CN109809970A - A kind of method of catalysis of phenol and methanol production methyl phenyl ethers anisole - Google Patents
A kind of method of catalysis of phenol and methanol production methyl phenyl ethers anisole Download PDFInfo
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- CN109809970A CN109809970A CN201910104647.1A CN201910104647A CN109809970A CN 109809970 A CN109809970 A CN 109809970A CN 201910104647 A CN201910104647 A CN 201910104647A CN 109809970 A CN109809970 A CN 109809970A
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- methyl phenyl
- phenyl ethers
- ethers anisole
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Abstract
The invention discloses a kind of methods of catalysis of phenol and methanol production methyl phenyl ethers anisole, this method uses fixed bed reactors, using auxiliary agents such as modified components and potassium fluoride, cesium fluoride, sodium fluoride such as the carrier loaded cerous nitrate such as trbasic zinc phosphate, ferric phosphate, cupric phosphate, chromium phosphate, zirconium nitrate, lanthanum nitrate, cobalt nitrate, nickel nitrates as catalyst, realize efficiently synthesizing for methyl phenyl ethers anisole, not only phenol conversion is high, methyl phenyl ethers anisole selectivity is high, and catalyst preparation process is simple, at low cost, stability is high, long service life, has reached the application requirement of industrial catalyst.
Description
Technical field
The invention belongs to the preparation technical fields of methyl phenyl ethers anisole, and in particular to a kind of to use catalysis of phenol and methanol production benzene first
The method of ether.
Background technique
Methyl phenyl ethers anisole is called anethole, anisole, methoxybenzene, is a kind of important industrial chemicals, since it has spy
Different fragrance can be used as the additive of soap and detergent；It is used as intermediate in synthetic perfume, dyestuff, enteral insecticide；By
It is big in its dielectric constant, boiling point is high can be used as excellent common reagent, initiator, solvent, thermostat filler etc., additionally, due to
It can improve octane number also and can be used as gasoline additive instead of methyl tertiary butyl ether(MTBE), in printing industry and can also paint face
Make the additive of solvent and synthetic resin and fuel in material industry.In recent years, demand sharp increase of the market to methyl phenyl ethers anisole.
The synthetic method of methyl phenyl ethers anisole according to methylating reagent difference mainly have dimethyl sulfate method, dimethyl carbonate method and
Methanol method.Dimethyl sulfate method has the advantages that reaction temperature is low, target product selectivity is good, at low cost, but used sulphur
Dimethyl phthalate is toxic articles, while needing to convert sodium phenate for phenol in process of production, is needed using a large amount of hydroxide
Sodium generates a large amount of brine waste, and post-processing is difficult, and leading to the method, environmental pollution is serious, this technique is superseded；And carbonic acid two
Methyl esters method and methanol method use green methylating reagent dimethyl carbonate and methanol, do not generate solid waste in production process,
It is two kinds of green synthetic routes.But carbon dioxide and methanol are generated in dimethyl carbonate method reaction process, is needed to titanium dioxide
Carbon is recycled with methanol so that production technology is complex, equipment investment cost is higher, directly result in methyl phenyl ethers anisole cost compared with
Height, the market competitiveness are weaker；And methanol method has the advantages that cost of material is low, does not generate secondary pollution, post-processing is simple, is close
Each main research direction of researcher over year.
Batch process and continuity method can be used in the technique of methanol method synthesis methyl phenyl ethers anisole, and there is productive labor intensity for batch process
Greatly, the defects of equipment energy consumption is high is on the verge of being replaced, and continuity method is with labor intensity is low, low energy consumption, simple operation and other advantages are mesh
Preceding prevailing technology.The catalyst of continuity method production methyl phenyl ethers anisole mainly has oxide, molecular sieve, phosphate etc. the, (Adv such as Oku
Synth Catal, 2005,347 (11-13): 1553-1557) using Cs-P-Si ternary oxide as catalyst, 320 DEG C,
Under 8.2MPa, phenol conversion 49%, methyl phenyl ethers anisole is selectively up to 98%.Kirichenko etc. (Petroleum Chemistry,
2008,48 (5): 389-392) using the NaX molecular sieve of commercialization as catalyst, benzene is realized by the alkylation of phenol methanol vapor phase
Methyl ether synthesis, 320 DEG C, phenolic alcohol ratio be 1:8, phenol conversion 99.8% under normal pressure, methyl phenyl ethers anisole selectivity are up to 90.2%.Zhang
It is prepared for series of rare earth phosphate mesoporous material Deng (Z Phys Chem, 2010,224 (6): 857-864), phenol highest turns
Rate 62.8%, methyl phenyl ethers anisole selectivity 96.8%, by-product only has o-cresol.
Although obtaining a part of breakthrough in the studies above, catalyst all shows higher initial activity, with anti-
The carry out catalyst activity answered gradually is decayed, and catalyst service life is lower, and there is only in alcohol phenol ratio for partial catalyst
The problems such as preferable methyl phenyl ethers anisole selectivity and higher phenol conversion could be obtained under the conditions of higher, is bound to cause energy consumption urgency
Increase severely big, production cost increases, it is difficult to have the market competitiveness；Partial catalyst preparation process is complicated simultaneously, and condition is harsh, leads
It causes catalyst cost larger, also limits it and realize industrial applications.
Summary of the invention
It is an object of the invention in view of the deficiencies in the prior art or insufficient, provide a kind of preparation process it is simple,
The industrialized process for preparing of pollution-free, high conversion rate, catalyst phenol with long service life and methanol production methyl phenyl ethers anisole.
For above-mentioned purpose, the technical solution that the present invention takes is made of following step:
1, carrier is added in deionized water, and modified component is added, 4~8h of stirring at normal temperature, 80~100 DEG C of agings dryings
10~12h, 450~600 DEG C of 3~6h of roasting, is down to room temperature, catalyst intermediate is made；Wherein the carrier and modified component,
The mass ratio of deionized water is 1:(0.01~0.05): (2~5), the carrier are trbasic zinc phosphate, ferric phosphate, cupric phosphate, chromium phosphate
In any one, modified component is cerous nitrate, zirconium nitrate, lanthanum nitrate, cobalt nitrate, any one in nickel nitrate.
2, catalyst intermediate is added in deionized water, and auxiliary agent is added, 3~5h of stirring at normal temperature, 90~110 DEG C of agings
Catalyst is made in dry 10~12h, 450~600 DEG C of 4~8h of roasting；The wherein catalyst intermediate and auxiliary agent, deionization
The mass ratio of water is 1:(0.001~0.01): (2~5), the auxiliary agent are potassium fluoride, cesium fluoride, any one in sodium fluoride.
3, gained catalyst is granulated to, is shaped to the cylindrical particle of 3~6mm of diameter, high 3~6mm, is packed into fixation
Bed reactor；Fixed bed reactors will be continued through after phenol and methanol preheating, in 280~350 DEG C of reaction temperature, reaction pressure
It is to carry out gas phase reaction under 20~40s reaction condition and generate methyl phenyl ethers anisole for 0.1~3MPa, residence time of material.
In above-mentioned steps 1, preferably carrier is added in deionized water, and modified component is added, stirring at normal temperature 6h, 90 DEG C old
Change dry 12h, 500~550 DEG C of 4~5h of roasting are down to room temperature, catalyst intermediate is made.Wherein preferably the carrier with change
Property component, deionized water mass ratio be 1:(0.02~0.04): (3~4) appoint in the preferred cupric phosphate of the carrier, chromium phosphate
It anticipates one kind, the preferred cerous nitrate of the modified component, zirconium nitrate, any one in nickel nitrate.
In above-mentioned steps 2, preferably catalyst intermediate is added in deionized water, and auxiliary agent is added, stirring at normal temperature 4h,
Catalyst is made in 100 DEG C of agings dry 12h, 480~550 DEG C of 5~7h of roasting.Wherein preferably the catalyst intermediate with help
Agent, deionized water mass ratio be 1:(0.004~0.008): (3~4), it is any in the auxiliary agent preferred fluorinated potassium, cesium fluoride
It is a kind of.
In above-mentioned steps 3, preferably gained catalyst is granulated, be shaped to 4~5mm of diameter, high 4~5mm it is cylindric
Particle is packed into fixed bed reactors；Fixed bed reactors will be continued through after phenol and methanol preheating, in reaction temperature 300
~320 DEG C, reaction pressure be 0.5~1.5MPa, residence time of material is under 25~35s reaction condition, it is raw to carry out gas phase reaction
At methyl phenyl ethers anisole.Wherein the molar ratio of the phenol and methanol is 1:(2~5), preferably the molar ratio of phenol and methanol is 1:(3~4).
Beneficial effects of the present invention are as follows:
The present invention has the characteristics that catalyst preparation process is simple, at low cost, and catalysis is used with high conversion rate, selectivity
Well, the characteristics of long service life, 200h is reacted, the conversion ratio of phenol still can reach 79.5%~88.6%, methyl phenyl ethers anisole selectivity
It still can reach 98.1%~99.3%, continue to extend reaction to 2000h, the activity of catalyst is basically unchanged, and has been reached industry and has been urged
The application requirement of agent.
Specific embodiment
Below with reference to embodiment, the present invention is described in more detail, but protection scope of the present invention is not limited only to these realities
Apply example.
Phenol conversion and methyl phenyl ethers anisole selectively use gas chromatographic detection, GC conditions in following example are as follows:
Detector is FID, and 240 DEG C of vaporizing chamber, detector temperature is 240 DEG C, and column temperature is 60 DEG C of constant temperature 2min, and 10 DEG C rise to 180 DEG C, perseverance
Warm 1min, chromatographic column HP-5.
Embodiment 1
1,100g trbasic zinc phosphate is added in 200g deionized water, and 1g cerous nitrate is added, stirring at normal temperature 6h, 90 DEG C of agings
Dry 12h, is put into Muffle furnace and roasts 6h at 450 DEG C, be down to room temperature, catalyst intermediate is made.
2,100g catalyst intermediate is added in 200g deionized water, and 0.1g sodium fluoride is added, stirring at normal temperature 4h,
The dry 12h of 100 DEG C of agings, roasts 8h at 450 DEG C, catalyst is made.
3, gained catalyst is granulated to, is shaped to the cylindrical particle of diameter 4mm, high 4mm, is packed into fixed bed reaction
Device, loaded catalyst 30mL, tube inner diameter 28mm, material are 316L stainless steel；It will be pressed after phenol and methanol preheating
Molar ratio is that 1:3 continues through fixed bed reactors, in 300 DEG C of reaction temperature, reaction pressure be normal pressure, residence time of material is
Under 30s reaction condition, carries out gas phase reaction and generate methyl phenyl ethers anisole.Reaction 200h's the results are shown in Table 1.
Embodiment 2
1,100g ferric phosphate is added in 300g deionized water, and 2g zirconium nitrate is added, stirring at normal temperature 6h, 90 DEG C of agings
Dry 12h, is put into Muffle furnace and roasts 4h at 500 DEG C, be down to room temperature, catalyst intermediate is made.
2,100g catalyst intermediate is added in 300g deionized water, and 0.4g cesium fluoride is added, stirring at normal temperature 4h,
The dry 12h of 100 DEG C of agings, roasts 5h at 500 DEG C, catalyst is made.
3, the step is identical as the step 3 of embodiment 1, and that reacts 200h the results are shown in Table 1.
Embodiment 3
1,100g cupric phosphate is added in 500g deionized water, and 5g lanthanum nitrate is added, stirring at normal temperature 6h, 90 DEG C of agings
Dry 12h, is put into Muffle furnace and roasts 3h at 600 DEG C, be down to room temperature, catalyst intermediate is made.
2,100g catalyst intermediate is added in 500g deionized water, and 1g potassium fluoride is added, stirring at normal temperature 4h, 100
The dry 12h of DEG C aging, roasts 4h at 600 DEG C, catalyst is made.
3, the step is identical as the step 3 of embodiment 1, and that reacts 200h the results are shown in Table 1.
Embodiment 4
1,100g chromium phosphate is added in 500g deionized water, and 4g zirconium nitrate is added, stirring at normal temperature 6h, 90 DEG C of agings
Dry 12h, is put into Muffle furnace and roasts 4h at 550 DEG C, be down to room temperature, catalyst intermediate is made.
2,100g catalyst intermediate is added in 400g deionized water, and 0.8g potassium fluoride is added, stirring at normal temperature 4h,
The dry 12h of 100 DEG C of agings, roasts 4h at 550 DEG C, catalyst is made.
3, the step is identical as the step 3 of embodiment 1, and that reacts 200h the results are shown in Table 1.
Embodiment 5
1,100g cupric phosphate is added in 400g deionized water, and 4g nickel nitrate is added, stirring at normal temperature 6h, 90 DEG C of agings
Dry 12h, is put into Muffle furnace and roasts 7h at 500 DEG C, be down to room temperature, catalyst intermediate is made.
2,100g catalyst intermediate is added in 400g deionized water, and 0.4g potassium fluoride is added, stirring at normal temperature 4h,
The dry 12h of 100 DEG C of agings, roasts 6h at 480 DEG C, catalyst is made.
3, the step is identical as the step 3 of embodiment 1, and that reacts 200h the results are shown in Table 1.
Embodiment 6
1,100g chromium phosphate is added in 300g deionized water, and 4g cerous nitrate is added, stirring at normal temperature 8h, 90 DEG C of agings
Dry 12h, is put into Muffle furnace and roasts 5h at 550 DEG C, be down to room temperature, catalyst intermediate is made.
2,100g catalyst intermediate is added in 300g deionized water, and 0.6g cesium fluoride is added, stirring at normal temperature 4h,
The dry 12h of 100 DEG C of agings, roasts 5h at 500 DEG C, catalyst is made.
3, the step is identical as the step 3 of embodiment 1, and that reacts 200h the results are shown in Table 1.
1 reaction result of table
| Sample | Phenol conversion | Methyl phenyl ethers anisole selectivity | Ortho-methyl phenol | Other |
| Embodiment 1 | 79.5% | 98.8% | 1.0% | 0.2% |
| Embodiment 2 | 81.3% | 98.6% | 1.1% | 0.3% |
| Embodiment 3 | 83.4% | 99.3% | 0.6% | 0.1% |
| Embodiment 4 | 88.6% | 98.1% | 1.6% | 0.3% |
| Embodiment 5 | 85.7% | 98.4% | 1.4% | 0.2% |
| Embodiment 6 | 86.1% | 99.0% | 0.8% | 0.2% |
Claims (8)
1. a kind of method of catalysis of phenol and methanol production methyl phenyl ethers anisole, it is characterised in that this method is made of following step:
(1) carrier is added in deionized water, and modified component is added, 4~8h of stirring at normal temperature, 80~100 DEG C of agings dry 10
~12h, 450~600 DEG C of 3~6h of roasting, is down to room temperature, catalyst intermediate is made；Wherein the carrier and modified component, go
The mass ratio of ionized water is 1:(0.01~0.05): (2~5), the carrier are trbasic zinc phosphate, in ferric phosphate, cupric phosphate, chromium phosphate
Any one, modified component is cerous nitrate, zirconium nitrate, lanthanum nitrate, cobalt nitrate, any one in nickel nitrate；
(2) catalyst intermediate is added in deionized water, and auxiliary agent is added, 3~5h of stirring at normal temperature, 90~110 DEG C of agings are done
Dry 10~12h, 450~600 DEG C of 4~8h of roasting, is made catalyst；The wherein catalyst intermediate and auxiliary agent, deionized water
Mass ratio be 1:(0.001~0.01): (2~5), the auxiliary agent are potassium fluoride, cesium fluoride, any one in sodium fluoride；
(3) gained catalyst is granulated to, is shaped to the cylindrical particle of 3~6mm of diameter, high 3~6mm, is packed into fixed bed
Reactor；Fixed bed reactors will be continued through after phenol and methanol preheating, is in 280~350 DEG C of reaction temperature, reaction pressure
0.1~3MPa, residence time of material are to carry out gas phase reaction under 20~40s reaction condition and generate methyl phenyl ethers anisole.
2. the method for catalysis of phenol according to claim 1 and methanol production methyl phenyl ethers anisole, it is characterised in that: in step (1),
Carrier is added in deionized water, and modified component is added, stirring at normal temperature 6h, the dry 12h of 90 DEG C of agings, 500~550 DEG C of roastings
4~5h is down to room temperature, and catalyst intermediate is made.
3. the method for catalysis of phenol according to claim 1 or 2 and methanol production methyl phenyl ethers anisole, it is characterised in that: step (1)
In, the mass ratio of the carrier and modified component, deionized water is 1:(0.02~0.04): (3~4), the carrier are phosphoric acid
Any one in copper, chromium phosphate, the modified component are cerous nitrate, zirconium nitrate, any one in nickel nitrate.
4. the method for catalysis of phenol according to claim 1 and methanol production methyl phenyl ethers anisole, it is characterised in that: in step (2),
Catalyst intermediate is added in deionized water, and auxiliary agent is added, stirring at normal temperature 4h, 100 DEG C of agings dry 12h, 480~550
DEG C roasting 5~7h, catalyst is made.
5. the method for catalysis of phenol according to claim 1 or 4 and methanol production methyl phenyl ethers anisole, it is characterised in that: step (2)
In, the mass ratio of the catalyst intermediate and auxiliary agent, deionized water is 1:(0.004~0.008): (3~4), the auxiliary agent
For any one in cesium fluoride, potassium fluoride.
6. the method for catalysis of phenol according to claim 1 and methanol production methyl phenyl ethers anisole, it is characterised in that: in step (3),
Gained catalyst is granulated to, is shaped to the cylindrical particle of 4~5mm of diameter, high 4~5mm, is packed into fixed bed reactors；
Will phenol and methanol preheating after continue through fixed bed reactors, 300~320 DEG C of reaction temperature, reaction pressure be 0.5~
1.5MPa, residence time of material are to carry out gas phase reaction under 25~35s reaction condition and generate methyl phenyl ethers anisole.
7. the method for catalysis of phenol according to claim 1 or 6 and methanol production methyl phenyl ethers anisole, it is characterised in that: step (3)
In, the molar ratio of the phenol and methanol is 1:(2~5).
8. the method for catalysis of phenol according to claim 7 and methanol production methyl phenyl ethers anisole, it is characterised in that: in step (3),
The molar ratio of the phenol and methanol is 1:(3~4).
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Cited By (5)
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| CN111187148A (en) * | 2020-02-24 | 2020-05-22 | 上海大学 | Method for simultaneously preparing o-hydroxy phenetole and 1, 3-benzodioxole-2-one |
| CN111298843A (en) * | 2020-04-03 | 2020-06-19 | 陕西煤业化工技术研究院有限责任公司 | Catalyst for catalyzing reaction of pyrogallol and dimethyl carbonate to synthesize 1,2, 3-trimethoxybenzene, and preparation method and application thereof |
| CN113233963A (en) * | 2021-05-27 | 2021-08-10 | 宝鸡文理学院 | Method for preparing anisole from phenol and methanol |
| CN114736105A (en) * | 2022-04-19 | 2022-07-12 | 邵阳学院 | Method for catalytic synthesis of anisole from calcium-aluminum composite oxide |
| CN115448820A (en) * | 2022-10-13 | 2022-12-09 | 南京工业大学 | Mild method for preparing aryl methyl ether from phenol and methanol |
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| CN114736105A (en) * | 2022-04-19 | 2022-07-12 | 邵阳学院 | Method for catalytic synthesis of anisole from calcium-aluminum composite oxide |
| CN114736105B (en) * | 2022-04-19 | 2024-04-12 | 邵阳学院 | Method for synthesizing anisole by catalyzing calcium-aluminum composite oxide |
| CN115448820A (en) * | 2022-10-13 | 2022-12-09 | 南京工业大学 | Mild method for preparing aryl methyl ether from phenol and methanol |
| CN115448820B (en) * | 2022-10-13 | 2023-12-05 | 南京工业大学 | Mild method for preparing aryl methyl ether from phenol and methanol |
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