CN85100462A - A kind of catalyst that can be used for the synthetic raspberry ketone of normal temperature and pressure - Google Patents
A kind of catalyst that can be used for the synthetic raspberry ketone of normal temperature and pressure Download PDFInfo
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- CN85100462A CN85100462A CN 85100462 CN85100462A CN85100462A CN 85100462 A CN85100462 A CN 85100462A CN 85100462 CN85100462 CN 85100462 CN 85100462 A CN85100462 A CN 85100462A CN 85100462 A CN85100462 A CN 85100462A
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- catalyst
- catalytic hydrogenation
- hydrogenation
- palladium
- raspberry ketone
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Abstract
A kind of can be used for
Catalytic hydrogenation and synthesizing
Description
The present invention relates to a kind of catalytic hydrogenation catalyst.
Raspberry ketone (HO
CH
2CH
2COCH
3) be a kind of spices that is used for foods and cosmetics, be one of important composition of Rubus idaeus volatile oil.Its synthetic route is more.But obtain industrialized synthetic route at present is to use monohydroxy phenyl aldehyde and condensation of acetone are made HO
CH=CHCOCH
3, make latter's shortening then and synthetic raspberry ketone (as Soviet Union's document: A.C761451(CCCP) .N.1980 NO 33).Its reaction process is as follows:
The first step (aldehyde ketone condensation) of reaction is carried out easily, but when second went on foot shortening, (temperature was 130 ℃～160 ℃, and pressure is 100～120kg/cm must to use high temperature, high pressure
2), could obtain productive rate preferably.
In order to solve the difficulty on above-mentioned technology and the equipment and to simplify the raspberry ketone that technological operation Guo Cheng And obtains high yield, we adopt 5% Pd/C catalyst (palladium one carbon catalyst) to make hydrogenation catalyst, use dehydrated alcohol (or industrial alcohol) to make solvent, make HO
CH=CHCOCH
3Hydrogenation can carry out at normal temperatures and pressures, and the productive rate of hydrogenated products reaches 94.4%(by beta-unsaturated ketone).We have done the experiment of a series of exploration Pd/C catalyst consumptions earlier: 16 gram beta-unsaturated ketone (HO
-CH=CHCOCH
3), 100 milliliters of dehydrated alcohols add in the reaction unit, after the 5%Pd/C catalyst that add different amounts then carried out hydrogenation, the relation of the productive rate of its raspberry ketone and the consumption of catalyst was as shown in table 1:
Table 1: the relation of catalyst consumption and raspberry ketone productive rate
| Numbering | 5%Pd/C catalyst consumption (g) | Raspberry ketone productive rate (press beta-unsaturated ketone and calculate %) |
| 1 | 1 | 90.7 |
| 2 | 2 | 93.2 |
| 3 | 4 | 94.4 |
| 4 | 6 | 94.4 |
As known from Table 1, the consumption of 5%Pd/C catalyst be 1-6 gram all can, but optimum quantity is the 4-6 gram.In order to observe the influence of hydrogenation solvent to the product productive rate, we are fixed as 4 grams, reaction raw materials HO to the consumption of 5%Pd/C catalyst
-CH=CHCOCH
3Consumption be fixed as 16 grams, but use the dehydrated alcohol or the industrial spirit (95% ethanol) of different amounts, with the influence of examination ethanol consumption and quality, result such as table 2 to product yield
Table 2: hydrogenation solvent is to the influence of hydrogenated products yield
| Numbering | Solvent | Hydrogenation ratio |
| 1 | Dehydrated alcohol 50ml | 92.0 |
| 2 | Dehydrated alcohol 100ml | 92.6 |
| 3 | 95% ethanol 100ml | 92.6 |
As seen from Table 2, use dehydrated alcohol and use 95% ethanol to not influence of product yield; The ethanol consumption is little to the influence of product yield.So the employing weight percentage is that the amount of alcohol of 78-85% is suitable.So the proportioning of material can be defined as: the weight percentage of beta-unsaturated ketone is 16%, and the dehydrated alcohol consumption is 78-85%, and the consumption of 5%Pd/C catalyst is 1-6%.
Use this catalyst to carry out HO-
-CH=CHCOCH
3Shortening and prepare HO
-CH
2CH
2COCH
3Can react at normal temperatures and pressures, obtaining productive rate is that 94.4%(is by beta-unsaturated ketone) product, the catalytic hydrogenation process that uses this catalyst to carry out is simple, and is easy to operate, the hydrogenation solvent price is low, the raw material of making catalyst also obtains easily.We have carried out the analysis of hydrocarbon element to the test ， And that product has carried out nucleus magnetic resonance, infrared spectra again.Fig. 1 is an infrared spectrogram, and the C=O absorption band of product is at 1700Cm
-1The place; Fig. 2 is the NMR spectrogram of product.Product of the same race with American I FF company compares, and its IR figure and NMR spectrogram (Fig. 3 and Fig. 4) are consistent basically.And the H of product, C results of elemental analyses also conform to (table 3) with theoretical value.
Table 3: the raspberry ketone that makes with this catalyst
The C-H results of elemental analyses
Preparation method and application thereof for this catalyst is described are exemplified below:
Example 1
41 gram Palladous chlorides are dissolved in 10ml concentrated hydrochloric acid and the 25ml water, and the activated carbon thorough mixing with 70ml water dilution back and 46 grams have been handled well adds 200ml distilled water again, carries out hydro-reduction with hydrogenation apparatus, till hydrogen no longer is absorbed.Catalyzer is leached, be washed till neutrality, wash with dehydrated alcohol again, wash with anhydrous diethyl ether at last with distilled water.Put into the vacuum drier inner drying behind the suction filtration and promptly obtain 5% Pd/C catalyst.
Example 2
With 50ml anhydrous alcohol solution 16 gram beta-unsaturated ketone (HO-
-CH=CHCOCH
3) And puts into constant pressure funnel.The Pd/C catalyst of 50ml dehydrated alcohol and 4 grams 5% is put into reaction flask, check with 3-4 And of nitrogen washing reaction system whether gas leakage part (answering good seal if air-leak section is arranged) is arranged.And then wash 3-4 time with hydrogen, to catch up with net air, feed hydrogen gas And the beta-unsaturated ketone solution in the dropping funnel is put into reaction flask rapidly, start induction stirring, carry out the catalytic hydrogenation of normal temperature and pressure, till hydrogen no longer is absorbed.Inhaling the hydrogen time is 4 hours, and hydrogen is 2880ml.Turn off the hydrogen valve, carry out suction filtration, the catalyst that reclaims with absolute ethanol washing 3 times, it is standby to put into vacuum drier then immediately.Mother liquor is steamed ethanol, carry out underpressure distillation again, collect 158 ℃/1mmHg fraction, obtain 15.3 gram white solids.Hydrogenation ratio is that 94.4%(is in beta-unsaturated ketone).Hydrogenation apparatus is seen Fig. 5, and its drawing is described as follows:
1. nitrogen steel cylinder
2. hydrogen gas cylinder
3. tubualted bottle (being used for hydrogen is pressed in the reaction system)
4. eudiometer (being used for measuring hydrogen volume)
5. surge flask
6. reaction flask
7. induction stirring
8. hydrogen tail gas outlet unit
9. constant pressure funnel
Claims (5)
1, a kind of can being used for from HO-
-CH=CH-CO-CH
3Preparation HO-
-CH
2-CH
2COCH
3The catalytic hydrogenation catalyst of (raspberry ketone) is characterized in that it is to make carrier with activated carbon, sneaks into 5% palladium composition.
2, the method for a kind of preparation 5% palladium one carbon catalyst is characterized in that Palladous chloride is dissolved in 1: 2.5 the hydrochloric acid, with the activated carbon thorough mixing, carries out hydro-reduction with hydrogenation apparatus again and makes behind the dilute with water.
3, a kind of can be from HO-
-CH=CHCOCH
3Synthetic HO-
-CH
2CH
2COCH
3Catalytic hydrogenation, it is characterized in that it is to adopt palladium one carbon (Pd/C) to make catalyst, make solvent with dehydrated alcohol, under normal temperature and pressure, carry out catalytic hydrogenation.
4, according to the said catalytic hydrogenation of claim 3, it is characterized in that used Pd/C catalyst, be to make carrier with activated carbon, sneak into 5% palladium and form.
5, according to the said catalytic hydrogenation of claim 4, the weight percentage of the catalyst of employed Pd/C is 1-6% when it is characterized in that hydrogenation, used HO-
-CH=CHCOCH
3Weight percentage be 16%, the weight percentage of dehydrated alcohol is 78-85%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85100462A CN85100462B (en) | 1985-04-03 | 1985-04-03 | Rubus idaeus west synthetic method together |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85100462A CN85100462B (en) | 1985-04-03 | 1985-04-03 | Rubus idaeus west synthetic method together |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85100462A true CN85100462A (en) | 1985-11-10 |
| CN85100462B CN85100462B (en) | 1988-04-13 |
Family
ID=4791176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85100462A Expired CN85100462B (en) | 1985-04-03 | 1985-04-03 | Rubus idaeus west synthetic method together |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN85100462B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159695A (en) * | 2011-12-08 | 2013-06-19 | 首都师范大学 | Thiazole compound capable of restraining human immunodeficiency virus (HIV) replication and effective against drug-resistant HIV virus strains and preparation method and purpose thereof |
-
1985
- 1985-04-03 CN CN85100462A patent/CN85100462B/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159695A (en) * | 2011-12-08 | 2013-06-19 | 首都师范大学 | Thiazole compound capable of restraining human immunodeficiency virus (HIV) replication and effective against drug-resistant HIV virus strains and preparation method and purpose thereof |
| CN103159695B (en) * | 2011-12-08 | 2015-08-12 | 首都师范大学 | HIV can be suppressed to copy and to effective thiazole compound of resistance HIV virus strain and its production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| CN85100462B (en) | 1988-04-13 |
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