CN1043192C - Catalyst for hydrogenation preparing bata-phenethyl alcohol from phenylethylene oxide - Google Patents
Catalyst for hydrogenation preparing bata-phenethyl alcohol from phenylethylene oxide Download PDFInfo
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- CN1043192C CN1043192C CN94112146A CN94112146A CN1043192C CN 1043192 C CN1043192 C CN 1043192C CN 94112146 A CN94112146 A CN 94112146A CN 94112146 A CN94112146 A CN 94112146A CN 1043192 C CN1043192 C CN 1043192C
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- phenethyl alcohol
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- bata
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- amine
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a catalyst for preparing beta-phenylethanol from styrene oxide catalytic hydrogenation, which comprises skeleton nickel and sodium hydroxide. The catalyst is characterized in that amine is added into the components. The catalyst has the advantages that the reaction of beta-phenylethanol is easy to control, the generation amount of by-products, namely ethylbenzene and phenylacetaldehyde is little, the quality of products is good, etc.
Description
The present invention relates to the catalyzer of Styrene oxide 98min. hydrogenation preparing bata-phenethyl alcohol.
Bata-phenethyl alcohol is the spices with soft and fine and smooth rose scent.Be present in rose oil, orange flower oil, the spiceleaf wet goods essential oil in the form of occurring in nature, also be present in Yilan, Yilan, narcissus, jacinthe, lily, tealeaves, the tobacco leaf, industrially make with synthetic with free or its ester.The industry synthetic route mainly contains from toluene and begins to prepare bata-phenethyl alcohol, benzene and oxyethane at directly synthetic bata-phenethyl alcohol under the aluminum chloride katalysis and by Styrene oxide 98min. hydrogenation preparing bata-phenethyl alcohol under skeleton nickel catalyzed effect.Preceding two synthetic routes,, shortcomings such as side reaction violent, transportation difficulty many because of its step that responds are so existing industrial main employing is from the method for Styrene oxide 98min. hydrogenation preparing bata-phenethyl alcohol.The clear 53-31635 of document has introduced the method with skeletal nickel catalyst hydrogenation preparing bata-phenethyl alcohol, catalyzer with this method, exist by product ethylbenzene, phenylacetic aldehyde growing amount more in the reaction process, can produce stink beastly, thereby reduce the water-soluble of bata-phenethyl alcohol, influence product quality, the operation temperature is below 10 ℃ in addition, speed of response is slow, shortcoming such as unsatisfactory on industrial production.For overcoming the problem of above-mentioned existence, reduce the growing amount of by product ethylbenzene, phenylacetic aldehyde, improve operation condition, we have invented a kind of based on skeleton nickel, add the new catalyzer that promotor is formed.
Catalyzer of the present invention is to be realized by following technical scheme, at first with nickel-aluminium alloy, sodium hydroxide, water with 1: 1.30: 5 (weight) ratio, under 5～30 ℃ of conditions, join alumel in the aqueous sodium hydroxide solution gradually, react being lower than under 50 ℃ of temperature of reaction, after treating that alloy adds, constant temperature 1 hour is overflowed until no hydrogen.
Above-mentioned skeleton nickel liquid phase is removed alkali lye, under agitation wash for several times, till water is neutrality, remove water, use 95% washing with alcohol again 2～3 times, promptly make skeleton nickel with deionized water.To account for the skeleton nickel of total catalyst levels 85～98% (weight) then, the amine that accounts for the sodium hydroxide of total catalyst levels 1.5～8% (weight) and account for total catalyst levels 0.01～7% (weight) joins in the ethanol together, it is fully stirred, promptly get Styrene oxide 98min. hydrogenation preparing bata-phenethyl alcohol catalyzer with greater activity, amine wherein is Trimethylamine 99, diethylamine, triethylamine, thanomin, diethanolamine, trolamine or its mixture, effect is Trimethylamine 99 preferably, triethylamine, trolamine or its mixture, the add-on of amine scope preferably are 0.05～2% (weight) that accounts for total catalyst levels.
Among the present invention, owing in skeleton nickel, added the component of amine, suppress the growing amount of by product ethylbenzene, phenylacetic aldehyde preferably, improved the quality of product bata-phenethyl alcohol, reaction conditions also is improved, solved the deficiency in the conventional art.
Embodiment 1
At first with nickel-aluminium alloy, sodium hydroxide, water with 1: 1.30: 5 (weight) ratio, under 5～30 ℃ of conditions, join nickel-aluminium alloy in the aqueous sodium hydroxide solution gradually, under less than 50 ℃ of temperature of reaction, react, after treating that alloy adds, constant temperature 1 hour is overflowed until no hydrogen.
Above-mentioned skeleton nickel liquid phase is removed alkali lye, under agitation wash for several times, till ph value of aqueous phase is 7, remove water, use 95% washing with alcohol again 2～3 times, promptly make skeleton nickel with deionized water.
Take by weighing 40 milligrams of the above-mentioned skeleton nickel that makes 3.84 grams, sodium hydroxide 0.12 gram, thanomin, they are joined in the alcohol solvent together, stir mixedly, promptly get Styrene oxide 98min. hydrogenation preparing bata-phenethyl alcohol catalyzer.
With the catalyzer made and raw material Styrene oxide 98min. 46 grams, inert solvent 16 grams, put into the autoclave that 100 milliliters of bands stir, feed hydrogen in autoclave, reaction is 6 hours under 35 ℃ of temperature of reaction, reaction pressure 1.5MPa condition, carry out the catalyst activity evaluation, the result is as follows;
Bata-phenethyl alcohol reaction yield 97.5%
Ethyl-benzene level 652ppm
Phenylacetic aldehyde content 40ppm
Embodiment 2
According to each step of embodiment 1, add 280 milligrams of skeleton nickel 3.44 grams, sodium hydroxide 0.28 gram, Trimethylamine 99, under 40 ℃ of temperature of reaction, reaction pressure 1.3MPa condition, carry out the catalyst activity evaluation, the result is as follows:
Bata-phenethyl alcohol reaction yield 98.0%
Ethyl-benzene level 512ppm
Phenylacetic aldehyde content 20ppm
Embodiment 3
According to each step of embodiment 1, add 160 milligrams of skeleton nickel 3.6 grams, sodium hydroxide 0.24 gram, triethylamine, under 40 ℃ of temperature of reaction, reaction pressure 1.4MPa condition, carry out the catalyst activity evaluation, the result is as follows:
Bata-phenethyl alcohol reaction yield 98.5%
Ethyl-benzene level 435ppm
Phenylacetic aldehyde content 18ppm
Embodiment 4
According to each step of embodiment 1, add 15 milligrams of skeleton nickel 3.8 grams, sodium hydroxide 0.20 gram, trolamine, under 45 ℃ of temperature of reaction, reaction pressure 1.8MPa condition, carry out the catalyst activity evaluation, the result is as follows:
Bata-phenethyl alcohol reaction yield 98.9%
Ethyl-benzene level 400ppm
Phenylacetic aldehyde content 15ppm
Embodiment 5
According to each step of embodiment 1, add 80 milligrams of skeleton nickel 3.85 grams, sodium hydroxide 0.072 gram, ethamine, under 40 ℃ of temperature of reaction, reaction pressure 2.0MPa condition, carry out the catalyst activity evaluation, the result is as follows:
Bata-phenethyl alcohol reaction yield 97.9%
Ethyl-benzene level 600ppm
Phenylacetic aldehyde content 25ppm
Claims (4)
1, a kind of catalyzer that is used for Styrene oxide 98min. hydrogenation preparing bata-phenethyl alcohol, comprise the skeleton nickel that accounts for total catalyst weight 85～98%, the sodium hydroxide that accounts for total catalyst weight 1.5～8%, it is characterized in that having added in the above-mentioned component amine that accounts for total catalyst weight 0.01～7%.
2, catalyzer according to claim 1 is characterized in that the amine that adds is ethamine, diethylamine, triethylamine, Trimethylamine 99, thanomin, diethanolamine or trolamine.
3, catalyzer according to claim 2 is characterized in that the amine that adds is triethylamine, Trimethylamine 99 or trolamine.
4, catalyzer according to claim 1, the amount that it is characterized in that adding amine is to account for 0.05～2% of total catalyst weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94112146A CN1043192C (en) | 1994-05-03 | 1994-05-03 | Catalyst for hydrogenation preparing bata-phenethyl alcohol from phenylethylene oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94112146A CN1043192C (en) | 1994-05-03 | 1994-05-03 | Catalyst for hydrogenation preparing bata-phenethyl alcohol from phenylethylene oxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1111169A CN1111169A (en) | 1995-11-08 |
| CN1043192C true CN1043192C (en) | 1999-05-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94112146A Expired - Fee Related CN1043192C (en) | 1994-05-03 | 1994-05-03 | Catalyst for hydrogenation preparing bata-phenethyl alcohol from phenylethylene oxide |
Country Status (1)
| Country | Link |
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| CN (1) | CN1043192C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106622332B (en) * | 2016-12-08 | 2019-07-23 | 万华化学集团股份有限公司 | A kind of Ni base catalyst and preparation method thereof being used to prepare bata-phenethyl alcohol |
| CN108264448B (en) | 2017-01-03 | 2019-08-06 | 万华化学集团股份有限公司 | A kind of reaction system preparing bata-phenethyl alcohol, catalyst and its process |
| CN107952483B (en) * | 2017-12-18 | 2020-07-28 | 万华化学集团股份有限公司 | Catalyst, reactor using the same, and method for preparing β -phenethyl alcohol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1475689A (en) * | 1974-06-07 | 1977-06-01 | Jowett P | Raney nickel hydrogenation catalyst |
| SU1055734A2 (en) * | 1979-07-24 | 1983-11-23 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Method for preparing beta-phenyl-ethyl alcohol |
-
1994
- 1994-05-03 CN CN94112146A patent/CN1043192C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1475689A (en) * | 1974-06-07 | 1977-06-01 | Jowett P | Raney nickel hydrogenation catalyst |
| SU1055734A2 (en) * | 1979-07-24 | 1983-11-23 | Всесоюзный научно-исследовательский институт синтетических и натуральных душистых веществ | Method for preparing beta-phenyl-ethyl alcohol |
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| Publication number | Publication date |
|---|---|
| CN1111169A (en) | 1995-11-08 |
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Granted publication date: 19990505 Termination date: 20100503 |