CN109876854A - A kind of naphthalene liquid-phase oxidation catalyst, preparation method and application - Google Patents
A kind of naphthalene liquid-phase oxidation catalyst, preparation method and application Download PDFInfo
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Abstract
This application discloses a kind of naphthalene liquid-phase oxidation catalysts, the catalyst includes the Beta molecular sieve containing transition metal oxide particle, and its preparation method, preparation method includes: a) gel preparation: structure directing agent, silicon source, silicon source, transition metal precursor, fluoride sources and water are mixed, stirring, form gel, each component molar ratio in the gel are as follows: SiO2/Al2O3=10~1000, M/Si=0.01~2, wherein M is transition metal；B) crystallization: gained gel in step a) is transferred in synthesis reactor, the crystallization 0.5~10 day under the conditions of 110~220 DEG C.Disclosed herein as well is above-mentioned catalyst to be catalyzed the application in Fluidized bed reaction in organic solvent, effectively increases the conversion ratio of naphthalene and the selectivity of purpose product, reaction condition is mild, easy to operate, catalyst is easily prepared pollution-free and recoverable.
Description
Technical field
The present invention relates to a kind of naphthalene liquid-phase oxidation catalysts and its preparation method and application, belong to chemical field.
Background technique
Naphthalene is industrial most important polycyclic aromatic hydrocarbon, and the oxygen-containing organic chemicals synthesized by oxidation reaction are produced in petrochemical industry
In occupation of important position in product.Naphthalene can be converted to naphthols, 1,4- naphthoquinones, phthalic anhydride etc. using oxidation reaction to contain
Oxygen compound, it is the important intermediate and raw material of organic synthesis that these oxygenatedchemicals, which are important Organic Chemicals again, because
The catalysis oxidation of this naphthalene is that one of the important channel of various high level chemicals is produced using naphthalene as raw material.
Naphthalene can be oxidized to naphthols first in the presence of a catalyst, and deep oxidation is 1,4-naphthoquinone and phthalic acid to naphthols again
Acid anhydride, then deep oxidation is cis-butenedioic anhydride until water, carbon monoxide and carbon dioxide etc. again.In the primary product of Fluidized bed, naphthols
It is unstable, oxidation can be continued under the effect of the catalyst and obtain 1,4-naphthoquinone and phthalic anhydride.Therefore the selectivity of naphthols is lower, therefore
The primary product of oxidation is 1,4- naphthoquinones and phthalic anhydride.1,4-naphthoquinone and phthalic anhydride separation are easy, easy to operate, therefore the technology path
It can be used as the green chemical technology of production 1,4-naphthoquinone, economic value, technological value and the value of environmental protection with higher.
The synthesis of 1,4- naphthoquinones at home and abroad has certain research.And 1,4- naphthalene is mainly prepared as raw material using naphthalene
Quinone is mainly the following approach:
(1) naphthalene reoxidizes obtained 1,4-naphthoquinone after being alkylated and alkylnaphthalene is made.
(2) naphthalene is hydrolyzed to naphthols after sulfonated, prepares using metal complex catalyst catalysis oxidation naphthols is crossed
1,4- naphthoquinones.
(3) while naphthalene air Direct Catalytic Oxidation produces phthalic anhydride, a small amount of 1,4-naphthoquinone byproduct is obtained.
(4) naphthalene liquid phase oxidation, that is, high price heavy metallic salt indirect electrolytic oxidation and with the oxidations such as nitric acid, hydrogen peroxide preparation 1,
4- naphthoquinones.
In early days, the production of naphthoquinones is made using the alkyl hydrocarbon oxidation and the oxidation of naphthols of naphthalene, and technical process is multiple
Miscellaneous, the naphthoquinones of production is at high cost.Therefore this method is gradually replaced new production technology.To the fifties later period, due to electricity
Development of the chemical method in terms of organic synthesis using high price heavy metallic salt indirect electrolytic oxidation and uses HNO3、H2O2、IO4 -、
S2O4 2-Equal nonmetal oxides oxidation prepares naphthoquinones acquirement and has arrived better effects.Therefore liquid phase oxidation legal system 1,4- naphthoquinones technology
It is rapidly developed.
For a long time, the liquid phase oxidation of naphthalene needs the participation of the heavy metal based catalysts such as the chromium oxide of stoichiometry, therefore
Industrial wastewater largely containing heavy metal is generated in industrial production, these wastewater treatment process difficulties are many and diverse, will cause to environment
Extremely serious pollution.Since nineteen seventies, research worker attempts to develop novel catalyst, to solve to contain
The problem of chromium waste water, although such research achieves some visible effects, the conversion ratio and Isosorbide-5-Nitrae-of naphthalene in terms of pollution
The selectivity of naphthoquinones is lower.
In general, naphthalene system liquid phase oxidation all avoids the catalyst for having pollution to environment using chromic salts etc., but is
The yield and selectivity for improving target product, are still unavoidable from use to the disagreeableness catalyst of environment or oxidant.Cause
This, the research of the liquid phase catalytic oxidation of naphthalene at present is still to develop suitable catalyst, improves the conversion ratio and purpose oxygen of naphthalene
Change the selectivity of product.
Summary of the invention
In view of the deficiencies of the prior art, the purpose of the present invention is to provide a kind of naphthalene liquid-phase oxidation catalyst and its preparation sides
Method and application.The activity of Fluidized bed catalyst and the selectivity of major oxidation product of this method preparation are improved.
According to an aspect of the invention, there is provided a kind of catalyst of naphthalene liquid phase oxidation, the catalyst includes containing
The Beta molecular sieve of transition metal oxide particle.
According to a further aspect of the invention, it provides and a kind of contains oxo transition metal by what mode of loading in situ synthesized
The preparation method of the Beta molecular sieve of compound particle, is prepared using following steps:
A) prepared by gel: structure directing agent, silicon source, silicon source, transition metal precursor, fluoride sources and water being mixed, stirred
It mixes, forms gel；
B) crystallization: gained gel in step a) is transferred in synthesis reactor, the crystallization 0.5~10 under the conditions of 110~220 DEG C
It；
C) product separates: after product obtained in step b) is centrifuged, washs, it is hollow to be placed in 80~120 DEG C of baking ovens
It is dry under gas atmosphere, and roasted in 500~600 DEG C, obtain the Beta molecular sieve containing transition metal oxide particle.
It preferably, is 2~7 days by crystallization time in step b).
Preferably, the structure directing agent is from tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, tetrapropyl hydrogen-oxygen
Change at least one of ammonium.
Preferably, the silicon source is from least one of aluminum sulfate, sodium aluminate, boehmite.
Preferably, the silicon source is from least one of silica solution, white carbon black, ethyl orthosilicate.
Preferably, the transition metal precursor is the nitrate of the transition metal element M with characteristic of appraising at the current rate.
It is further preferred that the transition metal element M be selected from titanium (Ti), vanadium (V), manganese (Mn), iron (Fe), cobalt (Co),
At least one of nickel (Ni), copper (Cu).
Preferably, the fluorine ion (F-) source be selected from HF, NaF, NH4At least one of F.
Preferably, the molar ratio of each component meets in the gel composition in the step a):
SiO2/Al2O3=10~1000, M/Si=0.01~2, wherein M is transition metal.
It is further preferred that SiO in step a)2/Al2O3=200~500, M/Si=0.01~0.02.
Preferably, crystallization temperature described in step b) is 120~180 DEG C；Crystallization time is 2-7 days.
According to a further aspect of the invention, the catalysis that above-mentioned catalyst and/or the above method are prepared is provided
Agent is used for the application of naphthalene liquid phase oxidation reaction, specific reaction process are as follows: reaction is added in naphthalene, the catalyst, organic solvent
In container, using hydrogen peroxide as oxidant, catalyst aoxidizes naphthalene.
Preferably, 40~150 DEG C of range of reaction temperature, reaction time range 2~10 hours.
Preferably, the organic solvent in acetone, acetic acid, acetonitrile, dimethyl sulfoxide, methylene chloride at least one
Kind.
The beneficial effect comprise that
Beta molecular sieve prepared by the present invention containing transition metal oxide particle is used for naphthalene liquid-phase oxidation catalyst, has
Effect improves the conversion ratio of naphthalene and the selectivity of 1,4- naphthoquinones.
Detailed description of the invention
Fig. 1 is the XRD spectra of the sieve sample prepared in a kind of embodiment of the application.
Fig. 2 is the XRD spectra of the sieve sample prepared in a kind of embodiment of the application.
Fig. 3 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Fig. 4 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Fig. 5 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Fig. 6 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Fig. 7 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Fig. 8 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Fig. 9 is the SEM photograph of the sieve sample prepared in a kind of embodiment of the application.
Specific embodiment
Only the present invention is described further for following embodiment, but the invention is not limited to these embodiments.It is all
Using similar structure of the invention and its similar variation, it is included in the scope of the present invention.
Embodiment 1
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added, is stirred the mixture for using magnetic stir bar
After uniformly, ferric nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.005Al2O3: 0.01Fe2O3: 0.65HF:5H2The solution of O.The solution is transferred to
In stainless steel synthesis reactor equipped with polytetrafluoroethyllining lining, it is placed in 110 DEG C of baking ovens crystallization 10 days.It will be produced in kettle after crystallization
Object filters, is dry, and in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Catalyst.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 1 in Fig. 1, and Electronic Speculum is shone
Piece is shown in Fig. 3.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.60 DEG C are heated to, 30% hydrogen peroxide 2mL is added dropwise, constant temperature is anti-
Answer 6h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 25.3%, the selectivity of naphthols is 5.3%,
The selectivity of 1,4-naphthoquinone is 74.2%, and the selectivity of phthalic anhydride is 15.3%.
Embodiment 2
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added.It is stirred the mixture for using magnetic stir bar
After uniformly, ferric nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.002Al2O3: 0.05Fe2O3: 0.65HF:5H2The solution of O.The solution is transferred to
In stainless steel synthesis reactor equipped with polytetrafluoroethyllining lining, it is placed in 120 DEG C of baking ovens crystallization 7 days.It will be produced in kettle after crystallization
Object filters, is dry, and in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Catalyst.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 2 in Fig. 1, and Electronic Speculum is shone
Piece is shown in Fig. 4.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.80 DEG C are heated to, 30% hydrogen peroxide 2mL is added dropwise, constant temperature is anti-
Answer 6h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 45.3%, the selectivity of naphthols is 4.3%,
The selectivity of 1,4-naphthoquinone is 70.2%, and the selectivity of phthalic anhydride is 18.1%.
Embodiment 3
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added, is stirred the mixture for using magnetic stir bar
After uniformly, ferric nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.003Al2O3: 0.01Fe2O3: 0.65HF:5H2The solution of O.The solution is transferred to
In stainless steel synthesis reactor equipped with polytetrafluoroethyllining lining, it is placed in 140 DEG C of baking ovens crystallization 7 days.It will be produced in kettle after crystallization
Object filters, is dry, and in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Catalyst.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 3 in Fig. 1, and Electronic Speculum is shone
Piece is shown in Fig. 5.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.100 DEG C are heated to, 30% hydrogen peroxide 2mL, constant temperature is added dropwise
React 4h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 35.3%, and the selectivity of naphthols is
21.4%, the selectivity of 1,4-naphthoquinone is 54.2%, and the selectivity of phthalic anhydride is 16.1%.
Embodiment 4
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added, is stirred the mixture for using magnetic stir bar
After uniformly, ferric nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.10Al2O3: 0.02Fe2O3: 0.65HF:5H2The solution of O.The solution is transferred to and is matched
Have in the stainless steel synthesis reactor of polytetrafluoroethyllining lining, is placed in 150 DEG C of baking ovens crystallization 7 days.By product in kettle after crystallization
It filters, is dry, and being urged in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Agent.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 4 in Fig. 1, electromicroscopic photograph
See Fig. 6.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.120 DEG C are heated to, 30% hydrogen peroxide 2mL, constant temperature is added dropwise
React 2h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 25.3%, and the selectivity of naphthols is
4.4%, the selectivity of 1,4-naphthoquinone is 73.2%, and the selectivity of phthalic anhydride is 16.5%.
Embodiment 5
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added, is stirred the mixture for using magnetic stir bar
After uniformly, ferric nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.002Al2O3: 0.02Fe2O3: 0.65HF:5H2The solution of O.The solution is transferred to
In stainless steel synthesis reactor equipped with polytetrafluoroethyllining lining, it is placed in 180 DEG C of baking ovens crystallization 5 days.It will be produced in kettle after crystallization
Object filters, is dry, and in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Catalyst.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 5 in Fig. 2, and Electronic Speculum is shone
Piece is shown in Fig. 7.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.40 DEG C are heated to, 30% hydrogen peroxide 2mL is added dropwise, constant temperature is anti-
Answer 10h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 25.8%, and the selectivity of naphthols is
10.4%, the selectivity of 1,4-naphthoquinone is 70.9%, and the selectivity of phthalic anhydride is 13.7%.
Embodiment 6
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added, is stirred the mixture for using magnetic stir bar
After uniformly, cobalt nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.005Al2O3: 0.01CoO2: 0.65HF:5H2The solution of O.The solution is transferred to and is matched
Have in the stainless steel synthesis reactor of polytetrafluoroethyllining lining, is placed in 220 DEG C of baking ovens crystallization 1 day.By product in kettle after crystallization
It filters, is dry, and being urged in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Agent.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 6 in Fig. 2, electromicroscopic photograph
See Fig. 8.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.80 DEG C are heated to, 30% hydrogen peroxide 2mL is added dropwise, constant temperature is anti-
Answer 6h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 18.7%, the selectivity of naphthols is 11.2%,
The selectivity of 1,4-naphthoquinone is 24.2%, and the selectivity of phthalic anhydride is 45.3%.
Embodiment 7
After TEAOH solution is mixed with 10g deionized water, hydrofluoric acid is added, is stirred the mixture for using magnetic stir bar
After uniformly, cobalt nitrate, ethyl orthosilicate and aluminum sulfate is added.4h is stirred the mixture under the conditions of 60 DEG C of waters bath with thermostatic control, is obtained
Ratio of components is 0.5TEAOH:1.0SiO2: 0.0001Al2O3: 0.02CoO2: 0.65HF:5H2The solution of O.The solution is transferred to
In stainless steel synthesis reactor equipped with polytetrafluoroethyllining lining, it is placed in 140 DEG C of baking ovens crystallization 7 days.It will be produced in kettle after crystallization
Object filters, is dry, and in 550 DEG C of roasting 5h in Muffle furnace to get to the Beta molecular sieve containing transition metal oxide particle
Catalyst.The XRD spectrum for the Beta molecular sieve catalyst that the present embodiment is prepared is shown in the map of the number 7 in Fig. 2, and Electronic Speculum is shone
Piece is shown in Fig. 9.
The catalyst of above-mentioned preparation is used for naphthalene liquid phase oxidation reaction.Specific implementation process are as follows: burnt in the round bottom of 250mL
In bottle, 0.8g naphthalene, acetic acid 25mL, catalyst 0.2g is added.150 DEG C are heated to, 30% hydrogen peroxide 2mL is added dropwise, is kept the temperature
React 2h.It is formed with chromatographic product.It as a result is that the conversion ratio of naphthalene is 28.6%, and the selectivity of naphthols is
15.3%, the selectivity of 1,4-naphthoquinone is 30.2%, and the selectivity of phthalic anhydride is 40.6%.
The above is only several embodiments of the application, not does any type of limitation to the application, although this Shen
Please disclosed as above with preferred embodiment, however not to limit the application, any person skilled in the art is not taking off
In the range of technical scheme, a little variation or modification are made using the technology contents of the disclosure above and is equal to
Case study on implementation is imitated, is belonged in technical proposal scope.
Claims (10)
1. a kind of naphthalene liquid-phase oxidation catalyst, which is characterized in that the catalyst includes containing transition metal oxide particle
Beta molecular sieve.
2. the preparation method of catalyst described in claim 1, which is characterized in that described containing transition metal oxide particle
The synthetic method of Beta molecular sieve, at least includes the following steps:
A) prepared by gel: structure directing agent, silicon source, silicon source, transition metal precursor, fluoride sources and water being mixed, stirring, shape
At gel, each component molar ratio in the gel are as follows:
SiO2/Al2O3=10~1000, M/Si=0.01~2, wherein M is transition metal；
B) crystallization: gained gel in step a) is transferred in synthesis reactor, the crystallization 0.5~10 day under the conditions of 110~220 DEG C；
Preferably, crystallization time is 2~7 days in step b)；
C) product separates: after product obtained in step b) is centrifuged, washs, being placed in air gas in 80~120 DEG C of baking ovens
It is dry under atmosphere, and roasted in 500~600 DEG C, obtain the Beta molecular sieve containing transition metal oxide particle.
3. according to the method described in claim 2, it is characterized in that, the structure directing agent is selected from tetramethylammonium hydroxide, four
At least one of ethyl ammonium hydroxide, tetrapropylammonium hydroxide.
4. according to the method described in claim 2, it is characterized in that, source of aluminium is selected from aluminum sulfate, sodium aluminate, boehmite
At least one of.
5. according to the method described in claim 2, it is characterized in that, the silicon source is selected from silica solution, white carbon black, ethyl orthosilicate
At least one of.
6. according to the method described in claim 2, it is characterized in that, the transition metal precursor is the mistake with characteristic of appraising at the current rate
Cross the nitrate of metallic element M；
Preferably, the transition metal element M is selected from least one of titanium, vanadium, manganese, iron, cobalt, nickel, copper.
7. according to the method described in claim 2, it is characterized in that, the fluoride sources are selected from HF, NaF, NH4At least one in F
Kind.
8. the catalyst conduct that any one of catalyst described in claim 1 and/or claim 2 to 7 the method is prepared
The application of naphthalene liquid-phase catalytic oxidation catalyst, which is characterized in that reaction is added in naphthalene, the catalyst, organic solvent and is held
In device, using hydrogen peroxide as oxidant, catalyst aoxidizes naphthalene.
9. application according to claim 8, which is characterized in that 40~150 DEG C of range of reaction temperature, reaction time range is
2~10 hours.
10. application according to claim 8, which is characterized in that the organic solvent is selected from acetone, acetic acid, acetonitrile, diformazan
At least one of base sulfoxide, methylene chloride.
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