CN106673952A - Method for catalytic synthesis of benzyl toluene by activated clay-loaded ferric trichloride (FeCl3) solid acid catalyst - Google Patents
Method for catalytic synthesis of benzyl toluene by activated clay-loaded ferric trichloride (FeCl3) solid acid catalyst Download PDFInfo
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- CN106673952A CN106673952A CN201611155177.4A CN201611155177A CN106673952A CN 106673952 A CN106673952 A CN 106673952A CN 201611155177 A CN201611155177 A CN 201611155177A CN 106673952 A CN106673952 A CN 106673952A
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- toluene
- benzyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
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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
Abstract
The invention relates to a method for catalytic synthesis of benzyl toluene by an activated clay-loaded ferric trichloride (FeCl3) solid acid catalyst. The method comprises the following steps: adding calcium-based bentonite with concentrated sulfuric acid, performing backflow stirring and drying to obtain solid activated clay; dissolving the FeCl3 in an acetonitrile solution, adding the prepared activated clay, stirring for 24 hours at a room temperature, filtering and activating at a temperature of 120 DEG C to obtain the activated clay-loaded FeCl3 solid acid catalyst; adding the activated clay-loaded FeCl3 solid acid catalyst in an alkylation reaction system of benzyl chloride and toluene for catalytic reaction, filtering and recovering the catalyst; performing reduced-pressure distillation and refinement on a benzyl toluene crude product to obtain benzyl toluene. The method provided by the invention has the advantages that the catalyst is rich in raw material source, low in cost, simple in preparation process, low in energy consumption due to no need of high temperature activation and easy for separation from the product; when the catalyst is used for the synthetic reaction of the benzyl toluene, the reaction conversion rate is high, the selectivity is strong, conditions are mild, the equipment corrosion is low, the catalyst is easy to recover and can be reused, and the environment pollution is less, so that the application prospect is wide.
Description
Technical field
The invention belongs to organic synthesis field, it is related to a kind of preparation method of benzyl toluene, more particularly to a kind of activity is white
The method that the ferric trichloride solid acid catalyst of soil load catalyzes and synthesizes benzyl toluene.
Background technology
Benzyl toluene mainly includes monobenzyl toluene (Monobenzyl Toluene, be abbreviated as MBT) and double benzyl toluenes
Two kinds of (Dibenzyl Toluene, be abbreviated as DBT).Industrially, monobenzyl toluene and double benzyl toluenes press 3:1 mixing can be used as
The insulating oil of power capacitor, trade name C101.Because C101 has the excellent properties for being adapted to make full film power capacitor
And feature, thus in industry used more and more widely.Single, double benzyl toluene can be additionally used in SAS series electric capacitors
The preparation of device insulating oil, and industrially used as excellent heat carrier.Therefore, the application prospect of benzyl toluene is very wide
It is wealthy.
At present, production benzyl toluene is the product that toluene is obtained with benzyl chloride reaction in the presence of acidic, is used
Catalyst mainly have：Lewis acid (AlCl3, BF3, TiCl4, FeCl3Deng) and Bronsted acid (HF, H2SO4, H3PO4Deng) two classes.CN
The synthetic method of the monobenzyl toluene of 90110008.0 low chlorine content and double benzyl toluenes, the method uses ferric trichloride
FeCl3Carry out catalyzing and synthesizing for benzyl toluene.These traditional homogeneous catalysts all exist separated with product difficult, catalyst without
Method recycle, equipment corrosion is serious, accessory substance is more, poor selectivity shortcoming, can produce in process of production a large amount of waste water and
Unserviceable accessory substance, causes serious environmental pollution and the wasting of resources.Therefore, research and develop selectivity height, be easily isolated
Heterogeneous catalysis be subject to people common concern.
The relevant catalyst report for the synthesis of monobenzyl toluene is concentrated mainly on ionic liquid, heteropoly acid, admittedly both at home and abroad
The heterogeneous catalysis of body super acids, molecular sieve, alkaline earth oxide and the loaded modified type of metal halide, such as
CN102558230A and EP0306961A1 have been reported using quaternary phosphine salt acidic ion liquid and SiO respectively2/Al2O3Molecular sieve
Carry out catalyzing and synthesizing for benzyl toluene.But heteropoly acid and metal halide supported catalyst cannot all overcome equipment corrosion to ask
Topic, and solid super-strong acid, molecular sieve and ionic liquid etc. to there is preparation cost high, the problems such as complex process.Therefore, industry
On urgently develop the new new technology for synthesizing benzyl toluene, reduce catalyst cost, reduce environmental pollution and equipment corrosion,
Improve product yield and selectivity.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation process is simple, raw materials for production low cost, equipment corrosion
Property small, easy recovery, the repeatable efficient heterogeneous solid acid catalyst for the utilizing method that synthesizes benzyl toluene.
Technical solution of the invention is：
A kind of method that active clay loaded ferric trichloride solid acid catalyst catalyzes and synthesizes benzyl toluene, its specific steps
It is：
A kind of method that active clay loaded ferric trichloride solid acid catalyst catalyzes and synthesizes benzyl toluene, it is characterized in that：
Comprise the following steps that：
The preparation of A, active clay loaded solid acid catalyst
To water 270g, concentrated sulfuric acid 30g is added in 1000mL four-hole bottles, calcium base swelling 30g is subsequently adding, is refluxed 6h, be down to
The static 12h of room temperature, filtering, 120 DEG C of drying 8h obtain solid active carclazyte；
B, active clay loaded FeCl3The preparation of solid acid catalyst
By FeCl3It is dissolved in acetonitrile solution, the atlapulgite for adding step A to prepare is stirred at room temperature 24 hours, filters, then at 120
DEG C activation 4 hours, obtain active clay loaded FeCl3Solid acid catalyst；
C, alkylated reaction
By active clay loaded FeCl3Solid acid catalyst is carried out in being added to benzyl chloride and the alkylation reaction system of toluene
Catalytic reaction, catalyst amount is the 3%-5% of benzyl chloride quality, and benzyl chloride is 1 with the mol ratio of toluene:3-1:6, reaction temperature
It is 105 DEG C -115 DEG C to spend, and the reaction time is -8 hours 6 hours, and catalyst is recovered by filtration, and obtains benzyl toluene crude product；
It is D, refined
Benzyl toluene crude product is passed through into vacuum distillation, is refined, obtain benzyl toluene.
Further, atlapulgite and FeCl described in step B3Mass ratio be 12:1.
Further, benzyl chloride and the mol ratio of toluene are 1:3.5.
Further, reaction temperature is 105 DEG C in step C, and the reaction time is 8 hours.
The beneficial effects of the invention are as follows：
The catalyst raw material abundance that the present invention is used, with low cost, preparation process is simple is low without high-temperature activation energy consumption,
Easily separated with product；The synthetic reaction of benzyl toluene is carried out using the catalyst, reaction conversion ratio is high, selectivity is strong, condition temperature
It is small with, equipment corrosion, catalyst easily reclaim and it is repeatable utilize, environmental pollution is small, preferably solves current benzyl toluene synthesis
The problems that used catalyst is present, have broad application prospects.
Embody as follows：
First, catalyst preparation process is simple, without special installation.The solid acid for synthesizing benzyl toluene of previous literature report
Catalyst preparation process is complicated, generally requires the steps such as dipping, kneading, shaping, high-temperature activation, and need kneader, forming machine,
The special catalyst preparation equipment such as Muffle furnace.The catalyst that the present invention is used is due to without processing and forming, and activation temperature is low,
Can meet preparation using Conventional batch reactor and drying plant to require.
2nd, Catalyst Production low cost, energy consumption is small.The solid acid catalyst of document report is using molecular sieve, zirconium oxide etc.
It is that carrier, catalyst raw material high cost, and activation of catalyst generally require 300 DEG C~600 DEG C high temperature, energy consumption is big.The present invention is adopted
It is low (120 DEG C) carrier, catalyst preparation low cost, and activation temperature with atlapulgite with low cost, greatly reduces and urge
Agent prepares energy resource consumption.This technique is raw compared with the quaternary phosphine salt acidic ion liquid ionic-liquid catalyst of document report
Produce cost lower.
3rd, catalytic reaction yield and selectivity are high.The atlapulgite that the present invention uses specific surface area larger is carrier, is increased
Chain carrier, high catalytic efficiency, simultaneously because catalyst surface has moderate acidity, reduces how Benzylation by-product
The generation of thing, the selectivity of target product is high.Single double benzyl toluene total recoverys are up to more than 95%.
4th, catalyst is easily separated, recyclable to use again, and technique tends to greenization.This technique avoids traditional FeCl3、AlCl3
Reclaim difficult Deng homogeneous catalyst, the shortcomings of pollution and equipment corrosion are big, catalyst can be urged by simple filtration or sedimentation separation
Agent repeated multiple times can be used, with good environmental benefit.
Specific embodiment
The preparation of A, active clay loaded solid acid catalyst
To water 270g, concentrated sulfuric acid 30g is added in 1000mL four-hole bottles, calcium base swelling 30g is subsequently adding, is refluxed 6h, be down to
The static 12h of room temperature, filtering, 120 DEG C of drying 8h；Solid active carclazyte is obtained, it is standby as catalyst carrier；
B, active clay loaded FeCl3The preparation of solid acid catalyst
By FeCl3It is dissolved in acetonitrile solution, adds the atlapulgite of step A preparations, the atlapulgite and FeCl3Mass ratio
It is 12:1, it is stirred at room temperature 24 hours, filter, activated 4 hours then at 120 DEG C, obtain active clay loaded FeCl3Solid acid is urged
Agent；
The alkylation synthetic reaction of C, benzyl toluene
By active clay loaded FeCl3Solid acid catalyst is carried out in being added to benzyl chloride and the alkylation reaction system of toluene
Catalytic reaction, catalyst amount is the 3%-5% of benzyl chloride quality, and benzyl chloride is 1 with the mol ratio of toluene:3-1:6, reaction temperature
It is 105 DEG C -115 DEG C to spend, and the reaction time is -8 hours 6 hours, and catalyst is recovered by filtration, and obtains benzyl toluene crude product；
It is D, refined
Benzyl toluene crude product is passed through into vacuum distillation, is refined, obtain benzyl toluene.
In following examples, the conversion ratio of benzyl chloride reacts the content for starting the benzyl chloride with the end of by chromatographic
Calculate：Benzyl chloride content before benzyl chloride conversion ratio (%)=(benzyl chloride content-reaction afterchlorinate benzyl content before reaction) ÷ reactions
× 100%；
Embodiment 1
The preparation of A, active clay loaded solid acid catalyst
To water 270g, concentrated sulfuric acid 30g is added in 1000mL four-hole bottles, calcium base swelling 30g is subsequently adding, is refluxed 6h, be down to
The static 12h of room temperature, filtering, 120 DEG C of drying 8h obtain solid active carclazyte；
B, active clay loaded FeCl3The preparation of solid acid catalyst
Weigh anhydrous FeCl31.0g, is dissolved in 30mL acetonitriles, is stirred well to FeCl3Quan Rong, to 12.0g prepared by step A
Atlapulgite is stirred at room temperature 12h as catalyst carrier, and filtering, solid n-hexane 10mL × 3 time are washed, 120 DEG C of drying 4h,
Obtain active clay loaded FeCl3Solid acid catalyst (F/C catalyst)；
The alkylation synthetic reaction of C, benzyl toluene
Take in F/C catalyst 4g addition 500mL four-hole bottles, then add toluene 280g, be warming up to 110 DEG C, benzyl chloride 80g is added dropwise and enters
Row reaction, 6h is dripped off, then reacts 1h, and cooling stops reaction, and catalyst is recovered by filtration, and liquid 150mL × 3 are washed, 150mL
5% sodium hydrate aqueous solution is washed, and toluene is reclaimed in vacuum distillation；Residue rectification under vacuum respectively obtain monobenzyl toluene (MBT) and
Double benzyl toluene (DBT) cuts.Benzyl chloride conversion ratio, monobenzyl toluene yield, double benzyl toluene yields and single double benzyl toluenes
Total recovery is as shown in table 1.
Embodiment 2
The preparation of A, active clay loaded solid acid catalyst
To water 270g, concentrated sulfuric acid 30g is added in 1000mL four-hole bottles, calcium base swelling 30g is subsequently adding, is refluxed 6h, be down to
The static 12h of room temperature, filtering, 120 DEG C of drying 8h obtain solid active carclazyte；
B, active clay loaded FeCl3The preparation of solid acid catalyst
Weigh anhydrous FeCl31.0g, is dissolved in 30mL acetonitriles, is stirred well to FeCl3Quan Rong, to 12.0g prepared by step A
Atlapulgite is stirred at room temperature 12h as catalyst carrier, and filtering, solid n-hexane 10mL × 3 time are washed, 120 DEG C of drying 4h,
Obtain active clay loaded FeCl3Solid acid catalyst (F/C catalyst)；
Then plus toluene 240g C, take during F/C catalyst 3.2g adds 500mL four-hole bottles, be warming up to 105 DEG C, benzyl chloride is added dropwise
80g is reacted, and 6h is dripped off, then reacts 2h, and cooling stops reaction, and catalyst is recovered by filtration, and liquid 150mL × 3 are washed,
The sodium hydrate aqueous solutions of 150mL 5% are washed, and toluene is reclaimed in vacuum distillation；Residue rectification under vacuum respectively obtains monobenzyl toluene
And double benzyl toluene (DBT) cut (MBT)；Benzyl chloride conversion ratio, monobenzyl toluene yield, double benzyl toluene yields and single double benzyls
Base toluene total recovery is as shown in table 1.
Embodiment 3
The preparation of A, active clay loaded solid acid catalyst
To water 270g, concentrated sulfuric acid 30g is added in 1000mL four-hole bottles, calcium base swelling 30g is subsequently adding, is refluxed 6h, be down to
The static 12h of room temperature, filtering, 120 DEG C of drying 8h obtain solid active carclazyte；
B, active clay loaded FeCl3The preparation of solid acid catalyst
Weigh anhydrous FeCl31.0g, is dissolved in 30mL acetonitriles, is stirred well to FeCl3Quan Rong, to 12.0g prepared by step A
Atlapulgite is stirred at room temperature 12h as catalyst carrier, and filtering, solid n-hexane 10mL × 3 time are washed, 120 DEG C of drying 4h,
Obtain active clay loaded FeCl3Solid acid catalyst (F/C catalyst)；
The alkylation synthetic reaction of C, benzyl toluene
Take in F/C catalyst 2.4g addition 500mL four-hole bottles, then add toluene 480g, be warming up to 115 DEG C, benzyl chloride 80g is added dropwise
Reacted, 6h is dripped off, then reacted 1h, cooling is stopped reaction, catalyst is recovered by filtration, liquid 150mL × 3 are washed, 150mL
5% sodium hydrate aqueous solution is washed, and toluene is reclaimed in vacuum distillation；Residue rectification under vacuum respectively obtain monobenzyl toluene (MBT) and
Double benzyl toluene (DBT) cuts.Benzyl chloride conversion ratio, monobenzyl toluene yield, double benzyl toluene yields and single double benzyl toluenes
Total recovery is as shown in table 1.
Embodiment 4
Method according to embodiment 1 synthesizes benzyl toluene, the difference is that the inventory of toluene is 348g, benzyl chloride conversion ratio, list
Benzyl toluene yield, double benzyl toluene yields and single double benzyl toluene total recoverys are as shown in table 1.
Embodiment 5
Method according to embodiment 1 synthesizes benzyl toluene, the difference is that the inventory of toluene is 242g, benzyl chloride conversion ratio, list
Benzyl toluene yield, double benzyl toluene yields and single double benzyl toluene total recoverys are as shown in table 1.
Embodiment 6
Method according to embodiment 1 synthesizes benzyl toluene, benzyl chloride 7h is added dropwise and drips off, then reacts 1h, benzyl chloride conversion ratio, list
Benzyl toluene yield, double benzyl toluene yields and single double benzyl toluene total recoverys are as shown in table 1.
Embodiment 7
Method according to embodiment 1 synthesizes benzyl toluene, benzyl chloride 5h is added dropwise and drips off, then reacts 1h, benzyl chloride conversion ratio, list
Benzyl toluene yield, double benzyl toluene yields and single double benzyl toluene total recoverys are as shown in table 1.
Comparative example
A, active clay loaded FeCl3The preparation of solid acid catalyst
Weigh anhydrous FeCl31.0g, is dissolved in 30mL acetonitriles, is stirred well to FeCl3Quan Rong, to 12.0g atlapulgites (city
Sell) as catalyst carrier, 12h is stirred at room temperature, to filter, solid n-hexane 10mL × 3 time are washed, 120 DEG C of drying 4h, are lived
Property carclazyte load FeCl3Solid acid catalyst (F/C catalyst)；
The alkylation synthetic reaction of B, benzyl toluene
Take in F/C catalyst 4g addition 500mL four-hole bottles, then add toluene 280g, be warming up to 110 DEG C, benzyl chloride 80g is added dropwise and enters
Row reaction, 3h is dripped off, then reacts 1h, and cooling stops reaction, and catalyst is recovered by filtration, and liquid 150mL × 3 are washed, 150mL
5% sodium hydrate aqueous solution is washed, and toluene is reclaimed in vacuum distillation；Residue rectification under vacuum respectively obtain monobenzyl toluene (MBT) and
Double benzyl toluene (DBT) cuts.Benzyl chloride conversion ratio, monobenzyl toluene yield, double benzyl toluene yields and single double benzyl toluenes
Total recovery is as shown in table 1.
Table 1
Catalyst separate after it is reusable, using 5 times after, due to catalyst member loss product yield be declined slightly,
First using effect is can reach after supplement raw catelyst.
Can relatively be drawn by embodiment and comparative example, directly buy commercially available atlapulgite as catalyst carrier, it makes
With effect not as self-control atlapulgite, catalyst of the self-control carclazyte as carrier is far below on conversion ratio and yield.
Specific embodiment of the invention is these are only, is not intended to limit the invention, for those skilled in the art
For member, the present invention can have various modifications and variations.All any modifications within the spirit and principles in the present invention, made,
Equivalent, improvement etc., should be included within the scope of the present invention.
Claims (4)
1. a kind of method that active clay loaded ferric trichloride solid acid catalyst catalyzes and synthesizes benzyl toluene, it is characterized in that：
Comprise the following steps that：
The preparation of A, active clay loaded solid acid catalyst
To water 270g, concentrated sulfuric acid 30g is added in 1000mL four-hole bottles, calcium base swelling 30g is subsequently adding, is refluxed 6h, be down to
The static 12h of room temperature, filtering, 120 DEG C of drying 8h obtain solid active carclazyte；
B, active clay loaded FeCl3The preparation of solid acid catalyst
By FeCl3It is dissolved in acetonitrile solution, the atlapulgite for adding step A to prepare is stirred at room temperature 24 hours, filters, then at 120
DEG C activation 4 hours, obtain active clay loaded FeCl3Solid acid catalyst；
C, alkylated reaction
By active clay loaded FeCl3Solid acid catalyst is carried out in being added to benzyl chloride and the alkylation reaction system of toluene
Catalytic reaction, catalyst amount is the 3%-5% of benzyl chloride quality, and benzyl chloride is 1 with the mol ratio of toluene:3-1:6, reaction temperature
It is 105 DEG C -115 DEG C to spend, and the reaction time is -8 hours 6 hours, and catalyst is recovered by filtration, and obtains benzyl toluene crude product；
It is D, refined
Benzyl toluene crude product is passed through into vacuum distillation, is refined, obtain benzyl toluene.
2. active clay loaded ferric trichloride solid acid catalyst according to claim 1 catalyzes and synthesizes benzyl toluene
Method, it is characterized in that：Atlapulgite and FeCl described in step B3Mass ratio be 12:1.
3. active clay loaded ferric trichloride solid acid catalyst according to claim 1 catalyzes and synthesizes benzyl toluene
Method, it is characterized in that：Benzyl chloride is 1 with the mol ratio of toluene:3.5.
4. active clay loaded ferric trichloride solid acid catalyst according to claim 1 catalyzes and synthesizes benzyl toluene
Method, it is characterized in that：Reaction temperature is 105 DEG C in step C, and the reaction time is 8 hours.
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Cited By (2)
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| CN113979829A (en) * | 2021-11-05 | 2022-01-28 | 渤海大学 | Preparation method of benzyltoluene/dibenzyltoluene |
| CN114570396A (en) * | 2020-12-01 | 2022-06-03 | 中国石油天然气股份有限公司 | Catalyst for synthesizing 5-hydroxymethylfurfural and preparation method of 5-hydroxymethylfurfural |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114570396A (en) * | 2020-12-01 | 2022-06-03 | 中国石油天然气股份有限公司 | Catalyst for synthesizing 5-hydroxymethylfurfural and preparation method of 5-hydroxymethylfurfural |
| CN113979829A (en) * | 2021-11-05 | 2022-01-28 | 渤海大学 | Preparation method of benzyltoluene/dibenzyltoluene |
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