CN107511157A - A kind of catalyst for preparing 2,6 dichlorobenzonitriles and its preparation method and application - Google Patents
A kind of catalyst for preparing 2,6 dichlorobenzonitriles and its preparation method and application Download PDFInfo
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- CN107511157A CN107511157A CN201610428298.5A CN201610428298A CN107511157A CN 107511157 A CN107511157 A CN 107511157A CN 201610428298 A CN201610428298 A CN 201610428298A CN 107511157 A CN107511157 A CN 107511157A
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- dichlorobenzonitriles
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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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
- B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/28—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing six-membered aromatic rings, e.g. styrene
Abstract
The present invention relates to a kind of catalyst for being used to prepare 2,6 dichlorobenzonitriles and its preparation method and application, catalyst is with silica gel or Al2O3For carrier, with V2O5、P2O5It is main active substances with the oxide containing Mo or salt, using at least one of Ni chloride and Cr oxide and Na, K or Cs chloride as auxiliary active agent, wherein V, Mo, P, Ni, Cr mol ratio are 1：0.1‑0.9：0.15‑0.9：0.004‑0.7：0.005 0.6, V and Na, K or Cs mol ratio are 1：0.003 0.2, prepared using infusion process.Compared with prior art.The catalyst of the present invention has that preparation technology is simple, cost is low and the advantages of long lifespan, in ammoxidation prepares 2,6 dichlorobenzonitriles, consumption ammonia is few, and feed stock conversion is higher, and the selectivity and yield of product are all higher, production cost can be further reduced, there is good application value.
Description
Technical field
The present invention relates to a kind of catalyst, more particularly, to a kind of catalyst for being used to prepare 2,6- dichlorobenzonitriles and its
Preparation method and application.
Background technology
2,6- dichlorobenzonitriles are a kind of preemergence herbicides of plant, and feature is to cut weeds that object is wide, and drug effect is high, and toxicity is very
It is low.It is among important herbicide and insecticide with 2, the 6- difluorobenzonitriles that 2,6- dichlorobenzonitriles are main material production
Body.In addition, 2,6- dichlorobenzonitriles are 2,6- difluoroanilines, careless cola, diflubenzuron, the important intermediate of flufenoxuron.
The primary raw material of 2,6- dichlorobenzonitriles or special engineering plastics polyphenylene oxide nitrile, the product have high-fire resistance,
Oil resistant, wear-resistant, decay resistance, it is molded good fluidity, the advantages that composite performance is good.With developing rapidly for these industries,
2,6- dichlorobenzonitrile market prospects are very optimistic.The synthetic method of 2,6- dichlorobenzonitriles is divided into organic synthesis method and vapor phase ammonia
Oxidizing process.Organic synthesis method be using 6- chlorine ortho-methylnitrobenzene as raw material, under catalyst action, carry out chlorination reaction, then with first
Acid, hydroxylamine hydrochloride carry out cyanation.Its reactions steps is grown, high energy consumption, and pollution is more serious, and industrialization difficulty is high.2,6- dichloros
Most simple, the most economical manufacture method of benzonitrile is that gas phase ammonoxidation reacts under catalyst action with 2,6- dichlorotoleune
Arrive, this method core technology is catalyst.
Ammoxidation of aromatic hydrocarbon technology starts from the fifties Japan Showa electrician, afterwards the seventies Mitsubishi gas and the U.S.
Badger companies have developed jointly fine grained fluid bed isophthalodinitrile device, have obtained ammoxidation of aromatic hydrocarbon technical merit larger
Development.In ammoxidation of aromatic hydrocarbon catalytic reaction technology, vanadium series catalyst is a kind of most universal and effective catalyst system and catalyzing.From near
Phase catalyst composition development from the point of view of, mainly by V-Sb, V-Cr and Sb-Fe tri- kinds form.V-Cr catalyst preparations are relatively easy,
It is reproducible, there is higher activity to ammoxidation of aromatic hydrocarbon.But the catalyst activity of two components is too high to easily cause deep oxidation, right
Ammonia has stronger capacity of decomposition, causes to generate substantial amounts of CO2、CO、H2O and HCN, make the substantial amounts of ammonia of reaction needs, add the three wastes
Treating capacity.With the appearance of ternary, quaternary and five yuan of catalyst, the selectivity of ammoxidation of aromatic hydrocarbon is greatly improved.
Up to the present the patent for preparing the catalyst of 2,6- dichlorobenzonitriles by ammonia oxidation both at home and abroad is less.Document
Catalyst is prepared for raw material using V, P in US4530797, by adding alkyl halide in reaction raw materials, by 2,6- dichloro-benzenes first
The molar yield of nitrile brings up to more than 85%；The European patent EP 0273317 of Japanese publication uses Fe, Sb to be prepared for raw material and is catalyzed
Agent, molar yield 81%；The fixed bed catalyst that the flat 3-44362 of Japan Patent JP are introduced, uses V, P, Mo, Cr as raw material,
γ-Al2O3 are carrier, and its highest molar yield is 85%.Chinese patent CN102909043B discloses one kind and is used to prepare 2,
The catalyst and synthetic method of 6- dichlorobenzonitriles and application, catalyst are prepared using silica as carrier using coprecipitation
Fluid catalyst using V-Cr-P-Co as main active component, carry out ammoxidation applied to 2,6-DCT and prepare 2,6-
In the technical process of dichlorobenzonitrile.
In the prior art, it is low and the problems such as cost is high to there is the poor activity, poor selectivity, conversion ratio of catalyst mostly,
The service life of catalyst is short.
The content of the invention
It is an object of the present invention to overcome the above-mentioned drawbacks of the prior art and provide a kind of selectivity is good, conversion
Rate is high, preparation technology is simple, cost is low and the catalyst for being used to prepare 2,6- dichlorobenzonitriles of long lifespan.
It is a further object to provide the application of the preparation method of the catalyst and the catalyst.
The purpose of the present invention can be achieved through the following technical solutions：
One kind is used for the catalyst for preparing 2,6- dichlorobenzonitriles, and described catalyst is with silica gel or Al2O3For carrier, with
V2O5、P2O5It is main active substances with the oxide containing Mo or salt, with Ni chloride and Cr oxide and Na, K or Cs
At least one chloride be auxiliary active agent, wherein V, Mo, P, Ni, Cr mol ratio be 1：0.1-0.9：0.15-0.9：
0.004-0.7：0.005-0.6, V and Na, K or Cs mol ratio are 1：0.003-0.2, the main active substances of the catalyst
The 2-25wt% of catalyst total amount is accounted for auxiliary active agent.
Described main active substances and the weight ratio of auxiliary active agent are 1：0.2-1.2.
Described silica gel is the spherical silica gel of 40-120 mesh.
Described Al2O3γ-the Al to be sieved using 80 mesh2O3。
It is preferred that the main active substances of the catalyst account for the 5-18wt% of catalyst total amount with auxiliary active agent.
The preparation method of described catalyst, using infusion process, specifically include following steps：
(1) oxide or salt that will form each component element of main active substances and auxiliary active agent add acid solution
In be uniformly dissolved；
(2) carrier is added in above-mentioned solution, submerges 0.5-8h, then after being aged, drying, activated in 753K-853K
6-7h, that is, obtain described catalyst.
Acid solution described in step (1) adds in distilled water obtained oxalic acid solution for oxalic acid.
Salt described in step (1) includes carbonate, nitrate, ammonium salt, phosphate, chloride, acetate or oxalates.
The ammoxidation that described catalyst is used for 2,6-DCT prepares 2,6- dichlorobenzonitriles, wherein 2,6- dichloromethanes
The mol ratio of benzene, ammonia and oxygen is 1：1.2-3：4-8, reaction temperature 623K-643K.
By adopting the above-described technical solution, beneficial effects of the present invention are：
1st, carrier is improved, catalyst performance improves.The spherical silica gel of 40-120 mesh is more beneficial for catalyst and mixed with reactant
Close, catalyst substantially rises with the reduction of reactor diameter, fluidization quality；Carrier uses γ-Al2O3At 140-150 DEG C
It is dehydrated under low temperature environment, γ-Al2O3It is not soluble in water, strong acid or strong base solution are dissolved in, its internal surface area is up to hundreds of square metres,
Active high absorption capacity is strong.Reuse can also be regenerated by heating 6-8h below 175 DEG C after industrial use, and reusing reduces
Production cost；
2nd, raw material sources are more extensive, reduce cost.The raw material for synthesizing each active material used in catalyst of the present invention is oxygen
Compound, or inorganic salts or organic salt of element etc., inorganic salts have carbonate, nitrate, ammonium salt, phosphate and chloride
Deng；Organic salt has acetate, oxalates etc..Cost of material is reduced using carbonate, chloride etc.；
3rd, preparation technology is simple.Preparation method is not granulated using spray dryer, using infusion process, it is only necessary to is passed through
Catalyst can be prepared by crossing once roasting；
4th, high income.Using catalyst provided by the present invention and corresponding method for ammoxidation, consumption ammonia is few, feed stock conversion
Higher, the selectivity and yield of product are all higher, can further reduce production cost, have good application value.
Embodiment
With reference to specific embodiment, the present invention is described in detail.
Embodiment 1
(1) catalyst preparation
First by 2.5g V2O5And 0.85gCrO3It is added to together in the 250ml distilled water containing 20g oxalic acid, it is left in 343K
Right heating for dissolving, navy blue solution is made.Then 0.15g KCl, 1.95g P is added into the solution again2O5, 1.05g's
(NH4)6Mo7O24·4H2O, 2.10g NiCl2·6H2The materials such as O, stir, the clear solution of active material is made.By drying
The spherical silica gel 100g of 120 mesh is added in above-mentioned solution, is stirred, and after 373K drying, 6 hours are activated i.e. then at 813K
Obtain required catalyst.
(2) ammoxidation of 2,6- dichlorotoleune
In the steel pipe that internal diameter is 38mm, the catalyst 90g as made from this example methods described is added, 623K is warming up to, presses
2,6- dichlorotoleune：Ammonia：Oxygen (being converted by air)=1：2.5：Reactant mixture is sent into reactor by the amount ratio of 5 material, and 2,
The conversion ratio of 6- dichlorotoleune is 99.6%, the molar yield 92.5% of 2,6- dichlorobenzonitriles.
Embodiment 2
(1) catalyst preparation
By 2.80g V2O5With 0.85g CrO3It is added to together in the 250ml distilled water containing 20g oxalic acid, in 343K
Left and right dissolves by heating, and navy blue solution is made, then adds 0.16gNaCl, 1.80g P into the solution again2O5, 1.00g
(NH4)6Mo7O24·4H2O, 2.10g NiCl2·6H2O, it is uniformly dissolved, transparent solution is made.80 purposes of drying are spherical
Silica gel 100g is added in clear solution (with embodiment 1), is stirred, 373K drying, then is after being activated 6 hours under 813K
Obtain required catalyst.
(2) ammoxidation of 2,6- dichlorotoleune
The catalyst 90g as made from this example methods described is added in the reactor described in embodiment 1, maintains catalyst bed
Layer temperature is in 643K, by 2,6-DCT：Ammonia：Oxygen (being converted by air)=1：3：The amount ratio of 8 material is by reactant mixture
Reactor is sent into, the conversion ratio of meta-xylene is 98.9%, the molar yield 91.5% of 2,6- dichlorobenzonitriles.
Embodiment 3
(1) catalyst preparation
By 2.80g V2O5With 1.06g CrO3It is added to together in the 250ml distilled water containing 20g oxalic acid, in 343K
Left and right dissolves by heating, and navy blue solution is made, then adds 0.19gNaCl, 1.80g P into the solution again2O5, 0.85g
(NH4)6Mo7O24·4H2O, 2.46g NiCl2·6H2O, it is uniformly dissolved, transparent solution is made.40 purposes of drying are spherical
Silica gel 100g is added in clear solution (with embodiment 1), is stirred, 373K drying, then is after being activated 6 hours under 813K
Obtain required catalyst.
(2) ammoxidation of 2,6- dichlorotoleune
The catalyst 90g as made from this example methods described is added in the reactor described in embodiment 1, maintains catalyst bed
Layer temperature is in 643K, by 2,6-DCT：Ammonia：Oxygen (being converted by air)=1：1.2：The amount ratio of 4 material, which will react, to be mixed
Thing is sent into reactor, and the conversion ratio of meta-xylene is 98.7%, the molar yield 88.6% of 2,6- dichlorobenzonitriles.
Embodiment 4
(1) catalyst preparation
The NaCl in example 2 is replaced with 0.15g CsCl, the preparation method of catalyst is the same as example 2.
(2) ammoxidation of 2,6- dichlorotoleune
The catalyst 90g as made from this example methods described is added in the reactor described in embodiment 1, maintains catalyst bed
Layer temperature is in 643K, by 2,6-DCT：Ammonia：Oxygen (being converted by air)=1：3：The amount ratio of 5 material is by reactant mixture
Reactor is sent into, the conversion ratio of meta-xylene is 99.2%, the molar yield 92.1% of 2,6- dichlorobenzonitriles.
Embodiment 5
(1) catalyst preparation
Catalyst carrier is used instead as γ-Al2O3, remaining prepares catalyst as described in Example 1 with embodiment 1.γ-
Al2O3Be aluminium hydroxide be dehydrated under 140-150 DEG C of low temperature environment be made, Al2O3Sieved using 80 mesh, at 175 DEG C after use
Heating 6-8h can also regenerate reuse below.
(2) ammoxidation of 2,6- dichlorotoleune
Added in the reactor described in embodiment 1 and carry out ammoxidation reaction, 2,6- dichloros by the reaction condition of embodiment 1
The conversion ratio of toluene is 97.9%, the molar yield 88.1% of 2,6- dichlorobenzonitriles.
Embodiment 6
(1) catalyst preparation
Catalyst carrier is used instead as γ-Al2O3, γ-Al2O3It is that aluminium hydroxide is dehydrated under 140-150 DEG C of low temperature environment
It is made, Al2O3Sieved using 80 mesh, reuse can also be regenerated by heating 6-8h below 175 DEG C after use.Remaining same embodiment
2, and catalyst is prepared as described in Example 2.
(2) ammoxidation of 2,6- dichlorotoleune
Added in the reactor described in embodiment 1 and carry out ammoxidation reaction, 2,6- dichloros by the reaction condition of embodiment 2
The conversion ratio of toluene is 96.8%, the molar yield 86.8% of 2,6- dichlorobenzonitriles.
Embodiment 7
One kind is used for the catalyst for preparing 2,6- dichlorobenzonitriles, using the spherical silica gel of 40 mesh as carrier, with V2O5、P2O5
And MoO3For main active substances, with NiCl, CrO3With the mol ratio that NaCl is auxiliary active agent, wherein V, Mo, P, Ni, Cr
For 1：0.1：0.15：0.004：0.005, V and Na mol ratio is 1：0.003, main active substances account for auxiliary active agent
The 5-18wt% of catalyst total amount.
The preparation method of catalyst, using infusion process, specifically include following steps：
(1) oxide or the salt addition oxalic acid that will form each component element of main active substances and auxiliary active agent are molten
It is uniformly dissolved in liquid；
(2) carrier is added in above-mentioned solution, submerges 0.5h, then after being aged, drying, activated 6h in 753K, produce
To described catalyst.
The ammoxidation that the catalyst is used for 2,6- dichlorotoleune prepares 2,6- dichlorobenzonitriles.
Embodiment 8
One kind is used for the catalyst for preparing 2,6- dichlorobenzonitriles, using the spherical silica gel of 120 mesh as carrier, with V2O5、P2O5
(NH4)6Mo7O24·4H2O is main active substances, with NiCl, CrO3Be auxiliary active agent with KCl, wherein V, Mo, P,
Ni, Cr mol ratio are 1：0.9：0.9：0.7：0.6, V and K mol ratio is 1：0.2, main active substances and auxiliary activity thing
Matter accounts for the 18wt% of catalyst total amount.
The preparation method of catalyst, using infusion process, specifically include following steps：
(1) oxide or the salt addition oxalic acid that will form each component element of main active substances and auxiliary active agent are molten
It is uniformly dissolved in liquid；
(2) carrier is added in above-mentioned solution, submerges 8h, then after being aged, drying, activated 7h in 853K, that is, obtain
Described catalyst.
The ammoxidation that the catalyst is used for 2,6- dichlorotoleune prepares 2,6- dichlorobenzonitriles.
Embodiment 9
One kind is used for the catalyst for preparing 2,6- dichlorobenzonitriles, the γ-Al to be sieved with 80 mesh2O3For carrier, with V2O5、
P2O5、MoO3For main active substances, with NiCl, CrO3And NaCl and KCl mixtures are auxiliary active agent, wherein V, Mo, P,
Ni, Cr mol ratio are 1：0.8：0.7：0.1：0.1, V with Na, K mol ratio is 1：0.1, main active substances are lived with auxiliary
Property material accounts for the 10wt% of catalyst total amount.
The preparation method of catalyst, using infusion process, specifically include following steps：
(1) oxide or the salt addition oxalic acid that will form each component element of main active substances and auxiliary active agent are molten
It is uniformly dissolved in liquid；
(2) carrier is added in above-mentioned solution, submerges 6h, then after being aged, drying, activated 6.5h in 800K, produce
To described catalyst.
The ammoxidation that the catalyst is used for 2,6- dichlorotoleune prepares 2,6- dichlorobenzonitriles
Using catalyst provided by the present invention and corresponding method for ammoxidation, ammonia is than small, and feed stock conversion is high, product
Selectivity and yield are all higher, can further reduce production cost.
It should be understood by those skilled in the art that the present invention is not limited to the above embodiments, above-described embodiment and explanation
Merely illustrating the principles of the invention described in book, it is of the invention without departing from the spirit and scope of the present invention also to have respectively
Kind changes and improvements, these changes and improvements all fall within the protetion scope of the claimed invention.
Claims (8)
1. one kind is used for the catalyst for preparing 2,6- dichlorobenzonitriles, it is characterised in that described catalyst is with silica gel or Al2O3
For carrier, with V2O5、P2O5Be main active substances with the oxide containing Mo or salt, with Ni chloride and Cr oxide and
At least one of Na, K or Cs chloride are auxiliary active agent, and wherein V, Mo, P, Ni, Cr mol ratio are 1：0.1-0.9：
0.15-0.9：0.004-0.7：0.005-0.6, V and Na, K or Cs mol ratio are 1：0.003-0.2, the master of the catalyst
Active material is wanted to account for the 2-25wt% of catalyst total amount with auxiliary active agent.
2. catalyst according to claim 1, it is characterised in that described main active substances and auxiliary active agent
Weight ratio is 1：0.2-1.2.
3. catalyst according to claim 1, it is characterised in that described silica gel is the spherical silica gel of 40-120 mesh.
4. catalyst according to claim 1, it is characterised in that described Al2O3γ-the Al to be sieved using 80 mesh2O3。
5. catalyst according to claim 1, it is characterised in that the main active substances of the preferable catalyst with it is auxiliary
Active material is helped to account for the 5-18wt% of catalyst total amount.
A kind of 6. preparation method of catalyst as claimed in claim 1, it is characterised in that using infusion process, specifically include with
Lower step：
(1) will form molten in the oxide or salt addition acid solution of each component element of main active substances and auxiliary active agent
Solution is uniform；
(2) carrier is added in above-mentioned solution, submerges 0.5-8h, then after being aged, drying, 6-7h is activated in 753K-853K,
Obtain described catalyst.
7. the preparation method of catalyst according to claim 6, it is characterised in that the acid solution described in step (1) is grass
Acid adds in distilled water obtained oxalic acid solution.
8. the application of catalyst as claimed in claim 1, it is characterised in that described catalyst is used for 2,6-DCT
Ammoxidation prepares 2,6- dichlorobenzonitriles, and the wherein mol ratio of 2,6-DCT, ammonia and oxygen is 1：1.2-3：4-8, reaction temperature
Spend for 623K-643K.
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Cited By (4)
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| CN108774156A (en) * | 2018-08-23 | 2018-11-09 | 常州新日催化剂有限公司 | A method of preparing 2,6- dichlorobenzonitriles |
| CN115646520A (en) * | 2022-11-15 | 2023-01-31 | 江苏新河农用化工有限公司 | Catalyst for synthesizing parachlorobenzonitrile and preparation method and application thereof |
| CN116854611A (en) * | 2023-07-06 | 2023-10-10 | 湖北纽苏莱新材料有限公司 | Method for preparing 2, 6-dichlorobenzonitrile by gas phase ammoxidation method |
| CN115646520B (en) * | 2022-11-15 | 2024-05-14 | 江苏新河农用化工有限公司 | Catalyst for synthesizing p-chlorobenzonitrile and preparation method and application thereof |
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