CN110183308A - A kind of non-metallic catalyst, preparation method and application preparing phenol for benzene direct oxidation - Google Patents
A kind of non-metallic catalyst, preparation method and application preparing phenol for benzene direct oxidation Download PDFInfo
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- CN110183308A CN110183308A CN201910462783.8A CN201910462783A CN110183308A CN 110183308 A CN110183308 A CN 110183308A CN 201910462783 A CN201910462783 A CN 201910462783A CN 110183308 A CN110183308 A CN 110183308A
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
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- C07C37/58—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 molecular oxygen
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Abstract
A kind of non-metallic catalyst preparing phenol for benzene direct oxidation prepares its application method, and 1,4-benzoquinone and diamines are dissolved in methanol by this method respectively；Then after mixing by the two solution, Xiang Suoshu mixed solution and dripping hydrogen peroxide；And transfer them in autoclave, 4~12h, the non-metallic catalyst obtained after filtering are reacted at 120 DEG C~160 DEG C；The non-metallic catalyst is under conditions of acetic acid aqueous solution is solvent, acetate is additive, at 120 DEG C~150 DEG C, can prepare phenol with oxygen catalytic oxidation benzene, obtain preferable phenol yield.The nonmetal catalyzed of this method preparation can prepare phenol with oxygen catalytic oxidation benzene, so as to avoid the use containing heavy metal catalyst.
Description
Technical field
The invention belongs to new catalyst preparation and field of energy and chemical technologys, and in particular to one kind is used for the direct oxygen of benzene
The non-metallic catalyst that change prepares phenol prepares its application.
Background technique
Phenol is a kind of important large basic material of chemical intermediate and petrochemical industry.Currently, the industrial production of phenol
Method is mainly cumene method, there are reaction process it is long, atom utilization is not high, gross production rate is lower (< 5%) the shortcomings that.Cause
This, in recent years, countries in the world are dedicated to studying a kind of environment-friendly preparation method thereof of phenol, and wherein benzene direct oxidation prepares phenol conduct
A kind of economical and eco-friendly phenol novel preparation method gets more and more people's extensive concerning.A kind of oxidant of the oxygen as green, has
The advantages that from a wealth of sources, cheap, and its oxidation product is water, will not generate the by-product of environmental pollution.Therefore, with oxygen
Gas is oxidant, and direct oxidation benzene prepares phenol with important theory and actual application meaning.
It is the catalyst containing transition metal that benzene oxidatoin, which prepares the catalyst generally used in the reaction of phenol all,.Patent
In CN102921419A, phenol is prepared with the loaded catalyst catalysis benzene oxidatoin of cupric；In patent CN102228833A, to contain
There is the porous material of cobalt to prepare phenol as catalyst benzene oxidatoin；In patent CN104926614A, with the metal containing copper
Organic frame compound HKUST-1 is that catalyst benzene oxidatoin prepares phenol；Document report is containing transition metal such as vanadium, iron, palladiums
Catalyst dioxygen oxidation benzene prepare phenol [(a) Wang WT, Li N, Tang H, et al. Molecular
catalysis, 2018,453,113-120; (b) Qin Q, Liu YQ, Shan WJ, et al. Industrial &
Engineering Chemistry Research, 2017, 56 (43), 12289-12296; Shang SS, Yang H,
Li J, et al. Chempluschem 2014, 79 (5), 680-683.].Dioxygen oxidation benzene prepares the reaction one of phenol
As carried out in acid reaction dissolvent.Metallic catalyst is easy to appear activated centre loss in acid flux material, causes to be catalyzed
Activity reduces, generates the problems such as pollution of heavy metal ion, and catalyst stability is difficult to be guaranteed, and increases the production of phenol
Cost is attracted attention at economical and environmentally friendly aspect.This just promotes us to go to develop a kind of non-metallic catalyst, answers
In research for green phenol processed.Up to the present, non-metallic catalyst is prepared with 1,4-benzoquinone and diamines, and is catalysis with it
The document that agent oxygen catalytic oxidation benzene prepares phenol does not have been reported that.
Summary of the invention
In order to overcome the above-mentioned deficiencies of the prior art, the object of the present invention is to provide one kind prepares benzene for benzene direct oxidation
The non-metallic catalyst of phenol prepares its application method, and avoiding makes in benzene direct oxidation phenol reactant containing metallic catalyst
With the problem of avoiding metal loss, improving the stability of catalyst, and prepared catalyst is in oxygen catalytic oxidation benzene
It prepares and shows preferable phenol yield in the reaction of phenol.
In order to achieve the above object, the technical solution adopted by the present invention is that:
A kind of non-metallic catalyst preparing phenol for benzene direct oxidation prepares its application method, and the catalyst is to benzene
The non-metallic catalyst that quinone and diamines are prepared as raw material, activated centre are benzoquinones and quinhydrones, realize oxygen direct oxidation
Benzene prepares the nonmetal catalyzed of phenol.
In order to achieve the above objectives, the present invention adopts the following technical scheme:
A kind of non-metallic catalyst preparation method preparing phenol for benzene direct oxidation, comprising the following steps:
Step 1: it by 1,4-benzoquinone and diamines according to the molar ratio of 6:1~1.5:1, is dissolved in methanol solution respectively, obtains 1,4-benzoquinone
Methanol solution A and diamines methanol solution B；
Step 2: the solution A that step 1 is obtained is added in solution B, and is stirred evenly, and solution C is obtained；
Step 3: into the solution C that step 2 obtains, 1~3mL of hydrogen peroxide is added dropwise and transfers the solution into high pressure after mixing evenly
In reaction kettle；
Step 4: being added 4~12h for autoclave at 120 DEG C~160 DEG C, after obtained solid product filtering, with methanol and steaming
It is colorless and transparent rear drying to get non-metallic catalyst that distilled water, which is washed till filtrate,.
Further, the molar ratio of the 1,4-benzoquinone and diamines is 6:1~1.5:1.
Further, the diamines includes ethylenediamine, propane diamine, hexamethylene diamine, o-phenylenediamine, melamine.
Further, it is 10~30% that the hydrogen peroxide, which is mass concentration, and dosage is 1~3mL.
Further, step 4 kind heating temperature is 120 DEG C~160 DEG C, and the time is 4~12h.
A kind of non-metallic catalyst preparing phenol for benzene direct oxidation, by the preparation side of above-mentioned solid acid catalyst
Method is made.
A kind of catalytic applications method based on above-mentioned non-metallic catalyst, comprising the following steps:
Step 1: non-metallic catalyst described in 0.025~0.2g of addition in a high pressure reaction kettle, the benzene of 0.5mL~1.0mL, 0.2
The acetate of~0.8g, the acetic acid aqueous solution that the volume fraction of 3.0mL is 50%~100%；
Step 2: the oxygen pressure of 1.0~4.0MPa is filled with into reaction kettle；
Step 3: it by the reaction kettle at 120 DEG C~150 DEG C, is stirred to react 12~24 hours, phenol product can be arrived.
Further, the acetate in step 1 is lithium acetate and sodium acetate, and dosage is 0.2~0.8g.
Further, the reaction dissolvent in step 1 is the acetic acid aqueous solution that volumetric concentration is 50%~100%.
Further, the oxygen pressure in step 2 is 1.0~4.0MPa.
Further, the reaction temperature in step 3 is 120 DEG C~150 DEG C.
Compared with prior art, the invention has the following beneficial technical effects:
The present invention can be prepared nonmetal catalyzed using benzoquinones and diamines as simple raw material by simple polymerization reaction
Agent, the activated centre of the non-metallic catalyst are mainly quinone-quinhydrones functional group contained by it.The non-metallic catalyst can be straight
It connects and prepares phenol as catalyst dioxygen oxidation benzene, avoid the use of metallic catalyst and the loss of heavy metal to environment
Pollution；The yield that its oxygen catalytic oxidation benzene prepares phenol, which can achieve, prepares the identical of phenol with metallic catalyst catalysis benzene
Level, with preferable catalytic activity；In addition, the method for preparing catalyst is simple, efficient, it is convenient, high with catalytic activity,
The advantages that high income.
Detailed description of the invention
Fig. 1 is the FT-IR figure of the quinone-amine polymer of different amine sources preparation.(a) ethylenediamine in figure, (b) propane diamine, (c) oneself
Diamines, (d) o-phenylenediamine, (e) melamine.
Fig. 2 is the SEM spectrum for the non-metallic catalyst that the present invention obtains.
Specific embodiment
Below with reference to the embodiment content that the present invention is furture elucidated.
Embodiment 1
30mmol 1,4-benzoquinone and 10mmol ethylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
3 MPa O are filled under temperature2, in 120 DEG C of 24 h of reaction, the yield for obtaining phenol is 13.1%.
Embodiment 2
20mmol 1,4-benzoquinone and 10mmol ethylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
3 MPa O are filled under temperature2, in 120 DEG C of 12 h of reaction, the yield for obtaining phenol is 5.4%.
Embodiment 3
30mmol 1,4-benzoquinone and 10mmol propane diamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
3 MPa O are filled under temperature2, in 120 DEG C of 12 h of reaction, the yield for obtaining phenol is 15.9%.
Embodiment 4
30mmol 1,4-benzoquinone and 10mmol hexamethylene diamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
2 MPa O are filled under temperature2, in 120 DEG C of 12 h of reaction, the yield for obtaining phenol is 15%.
Embodiment 5
30mmol 1,4-benzoquinone and 10mmol o-phenylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
2 MPa O are filled under temperature2, in 120 DEG C of 12 h of reaction, the yield for obtaining phenol is 5.1%.
Embodiment 6
30mmol 1,4-benzoquinone and 10mmol ethylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 2 mL 20%(wt. are slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 130 DEG C of 7 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
3 MPa O are filled under temperature2, in 120 DEG C of 12 h of reaction, the yield for obtaining phenol is 5.2%.
Embodiment 7
30mmol 1,4-benzoquinone and 10mmol ethylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.2 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
3 MPa O are filled under temperature2, in 120 DEG C of 24 h of reaction, the yield for obtaining phenol is 6.4%.
Embodiment 8
30mmol 1,4-benzoquinone and 10mmol ethylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g lithium acetate, which are added to volume fraction,
2 MPa O are filled under temperature2, in 140 DEG C of 24 h of reaction, the yield for obtaining phenol is 12.9%.
Embodiment 9
30mmol 1,4-benzoquinone and 10mmol ethylenediamine are dissolved in methanol respectively, 1,4-benzoquinone solution is added to ethylenediamine solution
In, after mixing evenly, 1 mL 30%(wt. is slowly added dropwise) H2O2.Agitating solution is allowed to be sufficiently mixed, and solution is transferred to outfit
In the autoclave of polytetrafluoroethyllining lining, in 120 DEG C of 5 h of heating.After obtained product filtering, washed with 30 mL methanol
It washs, 80 DEG C are dried overnight, and obtain non-metallic catalyst.
It is room in 70% acetic acid solution that 0.1 g catalyst, 0.5 mL benzene, 0.4 g sodium acetate, which are added to volume fraction,
2 MPa O are filled under temperature2, in 120 DEG C of 12 h of reaction, the yield for obtaining phenol is 14.3%.
Claims (10)
1. a kind of preparation method for the non-metallic catalyst for preparing phenol for benzene direct oxidation, which is characterized in that including following
Step:
It disperses 1,4-benzoquinone, diamine organic matter and hydrogen peroxide in enough organic solvents, 120 DEG C~160 DEG C progress solvents
Thermal response obtains non-metallic catalyst.
2. a kind of preparation method of non-metallic catalyst that phenol is prepared for benzene direct oxidation according to claim 1,
It is characterized in that, the molar ratio of 1,4-benzoquinone and diamine organic matter is (6 ~ 1.5): 1.
3. a kind of preparation method of non-metallic catalyst that phenol is prepared for benzene direct oxidation according to claim 1,
It is characterized in that, diamine organic matter is one of ethylenediamine, propane diamine, hexamethylene diamine, o-phenylenediamine, melamine or more
Kind.
4. a kind of preparation method of non-metallic catalyst that phenol is prepared for benzene direct oxidation according to claim 1,
It is characterized in that, the mass concentration of the hydrogen peroxide is 10%~30%.
5. a kind of preparation method of non-metallic catalyst that phenol is prepared for benzene direct oxidation according to claim 1,
It is characterized in that, solvent used by solvent thermal reaction be methanol, reaction temperature be 120 DEG C~160 DEG C, the reaction time be 4~
12 hours.
6. the system of described in any item a kind of non-metallic catalysts for preparing phenol for benzene direct oxidation according to claim 1 ~ 5
Preparation Method, which is characterized in that specific steps include:
Step 1: it by 1,4-benzoquinone and diamine organic matter according to the molar ratio of 6:1~1.5:1, is dissolved in methanol solution, obtains respectively
To the methanol solution A of the 1,4-benzoquinone and methanol solution B of diamine organic matter；
Step 2: the solution A that step 1 is obtained is added in solution B, and is stirred evenly, and solution C is obtained；
Step 3: into the solution C that step 2 obtains, dropwise addition mass concentration is 10%~30% 1~3mL of hydrogen peroxide, is stirred evenly
Afterwards, it transfers the solution into autoclave；
Step 4: autoclave is reacted into 4~12h, the solid product obtained after filtering, with methanol and steaming at 120 DEG C~160 DEG C
It is colorless and transparent rear drying to get non-metallic catalyst that distilled water, which is washed till filtrate,.
7. a kind of non-metallic catalyst for preparing phenol for benzene direct oxidation, which is characterized in that any by claim 1~6
Item the method is made.
8. the application that a kind of non-metallic catalyst described in claim 7 is used to prepare phenol.
9. the application that a kind of non-metallic catalyst according to claim 8 is used to prepare phenol, which is characterized in that including with
Lower step:
It containing benzene, acetate, the acetic acid aqueous solution that volumetric concentration is 50%~100% and as claimed in claim 7 nonmetallic will urge
The dispersion of agent is placed in high-pressure bottle；The oxygen of 1.0MPa pressure above is filled with to high-pressure bottle；Enable reaction system 120
DEG C~150 DEG C sufficiently reaction to get arrive phenol.
10. the application that a kind of non-metallic catalyst according to claim 9 is used to prepare phenol, which is characterized in that specific
Step includes:
Step 1: non-metallic catalyst described in 0.025~0.2g of addition in a high pressure reaction kettle, the benzene of 0.5~1.0mL, 0.2~
The acetate of 0.8g, the acetic acid aqueous solution that the volumetric concentration of 3.0mL is 50%~100%；
Step 2: the oxygen pressure of 1.0~4.0MPa is filled with into reaction kettle；
Step 3: it by the reaction kettle at 120 DEG C~150 DEG C, is stirred to react 12~24 hours, phenol product can be arrived；
The acetate is one of lithium acetate, sodium acetate or a variety of.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105734A (en) * | 2021-11-19 | 2022-03-01 | 浙江工业大学 | Method for continuous flow synthesis of 2-chloro hydroquinone |
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| US5606010A (en) * | 1994-07-07 | 1997-02-25 | Semih Erhan | Methods for the preparation of inherently metal binding poly-amine-quinone polymers |
| CN106831352A (en) * | 2016-12-19 | 2017-06-13 | 江苏师范大学 | A kind of method of the direct phenol processed of dioxygen oxidation benzene |
| CN107519910A (en) * | 2017-09-12 | 2017-12-29 | 陕西科技大学 | It is a kind of to prepare support type vanadic acid Zr catalyst of phenol and preparation method thereof for oxygen direct oxidation benzene |
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2019
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| US5606010A (en) * | 1994-07-07 | 1997-02-25 | Semih Erhan | Methods for the preparation of inherently metal binding poly-amine-quinone polymers |
| CN106831352A (en) * | 2016-12-19 | 2017-06-13 | 江苏师范大学 | A kind of method of the direct phenol processed of dioxygen oxidation benzene |
| CN107519910A (en) * | 2017-09-12 | 2017-12-29 | 陕西科技大学 | It is a kind of to prepare support type vanadic acid Zr catalyst of phenol and preparation method thereof for oxygen direct oxidation benzene |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105734A (en) * | 2021-11-19 | 2022-03-01 | 浙江工业大学 | Method for continuous flow synthesis of 2-chloro hydroquinone |
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