CN107089900A - A kind of preparation method of β benzyl carbinols - Google Patents
A kind of preparation method of β benzyl carbinols Download PDFInfo
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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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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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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- 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
- C07C29/132—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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- 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
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- 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
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Abstract
The present invention provides a kind of preparation method of β benzyl carbinols, the preparation method, including adds catalyst, water, phenmethylol, is passed through CO, H2Gaseous mixture, reaction.Catalyst activity of the present invention, selectivity are high, phenmethylol conversion ratio>The overall selectivity of 50%, β benzyl carbinol and phenylacetaldehyde>90%.The present invention carries out the homologation of phenmethylol using the water soluble complex catalyst of Water-soluble Ru, rhodium metal salt and water soluble ligand formation under water phase and an oil phase system, and more preferable activity and selectivity can be obtained than traditional cobalt ruthenium homogeneous catalysis system.Water phase and an oil phase is reacted, and convenient post-treatment, aqueous phase catalyst can realize recycled, and environment-friendly, and three waste discharge is few.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of method that bata-phenethyl alcohol is prepared by phenmethylol.
Background technology
Bata-phenethyl alcohol（2- phenylethanols）, it is a kind of aromatic alcohol with soft fine and smooth rose scent, is widely used in rose
In rare type and other kinds of composition, it is widely used in fields such as medicine, food and daily use chemicals, the current whole world is to β-benzene second
The consumption of alcohol is about 20,000 tons/year.
The method of synthesis bata-phenethyl alcohol mainly has halogenohydrin method, benzene-oxirane alkylation process and Oxybenzene in the prior art
Ethylene hydrogenation method.The benzyl carbinol impurity that wherein prepared by benzene-oxirane alkylation process is more, it is difficult to used as spices.Halogenohydrin
Method and styrene oxide hydrogenation method are the methods of industrially conventional production bata-phenethyl alcohol.There is step complexity in current halogenohydrin method,
Waste water abraum salt amount is big, the problems such as equipment corrosion is serious；Styrene oxide hydrogenation method is related to oxidation and hydrogenation technique, and oxidizing process makes
With substantial amounts of hydrogen peroxide or organic peroxide, process safety risk is big, product yield is low.
The method last century for preparing bata-phenethyl alcohol using phenmethylol just has been reported that.Document Irving Wender et al.,
J.Am.Chem.Soc.71 (1949), 4160-4161 are reported first uses Co catalysts, and phenmethylol can be obtained with synthesis gas reaction
To the selectivity of toluene 49% and benzyl carbinol 26%.Patent US4435605A reports can also be used p-tolyl aldehyde to be raw material,
Under cobalt, iodide and ruthenium system, by selecting suitable solvent, the homologation through p-tolualdehyde and gaseous mixture is compared with Gao Xuan
Selecting property is obtained to methyl-bata-phenethyl alcohol, and highest is selectively 63.6% in embodiment.
Patent US4158100A reports use Co2(CO)8As catalyst, NaI and RuCl are used3As co-catalyst, and
Optimization has been done to reaction condition to investigate, and the selectivity of bata-phenethyl alcohol greatly improved, at 100~165 DEG C, CO and H2Gaseous mixture
Under 270 (atm), in the presence of a small amount of water, the selectivity of bata-phenethyl alcohol reaches as high as 80.0%, methylbenzene selective 10.5%, phenmethylol
Conversion ratio be 21.2%.
But the key technology information such as reaction solution post processing scheme, the recycled of catalyst are not reported in patent.
The advantage of this method is that reaction scheme is simple, has the disadvantage to need reaction under high pressure, catalyst system high to equipment requirement
Complexity, the recovery of catalyst is difficult to, and the selectivity of catalyst is low, the substantial amounts of toluene of by-product, and production cost is high, industry
It is big using difficulty.
The content of the invention
In view of the shortcomings of the prior art, the present invention provides a kind of method that bata-phenethyl alcohol is prepared by phenmethylol, with phenmethylol
For raw material, by with CO and H2Mixing solid/liquid/gas reactions, directly generate bata-phenethyl alcohol；Realize following goal of the invention：
（1）The activity and selectivity of catalyst is high；
（2）Catalyst is repeatable to be applied mechanically, and production cost is low；
（3）Reduce reaction pressure.
Course of reaction is as follows：
To solve the above problems, the present invention uses following technical scheme：
A kind of preparation method of bata-phenethyl alcohol, the preparation method, including catalyst, water, phenmethylol are added, it is passed through CO, H2It is mixed
Close gas, reaction.
The following is the further improvement to above-mentioned technical proposal：
The addition catalyst, water, phenmethylol, height is added to by 1~10 part of water and 0.01~0.1 part of catalyst, 1 part of phenmethylol
Press in kettle, nitrogen displacement three times, hydrogen is replaced three times.
The phenmethylol, water, the mass ratio of catalyst are preferably：1:1.5:0.015-0.046；
The catalyst, is metal salt and the water soluble complex catalyst of water soluble ligand formation；The metal salt, is ruthenium gold
Belong to the mixture of salt or rhodium metal salt or both.
The metal salt, is ruthenic chloride, radium chloride, ruthenium bromide, bromination rhodium, triphenyl phosphorus dichloro ruthenium, acetylacetone,2,4-pentanedione carbonyl
One or more in rhodium.
The water soluble ligand, is three sodium sulfonates of triphenylphosphine（TPPTS）, two sodium sulfonates of triphenylphosphine（TPPDS）、
Azepine -7- the phosphorus of 1,3,5- tri- is for adamantane（TPA）, 1,1 '-dinaphthalene -2,2'- diphenyl phosphine disulfonic acid sodium（BINAPS）In one kind
Or it is a variety of.
The mass ratio of the metal salt and water soluble ligand, is 1:1-8.
It is described to be passed through CO, H2Gaseous mixture, is heated to 50-160 DEG C, is passed through CO/H2Mol ratio be 1:1-3 gaseous mixture adds
2-6MPa is depressed into, the gaseous mixture is continually fed into, maintains the pressure of system in 2-6MPa.
The reaction, 50~160 DEG C of reaction temperature, reaction pressure is 2-6MPa.
The reaction temperature is preferably 130-160 DEG C；
The reaction, speed of agitator is 200~1000rpm, and the compressive reaction time is 3~30h, until phenmethylol conversion ratio ＞
50%, after reaction terminates, stratification, the aqueous phase containing catalyst continues set and uses lower batch reaction, and organic phase is phenmethylol, benzene second
The mixtures such as alcohol, phenylacetaldehyde and toluene, the complete benzene first of bata-phenethyl alcohol finished product, unreacted is obtained after organic phase is crossed into rectifying column separation
Alcohol set uses lower batch reaction, and phenylacetaldehyde can be used Raney's nickel as the further hydrogenation reaction of catalyst progress and obtain bata-phenethyl alcohol.
The speed of agitator, preferably 650-750 rpm, the compressive reaction time is preferably 8-24h；
Because phenylacetaldehyde, which Raney's nickel can be used to carry out further hydrogenation reaction as catalyst, obtains bata-phenethyl alcohol,
Therefore the selective sum of bata-phenethyl alcohol and phenylacetaldehyde can represent the level of present invention process.
Compared with prior art, the invention has the advantages that：
1st, catalyst activity of the present invention, selectivity are high, phenmethylol conversion ratio>50%, the overall selectivity of bata-phenethyl alcohol and phenylacetaldehyde>
90%；It is preferred that effect be that the conversion ratio of phenmethylol is 57.61-68.12%, the selectivity of bata-phenethyl alcohol and phenylacetaldehyde is 90.29-
95.22%。
The present invention is using the water soluble complex catalyst of Water-soluble Ru, rhodium metal salt and water soluble ligand formation in water oil
The homologation of phenmethylol is carried out under two-phase system, more preferable activity can be obtained than traditional cobalt-ruthenium homogeneous catalysis system
And selectivity.
2nd, water phase and an oil phase is reacted, and convenient post-treatment, aqueous phase catalyst can realize recycled, and environment-friendly, the three wastes
Discharge is few, aqueous phase catalyst recycled 5 times, and the overall selectivity of bata-phenethyl alcohol and phenylacetaldehyde is without significant difference, phenmethylol conversion
Rate only reduces 5-6 percentage points.
3rd, present invention reaction, pressure is low, not high to equipment requirement.
4th, the present invention is raw material using phenmethylol, gaseous mixture, and raw material sources are extensively, cheap.
Embodiment
A kind of preparation method of the bata-phenethyl alcohol of embodiment 1
Comprise the following steps：
（1）Add catalyst, water, phenmethylol
Sodium sulfonate TPPTS, 300g water between 1g ruthenic chlorides and 6.8g triphenylphosphines three is added to magnetic agitation and temperature controller
1000ml autoclaves in；Then 200g phenmethylols are added, with nitrogen displacement three times, after replaced three times with hydrogen.
（2）It is passed through CO, H2Gaseous mixture
It is heated to 150 DEG C, CO/H2Mol ratio be 1:2 gaseous mixture is forced into 6.0MPa, the gaseous mixture,
It is continually fed into, maintains the pressure of system in 6.0MPa.
（3）Reaction
700rpm rotating speed stirring, course of reaction sampling analysis reaction carry out situation, when phenmethylol conversion ratio is more than 60%, is used
Water cooling, extrudes reaction solution, stratification, and the aqueous phase containing catalyst can continue set and use lower batch reaction, and organic phase is to go rectifying
Reclaim phenmethylol, benzyl carbinol and phenylacetaldehyde.
Through gas chromatographic analysis, react after 3h, the conversion ratio of phenmethylol is 65.32%, the selection of bata-phenethyl alcohol and phenylacetaldehyde
Property 95.10%.
A kind of preparation method of the bata-phenethyl alcohol of embodiment 2
Comprise the following steps：
（1）Add catalyst, water, phenmethylol
1g radium chlorides and the azepine -7- phosphorus of 2.0g1,3,5- tri- are added to magnetic agitation and temperature for adamantane TPA, 300g water
In the 1000ml autoclaves for controlling device；Then 200g phenmethylols are added, with nitrogen displacement three times, after replaced three times with hydrogen.
（2）It is passed through CO, H2Gaseous mixture
It is heated to 150 DEG C, CO/H2Mol ratio be 1:1 gaseous mixture is forced into 4.0MPa, and the gaseous mixture is continually fed into, dimension
The pressure of system is held in 4.0MPa.
（3）Reaction
700rpm is stirred, and course of reaction sampling analysis phenmethylol conversion ratio is more than 60%, is water-cooled, and extrudes reaction solution, is stood and is divided
Layer, the aqueous phase containing catalyst can continue set and use lower batch reaction, and organic phase is to go rectifying to reclaim phenmethylol and benzyl carbinol.
Through gas chromatographic analysis, react after 15h, the conversion ratio of phenmethylol is 68.12%, the choosing of bata-phenethyl alcohol and phenylacetaldehyde
Selecting property 91.22%.
A kind of preparation method of the bata-phenethyl alcohol of embodiment 3
Comprise the following steps：
（1）Add catalyst, water, phenmethylol
1g acetylacetone,2,4-pentanediones rhodium carbonyl and 8.0g1.1 '-dinaphthalene -2.2'- diphenyl phosphine disulfonic acid sodium BINAPS, 300g water are added to
In 1000ml autoclaves with magnetic agitation and temperature controller；Then 200g phenmethylols are added, with nitrogen displacement three times, after use hydrogen
Gas is replaced three times.
（2）It is passed through CO, H2Gaseous mixture
It is heated to 100 DEG C, CO/H2Mol ratio be 1:2 gaseous mixture is forced into 6.0MPa, and the gaseous mixture is continually fed into, dimension
The pressure of system is held in 6.0MPa.
（3）Reaction
700rpm is stirred, and course of reaction sampling analysis phenmethylol conversion ratio is more than 60%, is water-cooled, and extrudes reaction solution, is stood and is divided
Layer, the aqueous phase containing catalyst can continue set and use lower batch reaction, and organic phase is to go rectifying to reclaim phenmethylol and benzyl carbinol.
Through gas chromatographic analysis, react after 28h, the conversion ratio of phenmethylol is 60.39%, the choosing of bata-phenethyl alcohol and phenylacetaldehyde
Selecting property 95.22%.
A kind of preparation method of the bata-phenethyl alcohol of embodiment 4
Comprise the following steps：
（1）Add catalyst, water, phenmethylol
0.5g ruthenic chlorides, 0.5g radium chlorides and 8.0g1.1 '-dinaphthalene -2.2'- diphenyl phosphine disulfonic acid sodium BINAPS, 300g water are added
Enter into the 1000ml autoclaves with magnetic agitation and temperature controller；Then 200g phenmethylols are added, with nitrogen displacement three times, after
Replaced three times with hydrogen.
（2）It is passed through CO, H2Gaseous mixture
It is heated to 100 DEG C, CO/H2Mol ratio be 1:3 gaseous mixture is forced into 2.0MPa, and the gaseous mixture is continually fed into, dimension
The pressure of system is held in 2.0MPa.
（3）Reaction
1000rpm is stirred, and course of reaction sampling analysis phenmethylol conversion ratio is more than 60%, is water-cooled, and extrudes reaction solution, is stood
Layering, the aqueous phase containing catalyst can continue set and use lower batch reaction, and organic phase is to go rectifying to reclaim phenmethylol and benzyl carbinol.
Through gas chromatographic analysis, react after 30h, the conversion ratio of phenmethylol is 66.24%, the choosing of bata-phenethyl alcohol and phenylacetaldehyde
Selecting property 93.75%.
A kind of preparation method of the bata-phenethyl alcohol of embodiment 5
Comprise the following steps：
（1）Add catalyst, water, phenmethylol
Sodium sulfonate TPPDS, 300g water between 2g triphenylphosphine dichloro rutheniums and 7.2g triphenylphosphines two is added to magnetic agitation
In the 1000ml autoclaves of temperature controller；Then 200g phenmethylols are added, with nitrogen displacement three times, after replaced three times with hydrogen.
（2）It is passed through CO, H2Gaseous mixture
It is heated to 130 DEG C, CO/H2Mol ratio be 1:2 gaseous mixture is forced into 2.0MPa, and the gaseous mixture is continually fed into, dimension
The pressure of system is held in 2.0MPa.
（3）Reaction
700rpm is stirred, and course of reaction sampling analysis phenmethylol conversion ratio is more than 60%, is water-cooled, and extrudes reaction solution, is stood and is divided
Layer, the aqueous phase containing catalyst can continue set and use lower batch reaction, and organic phase is to go rectifying to reclaim phenmethylol and benzyl carbinol.Through gas phase
After chromatography, reaction 24h, the conversion ratio of phenmethylol is 57.61%, and the selectivity of bata-phenethyl alcohol is 82.56%, bata-phenethyl alcohol and
The overall selectivity 90.29% of phenylacetaldehyde.
The catalyst of embodiment 5 is applied mechanically, applies mechanically 5 times, using the reaction condition described in embodiment 5, the results are shown in Table
1。
Conversion ratio that the catalyst of table 1. is applied mechanically, selection implementations
Note：In table 1 data be embodiment 5 in use PPh3RuCl2- TPPDS catalyst, temperature：130 DEG C, mol ratio CO/H2=1：
2 pressure P=2.0Mpa reaction time t=24h, GC analysis results.
By catalyst in embodiment 1, applied mechanically, using the reaction condition described in embodiment 1, only change the temperature of reaction
Degree, the results are shown in Table 2.
The conversion ratio that is reacted under the different temperatures of table 2., selection implementations
Note：Data are to use RuCl3-TPPTS catalyst, mol ratio CO/H in table 22=1/2 pressure P=6.0Mpa, reaction time
T=8h, GC analysis result.
Different catalyst system and catalyzings is applied mechanically after 4 batches, and catalytic performance is shown in Table 3.
The conversion ratio of catalytic reaction, selection implementations under the different ligands of table 3.
Note：Data are to compare Ru using metal molar in table 3：Rh=1:1, metal salt：It is 1 with body mass ratio:8, reaction temperature：140
DEG C, mol ratio CO/H2=1：2, pressure P=6.0Mpa, 1000rpm are stirred, reaction time t=20h sampling GC analysis results（Other
Condition is same as Example 4）.
Product prepared by 1-5 of the embodiment of the present invention, through gas chromatographic analysis, the conversion ratio of phenmethylol is 57.61-68.12%, β-
The selectivity of benzyl carbinol and phenylacetaldehyde is 90.29-95.22%, the selectivity of bata-phenethyl alcohol>80%.
Unless specifically indicated, ratio of the present invention is mass ratio, described percentage, is quality percentage
Than.
The general principle and principal character and advantages of the present invention of the present invention has been shown and described above.The skill of the industry
Art personnel are it should be appreciated that the present invention is not limited to the above embodiments, and described in above-described embodiment and specification is explanation
The principle of the present invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these
Changes and improvements all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent thereof.
Claims (9)
1. a kind of preparation method of bata-phenethyl alcohol, it is characterised in that：The preparation method, including add catalyst, water, benzene first
Alcohol, is passed through CO, H2Gaseous mixture, reaction.
2. a kind of preparation method of bata-phenethyl alcohol according to claim 1, it is characterised in that：It is described
Catalyst, water, phenmethylol are added, 1~10 part of water and 0.01~0.1 part of catalyst, 1 part of phenmethylol are added to autoclave
In.
3. a kind of preparation method of bata-phenethyl alcohol according to claim 2, it is characterised in that：
The catalyst, is metal salt and the water soluble complex catalyst of water soluble ligand formation；The metal salt, is ruthenium gold
Belong to the mixture of salt or rhodium metal salt or both.
4. a kind of preparation method of bata-phenethyl alcohol according to claim 3, it is characterised in that：
The metal salt, in being ruthenic chloride, radium chloride, ruthenium bromide, bromination rhodium, triphenyl phosphorus dichloro ruthenium, acetylacetone,2,4-pentanedione rhodium carbonyl
One or more.
5. a kind of preparation method of bata-phenethyl alcohol according to claim 3, it is characterised in that：The water soluble ligand, be
Three sodium sulfonates of triphenylphosphine, two sodium sulfonates of triphenylphosphine, the azepine -7- phosphorus of 1,3,5- tri- for adamantane, 1,1 '-dinaphthalene -2,
One or more in 2'- diphenyl phosphine disulfonic acid sodium.
6. a kind of preparation method of bata-phenethyl alcohol according to claim 3, it is characterised in that：The metal salt and water solubility
The mass ratio of part, is 1:1-8.
7. a kind of preparation method of bata-phenethyl alcohol according to claim 1, it is characterised in that：It is described to be passed through CO, H2Mixing
Gas, is forced into 2-6MPa, CO and H2Mol ratio be 1:1-3.
8. a kind of preparation method of bata-phenethyl alcohol according to claim 1, it is characterised in that：The reaction, reaction temperature
50~160 DEG C, reaction pressure is 2-6 MPa.
9. a kind of preparation method of bata-phenethyl alcohol according to claim 1, it is characterised in that：The reaction, speed of agitator
For 200~1000rpm, the compressive reaction time is 3~30h, and until phenmethylol conversion ratio ＞ 50%, reaction terminates.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108164394A (en) * | 2018-01-22 | 2018-06-15 | 台州泰捷化工科技有限公司 | A kind of preparation method of medication chemistry bata-phenethyl alcohol |
| CN108218670A (en) * | 2018-01-22 | 2018-06-29 | 台州泰捷化工科技有限公司 | A kind of preparation method of medication chemistry bata-phenethyl alcohol |
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| CN108164394A (en) * | 2018-01-22 | 2018-06-15 | 台州泰捷化工科技有限公司 | A kind of preparation method of medication chemistry bata-phenethyl alcohol |
| CN108218670A (en) * | 2018-01-22 | 2018-06-29 | 台州泰捷化工科技有限公司 | A kind of preparation method of medication chemistry bata-phenethyl alcohol |
| CN108218670B (en) * | 2018-01-22 | 2020-11-20 | 台州泰捷化工科技有限公司 | Preparation method of beta-phenethyl alcohol for pharmaceutical chemicals |
| CN108164394B (en) * | 2018-01-22 | 2021-02-12 | 上海凌凯医药科技有限公司 | Preparation method of beta-phenethyl alcohol for pharmaceutical chemicals |
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