CN105061155A - Method for preparing 3,5-dimethylphenol - Google Patents
Method for preparing 3,5-dimethylphenol Download PDFInfo
- Publication number
- CN105061155A CN105061155A CN201510434001.1A CN201510434001A CN105061155A CN 105061155 A CN105061155 A CN 105061155A CN 201510434001 A CN201510434001 A CN 201510434001A CN 105061155 A CN105061155 A CN 105061155A
- Authority
- CN
- China
- Prior art keywords
- iron
- mixed oxide
- water
- reaction
- isophorone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
- C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/866—Nickel and chromium
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a method for preparing 3,5-dimethylphenol through an isophorone aromatization reaction catalyzed by a mixed oxide catalyst. The invention relates to a method for preparing 3,5-dimethylphenol. The method comprises the following steps: 1, an iron-nickel-chromium mixed oxide catalyst is sieved; 2, isophorone is subjected to an aromatization reaction with formed and roasted iron-nickel-chromium oxide. According to the invention, the iron-nickel-chromium oxide is synthesized with a precipitate hydrothermal method or a traditional sol-gel method. The iron-nickel-chromium oxide is used for catalyzing the isophorone aromatization reaction, such that defects such as non-continuous reaction, difficult separation with product, serious equipment corrosion and environment pollution caused by homogenous catalysts such as iodomethane are overcome. The catalyst has higher reactivity, higher 3,5-dimethylphenol selectivity and higher anti-coking capacity. The reaction product can be easily separated from the catalyst. Operation is simple. The method is suitable for large-scale productions.
Description
Technical field
The present invention relates to a kind of method preparing MX, be specifically related to a kind of method that iron nickel chromium triangle mixed oxide catalyst catalysis isophorone aromizing prepares MX.
Background technology
3,5-xylenol is important Industrial intermediates, mainly for the preparation of the production of antioxidant, microbiotic, resin glue and vitamin-E etc., be also widely used in various antibacterial, mildew-resistant treating processes, as the antibacterial and mouldproof process of leather, paper, textiles and photo etc.The demand of the world today to MX increases day by day, and the annual output in the whole world is fewer, and domestic output is less, is difficult to the demand meeting market.At present, the method for domestic production MX is m-xylene sulfonation alkali solution technique, and this complex technical process is seriously polluted, and product purity is not high.Compared with traditional method, isophorone aromizing single stage method prepares MX, and atom utilization can be made to reach 88.39%, and much larger than Traditional Method preparation technology, and product is single, easily purifies, and is the anxious technique leaved for development of a kind of environmental protection.
As far back as the forties in 20th century, in United States Patent (USP), reported first is with isophorone under temperature is 668-676 DEG C of condition, prepares MX.But owing to not using catalyzer at that time, therefore yield was lower.Afterwards through research, start to adopt homogeneous catalyst, the aliphatic hydrocarbon that the homogeneous catalyst used is replaced by halogen atom or aromatic hydrocarbon, but use this catalyzer to there is catalyzer and reaction product separation difficulty, react the problem such as discontinuous, therefore, present stage research heterogeneous catalyst becomes focus.Up to now, successively someone employs V
20
5/ A1
20
3, Mo0
3/ Al
2o
3, rare-earth oxide (rubidium praseodymium mixed oxide) and Cr
20
3/ A1
20
3prepare 3 Deng multiple catalysts for isophorone, in the reaction of 5 one xylenols, but it is fast all to there is inactivation, the problems such as selectivity is low.At present, iron-nickel-chromium can solve Catalysts Deactivation Problems, but its working time only can maintain 135h, and selectivity of product is lower, and Catalyst Production cost is higher.At present, do not have a kind of heterogeneous catalyst can the report of continued running of realization response under the condition ensureing selectivity of product, multi-component oxide prepared by precipitation hydro-thermal or sol-gel method is applied to this reaction by first, the continued running of selectivity of product realization response under higher condition can be realized, the scale operation of product can be realized.
Summary of the invention
The object of the invention is to provide a kind of method that iron nickel chromium triangle mixed oxide catalysis isophorone aromizing prepares MX, realizes according to the following steps:
Prepare a method for MX, concrete steps are as follows:
1) catalyzer loads the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe;
2) adopt volume pump isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with catalyzer, temperature of reaction is 450-600 DEG C, and pressure is 1.5-5MPa, and mass space velocity is 0.5-2h
-1, nitrogen flow rate is 20-60ml/min, and reaction times 5h, namely obtains MX;
Described catalyzer is 20-40 object iron nickel chromium triangle mixed oxide.
Preferably, step 2) described in temperature of reaction be 570 DEG C, pressure is 2.5MPa, and mass space velocity is 1h
-1, nitrogen flow rate is 40ml/min.
The preparation method of described iron nickel chromium triangle mixed oxide, concrete steps are as follows:
1) six water nickelous nitrate 1 part, nine water chromium nitrate 2 ~ 4 parts, nine water iron nitrate 8 ~ 16 parts, deionized water 10 ~ 18 parts is taken by weight;
2) a: by step 1) the six water nickelous nitrates, nine water chromium nitrates, the nine water iron nitrates that take join in deionized water, and room temperature low whipping speed is stir 10 ~ 50min under the condition of 300 ~ 500r/min, makes it dissolve, makes solution A; B: low whipping speed is under the condition of 300 ~ 700r/min, joins in solution A prepared by step a by tensio-active agent, after adding, then low whipping speed is stir 1 hour under the condition of 100 ~ 300r/min, makes mixing solutions B;
3) to step 2) add precipitation agent in the B solution of gained, control temperature 20 ~ 80 DEG C, adjust ph is 8-11, be placed in the stainless closed reactor with polytetrafluoroethyllining lining pad, crystallization 3 ~ 24h under the temperature condition of 100 ~ 185 DEG C, be cooled to 25 DEG C, through centrifugal, filtration, obtain mixed oxide with after deionized water wash, drying;
4) to step 3) add tackiness agent, compressing tablet, the i.e. obtained product of 550 DEG C of roastings in the mixed oxide that obtains;
Described step 2) in added tensio-active agent be selected from one in cetyl trimethylammonium bromide, polyethylene glycol 6000, Sodium dodecylbenzene sulfonate, polyvinylpyrrolidone, and consumption is 1% ~ 5% of solid mixture gross weight;
Described step 3) in precipitation agent be selected from one in urea, ammoniacal liquor; The massfraction of described ammoniacal liquor is 25%.
Described step 4) in tackiness agent be selected from one in polyacrylamide, aluminum oxide, and consumption is 1% ~ 5% of solid mixture gross weight.
Prepare 3 by isophorone, the process of 5 one xylenols is divided into two parts: a part is for being adsorbed on the isophorone demethanizing process on catalyst surface; Another part is that the isophorone sloughing methane carries out the rearrangement of dienone one phenol, forms 3,5 one xylenols, and by the absorption of catalyst surface metal pair carbonylic oxygen atom, towering key in C=O bond is relaxed, and towering electronics shifts to metal direction.Make the towering key generation covalent linkage heterolytic fission in C=O bond like this, form carbonium ion.Meanwhile, in isophorone molecule, because methylene carbon is directly connected with carbonylic carbon atom, the δ key of C=O bond and α-C-H produces to surpass grips effect altogether, and the result of electron delocalization impact makes the δ key of C-H polarize, and hydrogen atom shows certain acidity.In addition, the carbon atom of methylene radical is Sp3 hydridization, it is directly connected with the carbonylic carbon atom of Sp2 hydridization, because sp2 hydbridized carbon atoms has stronger electronegativity than sp3 hydbridized carbon atoms, the result of inductive effect impact makes hydrogen atom have certain activity, due to super result of gripping effect and inductive effect impact altogether, hydrogen atom is very active, and demonstrate certain acidity, can be adsorbed on the Sauerstoffatom of catalyst surface, methylene carbon then defines carbanion, because resonance effect electronics there occurs transfer, the carbon on five is made to define carbanion, this just makes its carbon-carbon bond be connected with methyl weaken.Under high temperature action, the δ bond rupture between carbanion and methine carbon atom.The methyl taken off be adsorbed on the hydrogen on catalyst surface and be combined, form methane molecule, isophorone also becomes dienone simultaneously, due to resonant interaction, carbonium ion shifts, and forms 3, the resonance hybrid of 5-xylenol, finally forms MX.
Iron and nickel have anti-deactivation, and chromic oxide wherein O
2-for basic center, play dehydrogenation, Cr
3+for acid site, playing aromizing effect, is be applied to dehydroaromatizationof more a kind of active centre at present.This composite oxide catalysts of our synthesis is different from the catalyzer of mechanically mixing, and oxonium ion is close-packed in a certain way, and metallic cation is filled in by O by its ionic radius size
2-on the suitable clearance position of composition, in structure, there is not independently oxygen acid radical ion.This just makes the dispersity of this several metal higher, and at present, the biggest problem of this reaction of catalysis is the carbon distribution problem of catalyzer.Synergy between this several metal is ensureing higher conversion and the carbon distribution problem optionally simultaneously solving catalyzer.Product later separation is simple to operate, and this technique is easy to realize industrialization.
The invention has the advantages that:
1, mixed oxide catalyst of the present invention, adopts precipitation hydro-thermal or sol-gel method preparation, simple.
2, production technique of the present invention adopts single stage method heterogeneous successive reaction synthesis MX, pollutes little, product and catalyzer easily separated.
3, institute's invention catalyst application is in this technique of catalysis, can long-play, decreases the filling frequency of catalyzer, reduces the material consumption and energy consumption of stopping work, easily realize the scale operation of product.
Accompanying drawing explanation
Fig. 1 is different fluorine that ketone transformation efficiency and the graph of relation in reaction times.
Embodiment
Technical solution of the present invention is not limited to following cited embodiment, also comprises the arbitrary combination between each concrete enforcement.
Embodiment 1
One, 20-40 object iron nickel chromium triangle mixed oxide catalyst is loaded the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe.
Two, adopt volume pump raw material isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with iron nickel chromium triangle mixed oxide catalyst, temperature of reaction is 450 DEG C, and pressure is 1.5MPa, and mass space velocity is 0.5h
-1, nitrogen flow rate is 20ml/min, reaction times 5h, namely completes iron nickel chromium triangle mixed oxide catalysis isophorone aromizing and prepares MX;
The nickel chromium triangle of iron described in the present embodiment mixed oxide catalyst adopts co-precipitation water heat transfer, concrete synthetic method is as follows: by nine water iron nitrates, six water nickelous nitrates, nine water chromium nitrates press ferric oxide: chromic oxide: the ratio of weight and number of nickel oxide=8.69:1.15:1 dissolves, add the cetyl trimethylammonium bromide of 5% oxide weight mark, add ammoniacal liquor adjust ph to 10, stir and be placed on crystallization 12h in 180 DEG C of baking ovens, through washing, drying obtains mixed oxide, add the aluminum oxide of 3% weight fraction, compression molding, obtained after 550 DEG C of roasting 3h.
In the present embodiment, the time of outflow first product is counted the t=0 moment, and every each 5h gathers a product, analyzes by gas-chromatography, calculate the transformation efficiency, 3 of isophorone by marker method, the yield of 5-xylenol, the results are shown in Table 1 during reaction times 200h.
Table 1
Embodiment 2
One, 20-40 object iron nickel chromium triangle mixed oxide catalyst is loaded the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe.
Two, adopt volume pump raw material isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with iron nickel chromium triangle mixed oxide catalyst, temperature of reaction is 600 DEG C, and pressure is 5MPa, and mass space velocity is 2h
-1, nitrogen flow rate is 60ml/min, reaction times 5h, namely completes iron nickel chromium triangle mixed oxide catalysis isophorone aromizing and prepares MX;
The nickel chromium triangle of iron described in the present embodiment mixed oxide catalyst adopts co-precipitation water heat transfer, concrete synthetic method is as follows: by nine water iron nitrates, six water nickelous nitrates, nine water chromium nitrates press ferric oxide: chromic oxide: the ratio of weight and number of nickel oxide=10.05:2.59:1 dissolves, add the polyethylene glycol 6000 of 3% oxide weight mark, add the ammoniacal liquor adjust ph to 10 that massfraction is 25%, stir and be placed on brilliant magnificent 12h in 180 DEG C of baking ovens, through washing, drying obtains mixed oxide, add the polyacrylamide of 3% weight fraction, compression molding, obtained after 550 DEG C of roasting 3h.
In the present embodiment, the time of outflow first product is counted the t=0 moment, and every each 5h gathers a product, analyzes by gas-chromatography, calculate the transformation efficiency, 3 of isophorone by marker method, the yield of 5-xylenol, the results are shown in Table 2 during reaction times 5h.
Table 2
Embodiment 3
One, 20-40 object iron nickel chromium triangle mixed oxide catalyst is loaded the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe.
Two, adopt volume pump raw material isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with iron nickel chromium triangle mixed oxide catalyst, temperature of reaction is 570 DEG C, and pressure is 2.5MPa, and mass space velocity is 1h
-1, nitrogen flow rate is 40ml/min, reaction times 5h, namely completes iron nickel chromium triangle mixed oxide catalysis isophorone aromizing and prepares MX;
The nickel chromium triangle of iron described in the present embodiment mixed oxide catalyst adopts co-precipitation water heat transfer, concrete synthetic method is as follows: by nine water iron nitrates, six water nickelous nitrates, nine water chromium nitrates press ferric oxide: chromic oxide: the ratio of weight and number of nickel oxide=9.62:2.74:1 dissolves, add the Sodium dodecylbenzene sulfonate of 2% oxide weight mark, add the ammoniacal liquor adjust ph to 10 that massfraction is 25%, stir and be placed on brilliant magnificent 12h in 180 DEG C of baking ovens, through washing, drying obtains mixed oxide, add the aluminum oxide of 4% weight fraction, compression molding, obtained after 550 DEG C of roasting 3h.
In the present embodiment, the time of outflow first product is counted the t=0 moment, and every each 5h gathers a product, analyzes by gas-chromatography, calculate the transformation efficiency, 3 of isophorone by marker method, the yield of 5-xylenol, the results are shown in Table 3 during reaction times 5h.
Table 3
Embodiment 4
One, 20-40 object iron nickel chromium triangle mixed oxide catalyst is loaded the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe.
Two, adopt volume pump raw material isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with iron nickel chromium triangle mixed oxide catalyst, temperature of reaction is 500 DEG C, and pressure is 3.0MPa, and mass space velocity is 1.5h
-1, nitrogen flow rate is 40ml/min, reaction times 5h, namely completes iron nickel chromium triangle mixed oxide catalysis isophorone aromizing and prepares MX;
The nickel chromium triangle of iron described in the present embodiment mixed oxide catalyst adopts co-precipitation water heat transfer, concrete synthetic method is as follows: iron(ic) chloride, six water nickelous nitrates, nine water chromium nitrates are pressed ferric oxide: nickel oxide: the ratio of weight and number of chromic oxide=15.62:1:2.74 dissolves, add the polyvinylpyrrolidone of 4% oxide weight mark, add ammoniacal liquor adjust ph to 10, stir and be placed on brilliant magnificent 12h in 180 DEG C of baking ovens, mixed oxide is obtained through washing, drying, add the aluminum oxide of 5% weight fraction, compression molding, obtained after 550 DEG C of roasting 3h.
In the present embodiment, the time of outflow first product is counted the t=0 moment, and every each 5h gathers a product, analyzes by gas-chromatography, calculate the transformation efficiency, 3 of isophorone by marker method, the yield of 5-xylenol, the results are shown in Table 4 during reaction times 200h.
Table 4
Embodiment 5
One, 20-40 object iron nickel chromium triangle mixed oxide catalyst is loaded the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe.
Two, adopt volume pump raw material isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with iron nickel chromium triangle mixed oxide catalyst, temperature of reaction is 560 DEG C, and pressure is 2.7MPa, and mass space velocity is 1.5h
-1, nitrogen flow rate is 50ml/min, reaction times 5h, namely completes iron nickel chromium triangle mixed oxide catalysis isophorone aromizing and prepares MX;
The nickel chromium triangle of iron described in the present embodiment mixed oxide catalyst adopts co-precipitation water heat transfer, concrete synthetic method is as follows: by nine water iron nitrates, six water nickelous nitrates, nine water chromium nitrates press ferric oxide: nickel oxide: the ratio of weight and number of chromic oxide=14.60:2.30:1 dissolves, add the cetyl trimethylammonium bromide of 5% oxide weight mark, add urea adjust ph to 10, stir and be placed on crystallization 12h in 180 DEG C of baking ovens, through washing, drying obtains mixed oxide, add the polyacrylamide of 3% weight fraction, compression molding, obtained after 550 DEG C of roasting 3h.
In the present embodiment, the time of outflow first product is counted the t=0 moment, and every each 5h gathers a product, analyzes by gas-chromatography, calculate the transformation efficiency, 3 of isophorone by marker method, the yield of 5-xylenol, the results are shown in Table 5 during reaction times 200h.
Table 5
Embodiment 6
One, 20-40 object iron nickel chromium triangle mixed oxide catalyst is loaded the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe.
Two, adopt volume pump raw material isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with iron nickel chromium triangle mixed oxide catalyst, temperature of reaction is 590 DEG C, and pressure is 4.5MPa, and mass space velocity is 1.7h
-1, nitrogen flow rate is 55ml/min, reaction times 5h, namely completes iron nickel chromium triangle mixed oxide catalysis isophorone aromizing and prepares MX;
The nickel chromium triangle of iron described in the present embodiment mixed oxide catalyst adopts sol-gel method synthesis, concrete synthetic method is as follows: by nine water iron nitrates, six water nickelous nitrates, nine water chromium nitrates press ferric oxide: nickel oxide: the ratio of weight and number of chromic oxide=9.60:2.30:1 dissolves, add the cetyl trimethylammonium bromide of 5% oxide weight mark, add urea adjust ph to 10, be positioned over expansion curing in 180 DEG C of baking ovens, stir and be placed on crystallization 12h in 180 DEG C of baking ovens, through washing, drying obtains mixed oxide, add the polyacrylamide of 3% weight fraction, compression molding, obtained after 550 DEG C of roasting 3h.
In the present embodiment, the time of outflow first product is counted the t=0 moment, and every each 5h gathers a product, analyzes by gas-chromatography, calculate the transformation efficiency, 3 of isophorone by marker method, the yield of 5-xylenol, the results are shown in Table 6 during reaction times 200h.
Table 6
Adopt example one to be catalyzer, carry out long period evaluation, investigate the stability of catalyzer, as seen from the figure, the stability of catalyzer is better, and after running 350h, isophorone transformation efficiency still can maintain about 85%.
Claims (7)
1. prepare a method for MX, it is characterized in that, concrete steps are as follows:
1) catalyzer loads the flat-temperature zone of fixed-bed micro-reactor stainless steel reaction pipe;
2) adopt volume pump isophorone to be injected continuously the beds of fixed-bed micro-reactor, carry out aromatization with catalyzer, temperature of reaction is 450-600 DEG C, and pressure is 1.5-5MPa, and mass space velocity is 0.5-2h
-1, nitrogen flow rate is 20-60ml/min, and reaction times 5h, namely obtains MX;
Described catalyzer is 20-40 object iron nickel chromium triangle mixed oxide.
2. prepare the method for MX as claimed in claim 1, it is characterized in that, step 2) described in temperature of reaction be 570 DEG C, pressure is 2.5MPa, and mass space velocity is 1h
-1, nitrogen flow rate is 40ml/min.
3. prepare the method for MX as claimed in claim 1, it is characterized in that, the preparation method of described iron nickel chromium triangle mixed oxide, concrete steps are as follows:
1) six water nickelous nitrate 1 part, nine water chromium nitrate 2 ~ 4 parts, nine water iron nitrate 8 ~ 16 parts, deionized water 10 ~ 18 parts is taken by weight;
2) a: by step 1) the six water nickelous nitrates, nine water chromium nitrates, the nine water iron nitrates that take join in deionized water, and under room temperature, low whipping speed is stir 10 ~ 50min under the condition of 300 ~ 500r/min, makes it dissolve, makes solution A; B: low whipping speed is under the condition of 300 ~ 700r/min, joins in solution A prepared by step a by tensio-active agent, after adding, then low whipping speed is stir 1 hour under the condition of 100 ~ 300r/min, makes mixing solutions B;
3) to step 2) add precipitation agent in the B solution of gained, control temperature 20 ~ 80 DEG C, adjust ph is 8-11, be placed in the stainless closed reactor with polytetrafluoroethyllining lining pad, crystallization 3 ~ 24h under the temperature condition of 100 ~ 185 DEG C, be cooled to 25 DEG C, through centrifugal, filtration, obtain mixed oxide with after deionized water wash, drying;
4) to step 3) add tackiness agent, compressing tablet in the mixed oxide that obtains, i.e. obtained product after 550 DEG C of roastings.
4. preparation 3 as claimed in claim 3, the method of 5-xylenol, it is characterized in that, described step 2) in added tensio-active agent be selected from one in cetyl trimethylammonium bromide, polyethylene glycol 6000, Sodium dodecylbenzene sulfonate, polyvinylpyrrolidone, and consumption is 1% ~ 5% of solid mixture gross weight.
5. prepare the method for MX as claimed in claim 3, it is characterized in that, described step 3) in precipitation agent be selected from one in urea, ammoniacal liquor.
6. prepare the method for MX as claimed in claim 3, it is characterized in that, described step 4) in tackiness agent be selected from one in polyacrylamide, aluminum oxide, and consumption is 1% ~ 5% of solid mixture gross weight.
7. prepare the method for MX as claimed in claim 5, it is characterized in that, the massfraction of described ammoniacal liquor is 25%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510434001.1A CN105061155B (en) | 2015-07-22 | 2015-07-22 | A kind of method for preparing 3,5 xylenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510434001.1A CN105061155B (en) | 2015-07-22 | 2015-07-22 | A kind of method for preparing 3,5 xylenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105061155A true CN105061155A (en) | 2015-11-18 |
| CN105061155B CN105061155B (en) | 2017-10-13 |
Family
ID=54490730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510434001.1A Active CN105061155B (en) | 2015-07-22 | 2015-07-22 | A kind of method for preparing 3,5 xylenols |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105061155B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641166A (en) * | 1968-07-10 | 1972-02-08 | Ruetgerswerke Ag | Process for preparing 3 5-dimethylphenol from isophorone |
| CN101348421A (en) * | 2008-09-12 | 2009-01-21 | 湖南利洁生物化工有限公司 | Method for preparing 3,5-dimethylphenol |
| CN101671235A (en) * | 2009-10-19 | 2010-03-17 | 杭州华生医药化工有限公司 | Method for preparing 3,5-dimethylphenol by means of isophorone aromatization |
| CN102675051A (en) * | 2012-04-25 | 2012-09-19 | 江苏焕鑫高新材料科技有限公司 | Energy-saving 3, 5-dimethyl phenol production process |
| CN103030532A (en) * | 2012-12-31 | 2013-04-10 | 杭州华生医药化工有限公司 | Method and device for preparing 3,5-dimethylphenol and co-producing 2,3,5-pseudocuminol |
-
2015
- 2015-07-22 CN CN201510434001.1A patent/CN105061155B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641166A (en) * | 1968-07-10 | 1972-02-08 | Ruetgerswerke Ag | Process for preparing 3 5-dimethylphenol from isophorone |
| CN101348421A (en) * | 2008-09-12 | 2009-01-21 | 湖南利洁生物化工有限公司 | Method for preparing 3,5-dimethylphenol |
| CN101671235A (en) * | 2009-10-19 | 2010-03-17 | 杭州华生医药化工有限公司 | Method for preparing 3,5-dimethylphenol by means of isophorone aromatization |
| CN102675051A (en) * | 2012-04-25 | 2012-09-19 | 江苏焕鑫高新材料科技有限公司 | Energy-saving 3, 5-dimethyl phenol production process |
| CN103030532A (en) * | 2012-12-31 | 2013-04-10 | 杭州华生医药化工有限公司 | Method and device for preparing 3,5-dimethylphenol and co-producing 2,3,5-pseudocuminol |
Non-Patent Citations (1)
| Title |
|---|
| 张宪等: "异佛尔酮芳构化合成3,5-二甲基苯酚研究进展", 《化学工业与工程》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105061155B (en) | 2017-10-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103638963B (en) | P-xylene fluid catalyst prepared by performing alkylation of methylbenzene methyl alcohol and preparation method thereof | |
| CN105732350B (en) | A kind of method that anaerobic dehydrogenation prepares anhydrous formaldehyde | |
| CN102744102B (en) | Metal modified SAPO-34 zeolite catalyst, preparation method thereof and use method thereof | |
| CN109608420B (en) | Method for synthesizing functionalized 1,3-butadiene based on biomass chemicals | |
| CN105732349A (en) | Method for preparing anhydrous formaldehyde through methanol dehydrogenation | |
| CN112973773A (en) | Preparation and application of composite catalyst for preparing liquid fuel by carbon dioxide hydrogenation | |
| CN105618130A (en) | Preparation method and application of catalyst for phenol hydroxylation reaction | |
| CN101352690B (en) | Preparation method and use of molecular sieve catalyst for producing phenylethane from alkylation of benzene with dilute ethylene | |
| CN102746102B (en) | Preparation method of 2,6-DiMethylnaphthalene (DMN) by using SAPO-11 molecular sieve | |
| CN105461515A (en) | Method for preparing cyclopentanol from cyclopentene | |
| CN105233878A (en) | Synthesis method for metal-loaded-type MIL-101 bio-oil hydrogenation catalyst | |
| CN101786943A (en) | Catalytic synthesis method for preparing cresol by toluene one-step hydroxylation reaction | |
| CN102786499A (en) | Method for preparing cyclohexene oxide | |
| CN102744085A (en) | Catalytic system containing nanometer Ru catalyst and alkali zinc sulfate salt and method for preparing cyclohexene through catalytic benzene selective hydrogenation | |
| CN103664485A (en) | Method for producing ethylbenzene and styrene through side chain alkylation of toluene and methanol | |
| CN104557422A (en) | Toluene/methanol side chain alkylation method | |
| CN105061155A (en) | Method for preparing 3,5-dimethylphenol | |
| CN106582683A (en) | Low water ratio ethylbenzene dehydrogenation catalyst | |
| CN104761443A (en) | A method of continuously preparing 3,5,5-trimethyl-3-cyclohexene-1-one | |
| Shang et al. | A review of recent progress on direct heterogeneous catalytic CO2 hydrogenation to gasoline-range hydrocarbons | |
| CN101407464B (en) | Method for preparing p-nitrobenzoic acid from waste polystyrene | |
| CN101703944B (en) | Molecular sieve modified catalyst, preparation method and application thereof to preparation of acrylic ester | |
| CN102553611B (en) | Catalyst applied to producing of methane and co-producing low carbon olefin by converting syngas and preparation and application thereof | |
| CN103466707A (en) | Production method of chromic chloride hexahydrate | |
| CN102786500B (en) | Preparation method of cyclohexene oxide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A method for preparing 3,5-dimethylphenol Effective date of registration: 20211123 Granted publication date: 20171013 Pledgee: SHANDONG CHAMBROAD PETROCHEMICALS Co.,Ltd. Pledgor: CHAMBROAD CHEMICAL INDUSTRY RESEARCH INSTITUTE Co.,Ltd. Registration number: Y2021980013118 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220905 Granted publication date: 20171013 Pledgee: SHANDONG CHAMBROAD PETROCHEMICALS Co.,Ltd. Pledgor: CHAMBROAD CHEMICAL INDUSTRY RESEARCH INSTITUTE Co.,Ltd. Registration number: Y2021980013118 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right |