CN109651090A - A kind of method that Bi-MWW catalysis paraxylene hydroxylating prepares 2,5- xylenol - Google Patents

A kind of method that Bi-MWW catalysis paraxylene hydroxylating prepares 2,5- xylenol Download PDF

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CN109651090A
CN109651090A CN201910076205.0A CN201910076205A CN109651090A CN 109651090 A CN109651090 A CN 109651090A CN 201910076205 A CN201910076205 A CN 201910076205A CN 109651090 A CN109651090 A CN 109651090A
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paraxylene
mww
catalyst
xylenol
hydroxylating
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CN109651090B (en
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胡晖
高艳玲
黄清明
陈晓晖
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Fuzhou University
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Fuzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B01J29/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J29/7876—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0027—Powdering
    • B01J37/0036—Grinding
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself

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

Abstract

The invention discloses a kind of Bi-MWW catalysis paraxylene hydroxylating preparations 2, the method of 5- xylenol, silicon source, bismuth source, crystal seed, boric acid are successively added first in ball mill, ball milling obtains mixed powder, then above-mentioned dry powder is mixed with water, constant temperature be evaporated after in template steam static crystallization, Bi-MWW molecular sieve is made through pickling processes, then the Bi-MWW of preparation is mixed under certain dicyandiamide solution with paraxylene and hydrogen peroxide, in 30-90 DEG C of reaction 1-9 h, product 2,5- xylenol can be obtained.The present invention introduces Bi in MWW molecular sieve by one step dry gum method of mechanical ball mill, the c h bond that phenyl ring in paraxylene can preferably be activated, greatlys improve the activity of paraxylene hydroxylating catalyst system, obtains the conversion ratio of paraxylene up to 58.5%, 2,5- xylenols are selective up to 95.4%.Reaction condition is mild, and catalyst material performance is stablized.

Description

A kind of method that Bi-MWW catalysis paraxylene hydroxylating prepares 2,5- xylenol
Technical field
The invention belongs to paraxylene hydroxylatings to prepare 2,5- xylenol field, specifically provide a kind of Bi-MWW catalysis The method that paraxylene hydroxylating prepares 2,5- xylenol.
Background technique
2,5- xylenols be China GB2760-1996 provide to allow using flavorant, and it is a kind of important Chemical intermediate can be used for manufacturing drug Gemfibrozil, phenolic resin, dyestuff, the intermediate etc. of preservative.Early stage is about 2,5- The production method of xylenol has paraxylene sulfonated alkali fusion method and nitrification reduction method.But traditional 2,5- xylenol There is reaction process complexity in synthetic method, operating procedure is more, and severe corrosion to equipment, atom utilization is low, or even also tight The disadvantages of heavily contaminated environment, therefore by activating phenyl ring under conditions of suitable catalyst and oxidant, make aromatic hydrocarbons to diformazan One one-step hydroxylation of benzene generates corresponding phenols, is the highest method of atom utilization in aromatic hydrocarbons synthesis phenols, it is potential economical Advantage and ecological efficiency are by sizable concern.
It is more for the research of benzene, phenol, toluene one-step hydroxylation from the point of view of existing documents and materials, but at present about The research report that the direct hydroxyl of paraxylene turns to 2,5- xylenol is few in number.According to documents and materials it is found that peroxide Changing hydrogen is that a kind of atom utilization is high, environmental-friendly hydroxylating agent.It is hydroxylated that researchers are used as paraxylene Oxidant is used for one one-step hydroxylation of paraxylene, and reaction condition is mild, wherein the catalyst that report is applied to the system has Cu to mix Miscellaneous alumina column montmorillonite sample (Bharanowski K, et al. Clay Minerals, 1999,34 (1): 79- 87.), Fe3+/γ-Al2O3(Monfared H H, et al. Journal of Molecular Catalysis A Chemical, 2004,217 (1): 161-164.), PG8(Wang Xiao, wait Journal of Molecular Catalysis, 2011,25 (3): 244-249.), Osmium nitrogen complex (Kwong H K, et al. Angewandte Chemie, 2017.) etc., first three catalyst pair The selectivity of the reaction of dimethylbenzene, obtained 2,5- xylenol is poor, is no more than 56%；PG8 and the catalysis of osmium nitrogen complex Agent preparation process is complicated, and there are problems that catalyst is separated with reaction system difficulty.
In terms of environment and economic angle, more clean synthetic route is developed by Green Chemistry method, is related to efficiently urging The design of agent.Conversion ratio and the two selective technical indicators are how improved simultaneously, are developed suitable catalyst, are to diformazan The process route that benzene hydroxylation prepares 2,5- xylenol realizes industrialized key.
Summary of the invention
Insufficient according to prior art, the present invention provides a kind of preparations of Bi-MWW catalyst paraxylene hydroxylating The method of 2,5- xylenols, Bi-MWW points of specially a kind of catalysis paraxylene hydroxylating preparation 2,5- xylenol The preparation method of son sieve.The paraxylene hydroxyl that a kind of catalytic performance is more preferable, environmentally protective is provided on the basis of existing technology Change the method for preparing 2,5- xylenol.
The technical solution of the present invention is as follows:
Catalyst is Bi-MWW, is prepared by the following method, and (1) takes silicon source and bismuth to mix in ball mill；(2) by crystal seed MWW, boric acid are added in said mixture, obtain mixed powder after continuing ball milling, constant temperature is evaporated after taking dry powder to mix with water, is obtained Dry glue；(3) by dry glue obtained in template steam static crystallization；(4) Bi- is made after pickling, roasting in crystallization product MWW molecular sieve catalyst；
By obtained Bi-MWW molecular sieve and reactant paraxylene, oxidants hydrogen peroxide (30%) in certain dicyandiamide solution Middle mixing, constant temperature is stirred to react 1-9 h under the conditions of 30-90 DEG C, obtains hydroxylation product 2,5- xylenol.
In above-mentioned catalyst preparation step (1), ground and mixed is carried out to silicon source and bismuth source using planetary ball mill.Its In, the silicon source is one or both of white carbon black, silica gel, and bismuth source is one or both of bismuth nitrate, bismuth acetate；It is described Silicon bismuth molar ratio is 1:(0.005-0.05)；The revolving speed of the ball mill is 200-800 rpm, and runing time is 12-120 h;
In above-mentioned catalyst preparation step (2), the crystal seed MWW is one or both of MWW, the MWW of boron removal of boracic；Institute The mass ratio for stating crystal seed and silicon source is 1:(2-100), silicon boron molar ratio is (1-15): 1, the mass ratio of dry powder and water is 1:(1- 8)；Wherein, the runing time in the ball mill is 12-24 h, and constant temperature evaporated temperature is maintained at 60-100 DEG C；
In above-mentioned catalyst preparation step (3), the static crystallization process are as follows: after dry glue made from step (2) is placed in container, It is put into the polytetrafluoroethyllining lining for filling template and aqueous mixtures, the constant temperature static crystallization in autoclave.Wherein, institute Stating template is piperidines or hexamethylene imine；The silicon source: template: the molar ratio of water is 1:(0.5-1): (2-10)； The static crystallization temperature is 130-180 DEG C, and crystallization time is 24-120 h；
In above-mentioned catalyst preparation step (4), acid that the acid cleaning process uses is one or both of nitric acid, sulfuric acid, Concentration is 1-6 M, and pickling time is 6-20 h；The maturing temperature is 450-650 DEG C, and the time is 5-10 h；
It is above-mentioned catalyst paraxylene hydroxylating preparation 2,5- xylenol reaction in, the catalyst amount is The 5%-40% of paraxylene quality；
It is above-mentioned catalyst paraxylene hydroxylating preparation 2,5- xylenol reaction in, the paraxylene and oxygen The molar ratio of agent hydrogen peroxide (30%) is 1:(0.5-6)；
It is above-mentioned catalyst paraxylene hydroxylating preparation 2,5- xylenol reaction in, the paraxylene with it is molten The volume ratio of agent is 1:(1-10)；
It is above-mentioned catalyst paraxylene hydroxylating preparation 2,5- xylenol reaction in, the solvent be selected from second One of nitrile, acetone, the tert-butyl alcohol, acetic acid, water are a variety of.
The invention has the benefit that
1. Bi-MWW molecular sieve prepared by the present invention, preparation method is simple, can be filled silicon source and bismuth source using ball mill grinding method Divide mixing, Bi component is successfully introduced into MWW molecular sieve；
2. by introducing Bi component in MWW molecular sieve, activation using Bi-MWW molecular sieve to phenyl ring c h bond is greatly improved pair The activity of diformazan benzene hydroxylation catalyst system；
Bi-MWW molecular sieve catalyst prepared by the present invention prepares 2,5- xylenol for being catalyzed paraxylene hydroxylating Reaction, mild condition, catalyst material performance is stablized, and catalyst is easily separated with reaction system, meets green, environmental protection want It asks.
Specific embodiment
A specific embodiment of the invention will make technical solution of the present invention by following case study on implementation more detailed Illustrate, and the embodiment should not be construed as the limitation of the scope of the invention.
Embodiment 1:
The preparation of catalyst:
(1) 3 g white carbon blacks, 0.49 g bismuth nitrate are taken, is mixed and is placed in ball grinder, operate planetary ball mill, revolving speed is 800 rpm, runing time are 48 h；(2) 0.3 g boron removal crystal seed MWW, 0.38 g boric acid are weighed respectively, are added above-mentioned steps (1) Mixture in, continue in ball mill and mix, revolving speed be 300 rpm, 12 h of runing time；Obtained mixture is transferred to again In polytetrafluoroethyllining lining, the mixing of 8.5 g deionized waters is added, is evaporated to obtain dry glue in 80 DEG C of stirrings；(3) 2.13 are weighed respectively G piperidines, 2.7 g water are placed in the polytetrafluoroethyllining lining of autoclave, then the small polytetrafluoroethylene (PTFE) that will fill obtained dry glue Liner is put in big liner, in autoclave at 150 DEG C 72 h of static crystallization；(4) the nitric acid acid of crystallization product 3M It washes and handles 12 h, in 550 DEG C of 6 h of roasting after washing and drying, obtained product is Bi-MWW-a catalyst.
Embodiment 2:
Prepare Bi-MWW-b catalyst according to embodiment 1, difference is, taken in catalyst preparation step (1) 3 g white carbon blacks, 0.65 g bismuth nitrate, is mixed and is placed in ball grinder, operates planetary ball mill, and revolving speed is 800 rpm, runing time 48 h。
Embodiment 3:
Bi-MWW-c catalyst is prepared according to embodiment 1, difference is, it is de- to weigh 0.3 g in catalyst preparation step (2) respectively Boron crystal seed MWW, 0.25 g boric acid are added in the mixture of above-mentioned steps (1), continue in ball mill and mix, revolving speed 300 Rpm, 12 h of runing time；Obtained mixture is transferred in polytetrafluoroethyllining lining again, the mixing of 8.5 g deionized waters is added, It is evaporated to obtain dry glue in 80 DEG C of stirrings.
Embodiment 4:
Bi-MWW-d catalyst is prepared according to embodiment 1, difference is that catalyst preparation step weighs 1.89 g in (3) respectively Piperidines, 2.7 g water are placed in the polytetrafluoroethyllining lining of autoclave, then will be in the small polytetrafluoroethylene (PTFE) that fill obtained dry glue Lining be put in big liner, in autoclave at 150 DEG C 72 h of static crystallization.
Embodiment 5:
Bi-MWW-e catalyst is prepared according to embodiment 1, difference is that crystallization product is with 5M's in catalyst preparation step (4) Nitric acid acidwashing handles 8 h, in 550 DEG C of 6 h of roasting after washing and drying.
Embodiment 6-10:
Weigh the Bi-MWW molecular sieve catalyst of 100 mg different conditions preparation, 1.06 g paraxylene (10 mmol), 10 mL Acetonitrile is added in three-necked flask and mixes, adds the H of 2.27 g2O2(30%), 4 h of isothermal reaction at 60 DEG C, sampling carry out gas Analysis of hplc.Analytical conditions for gas chromatography is referring specifically to 108557840 A of patent CN.The catalyst of different condition preparation is urged Changing paraxylene hydroxylation activity the results are shown in Table 1.
Table 1
Embodiment Catalyst Paraxylene conversion/% 2,5- xylenol selectivity/%
6 Bi-MWW-a 43.7 89.5
7 Bi-MWW-b 53.8 95.4
8 Bi-MWW-c 58.5 88.6
9 Bi-MWW-d 54.2 90.2
10 Bi-MWW-e 41.5 87.8
Embodiment 11-15:
Weigh the above-mentioned Bi-MWW-b molecular sieve catalyst of different quality, 1.06 g paraxylene (10 mmol), 10 mL acetonitriles, It is added in three-necked flask and mixes, add the H of 2.27 g2O2(30%), in 60 DEG C of 4 h of isothermal reaction, sampling carries out gas-chromatography Analysis, test condition is the same as embodiment 6.The Bi-MWW-b catalyst paraxylene hydroxylation activity of different amounts the results are shown in Table 2。
Table 2
Embodiment Catalyst amount/mg Paraxylene conversion/% 2,5- xylenol selectivity/%
11 50 38.2 93.5
12 150 56.5 91.3
13 200 61.8 89.2
Embodiment 14-18:
The above-mentioned Bi-MWW-b molecular sieve catalyst of 100 mg, 1.06 g paraxylene (10 mmol) are weighed, 10 mL acetonitriles are added It is mixed in three-necked flask, adds the H of 2.27 g2O2(30%), 4 h of isothermal reaction under different temperatures, sampling carry out gas phase color Spectrum analysis, test condition is the same as embodiment 6.Paraxylene hydroxylation activity result is shown under the conditions of catalyst differential responses temperature Table 3.
Table 3
Embodiment Reaction temperature/DEG C Paraxylene conversion/% 2,5- xylenol selectivity/%
14 30 10.6 94.0
15 40 24.8 93.5
16 50 37.5 94.7
17 70 57.2 88.5
18 80 63.5 80.3
Embodiment 19-23:
The above-mentioned Bi-MWW-b molecular sieve catalyst of 100 mg, 1.06 g paraxylene (10 mmol) are weighed, 10 mL acetonitriles are added It is mixed in three-necked flask, adds the H of different quality2O2(30%), in 60 DEG C of 4 h of isothermal reaction, sampling carries out gas-chromatography point Analysis, test condition is the same as embodiment 6.Paraxylene hydroxylation activity result under the conditions of catalyst difference oxidizer is shown in Table 4.
Table 4
Embodiment H2O2Dosage/g H2O2With paraxylene molar ratio Paraxylene conversion/% 2,5- xylenol selectivity/%
19 0.57 0.5 42.8 94.5
20 1.14 1 47.4 93.7
21 3.41 3 59.5 88.4
22 4.54 4 66.9 85.1
23 5.68 5 71.5 79.0
The reaction result of each embodiment is compared it is found that the paraxylene hydroxylating of Bi-MWW molecular sieve catalytic prepares 2,5- dimethyl In the reaction of phenol, the conversion ratio of paraxylene then may be up to 95.4% up to the selectivity of 58.5%, 2,5- xylenol.It urges In agent preparation process silicon bismuth than, boric acid dosage, template dosage, the use of pickling concentration and time and reacting middle catalyst Amount, temperature, the dosage of hydrogen peroxide of reaction etc. can have an impact to reactivity.
Embodiment described above is only several embodiments of the invention, and description is more specific and detailed, but can not Be interpreted as limitations on the scope of the patent of the present invention, used in chemicals be the pure above chemicals of commercially available chemistry.It should Indicate, to those skilled in the art, based on by present inventive concept on, several improvement can be made, these are all It is to belong to the scope of protection of the present invention.Therefore, the scope of protection of the patent of the present invention is subject to the attached claims.

Claims (9)

1. a kind of method of Bi-MWW catalysis paraxylene hydroxylating preparation 2,5- xylenol, it is characterised in that: catalyst It prepares by the following method, (1) takes silicon source and bismuth to mix in ball mill；(2) crystal seed MWW, boric acid are added to above-mentioned mixed It closes in object, continues ball milling and obtain mixed powder, constant temperature is evaporated after taking dry powder to mix with water, obtains dry glue；(3) by dry glue obtained in Static crystallization in template steam；(4) Bi-MWW molecular sieve catalyst is made after pickling, roasting in crystallization product；
By obtained Bi-MWW molecular sieve and reactant paraxylene, oxidants hydrogen peroxide (30%) in certain dicyandiamide solution Middle mixing, constant temperature is stirred to react 1-9 h under the conditions of 30-90 DEG C, obtains hydroxylation product 2,5- xylenol.
2. the method according to claim 1, wherein in catalyst preparation step (1), using planetary ball mill Ground and mixed is carried out to silicon source and bismuth source, wherein the silicon source is one or both of white carbon black, silica gel, and bismuth source is nitric acid One or both of bismuth, bismuth acetate；The silicon bismuth molar ratio is 1:(0.005-0.05)；The revolving speed of the ball mill is 200- 800 rpm, runing time are 12-120 h.
3. the method according to claim 1, wherein in catalyst preparation step (2), the crystal seed MWW be containing One or both of MWW, MWW of boron removal of boron；The crystal seed and the mass ratio of silicon source are 1:(2-100), silicon boron molar ratio For (1-15): 1, the mass ratio of dry powder and water is 1:(1-8);Wherein, the runing time in the ball mill is 12-24 h, permanent Warm evaporated temperature is maintained at 60-100 DEG C.
4. the method according to claim 1, wherein in catalyst preparation step (3), the static crystallization process Are as follows: after dry glue made from step (2) is placed in container, it is put into the polytetrafluoroethyllining lining for filling template and aqueous mixtures, The constant temperature static crystallization in autoclave, wherein the template is piperidines or hexamethylene imine；The silicon source: template Agent: the molar ratio of water is 1:(0.5-1): (2-10)；The static crystallization temperature is 130-180 DEG C, crystallization time 24- 120 h。
5. the method according to claim 1, wherein the acid cleaning process uses in catalyst preparation step (4) Acid be one or both of nitric acid, sulfuric acid, concentration be 1-6 M, pickling time be 6-20 h；The maturing temperature is 450-650 DEG C, the time is 5-10 h.
6. the method according to claim 1, wherein preparing 2,5- bis- in catalyst paraxylene hydroxylating In the reaction of methylphenol, the catalyst amount is the 5%-40% of paraxylene quality.
7. the method according to claim 1, wherein preparing 2,5- bis- in catalyst paraxylene hydroxylating In the reaction of methylphenol, the molar ratio of the paraxylene and oxidants hydrogen peroxide (30%) is 1:(0.5-6).
8. the method according to claim 1, wherein preparing 2,5- bis- in catalyst paraxylene hydroxylating In the reaction of methylphenol, the volume ratio of the paraxylene and solvent is 1:(1-10).
9. solvent according to claim 8, which is characterized in that be selected from one of acetonitrile, acetone, the tert-butyl alcohol, acetic acid, water Or it is a variety of.
CN201910076205.0A 2019-01-26 2019-01-26 Method for preparing 2, 5-dimethylphenol by catalyzing hydroxylation of p-xylene with Bi-MWW Expired - Fee Related CN109651090B (en)

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Publication number Priority date Publication date Assignee Title
CN111170851A (en) * 2019-09-25 2020-05-19 蚌埠学院 Preparation of acetic acid-2, 5-dimethylphenyl ester and 2, 5-dimethylnitrobenzene by one-pot method
CN112691663A (en) * 2019-10-23 2021-04-23 中国石油化工股份有限公司 Catalyst and preparation method thereof and application of catalyst in synthesis of 2, 5-xylenol
CN112691663B (en) * 2019-10-23 2022-12-27 中国石油化工股份有限公司 Catalyst and preparation method thereof and application of catalyst in synthesis of 2, 5-xylenol

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