CN103508865B - A kind of catalyzed by solid base prepares the method for 2-isopropyl-5-methyl-2-hexenoic aldehyde - Google Patents
A kind of catalyzed by solid base prepares the method for 2-isopropyl-5-methyl-2-hexenoic aldehyde Download PDFInfo
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- CN103508865B CN103508865B CN201210217774.0A CN201210217774A CN103508865B CN 103508865 B CN103508865 B CN 103508865B CN 201210217774 A CN201210217774 A CN 201210217774A CN 103508865 B CN103508865 B CN 103508865B
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- 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
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Abstract
The invention provides a kind of with 3-methylbutyraldehyd for raw material, with the solid base of alkaline earth oxide carrying alkali metal hydroxide or alkali carbonate for catalyst, the method preparing 2-isopropyl-5-methyl-2-hexenoic aldehyde.Method provided by the invention, it is to avoid use alkaline aqueous solution, decreases alkaline waste water and processes and discharge.Prepared solid base catalyst has higher activity, can prepare 2-isopropyl-5-methyl-2-hexenoic aldehyde with higher yield, and make product separation purification simpler.<!--1-->
Description
Technical field
The present invention relates to the method that catalyzed by solid base aldol condensation prepares 2-isopropyl-5-methyl-2-hexenoic aldehyde, relate in particular to a kind of solid base with alkaline earth oxide carrying alkali metal hydroxide or alkali carbonate, as catalyst, with 3-methylbutyraldehyd (isovaleral) for raw material, aldol condensation prepares 2-isopropyl-5-methyl-2-hexenoic aldehyde.
Background technology
2-isopropyl-5-methyl-2-the hexenoic aldehyde that the present invention relates to, is prepare 2-isopropyl-2-isopentyl-1, the intermediate of 3-dihydroxypropane.2-isopropyl-2-isopentyl-1,3-dihydroxypropane, as fuel additive, solvent, complexing of metal ion agent and be used for preparing Ziegler-Natta catalyst, olefinic polyreaction can be applied in, particularly in the reaction of propylene polymerization.
Generally, prepared by 2-isopropyl-5-methyl-2-hexenoic aldehyde strong base solution catalyzing and condensing 3-methylbutyraldehyd (isovaleral).Such as, reaction temperature, by the sodium hydrate aqueous solution mixing of isovaleral and 7%, is controlled at 95-105 DEG C, after reacting 6 hours, obtains 2-isopropyl-5-methyl-2-hexenoic aldehyde product (chemical reagent 1986,8(5), 262-265 by fourth Jianping et al.).This method is also studied (daily chemical industry, the 40th volume the 1st phase, 41-43, in February, 2010) by Luo Jiali et al..This method is also found in patent Ger.Offen., and 19957522 and in Pol197573.This method employs alkaline sodium hydroxide solution, adds the corrosion to equipment, and substantial amounts of alkaline waste water can be produced.
Chinese patent CN91108297.2 proposes with the ion exchange resin with strong basicity function, and catalyzing and condensing isovaleral prepares the method for 2-isopropyl-5-methyl-2-hexenoic aldehyde.The reaction of this method not exclusively, contains a large amount of unreacted isovaleral raw materials and more residue in product.
A lot of with the document of catalyzed by solid base aldehydes condensation and patent report.Such as: MgO/Al2O3 solid base is used for catalysis aldehydes condensation reaction by US5,258,558, the solid base surface area of the method synthesis is more than 250m2/g, there is relatively low Mg/Al atomic ratio, prepare 2-ethyl-2-hexenoic aldehyde for n butyraldehyde aldolization, have higher productivity and good selectivity.US5,144,089 disclose a kind of method that 2-ethyl-2-hexenoic aldehyde is prepared in butyraldehyde condensation, the MgO/Al2O3 that the method adopts Mg/Al mol ratio to be 1.5 is catalyst, when temperature is 100-190 DEG C, carrying out liquid phase aldol condensation, the selectivity of 2-ethyl-2-hexenoic aldehyde is up to 83.13%.US5,254,743 adopts bivalent metal oxide and trivalent metal oxide to carry out condensation reaction.CN102019177 has related to a kind of solid base prepared by titanium dioxide-aluminum oxide or Zirconia-alumina composite oxide carrier, generates unsaturated aldehyde for fatty aldehyde condensation under liquid-phase condition.
Relevant catalyzed by solid base 3-methylbutyraldehyd (isovaleral) prepares 2-isopropyl-5-methyl-2-hexenoic aldehyde, has no report.
Summary of the invention
It is an object of the invention to provide a kind of method preparing 2-isopropyl-5-methyl-2-hexenoic aldehyde for catalyst aldol condensation with solid base.
On the one hand, the present invention provides a kind of method that aldol condensation prepares 2-isopropyl-5-methyl-2-hexenoic aldehyde, the method is to be catalyst with a kind of support type inoganic solids alkali, catalysis 3-methylbutyraldehyd (isovaleral) carries out aldol reaction under liquid-phase condition, prepares 2-isopropyl-5-methyl-2-hexenoic aldehyde.
The reactions steps of the method includes:
1) 3-methylbutyraldehyd, catalysts and solvents are mixed, wherein, the addition of described catalyst, by the 1-40% that weight/mass percentage composition is 3-methylbutyraldehyd, solvent is methanol, ethanol, propanol, isopropanol, n-butyl alcohol, the tert-butyl alcohol, oxolane, dichloromethane, chloroform, carbon tetrachloride one of which；
(2) mixed liquor heating being carried out aldol reaction, wherein, heating-up temperature is 20-90 DEG C, and the response time is 1-48 hour；
(3) distillation obtains product 2-isopropyl-5-methyl-2-hexenoic aldehyde.
Described catalyst is with the oxide of alkaline-earth metal for carrier, the solid base catalyst of carrying alkali metal hydroxide or alkali carbonate.
Preferred embodiment is the addition of described solid base catalyst, by the 1-20% that weight/mass percentage composition is 3-methylbutyraldehyd；Described solvent is methanol or ethanol；Heating-up temperature is 60-90 DEG C, and the response time is 2-24 hour.
The oxide of described alkaline-earth metal is magnesium oxide, calcium oxide.
Described alkali metal hydroxide is Lithium hydrate, sodium hydroxide or potassium hydroxide.
Described alkali carbonate is lithium carbonate, sodium carbonate or potassium carbonate.
On the other hand, the present invention provides a kind of solid base catalyst preparation method, catalyst carrier is the oxide of alkaline-earth metal, by soluble in water for the presoma species of load, mix with the oxide of described alkaline-earth metal, drying and high-temperature roasting, obtain the solid base catalyst that alkali-metal weight/mass percentage composition is 1-50%.The weight/mass percentage composition of preferred as alkali is the solid base catalyst of 4-40%.
Suitable catalyst carrier is the oxide of the alkaline-earth metal in periodic table of elements IIA, such as magnesium oxide, calcium oxide, strontium oxide or Barium monoxide, it is preferable that calcium oxide or magnesium oxide.
The presoma species of load can be the alkali-metal hydroxide in periodic table of elements IA, such as Lithium hydrate, sodium hydroxide or potassium hydroxide, it is preferable that potassium hydroxide；Can also be the alkali-metal carbonate in periodic table of elements IA, such as lithium carbonate, sodium carbonate or potassium carbonate, it is preferable that potassium carbonate.
The preparation method of a kind of 2-isopropyl-5-methyl-2-hexenoic aldehyde provided by the invention compared with prior art, has the advantage that
1) present invention adopts a kind of solid base that can be recycled to make catalyst, it is to avoid uses alkaline aqueous solution, decreases process and the discharge of alkaline waste water.
2) solid base catalyst of the present invention has higher activity, the conversion ratio of 3-methylbutyraldehyd (isovaleral) raw material and the selectivity of 2-isopropyl-5-methyl-2-hexenoic aldehyde product can be improved, reduce existing ion exchange resin method product Raw and the more problem of level of residue.
3) method preparing 2-isopropyl-5-methyl-2-hexenoic aldehyde provided by the invention, operates easier, and product separation purification is simpler.
Detailed description of the invention
It is illustrated by the following examples the present invention, in embodiment, yield is defined as the growing amount of the growing amount/3-methylbutyraldehyd complete reaction 2-isopropyl-5-methyl-2-hexenoic aldehyde of 2-isopropyl-5-methyl-2-hexenoic aldehyde, and K is the weight/mass percentage composition of potassium in solid base catalyst.
Embodiment 1: the preparation of potassium hydroxide-calcium oxide solid base
By quality, 1 part of KOH is dissolved in 8 parts of distilled water, is subsequently adding 4 parts through 800 DEG C of activation CaO of 4 hours, stands 24 hours after being sufficiently stirred for, then dry 24 hours at 80 DEG C.By the gained solid sample heating rate to 400 DEG C with 5 DEG C/min, then constant temperature 5 hours again, obtain solid powdery potassium hydroxide-calcium oxide solid base that potassium weight/mass percentage composition is 13.9%, as catalyst.
Embodiment 2: the preparation of potassium hydroxide-calcium oxide solid base
By quality, 1 part of KOH is dissolved in 138 parts of distilled water, is subsequently adding 69 parts through 800 DEG C of activation CaO of 4 hours, stands 24 hours after being sufficiently stirred for, then dry 24 hours at 80 DEG C.By the gained solid sample heating rate to 400 DEG C with 5 DEG C/min, then constant temperature 5 hours again, obtain solid powdery potassium hydroxide-calcium oxide solid base that potassium weight/mass percentage composition is 1%, as catalyst.
Embodiment 3: the preparation of potassium hydroxide-calcium oxide solid base
By quality, 1 part of KOH is dissolved in 32 parts of distilled water, is subsequently adding 16 parts through 800 DEG C of activation CaO of 4 hours, stands 24h after being sufficiently stirred for, then dry 24 hours at 80 DEG C.By the gained solid sample heating rate to 400 DEG C with 5 DEG C/min, then constant temperature 5 hours again, obtain solid powdery potassium hydroxide-calcium oxide solid base that potassium weight/mass percentage composition is 4%, as catalyst.
Embodiment 4: the preparation of potassium hydroxide-calcium oxide solid base
By quality, 10 parts of KOH are dissolved in 20 parts of distilled water, are subsequently adding 7 parts through 800 DEG C of activation CaO of 4 hours, stand 24 hours after being sufficiently stirred for, then dry 24h at 80 DEG C.By the gained solid sample heating rate to 400 DEG C with 5 DEG C/min, then constant temperature 5 hours again, obtain solid powdery potassium hydroxide-calcium oxide solid base that potassium weight/mass percentage composition is 40%, as catalyst.
Embodiment 5: the preparation of potassium hydroxide-calcium oxide solid base
By quality, 10 parts of KOH are dissolved in 20 parts of distilled water, are subsequently adding 4 parts through 800 DEG C of activation CaO of 4 hours, stand 24 hours after being sufficiently stirred for, then dry 24 hours at 80 DEG C.By the gained solid sample heating rate to 400 DEG C with 5 DEG C/min, then constant temperature 5 hours again, obtain solid powdery potassium hydroxide-calcium oxide solid base that potassium weight/mass percentage composition is 50%, as catalyst.
Embodiment 6: utilize catalyst synthesis 2-isopropyl-5-methyl-2-hexenoic aldehyde
In 500ml there-necked flask, add 100g3-methylbutyraldehyd (isovaleral) and 100ml absolute methanol.Under agitation, it is slowly added to potassium hydroxide-calcium oxide solid base catalyst that 10g embodiment 1 prepares, is then progressively heated at 70 DEG C, this state response 8 hours, be subsequently cooled to room temperature.After rotary evaporation falls methanol, vacuum distilling, obtain 79.8g2-isopropyl-5-methyl-2-hexenoic aldehyde, yield 89.1%.
Embodiment 7-10: utilize catalyst synthesis 2-isopropyl-5-methyl-2-hexenoic aldehyde
Using the embodiment 2-5 potassium hydroxide-calcium oxide solid base catalyst prepared respectively, synthesize 2-isopropyl-5-methyl-2-hexenoic aldehyde by the method for embodiment 6, the addition of catalyst and the yield of product are shown in following table:
| Embodiment | K% | Solid base addition g | Account for the weight/mass percentage composition % of 3-methylbutyraldehyd | Yield % |
| 7 | 1 | 40 | 40 | 84.3 |
| 8 | 4 | 34.8 | 34.8 | 85.7 |
| 9 | 40 | 3.5 | 3.5 | 88.5 |
| 10 | 50 | 2.8 | 2.8 | 88.7 |
Embodiment 11-13: utilize catalyst synthesis 2-isopropyl-5-methyl-2-hexenoic aldehyde
Potassium hydroxide-calcium oxide the solid base catalyst using embodiment 1 to prepare, synthesizes 2-isopropyl-5-methyl-2-hexenoic aldehyde by the method for embodiment 6, and the addition of catalyst and the yield of product are shown in following table:
| Embodiment | Solid base addition g | Account for the weight/mass percentage composition % of 3-methylbutyraldehyd | Yield % |
| 11 | 1 | 1 | 69.3 |
| 12 | 20 | 20 | 89.3 |
| 13 | 40 | 40 | 89.4 |
Embodiment 14-20: utilize catalyst synthesis 2-isopropyl-5-methyl-2-hexenoic aldehyde
Potassium hydroxide-calcium oxide the solid base catalyst using embodiment 1 to prepare, synthesizes 2-isopropyl-5-methyl-2-hexenoic aldehyde by the method for embodiment 6, and the yield of reaction temperature, response time and product is shown in following table:
| Embodiment | Reaction temperature DEG C | Response time, h | Yield, % |
| 14 | 70 | 1 | 69.3 |
| 15 | 70 | 2 | 72.5 |
| 16 | 70 | 24 | 89.6 |
| 17 | 70 | 48 | 90.2 |
| 18 | 20 | 8 | 52.6 |
| 19 | 60 | 8 | 85.3 |
| 20 | 90 | 8 | 88.8 |
The preparation of embodiment 21-23 solid base catalyst
By the method for embodiment 1, loading on calcium oxide by Lithium hydrate, sodium hydroxide, potassium carbonate respectively, the alkali metal weight/mass percentage composition obtaining catalyst is as shown in the table:
| Embodiment | Alkali metal | Alkali metal content % |
| 21 | Lithium | 10.9 |
| 22 | Sodium | 11.5 |
| 23 | Potassium | 18.8 |
Embodiment 24-26: the preparation of solid base catalyst
By the method for embodiment 1, loading on magnesium oxide by potassium hydroxide, sodium hydroxide, potassium carbonate respectively, the alkali metal content obtaining catalyst is as shown in the table:
| Embodiment | Alkali metal | Alkali metal content % |
| 24 | Potassium | 13.6 |
| 25 | Sodium | 11.5 |
| 26 | Potassium | 18.8 |
Embodiment 27-32: utilize catalyst synthesis 2-isopropyl-5-methyl-2-hexenoic aldehyde
Using the embodiment 21-26 solid base catalyst prepared respectively, synthesize 2-isopropyl-5-methyl-2-hexenoic aldehyde by the method for embodiment 6, the addition of catalyst and the yield of product are shown in following table:
| Embodiment | Alkali metal | The addition g of solid base | Yield % |
| 27 | Lithium | 10 | 68.4 |
| 28 | Sodium | 8 | 79.8 |
| 29 | Potassium | 10 | 86.8 |
| 30 | Potassium | 12 | 89.5 |
| 31 | Sodium | 12 | 80.8 |
| 32 | Potassium | 8 | 87.9 |
Claims (7)
1. a 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method, comprises the steps:
(1) 3-methylbutyraldehyd, catalysts and solvents are mixed, wherein, the addition of described catalyst, by the 1-40% that weight/mass percentage composition is 3-methylbutyraldehyd, solvent is methanol, ethanol, propanol, isopropanol, n-butyl alcohol, the tert-butyl alcohol, oxolane, dichloromethane, chloroform, carbon tetrachloride one of which；
(2) mixed liquor heating being carried out aldol reaction, wherein, heating-up temperature is 20-90 DEG C, and the response time is 1-48 hour；
(3) distillation obtains product 2-isopropyl-5-methyl-2-hexenoic aldehyde；
Described catalyst is with the oxide of alkaline-earth metal for carrier, the solid base catalyst of carrying alkali metal hydroxide.
2. 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method according to claim 1, it is characterised in that the addition of described solid base catalyst, by the 1-20% that weight/mass percentage composition is 3-methylbutyraldehyd.
3. 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method according to claim 1, it is characterised in that described heating-up temperature is 60-90 DEG C, and the described response time is 2-24 hour.
4. 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method according to claim 1, it is characterised in that the oxide of described alkaline-earth metal is magnesium oxide, calcium oxide.
5. 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method according to claim 1, it is characterised in that described alkali metal hydroxide is Lithium hydrate, sodium hydroxide or potassium hydroxide.
6. 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method according to claim 1, it is characterized in that, solid base catalyst preparation method is as follows, catalyst carrier is the oxide of alkaline-earth metal, alkali metal hydroxide is soluble in water, mix with the oxide of described alkaline-earth metal, the solid sample high-temperature roasting obtained after drying to 400 DEG C, obtain the solid base catalyst that alkali-metal weight/mass percentage composition is 1-50%.
7. 2-isopropyl-5-methyl-2-hexenoic aldehyde preparation method according to claim 6, it is characterised in that in described solid base catalyst, alkali-metal weight/mass percentage composition is 4-40%.
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| US5144089A (en) * | 1991-10-21 | 1992-09-01 | Uop | 2-ethyl-2-hexenal by aldol condensation of butyraldehyde in a continuous process |
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| CN102019177A (en) * | 2009-09-18 | 2011-04-20 | 中国石油天然气股份有限公司 | Solid base catalyst for aldol condensation reaction and application |
| CN102070419A (en) * | 2010-12-22 | 2011-05-25 | 浙江大学 | Method for catalyzing n-butyl aldehyde condensation reaction by magnesia catalysts and preparation of magnesia catalyst |
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