WO2009077831A1 - Procede d'obtention d'alcool a partir d'un aldehyde - Google Patents
Procede d'obtention d'alcool a partir d'un aldehyde Download PDFInfo
- Publication number
- WO2009077831A1 WO2009077831A1 PCT/IB2008/003407 IB2008003407W WO2009077831A1 WO 2009077831 A1 WO2009077831 A1 WO 2009077831A1 IB 2008003407 W IB2008003407 W IB 2008003407W WO 2009077831 A1 WO2009077831 A1 WO 2009077831A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- aldehyde
- weight
- acidic
- bar
- solid compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
Definitions
- the present invention relates to a process for obtaining alcohol from an aldehyde. More specifically, the present invention relates to a process for obtaining alcohol from an aldehyde using a bifunctional catalyst. It also relates to a process for the condensation of an aldehyde, a process for obtaining alcohol from the hydrogenation of the product of the condensation of an aldehyde as well as the products obtained through each respective process.
- Butanol (butanol-1) is currently synthesized in two stages through the hydroformylation (carbonylation) of propene by a process known as Oxo Synthesis, producing butyraldehyde. Then butyraldehyde is hydrogenated, to obtain butanol-1.
- the production of 1-butanol from the hydroformylation of propene depends on the supply of this raw material from petroleum. Due to the scarcity of this non-renewable source and its gradual rise in price, the cost of producing butanol-1 can make its use prohibitive.
- Another method involves the aldol condensation of acetaldehyde followed by dehydration producing crotonaldehyde using sodium hydroxide as a catalyst, followed by hydrogenation, producing butanol-1.
- the yield is low and the crotonaldehyde is toxic, irritating and difficult to handle, easily undergoing the polymerization reaction.
- the present invention relates to a process for obtaining alcohol from an aldehyde comprising in a first step the condensation of the aldehyde by dehydration in the presence of a specific solid catalyst forming a condensed aldehyde, followed by the hydrogenation of the latter producing alcohol, in a second step.
- This process makes it possible to obtain an alcohol with excellent conversion and selectivity.
- the first step of this process is a process for condensing two aldehyde molecules in the presence of a catalytic system comprising an acidic or basic solid compound and a metal compound at a temperature of between 10 ° C. and 300 ° C. and a pressure of between 0.01 and 200 bar, in the presence of hydrogen.
- the catalytic system can be bifunctional, performing aldol condensation and dehydration in acidic or basic media and hydrogenation in the presence of a metal.
- the catalytic system comprises as first component an acidic or basic solid compound.
- This compound may be a solid of the zeolite, clay, ceramic, resin, mineral or any other acidic or basic solid support.
- acidic solid supports mention may be made in particular of sulfonic acid resins, carboxylic resins, phosphoric resins, mineral oxides such as sulphated zirconias, acid clays such as montmorillonites and zeolites, such as H ZSM5, and HY.
- As a basic solid support there may be mentioned compounds bearing at the surface hydroxide functions or amino functions, carbonates, oxides metal such as phosphate or lanthanum oxides, basic clays such as double-lamellar hydroxides (LDH).
- LDH double-lamellar hydroxides
- the catalytic system comprises as a second component a metal compound, in particular based on Cr, Co, Ni, Cu, Rh, Pd, Ir, Pt, and / or Au. Ni, Pd, Rh, and Ir are particularly preferred.
- This compound may be the metal as such or a metal in the form of hydroxide, oxide or salt. The metal is preferably in the reduced state for its activity during the hydrogenation.
- the metal compound may be used in proportions of between 0.001% and 30% by weight, more preferably between 0.01% and 10% by weight, relative to the weight of the acidic or basic solid compound.
- the catalytic system comprises an acidic or basic solid compound on which the metal compound described above is surface-supported.
- Amberlyst® CH28 catalysts from Rohm & Haas can be mentioned.
- the catalyst system comprises an acidic or basic solid compound and a metal compound supported on a reaction-inert solid.
- the amount of catalyst system may vary between 0.01% and 60% by weight relative to the weight of aldehyde, preferably between 0.1% and 20% by weight, more preferably between 1% and 10% by weight.
- the reaction is carried out at a temperature of between 10 ° C. and 200 ° C., more preferably between 30 ° C. and 150 ° C., even more preferentially between 80 ° C. and 120 ° C.
- the reaction is carried out at a pressure of between 1 and 100 bar, more preferably between 3 and 25 bar, more preferably between 8 and 15 bar.
- the first step is carried out at a temperature of between 10 ° C. and 200 ° C. and a pressure of between 1 and 100 bar, more preferably at a temperature of between 30 ° C. and 150 ° C. and a pressure between 3 ° C. and 100 ° C. and 25 bar, more preferably, at a temperature between 80 ° C. and 120 ° C. and a pressure between 8 and 15 bar.
- Such a pressure can be obtained by adding feed to the reactor of pure hydrogen or a mixture of hydrogen and an inert gas, such as for example nitrogen or argon.
- the hydrogen partial pressure can be maintained by purging the gas head while controlling the hydrogen content.
- the aldehydes may especially be acetaldehyde, butyraldehyde or propionaldehyde.
- One or more aldehydes of different natures can be used.
- the reaction medium comprises, besides the catalytic system, only aldehydes.
- the medium preferably does not comprise any solvent and / or compounds capable of reacting during the condensation reaction, such as, for example, alcohol-type compounds.
- the process according to the invention can be carried out continuously or discontinuously, preferably in the liquid phase.
- the residence time of the first step may especially be from 5 to 300 minutes.
- the reaction of the first step can be carried out in a reactor of any type, in particular in a vertically mounted reaction tube. Many reactors implementing the method of the first step can be put in series.
- the catalyst can be placed on a fixed bed or be suspended with stirring in the reactor.
- the second step of the process involves hydrogenation of the condensed aldehyde producing alcohol.
- the condensed aldehyde is reacted with hydrogen in the gaseous or liquid phase in the presence of a hydrogenation catalyst, especially under conditions of determined temperature and pressure.
- the hydrogenation catalyst may consist of metal or supported metal containing Cr, Co, Ni, Cu, Ru, Rh, Pd, Ir, Pt, Au or their compounds and mixtures, especially in concentrations between 0.01% and 30% by weight, preferably between 0.1% and 20%, more preferably between 1% and 10%, relative to the total weight of the catalyst.
- the temperature may be between 1O 0 C and 300 0 C, preferably between 8O 0 C and 14O 0 C; and the pressure between 0.1 and 300 bar, preferably between 1 and 100 bar.
- the process for obtaining the alcohol in question considers the hydrogenation of butyraldehyde obtained during the aldol condensation of two molecules of acetaldehyde producing butanol-1.
- said catalysts may correspond to an identical material or the like.
- the process according to the invention makes it possible in particular to obtain butanol-1 from acetaldehyde, 2-ethyl hexanol from butyraldehyde or 2-methyl pentanal from propionaldehyde.
- the two steps described above are preferably carried out in different reactors, in particular arranged one after the other.
- the present invention also relates to the product that can be obtained by the aldol condensation of two molecules of aldehyde as described above.
- the subject of the present invention is also the alcohol that can be obtained from the hydrogenation of the product obtained from the aldol condensation of two aldehyde molecules, as described above.
Landscapes
- 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)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200880125414XA CN101925569A (zh) | 2007-12-14 | 2008-12-10 | 由醛获得醇的方法 |
EP08862544A EP2231576A1 (fr) | 2007-12-14 | 2008-12-10 | Procede d'obtention d'alcool a partir d'un aldehyde |
BRPI0819373 BRPI0819373A2 (pt) | 2007-12-14 | 2008-12-10 | "processo de condensação de duas moléculas de aldeídos, processo de fabricação de um álcool por reação de um aldeído condensado, produto suscetível de ser obtido da condensação aldólica de duas moléculas de aldéido e álcool suscetível de ser obtido a partir da hidrogenação" |
JP2010537532A JP2011517656A (ja) | 2007-12-14 | 2008-12-10 | アルデヒドからアルコールを得るための方法 |
US12/747,647 US20110021845A1 (en) | 2007-12-14 | 2008-12-10 | Preparation of alcohols from aldehydes |
ZA2010/04638A ZA201004638B (en) | 2007-12-14 | 2010-07-01 | Method for obtaining alcohol from an aldehyde |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0708723 | 2007-12-14 | ||
FR0708723A FR2925046A1 (fr) | 2007-12-14 | 2007-12-14 | Procede d'obtention d'alcool a partir d'un aldehyde |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009077831A1 true WO2009077831A1 (fr) | 2009-06-25 |
Family
ID=39645585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2008/003407 WO2009077831A1 (fr) | 2007-12-14 | 2008-12-10 | Procede d'obtention d'alcool a partir d'un aldehyde |
Country Status (8)
Country | Link |
---|---|
US (1) | US20110021845A1 (fr) |
EP (1) | EP2231576A1 (fr) |
JP (1) | JP2011517656A (fr) |
CN (1) | CN101925569A (fr) |
BR (1) | BRPI0819373A2 (fr) |
FR (1) | FR2925046A1 (fr) |
WO (1) | WO2009077831A1 (fr) |
ZA (1) | ZA201004638B (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102093180A (zh) * | 2009-12-15 | 2011-06-15 | 上海焦化有限公司 | 一种连续生产不饱和醛化合物的方法 |
CN102093179A (zh) * | 2009-12-15 | 2011-06-15 | 上海焦化有限公司 | 一种酸性沸石催化醛缩合的方法 |
JP2013512208A (ja) * | 2009-11-26 | 2013-04-11 | サンド・アクチエンゲゼルシヤフト | 低量の水素を用いる有機化合物の還元 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI320036B (en) | 2005-05-20 | 2010-02-01 | Process for preparing a chlorohydrin starting from a polyhydroxylated aliphatic hydrocarbon | |
US8742177B2 (en) | 2011-12-28 | 2014-06-03 | Rohm And Haas Company | Catalyst and process to produce branched unsaturated aldehydes |
US8809594B2 (en) | 2012-09-21 | 2014-08-19 | Eastman Chemical Company | Dual catalyst system for the self-condensation of alcohols |
EP3048090B1 (fr) * | 2013-09-17 | 2022-03-30 | LG Chem, Ltd. | Procédé de préparation d'alcanol |
EP3160927B1 (fr) * | 2014-06-30 | 2022-04-13 | Haldor Topsøe A/S | Procédé pour la préparation d'éthylène glycol à partir de sucres |
US10759726B2 (en) | 2016-01-07 | 2020-09-01 | Haldor Topsøe A/S | Process for the preparation of ethylene glycol from sugars |
MX2018007748A (es) | 2016-01-07 | 2018-11-14 | Topsoe Haldor As | Proceso para la preparacion de etilenglicol a partir de azucares. |
US9834501B2 (en) | 2016-01-28 | 2017-12-05 | Eastman Chemical Company | Efficient synthesis of methacroelin and other alpha, beta—unsaturated aldehydes from methanol and an aldehyde |
US9828322B2 (en) | 2016-01-28 | 2017-11-28 | Eastman Chemical Company | Efficient synthesis of methacroelin and other alpha, beta-unsaturated aldehydes over a regenerable anatase titania catalyst |
CN106111184A (zh) * | 2016-06-27 | 2016-11-16 | 山东成泰化工有限公司 | 一种异癸醇制备用催化剂及其制备方法 |
CN110871085B (zh) * | 2018-08-30 | 2022-11-29 | 淄博张店东方化学股份有限公司 | 一种糠醛催化加氢制备糠醇的负载型催化剂及其制备方法与应用 |
CN114685257B (zh) * | 2020-12-31 | 2024-04-09 | 中国石油化工股份有限公司 | 一种合成甲基异戊基酮的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4701562A (en) * | 1986-06-25 | 1987-10-20 | Union Carbide Corporation | Process for the condensation of aldehydes |
US5004845A (en) * | 1981-08-20 | 1991-04-02 | Davy Mckee (London) Limited | Hydrogenation of aldehydes |
EP1094051A1 (fr) * | 1999-10-20 | 2001-04-25 | Saudi Basic Industries Corporation | Procédé catalytique d'hydrogénation en phase liquide pour la transformation d'aldéhydes en alcools correspondants |
-
2007
- 2007-12-14 FR FR0708723A patent/FR2925046A1/fr active Pending
-
2008
- 2008-12-10 US US12/747,647 patent/US20110021845A1/en not_active Abandoned
- 2008-12-10 CN CN200880125414XA patent/CN101925569A/zh active Pending
- 2008-12-10 WO PCT/IB2008/003407 patent/WO2009077831A1/fr active Application Filing
- 2008-12-10 JP JP2010537532A patent/JP2011517656A/ja not_active Abandoned
- 2008-12-10 EP EP08862544A patent/EP2231576A1/fr not_active Withdrawn
- 2008-12-10 BR BRPI0819373 patent/BRPI0819373A2/pt not_active IP Right Cessation
-
2010
- 2010-07-01 ZA ZA2010/04638A patent/ZA201004638B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5004845A (en) * | 1981-08-20 | 1991-04-02 | Davy Mckee (London) Limited | Hydrogenation of aldehydes |
US4701562A (en) * | 1986-06-25 | 1987-10-20 | Union Carbide Corporation | Process for the condensation of aldehydes |
EP1094051A1 (fr) * | 1999-10-20 | 2001-04-25 | Saudi Basic Industries Corporation | Procédé catalytique d'hydrogénation en phase liquide pour la transformation d'aldéhydes en alcools correspondants |
Non-Patent Citations (1)
Title |
---|
XU M ET AL: "Isobutanol and Methanol Synthesis on Copper Catalysts Supported on Modified Magnesium Oxide", JOURNAL OF CATALYSIS, ACADEMIC PRESS, DULUTH, MN, US, vol. 171, no. 1, 1 October 1997 (1997-10-01), pages 130 - 147, XP004468791, ISSN: 0021-9517 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013512208A (ja) * | 2009-11-26 | 2013-04-11 | サンド・アクチエンゲゼルシヤフト | 低量の水素を用いる有機化合物の還元 |
CN102093180A (zh) * | 2009-12-15 | 2011-06-15 | 上海焦化有限公司 | 一种连续生产不饱和醛化合物的方法 |
CN102093179A (zh) * | 2009-12-15 | 2011-06-15 | 上海焦化有限公司 | 一种酸性沸石催化醛缩合的方法 |
CN102093180B (zh) * | 2009-12-15 | 2013-09-11 | 上海焦化有限公司 | 一种连续生产不饱和醛化合物的方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2231576A1 (fr) | 2010-09-29 |
CN101925569A (zh) | 2010-12-22 |
US20110021845A1 (en) | 2011-01-27 |
JP2011517656A (ja) | 2011-06-16 |
BRPI0819373A2 (pt) | 2015-04-22 |
FR2925046A1 (fr) | 2009-06-19 |
ZA201004638B (en) | 2011-03-30 |
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