CN104016868A - Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof - Google Patents

Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof Download PDF

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CN104016868A
CN104016868A CN201410133037.1A CN201410133037A CN104016868A CN 104016868 A CN104016868 A CN 104016868A CN 201410133037 A CN201410133037 A CN 201410133037A CN 104016868 A CN104016868 A CN 104016868A
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chlorobenzaldehyde
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CN104016868B (en
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彭新华
徐俊辉
魏建平
李芳美
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Nanjing University of Science and Technology
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Abstract

The invention discloses 2, 4, 6-trinitro-1, 3-distyryl benzene derivatives containing chlorine substituent as well as a preparation method and an application thereof. The chemical structure of the compounds is characterized in that three nitryls exist at positions 2, 4, 6 of a middle benzene ring of 1, 3-distyryl benzene, and ortho-positions, meta-positions and para-positions of benzene rings at the two sides are connected to chlorine atoms, or the ortho-positions and the para-positions are simultaneously connected to the chlorine atoms. The chemical structure of the compounds is confirmed to be the trans-structure when the coupling constant of diphenylethene double bonds in a nuclear magnetic resonance spectrum is about 16.0Hz. The 2, 4, 6-trinitro-1, 3-distyryl benzene derivatives containing chlorine substituent are synthesized through microwave assistance under a catalysis condition, are simple in a preparation technology, solvent-free, fast, green and safe and can be potentially applied to the field of luminescent devices and energetic materials.

Description

Chloride 2,4,6-trinitro--1,3-diphenylethyllene benzene derivative, preparation and application thereof
Technical field
The invention belongs to energetic material and organic light emission field, be specifically related to a kind of 2,4 of chlorine substituent that contains, 6-trinitro--1,3-diphenylethyllene benzene derivative, preparation and application thereof.
Background technology
The two keys that exist in diphenylethylene compounds structure and the conjugative effect of phenyl ring, make such compound chemistry character more stable.Many nitros stilbenes compound is the very important chemical intermediate of one, can be widely used in the field of nonlinear optics and the heat-resisting energetic material of high energy.For example it can be used for synthesizing new part for nonlinear optical material and as the high temperature powder of military and civilian.Wherein, the significant picryl sulfide base of performance ethene (HNS) belongs to the one in many nitros stilbenes compound, it is yellow crystals, and fusing point, up to 317 DEG C, is a kind of high temperature powder, there is good physics, chemical stability, mechanical sensitivity is low, insensitive to static sparking, and radiation resistance is strong, by first being made by the K.G.Shipp of Swede the sixties in last century, being widely used in the field such as oilfield exploitation and aerospace.
Document (G.X.Wang, C.H.Shi, X.D.Gong, H.M.Xiao, J.Phys.Chem.A2009,113,1318) by theoretical research the performances such as the structure of many nitro toluylenes derivative, density, detonation parameter, such material shows very strong applicability.Document (Z.G.FengandB.R.Chen, Prop., Explos., Pyrotech., 1991,16,12; Z.G.FengandB.R.Chen, Prop., Explos., Pyrotech.1992,17,237; L.Q.Wang, Y.H.Liu, J.G.Zhang, T.L.Zhang, L.Yang, X.J.Qiao, X.C.HuandJ.Y.Guo, Chin.J.Chem.2007,25,1044) also report the compound that has synthesized a series of many nitro toluylenes, such compounds property is superior, simultaneously owing to thering are two keys, whole molecular system has stronger conjugative effect, thereby can promote the fusing point of this compounds, i.e. resistance toheat.Wherein chloride 2,4,6-trinitro--1, the chlorine atom in 3-diphenylethyllene benzene derivative can be transformed into (the NH of other functional group as active function groups 2,-N 3,-NO 2deng) or be connected with other structural unit; Document (A.Kvaran, A.E. , C.Evans, J.K.F.Geirsson, J.Mol.Struct.2000,553,79 – 90) also inquire into the relation between photochemistry and the structure of similar structures.So there is extremely important status compound synthetic that builds many nitros diphenylethlene class novel under other conjugated system.
The research of microwave reaction in promotion organic reaction has become a focus of organic chemistry filed, a large amount of experimental studies show, carry out organic reaction by microwave technology, even thousands of times of the fast decades of times of heating means that speed of response is more traditional, and have easy and simple to handle, productive rate is high and the feature such as easy purification of products, safety, therefore, microwave organic reaction development rapidly.There are some documents to relate in pyrroles's catalysis by synthetic diphenyl ethylene derivatives under microwave condition.(K.M.Poulsen, T.Reenberg, T. andJ.B.Christensen, Synth.Commun.2004,34,2215; S.SaravananandP.C.Srinivasan, Synth.Commun.2001,31,823) still, many nitro compounds have certain explosivity, directly under microwave-excitation, temperature is wayward, is easy to cause the decomposition of compound, has potential danger.
Summary of the invention
The object of this invention is to provide a class and contain 2,4 of chlorine substituent, 6-trinitro--1,3-diphenylethyllene benzene derivative, and the microwave assisted synthesizing method of this compound is provided, this compound can potentially apply to luminescent device and energetic material field.
Realizing the object of the invention technical scheme is:
A kind of chloride 2,4,6-trinitro--1,3-diphenylethyllene benzene derivative, is characterized in that its chemical structural formula of this compound is:
Wherein, in molecular structure, 2,4,6 on the middle phenyl ring of 1,3-diphenylethyllene benzene have three nitros, and neighbour on the phenyl ring of both sides,, contraposition is connected with chlorine atom, namely R 1, R 2, R 3in have one be connected with chlorine atom other for hydrogen, or R 1, R 3be chlorine atom simultaneously, R 2for hydrogen atom.
Above-mentioned 2,4 of the chlorine substituent that contains, 6-trinitro--1, the preparation method of 3-diphenylethyllene benzene derivative, is characterized in that comprising following reaction formula and step:
By 2,4,6-trinitro-m-xylene and Chlorobenzaldehyde mixed dissolution, in organic solvent, add basic catalyst and carrier, raw material and basic catalyst uniform loading are on carrier, under normal pressure, except desolventizing, obtain the solid mixture of load raw material, then this solid mixture is transferred in microwave reactor, under certain output rating, react, reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, and crude product obtains target product after recrystallization.Wherein, Chlorobenzaldehyde is selected o-chlorobenzaldehyde, m chlorobenzaldehyde, 4-chloro-benzaldehyde and 2,4 dichloro benzene formaldehyde.
Wherein, the alkaline catalysts adding is selected one or more in N methyl piperazine, morpholine, triethylamine, pyridine, piperidines.
In reaction 2,4, the mol ratio of 6-trinitro-m-xylene and Chlorobenzaldehyde is 1:2.1, and the reaction times is 15min.
In reaction, carrier is selected silica gel, NaOH, KOH, K 2cO 3in one (NaOH, KOH, K 2cO 3for pressed powder).
In reaction, the output rating of microwave is set to 300-400W.
Organic solvent is selected methylene dichloride, and recrystallization solvent is selected acetone-alcohol mixed solvent.
Above-mentioned 2,4 of the chlorine substituent that contains, 6-trinitro--1, the application of 3-diphenylethyllene benzene derivative, the type compound can be used in optical material field, as nonlinear optical organic, photosensitizers etc. or the important intermediate as energetic material field.
The present invention compared with prior art, its remarkable advantage is: (1) synthetic 2 of chlorine substituent that contains, 4,6-trinitro--1,3-diphenylethyllene benzene derivative, the compound of the type has the structure type of typical D-π-A-π-D system, and (wherein D represents supplied for electronic group, π represents electronic bridge, is two keys in structure, and A represents electron acceptor(EA), be electron-withdrawing group), this kind of structure type is conducive to the transmission of electronics.From ultraviolet-visible light spectrum analysis, this analog derivative absorption bands is wide, and absorbing wavelength, near ultraviolet and visible region, embodies good optical characteristics; (2) synthesize this compounds by traditional method and need long time (reaching 48h), cause like this loss and the waste of time of the energy; And adopt microwave reaction only to need 15min just can reach comparatively ideal productive rate.(3) many nitro-compounds have certain danger, directly synthetic under the condition of microwave-excitation, easily form too high raw material or the product of making of local temperature and decompose.And adopt inexpensive callable silica gel to carry out load, and can make raw material or product disperse, make whole reaction system safer.(4) need to use benzene or toluene as solvent and azeotropic agent by traditional method, benzene is harmful to environment, does not meet the requirement of Green Chemistry, and adopts novel method of the present invention to synthesize, and avoids using solvent, forms solvent-free system.
Brief description of the drawings
Fig. 1 is product 2,4 in example 1 of the present invention, 6-trinitro--1, and the hydrogen nuclear magnetic spectrum of 3-bis-(4 '-chloro-styrene base) benzene, X-coordinate is chemical shift.
Fig. 2 is product 2,4 in example 2 of the present invention, 6-trinitro--1, and the hydrogen nuclear magnetic spectrum of 3-bis-(2 '-chloro-styrene base) benzene, X-coordinate is chemical shift.
Fig. 3 is product 2,4 in the embodiment of the present invention 3,6-trinitro--1, and the hydrogen nuclear magnetic spectrum of 3-bis-(2 ', 4 '-dichlorostyrene base) benzene, X-coordinate is chemical shift.
Fig. 4 is product 2,4 in the embodiment of the present invention 6,6-trinitro--1, the relation curve of 3-bis-(4 '-chloro-styrene base) benzene absorbancy and wavelength in trichloromethane.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in further detail.
Embodiment 1:
2,4,6-trinitro--1,3-bis-(4 '-chloro-styrene base) benzene (R 1, R 2for hydrogen atom, R 3for chlorine atom) microwave synthetic:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 4-chloro-benzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip piperidines 0.08g (0.9mmol) and carrier silica gel (3.0g), raw material and basic catalyst uniform loading are on carrier, under normal pressure, remove desolventizing, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.75g), productive rate 77%.
Yellow crystals, fusing point: 158-160 DEG C, IR (ν, cm -1): 3094,1634,1588,1543,1490,1333,972; 1hNMR (500MHz, CDCl 3), δ 8.76(s, 1H), 7.43-7.37 (m, 8H), 7.17 (d, J=16.60Hz, 2H), 6.84 (d, J=16.60Hz, 2H), 1.56 (s, H 2o); (as shown in Figure 1)
13cNMR (126MHz, CDCl3), δ 145.70,136.68,135.02,132.31,129.89,128.26,127.68,127.35,120.78,115.34. mass spectrum molecular ion peak is: 485.029
Concrete reaction equation is as follows:
Embodiment 2:
2,4,6-trinitro--1,3-bis-(2 '-chloro-styrene base) benzene (R 2, R 3for hydrogen atom, R 1for chlorine atom) microwave synthetic:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and o-chlorobenzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip piperidines 0.08g (0.9mmol) and carrier NaOH(3.0g), raw material and basic catalyst uniform loading are on carrier, under normal pressure, remove desolventizing, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.88g), productive rate 85.7%.
Yellow solid, fusing point: 167-168 DEG C, IR (ν, cm -1): 3098,1631,1602,1547,1473,1402,1347,979; 1hNMR (500MHz, CDCl 3), δ 8.82 (s, 1H), 7.66 – 7.64 (m, 2H); 7.42 – 7.40 (m, 2H), 7.33 – 7.32 (m, 4H), 7.29 (d; J=16.60Hz, 2H), 7.20 (d, J=16.60Hz, 2H); (as shown in Figure 2)
13cNMR (126MHz, CDCl 3), 151.01,145.83,134.10,133.32,132.25,130.22,129.83,129.03,126.40,126.27,120.80,117.58. mass spectrum molecular ion peak is: 485.118
Concrete reaction equation is as follows:
Embodiment 3:
2,4,6-trinitro--1,3-bis-(2 ', 4 '-dichlorostyrene base) benzene (R 1, R 3for chlorine, R 2for hydrogen atom) microwave synthetic:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 2,4-dichlorobenzaldehyde (0.70g, 4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip morpholine and carrier salt of wormwood (3.0g), raw material and basic catalyst uniform loading are on carrier, under normal pressure, remove desolventizing, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.90g), productive rate 81.1%.
Yellow solid, fusing point: 166-167 DEG C, IR (ν, cm -1): 3095,1633,1545,1383,1339,976; 1h NMR (500MHz, CDCl 3), δ 8.81(s, 1H), 7.56 (d, J=2.00Hz, 2H), 7.50(d, J=8.40Hz, 2H), 7.32-7.30(dd, J 1=2.00Hz, J 2=8.40Hz, 2H), 7.19(d, J=16.55Hz, 2H), 6.77(d, J=16.55Hz, 2H) and, 1.56 (s, H 2o); (as shown in Figure 3)
13CNMR(126MHz,CDCl 3),δ150.74,145.80,135.30,133.69,133.10,132.40,129.98,129.66,128.11,125.46,120.94,116.71.
Mass spectrum molecular ion peak is: 554.947
Concrete reaction equation is as follows:
Embodiment 4:
2,4,6-trinitro--1,3-bis-(3 '-dichlorostyrene base) benzene (R 1, R 3for hydrogen, R 2for chlorine atom) microwave synthetic:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) in 20mL methylene dichloride, drips 0 of piperidinyl-1 and carrier NaOH(3.0g with m chlorobenzaldehyde (0.59g, 4.2mmol) mixed dissolution), raw material and basic catalyst uniform loading are on carrier, under normal pressure, except desolventizing, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.89g), productive rate 86.1%.
Yellow solid, fusing point: 142-143 DEG C, IR (ν, cm -1): 3093,1628,1535,1373,1329,966.
Concrete reaction equation is as follows:
Embodiment 5:
By 1x10 -52,4 of mol/L, 6-trinitro--1,3-bis-(4 '-chloro-styrene base) benzene (R 1, R 2for hydrogen atom, R 3for chlorine) be dissolved in trichloromethane, measure its ultraviolet-visible absorption spectroscopy.(as shown in Figure 4), from scheming, can find out, this material has obvious absorption peak near 340nm, and absorption region is wider, has good optical property.
Embodiment 6:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and o-chlorobenzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip N methyl piperazine (10) and carrier NaOH(3.0g), raw material and basic catalyst uniform loading are on carrier, under normal pressure, remove desolventizing, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.80g), productive rate 81.7%.
Embodiment 7:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 4-chloro-benzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip piperidines 0.08g (0.9mmol) and carrier KOH(3.0g), raw material and basic catalyst uniform loading are on carrier, under normal pressure, remove desolventizing, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.70g), productive rate 73%.
Embodiment 8:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 4-chloro-benzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip 10 of triethylamines and carrier KOH(3.0g), raw material and basic catalyst uniform loading, on carrier, are removed desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 300W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.73g), productive rate 75%.
Embodiment 9:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and o-chlorobenzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip 10 of triethylamines and carrier KOH(3.0g), raw material and basic catalyst uniform loading, on carrier, are removed desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, by the solid transfer obtaining, to Pyrex reaction flask the uncovered microwave reactor that is placed in, under 400W power, microwave took out after 15 minutes.Reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.68g), productive rate 66%.
Comparative example 1
This compounds adopts traditional Aldol-type condensation reaction to synthesize 2 conventionally, 4,6-trinitro--1,3-diphenylethyllene benzene derivative is with 2,4,6-trinitro-m-xylene and various substituted benzaldehyde are raw material, use benzene as solvent, organic base catalytic reacts and prepares for 48 hours under reflux temperature.(seeing Org.Prep.Proced.Int.1995,27,475) but there is following shortcoming in this reaction conditions: (1) this reaction yield is low; (2) in reaction process, make solvent with benzene, and benzene is poisonous, carcinogenic, environment is unfriendly; (3) the long reaction times.
Chloride 2,4,6-trinitro--1,3-diphenylethyllene benzene derivative, the chemical structure of general formula of its compound is as follows:
Wherein, in molecular structure, 2,4,6 on the middle phenyl ring of 1,3-diphenylethyllene benzene have three nitros, and neighbour on the phenyl ring of both sides,, contraposition is connected with chlorine atom, namely R 1, R 2, R 3in have one be connected with chlorine atom other for hydrogen, or R 1, R 3be chlorine atom, other is hydrogen atom simultaneously.The type compound can be used in optical material field, as nonlinear optical organic, and photosensitizers etc. or the important intermediate as energetic material field.

Claims (10)

  1. One kind chloride 2,4,6-trinitro--1,3-diphenylethyllene benzene derivative, is characterized in that this compound structure general formula is:
    Wherein, R 1, R 2, R 3one of them is chlorine atom or R 1, R 3be chlorine atom simultaneously, R 2for hydrogen atom.
  2. One kind chloride 2,4 as claimed in claim 1,6-trinitro--1, the preparation method of 3-diphenylethyllene benzene derivative, is characterized in that comprising the following steps:
    By 2,4,6-trinitro-m-xylene and Chlorobenzaldehyde mixed dissolution, in organic solvent, add basic catalyst and carrier, raw material and basic catalyst uniform loading are on carrier, under normal pressure, except desolventizing, obtain the solid mixture of load raw material, then this solid mixture is transferred in microwave reactor, under certain output rating, react, reaction finishes to use acetone extraction product afterwards, then removes acetone and obtain crude product, and crude product obtains target product after recrystallization.
  3. 3. preparation method according to claim 2, is characterized in that: Chlorobenzaldehyde is selected o-chlorobenzaldehyde, m chlorobenzaldehyde, 4-chloro-benzaldehyde and 2,4 dichloro benzene formaldehyde.
  4. 4. preparation method according to claim 2, is characterized in that: alkaline catalysts is selected one or more in N methyl piperazine, morpholine, triethylamine, pyridine, piperidines.
  5. 5. preparation method according to claim 2, is characterized in that: the mol ratio of 2,4,6-trinitro-m-xylene and Chlorobenzaldehyde is 1:2.1, and the reaction times is 15min.
  6. 6. preparation method according to claim 2, is characterized in that: carrier is selected silica gel, NaOH, KOH, K 2cO 3in one.
  7. 7. preparation method according to claim 2, is characterized in that: the output rating of microwave is set to 300-400W.
  8. 8. synthetic method according to claim 2, is characterized in that: organic solvent is selected methylene dichloride, recrystallization solvent is selected acetone-alcohol mixed solvent.
  9. One kind as claimed in claim 1 chloride 2,4,6-trinitro--1, being applied to of 3-diphenylethyllene benzene derivative, is characterized in that the intermediate of this compounds for the synthesis of heat-resisting energetic material aspect.
  10. One kind as claimed in claim 1 chloride 2,4,6-trinitro--1, being applied to of 3-diphenylethyllene benzene derivative, is characterized in that this compounds is for luminescent device.
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CN104292876A (en) * 2014-09-12 2015-01-21 沈阳化工大学 Method for preparing direct dye yellow 11 by using microwave heating
CN104292876B (en) * 2014-09-12 2016-04-06 沈阳化工大学 Microwave heating is utilized to prepare the method for substantive dyestuff Huang 11
CN105037165A (en) * 2015-07-02 2015-11-11 江苏新淮河医药科技有限公司 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene and preparation method thereof
CN105037165B (en) * 2015-07-02 2017-03-29 江苏新淮河医药科技有限公司 1,3 two（2 bromine, 5 methoxyl-styrene）2,4,6 trinitrobenzene compounds and preparation method thereof
CN105693521A (en) * 2016-03-02 2016-06-22 南京理工大学 Bromide product of trinitro-stilbene compound and synthesis method thereof
CN107382898A (en) * 2017-07-21 2017-11-24 中国工程物理研究院化工材料研究所 A kind of energetic material and its synthetic method based on ANPZ precursor structures containing energy
CN107382898B (en) * 2017-07-21 2019-12-24 中国工程物理研究院化工材料研究所 Energetic material based on ANPZ energetic parent structure and synthetic method thereof

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