CN106334564A - Catalyst for preparing 3-cyanopyridine and preparation method of catalyst - Google Patents

Catalyst for preparing 3-cyanopyridine and preparation method of catalyst Download PDF

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CN106334564A
CN106334564A CN201610733061.8A CN201610733061A CN106334564A CN 106334564 A CN106334564 A CN 106334564A CN 201610733061 A CN201610733061 A CN 201610733061A CN 106334564 A CN106334564 A CN 106334564A
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catalyst
active component
preparing
tricyano
carrier
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徐大鹏
荣庆洪
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Gunther Bio Tech Ltd Shandong
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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
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/888—Tungsten
    • B01J23/8885—Tungsten containing also molybdenum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/30—Constitutive chemical elements of heterogeneous catalysts of Group III (IIIA or IIIB) of the Periodic Table
    • B01J2523/31—Aluminium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/40—Constitutive chemical elements of heterogeneous catalysts of Group IV (IVA or IVB) of the Periodic Table
    • B01J2523/47—Titanium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/40—Constitutive chemical elements of heterogeneous catalysts of Group IV (IVA or IVB) of the Periodic Table
    • B01J2523/48—Zirconium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/50—Constitutive chemical elements of heterogeneous catalysts of Group V (VA or VB) of the Periodic Table
    • B01J2523/54—Bismuth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
    • B01J2523/67—Chromium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
    • B01J2523/68—Molybdenum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
    • B01J2523/69—Tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/84—Metals of the iron group
    • B01J2523/842—Iron
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/84—Metals of the iron group
    • B01J2523/845—Cobalt
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/84—Metals of the iron group
    • B01J2523/847—Nickel

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)

Abstract

The invention relates to a catalyst for preparing 3-cyanopyridine and a preparation method of the catalyst. The catalyst comprises a carrier, a main active component and an auxiliary active component. The carrier is Al2O3 powder, the main active component is a combination of Cr2O5 and modified V2O5, and the auxiliary active component is a combination of at least three of oxides of Ti, Zr, Mo, Bi, Ni and Fe. The preparation method includes the steps of mixing the carrier, the main active component and the auxiliary active component, adding the mixture to deionized water to be stirred to form a turbid solution, conducting ultrasonic vibrating on the turbid solution, conducting heating and drying to obtain solid powder, and calcinating the solid powder at high temperature. The catalyst and the method has the advantages that by means of the catalyst and the corresponding ammoxidation method, the product yield and selectivity are high, the conversion rate of raw materials is high and can reach 99%, and the purity of produced 3-cyanopyridine reaches 99.5% or above. The service life can reach 3-5 years, production cost is greatly reduced, and the technology has good application value.

Description

A kind of catalyst for preparing tricyano pyridine and preparation method thereof
Technical field
The present invention relates to a kind of catalyst for preparing tricyano pyridine and preparation method thereof.
Background technology
The main method of industrialized production nicotinonitrile is with 3- picoline as raw material at present, in nh3、o2And catalysis The lower ammoxidation reaction that passes through of agent effect is prepared, i.e. 3- picoline ammonia oxidation.Ammoxidation reaction refers to alkene, aromatic hydrocarbons, alkane Hydrocarbons and their derivates and air (o2)、nh3The class reaction obtaining cyanides is reacted in mixing on a catalyst, and reaction is logical Formula: r-ch3+nh3+ o2=r-cn+h2o
The possible reaction mechanism mechanism of reaction of this reaction is: the dehydrogenation under catalyst action of r-ch3 first generates r-ch2 free radical, should be certainly R-cho is formed by base oxygen uptake, subsequent r-cho and nh3 condensation forms nitrile, or r-cho is first oxidized to form r-cooh, so Act on generation acid amides afterwards with nh3 and hydrolyze to form nitrile again.
Ammoxidation reaction process is a complicated process, and in addition to main reaction, side reaction is more, and its difficult point is catalyst In preparation.The catalyst of ammoxidation reaction does not require nothing more than high conversion rate, and it selectively also will height.3- picoline ammoxidation The possible reaction mechanism of nicotinonitrile processed: 3- picoline multistep dehydrogenation and oxidation after Catalyst Adsorption, generate formaldehyde pyrrole Pyridine or pyridinecarboxylic acid, then carry out cyanogenation and generate product.Domestic at present each large enterprises are made when preparing nicotinonitrile Catalyst Conversion is low, and usual conversion ratio is 90% about, and life-span is usually used the time of 1 year about, and accessory substance More it is impossible to overcome high energy consumption issues during ammoxidation reaction.
Content of the invention
The present invention is adopted the technical scheme that to solve above-mentioned technical problem:
A kind of catalyst for preparing tricyano pyridine, including carrier, main active component and Supplementary active compounds, wherein:
Described carrier adopts the al that granularity is 50-180 mesh2o3Powder；
Described main active component is cr2o5With modified v2o5A combination of both；
Described Supplementary active compounds are at least three or more the combination in the oxide of ti, zr, mo, bi, ni, fe；
The quality of described carrier accounts for the 20-70% of total catalyst quality, and described main active component accounts for the 20- of total catalyst quality 50%, described Supplementary active compounds account for the 1-30% of total catalyst quality；
Described modification v2o5Method of modifying be by v2o5It is dissolved in arriving in the ethanol that concentration is 30% and the mixed solution of hydrogen peroxide The volume ratio of turbid solution, wherein ethanol and hydrogen peroxide is 1:1, adds low-carbon (LC) aldehyde to be stirred, finally by muddiness in turbid solution Liquid heating, drying, obtains modified v2o5Powder.
As a preferred technical solution of the present invention, described carrier, described main active component, described Supplementary active compounds The mass ratio of three is 6.9:2.1:1.
As another kind of optimal technical scheme of the present invention, cr in described main active component2o5With modified v2o5Mass ratio For 1:1-1:5.
Further, described low-carbon (LC) aldehyde is that one or more of formaldehyde, acetaldehyde, propionic aldehyde combine, and described low-carbon (LC) aldehyde Addition is not less than the 18% of the mixed liquor volume of described ethanol and hydrogen peroxide.
Present invention also offers a kind of preparation method of the catalyst for preparing tricyano pyridine, the steps include: by weight Amount ratio weighs carrier, main active component and Supplementary active compounds, is added to stirring in deionized water and is formed after three is mixed Turbid solution, carries out ultrasonic oscillation 1-2 hour to this turbid solution, is then heated to 90-150 DEG C of evaporation drying and obtains solid powder End, by pressed powder under the conditions of 300-700 DEG C roasting 36-48 hour, obtain final product a kind of catalysis for preparing tricyano pyridine Agent.
To sum up, the invention has the beneficial effects as follows:
Using catalyst provided by the present invention and corresponding method for ammoxidation, product yield and select all higher, the turning of raw material Rate is higher, and up to 99%, the tricyano pyridine purity produced reaches more than 99.5%.Service life can reach 3-5, significantly Reduce production cost, so this technology has preferable using value.
Specific embodiment
For a better understanding of the present invention, it is further elucidated with the technology contents of the present invention with reference to embodiment.
Embodiment 1
A kind of catalyst for preparing tricyano pyridine, including carrier, main active component and Supplementary active compounds, wherein:
Described carrier adopts the al that granularity is 50-180 mesh2o3Powder；
Described main active component is cr2o5With modified v2o5A combination of both；
Described Supplementary active compounds are the oxide of ti, zr, mo；
The quality of described carrier accounts for the 70% of total catalyst quality, and described main active component accounts for the 20% of total catalyst quality, described Supplementary active compounds account for the 10% of total catalyst quality；
Described modification v2o5Method of modifying be by v2o5It is dissolved in arriving in the ethanol that concentration is 30% and the mixed solution of hydrogen peroxide The volume ratio of turbid solution, wherein ethanol and hydrogen peroxide is 1:1, adds be not less than the mixed of described ethanol and hydrogen peroxide in turbid solution Close 18% formaldehyde of liquor capacity and acetaldehyde is stirred, finally by turbid solution heating, drying, obtain modified v2o5Powder.
Further, cr in described main active component2o5With modified v2o5Mass ratio be 1:1.
The step of the preparation method of above-mentioned catalyst is: weighs carrier, main active component and auxiliary activity by weight proportion Component, is added to stirring in deionized water and forms turbid solution, carry out ultrasonic oscillation 1-2 to this turbid solution little after three is mixed When, be then heated to 90-150 DEG C evaporation drying obtain pressed powder, by pressed powder under the conditions of 300-700 DEG C roasting 36- 48 hours, obtain final product a kind of catalyst for preparing tricyano pyridine.
Embodiment 2
A kind of catalyst for preparing tricyano pyridine, including carrier, main active component and Supplementary active compounds, wherein:
Described carrier adopts the al that granularity is 50-180 mesh2o3Powder；
Described main active component is cr2o5With modified v2o5A combination of both；
Described Supplementary active compounds are the oxide of zr, mo, ni, fe；
The quality of described carrier accounts for the 69% of total catalyst quality, and described main active component accounts for the 21% of total catalyst quality, described Supplementary active compounds account for the 10% of total catalyst quality；
Described modification v2o5Method of modifying be by v2o5It is dissolved in arriving in the ethanol that concentration is 30% and the mixed solution of hydrogen peroxide The volume ratio of turbid solution, wherein ethanol and hydrogen peroxide is 1:1, adds be not less than the mixed of described ethanol and hydrogen peroxide in turbid solution The propionic aldehyde of the 18% of conjunction liquor capacity is stirred, and finally by turbid solution heating, drying, obtains modified v2o5Powder, its preparation method Consistent with embodiment 1.
Embodiment 3
A kind of catalyst for preparing tricyano pyridine, including carrier, main active component and Supplementary active compounds, wherein:
Described carrier adopts the al that granularity is 50-180 mesh2o3Powder；
Described main active component is cr2o5With modified v2o5A combination of both；
Described Supplementary active compounds are the oxide of ti, mo, bi, fe；
The quality of described carrier accounts for the 50% of total catalyst quality, and described main active component accounts for the 35% of total catalyst quality, described Supplementary active compounds account for the 15% of total catalyst quality；
Described modification v2o5Method of modifying be by v2o5It is dissolved in arriving in the ethanol that concentration is 30% and the mixed solution of hydrogen peroxide The volume ratio of turbid solution, wherein ethanol and hydrogen peroxide is 1:1, adds be not less than the mixed of described ethanol and hydrogen peroxide in turbid solution The formaldehyde of the 18% of conjunction liquor capacity is stirred, and finally by turbid solution heating, drying, obtains modified v2o5Powder, its preparation method Consistent with embodiment 1.
Embodiment 4
A kind of catalyst for preparing tricyano pyridine, including carrier, main active component and Supplementary active compounds, wherein:
Described carrier adopts the al that granularity is 50-180 mesh2o3Powder；
Described main active component is cr2o5With modified v2o5A combination of both；
Described Supplementary active compounds are the oxide of ti, zr, mo, bi, ni, fe；
The quality of described carrier accounts for the 20% of total catalyst quality, and described main active component accounts for the 50% of total catalyst quality, described Supplementary active compounds account for the 30% of total catalyst quality；
Described modification v2o5Method of modifying be by v2o5It is dissolved in arriving in the ethanol that concentration is 30% and the mixed solution of hydrogen peroxide The volume ratio of turbid solution, wherein ethanol and hydrogen peroxide is 1:1, adds be not less than the mixed of described ethanol and hydrogen peroxide in turbid solution 18% formaldehyde, acetaldehyde and the propionic aldehyde that close liquor capacity are stirred, and finally by turbid solution heating, drying, obtain modified v2o5Powder End, its preparation method is consistent with embodiment 1.
Following table is the contrast form of reactivity in producing reaction for embodiment 1-4
Embodiment Feed stock conversion (%) Product purity (%)
1 97.7 98.9
2 99.5 99.6

Claims (5)

1. a kind of catalyst for preparing tricyano pyridine, including carrier, main active component and Supplementary active compounds, its feature It is,
Described carrier adopts the al that granularity is 50-180 mesh2o3Powder；
Described main active component is cr2o5With modified v2o5A combination of both；
Described Supplementary active compounds are at least three or more the combination in the oxide of ti, zr, mo, bi, ni, fe；
The quality of described carrier accounts for the 20-70% of total catalyst quality, and described main active component accounts for the 20- of total catalyst quality 50%, described Supplementary active compounds account for the 1-30% of total catalyst quality；
Described modification v2o5Method of modifying be by v2o5Be dissolved in the ethanol that concentration is 30% and the mixed solution of hydrogen peroxide to muddy The volume ratio of turbid liquid, wherein ethanol and hydrogen peroxide is 1:1, adds low-carbon (LC) aldehyde to be stirred, finally by turbid solution in turbid solution Heating, drying, obtains modified v2o5Powder.
2. a kind of catalyst for preparing tricyano pyridine according to claim 1 it is characterised in that described carrier, Described main active component, the mass ratio of described Supplementary active compounds three are 6.9:2.1:1.
3. a kind of catalyst for preparing tricyano pyridine according to claim 1 is it is characterised in that described main activity Cr in component2o5With modified v2o5Mass ratio be 1:1-1:5.
4. a kind of catalyst for preparing tricyano pyridine it is characterised in that described low-carbon (LC) aldehyde be formaldehyde, acetaldehyde, in propionic aldehyde One or more combination, and the addition of described low-carbon (LC) aldehyde is not less than the mixed liquor volume of described ethanol and hydrogen peroxide 18%.
5. a kind of preparation method of the catalyst for preparing tricyano pyridine is it is characterised in that the steps include: by weight proportion Weigh carrier, main active component and Supplementary active compounds, be added to stirring in deionized water after three is mixed and form turbid solution, This turbid solution is carried out with ultrasonic oscillation 1-2 hour, is then heated to 90-150 DEG C of evaporation drying and obtains pressed powder, by solid Powder roasting 36-48 hour under the conditions of 300-700 DEG C, obtains final product a kind of catalyst for preparing tricyano pyridine.
CN201610733061.8A 2016-08-27 2016-08-27 Catalyst for preparing 3-cyanopyridine and preparation method of catalyst Pending CN106334564A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108993587A (en) * 2018-09-07 2018-12-14 安徽瑞邦生物科技有限公司 Prepare effective catalyst system required for nicotinonitrile
CN114790167A (en) * 2022-04-25 2022-07-26 北京弗莱明科技有限公司 Preparation method of 2, 3-dichloropyridine

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1424144A (en) * 2002-12-31 2003-06-18 武汉大学 Catalyst for preparing 3-cyanopyridine and preparation and use thereof
CN101433836A (en) * 2008-12-05 2009-05-20 浙江师范大学 Catalyst for producing 3-cyano pyridine as well as preparation method and use thereof
CN105233849A (en) * 2015-09-20 2016-01-13 潜江市富阳化工有限公司 Composite catalyst used for synthesis of 3-cyanopyridine, and preparation method and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1424144A (en) * 2002-12-31 2003-06-18 武汉大学 Catalyst for preparing 3-cyanopyridine and preparation and use thereof
CN101433836A (en) * 2008-12-05 2009-05-20 浙江师范大学 Catalyst for producing 3-cyano pyridine as well as preparation method and use thereof
CN105233849A (en) * 2015-09-20 2016-01-13 潜江市富阳化工有限公司 Composite catalyst used for synthesis of 3-cyanopyridine, and preparation method and application thereof

Non-Patent Citations (1)

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徐滨士: "《纳米表面工程》", 31 January 2004, 化学工业出版社 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108993587A (en) * 2018-09-07 2018-12-14 安徽瑞邦生物科技有限公司 Prepare effective catalyst system required for nicotinonitrile
CN114790167A (en) * 2022-04-25 2022-07-26 北京弗莱明科技有限公司 Preparation method of 2, 3-dichloropyridine
CN114790167B (en) * 2022-04-25 2024-01-05 北京弗莱明科技有限公司 Preparation method of 2, 3-dichloropyridine

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