CN102060669A - Method for preparing cinnamyl alcohol - Google Patents
Method for preparing cinnamyl alcohol Download PDFInfo
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- CN102060669A CN102060669A CN2010105753837A CN201010575383A CN102060669A CN 102060669 A CN102060669 A CN 102060669A CN 2010105753837 A CN2010105753837 A CN 2010105753837A CN 201010575383 A CN201010575383 A CN 201010575383A CN 102060669 A CN102060669 A CN 102060669A
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- catalyzer
- phenylacrolein
- styryl carbinol
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- immersed
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for preparing cinnamyl alcohol. The method comprises the following steps of: dissolving cinnamyl alcohol into an isopropanol solution; adding a catalyst; heating up to 100-170 DEG C, and then introducing H2 of 1-3MPa; reacting for 2-5 hours; reducing the pressure and discharging; filtering out the catalyst and evaporating out the solvent; and separating cinnamyl aldehyde from the cinnamyl alcohol to obtain the cinnamyl alcohol, wherein the used catalyst is a Co-Fe-Zn/active carclazyte loaded type catalyst. The method has the advantages of high yield, easiness of operation, and the like.
Description
Technical field
The present invention relates to a kind of preparation method of styryl carbinol.
Background technology
Phenylacrolein is α, representational compound in the beta-unsaturated aldehyde, the phenylacrolein selective hydrogenation generates the reaction of styryl carbinol, relate to the competitive hydrogenation of C-C key and C-O key, not only meaningful in theory, and have actual application value, the α on the load type metal catalyst, the heterogeneous selection hydrogenation of beta-unsaturated aldehyde, the person's that more and more causes the catalyticing research concern.The general catalyst system of being studied all is based on noble metal catalyst, the load of the precious metal that has is also very high, and Nitta etc. have studied the brill catalyzer of loading type, finds α, the selectivity of beta unsaturated alcohol is very high, but the charge capacity of this catalyzer is up to more than 40%.
The present invention adopts the Co-Fe-Zn/ atlapulgite as catalyzer, and the phenylacrolein selective hydrogenation generates styryl carbinol, selectivity height, yield height.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of styryl carbinol.
The preparation method of styryl carbinol may further comprise the steps;
Phenylacrolein is dissolved in the isopropanol solvent, adds catalyzer, behind heat temperature raising to 100～170 ℃, feed the H of 1～3MPa
2, react after 2～5 hours, the step-down discharging, with the catalyzer filtering, steaming desolventizes, and phenylacrolein is separated with styryl carbinol, obtains styryl carbinol.
Wherein raw materials used consumption is 3～8 times of phenylacrolein quality for the Virahol consumption, and catalyst levels is 5～20% of a phenylacrolein quality; Catalyzer is the active clay loaded type catalyzer of Co-Fe-Zn/, and method for preparing catalyst is that atlapulgite is immersed in a certain amount of 0.05～0.2molL
-1Fe (NO
3)
3In the solution, stirring at normal temperature 16～24h after the infrared lamp drying, is immersed in a certain amount of 0.1～0.2molL again
-1Zn (NO
3)
2In the solution, stirring at normal temperature 16～24h after the infrared lamp drying, is immersed in a certain amount of 0.1～0.3molL again
-1Co (NO
3)
3In the solution, stirring at normal temperature 16～24h, at 300～500 ℃ of roasting 2～5h, cool to room temperature promptly gets still unreduced catalyzer after the infrared lamp drying.When carrying out catalyzed reaction, catalyzer is at 200～400 ℃ of following H
2Reduce 1～5h in the atmosphere, obtain the activatory catalyzer, carry out catalyzed reaction then.
Beneficial effect of the present invention is: technology is simple, the yield height.
Concrete implementation content
Below in conjunction with specific embodiment the present invention is described in detail.
Embodiment 1
Preparation of catalysts
Atlapulgite 100g is immersed in the 0.05molL of 200ml
-1Fe (NO
3)
3In the solution, stirring at normal temperature 16h after the infrared lamp drying, is immersed in a certain amount of 0.2molL again
-1Zn (NO
3)
2In the solution, stirring at normal temperature 24h after the infrared lamp drying, is immersed in a certain amount of 0.3molL again
-1Co (NO
3)
3In the solution, stirring at normal temperature 16h, at 300 ℃ of roasting 5h, cool to room temperature promptly gets still unreduced catalyzer after the infrared lamp drying.When carrying out catalyzed reaction, catalyzer is at 400 ℃ of following H
2Reduce 5h in the atmosphere, obtain the activatory catalyzer, carry out catalyzed reaction then.
The preparation of styryl carbinol
The 100g phenylacrolein is dissolved in the 300g isopropanol solvent, adds catalyzer 5g, behind the heat temperature raising to 170 ℃, feed the H of 1MPa
2, react after 5 hours, the step-down discharging, with the catalyzer filtering, steaming desolventizes, and phenylacrolein is separated with styryl carbinol, obtains styryl carbinol 71g, yield 70%.
Embodiment 2
Preparation of catalysts
Atlapulgite 100g is immersed in the 0.2molL of 200ml
-1Fe (NO
3)
3In the solution, stirring at normal temperature 24h after the infrared lamp drying, is immersed in a certain amount of 0.1molL again
-1Zn (NO
3)
2In the solution, stirring at normal temperature 24h after the infrared lamp drying, is immersed in a certain amount of 0.1molL again
-1Co (NO
3)
3In the solution, stirring at normal temperature 16h, at 500 ℃ of roasting 5h, cool to room temperature promptly gets still unreduced catalyzer after the infrared lamp drying.When carrying out catalyzed reaction, catalyzer is at 400 ℃ of following H
2Reduce 5h in the atmosphere, obtain the activatory catalyzer, carry out catalyzed reaction then.
The preparation of styryl carbinol
Phenylacrolein 100g is dissolved in the 800g isopropanol solvent, adds catalyzer 20g, behind the heat temperature raising to 150 ℃, feed the H of 3MPa
2, react after 5 hours, the step-down discharging, with the catalyzer filtering, steaming desolventizes, and phenylacrolein is separated with styryl carbinol, obtains styryl carbinol 76.1g, yield 75%.
Claims (5)
1. the preparation method of a styryl carbinol is characterized in that: may further comprise the steps:
Phenylacrolein is dissolved in the isopropanol solvent, adds catalyzer, behind heat temperature raising to 100～170 ℃, feed the H of 1～3MPa
2, react after 2～5 hours, the step-down discharging, with the catalyzer filtering, steaming desolventizes, and phenylacrolein is separated with styryl carbinol, obtains styryl carbinol.
2. according to the preparation of claims 1 described styryl carbinol, it is characterized in that; Described raw material consumption is 3～8 times of phenylacrolein quality for the Virahol consumption.
3. according to the preparation of claims 1 described styryl carbinol, it is characterized in that; Described catalyst levels is 5～20% of a phenylacrolein quality;
4. according to the preparation of claims 1 or 3 described phenylacroleins, it is characterized in that; Described catalyzer is the active clay loaded type catalyzer of Co-Fe-Zn/;
5. according to claims 3 described catalyzer, it is characterized in that described method for preparing catalyst is: atlapulgite is immersed in a certain amount of 0.05～0.2molL
-1Fe (NO
3)
3In the solution, stirring at normal temperature 16～24h after the infrared lamp drying, is immersed in a certain amount of 0.1～0.2mol L again
-1Zn (NO
3)
2In the solution, stirring at normal temperature 16～24h after the infrared lamp drying, is immersed in a certain amount of 0.1～0.3molL again
-1Co (NO
3)
3In the solution, stirring at normal temperature 16～24h, at 300～500 ℃ of roasting 2～5h, cool to room temperature promptly gets still unreduced catalyzer after the infrared lamp drying, and when carrying out catalyzed reaction, catalyzer is at 200～400 ℃ of following H
2Reduce 1～5h in the atmosphere, obtain the activatory catalyzer, carry out catalyzed reaction then.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105753837A CN102060669A (en) | 2010-12-07 | 2010-12-07 | Method for preparing cinnamyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105753837A CN102060669A (en) | 2010-12-07 | 2010-12-07 | Method for preparing cinnamyl alcohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102060669A true CN102060669A (en) | 2011-05-18 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010105753837A Pending CN102060669A (en) | 2010-12-07 | 2010-12-07 | Method for preparing cinnamyl alcohol |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974016A (en) * | 2014-04-03 | 2015-10-14 | 长春工业大学 | Method for preparing cinnamyl alcohol through cinnamaldehyde hydrogenation |
| CN108057448A (en) * | 2016-11-07 | 2018-05-22 | 中国科学院大连化学物理研究所 | A kind of cinnamic acid selective hydrogenation prepares cinnamyl alcohol catalyst and its application |
| CN109678656A (en) * | 2018-12-29 | 2019-04-26 | 湘潭大学 | Class zeolite imidazole metal organic framework ZIFs is used for the method that alpha, beta-unsaturated aldehyde adds hydrogen to prepare alpha, beta unsaturated alcohol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1129198A1 (en) * | 1983-04-19 | 1984-12-15 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Process for preparing cinnamic alcohol |
| CN1586717A (en) * | 2004-08-05 | 2005-03-02 | 复旦大学 | Quenched skeleton cobalt base catalyst for cinnamyl aldehyde hydrogenation to prepare cinnamyl alcohol and its preparing method |
| CN101716510A (en) * | 2009-11-19 | 2010-06-02 | 复旦大学 | Amorphous catalyst containing cobalt and boron used in cinnamyl alcohol preparation by virtue of hydrogenation on cinnamic aldehyde and preparation method thereof |
-
2010
- 2010-12-07 CN CN2010105753837A patent/CN102060669A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1129198A1 (en) * | 1983-04-19 | 1984-12-15 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Process for preparing cinnamic alcohol |
| CN1586717A (en) * | 2004-08-05 | 2005-03-02 | 复旦大学 | Quenched skeleton cobalt base catalyst for cinnamyl aldehyde hydrogenation to prepare cinnamyl alcohol and its preparing method |
| CN101716510A (en) * | 2009-11-19 | 2010-06-02 | 复旦大学 | Amorphous catalyst containing cobalt and boron used in cinnamyl alcohol preparation by virtue of hydrogenation on cinnamic aldehyde and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| 《精细化工》 20050630 刘自力等 Fe对肉桂醛选择性加氢为肉桂醇的Co/gamma-Al2O3催化剂的改性研究 第447-450页 1-5 第22卷, 第6期 * |
| 刘自力等: "Fe对肉桂醛选择性加氢为肉桂醇的Co/γ-Al2O3催化剂的改性研究", 《精细化工》 * |
| 裴燕等: "Zn对非晶态Co-B催化剂巴豆醛选择加氢性能的影响", 《化学学报》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104974016A (en) * | 2014-04-03 | 2015-10-14 | 长春工业大学 | Method for preparing cinnamyl alcohol through cinnamaldehyde hydrogenation |
| CN104974016B (en) * | 2014-04-03 | 2017-07-28 | 长春工业大学 | The method that hydrogenation on cinnamic aldehyde prepares cinnamyl alcohol |
| CN108057448A (en) * | 2016-11-07 | 2018-05-22 | 中国科学院大连化学物理研究所 | A kind of cinnamic acid selective hydrogenation prepares cinnamyl alcohol catalyst and its application |
| CN108057448B (en) * | 2016-11-07 | 2020-12-01 | 中国科学院大连化学物理研究所 | Catalyst for preparing cinnamyl alcohol by selective hydrogenation of cinnamyl aldehyde and application thereof |
| CN109678656A (en) * | 2018-12-29 | 2019-04-26 | 湘潭大学 | Class zeolite imidazole metal organic framework ZIFs is used for the method that alpha, beta-unsaturated aldehyde adds hydrogen to prepare alpha, beta unsaturated alcohol |
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Application publication date: 20110518 |