместители выбраны из группы, включающей С-С-алкил, С-С-циклоалкил и С-С-арил, илиRи Rвместе с атомом азота образуют пяти- или шестичленное кольцо, которое дополнительно может содержать один или несколько гетероатомов, выбранных из О, S и N, и несущих заместитель R, который означает водород или С-С-алкил;посредством превращения реакционной смеси (Rg), содержащей двуокись углерода, водород и спирт, общей формулы (Ib)в которой Rимеет вышеприведенные значенияилиамин общей формулы (Ic)в которой Rи Rнезависимо друг от друга имеют вышеприведенные значения, в реакторе гидрирования в присутствии катализатора, содержащего золото, при давлении в диапазоне от 0,2 до 30 МПа и температуре в диапазоне от 20 до 200°С.2. Способ по п. 1, причем катализатор является гетерогенным катализатором.3. Способ по п. 1, причем катализатор содержит, по меньшей мере, один носитель4. Способ по п. 3, причем носитель выбран из группы, состоящей из двуокиси кремния, окиси алюминия, окиси циркония, окиси магния и окиси титана.5. Способ по п. 3, причем гетерогенный катализатор содержит от 0,1 до 20 вес.% золота, в пересчете на общую массу используемого кат�1. A method for preparing carboxylic acid derivatives of general formula (Ia) in which R is selected from the group consisting of OR and NRR, and R represents unsubstituted or at least monosubstituted C-C-alkyl, C-C-cycloalkyl, C-C-heterocyclyl , C-C-aryl or C-C-heteroaryl, wherein the substituents are selected from the group consisting of C-C-alkyl, C-C-alkoxy, C-C-cycloalkyl and C-C-aryl, R and R are independently of each other hydrogen, unsubstituted or at least monosubstituted C-C-alkyl, C-C-cycloalkyl, C-C-heterocyclyl, C-C-aryl or C-C-heteroaryl, wherein the substituents are selected from the group consisting of C-C -alkyl, C-C-cycloalkyl and C-C-aryl, or R and R, together with a nitrogen atom, form a five- or six-membered ring, which may additionally contain one or more heteroatoms selected from O, S and N, and bearing the substituent R, which means hydrogen or C-C-alkyl; by converting a reaction mixture (Rg) containing carbon dioxide, hydrogen and alcohol, of the general formula (Ib) in which R has the above meanings or an amine of the general formula (Ic) in which R and R, independently of each other, have the above meanings , in a hydrogenation reactor in the presence of a catalyst containing gold, at a pressure in the range from 0.2 to 30 MPa and a temperature in the range from 20 to 200°C.2. The method according to claim 1, wherein the catalyst is a heterogeneous catalyst.3. The method according to claim 1, wherein the catalyst contains at least one carrier4. The method according to claim 3, wherein the carrier is selected from the group consisting of silicon dioxide, alumina, zirconium oxide, magnesium oxide and titanium oxide. The method according to claim 3, wherein the heterogeneous catalyst contains from 0.1 to 20 wt.% gold, based on the total weight of the cat used.

Claims (14)

1. Способ получения производных карбоновой кислоты общей формулы (Ia)1. The method of obtaining derivatives of carboxylic acids of General formula (Ia)
Figure 00000001
Figure 00000001
 в которойwherein R выбран из группы, включающей OR1 и NR2R3, причем R1 представляет собой незамещенные или, по меньшей мере, монозамещенные С1-С15-алкил, С5-С10-циклоалкил, С5-С10-гетероциклил, С5-С10-арил или С5-С10-гетероарил, причем заместители выбраны из группы, включающей С1-С15-алкил, С1-С6-алкокси, С5-С10-циклоалкил и С5-С10-арил,R is selected from the group consisting of OR 1 and NR 2 R 3 , wherein R 1 is unsubstituted or at least monosubstituted C 1 -C 15 alkyl, C 5 -C 10 cycloalkyl, C 5 -C 10 heterocyclyl , C 5 -C 10 aryl or C 5 -C 10 heteroaryl, with the substituents selected from the group consisting of C 1 -C 15 alkyl, C 1 -C 6 alkoxy, C 5 -C 10 cycloalkyl and C 5 -C 10 aryl, R2 и R3 означают независимо друг от друга водород, незамещенные или, по меньшей мере, монозамещенные С1-С15-алкил, С5-С10-циклоалкил, С5-С10-гетероциклил, С5-С10-арил или С5-С10-гетероарил, причем заместители выбраны из группы, включающей С1-С15-алкил, С5-С10-циклоалкил и С5-С10-арил, илиR 2 and R 3 mean independently hydrogen, unsubstituted or at least monosubstituted C 1 -C 15 alkyl, C 5 -C 10 cycloalkyl, C 5 -C 10 heterocyclyl, C 5 -C 10 - aryl or C 5 -C 10 heteroaryl, wherein the substituents are selected from the group consisting of C 1 -C 15 alkyl, C 5 -C 10 cycloalkyl and C 5 -C 10 aryl, or R2 и R3 вместе с атомом азота образуют пяти- или шестичленное кольцо, которое дополнительно может содержать один или несколько гетероатомов, выбранных из О, S и N, и несущих заместитель R4, который означает водород или С1-С6-алкил;R 2 and R 3 together with the nitrogen atom form a five- or six-membered ring, which may additionally contain one or more heteroatoms selected from O, S and N, and bearing a substituent R 4 , which means hydrogen or C 1 -C 6 -alkyl ; посредством превращения реакционной смеси (Rg), содержащей двуокись углерода, водород и спирт, общей формулы (Ib)by converting a reaction mixture (Rg) containing carbon dioxide, hydrogen and alcohol of the general formula (Ib)
Figure 00000002
Figure 00000002
 в которой R1 имеет вышеприведенные значенияin which R 1 has the above meanings илиor амин общей формулы (Ic)amine of the general formula (Ic)
Figure 00000003
Figure 00000003
 в которой R2 и R3 независимо друг от друга имеют вышеприведенные значения, в реакторе гидрирования в присутствии катализатора, содержащего золото, при давлении в диапазоне от 0,2 до 30 МПа и температуре в диапазоне от 20 до 200°С.in which R 2 and R 3 independently from each other have the above values, in a hydrogenation reactor in the presence of a catalyst containing gold, at a pressure in the range from 0.2 to 30 MPa and a temperature in the range from 20 to 200 ° C. 2. Способ по п. 1, причем катализатор является гетерогенным катализатором.2. The method of claim 1, wherein the catalyst is a heterogeneous catalyst. 3. Способ по п. 1, причем катализатор содержит, по меньшей мере, один носитель3. The method according to p. 1, and the catalyst contains at least one carrier 4. Способ по п. 3, причем носитель выбран из группы, состоящей из двуокиси кремния, окиси алюминия, окиси циркония, окиси магния и окиси титана.4. The method of claim 3, wherein the carrier is selected from the group consisting of silica, alumina, zirconia, magnesium oxide and titanium oxide. 5. Способ по п. 3, причем гетерогенный катализатор содержит от 0,1 до 20 вес.% золота, в пересчете на общую массу используемого катализатора на носителе.5. The method according to claim 3, wherein the heterogeneous catalyst contains from 0.1 to 20 wt.% Gold, calculated on the total weight of the supported catalyst used. 6. Способ по п. 1, причем используют спирт общей формулы (Ib), в которой R1 является незамещенным или по меньшей мере монозамещенным С1-С8-алкилом, причем заместители выбраны из группы, состоящей из С1-С6-алкила и С1-С6-алкокси.6. The method according to claim 1, wherein an alcohol of the general formula (Ib) is used, in which R 1 is unsubstituted or at least monosubstituted with C 1 -C 8 alkyl, with the substituents selected from the group consisting of C 1 -C 6 - alkyl and C 1 -C 6 alkoxy. 7. Способ по п. 6, причем в качестве спирта (Ib) используют спирт, выбранный из группы, включащей метанол, этанол, 2-метоксиэтанол, 1-пропанол, 2-пропанол, 1-бутанол, 2-бутанол, 2-метил-1-пропанол, 1-пентанол, 1-гексанол, 1-гептанол и 1-октанол.7. The method according to claim 6, wherein the alcohol (Ib) is an alcohol selected from the group consisting of methanol, ethanol, 2-methoxyethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl -1-propanol, 1-pentanol, 1-hexanol, 1-heptanol and 1-octanol. 8. Способ по п. 6, причем в качестве спирта (Ib) используют метанол с получением в качестве производного карбоновой кислоты (Ia) метилформиата.8. The method according to claim 6, wherein methanol is used as the alcohol (Ib) to obtain methyl formate as the carboxylic acid derivative (Ia). 9. Способ по п. 1, причем в качестве амина (Ic) используют амин, выбранный из группы, включающей аммиак, метиламин, диметиламин, этиламин, диэтиламин, n-пропиламин, ди-n-пропиламин, изопропиламин, диизопропиламин, n-бутиламин, ди-n-бутиламин, изобутиламин, диизобутиламин, морфолин, пиперидин и пиперазин.9. The method of claim 1, wherein the amine (Ic) is an amine selected from the group consisting of ammonia, methylamine, dimethylamine, ethylamine, diethylamine, n-propylamine, di-n-propylamine, isopropylamine, diisopropylamine, n-butylamine , di-n-butylamine, isobutylamine, diisobutylamine, morpholine, piperidine and piperazine. 10. Способ по п. 9, причем в качестве амина (Ic) используют амин, выбранный из группы, включающей аммиак, метиламин и диметиламин.10. The method of claim 9, wherein the amine (Ic) is an amine selected from the group consisting of ammonia, methylamine and dimethylamine. 11. Способ по п. 9, причем в качестве амина (Ic) используют аммиак с получением в качестве производного карбоновой кислоты (Ia) формамида.11. The method according to claim 9, wherein ammonia is used as an amine (Ic) to formamide as a carboxylic acid derivative (Ia). 12. Способ по одному из пп. 1-11, причем время пребывания реакционной смеси (Rg) в реакторе гидрирования составляет от 10 минут до 5 часов.12. The method according to one of paragraphs. 1-11, and the residence time of the reaction mixture (Rg) in the hydrogenation reactor is from 10 minutes to 5 hours. 13. Способ по п. 12, причем полученную в результате реакции смесь перерабатывают в дистилляционном устройстве с получением первого потока, содержащего производное карбоновой кислоты (Ia),13. The method according to p. 12, and the resulting reaction mixture is processed in a distillation device to obtain a first stream containing a carboxylic acid derivative (Ia), второго потока, содержащего непрореагировавший спирт (Ib) или непрореагировавший амин (Ic), иa second stream containing unreacted alcohol (Ib) or unreacted amine (Ic), and третьего потока, содержащего образовавшуюся при реакции реакционную воду.a third stream containing reaction water formed during the reaction. 14. Способ по п. 13, причем второй поток возвращают в реактор гидрирования. 14. The method of claim 13, wherein the second stream is returned to the hydrogenation reactor.
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Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015121357A1 (en) * 2014-02-17 2015-08-20 Bayer Technology Services Gmbh Method for hydrogenating carbon dioxide into formamides
WO2015192282A1 (en) * 2014-06-16 2015-12-23 Rhodia Operations Formylation process for preparing aromatic formamides
CN105373135B (en) * 2014-08-01 2019-01-01 深圳中集天达空港设备有限公司 A kind of method and system of aircraft docking guidance and plane type recognition based on machine vision
CN105985254B (en) * 2015-02-17 2018-03-16 上海中科绿碳化工科技有限公司 A kind of method for preparing Carbox amide
US10435349B2 (en) * 2017-08-02 2019-10-08 Eastman Chemical Company Iron-catalyzed cross-coupling of methanol with secondary or tertiary alcohols to produce formate esters
CN107915653B (en) * 2017-12-04 2020-02-14 苏州大学 Method for preparing amide by catalyzing ester and amine to react
CN108623493B (en) * 2018-06-20 2021-01-19 大连理工大学 Under mild condition with CO2N-formylation synthesis method for carbon source
DE102019111058A1 (en) * 2019-04-29 2020-10-29 Rheinisch-Westfälische Technische Hochschule (Rwth) Aachen Process for the catalytic production of urea
CN113979882A (en) * 2021-11-29 2022-01-28 宿迁新亚科技有限公司 Production process for preparing dibutyl formamide

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51138614A (en) * 1975-05-27 1976-11-30 Mitsubishi Gas Chem Co Inc Process for preparation of formic acid and its este r
US4269998A (en) 1980-02-19 1981-05-26 Uop Inc. Production of dialkyl formamide
DK0652202T3 (en) * 1993-11-04 1997-12-22 Japan Res Dev Corp Process for the preparation of formic acid or derivatives thereof
JP2962649B2 (en) * 1994-06-07 1999-10-12 科学技術振興事業団 Method for producing formamide derivative
JP2927677B2 (en) * 1994-06-07 1999-07-28 科学技術振興事業団 Method for producing formate compound
JP2005246261A (en) * 2004-03-04 2005-09-15 Nippon Steel Corp Catalyst for synthesizing formate and methanol and method for producing formate and methanol
JP5264084B2 (en) * 2006-02-17 2013-08-14 新日鐵住金株式会社 Methanol synthesis catalyst, method for producing the catalyst, and method for producing methanol
JP5264083B2 (en) * 2006-02-17 2013-08-14 新日鐵住金株式会社 Methanol synthesis catalyst, method for producing the catalyst, and method for producing methanol
JP4963112B2 (en) * 2008-03-12 2012-06-27 新日本製鐵株式会社 Methanol synthesis catalyst production method and methanol production method

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