CN109896963A - A kind of synthetic method of 4- methylamino paraxylene ring two-body - Google Patents
A kind of synthetic method of 4- methylamino paraxylene ring two-body Download PDFInfo
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- CN109896963A CN109896963A CN201910162215.6A CN201910162215A CN109896963A CN 109896963 A CN109896963 A CN 109896963A CN 201910162215 A CN201910162215 A CN 201910162215A CN 109896963 A CN109896963 A CN 109896963A
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Abstract
The invention discloses a kind of synthetic methods of 4- methylamino paraxylene ring two-body, include the following steps: (1) with [2, 2]-paraxylene ring two-body is raw material, using methylene chloride as reaction dissolvent, under titanium tetrachloride catalytic action, using dichloromethyl ether as alkylating agent, Rieche reaction occurs, generate 4- formoxyl-[2, 2]-paraxylene ring two-body (2) 4- formoxyl-[2, 2]-paraxylene ring two-body is placed in reaction kettle and is passed through ammonia, hydrogen carries out reduction reaction under hydrogenation catalyst effect, obtain crude product, by concentration, recrystallization, 4- methylamino-[2 is obtained after drying, 2]-paraxylene ring two-body.
Description
Technical field
The invention belongs to organic chemical synthesis field, in particular to a kind of synthesis side of 4- methylamino paraxylene ring two-body
Method.
Background technique
Parylene coating material has unique physical characteristic and electrical characteristics, and unique molecular level depositional model makes
It is widely applied in multiple fields such as MEMS, medical instrument, historical relic's protection, electronics industry, can be used as MEMS device
In micromechanics components and sliding coating；It can be used as the lubrication corrosion-inhibiting coating of medical instrument, human organ；It can be used as text
The reinforcement protection coating of object, sample；It can also be used as dielectric material, the protective coating in semiconductor product, and electronics can be improved
The reliability of product.As people are to the further awareness and understanding of Parylene coating material characteristic, this kind of material can be more
Extensive field is applied and promotes, and currently application is attempted in airtight protection, three proofings etc., such as does in hybrid circuit
Insulation and insulation blocking, the waterproof salt spray proof of product protected with Parylene coating, as airtight material etc..At present
Parylene episode presoma gradually synthesizes, but Parylene AM presoma does not still enter research, and the material
Material is widely used market, thus the research significance is great.
Summary of the invention
Technical problem: in order to overcome the above-mentioned deficiencies of the prior art, a kind of the present invention provides side reactions few, product yield
The synthetic method of 4- methylamino paraxylene ring two-body that is high, greatly reducing environmental pollution.
Technical solution: the synthetic method of 4- methylamino paraxylene ring two-body of the invention, steps are as follows:
(1) by paraxylene ring two-body, nitromethane, methylene chloride, mixing machinery stirs 10~20min, nitrogen at 0 DEG C
After titanium tetrachloride solution is added dropwise, dichloromethyl ether is added, room temperature reaction 2.5-3h obtains crude product, through organic molten in gas shielded
4- formoxyl-[2,2]-paraxylene ring two-body is obtained after agent recrystallization；
(2) by 4- formoxyl-[2,2]-paraxylene ring two-body obtained in the step (1) and reaction dissolvent plus hydrogen
Catalyst, which is added in the autoclave filled with ammonia and hydrogen, carries out reduction reaction, and gained crude product is after organic solvent recrystallizes
Obtain 4- methylamino-[2,2]-paraxylene ring two-body product.
Further, in the method for the present invention, the mass ratio of titanium tetrachloride and paraxylene ring two-body is in the step (1)
(1-3): 1, the mass ratio of dichloromethyl ether and paraxylene ring two-body is (0.1-1): 1.
In above scheme, the mass ratio of titanium tetrachloride and paraxylene ring two-body is preferably 1.8: 1；Dichloromethyl ether with
The mass ratio of paraxylene ring two-body is preferably than being 0.66: 1.
Further, in the method for the present invention, the organic solvent that recrystallization uses in the step (1) is dehydrated alcohol and four
Hydrogen furans mixed solvent, dehydrated alcohol and methylene chloride mixed solvent or dehydrated alcohol and ethyl acetate mixed solvent.
In above scheme, the preferred tetrahydrofuran of organic solvent and alcohol mixed solvent.
Further, in the method for the present invention, the reaction dissolvent in the step (2) is methanol, dehydrated alcohol, dichloromethane
Any one of alkane, carbon tetrachloride, tetrahydrofuran.
In above scheme, organic solvent is preferably dehydrated alcohol.
Further, in the method for the present invention, the hydrogenation catalyst in the step (2) is charcoal load cobalt, charcoal is copper-loaded, thunder Buddhist nun
Any one of nickel, palladium carbon catalyst, the mass ratio of the hydrogenation catalyst and 4- formoxyl-[2,2]-paraxylene ring two-body
For (0.01-0.08): 1.
In above scheme, the mass ratio of hydrogenation catalyst and 4- formoxyl-[2,2]-paraxylene ring two-body is preferably
0.03∶1。
Further, in the method for the present invention, the organic solvent that recrystallization uses in the step (2) is methanol, ethyl alcohol, two
Any one of chloromethanes, tetrahydrofuran.
In above scheme, organic solvent is preferably methanol.
Further, in the method for the present invention, the condition of reduction reaction is 40-100 DEG C of reaction temperature, hydrogen in step (2)
Pressure 0.5-4.0MPa, ammonia pressure 0.1-1.2MPa.
It is 60 DEG C that the condition of reduction reaction, which is preferably reaction temperature, in above scheme, in step (2), and Hydrogen Vapor Pressure is
3MPa, ammonia pressure 0.8MPa.
The synthetic route of the method for the present invention is as follows:
The utility model has the advantages that the present invention compared with the existing technology, has the advantage that
(1) synthetic method of 4- methylamino paraxylene ring two-body provided by the invention is using titanium tetrachloride as Louis
Acid catalyst, compared to than using the lewis acids such as alchlor as catalyst in conventional method, yield is significantly improved.Compared to text
The method for offering middle synthesis methylamino benzene, when a certain amount of nitromethane is added as co-catalyst, the addition product of generation is catalyzed
Effect enhancing, raw material energy fully reacting, and reduce by-product, yield increase, and effectively shorten the reaction time.
(2) the seriously polluted iron powder catalyst of use environment and traditional hydrazine hydrate reduction are avoided in reduction reaction, are solved
Hydrazine hydrate solution of having determined reduction can not fully reacting and reaction time long problem, and using being urged in Raney's nickel reduction process
Agent and solvent are recyclable, and the reaction time is short, improve yield, reduce environmental hazard, reduce production cost.
(3) reduction reaction process using 4- formoxyl paraxylene ring two-body is raw material in the present invention, raw with ammonia
At alkene ammoniate, 4- methylamino paraxylene ring two-body then is generated with ammonia hydrogenation reduction again, the process is for existing
There is technology, is a kind of new synthetic route.
Specific embodiment
Below in conjunction with specific embodiment, exemplary illustration and help further understand essence of the invention, but embodiment is specific
Details does not represent whole technical solutions under present inventive concept merely to illustrate the present invention, therefore should not be construed as to this hair
Bright total technical solution limits, some to increase for the technician without departing from the unsubstantiality of present inventive concept or change, example
Such as simply change or replace with the technical characteristic with same or similar technical effect, the category scope of the present invention.
Synthesize 4- methylamino-[2,2]-paraxylene ring two-body
Embodiment 1
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.664g titanium tetrachloride (syringe addition), adds after stirring 10min
Enter dichloromethyl ether 0.689g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slow
Slowly it pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, emulsus is added in organic layer
Object becomes light green color, extracts liquid separation, and organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is light green for removing solvent and obtaining crude product
Color solid, dehydrated alcohol and tetrahydrofuran recrystallize to obtain 0.98g4- formoxyl-[2,2]-paraxylene ring two-body.To autoclave
Middle addition 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml dehydrated alcohol, 0.03g Raney's nickel catalyst, in 60 DEG C, ammonia
Atmospheric pressure is 0.8MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 3MPa.After reaction, catalyst is recovered by filtration, rotates
Recycling design obtains product 0.9g by recrystallizing methanol.Overall yield of reaction 70.55%, purity 98.3%.
Embodiment 2
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.04g titanium tetrachloride (syringe addition), adds after stirring 15min
Enter dichlormethyl ether 0.689g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slowly fallen
Enter in 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing is added in organic layer, and milk becomes
For light green color, liquid separation is extracted, organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is solid for light green color that removing solvent obtains crude product
Body, dehydrated alcohol and tetrahydrofuran recrystallize to obtain 0.62g4- formoxyl-[2,2]-paraxylene ring two-body.Add into autoclave
Enter 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml dehydrated alcohol, 0.03g Raney's nickel catalyst, is in ammonia pressure
0.8MPa, Hydrogen Vapor Pressure are stirred to react 5h under the conditions of being 3MPa.After reaction, catalyst is recovered by filtration, rotates recycling design,
Product 0.6g is recrystallized to give by dehydrated alcohol.Overall yield of reaction 31.53%, purity 98.3%.
Embodiment 3
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, lml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 3.12g titanium tetrachloride (syringe addition), adds after stirring 10min
Enter dichloromethyl ether 0.689g (syringe addition), 2.8h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slow
Slowly it pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, emulsus is added in organic layer
Object becomes light green color, extracts liquid separation, and organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is light green for removing solvent and obtaining crude product
Color solid, dehydrated alcohol and re-crystallizing in ethyl acetate obtain 0.72g4- formoxyl-[2,2]-paraxylene ring two-body.To autoclave
Middle addition 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml anhydrous methanol, 0.03g Raney's nickel catalyst, in 60 DEG C, ammonia
Atmospheric pressure is 0.8MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 4MPa.After reaction, catalyst is recovered by filtration, rotates
Recycling design obtains product 0.84g by recrystallizing methanol.Overall yield of reaction 51.25%, purity 98.3%.
Embodiment 4
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.664g titanium tetrachloride (syringe addition), adds after stirring 20min
Enter dichloromethyl ether 0.104g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slow
Slowly it pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, emulsus is added in organic layer
Object becomes light green color, extracts liquid separation, and organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is light green for removing solvent and obtaining crude product
Color solid, dehydrated alcohol and tetrahydrofuran recrystallize to obtain 0.46g4- formoxyl-[2,2]-paraxylene ring two-body.To autoclave
Middle addition 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml dehydrated alcohol, 0.01g Raney's nickel catalyst, in 60 DEG C, ammonia
Atmospheric pressure is 0.1MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 3MPa.After reaction, catalyst is recovered by filtration, rotates
Recycling design obtains product 0.63g by recrystallizing methanol.Overall yield of reaction 24.56%, purity 98.3%.
Embodiment 5
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.664g titanium tetrachloride (syringe addition), adds after stirring 10min
Enter dichloromethyl ether 1.04g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, slowly by reaction solution
It pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, milk is added in organic layer
Become light green color, extract liquid separation, organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and removing solvent and obtaining crude product is light green color
Solid, dehydrated alcohol and tetrahydrofuran recrystallize to obtain 0.85g4- formoxyl-[2,2]-paraxylene ring two-body.Into autoclave
1g formoxyl-[2,2]-paraxylene ring two-body, 30ml tetrahydrofuran, 0.08g charcoal is added and carries Co catalysts, in 60 DEG C, ammonia
Pressure is 0.8MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 0.5MPa.After reaction, catalyst is recovered by filtration, rotates
Recycling design obtains product 0.3g by recrystallize with dichloromethane.Overall yield of reaction 21.61%, purity 98.3%.
Embodiment 6
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.664g titanium tetrachloride (syringe addition), adds after stirring 10min
Enter dichloromethyl ether 0.689g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slow
Slowly it pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, emulsus is added in organic layer
Object becomes light green color, extracts liquid separation, and organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is light green for removing solvent and obtaining crude product
Color solid, dehydrated alcohol and tetrahydrofuran recrystallize to obtain 0.98g4- formoxyl-[2,2]-paraxylene ring two-body.To autoclave
Middle addition 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml dehydrated alcohol, the copper-loaded catalyst of 0.03g charcoal, in 60 DEG C, ammonia
Atmospheric pressure is 0.8MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 2MPa.After reaction, catalyst is recovered by filtration, rotates
Recycling design obtains product 0g by recrystallizing methanol.Overall yield of reaction 0%, purity 0%.
Embodiment 7
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.664g titanium tetrachloride (syringe addition), adds after stirring 10min
Enter dichloromethyl ether 0.689g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slow
Slowly it pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, emulsus is added in organic layer
Object becomes light green color, extracts liquid separation, and organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is light green for removing solvent and obtaining crude product
Color solid, dehydrated alcohol and recrystallize with dichloromethane obtain 0.74g4- formoxyl-[2,2]-paraxylene ring two-body.To autoclave
Middle addition 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml ethyl acetate, 0.03gPd/C catalyst, in 40 DEG C, ammonia
Pressure is 1.2MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 3MPa.After reaction, catalyst is recovered by filtration, rotates back
Solvent is received, product 0.32g is recrystallized to give by tetrahydrofuran.Overall yield of reaction 20.07%, purity 98.3%.
Embodiment 8
Take 1.04g paraxylene ring two-body in 100ml three-neck flask, addition 20ml methylene chloride, 1ml nitromethane,
It reacts and is passed through nitrogen protection, system is in 0 DEG C of reaction, is added dropwise 1.664g titanium tetrachloride (syringe addition), adds after stirring 10min
Enter dichloromethyl ether 0.689g (syringe addition), 2.5h post-processing reaction is reacted at room temperature after being added dropwise, reaction solution is slow
Slowly it pours into 200ml ice water, liquid separation is extracted after mechanical stirring 30min, 7ml hydrochloric acid (6mol/L) washing, emulsus is added in organic layer
Object becomes light green color, extracts liquid separation, and organic layer is washed to neutrality, and anhydrous magnesium sulfate is dry, and it is light green for removing solvent and obtaining crude product
Color solid, dehydrated alcohol and tetrahydrofuran recrystallize to obtain 0.98g4- formoxyl-[2,2]-paraxylene ring two-body.To autoclave
Middle addition 1g formoxyl-[2,2]-paraxylene ring two-body, 30ml dehydrated alcohol, 0.03gPd/C catalyst, in 100 DEG C, ammonia
Pressure is 0.8MPa, and Hydrogen Vapor Pressure is stirred to react 5h under the conditions of being 3MPa.After reaction, catalyst is recovered by filtration, rotates back
Solvent is received, product 0.62g is obtained by recrystallizing methanol.Overall yield of reaction 51.49%, purity 98.3%.
Claims (7)
1. a kind of synthetic method of 4- methylamino paraxylene ring two-body, which is characterized in that method includes the following steps:
(1) by paraxylene ring two-body, nitromethane, methylene chloride, mixing machinery stirs 10~20min at 0 DEG C, and nitrogen is protected
After titanium tetrachloride solution is added dropwise, dichloromethyl ether is added, room temperature reaction 2.5-3h obtains crude product, through organic solvent weight in shield
4- formoxyl-[2,2]-paraxylene ring two-body is obtained after crystallization；
(2) by 4- formoxyl-[2,2]-paraxylene ring two-body obtained in the step (1) and reaction dissolvent, hydrogenation catalyst
Agent, which is added in the autoclave filled with ammonia and hydrogen, carries out reduction reaction, and gained crude product obtains after organic solvent recrystallizes
4- methylamino-[2,2]-paraxylene ring two-body product.
2. a kind of synthetic method of 4- methylamino paraxylene ring two-body described in accordance with the claim 1, which is characterized in that described
The mass ratio of titanium tetrachloride and paraxylene ring two-body is (1-3) in step (1): 1, dichloromethyl ether and paraxylene ring two
The mass ratio of body is (0.1-1): 1.
3. the synthetic method of 4- methylamino paraxylene ring two-body described in accordance with the claim 1, which is characterized in that
The organic solvent that recrystallization uses in the step (1) is dehydrated alcohol and tetrahydrofuran mixed solvent, dehydrated alcohol and
Methylene chloride mixed solvent or dehydrated alcohol and ethyl acetate mixed solvent.
4. a kind of synthetic method of 4- methylamino paraxylene ring two-body described in accordance with the claim 1, which is characterized in that described
Reaction dissolvent in step (2) be methanol, dehydrated alcohol, methylene chloride, carbon tetrachloride, tetrahydrofuran, any one of.
5. according to a kind of synthetic method of 4- methylamino paraxylene ring two-body described in claim 1,2,3 or 4, feature exists
In the hydrogenation catalyst in the step (2) is that charcoal carries any one of copper-loaded cobalt, charcoal, Raney's nickel, palladium carbon catalyst, described
The mass ratio of hydrogenation catalyst and 4- formoxyl-[2,2]-paraxylene ring two-body is (0.01-0.08): 1.
6. according to a kind of synthetic method of 4- methylamino paraxylene ring two-body described in claim 1,2,3 or 4,
It is characterized in that, the organic solvent that recrystallization uses in the step (2) is methanol, ethyl alcohol, methylene chloride, tetrahydrofuran
Any one of.
7. according to a kind of synthetic method of 4- methylamino paraxylene ring two-body described in claim 1,2,3 or 4, feature exists
In the condition of reduction reaction is 40-100 DEG C of reaction temperature, Hydrogen Vapor Pressure 0.5-4.0MPa, ammonia pressure in the step (2)
0.1-1.2MPa。
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| CN112521242A (en) * | 2020-12-03 | 2021-03-19 | 东南大学 | Preparation method of 4-n-propyl-p-xylene cyclic dimer |
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Application publication date: 20190618 |