CN102557878B - Take perillalcohol as catalytic material dehydrogenation synthesis cuminyl alcohol - Google Patents
Take perillalcohol as catalytic material dehydrogenation synthesis cuminyl alcohol Download PDFInfo
- Publication number
- CN102557878B CN102557878B CN201110449550.8A CN201110449550A CN102557878B CN 102557878 B CN102557878 B CN 102557878B CN 201110449550 A CN201110449550 A CN 201110449550A CN 102557878 B CN102557878 B CN 102557878B
- Authority
- CN
- China
- Prior art keywords
- perillalcohol
- cuminyl alcohol
- cuminyl
- alcohol
- catalytic material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of novel preparation method of cuminyl alcohol, directly with natural product turps synthesis perillalcohol for raw material, obtain cuminyl alcohol through catalytic dehydrogenation.Reaction is carried out under liquid phase, normal pressure, 95% is reached to cuminyl alcohol productive rate, there are the potentiality of industrial applications, the development of China's forest chemical industry can be promoted, realization utilizes renewable resources and recycling economy, and reduce raw materials cost, product is reliably safer, the fields such as food, medicine, spices can be widely used in, there are good economic results in society.
Description
Technical field
The present invention relates to a kind of method taking perillalcohol as catalytic material dehydrogenation and synthesize cuminyl alcohol, belong to the technical field of the production of fine chemistry industry.
Background technology
Cuminyl alcohol (isopropylbenzyl alcohol) is present in cumin, Huang Gaozi, senna, myrrh and Oleum Cinnamomi, has the graceful fragrance of a flower and slight leather smells, can be used for the essence modulating multiple odor type, and can be used as the improvement of lemon note.
The cuminyl alcohol that current industrial uses mainly is obtained by organic synthesis.Its synthetic method is generally obtained by corresponding cumylene hydro-reduction, and cumylene is transformed by isopropyl benzene, Paracymene and corresponding carboxylicesters etc.; Also have and adopt isopropyl benzene to be raw material, after chloromethylation, direct hydrolysis and its Ester hydrolysis of process obtain.These methods have many deficiencies, and as institute's pathway line length from starting raw material to the finished product, productive rate is not high, some severe reaction conditions, and have larger pollution to environment, and isopropyl benzene and Paracymene are all petroleum productss, the synthesis of whole cuminyl alcohol be unable to do without petroleum industry.
Summary of the invention
The object of the invention is to be to provide a kind of novel process taking perillalcohol as catalytic material dehydrogenation and synthesize cuminyl alcohol, this technological process is simple, production cost is low, product yield is high, process is pollution-free.
The present invention is achieved by the following technical solutions.With the technological process of the perillalcohol of natural product turps synthesis for stock liquid phase reaction production cuminyl alcohol, it is characterized in that, reaction is carried out under liquid phase, normal pressure, purple perilla alcohol and solvent is uniformly mixed by a certain percentage, then be that 0.1 ~ 1% of perillalcohol adds palladium/carbon catalyst by the quality of catalyzer, be that 40% of perillalcohol quality adds oleic acid remover booster by remover booster consumption, stirring heating, range of reaction temperature is 110 DEG C to 200 DEG C, reaction times is 1 ~ 4 hour, redistillation goes out product, obtains cuminyl alcohol.
The invention has the advantages that, production cost is low, and reaction efficiency is high, and production technique is simple, and process is pollution-free, can not produce harmful effect to ecosystem environment.
Embodiment
Embodiment one
To in the reactor of 100ml, add 10ml perillalcohol, 20ml reaction solvent hexanaphthene, 0.8g palladium/carbon catalyst, 4g oleic acid remover booster.Stir in a kettle., temperature of reaction controls at 110 DEG C, reacts after 2 hours and terminates, obtain product cuminyl alcohol by distillation or rectifying.The transformation efficiency of perillalcohol is greater than 99%, and the productive rate of cuminyl alcohol reaches 95%.
Embodiment two
To in the reactor of 100ml, add 10ml perillalcohol, 10ml reaction solvent hexanaphthene, 0.4g palladium/carbon catalyst, 5g oleic acid remover booster.Stir after good seal reactor, temperature of reaction controls at 120 DEG C, reacts after 3 hours and terminates, obtain product cuminyl alcohol by distillation or rectifying.The transformation efficiency of perillalcohol is greater than 99%, and the productive rate of cuminyl alcohol reaches 95%.
Embodiment three
To in the reactor of 100ml, add 10ml perillalcohol, 5ml reaction solvent hexanaphthene, 0.1g palladium/carbon catalyst, 3g oleic acid remover booster, stirs after good seal reactor, temperature of reaction controls at 130 DEG C, reacts after 4 hours and terminates, obtain product cuminyl alcohol by distillation or rectifying.The transformation efficiency of perillalcohol is greater than 99%, and the productive rate of cuminyl alcohol reaches 95%.
Claims (1)
1. be a method for catalytic material dehydrogenation synthesis cuminyl alcohol with perillalcohol, it is characterized in that comprising the following steps:
Perillalcohol and hexanaphthene organic solvent, under liquid phase, normal pressure, are 0.5 ~ 2 to be uniformly mixed by a by volume;
B, be then that 0.1 ~ 10% of perillalcohol adds palladium/carbon catalyst by the quality of catalyzer, the 10-60% being perillalcohol quality by remover booster consumption adds oleic acid remover booster;
C, stirring heating, range of reaction temperature is 100 DEG C to 200 DEG C, and the reaction times is 1 ~ 4 hour;
D, then be between 80 DEG C to 150 DEG C in temperature, obtain product cuminyl alcohol through underpressure distillation in 2 ~ 5 hours or rectifying, hexanaphthene reuse.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110449550.8A CN102557878B (en) | 2011-12-29 | 2011-12-29 | Take perillalcohol as catalytic material dehydrogenation synthesis cuminyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110449550.8A CN102557878B (en) | 2011-12-29 | 2011-12-29 | Take perillalcohol as catalytic material dehydrogenation synthesis cuminyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102557878A CN102557878A (en) | 2012-07-11 |
| CN102557878B true CN102557878B (en) | 2016-02-17 |
Family
ID=46404659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110449550.8A Expired - Fee Related CN102557878B (en) | 2011-12-29 | 2011-12-29 | Take perillalcohol as catalytic material dehydrogenation synthesis cuminyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102557878B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068466A (en) * | 1989-09-06 | 1991-11-26 | Unilever Patent Holdings B.V. | Cymenol preparation by transfer dehydrogenation |
| US5082979A (en) * | 1989-09-06 | 1992-01-21 | Unilever Patent Holdings B.V. | Cymenol preparation by direct dehydrogenation |
| CN102070446A (en) * | 2010-12-07 | 2011-05-25 | 浙江新化化工股份有限公司 | Method for producing acetic p-isopropyl phenyl methyl ester |
-
2011
- 2011-12-29 CN CN201110449550.8A patent/CN102557878B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068466A (en) * | 1989-09-06 | 1991-11-26 | Unilever Patent Holdings B.V. | Cymenol preparation by transfer dehydrogenation |
| US5082979A (en) * | 1989-09-06 | 1992-01-21 | Unilever Patent Holdings B.V. | Cymenol preparation by direct dehydrogenation |
| CN102070446A (en) * | 2010-12-07 | 2011-05-25 | 浙江新化化工股份有限公司 | Method for producing acetic p-isopropyl phenyl methyl ester |
Non-Patent Citations (4)
| Title |
|---|
| Acid Catalyzed Isomerization of Monocyclic Monoterpenes;Hiroshi KAYAHARA et al.;《Agr. Biol. Chem.》;19701231;第34卷(第11期);第1597－1602页 * |
| 一种合成对异丙基苯酚的新方法研究;湛雪辉等;《湖南大学学报(自然科学版)》;20100131;第37卷(第1期);第67－70页 * |
| 二氢枯茗酸催化脱氢合成对异丙基苯甲酸的新方法;姜红宇等;《湖南城市学院学报（自然科学版）》;20090331;第18卷(第1期);第41－43页 * |
| 枯茗醇的合成研究;施达常等;《化学世界》;19941231(第8期);第415－418页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102557878A (en) | 2012-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103846104A (en) | Catalyst for synthesizing methacrolein from propionaldehyde and formaldehyde and application thereof | |
| CN104447261A (en) | Method for preparing cyclopentanol and cyclopentanone by using cyclopentane | |
| CN103896703B (en) | One-step catalytic converts lignocellulose and produces C5, C6the method of alkane | |
| CN102557878B (en) | Take perillalcohol as catalytic material dehydrogenation synthesis cuminyl alcohol | |
| CN102731333A (en) | Method for preparing tetracaine | |
| CN104926610B (en) | The preparation method of dihydromyrcenol | |
| CN102603500A (en) | Method for preparing glutaraldehyde by utilizing microchannel reactor | |
| CN104311404A (en) | Method for producing cinnamyl aldehyde | |
| CN102260170B (en) | Method for microwave pipeline production of butyl acetate | |
| CN106748643B (en) | A kind of preparation method of 1- adamantanol | |
| CN100465149C (en) | Preparation method of chlorophenyl acetic acid | |
| CN102557877A (en) | Method for increasing yield of terpinol in near homogenous phase double-phase reaction system | |
| CN102001922B (en) | Method for synthesizing diphenoxyl methane | |
| CN114539026B (en) | Method for synthesizing 1, 2-pentanediol by using ethanol and 1, 2-propanediol as raw materials | |
| CN101597221B (en) | Method for synthesizing natural perfume nonanal | |
| CN203319902U (en) | Novel butyl formate production device | |
| CN102531832A (en) | Preparation method for bromopentafluorobenzene | |
| CN110357762B (en) | Preparation method for continuously producing alpha-phenethyl alcohol | |
| CN108484353B (en) | Synthetic method of 2, 4-dichloro-5-fluoro (trichloromethyl) benzene | |
| CN103896708B (en) | A kind of method utilizing lactic acid or lactic acid salt preparing propone | |
| CN104230666A (en) | Method for preparing terpineol from 3-carene | |
| CN101704705B (en) | Method for converting isobornyl isopropyl ether | |
| CN203319899U (en) | Mechanical device for producing methane acid as byproduct | |
| CN100577629C (en) | Method for preparing cinnamyl formate | |
| CN102351672A (en) | Method for continuously and efficiently preparing methyl ethyl ketone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160217 Termination date: 20181229 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |