CN109621945A - It is a kind of for toluene oxidation be benzoic acid novel nano catalyst - Google Patents
It is a kind of for toluene oxidation be benzoic acid novel nano catalyst Download PDFInfo
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- CN109621945A CN109621945A CN201811622034.9A CN201811622034A CN109621945A CN 109621945 A CN109621945 A CN 109621945A CN 201811622034 A CN201811622034 A CN 201811622034A CN 109621945 A CN109621945 A CN 109621945A
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- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
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- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
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- 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
- B01J23/83—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 rare earths or actinides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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Abstract
It is the novel nano catalyst of benzoic acid that the invention discloses a kind of for toluene oxidation, the catalyst is using composite oxide of metal as carrier, using the transition metal of high activity as catalytic oxidation activity center, using rare earth metal as co-catalysis activated centre, the transition metal element of the high activity is one or both of Mn, Cr, Cu, Co, Ni, Fe, its content accounts for the 0 ~ 3% of catalyst gross mass, the thulium is one or both of Sc, Y, La, Ce, Pr, Nd, and content accounts for the 0 ~ 2% of catalyst gross mass.The invention also discloses a kind of preparation methods using carbon dioxide production novel nano catalyst；And catalyst preparation process of the invention is simple, at low cost, reaction condition is mild, does not generate pollution to environment；Gained catalyst activity is high, stability is good, can efficiently produce toluene oxidation product benzoic acid, and consume GHG carbon dioxide in catalyst preparation process, not only reduce carbon emission, and obtain efficient novel nano catalyst.
Description
Technical field
It is the novel nano catalyst of benzoic acid that the present invention relates to a kind of for toluene oxidation.
Background technique
Volatile organic compounds (VOCs) is common one of exhaust gas, mainly from petrochemical industry, paint production, metal
The production fields such as coating, printing, evaporate into atmosphere and not only pollute the environment, and can also be detrimental to health.Numerous indoor dirty
It contaminates among object, toluene is one of common volatile organic compounds (VOCs).Occupy indoor building material, ornament materials, artificial
Plate furniture etc. can give out the harmful substances such as aldehydes, compound fragrant hydrocarbon, wherein most with compound fragrant hydrocarbon (such as: toluene)
For protrusion, if converting chemical products or chemical intermediate for VOCs, not only contribute to environmental protection and can becoming give up into
It is precious.
Toluene is that maximum is endangered in VOCs, pollutes most heavy one of ingredient, and catalysis oxidation can produce benzyl alcohol, benzene first
The fine chemical product of the high added values such as aldehyde, benzoic acid, Ergol.Wherein benzoic acid can be widely used in medicine, solvent,
Dyestuff, plasticizer, the fields such as preservative, fire retardant.Suib etc. utilizes γ-MnO2For catalyst, it is with the oxygen stream of flowable state
Oxidant, azodiisobutyronitrile (AIBN) is radical initiator, using circumfluence method in 110 DEG C of condition selective oxidation toluene,
But toluene conversion only has 17.6%, and the selectivity of benzoic acid is only 58%.Liao's bean is vigorously equal with manganese acetate, glacial acetic acid and Gao Meng
Sour potassium is raw material, has synthesized Mn oxide, and using it as catalyst, using TBHP as oxidant, in returning for solvent-free normal pressure
Selective catalytic oxidation toluene under fluid system reacts 48 h under optimum reaction condition, and toluene conversion reaches 44.67%, mesh
The selectivity of mark product benzoic acid reaches 79.18%.But be required to be added in these catalyst systems homogeneous azodiisobutyronitrile or
TBHP, will lead to product separation difficulty, and three waste discharge is serious.Explore the toluene alkylation synthesizing benzoic acids of green high-efficient
Catalyst system is still problem urgently to be resolved.
Therefore, using molecular oxygen as oxidant, multi-phase selective aoxidizes toluene synthesizing benzoic acids and will anticipate with far-reaching environmental protection
Justice and industrial value.
Summary of the invention
1, problems to be solved by the invention
For production benzoic acid Existing methods the problem of, it for toluene oxidation is benzoic acid that the present invention, which provides a kind of,
Novel nano catalyst.
2, technical solution
It is a kind of for toluene oxidation be benzoic acid novel nano catalyst, it is characterised in that: the catalyst is with metal composite oxygen
Compound is carrier, using the transition metal of high activity as catalytic oxidation activity center, using rare earth metal as co-catalysis activated centre, and institute
The transition metal element for stating high activity is one or both of Mn, Cr, Cu, Co, Ni, Fe, and content accounts for catalyst gross mass
0 ~ 3%, the thulium is one or both of Sc, Y, La, Ce, Pr, Nd, and content accounts for the total matter of catalyst
The 0 ~ 2% of amount.
The above-mentioned preparation method for the novel nano catalyst that toluene conversion is benzoic acid includes the following steps:
(1) the complex colloid aqueous solution for preparing bivalent metal oxide, aluminium oxide and lye, controls bivalent metal oxide and oxygen
Change the molar ratio of aluminium 2.0~6.0, controls the total concentration of lye in 2.0~15.0 mol/L, control the molal quantity of lye as gold
Belong to 1~3 times of oxide total mole number；
(2) gained colloidal solution is put into three-necked flask and is stirred to react 12~48 hours, control temperature at 60~150 DEG C, and
It is continually fed into CO2, controlling its flow velocity is 10~100 mL/min, obtains required colloid, then the mistake of high activity is added in colloid
Metal salt and rare earth metal salt are crossed, the reaction was continued 4~10 hours, and temperature is controlled at 25 ~ 100 DEG C, then subtracts resulting colloid
Pressure revolving, is placed in 80~120 DEG C of drying 6-24 hours for solid sample；
(3) resulting solid sample is placed in the tube furnace of logical reducing gas and is calcined 4~12 hours, control temperature 400~
750 DEG C, obtain required catalyst.
Further, in above-mentioned steps (1), the bivalent metal oxide can be one of Ba, Ca, Mg, Zn
Or two kinds；The lye can be LiOH, NaOH, KOH, NH4One or both of OH.
Further, in above-mentioned steps (2), the transition metal salt can be the nitric acid of Mn, Cr, Cu, Co, Ni, Fe
One or both of salt, chloride or acetate.
Further, in above-mentioned steps (2), the rare earth metal salt can be the nitric acid of Sc, Y, La, Ce, Pr, Nd
One or both of salt, chloride.
Further, in above-mentioned steps (3), the reducing gas can be H2, CO or CH4One of.
3, beneficial effect
The present invention has the following advantages compared with existing catalyst:
(1) GHG carbon dioxide is consumed in catalyst preparation process, not only reduces carbon emission, and obtained efficient novel
Nanocatalyst；
(2) catalyst preparation is simple, cheap, there is extensive industrial applications prospect；
(3) discharging of waste liquid is not generated in production process, pollution is not generated to environment.
Specific embodiment
The relatively mild reaction conditions are as follows: 500 mL first are added in the reaction under high pressure reaction kettle with polytetrafluoro liner
Benzene, the catalyst of 20 ~ 100 g, stirring are passed through oxygen after five minutes, will be heated to assigned temperature in the reaction kettle 5 minutes.Reaction
For temperature range at 100 ~ 160 DEG C, the reaction time is 6 ~ 24 hours, and air or oxygen pressure is 0.5 ~ 4.0 MPa.
Product analysis, GC conditions are as follows: 6890 gas-chromatography of the Agilent (μ m of capillary column 30mm × 320
0.25 μm), 80 DEG C of column temperature, temperature programming: 80 DEG C of initial temperature, 20 DEG C/min to 280 DEG C of the first stage, continue 5min.
Carrier gas is N2, 1 mL/min of flow velocity, hydrogen ion flame detector, automatic sampling, 0.1 μ L of sample volume, by normalization method to each
Product carries out quantitative analysis.
Case is embodied
Embodiment 1
6 mol magnesia, 3 mol aluminium oxide, the LiOH for separately taking 9 mol are taken, the colloid aqueous solution of 4.5 L is made into；By gained glue
Liquid solution, which is put into large beaker, to be stirred to react 12 hours, and temperature is controlled at 60 DEG C, is continually fed into CO2, controlling its flow velocity is 10
ML/min obtains required colloid, then 0.13 g manganese acetate and 0.07g scandium nitrate are added into colloid, and the reaction was continued 4 hours, temperature
Degree control is at 25 DEG C, and then by resulting colloid vacuum rotary steam, 80 DEG C of obtained solid are dried 6 hours；By resulting solid-like
Product are placed in logical H2Tube furnace in calcine 4 hours, temperature control at 400 DEG C, obtain required catalyst.Described is relatively mild
Reaction condition are as follows: 500 mL toluene are added in the autoclave with polytetrafluoro liner, the catalyst of 20 g stirs 5 points
It is passed through oxygen after clock, assigned temperature will be heated in the reaction kettle 5 minutes.Reaction temperature is at 100 DEG C, and the reaction time 6 is small
When, oxygen pressure is 0.5 MPa, after centrifugal filtration, takes 10 uL samples to analyze in 6890 gas-chromatography of Agilent, toluene
Conversion ratio is 37.8%, and the selectivity of benzoic acid is up to 96.7%.
Embodiment 2
18 mol barium monoxide, 3 mol aluminium oxide, the NaOH for separately taking 126 mol are taken, the colloid aqueous solution of 8.4 L is made into；By gained
Colloidal solution, which is put into large beaker, to be stirred to react 48 hours, and temperature is controlled at 150 DEG C, is continually fed into CO2, controlling its flow velocity is
100 mL/min obtain required colloid, then 0.9 g chromium chloride and 0.42g yttrium nitrate are added into colloid, and it is 10 small that the reaction was continued
When, temperature is controlled at 100 DEG C, and then by resulting colloid vacuum rotary steam, 120 DEG C of obtained solid are dried 24 hours；By gained
Solid sample be placed in the tube furnace of logical CO and calcine 12 hours, temperature is controlled at 750 DEG C, obtains required catalyst.It is described
Relatively mild reaction conditions are as follows: with polytetrafluoro liner autoclave in 500 mL toluene, the catalysis of 100 g is added
Agent, stirring are passed through oxygen after five minutes, will be heated to assigned temperature in the reaction kettle 5 minutes.Reaction temperature is at 160 DEG C, instead
24 hours between seasonable, oxygen pressure is 4 MPa, after centrifugal filtration, 10 uL samples is taken to divide in 6890 gas-chromatography of Agilent
Analysis, toluene conversion 67.8%, the selectivity of benzoic acid is up to 76.7%.
Embodiment 3
9 mol calcium oxide, 3 mol aluminium oxide, the NaOH for separately taking 36 mol are taken, the colloid aqueous solution of 18 L is made into；By gained glue
Liquid solution, which is put into large beaker, to be stirred to react 24 hours, and temperature is controlled at 100 DEG C, is continually fed into CO2, controlling its flow velocity is 60
ML/min obtains required colloid, then 0.5 g copper chloride and 0.3g lanthanum nitrate are added into colloid, and the reaction was continued 8 hours, temperature
Control is at 80 DEG C, and then by resulting colloid vacuum rotary steam, 100 DEG C of obtained solid are dried 12 hours；By resulting solid-like
Product are placed in logical CH4Tube furnace in calcine 6 hours, temperature control at 450 DEG C, obtain required catalyst.Described is relatively mild
Reaction condition are as follows: 500 mL toluene are added in the autoclave with polytetrafluoro liner, the catalyst of 80 g stirs 5 points
It is passed through oxygen after clock, assigned temperature will be heated in the reaction kettle 5 minutes.Reaction temperature is at 100 DEG C, and the reaction time 6 is small
When, oxygen pressure is 2.0 MPa, after centrifugal filtration, takes 10 uL samples to analyze in 6890 gas-chromatography of Agilent, toluene
Conversion ratio is 47.8%, and the selectivity of benzoic acid is up to 89.7%.
Embodiment 4
The KOH of 4.5 mol zinc oxide, 4.5 mol magnesia, 3 mol aluminium oxide, the another NaOH and 18 mol for taking 18 mol are taken,
It is made into the colloid aqueous solution of 18 L；Gained colloidal solution is put into large beaker and is stirred to react 24 hours, temperature is controlled 100
DEG C, it is continually fed into CO2, controlling its flow velocity is 60 mL/min, obtain required colloid, then be added into colloid 0.25 g cobalt chloride,
0.25 g nickel chloride and 0.3g cerous nitrate, the reaction was continued 6 hours, and temperature is controlled at 60 DEG C, then depressurizes resulting colloid and revolves
It steams, 100 DEG C of obtained solid dry 12 hours；Resulting solid sample is placed in logical H2Tube furnace in calcine 6 hours, temperature
Control obtains required catalyst at 450 DEG C.The relatively mild reaction conditions are as follows: anti-in the high pressure with polytetrafluoro liner
It answers and 500 mL toluene is added in kettle, the catalyst of 30 g, stirring is passed through oxygen after five minutes, will be heated in the reaction kettle 5 minutes
Assigned temperature.Reaction temperature is the reaction time 6 hours at 100 DEG C, and oxygen pressure is 2.0 MPa, after centrifugal filtration, takes 10
UL sample is analyzed in 6890 gas-chromatography of Agilent, and toluene conversion 45.8%, the selectivity of benzoic acid is up to 91.7%.
Embodiment 5
Take 4.5 mol zinc oxide, 4.5 mol magnesia, 3 mol aluminium oxide, the NH for separately taking 18 mol4The KOH of OH and 18 mol,
It is made into the colloid aqueous solution of 18 L；Gained colloidal solution is put into large beaker and is stirred to react 24 hours, temperature is controlled 100
DEG C, it is continually fed into CO2, controlling its flow velocity is 60 mL/min, obtain required colloid, then be added into colloid 0.25 g copper nitrate,
0.25 g iron chloride, 0.13 g cerous nitrate and 0.17 g neodymium chloride, the reaction was continued 6 hours, and temperature is controlled at 60 DEG C, then will
Resulting colloid vacuum rotary steam, 100 DEG C of obtained solid dry 12 hours；Resulting solid sample is placed in logical H2Tube furnace
Middle calcining 6 hours, temperature is controlled at 450 DEG C, obtains required catalyst.The relatively mild reaction conditions are as follows: with poly-
500 mL toluene, the catalyst of 30 g are added in the autoclave of tetrafluoro liner, stirring is passed through oxygen after five minutes, this is anti-
It answers in kettle 5 minutes and is heated to assigned temperature.Reaction temperature is the reaction time 6 hours at 100 DEG C, and oxygen pressure is 3.0 MPa,
After centrifugal filtration, 10 uL samples is taken to analyze in 6890 gas-chromatography of Agilent, toluene conversion 55.8%, benzoic acid
Selectivity is up to 87.7%.
Embodiment 6
Take 6 mol zinc oxide, 3 mol magnesia, 3 mol aluminium oxide, the NH for separately taking 18 mol4The LiOH of OH and 18 mol, match
At the colloid aqueous solution of 18 L；Gained colloidal solution is put into large beaker and is stirred to react 24 hours, temperature is controlled at 100 DEG C,
It is continually fed into CO2, controlling its flow velocity is 60 mL/min, obtain required colloid, then be added into colloid 0.25 g copper nitrate,
0.25 g iron chloride, 0.13 g cerous nitrate and 0.17 g praseodymium chloride, the reaction was continued 6 hours, and temperature is controlled at 60 DEG C, then will
Resulting colloid vacuum rotary steam, 100 DEG C of obtained solid dry 18 hours；Resulting solid sample is placed in logical H2Tube furnace
Middle calcining 6 hours, temperature is controlled at 400 DEG C, obtains required catalyst.The relatively mild reaction conditions are as follows: with poly-
500 mL toluene, the catalyst of 20 g are added in the autoclave of tetrafluoro liner, stirring is passed through oxygen after five minutes, this is anti-
It answers in kettle 5 minutes and is heated to assigned temperature.Reaction temperature is the reaction time 8 hours at 100 DEG C, and oxygen pressure is 2.0 MPa,
After centrifugal filtration, 10 uL samples is taken to analyze in 6890 gas-chromatography of Agilent, toluene conversion 57.8%, benzoic acid
Selectivity is up to 93.7%.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the technical principles of the invention, several improvement and deformations can also be made, these improvement and deformations
Also it should be regarded as protection scope of the present invention.
Claims (5)
1. it is a kind of for toluene oxidation be benzoic acid novel nano catalyst, it is characterised in that: the catalyst is with metal composite
Oxide is carrier, using the transition metal of high activity as catalytic oxidation activity center, using rare earth metal as co-catalysis activated centre,
The transition metal element of the high activity is one or both of Mn, Cr, Cu, Co, Ni, Fe, and content accounts for the total matter of catalyst
The 0 ~ 3% of amount, the thulium are one or both of Sc, Y, La, Ce, Pr, Nd, and it is total that content accounts for catalyst
The 0 ~ 2% of quality；
The above-mentioned preparation method for the novel nano catalyst that toluene conversion is benzoic acid includes the following steps:
(1) the complex colloid aqueous solution for preparing bivalent metal oxide, aluminium oxide and lye, controls bivalent metal oxide and oxygen
Change the molar ratio of aluminium 2.0~6.0, controls the total concentration of lye in 2.0~15.0 mol/L, control the molal quantity of lye as gold
Belong to 1~3 times of oxide total mole number；
(2) gained colloidal solution is put into three-necked flask and is stirred to react 12~48 hours, control temperature at 60~150 DEG C, and
It is continually fed into CO2, controlling its flow velocity is 10~100 mL/min, obtains required colloid, then the mistake of high activity is added in colloid
Metal salt and rare earth metal salt are crossed, the reaction was continued 4~10 hours, and temperature is controlled at 25 ~ 100 DEG C, then subtracts resulting colloid
Pressure revolving, is placed in 80~120 DEG C of drying 6-24 hours for solid sample；
(3) resulting solid sample is placed in the tube furnace of logical reducing gas and is calcined 4~12 hours, control temperature 400~
750 DEG C, obtain required catalyst.
2. catalyst as described in claim 1, it is characterised in that bivalent metal oxide as described in step (1) can be
One or both of Ba, Ca, Mg, Zn；The lye can be LiOH, NaOH, KOH, NH4One or both of OH.
3. catalyst as described in claim 1, it is characterised in that transition metal salt described in step (2) can be Mn, Cr,
One or both of nitrate, chloride or acetate of Cu, Co, Ni, Fe.
4. catalyst as described in claim 1, it is characterised in that rare earth metal salt described in step (2) can be Sc, Y,
One or both of the nitrate of La, Ce, Pr, Nd, chloride.
5. catalyst as described in claim 1, it is characterised in that reducing gas described in step (3) can be H2, CO or
CH4One of.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110075882A (en) * | 2019-05-09 | 2019-08-02 | 南京工程学院 | A kind of application of transition metal composite oxide catalytic agent in catalysis toluene oxidation synthesizing benzoic acids benzyl ester |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105964266A (en) * | 2016-07-08 | 2016-09-28 | 南京工程学院 | Catalyst for synthesizing nonanal by high-selectivity catalytic oxidation of oleic acid |
| CN106492809A (en) * | 2016-11-18 | 2017-03-15 | 南京工程学院 | A kind of for removing new catalyst of formaldehyde and preparation method thereof |
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2018
- 2018-12-28 CN CN201811622034.9A patent/CN109621945A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105964266A (en) * | 2016-07-08 | 2016-09-28 | 南京工程学院 | Catalyst for synthesizing nonanal by high-selectivity catalytic oxidation of oleic acid |
| CN106492809A (en) * | 2016-11-18 | 2017-03-15 | 南京工程学院 | A kind of for removing new catalyst of formaldehyde and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110075882A (en) * | 2019-05-09 | 2019-08-02 | 南京工程学院 | A kind of application of transition metal composite oxide catalytic agent in catalysis toluene oxidation synthesizing benzoic acids benzyl ester |
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Application publication date: 20190416 |