WO2010043581A1 - Verfahren und katalysatoren zur herstellung von cyclischen carbonaten - Google Patents
Verfahren und katalysatoren zur herstellung von cyclischen carbonaten Download PDFInfo
- Publication number
- WO2010043581A1 WO2010043581A1 PCT/EP2009/063249 EP2009063249W WO2010043581A1 WO 2010043581 A1 WO2010043581 A1 WO 2010043581A1 EP 2009063249 W EP2009063249 W EP 2009063249W WO 2010043581 A1 WO2010043581 A1 WO 2010043581A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oxide
- catalyst
- heterogeneous catalyst
- carbonate
- catalysts
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Definitions
- the invention relates to a process for preparing cyclic carbonates by reacting a polyhydric alcohol with a dialkyl carbonate in the presence of a heterogeneous catalyst, which is characterized in that the heterogeneous catalyst is a basic mixed oxide or supported on a carrier oxide.
- Cyclic carbonates are important as solvents, additives for cosmetics and detergents. They are also used for the production of epoxy resins, polycarbonates and polyurethanes.
- Cyclic carbonates such as glycerol carbonate can be prepared by reacting polyhydric alcohols with dialkyl carbonate in the presence of a catalyst.
- alkylammonium salts or pyridinium salts are used as homogeneous catalysts.
- EP-A 739 888 discloses the use of zeolites as catalysts.
- the reaction mixture of glycerol and dialkyl carbonate contains the zeolites as heterogeneous catalysts.
- the basic catalysts are in particular alkali and / or alkaline earth salts, e.g. to the corresponding oxides, hydroxides or chlorides. Preference is given to the use of mixtures of chlorides and oxides.
- the listed alkali and alkaline earth chlorides, in particular the lithium chloride, are at least partially water-soluble.
- Homogeneous catalysts generally have the disadvantage that they are difficult to separate from the product mixture. On the other hand, heterogeneous catalysts can easily be recovered and reused.
- heterogeneous catalysts are desired which cause the highest possible yield and selectivity with the shortest possible reaction time.
- the heterogeneous catalysts should contain as few constituents as possible which dissolve out of the catalyst under the reaction conditions (leaking) and thus introduce unwanted impurities into the product mixture.
- the presence of such Impurities are critical and cause in the distillation of glycerol carbonate decomposition to explosive glycidol.
- the required amounts of catalyst should be as low as possible.
- the object of the present invention was therefore a process for the preparation of cyclic carbonates in which such catalysts are used.
- cyclic carbonates are prepared by reacting a polyhydric alcohol with a dialkyl carbonate.
- Suitable polyhydric alcohols are chemical compounds having at least two hydroxyl groups, which form a ring system by reaction with dialkyl carbonates.
- Preferred polyhydric alcohols are aliphatic compounds having at least two hydroxyl groups which are relative to each other in 1, 2 position, 1, 3 position or 1, 4 position.
- 1, 2 position are the two hydroxyl groups on adjacent carbon atoms and in the above reaction, a 5-ring is formed; in 1, 3 position corresponding to a 6-ring and at a 1, 4 position forms a 7-ring. It is preferably a 1, 2 position, so that forms a 5-ring.
- the polyhydric alcohol is preferably an aliphatic diol or triol in which two hydroxyl groups are in the 1,2-position.
- the polyhydric alcohol preferably contains no further functional groups and in particular has a molecular weight of less than 300 g / mol.
- glycerol Particularly preferred is glycerol.
- dimethyl carbonate is particularly preferred.
- a heterogeneous catalyst is used.
- the heterogeneous catalyst forms its own phase under the reaction conditions.
- the heterogeneous catalyst is solid, while the starting materials are liquid or gaseous.
- heterogeneous catalyst a basic mixed oxide or a supported basic oxide is used.
- the mixed oxide is an oxide of at least two different elements.
- the mixed oxide is basic when it leads to a pH increase in water.
- the mixed oxides are preferably mixtures of at least two oxides selected from oxides of metals of the main groups I a, II a, III a, and IV a of the periodic table, the subgroups II b, III b and IV b of the Periodic Table, and the lanthanides.
- the choice of oxides is made on the proviso that the resulting mixed oxide is basic.
- the mixed oxide preferably contains at least one oxide from the main group IIa;
- it is also possible basic mixed oxides without the use of an oxide from the group Il a is possible, for example. a mixed oxide of zinc oxide (ZnO) and aluminum oxide (Al 2 O 3).
- mixed oxides which are composed of oxides of metals of groups I a, III a, III a, I b and II b of the Periodic Table, wherein at least one oxide of a metal of the main group Il a is contained in the mixed oxide.
- the mixed oxide may contain more than two metal oxides, but a large number of different metal oxides in the mixed oxide is not necessary.
- Already suitable are mixed oxides of two or three metal oxides, in particular of two metal oxides.
- the heterogeneous catalyst is a base oxide supported on a support.
- the support may be of any inorganic material such as zeolites, carbon, polymers, alumina, titania, zirconia, silica, magnesia, silica-aluminas, silica-titania, silica-zirconia, titania-zirconia, magnesia-alumina ,
- the support is preferably an inorganic support, in particular a metal oxide or a nonmetal oxide.
- it is a carrier of zirconium oxide, silica, alumina, titania or mixtures thereof.
- At least one basic oxide is applied to the support. It may be z. B. a metal oxide of metals of the main groups I a, II a, III a, and IV a of the Periodic Table, the subgroups II b, III b and IV b of the Periodic Table, as well as the lanthanides act.
- At least one metal oxide of a metal of the main group I a or II a, the subgroup III b or the lanthanides is applied to the support.
- alkaline earth oxide main group IIa
- CaO CaO
- BaO BaO
- MgO magnesium
- the heterogeneous catalyst is a supported catalyst of a metal oxide, in particular of ZrO.sub.2, TiO.sub.2, SiO.sub.2 or Al.sub.2O.sub.3, more preferably ZrO.sub.2, to which at least one further metal oxide, in particular an alkaline earth oxide, e.g. CaO, BaO or MgO is applied.
- a further metal oxide in particular an alkaline earth oxide, e.g. CaO, BaO or MgO is applied.
- it is a base supported catalyst with a carrier of zirconium dioxide, is applied to the CaO.
- the applied metal oxide can be located for the most part on the surface of the support, but the metal oxide or the corresponding metal cations can also be distributed substantially uniformly in the support;
- the person skilled in the art also speaks here of a doping of the oxidic support with the relevant metal cations.
- the mode of application or distribution in or on the carrier is responsible for the effect of Catalyst of minor importance and depends only on the method of preparation and / or the porosity of the carrier.
- the content of metal oxide applied in the supported catalyst preferably corresponds to an amount of from 0.1 to 25% by weight, more preferably from 0.5 to 10% by weight, of alkaline earth cations, based on the total supported catalyst.
- the catalysts may additionally be modified, e.g. by further doping with other alkali metals, alkaline earth metals, chalcogens or halogens.
- they preferably contain no or at most small constituents of compounds which can leach out of the heterogeneous catalyst under the reaction conditions and thus lead to the problem of "leaking."
- a content of water-soluble alkali metal salts such as LiCl is as low as possible the content of water-soluble alkali metal salts is less than 0.5 part by weight, more preferably less than 0.1 part by weight per 100 parts by weight of heterogeneous catalyst.
- the heterogeneous catalysts can be used in the form of powder or preferably in the form of shaped articles such as extrudates, SpNt, rings, hollow cylinders, spheres or tablets having a characteristic diameter of 0.1 to 5 mm, preferably 1 to 3 mm.
- the characteristic diameter results from six times the quotient of the volume of the shaped body and of the geometric shaped body surface. Binders can be added to the catalyst for the production of moldings.
- the catalysts may have pores, e.g. B. with a pore volume 0.05 to 1, 0 ml / g.
- the basic mixed oxides can be prepared by customary methods known to the person skilled in the art.
- the desired metal salts can first be dissolved in water and then precipitated with a suitable precipitating agent (eg aqueous ammonia solution, solutions of alkali metal carbonates or bicarbonates, such as sodium carbonate, urotropin, etc.). Thereafter, the resulting solid can be washed and dried, for. B. also by spray drying. Finally, the product obtained directly or shortly before use later at temperatures of 200 to 1200, in particular 400 to 600 0 C, for example, under air or nitrogen, are activated.
- a suitable precipitating agent eg aqueous ammonia solution, solutions of alkali metal carbonates or bicarbonates, such as sodium carbonate, urotropin, etc.
- an aqueous solution of the desired metal salts is prepared first.
- the carrier is then treated with this solution.
- the amount of solution can be such that it is completely or almost completely absorbed by the carrier (impregnation on water absorption).
- the catalyst can also be dispersed in the aqueous solution and then separated from the solution, for. B. by filtration. Subsequently, in turn, an activation at high temperatures, as described above, take place.
- the starting materials can be reacted in the liquid or gas phase in the presence of the heterogeneous catalyst.
- the reaction preferably takes place in the liquid phase.
- the polyhydric alcohol or the dialkyl carbonate can be used in excess.
- the dialkyl carbonate preferably dimethyl carbonate, is used in excess, e.g. can be used on 1 mol of polyhydric alcohol (glycerol) 1, 1 to 10 mol, in particular 1, 5 to 8 mol or 1, 5 to 5 mol of dialkyl carbonate.
- the reaction can be carried out at atmospheric pressure, reduced pressure or overpressure. Preferably, it is carried out at atmospheric pressure.
- the reaction is preferably carried out at elevated temperature, e.g. B. at temperatures of 30 to 100 0 C, in particular 50 to 90 0 C.
- the reaction can be carried out discontinuously (batchwise, ie with presentation of the entire amount of all starting materials), semi-continuously (metered addition of a portion of the starting materials during the reaction) or continuously.
- both the polyhydric alcohol and the dialkyl carbonate are preferably continuously supplied.
- the heterogeneous catalyst is preferably used in amounts of 0.1 to 10 parts by weight, particularly preferably 0.2 to 5 parts by weight, based on 100 parts by weight of polyhydric alcohol.
- the heterogeneous catalyst can in a simple manner, for. B. by filtration, separated from the product mixture, optionally worked up and recycled. On a content of soluble components in the heterogeneous catalyst, which lead to the problem of "leaking", can be dispensed with.
- the heterogeneous catalyst also has a long service life. In a continuous procedure, a high yield and selectivity over a long time is maintained.
- the catalyst can be used repeatedly; after the batch preparation of the cyclic carbonate, the catalyst can be separated from the product and used again for a new batch preparation; this can be done several times, z. B. be repeated up to 10 times with reuse of the same catalyst.
- the extrudates were dried for 16 h at 120 0 C and finally calcined in air at 600 0 C for 1 h. There were obtained 15.1 kg Strfitlinge with a CaO content of 35% and an Al 2 O 3 content of 65%.
- EXAMPLE 2 10 l of water were introduced into a precipitation vessel and then simultaneously a 20% strength aqueous Na 2 CC 3 solution and an aqueous solution of magnesium nitrate, zinc nitrate and aluminum nitrate (140 kg of solution containing 1.56 kg of MgO, 3.25 kg ZnO and AI2O3 8.19 kg) with stirring at 8O 0 C and pH 5.5 brought to precipitation. After addition of a total of 190 kg Na2CO3 solution, the final pH value was 7.8. the product is filtered de wur- , washed with water and dried for 16 h at 100 ° C.
- Example 5 200 g of zirconium oxide (material SZ 31108, Norpro) in the form of 3 mm extrudates were calcined for 5 h at 500 ° C. in air. The strands were placed in a flask and a clear solution of 93.74 g of Ca (NOs) 2 * 4 H2O and 80.4 g of water was added. The impregnated extrudates were then predried for 30 min at RT and for a further 30 min at 8O 0 C on a rotary evaporator. Then, the extrudates were carried out at 100 0 C for 16 h air dried and finally h with a heating rate of 2 K / min at 500 0 C for 16 calcined in air. There were obtained 226.9 g of beige strands with a 6.5% Ca content.
- Example 6 200 g of zirconium oxide (. Material SZ 31108, Norpro Fa) in the form of 3 mm extrudates were calcined for 5 h at 500 0 C in air. The strands were placed in a flask and a clear solution of 155.44 g of Mg (NOs) 2 * 6 H2O and 80.4 g of water was added. The impregnated extrudates were then predried for 30 min at RT and for a further 30 min at 8O 0 C on a rotary evaporator. Then, the strand pieces were air-dried at 100 ° C for 16 hours and finally calcined at a heating rate of 2 K / min. At 500 ° C for 16 hours in air. There were obtained 206.4 g of white rods with a Mg content of 1.7%.
- Example 7 120 g of titanium oxide (. S material 150, Fa Finnti) in the form of 1, 5 mm extrudates were placed in a flask and a clear solution of 29.5 g of Ca (NO3) 2 * 4 H2O and 62 g of water were added , The material was well mixed several times, then dried at 120 0 C for 16 h in air and finally calcined at a heating rate of 10 K / min at 500 0 C for 2 h in air. There were obtained 124.2 g of white strands with a Ca content of 4.2%.
- EXAMPLE 9 120 g of alumina (material D10-10, BASF) 4 H2O and 144 g of water was added in the form of 1, 5 mm extrudates were placed in a flask and a clear solution of 29.5 g of Ca (NO3) 2 *. The material was well mixed several times, then dried at 120 0 C for 16 h in air and finally calcined at a heating rate of 10 K / min at 500 0 C for 2 h in air. There were obtained 123.8 g of white stranders with a Ca content of 3.3%.
- Example 11 1.5 kg of MgO granules (Magnesia) were mixed with 45 g of magnesium stearate. The mixture was processed on a rotary tabletting machine into 3 x 3 mm tablets with a pressing force of 12.4 kN. The tablets were finally calcined at 450 ° C in air for 2 h.
- Catalysts 1 and 2 are mixed oxides according to the invention.
- Catalysts 4 to 9 are supported catalysts according to the invention, catalysts 10 and 11 are for comparison
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/124,138 US20110201828A1 (en) | 2008-10-17 | 2009-10-12 | Method and catalysts for producing cyclic carbonates |
CN2009801412218A CN102186837A (zh) | 2008-10-17 | 2009-10-12 | 制备环碳酸酯的方法和催化剂 |
JP2011531459A JP2012505853A (ja) | 2008-10-17 | 2009-10-12 | 環式カーボネートを製造するための方法および触媒 |
EP09783934A EP2350041A1 (de) | 2008-10-17 | 2009-10-12 | Verfahren und katalysatoren zur herstellung von cyclischen carbonaten |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08166949 | 2008-10-17 | ||
EP08166949.1 | 2008-10-17 |
Publications (1)
Publication Number | Publication Date |
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WO2010043581A1 true WO2010043581A1 (de) | 2010-04-22 |
Family
ID=42014120
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/063249 WO2010043581A1 (de) | 2008-10-17 | 2009-10-12 | Verfahren und katalysatoren zur herstellung von cyclischen carbonaten |
Country Status (6)
Country | Link |
---|---|
US (1) | US20110201828A1 (de) |
EP (1) | EP2350041A1 (de) |
JP (1) | JP2012505853A (de) |
KR (1) | KR20110070915A (de) |
CN (1) | CN102186837A (de) |
WO (1) | WO2010043581A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2970254A1 (fr) * | 2011-01-11 | 2012-07-13 | Rhodia Operations | Procede de preparation de carbonate d'alcool |
WO2014009421A1 (fr) * | 2012-07-11 | 2014-01-16 | Rhodia Operations | Procédé de préparation de (poly)carbonate de polyglycérol |
WO2019034716A1 (de) | 2017-08-17 | 2019-02-21 | Basf Se | Verfahren zur herstellung von (meth)acrylaten von glycerincarbonat |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104248982B (zh) * | 2013-06-27 | 2016-12-28 | 中国科学院大连化学物理研究所 | La改性氧化铝载体的制备及载体和长链烷烃脱氢催化剂 |
CN107915707B (zh) * | 2016-10-08 | 2020-10-16 | 中国石油化工股份有限公司 | 制备碳酸乙烯酯的方法 |
CN109438410B (zh) * | 2018-12-05 | 2021-09-03 | 苏州祺添新材料有限公司 | 一种MgO/NaY固体碱催化剂在合成碳酸乙烯酯中的应用 |
CN111514878B (zh) * | 2020-05-12 | 2022-03-29 | 东南大学 | 一种用于合成碳酸甘油酯催化剂的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06329663A (ja) * | 1993-05-25 | 1994-11-29 | Nisso Maruzen Chem Kk | グリセロールカーボネートの製造方法 |
EP1156042A1 (de) * | 1999-02-24 | 2001-11-21 | Kao Corporation | Verfahren zur herstellung von glycerolcarbonat |
DE102005060732A1 (de) * | 2005-12-16 | 2007-06-21 | Röhm Gmbh | Verfahren zur Herstellung von Glycerincarbonat |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5091543A (en) * | 1990-10-15 | 1992-02-25 | Arco Chemical Technology, Inc. | Preparation of cyclic carbonates using alkylammonium and tertiary amine catalysts |
DE102005055541A1 (de) * | 2005-11-18 | 2007-05-24 | Basf Ag | Alkenylbernsteinsäureanhydride aus Oligomeren von C4- bis C8-Olefinen und Maleinsäureanhydrid, Verfahren zu ihrer Herstellung und ihre Verwendung |
-
2009
- 2009-10-12 JP JP2011531459A patent/JP2012505853A/ja not_active Withdrawn
- 2009-10-12 CN CN2009801412218A patent/CN102186837A/zh active Pending
- 2009-10-12 WO PCT/EP2009/063249 patent/WO2010043581A1/de active Application Filing
- 2009-10-12 KR KR1020117011040A patent/KR20110070915A/ko not_active Application Discontinuation
- 2009-10-12 EP EP09783934A patent/EP2350041A1/de not_active Withdrawn
- 2009-10-12 US US13/124,138 patent/US20110201828A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06329663A (ja) * | 1993-05-25 | 1994-11-29 | Nisso Maruzen Chem Kk | グリセロールカーボネートの製造方法 |
EP1156042A1 (de) * | 1999-02-24 | 2001-11-21 | Kao Corporation | Verfahren zur herstellung von glycerolcarbonat |
DE102005060732A1 (de) * | 2005-12-16 | 2007-06-21 | Röhm Gmbh | Verfahren zur Herstellung von Glycerincarbonat |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2970254A1 (fr) * | 2011-01-11 | 2012-07-13 | Rhodia Operations | Procede de preparation de carbonate d'alcool |
WO2012095435A1 (fr) * | 2011-01-11 | 2012-07-19 | Rhodia Operations | Procede de preparation de carbonate d'alcool utilisant comme catalyseurs des oxides de terres rares |
CN103415512A (zh) * | 2011-01-11 | 2013-11-27 | 罗地亚管理公司 | 使用稀土氧化物作为催化剂制备醇碳酸酯的方法 |
US20130345441A1 (en) * | 2011-01-11 | 2013-12-26 | Rhodia Operations | Method for preparing alcohol carbonate using rare earth oxides as catalysts |
US9238638B2 (en) | 2011-01-11 | 2016-01-19 | Rhodia Operations | Method for preparing alcohol carbonate using rare earth oxides as catalysts |
WO2014009421A1 (fr) * | 2012-07-11 | 2014-01-16 | Rhodia Operations | Procédé de préparation de (poly)carbonate de polyglycérol |
FR2993269A1 (fr) * | 2012-07-11 | 2014-01-17 | Rhodia Operations | Procede de preparation de (poly)carbonate de polyglycerol |
US9242956B2 (en) | 2012-07-11 | 2016-01-26 | Rhodia Operations | Method for producing polyglycerol (poly)carbonate |
WO2019034716A1 (de) | 2017-08-17 | 2019-02-21 | Basf Se | Verfahren zur herstellung von (meth)acrylaten von glycerincarbonat |
US10759732B2 (en) | 2017-08-17 | 2020-09-01 | Basf Se | Process for producing (meth)acrylates from glycerol carbonate |
Also Published As
Publication number | Publication date |
---|---|
KR20110070915A (ko) | 2011-06-24 |
JP2012505853A (ja) | 2012-03-08 |
CN102186837A (zh) | 2011-09-14 |
EP2350041A1 (de) | 2011-08-03 |
US20110201828A1 (en) | 2011-08-18 |
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