CN107089900B - Preparation method of β -phenethyl alcohol - Google Patents
Preparation method of β -phenethyl alcohol Download PDFInfo
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- CN107089900B CN107089900B CN201710296121.9A CN201710296121A CN107089900B CN 107089900 B CN107089900 B CN 107089900B CN 201710296121 A CN201710296121 A CN 201710296121A CN 107089900 B CN107089900 B CN 107089900B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
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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
- Y02P20/584—Recycling of catalysts
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Abstract
The invention provides a preparation method of β -phenethyl alcohol, which comprises the steps of adding a catalyst, water and benzyl alcohol, and introducing CO and H2Mixing the gases and reacting. The catalyst of the present invention has high activity, high selectivity and high conversion rate of benzyl alcohol>50%, β -Total selectivity to phenethyl alcohol and phenylacetaldehyde>90 percent. The invention uses water-soluble complex catalyst formed by water-soluble ruthenium, rhodium metal salt and water-soluble ligand to carry out the homologous reaction of benzyl alcohol in a water-oil two-phase system, and can obtain better activity and selectivity compared with the traditional cobalt-ruthenium homogeneous catalytic system. The water-oil two-phase reaction is convenient for post-treatment, the water-phase catalyst can be recycled, the environment is friendly, and the discharge of three wastes is less.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing β -phenethyl alcohol from benzyl alcohol.
Background
β -phenethyl alcohol (2-phenyl ethanol), which is aromatic alcohol with soft and delicate rose smell, is widely applied to rose type and other types of essence formulas, and is widely applied in the fields of medicine, food, daily chemicals and the like, and the consumption of β -phenethyl alcohol is about 2 ten thousand tons per year all over the world at present.
The method for synthesizing β -phenethyl alcohol in the prior art mainly comprises a halogen alcohol method, a benzene-ethylene oxide alkylation method and a styrene oxide hydrogenation method, wherein the benzene alcohol prepared by the benzene-ethylene oxide alkylation method has more impurities and is difficult to be used as spice.
The method for preparing β -phenethyl alcohol by benzyl alcohol has been reported in the past century, the document Irving Wender et al, J.Am.chem.Soc.71(1949),4160 4161 reports that the selectivity of 49 percent of toluene and 26 percent of phenethyl alcohol can be obtained by the reaction of benzyl alcohol and synthesis gas by using a cobalt catalyst for the first time, and the patent US4435605A reports that p-tolualdehyde can also be used as a raw material, and the p-methyl- β -phenethyl alcohol can be obtained by selecting a proper solvent through the homologation reaction of p-tolualdehyde and mixed gas under the system of cobalt, iodide and ruthenium, wherein the highest selectivity in the example is 63.6 percent.
Patent US4158100A reports the use of Co2(CO)8As catalysts, NaI and RuCl were used3As a cocatalyst, reaction conditions are optimized and inspected, the selectivity of β -phenethyl alcohol is greatly improved, and CO and H are reacted at 100-165 DEG C2Under the condition of 270 atm of mixed gas and the existence of a small amount of water, the selectivity of β -phenethyl alcohol can reach 80.0 percent at most, the selectivity of toluene is 10.5 percent, and the conversion rate of benzyl alcohol is 21.2 percent.
However, the patent does not report key technical information such as a reaction liquid post-treatment scheme, the recycling of the catalyst and the like.
The method has the advantages of simple reaction route, high requirement on equipment, complex catalyst system, difficult recycling of the catalyst, low selectivity of the catalyst, high production cost and high industrial application difficulty, and needs high-pressure reaction.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for preparing β -phenethyl alcohol from benzyl alcohol, which takes the benzyl alcohol as a raw material and is prepared by reacting the benzyl alcohol with CO and H2The mixed gas reacts to directly generate β -phenethyl alcohol, and the purposes of the invention are realized:
(1) the activity and the selectivity of the catalyst are high;
(2) the catalyst can be repeatedly used, and the production cost is low;
(3) the reaction pressure was reduced.
The reaction process is as follows:
in order to solve the problems, the invention adopts the following technical scheme:
a process for preparing β -phenylethyl alcohol includes adding catalyst, water and benzyl alcohol, introducing CO and H2Mixing the gases and reacting.
The following is a further improvement of the above technical solution:
adding a catalyst, water and benzyl alcohol, adding 1-10 parts of water, 0.01-0.1 part of catalyst and 1 part of benzyl alcohol into an autoclave, and performing nitrogen replacement three times and hydrogen replacement three times.
The mass ratio of the benzyl alcohol, the water and the catalyst is preferably as follows: 1:1.5: 0.015-0.046;
the catalyst is a water-soluble complex catalyst formed by metal salt and water-soluble ligand; the metal salt is ruthenium metal salt or rhodium metal salt or a mixture of the ruthenium metal salt and the rhodium metal salt.
The metal salt is one or more of ruthenium chloride, rhodium chloride, ruthenium bromide, rhodium bromide, triphenyl phosphorus dichlororuthenium and acetylacetonatocarbonylrhodium.
The water-soluble ligand is one or more of triphenylphosphine sodium trimetaphosphate (TPPTS), triphenylphosphine sodium bis-sulfonate (TPPDS), 1,3, 5-triaza-7-phosphamidoadamantane (TPA) and 1,1 '-binaphthyl-2, 2' -diphenyl phosphine sodium disulfonate (BINAPS).
The mass ratio of the metal salt to the water-soluble ligand is 1: 1-8.
Introducing CO and H2Heating the mixed gas to 50-160 ℃, and introducing CO/H2The mixed gas with the molar ratio of 1:1-3 is pressurized to 2-6MPa, and the mixed gas is continuously introduced to maintain the pressure of the system at 2-6 MPa.
The reaction is carried out at the temperature of 50-160 ℃ and the reaction pressure of 2-6 MPa.
The reaction temperature is preferably 130-160 ℃;
the reaction is carried out at a stirring speed of 200-1000 rpm for 3-30 h under pressure until the conversion rate of the benzyl alcohol is more than 50%, standing and layering are carried out after the reaction is finished, the water phase containing the catalyst is continuously applied to the next batch of reaction, the organic phase is a mixture of the benzyl alcohol, the phenethyl alcohol, the phenylacetaldehyde, the toluene and the like, the organic phase is separated by a rectifying tower to obtain β -phenethyl alcohol finished products, the unreacted benzyl alcohol is applied to the next batch of reaction, and the phenylacetaldehyde can be subjected to further hydrogenation reaction by using Raney nickel as the catalyst to obtain β -phenethyl alcohol.
The stirring speed is preferably 650-750 rpm, and the pressurized reaction time is preferably 8-24 h;
since phenylacetaldehyde can be subjected to further hydrogenation reaction using raney nickel as a catalyst to obtain β -phenylethyl alcohol,
the sum of the selectivities of β -phenethyl alcohol and phenylacetaldehyde may therefore represent the level of the process of the present invention.
Compared with the prior art, the invention has the following beneficial effects:
1. the catalyst has high activity and selectivity, the conversion rate of the benzyl alcohol is more than 50 percent, the total selectivity of β -phenethyl alcohol and phenylacetaldehyde is more than 90 percent, and the preferable effects are that the conversion rate of the benzyl alcohol is 57.61-68.12 percent, and the selectivity of β -phenethyl alcohol and phenylacetaldehyde is 90.29-95.22 percent.
The invention uses water-soluble complex catalyst formed by water-soluble ruthenium, rhodium metal salt and water-soluble ligand to carry out the homologous reaction of benzyl alcohol in a water-oil two-phase system, and can obtain better activity and selectivity compared with the traditional cobalt-ruthenium homogeneous catalytic system.
2. The water-oil two-phase reaction is convenient for post-treatment, the water-phase catalyst can be recycled, the environment is friendly, the discharge of three wastes is less, the water-phase catalyst can be recycled for 5 times, the total selectivity of β -phenethyl alcohol and phenylacetaldehyde has no obvious difference, and the conversion rate of the benzyl alcohol is only reduced by 5-6 percent.
3. The invention has low reaction pressure and low requirement on equipment.
4. The invention uses benzyl alcohol and mixed gas as raw materials, and the raw materials have wide sources and low price.
Detailed Description
EXAMPLE 1A method for the preparation of β -phenylethyl alcohol
The method comprises the following steps:
(1) adding catalyst, water and benzyl alcohol
Adding 1g of ruthenium chloride, 6.8g of triphenylphosphine sodium trimetaphosphate TPPTS and 300g of water into a 1000ml high-pressure kettle with magnetic stirring and a temperature controller; then, 200g of benzyl alcohol was added, and the mixture was replaced with nitrogen three times and then replaced with hydrogen three times.
(2) Introducing CO and H2Mixed gas (es)
Heating to 150 deg.C, CO/H2The mixed gas with the molar ratio of 1:2 is pressurized to 6.0MPa, and the mixed gas,
continuously introducing the mixture, and maintaining the pressure of the system at 6.0 MPa.
(3) Reaction of
Stirring at the rotating speed of 700rpm, sampling in the reaction process to analyze the reaction progress, cooling with water when the conversion rate of the benzyl alcohol is more than 60%, extruding out reaction liquid, standing for layering, continuously applying a catalyst-containing water phase to the next batch of reaction, and rectifying an organic phase to recover the benzyl alcohol, the phenethyl alcohol and the phenylacetaldehyde.
After 3h of reaction, the conversion rate of benzyl alcohol was 65.32% and the selectivity of β -phenethyl alcohol and phenylacetaldehyde was 95.10% as analyzed by gas chromatography.
EXAMPLE 2A method for producing β -phenylethyl alcohol
The method comprises the following steps:
(1) adding catalyst, water and benzyl alcohol
1g of rhodium chloride, 2.0g of 1,3, 5-triaza-7-phospha-adamantane TPA and 300g of water are added into a 1000ml autoclave with magnetic stirring and a temperature controller; then, 200g of benzyl alcohol was added, and the mixture was replaced with nitrogen three times and then replaced with hydrogen three times.
(2) Introducing CO and H2Mixed gas (es)
Heating to 150 deg.C, CO/H2The mixed gas with the molar ratio of 1:1 is pressurized to 4.0MPa, and the mixed gas is continuously introduced to maintain the pressure of the system at 4.0 MPa.
(3) Reaction of
Stirring at 700rpm, sampling in the reaction process, analyzing the conversion rate of the benzyl alcohol to be more than 60%, cooling with water, extruding out reaction liquid, standing for layering, continuously applying a catalyst-containing water phase to the next batch of reaction, and rectifying an organic phase to recover the benzyl alcohol and the phenethyl alcohol.
Through gas chromatographic analysis, after the reaction is carried out for 15 hours, the conversion rate of the benzyl alcohol is 68.12 percent, and the selectivity of β -phenethyl alcohol and phenylacetaldehyde is 91.22 percent.
EXAMPLE 3A method for producing β -phenylethyl alcohol
The method comprises the following steps:
(1) adding catalyst, water and benzyl alcohol
1g of rhodium acetylacetonate, 8.0g of 1.1 '-binaphthyl-2.2' -diphenylphosphine disulfonate BINAPS and 300g of water were added to a 1000ml autoclave with magnetic stirring and a temperature controller; then, 200g of benzyl alcohol was added, and the mixture was replaced with nitrogen three times and then replaced with hydrogen three times.
(2) Introducing CO and H2Mixed gas (es)
Heating to 100 deg.C, CO/H2The mixed gas with the molar ratio of 1:2 is pressurized to 6.0MPa, and the mixed gas is continuously introduced to maintain the pressure of the system at 6.0 MPa.
(3) Reaction of
Stirring at 700rpm, sampling in the reaction process, analyzing the conversion rate of the benzyl alcohol to be more than 60%, cooling with water, extruding out reaction liquid, standing for layering, continuously applying a catalyst-containing water phase to the next batch of reaction, and rectifying an organic phase to recover the benzyl alcohol and the phenethyl alcohol.
After 28h of reaction, the conversion of benzyl alcohol was 60.39% and the selectivity of β -phenethyl alcohol and phenylacetaldehyde was 95.22% by gas chromatography.
EXAMPLE 4A method for producing β -phenylethyl alcohol
The method comprises the following steps:
(1) adding catalyst, water and benzyl alcohol
0.5g of ruthenium chloride, 0.5g of rhodium chloride, 8.0g of 1.1 '-binaphthyl-2.2' -diphenylphosphine disulfonic acid BINAPS BINAPS and 300g of water are added to a 1000ml autoclave with magnetic stirring and a temperature controller; then, 200g of benzyl alcohol was added, and the mixture was replaced with nitrogen three times and then replaced with hydrogen three times.
(2) Introducing CO and H2Mixed gas (es)
Heating to 100 deg.C, CO/H2The mixed gas with the molar ratio of 1:3 is pressurized to 2.0MPa, and the mixed gas is continuously introduced, so that the pressure of the system is maintained to be 2.0 MPa.
(3) Reaction of
Stirring at 1000rpm, sampling in the reaction process, analyzing the conversion rate of the benzyl alcohol to be more than 60%, cooling with water, extruding out reaction liquid, standing for layering, continuously applying a catalyst-containing water phase to the next batch of reaction, and rectifying an organic phase to recover the benzyl alcohol and the phenethyl alcohol.
After 30h of reaction, the conversion rate of the benzyl alcohol was 66.24% and the selectivity of β -phenethyl alcohol and phenylacetaldehyde was 93.75% by gas chromatography analysis.
EXAMPLE 5A method for producing β -phenylethyl alcohol
The method comprises the following steps:
(1) adding catalyst, water and benzyl alcohol
2g of triphenylphosphine ruthenium dichloride, 7.2g of triphenylphosphine sodium disulfonate TPPDS and 300g of water are added into a 1000ml high-pressure kettle with magnetic stirring and a temperature controller; then, 200g of benzyl alcohol was added, and the mixture was replaced with nitrogen three times and then replaced with hydrogen three times.
(2) Introducing CO and H2Mixed gas (es)
Heating to 130 deg.C, CO/H2The mixed gas with the molar ratio of 1:2 is pressurized to 2.0MPa, and the mixed gas is continuously introduced, so that the pressure of the system is maintained to be 2.0 MPa.
(3) Reaction of
Stirring at 700rpm, sampling in the reaction process to analyze that the conversion rate of the benzyl alcohol is more than 60%, cooling with water, extruding reaction liquid, standing for layering, continuously applying a water phase containing a catalyst to the next batch of reaction, wherein an organic phase is a rectified and recovered benzyl alcohol and phenethyl alcohol, and after 24 hours of reaction, the conversion rate of the benzyl alcohol is 57.61%, the selectivity of β -phenethyl alcohol is 82.56%, and the total selectivity of β -phenethyl alcohol and phenylacetaldehyde is 90.29%.
The catalyst of example 5 was used repeatedly for 5 times under the reaction conditions described in example 5, and the results are shown in Table 1.
TABLE 1 conversion, selectivity for the use of the catalyst
Note: the data in Table 1 are for the use of PPh in example 53RuCl2TPPDS catalyst, temperature: 130 ℃ and a molar ratio CO/H2=1: 2 pressure P =2.0Mpa reaction time t =24h, GC analysis result.
The catalyst of example 1 was used, and the reaction conditions of example 1 were used while changing the reaction temperature, and the results are shown in Table 2.
TABLE 2 conversion, selectivity of the reaction at different temperatures
Note: the data in Table 2 are the molar ratio CO/H using RuCl3-TPPTS catalyst2Pressure P =6.0Mpa =1/2 pressure, reaction time t =8h, GC analysis result.
After 4 batches of different catalytic systems, the catalytic performances are shown in Table 3.
TABLE 3 conversion, selectivity of the catalytic reaction under different ligands
Note: the data in table 3 are using the metal molar ratio Ru: rh =1:1, metal salt: ligandsThe mass ratio is 1:8, the reaction temperature is: 140 ℃ and a molar ratio CO/H2=1: 2, pressure P =6.0Mpa, stirring at 1000rpm, reaction time t =20h and GC analysis results were sampled (other conditions were the same as in example 4).
The products prepared in examples 1-5 of the present invention, analyzed by gas chromatography, showed a conversion of benzyl alcohol of 57.61-68.12%, selectivity of β -phenethyl alcohol and phenylacetaldehyde of 90.29-95.22%, and selectivity of β -phenethyl alcohol of > 80%.
Unless otherwise specified, the proportions in the present invention are mass proportions, and the percentages are mass percentages.
The foregoing shows and describes the general principles and features of the present invention, together with the advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (6)
1. The preparation method of β -phenethyl alcohol is characterized by comprising the following steps
Adding catalyst, water and benzyl alcohol, introducing CO and H2Mixing gas and reacting;
the catalyst is a water-soluble complex catalyst formed by metal salt and water-soluble ligand; the metal salt is ruthenium metal salt or rhodium metal salt or a mixture of the ruthenium metal salt and the rhodium metal salt;
the metal salt is one or more of ruthenium chloride, rhodium chloride, ruthenium bromide, rhodium bromide, triphenyl phosphorus dichlororuthenium and acetylacetonatocarbonylrhodium;
the water-soluble ligand is one or more of triphenylphosphine sodium tri-meta-sulfonate, triphenylphosphine sodium di-sulfonate, 1,3, 5-triaza-7-phosphoadamantane and 1,1 '-binaphthyl-2, 2' -diphenyl phosphine sodium disulfonate.
2. The method for preparing β -phenethyl alcohol according to claim 1, wherein the step is carried out by
Adding a catalyst, water and benzyl alcohol, and adding 1-10 parts of water, 0.01-0.1 part of catalyst and 1 part of benzyl alcohol into the autoclave.
3. The method for preparing β -phenethyl alcohol according to claim 1, wherein the mass ratio of the metal salt to the water-soluble ligand is 1: 1-8.
4. The method for preparing β -phenylethyl alcohol according to claim 1, wherein CO and H are introduced2Mixing the gas, pressurizing to 2-6MPa, and mixing CO and H2The molar ratio of (A) to (B) is 1: 1-3.
5. The preparation method of β -phenethyl alcohol according to claim 1, wherein the reaction temperature is 50-160 ℃ and the reaction pressure is 2-6 MPa.
6. The method for preparing β -phenethyl alcohol according to claim 1, wherein the reaction is completed with a stirring speed of 200-1000 rpm and a pressurized reaction time of 3-30 h until the conversion rate of the phenethyl alcohol is more than 50%.
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Citations (7)
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| US4158100A (en) * | 1977-11-10 | 1979-06-12 | Chem Systems, Inc. | Process for the preparation of β-phenylethyl alcohol via homologation |
| EP0004732A1 (en) * | 1978-04-04 | 1979-10-17 | CHEM SYSTEMS, Inc. | Preparation of 2-phenylethanol and 2-phenylethyl acetate |
| JPS5640626A (en) * | 1979-09-12 | 1981-04-16 | Sumitomo Chem Co Ltd | Production of 2- p-methylphenyl ethanol |
| EP2377841A1 (en) * | 2008-12-11 | 2011-10-19 | Takasago International Corporation | Method for producing alcohol compound |
| CN103342627A (en) * | 2013-06-27 | 2013-10-09 | 山东新和成药业有限公司 | Method for selective hydrogenation synthesis of nerol and geraniol mixture by using citral in water-organic two-phase system |
| CN104387235A (en) * | 2014-11-21 | 2015-03-04 | 山东新和成药业有限公司 | Method for synthesizing prenol employing selective hydrogenation of 3-methylcrotonaldehyde |
| CN105175231A (en) * | 2015-09-22 | 2015-12-23 | 山东新和成药业有限公司 | Method for preparing allyl alcohol through selective hydrogenation of propargyl alcohol |
-
2017
- 2017-04-28 CN CN201710296121.9A patent/CN107089900B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4158100A (en) * | 1977-11-10 | 1979-06-12 | Chem Systems, Inc. | Process for the preparation of β-phenylethyl alcohol via homologation |
| EP0004732A1 (en) * | 1978-04-04 | 1979-10-17 | CHEM SYSTEMS, Inc. | Preparation of 2-phenylethanol and 2-phenylethyl acetate |
| JPS5640626A (en) * | 1979-09-12 | 1981-04-16 | Sumitomo Chem Co Ltd | Production of 2- p-methylphenyl ethanol |
| EP2377841A1 (en) * | 2008-12-11 | 2011-10-19 | Takasago International Corporation | Method for producing alcohol compound |
| CN103342627A (en) * | 2013-06-27 | 2013-10-09 | 山东新和成药业有限公司 | Method for selective hydrogenation synthesis of nerol and geraniol mixture by using citral in water-organic two-phase system |
| CN104387235A (en) * | 2014-11-21 | 2015-03-04 | 山东新和成药业有限公司 | Method for synthesizing prenol employing selective hydrogenation of 3-methylcrotonaldehyde |
| CN105175231A (en) * | 2015-09-22 | 2015-12-23 | 山东新和成药业有限公司 | Method for preparing allyl alcohol through selective hydrogenation of propargyl alcohol |
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