CN113509947B - Catalyst for synthesizing p-methylanisole as well as preparation method and application thereof - Google Patents

Catalyst for synthesizing p-methylanisole as well as preparation method and application thereof Download PDF

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CN113509947B
CN113509947B CN202110827430.0A CN202110827430A CN113509947B CN 113509947 B CN113509947 B CN 113509947B CN 202110827430 A CN202110827430 A CN 202110827430A CN 113509947 B CN113509947 B CN 113509947B
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catalyst
antioxidant
reaction
methylanisole
mass
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CN113509947A (en
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薛其才
严良
李蕾蕾
寇永利
戚文博
徐桥桥
聂颖颖
拓婷婷
许明杰
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Shaanxi Coal and Chemical Technology Institute Co Ltd
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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
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • 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
    • B01J27/08—Halides
    • B01J27/10—Chlorides
    • 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
    • B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
    • 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
    • B01J33/00—Protection of catalysts, e.g. by coating
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a catalyst for synthesizing p-methylanisole and a preparation method and application thereof, wherein the catalyst comprises a main catalyst and an antioxidant, and the mass of the antioxidant accounts for 5-30% of the mass of the main catalyst; the main catalyst comprises the following components in percentage by mole: 50% -85% of active components; 15% -50% of an auxiliary agent; the active component is LiCl, naCl, KCl, caCl 2 And MgCl 2 One or more of the following; the auxiliary agent is CaCO 3 、CuCO 3 、MgCO 3 、ZnCO 3 、Al 2 (CO 3 ) 3 And MnCO 3 One or more of them. The catalyst can catalyze the reaction of the paracresol and the dimethyl carbonate to synthesize the para-methylanisole, and the process is green, efficient and pollution-free.

Description

Catalyst for synthesizing p-methylanisole as well as preparation method and application thereof
Technical Field
The invention belongs to the technical field of chemical catalysts, in particular to a catalyst for methylation reaction, and more particularly relates to a catalyst for synthesizing p-methylanisole by taking p-cresol and dimethyl carbonate as raw materials, and a preparation method and application thereof.
Background
The p-methylanisole naturally exists in ylang oil and cananga oil, has violet fragrance and ylang flower fragrance, is an important chemical raw material, and is widely applied to the fields of medicines, spices, organic synthesis intermediates and the like. The product is edible spice allowed to be used in national GB2760-86, and is mainly used for preparing nut type essence such as walnut, hazelnut and the like, and also used for preparing essence such as artificial ylang, kanan Jia, violet, narcissus and the like.
At present, the main industrial production method of the p-methylanisole is that after the p-cresol reacts with alkali to obtain sodium phenolate, the sodium phenolate reacts with dimethyl sulfate to obtain a product. The reaction conditions of the route are mild, but the raw material dimethyl sulfate is a high poison, the potential safety hazard is large, the reaction equipment is severely corroded, a large amount of phenol-containing wastewater, salt-containing wastewater and waste solids are produced in the production process, the pollution is serious, and the treatment cost is high.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a catalyst for synthesizing p-methylanisole, a preparation method and application thereof, and the catalyst can catalyze the reaction of p-cresol and dimethyl carbonate to synthesize the p-methylanisole, and the process is green and efficient and has no pollution.
The invention is realized by the following technical scheme:
the catalyst for synthesizing the p-methylanisole comprises a main catalyst and an antioxidant, wherein the mass of the antioxidant accounts for 5-30% of the mass of the main catalyst; the main catalyst comprises the following components in percentage by mole: 50% -85% of active components; 15% -50% of an auxiliary agent;
the active component is LiCl, naCl, KCl, caCl 2 And MgCl 2 One or more of the following;
the auxiliary agent is CaCO 3 、CuCO 3 、MgCO 3 、ZnCO 3 、Al 2 (CO 3 ) 3 And MnCO 3 One or more of them.
Preferably, the antioxidant is one or more of antioxidant 264, antioxidant 330, antioxidant 1010 and antioxidant 1076.
The preparation method of the catalyst for synthesizing the p-methylanisole comprises the step of uniformly mixing active components, auxiliary agents and antioxidants to obtain the catalyst.
Preferably, the mixing is specifically: stirring at a stirring speed of 30-60r/min for 0.5-2h.
The catalyst is used for catalyzing methyl reaction between p-cresol and dimethyl carbonate to obtain the p-methylanisole.
Preferably, the molar ratio of p-cresol to dimethyl carbonate is 1: (1.0-2).
Preferably, the catalyst is used in an amount of 0.1 to 5.0% by mass of p-cresol.
Preferably, the reaction temperature is 150-350 ℃, the reaction pressure is 2-7MPa, and the reaction time is 2-8h.
Compared with the prior art, the invention has the following beneficial technical effects:
the catalyst is used for synthesizing the p-methylanisole by taking the p-cresol as a raw material and adopting the environment-friendly dimethyl carbonate as a methylating agent, has high catalytic activity, can catalyze the reaction of the p-cresol and the dimethyl carbonate to synthesize the p-methylanisole, has high conversion rate, high yield, quick reaction time and no pollution, and has successfully realized industrial application.
According to the invention, an environment-friendly methylating agent dimethyl carbonate is adopted, a green and environment-friendly synthesis process of the p-methylanisole is developed, and the dimethyl carbonate is a low-pollution and environment-friendly new green chemical raw material which is used as a methylating agent to react with p-cresol to synthesize the p-methylanisole, and no wastewater is generated in the production process; the use of sodium hydroxide is avoided; avoiding equipment corrosion, saving production cost, belonging to an environment-friendly low-carbon production process, and having no harm, no toxicity and no pollution to the environment. Compared with the industrialized dimethyl sulfate process, the method has the advantages of low raw material cost and high production efficiency, almost no wastewater and solid waste are produced, and the method can rapidly replace the existing high-pollution process.
Detailed Description
The invention will now be described in further detail with reference to specific examples, which are intended to illustrate, but not to limit, the invention.
The invention provides a catalyst for synthesizing p-methylanisole by taking p-cresol and dimethyl carbonate as raw materials, which comprises a main catalyst and an antioxidant, wherein the mass of the antioxidant accounts for 5-30% of the mass of the main catalyst; the main catalyst comprises the following components in percentage by mole: 50% -85% of active components; 15-50% of auxiliary agent.
The active component is alkali metal or alkaline earth metal halide LiCl, naCl, KCl, caCl 2 And MgCl 2 One or more of the following;
the auxiliary agent is metal carbonate CaCO 3 、CuCO 3 、MgCO 3 、ZnCO 3 、Al 2 (CO 3 ) 3 And MnCO 3 One or more of them.
The antioxidant is one or more of antioxidant 264, antioxidant 330, antioxidant 1010 and antioxidant 1076.
Correspondingly, the invention further provides a preparation method of the catalyst for synthesizing the p-methylanisole by taking the p-cresol and the dimethyl carbonate as raw materials, which comprises the following steps of:
1) According to the composition proportion of the catalyst, weighing a certain amount of active component alkali metal or alkaline earth metal halide and auxiliary agent metal carbonate, wherein the amount of each component is such that the final active component accounts for 50-85% of the main catalyst in mole percent, the auxiliary agent accounts for 15-50% of the main catalyst in mole percent, and then weighing the antioxidant accounting for 5-30% of the main catalyst in mass.
2) Under the condition of room temperature, the three components are mechanically mixed, the stirring speed is 30-60r/min, and the stirring time is 0.5-2h.
3) And (5) barreling the uniformly mixed catalyst for standby.
The invention also provides the industrial application of the catalyst in synthesizing the p-methylanisole by taking the p-cresol and the dimethyl carbonate as raw materials, the scale of the p-methylanisole production line is 1000 tons/year, and the volume of a single reaction kettle is 2.5m 3 . The molar ratio of the paracresol to the dimethyl carbonate is 1: (1.0-2), adding 0.1-5.0wt.% of paracresol into the catalyst during methylation reaction, stirring at 50-200r/min, reacting at 150-350 ℃, reacting at 2-7MPa, and reacting for 2-8h. And rectifying and purifying the reaction mixed solution to obtain the required p-methylanisole.
After the catalyst of the invention is used, in the industrial application of synthesizing the p-methylanisole by taking the p-cresol and the dimethyl carbonate as raw materials, the yield of the p-methylanisole is more than 95 percent, and the purity is more than 99.5 percent. Under the optimal synthesis condition, the yield of the p-methylanisole is more than 98 percent, and the purity is more than 99.9 percent.
Example 1
67% NaCl and 33% CaCO were added according to the catalyst molar composition 3 The method is used for preparing the main catalyst, then antioxidant 264 accounting for 5% of the mass of the main catalyst is weighed, the corresponding three components are added into a solid mixing device, and the stirring speed is 30r/min and the stirring time is 0.5h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.5, carrying out methylation reaction on the catalyst, wherein the dosage of the catalyst is 0.1wt.% of p-cresol, the stirring rate is 80r/min, the reaction temperature is 160 ℃, the reaction pressure is 3MPa, and the reaction time is 3h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 82%, and the purity is more than 99.9%.
Example 2
According to the molar composition of the catalyst, 80% NaCl and 20% CuCO are mixed 3 Is used for preparing the main catalyst,and weighing antioxidant 330 accounting for 15% of the mass of the main catalyst, adding the corresponding three components into a solid mixing device, and stirring at the room temperature at the stirring speed of 50r/min for 0.5h. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.1, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 3wt.% of p-cresol, the stirring rate is 50r/min, the reaction temperature is 200 ℃, the reaction pressure is 4MPa, and the reaction time is 6h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 88%, and the purity is more than 99.9%.
Example 3
70% NaCl and 30% MgCO according to the molar composition of the catalyst 3 The method is used for preparing the main catalyst, then antioxidant 1010 accounting for 20% of the mass of the main catalyst is weighed, the corresponding three components are added into a solid mixing device, and the stirring speed is 50r/min and the stirring time is 0.5h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:2, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 2wt.% of that of p-cresol, the stirring speed is 150r/min, the reaction temperature is 250 ℃, the reaction pressure is 5MPa, and the reaction time is 2h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 86%, and the purity is more than 99.9%.
Example 4
According to the molar composition of the catalyst, 50 percent of KCl and 50 percent of ZnCO are added 3 The method is used for preparing the main catalyst, then antioxidant 1076 accounting for 25% of the mass of the main catalyst is weighed, the corresponding three components are added into a solid mixing device, and the stirring speed is 50r/min and the stirring time is 0.5h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.4, methylation reaction was carried out on a catalyst in an amount of 0.5wt.% of p-cresol with stirring rate90r/min, the reaction temperature is 150 ℃, the reaction pressure is 6MPa, and the reaction time is 5h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 92%, and the purity is more than 99.9%.
Example 5
According to the molar composition of the catalyst, 50 percent of KCl and 50 percent of Al 2 (CO 3 ) 3 The method is used for preparing the main catalyst, then antioxidant 1010 accounting for 30% of the mass of the main catalyst is weighed, the corresponding three components are added into a solid mixing device, and the stirring speed is 50r/min and the stirring time is 0.5h under the condition of room temperature. And (5) barreling the mixed composite catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.3, carrying out methylation reaction on a composite catalyst, wherein the dosage of the catalyst is 2.5wt.% of that of p-cresol, the stirring rate is 160r/min, the reaction temperature is 230 ℃, the reaction pressure is 5MPa, and the reaction time is 8h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 90%, and the purity is more than 99.9%.
Example 6
According to the molar composition of the catalyst, 50 percent of KCl and 50 percent of MnCO are added 3 The method is used for preparing the main catalyst, then antioxidant 264 accounting for 28% of the mass of the main catalyst is weighed, the corresponding three components are added into a solid mixing device, and the stirring speed is 50r/min and the stirring time is 0.5h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.0, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 1.5wt.% of that of p-cresol, the stirring rate is 160r/min, the reaction temperature is 350 ℃, the reaction pressure is 7MPa, and the reaction time is 6h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 91%, and the purity is more than 99.9%.
Example 7
80% CaCl was added according to the catalyst molar composition 2 With 20% ZnCO 3 Is used for preparing the main catalyst, and then weighing 8 percent of the mass of the main catalystAntioxidant 1010, the three corresponding components were added to a solid mixing device at a stirring speed of 50r/min for 0.5h at room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.6, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 0.8wt.% of that of p-cresol, the stirring rate is 120r/min, the reaction temperature is 230 ℃, the reaction pressure is 2MPa, and the reaction time is 7h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 92%, and the purity is more than 99.9%.
Example 8
85% MgCl according to the molar composition of the catalyst 2 With 15% CuCO 3 The method is used for preparing the main catalyst, then antioxidant 1010 accounting for 5% of the mass of the main catalyst is weighed, the corresponding three components are added into a solid mixing device, and the stirring speed is 50r/min and the stirring time is 0.5h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.2, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 5wt.% of p-cresol, the stirring speed is 200r/min, the reaction temperature is 280 ℃, the reaction pressure is 6MPa, and the reaction time is 8h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 93%, and the purity is more than 99.9%.
Example 9
Weighing 45% NaCl and 20% CaCl according to the molar composition of the catalyst 2 With 35% ZnCO 3 The method is used for preparing the main catalyst, antioxidant 264 accounting for 12% of the mass of the main catalyst is weighed, the corresponding four components are added into a solid mixing device, and the stirring speed is 60r/min and the stirring time is 1.5h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:2, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 4.5wt.% of that of paracresol, and the stirring speed is highThe rate is 180r/min, the reaction temperature is 180 ℃, the reaction pressure is 3MPa, and the reaction time is 8h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 90%, and the purity is more than 99.9%.
Example 10
Weighing 35% of KCl and 25% of CaCl according to the molar composition of the catalyst 2 、25％ZnCO 3 And 15% MgCO 3 The method is used for preparing the main catalyst, then antioxidant 264 accounting for 5% of the mass of the main catalyst is weighed, the corresponding five components are added into a solid mixing device, and the stirring speed is 60r/min and the stirring time is 2.0h under the condition of room temperature. And (5) barreling the mixed catalyst for standby.
At 2.5m 3 In the reaction kettle, the mol ratio of the paracresol to the dimethyl carbonate is 1:1.5, carrying out methylation reaction on a catalyst, wherein the dosage of the catalyst is 5wt.% of p-cresol, the stirring speed is 60r/min, the reaction temperature is 320 ℃, the reaction pressure is 6MPa, and the reaction time is 7h. After the reaction is finished, the mixed solution is rectified and purified, the yield of the p-methylanisole is 95.5%, and the purity is more than 99.9%.
The catalyst has the advantages of simple preparation process, low catalyst cost, easy separation of the solid catalyst from the product, high catalytic activity and high product yield, can be used for catalyzing the reaction of the p-cresol and the dimethyl carbonate to generate the p-methylanisole, has green and efficient process and no pollution, and has successfully realized industrial application. 1000 tons/year of p-methylanisole production line has been put into production, the product yield is more than 95%, the product purity is more than 99.5%, and 30 tons of p-methylanisole are stably and continuously produced at present.
The invention is not limited to the above embodiments, and based on the technical solution disclosed in the invention, a person skilled in the art may make some substitutions and modifications to some technical features thereof without creative effort according to the technical content disclosed, and all the substitutions and modifications are within the protection scope of the invention.

Claims (7)

1. The application of the catalyst in synthesizing the p-methylanisole is characterized in that the catalyst comprises a main catalyst and an antioxidant, wherein the mass of the antioxidant accounts for 5-30% of the mass of the main catalyst; the main catalyst comprises the following components in percentage by mole: 50% -85% of active components; 15% -50% of an auxiliary agent;
the active component is LiCl, naCl, KCl, caCl 2 And MgCl 2 One or more of the following;
the auxiliary agent is CaCO 3 、CuCO 3 、MgCO 3 、ZnCO 3 、Al 2 (CO 3 ) 3 And MnCO 3 One or more of the following;
the catalyst is adopted to catalyze the methylation reaction of the paracresol and the dimethyl carbonate to obtain the paracetamol.
2. Use according to claim 1, characterized in that the molar ratio of p-cresol to dimethyl carbonate is 1: (1.0-2).
3. Use according to claim 1, characterized in that the catalyst is used in an amount of 0.1-5.0% by mass of p-cresol.
4. The use according to claim 1, wherein the reaction temperature is 150-350 ℃, the reaction pressure is 2-7MPa, and the reaction time is 2-8h.
5. The use of claim 1, wherein the antioxidant is one or more of antioxidant 264, antioxidant 330, antioxidant 1010 and antioxidant 1076.
6. The use according to claim 1, wherein the catalyst is prepared by the following method: and uniformly mixing the active components, the auxiliary agent and the antioxidant to obtain the catalyst.
7. The use according to claim 6, wherein said mixing is in particular: stirring at a stirring speed of 30-60r/min for 0.5-2h.
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