CN105037165A - 1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound and preparation method thereof - Google Patents
1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound and preparation method thereof Download PDFInfo
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- CN105037165A CN105037165A CN201510380492.6A CN201510380492A CN105037165A CN 105037165 A CN105037165 A CN 105037165A CN 201510380492 A CN201510380492 A CN 201510380492A CN 105037165 A CN105037165 A CN 105037165A
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- trinitrobenzene
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- -1 1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound Chemical class 0.000 title claims abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 32
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- JHZYGPAIKZFVOS-UHFFFAOYSA-N 1-(2-bromoethenyl)-3-methoxybenzene Chemical compound COC1=CC=CC(C=CBr)=C1 JHZYGPAIKZFVOS-UHFFFAOYSA-N 0.000 claims description 14
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 238000010025 steaming Methods 0.000 claims description 10
- 239000011787 zinc oxide Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910000416 bismuth oxide Inorganic materials 0.000 claims description 3
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 claims description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 3
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000013379 physicochemical characterization Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- JSTMQHZKDFPMPS-UHFFFAOYSA-N 2,4-bis[2-(2-bromo-5-methoxyphenyl)ethenyl]-1,3,5-trinitrobenzene Chemical compound BrC1=C(C=CC2=C(C(=C(C=C2[N+](=O)[O-])[N+](=O)[O-])C=CC2=C(C=CC(=C2)OC)Br)[N+](=O)[O-])C=C(C=C1)OC JSTMQHZKDFPMPS-UHFFFAOYSA-N 0.000 abstract 2
- CECJKTQRYSIMMJ-UHFFFAOYSA-N 2,4-bis[2-(3-methoxyphenyl)ethenyl]-1,3,5-trinitrobenzene Chemical compound O(C)C=1C=C(C=CC2=C(C(=C(C=C2[N+](=O)[O-])[N+](=O)[O-])C=CC2=CC(=CC=C2)OC)[N+](=O)[O-])C=CC=1 CECJKTQRYSIMMJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003779 heat-resistant material Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000008204 material by function Substances 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000002390 rotary evaporation Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 244000124209 Crocus sativus Species 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 235000015655 Crocus sativus Nutrition 0.000 description 16
- 235000013974 saffron Nutrition 0.000 description 16
- 239000004248 saffron Substances 0.000 description 16
- 239000002808 molecular sieve Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GGGVOOMKPJYWDF-UHFFFAOYSA-N 2,4,6-trinitroxylene Chemical group CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C)=C1[N+]([O-])=O GGGVOOMKPJYWDF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a 1, 3-bis (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound and a preparation method thereof, wherein 1, 3-bis (3-methoxystyryl) -2, 4, 6-trinitrobenzene, liquid bromine and a catalyst are added into a reactor, dichloromethane is used as a solvent, after the reaction is finished at normal temperature, the filtration is carried out, saturated sodium carbonate solution is used for neutralizing the filtrate, dichloromethane is used for extraction, rotary evaporation is carried out, and drying is carried out to obtain 1, 3-bis (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene. The 1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene of the invention has a bromine atom on each benzene ring at the periphery and good symmetry, and the central benzene ring is connected with the other two benzene rings by two conjugated double bonds, thereby greatly improving the stability of the compound and being used for functional materials such as medicines, insecticides, heat-resistant materials and the like.
Description
Technical field
The present invention relates to a kind of 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzene compound and preparation methods, belong to fire retardant, sterilant and medicine intermediate.
Background technology
The double bond existed in diphenylethylene compounds structure and the conjugative effect of phenyl ring, make this compound chemistry Nature comparison stablize.If introduce multiple nitro on phenyl ring, make it more stable, and then brominating conditions become harsher.Up to now, very Polybrominated method has been developed, such as NBS H
2sO
4tFA, DBUHBr
3, Br
2lewisacids, KBr/BTPPMS, ZrBr
4/ diaziene, IQBC and [BMPy] Br
3etc..Although these methods are widely used, they still have several more significant shortcoming: 1, applicable compound is more limited; 2, side chain side reaction and excessive bromination is had; 3, bromination result is single; 4, regioselectivity is poor, causes the waste of raw material and produces a large amount of waste liquid.Along with bromination process ground is flourish, key is development green synthesis method, therefore, finds a kind of bromination catalyst of Novel clean to be one of effective ways overcome the above problems.And nowadays, existing catalyzer is zeolitic catalyst, clay class catalyzer, ion-exchange resin catalyst, immobilized liquid acid catalyst, metal oxide and metal salt catalyst, heteropolyacid catalyst and solid super acid catalyst.Wherein zeolitic catalyst not only can improve the regioselectivity of bromination, and reduces pollutant emission, and work-ing life is longer simultaneously, reduces industrial cost.But in zeolitic catalyst, H-Beta type zeolite catalysis effect is better, selectivity good and long service life.Based on this, we have selected H-Beta type zeolite bromination 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzenes.Bromine-containing compound is important industrial chemicals, and in each department of national economy widespread use, and along with the development of science and technology, the quickening of research and development speed, the novelty teabag of bromine-containing compound is in continuous expansion.
Summary of the invention
The object of the invention is to: provide a kind of 1,3-bis-(bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzene compound and preparation method, this compound not only symmetry is good, and stable, potentially can be applied to fire retardant, sterilant and medicine intermediate etc.
Technical solution of the present invention is: this compound to have structure as follows:
This compound physicochemical characterization is as follows: IR (KBr, ν, cm
-1): 3095,1634,1590,1539,1332,970; M.p.211.2-213.2 DEG C;
1hNMR (300MHz, CDCl
3), δ 8.85 (s, 1H), 7.52 (d,
j=8.7Hz, 2H), 7.18-7.15 (m, 6H), 6.86-6.82 (m, 2H), 3.88 (s, 6H);
13cNMR (75MHz, DMSO-d
6), δ 159.36,147.12,135.50,134.68,134.26,130.58,123.35,121.66,117.85,114.57,112.95,56.04.
Wherein, 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2, the preparation method of 4,6-trinitrobenzene compound comprises the following steps: by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene, bromine, catalyzer join in reactor, make solvent with methylene dichloride, react at normal temperatures; After having reacted, filter, use saturated sodium carbonate solution neutralization filtrate, dichloromethane extraction, revolve steaming, dry and obtain 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzenes.
Wherein, described catalyzer select in H-Beta/ zinc oxide, H-Beta/ bismuth oxide, H-Beta/ ferric oxide, H-Beta/ titanium oxide one of.
Wherein, described 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzenes are 1 ~ 2 with the ratio of the amount of substance of bromine.
Wherein, described catalyst levels is 10% of 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene amount of substance.
Compared with prior art, advantage of the present invention is: (1) has synthesized a kind of 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzenes; (2) from structure, containing a bromine atoms on the peripheral each phenyl ring of this compound, center phenyl ring is connected with conjugated double bond respectively with other two phenyl ring, and symmetry is good; (3) from application, this compound can be used for fire retardant, sterilant and medicine intermediate etc.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, the present invention is described in further detail.
Fig. 1 is the hydrogen nuclear magnetic resonance collection of illustrative plates of embodiment 1 product 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzenes, and X-coordinate is chemical shift.
Fig. 2 is the nuclear magnetic resonance of carbon collection of illustrative plates of embodiment 1 product 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzenes, and X-coordinate is chemical shift.
Embodiment
Further illustrate technical solution of the present invention below in conjunction with embodiment, make the present invention of those skilled in the art comprehend, and these embodiments can not be interpreted as it is restriction to technical scheme.
the preparation of raw material 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzenes:2,4,6-trinitro-m-xylene (0.24g), m-methoxybenzaldehyde (0.27g), piperidines (1mL), benzene (40mL) are joined in reactor, reflux at 100 DEG C, reaction 10h, boils off partial solvent, filter, with benzene and ethanol successively washing, dry to obtain 0.4g safran solid.
embodiment 1:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzenes (0.48g), bromine (0.32g), H-Beta molecular sieve (0.05g), zinc oxide (0.05g) and methylene dichloride (10mL) add in reactor, 24h is reacted under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.61g, recrystallization is carried out with acetone and ethanol, obtain saffron straight product 0.59g, fusing point is 211.2-213.2 DEG C, and productive rate is 96.7%.
IR(KBr,ν,cm
-1):3095,1634,1590,1539,1332,970;
1HNMR(300MHz,CDCl
3),δ8.85(s,1H),7.52(d,
J=8.7Hz,2H),7.18-7.15(m,6H),6.86-6.82(m,2H),3.88(s,6H);
13CNMR(75MHz,DMSO-d
6),δ159.36,147.12,135.50,134.68,134.26,130.58,123.35,121.66,117.85,114.57,112.95,56.04。
embodiment 2:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.32g), H-Beta molecular sieve (0.1g), zinc oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.61g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.55g, productive rate is 90.2%.
embodiment 3:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.32g), H-Beta molecular sieve (0.02g), zinc oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.53g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.42g, productive rate is 79.2%.
embodiment 4:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.24g), H-Beta molecular sieve (0.05g), zinc oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.36g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.17g, productive rate is 47.2%.
embodiment 5:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.16g), H-Beta molecular sieve (0.05g), zinc oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.34g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.16g, productive rate is 47.1%.
embodiment 6:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.32g), H-Beta molecular sieve (0.05g), bismuth oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.6g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.56g, productive rate is 93.3%.
embodiment 7:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.32g), H-Beta molecular sieve (0.05g), titanium oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.58g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.45g, productive rate is 77.6%.
embodiment 8:by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene (0.48g), bromine (0.32g), H-Beta molecular sieve (0.05g), ferric oxide (0.05g) and methylene dichloride (10mL) add in reactor, react 24h under normal temperature, filter, extraction, revolves steaming and obtains saffron thick product 0.55g, carry out recrystallization with acetone and ethanol, obtain saffron straight product 0.23g, productive rate is 41.8%.
Involved in the present invention 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4, containing a bromine atoms on each phenyl ring in periphery of 6-trinitrobenzene, symmetry is good, center phenyl ring is connected with two conjugated double bonds with other two phenyl ring, substantially increases its stability, can be used for fire retardant, sterilant and medicine intermediate etc.
Claims (5)
1.3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzene compounds, it is characterized in that this compound to have structure as follows:
This compound physicochemical characterization is as follows: IR (KBr, ν, cm
-1): 3095,1634,1590,1539,1332,970; M.p.211.2-213.2 DEG C;
1hNMR (300MHz, CDCl
3), δ 8.85 (s, 1H), 7.52 (d,
j=8.7Hz, 2H), 7.18-7.15 (m, 6H), 6.86-6.82 (m, 2H), 3.88 (s, 6H);
13cNMR (75MHz, DMSO-d
6), δ 159.36,147.12,135.50,134.68,134.26,130.58,123.35,121.66,117.85,114.57,112.95,56.04.
2.1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4, the preparation method of 6-trinitrobenzene compound, is characterized in that the preparation method of this compound comprises the following steps: by 1,3-bis-(3-methoxyl-styrene)-2,4,6-trinitrobenzene, bromine, catalyzer join in reactor, make solvent with methylene dichloride, react at normal temperatures; After having reacted, filter, use saturated sodium carbonate solution neutralization filtrate, dichloromethane extraction, revolve steaming, dry and obtain 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4,6-trinitrobenzenes.
3. according to claim 21,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2, the preparation method of 4,6-trinitrobenzene compound, is characterized in that: described catalyzer one of to be selected in H-Beta/ zinc oxide, H-Beta/ bismuth oxide, H-Beta/ ferric oxide, H-Beta/ titanium oxide.
4. 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4 according to claim 2, the preparation method of 6-trinitrobenzene compound, is characterized in that: 1,3-bis-described (3-methoxyl-styrene)-2,4,6-trinitrobenzene is 1 ~ 2 with the ratio of the amount of substance of bromine.
5. 1,3-bis-(the bromo-5-methoxyl-styrene of 2-)-2,4 according to Claims 2 or 3, the preparation method of 6-trinitrobenzene compound, is characterized in that: described catalyst levels is 1,3-bis-(3-methoxyl-styrene)-2,10% of 4,6-trinitrobenzene amount of substance.
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| CN105693521A (en) * | 2016-03-02 | 2016-06-22 | 南京理工大学 | Bromination product of trinitro-stilbene compound and synthesis method thereof |
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| CN104016869A (en) * | 2014-05-16 | 2014-09-03 | 南京理工大学 | 2,4,6-trinitro-1,3-di(2',4',6'-trinitro-3'-hydroxystyryl)benzene, synthetic method and applciation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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