CN108658847A - A kind of iron content pyridine chloride salt ions liquid and its preparation method and application - Google Patents
A kind of iron content pyridine chloride salt ions liquid and its preparation method and application Download PDFInfo
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- CN108658847A CN108658847A CN201810425376.5A CN201810425376A CN108658847A CN 108658847 A CN108658847 A CN 108658847A CN 201810425376 A CN201810425376 A CN 201810425376A CN 108658847 A CN108658847 A CN 108658847A
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- iron content
- chloride salt
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- pyridine
- ions liquid
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- QJHUOVRGUGFXDS-UHFFFAOYSA-N CCC1N(CC)CC=CC1 Chemical compound CCC1N(CC)CC=CC1 QJHUOVRGUGFXDS-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
Abstract
A kind of iron content pyridine chloride salt ions liquid and its preparation method and application, belongs to the field of chemical synthesis.A kind of iron content pyridine chloride salt ions liquid can be used as preparing the catalyst of 2 chlorine, 6 trichloromethyl pyridine, to improve the product yield of 2 chlorine, 6 trichloromethyl pyridine and reduce its chlorination reaction temperature.A kind of preparation method of iron content pyridine chloride salt ions liquid, this preparation method is easy, being capable of efficient preparation iron content pyridine chloride salt ions liquid.In addition the application the invention further relates to iron content pyridine chloride salt ions liquid in the catalyst for preparing 2 chlorine, 6 trichloromethyl pyridine.
Description
Technical field
The present invention relates to the field of chemical synthesis, and more particularly to a kind of iron content pyridine chloride salt ions liquid and preparation method thereof
And application.
Background technology
N-serve is a kind of important nitrification inhibitor, can efficiently inhibit to nitrify in soil thin
The activity of bacterium, to alleviate the reaction speed that soil ammonium-state is converted into nitrate nitrogen.Ammonium nitrogen can by soil colloid adsorb and
It not easily runs off, to improve the utilization ratio of fertilizer.But under the conditions of Soil ventilation, ammonium nitrogen can under microbial action
To be converted into nitrate nitrogen, but nitrate nitrogen has been lost in, and the utilization rate of nitrogenous fertilizer is caused to decline.Therefore, N-serve is made
There is very important practical value in agricultural production for nitrification inhibitor use.
Traditional catalyst prepare N-serve method that there are reaction temperatures is excessively high, product yield is low and
Catalyst inactivation is not easy the shortcomings of regenerating.
Invention content
The first object of the present invention is to provide a kind of iron content pyridine chloride salt ions liquid, this iron content pyridine chloride salt ions liquid
Body is the important source material for the catalyst for preparing N-serve.
The second object of the present invention is to provide a kind of preparation method of N-serve, this preparation method
It is easy.
The third object of the present invention is to provide a kind of application of iron content pyridine chloride salt ions liquid.
The present invention solves its technical problem using following technical scheme to realize.
The present invention proposes a kind of iron content pyridine chloride salt ions liquid, and the general structure of iron content pyridine chloride salt ions liquid is such as
Under：
Wherein R1And R2It is alkyl.
The present invention also proposes a kind of preparation method of iron content pyridine chloride salt ions liquid comprising by single pyridine villaumite and
Ferric chloride hexahydrate synthesizes iron content pyridine chloride salt ions liquid.
The present invention also proposes iron content pyridine chloride salt ions liquid in the catalyst for preparing N-serve
Using.
The advantageous effect of the embodiment of the present invention is：
A kind of iron content pyridine chloride salt ions liquid provided by the invention, iron content pyridine chloride salt ions liquid can be used as and prepare
The main component of the catalyst of N-serve, iron content pyridine chloride salt ions liquid can be improved as catalyst
It prepares the product yield of N-serve and reduces its chlorination reaction temperature, and iron content pyridine chloride salt ions liquid
A kind of long catalytic life and renewable free of contamination green catalyst can be used as.
A kind of preparation method of iron content pyridine chloride salt ions liquid provided by the invention, this preparation method is easy, Neng Gougao
The preparation iron content pyridine chloride salt ions liquid of efficiency.
The present invention provides iron content pyridine chloride salt ions liquid answering in the catalyst for preparing N-serve
With.
Specific implementation mode
It in order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below will be in the embodiment of the present invention
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, builds according to normal condition or manufacturer
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
Have below to a kind of iron content pyridine chloride salt ions liquid of the embodiment of the present invention and its preparation method and application
Body explanation.
A kind of iron content pyridine chloride salt ions liquid, the structure of iron content pyridine chloride salt ions liquid are provided in the embodiment of the present invention
General formula is as follows：
Wherein R1And R2It is alkyl.
Further, in a preferred embodiment of the present invention, R1For CnH2n+1(n=1~4), R2For CnH2n+1(n=1~18),
Preferably, R1For methyl (- CH3) or ethyl (- CH2CH3), R2For methyl (- CH3), ethyl (- CH2CH3) or propyl (-
CH2CH2CH3)。
A kind of preparation method of iron content pyridine chloride salt ions liquid is also provided in the embodiment of the present invention comprising first pass through 6-
Substituted pyridines and the single pyridine villaumite of chlorine alkane substitute synthesis, then contained by single pyridine villaumite and the ferric chloride hexahydrate synthesis of synthesis
Iron pyridine chloride salt ions liquid.
Further, in a preferred embodiment of the present invention, the step of preparing single pyridine villaumite is included in inert gas shielding
Under, 6- substituted pyridines and chlorine alkane substitute are added in three-necked flask and are mixed, 6- substituted pyridines and chlorine alkane substitute
Molar ratio is 1：(1~1.3) is warming up to 40~100 DEG C of 10~60h of reaction, it is mixed that the solid-liquid precipitated containing light yellow crystal is made
Object is closed, single pyridine villaumite is obtained after being then filtered, washed and dried, the method can prepare synthesis iron content pyridine chloride salt ions liquid
The raw material list pyridine villaumite of body, reaction equation are as follows：
Further, in a preferred embodiment of the present invention, inert gas generally select cheap and easily-available nitrogen, helium or
Argon gas.
Further, in a preferred embodiment of the present invention, the step of preparing iron content pyridine chloride salt ions liquid includes will be single
Pyridine villaumite and ferric chloride hexahydrate, which are added in three-necked flask, to be mixed, mole of single pyridine villaumite and ferric chloride hexahydrate
Than being 1：(0.9~1.1) is warming up to 100~150 DEG C of 0.5~12h of reaction, the iron content pyridine chloride salt ions of clear yellow viscous is made
Liquid, the reaction efficiency that the method prepares iron content pyridine chloride salt ions liquid is high, standby iron content pyridine chloride salt ions liquid obtained
Stable structure, reaction equation are as follows：
Iron content pyridine chloride salt ions liquid is also provided in the embodiment of the present invention and is preparing urging for N-serve
Application in agent will obtain molecular sieve carried iron content after obtained iron content pyridine chloride salt ions liquid and molecular sieve mixed processing
Pyridine chloride salt ions liquid catalyst is catalyzed 2- first using obtained molecular sieve carried iron content pyridine chloride salt ions liquid catalyst
N-serve is obtained by the reaction in yl pyridines and nitrogen.
Further, in a preferred embodiment of the present invention, iron content pyridine chloride salt ions liquid, molecular sieve and the nothing that will be obtained
Water-ethanol is mixed, and is ultrasonically treated, is dried to obtain the catalyst for preparing N-serve.
Further, in a preferred embodiment of the present invention, after the catalyst of N-serve being made, by gas
2- picolines aqueous solution, chlorine and inert gas after change are passed through the catalyst for being placed with N-serve
In reactor, collects condensed product and N-serve is made.
The feature and performance of the present invention are described in further detail with reference to embodiments.
Embodiment 1
The present embodiment provides a kind of preparation methods of iron content pyridine chloride salt ions liquid, include the following steps：
A. single pyridine villaumite is prepared
Under nitrogen protection, 6 methyl-substituted pyridines and monochloro methane are added in three-necked flask and are mixed, 6 first
The molar ratio of base-substituted pyridines and monochloro methane is 1：1,80 DEG C of reaction 48h are warming up to, is made and precipitates containing light yellow crystal
Solidliquid mixture, obtains single pyridine villaumite after being then filtered, washed and dried, reaction equation is as follows：
B. iron content pyridine chloride salt ions liquid is prepared
Single pyridine villaumite and ferric chloride hexahydrate are added in three-necked flask and are mixed, single pyridine villaumite and six hydrations
The molar ratio of iron chloride is 1：1,120 DEG C of reaction 6h are warming up to, the iron content pyridine chloride salt ions liquid of clear yellow viscous, reaction is made
Equation is as follows：
Embodiment 2
The present embodiment provides a kind of preparation methods of iron content pyridine chloride salt ions liquid, include the following steps：
A. single pyridine villaumite is prepared
Under nitrogen protection, 6 ethyls-substituted pyridines and monochloro methane are added in three-necked flask and are mixed, 6 second
The molar ratio of base-substituted pyridines and monochloro methane is 1：1.3, it is warming up to 60 DEG C of reactions for 24 hours, is made and is precipitated containing light yellow crystal
Solidliquid mixture, single pyridine villaumite is obtained after being then filtered, washed and dried, reaction equation is as follows：
B. iron content pyridine chloride salt ions liquid is prepared
Single pyridine villaumite and ferric chloride hexahydrate are added in three-necked flask and are mixed, single pyridine villaumite and six hydrations
The molar ratio of iron chloride is 1：1,140 DEG C of reaction 6h are warming up to, the iron content pyridine chloride salt ions liquid of clear yellow viscous, reaction is made
Equation is as follows：
Embodiment 3
The present embodiment provides a kind of preparation methods of iron content pyridine chloride salt ions liquid, include the following steps：
A. single pyridine villaumite is prepared
Under nitrogen protection, 6 methyl-substituted pyridines and monochloro methane are added in three-necked flask and are mixed, 6 first
The molar ratio of base-substituted pyridines and monochloro methane is 1：1.2,100 DEG C of reaction 60h are warming up to, are made heavy containing light yellow crystal
The solidliquid mixture in shallow lake, obtains single pyridine villaumite after being then filtered, washed and dried, reaction equation is as follows：
B. iron content pyridine chloride salt ions liquid is prepared
Single pyridine villaumite and ferric chloride hexahydrate are added in three-necked flask and are mixed, single pyridine villaumite and six hydrations
The molar ratio of iron chloride is 1：1,150 DEG C of reaction 12h are warming up to, the iron content pyridine chloride salt ions liquid of clear yellow viscous are made, instead
Answer equation as follows：
Embodiment 4
The present embodiment provides a kind of preparation methods of iron content pyridine chloride salt ions liquid, include the following steps：
A. single pyridine villaumite is prepared
Under nitrogen protection, 6 ethyls-substituted pyridines and monochlorethane are added in three-necked flask and are mixed, 6 second
The molar ratio of base-substituted pyridines and monochlorethane is 1：1.2,40 DEG C of reaction 10h are warming up to, is made and is precipitated containing light yellow crystal
Solidliquid mixture, single pyridine villaumite is obtained after being then filtered, washed and dried, reaction equation is as follows：
B. iron content pyridine chloride salt ions liquid is prepared
Single pyridine villaumite and ferric chloride hexahydrate are added in three-necked flask and are mixed, single pyridine villaumite and six hydrations
The molar ratio of iron chloride is 1：0.9,100 DEG C of reaction 0.5h are warming up to, the iron content pyridine chloride salt ions liquid of clear yellow viscous is made,
Reaction equation is as follows：
Embodiment 5
The present embodiment provides a kind of preparation methods of iron content pyridine chloride salt ions liquid, include the following steps：
A. single pyridine villaumite is prepared
Under nitrogen protection, 6 ethyls-substituted pyridines and a chloropropane are added in three-necked flask and are mixed, 6 second
The molar ratio of base-substituted pyridines and monochlorethane is 1：1.2,80 DEG C of reaction 36h are warming up to, is made and is precipitated containing light yellow crystal
Solidliquid mixture, single pyridine villaumite is obtained after being then filtered, washed and dried, reaction equation is as follows：
B. iron content pyridine chloride salt ions liquid is prepared
Single pyridine villaumite and ferric chloride hexahydrate are added in three-necked flask and are mixed, single pyridine villaumite and six hydrations
The molar ratio of iron chloride is 1：1.1,130 DEG C of reaction 5h are warming up to, the iron content pyridine chloride salt ions liquid of clear yellow viscous are made, instead
Answer equation as follows：
Embodiment 6
A kind of iron content pyridine chloride salt ions liquid is provided in the present embodiment in the catalysis for preparing N-serve
Application in agent, includes the following steps：
A. molecular sieve carried iron content pyridine chloride salt ions liquid catalyst is prepared
It is 1 to weigh mass ratio：0.048：2 molecular sieve, iron content pyridine chloride salt ions liquid and absolute ethyl alcohol is added to three
It is mixed in mouth flask, the three-necked flask equipped with mixture is then put into ultrasound in super emperorship, after impregnating for 24 hours, at 80 DEG C
Dry 12h, is made molecular sieve carried iron content pyridine chloride salt ions liquid catalyst.
B. catalyst preparation N-serve is used
The molecular sieve carried iron content pyridine chloride salt ions liquid catalysts of 1g are taken to be placed in reactor, by the 2- methyl after gasification
Pyridine solution, chlorine and inert gas are with 100h-1Volume space velocity be passed into reactor, setting reaction temperature be 240 DEG C,
It collects condensed product and N-serve is made.
In conclusion a kind of iron content pyridine chloride salt ions liquid provided in an embodiment of the present invention, iron content pyridine chloride salt ions
Liquid can be made as the main component for the catalyst for preparing N-serve, iron content pyridine chloride salt ions liquid
The product yield for preparing N-serve can be improved for catalyst and reduces its chlorination reaction temperature, and iron content
Pyridine chloride salt ions liquid can be used as a kind of long catalytic life and renewable free of contamination green catalyst.
A kind of preparation method of iron content pyridine chloride salt ions liquid provided in an embodiment of the present invention, this preparation method is easy,
It being capable of efficient preparation iron content pyridine chloride salt ions liquid.
The embodiment of the present invention provides iron content pyridine chloride salt ions liquid in the catalyst for preparing N-serve
In application, iron content pyridine chloride salt ions liquid is the important source material for the catalyst for preparing N-serve, is being urged
Change prepare played in the reaction of N-serve accelerate reaction speed, improve product yield and reduce its chlorination it is anti-
Answer the function of temperature.
Embodiments described above is a part of the embodiment of the present invention, instead of all the embodiments.The reality of the present invention
The detailed description for applying example is not intended to limit the range of claimed invention, but is merely representative of the selected implementation of the present invention
Example.Based on the embodiments of the present invention, those of ordinary skill in the art are obtained without creative efforts
Every other embodiment, shall fall within the protection scope of the present invention.
Claims (10)
1. a kind of iron content pyridine chloride salt ions liquid, which is characterized in that the general structure of the iron content pyridine chloride salt ions liquid
It is as follows：
Wherein R1And R2It is alkyl.
2. iron content pyridine chloride salt ions liquid according to claim 1, which is characterized in that the R1For CnH2n+1(n=1~
4), it is preferred that the R1For methyl or ethyl, the R2For CnH2n+1(n=1~18).
3. a kind of preparing the preparation method such as claim 1~2 any one of them iron content pyridine chloride salt ions liquid, feature
It is comprising the iron content pyridine chloride salt ions liquid is synthesized by single pyridine villaumite and ferric chloride hexahydrate.
4. the preparation method of iron content pyridine chloride salt ions liquid according to claim 3, which is characterized in that by single pyrrole
After pyridine villaumite and ferric chloride hexahydrate mixing, the iron content pyridine chloride salt ions liquid is made in 0.5~12h of temperature reaction.
5. the preparation method of iron content pyridine chloride salt ions liquid according to claim 4, which is characterized in that the list pyridine
The molar ratio of villaumite and the ferric chloride hexahydrate is 1：(0.9~1.1).
6. the preparation method of iron content pyridine chloride salt ions liquid according to claim 4, which is characterized in that reaction temperature is
100~150 DEG C.
7. the preparation method of iron content pyridine chloride salt ions liquid according to claim 3, which is characterized in that it further includes leading to
Cross 6- substituted pyridines and chlorine alkane substitute synthesis single pyridine villaumite.
8. the preparation method of iron content pyridine chloride salt ions liquid according to claim 7, which is characterized in that in inert gas
Under protection, after the 6- substituted pyridines and the chlorine alkane substitute are mixed, 40~100 DEG C of 10~60h of reaction are warming up to,
Single pyridine villaumite is obtained after filtering, washing and drying.
9. the preparation method of iron content pyridine chloride salt ions liquid according to claim 8, which is characterized in that the 6- substitutions
The molar ratio of pyridine and the chlorine alkane substitute is 1：(1~1.3).
10. as claim 1~2 any one of them iron content pyridine chloride salt ions liquid is preparing the chloro- 6- trichloromethyls pyrroles of 2-
Application in the catalyst of pyridine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108530346A (en) * | 2018-05-07 | 2018-09-14 | 盐城工学院 | A kind of preparation method of N-serve and its preparation method of catalyst and catalyst |
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| CN102701926A (en) * | 2012-06-19 | 2012-10-03 | 河北工业大学 | Technical method for preparing 2-ethyl-2-hexenal by catalyzing self-condensation of n-butyraldehyde with acidic ionic liquid |
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| CN101648905A (en) * | 2009-09-10 | 2010-02-17 | 北京颖泰嘉和科技股份有限公司 | Preparation method of 2- chloro-6-trichloromethyl pyridine |
| CN102701926A (en) * | 2012-06-19 | 2012-10-03 | 河北工业大学 | Technical method for preparing 2-ethyl-2-hexenal by catalyzing self-condensation of n-butyraldehyde with acidic ionic liquid |
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| CN108530346A (en) * | 2018-05-07 | 2018-09-14 | 盐城工学院 | A kind of preparation method of N-serve and its preparation method of catalyst and catalyst |
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