CN102276475A - Method for synthesizing 1,5-dinitronaphthalene and 1,8-dinitronaphthalene - Google Patents
Method for synthesizing 1,5-dinitronaphthalene and 1,8-dinitronaphthalene Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 45
- ZUTCJXFCHHDFJS-UHFFFAOYSA-N 1,5-dinitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1[N+]([O-])=O ZUTCJXFCHHDFJS-UHFFFAOYSA-N 0.000 title claims abstract description 27
- AVCSMMMOCOTIHF-UHFFFAOYSA-N 1,8-dinitronaphthalene Chemical compound C1=CC([N+]([O-])=O)=C2C([N+](=O)[O-])=CC=CC2=C1 AVCSMMMOCOTIHF-UHFFFAOYSA-N 0.000 title abstract description 8
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000007789 gas Substances 0.000 claims abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical compound O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910021536 Zeolite Inorganic materials 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 6
- 239000010457 zeolite Substances 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 15
- 239000002253 acid Substances 0.000 abstract description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 8
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 8
- XNKFCDGEFCOQOM-UHFFFAOYSA-N 1,2-dinitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C21 XNKFCDGEFCOQOM-UHFFFAOYSA-N 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006396 nitration reaction Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
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- 239000003550 marker Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
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- 230000000802 nitrating effect Effects 0.000 description 4
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- 229910001220 stainless steel Inorganic materials 0.000 description 2
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- XFYQEBBUVNLYBR-UHFFFAOYSA-N 12-phthaloperinone Chemical compound C1=CC(N2C(=O)C=3C(=CC=CC=3)C2=N2)=C3C2=CC=CC3=C1 XFYQEBBUVNLYBR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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- 238000005265 energy consumption Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000001546 nitrifying effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing 1,5-dinitronaphthalene and 1,8-dinitronaphthalene. Normally, industrial production of dinitronaphthalene adopts naphthalene or nitronaphthalene as a raw material and a traditional nitric acid-sulfuric acid mixed method for nitration. The method does not adopt nitric acid and sulfuric acid but adopts nitrogen dioxide as a nitration reagent and 1-nitronaphthalene as a basic material to synthesize 1,5-dinitronaphthalene and 1,8-dinitronaphthalene. The method comprises the following steps that A, 1-nitronaphthalene and nitrogen dioxide are added into a reactor; B, pressure of the reactor is set in a range of normal pressure to 16 MPa; C, a temperature of the reactor is set in a range of -50 to 300 DEG C, and D the mixture obtained by the step A reacts fully. In the invention, oxygen containing gas, a catalyst and a solvent can be added into the reaction system to improve a reaction yield and selectivity. The method has the advantages of mild reaction condition, good selectivity, high yield, no production of waste acids, and good applicability for engineering use.
Description
Technical field
The present invention relates to a kind of synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene, especially a kind of to be with the 1-nitro-naphthalene that raw material is used nitrogen peroxide nitrated synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene.
Background technology
1,5-dinitronaphthalene and 1,8-dinitronaphthalene are very important chemical intermediates, are widely used in dyestuff, pigment and high energy material etc. synthetic.1, the 5-dinitronaphthalene is 1 simultaneously, the precursor of 5-naphthalene diisocyanate, 1, the 5-naphthalene diisocyanate has high melt point, by its synthetic urethane have that hardness height, rebound resilience are good, advantage such as good heat resistance, dynamic property excellence, wear resistance are good, can be used for that conventional polyurethanes can not meet the demands or the workplace of early failure, as environment such as high temperature and heavy wool fat, therefore be used as the raw material of synthetic senior urethane more.1, the 8-dinitronaphthalene also is 1, the precursor of 8-diaminonaphthalene, and it is mainly used in the production solvent dye, as C. I. solvent of red 135, C.I. solvent orange 60 etc.
The industrial production dinitronaphthalene mainly still adopts traditional nitric acid sulfuric acid nitration mixture method to carry out nitrated both at home and abroad now.With naphthalene or mononitronaphthalene is raw material, can synthesize by the nitration reaction of itself and nitric acid sulfuric acid mixture and rough contain 1,5-dinitronaphthalene, 1, the mixture of 8-dinitronaphthalene, 1-nitro-naphthalene and partial oxidation products.But, in synthetic rough dinitronaphthalene mixture process, use nitric acid vitriolic mixture just must set up the unit facility that is harmful to environment and handle acid and reclaim nitric acid and sulfuric acid.
There are some documents to relate to and improve 1, the output of 5-dinitronaphthalene by introducing reagent and solvent in nitrating mixture.But, separate and the cost that reclaims very expensive, and all use strong acid nitrifying method such as nitric acid.The method that adopts the thick dinitronaphthalene mixture of nitric acid production has been described among the US3998893, and using mononitronaphthalene in this method is main raw material, uses the nitric acid nitrating method equally, synthetic dinitronaphthalene in the presence of sulfuric acid.It is two nitrated that CN1636963A uses single nitric acid that naphthalene is carried out, and method has been avoided the drawback in the above-mentioned document in this patent, but the amount of nitric acid and naphthalene than the stoichiometric relation that surpasses far away, same reaction occurs in the strong acidic environment medium.
Along with the development of environmental economy, the shortcoming of aforesaid method more and more shows, and mainly shows as: (1) Atom economy is not high; (2) reaction preference is poor, forms a large amount of organic by-products refuses, and environmental pollution is serious; (3) energy consumption is big, and a large amount of sour gas and inorganic strong spent acid need to handle; (4) strong acid environment is big to equipment corrosion, facility investment expense height; (5) the oxidation side reaction easily takes place in strong acid environment, sharply heat release, poor safety performance.In view of the demand of dinitronaphthalene with increasing, along with the development of environmental economy, traditional production method of dinitronaphthalene does not have Sustainable development, inevitablely be replaced by the more friendly method of environment.
Summary of the invention
The invention provides a kind of nitric acid sulfuric acid that do not use, use nitrogen peroxide and make nitrating agent, is basic raw material with the 1-nitro-naphthalene, synthesizes 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene.The inventive method reaction conditions gentleness, selectivity is good, the yield height, no spent acid is suitable for through engineering approaches to be used.
Can realize by following scheme for achieving the above object, a kind of synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene may further comprise the steps:
A, 1-nitro-naphthalene, nitrogen peroxide are added in the reactor;
B, reactor pressure is set at normal pressure to 16 MPa;
C, temperature of reactor is set at-50 ℃ to 300 ℃;
D, fully reaction.
The better technical scheme that realizes above-mentioned purpose is, reactor pressure is a normal pressure, and temperature of reactor is a room temperature.
The better technical scheme that realizes above-mentioned purpose is also to be included in and to feed the oxygen-containing gas step in the reactor.Allow be reflected in the oxygen atmosphere and carry out, oxygen-containing gas can be pure oxygen or air etc., preferred pure oxygen.
The better technical scheme that realizes above-mentioned purpose is further comprising the steps of: add catalyzer in reactor, described catalyzer is a zeolite [molecular sieve, as ZSM type, SAPO type, β type, Y type etc., and wherein preferred ZSM-11 or SAPO-34 catalyzer.Use catalyzer can improve speed of response, productive rate and selectivity.
The better technical scheme that realizes above-mentioned purpose is, also is included in to add solvent in the reactor, and described solvent is selected methylene dichloride, 1 for use, 2-ethylene dichloride, 1,1-ethylene dichloride, 1, one or more mixture in 2-propylene dichloride, acetonitrile, the propionitrile.Wherein preferred methylene dichloride and acetonitrile.
The better technical scheme that realizes above-mentioned purpose is, further comprising the steps of: as in reactor, to feed oxygen-containing gas, add catalyzer, add solvent, described catalyzer is a zeolite [molecular sieve, as ZSM type, SAPO type, β type, Y type etc., wherein preferred ZSM-11 and SAPO-34 catalyzer, described solvent is a methylene dichloride, 1,2-ethylene dichloride, 1,1-ethylene dichloride, 1, one or more mixtures in 2-propylene dichloride, acetonitrile, the propionitrile.
The better technical scheme that realizes above-mentioned purpose is, reactor pressure is a normal pressure, and temperature of reactor is a room temperature, and oxygen-containing gas is a pure oxygen, preferred ZSM-11 of catalyzer and SAPO-34, preferred methylene dichloride of solvent and acetonitrile.
The inventive method has been compared significant advantage with traditional technology.Principal feature has: it is nitrating agent that (1) novel method is used nitrogen peroxide, replaces traditional nitric acid sulfuric acid mixed acid nitrification agent, has not only improved the atom utilization of reaction, and has improved the spatter property of industrial building-up reactions, has reduced environmental pollution.(2) the inventive method can be controlled product selectivity by changing reaction solvent.When solvent is methylene dichloride, 1, the selectivity of 8-dinitronaphthalene is higher than 1, the 5-dinitronaphthalene, and when using acetonitrile as solvent, 1, the selectivity of 5-dinitronaphthalene is higher than 1, the 8-dinitronaphthalene.(3) the inventive method also can be used the selectivity of zeolite molecular sieve as catalyzer raising nitration reaction productive rate and reaction and reaction product, the renewable use of zeolite molecular sieve.(4) the inventive method does not have the spent acid processing and does not have strong acid corrodibility, and energy-saving and emission-reduction are safe.(5) the inventive method can be chosen under normal temperature, the normal pressure and finish reaction.Reaction can reduce the requirement to conversion unit under normal temperature, normal pressure, reduces conversion unit manufacturing cost and reaction process cost, improves reaction safety.(6) the inventive method provides a kind of acid labile compound to carry out nitrated method, and this technology can be used for the nitrated of many aromatics simultaneously, even also can be nitrated to the aromatics that contains a plurality of deactivating groups.
Reactor can use flask, stainless steel pressure container in the laboratory, can use tank reactor or tubular reactor etc. during industrial production.
Typical denitrification step is as follows: with organic solvent dissolution 1-nitro-naphthalene, add proper catalyst again, feed metering nitrogen peroxide and oxygen, stirring reaction under normal temperature, normal pressure.After reaction finished, mixture filtered with glass funnel, and the elimination catalyzer adopts 5% sodium hydrogen carbonate solution and water washing to neutral in succession.Telling organic phase, is that interior mark carries out efficient liquid phase chromatographic analysis with oil of mirbane, calculates the nitration product component concentration of 1-nitro-naphthalene with marker method.
Embodiment
Coming process in detail with specific embodiment below, is that raw material and nitrogen peroxide reaction synthesize 1 with the 1-nitro-naphthalene promptly, 5-dinitronaphthalene and 1, and the method for 8-dinitronaphthalene, example is not represented the invention scope of restriction this patent.
Embodiment 1
In 50 mL there-necked flasks, add 0.18 g 1-nitro-naphthalene, 5 mL acetonitriles, 0.10 g HZSM-11,2.0 mL nitrogen peroxide, magnetic agitation in the oxygen atmosphere was at room temperature reacted 7 hours.After reaction times reaches, use the deionized water termination reaction.Mixture filters with glass funnel, the elimination catalyzer.The filtrate standing separation goes out organic phase.The sodium bicarbonate aqueous solution of getting 5 mL 5% washs three times, is washed with distilled water to organic phase again for neutral, rotary evaporation in vacuo.With oil of mirbane is that interior mark carries out efficient liquid phase chromatographic analysis, calculates the component concentration of each isomer of nitrated back of 1-nitro-naphthalene with marker method.1,5-dinitronaphthalene and 1, the quality of 8-dinitronaphthalene is 0.23 g, productive rate is 79%, wherein 1,5-dinitronaphthalene quality is 0.16 g, massfraction is 68%; 1,8-dinitronaphthalene quality is 0.07 g, and massfraction is 32%.
Keep other conditions constant, change the temperature of above-mentioned reaction, carry out under-50 ℃ ,-20 ℃, 0 ℃, 50 ℃, 100 ℃, 200 ℃, 300 ℃ temperature respectively, temperature rising speed of response is accelerated.
Embodiment 2
In 50 mL there-necked flasks, add 0.20 g 1-nitro-naphthalene, 5 mL acetonitriles, 0.11 g SAPO-34,2.0 mL nitrogen peroxide, magnetic agitation in the oxygen atmosphere was 0 ℃ of reaction 7 hours.After reaction times reaches, use the deionized water termination reaction.Mixture filters with glass funnel, the elimination catalyzer.The filtrate standing separation goes out organic phase.The sodium bicarbonate aqueous solution of getting 5 mL 5% washs three times, is washed with distilled water to organic phase again for neutral, rotary evaporation in vacuo.With oil of mirbane is that interior mark carries out efficient liquid phase chromatographic analysis, calculates the component concentration of each isomer of nitrated back of 1-nitro-naphthalene with marker method.1,5-dinitronaphthalene and 1, the quality of 8-dinitronaphthalene is 0.21g, productive rate is 85%, wherein 1,5-dinitronaphthalene quality is 0.15g, massfraction is 72%; 1,8-dinitronaphthalene quality is 0.06 g, and massfraction is 28%.
Keep other conditions constant, change the temperature of above-mentioned reaction, carry out under-50 ℃ ,-20 ℃, 25 ℃, 50 ℃, 100 ℃, 200 ℃, 300 ℃ temperature respectively, temperature rising speed of response is accelerated.
Embodiment 3
In 50 mL there-necked flasks, add 0.20 g 1-nitro-naphthalene, 5 mL acetonitriles, 0.20 g HY, 2.0 mL nitrogen peroxide, magnetic agitation in the oxygen atmosphere was 15 ℃ of reactions 7 hours.After reaction times reaches, use the deionized water termination reaction.Mixture filters with glass funnel, the elimination catalyzer.The filtrate standing separation goes out organic phase.The sodium bicarbonate aqueous solution of getting 5 mL 5% washs three times, is washed with distilled water to organic phase again for neutral, rotary evaporation in vacuo.With oil of mirbane is that interior mark carries out efficient liquid phase chromatographic analysis, calculates the component concentration of each isomer of nitrated back of 1-nitro-naphthalene with marker method.1,5-dinitronaphthalene and 1, the quality of 8-dinitronaphthalene is 0.17 g, productive rate is 67%.Wherein 1,5-dinitronaphthalene quality is 0.11 g, and massfraction is 66%; 1,8-dinitronaphthalene quality is 0.06 g, and massfraction is 34%.
Above-mentioned reaction can also be carried out under-50 ,-20,0,50,100,200,300 ℃ of temperature.
Embodiment 4
In 10 mL stainless steel pressure containers, add 0.20 g 1-nitro-naphthalene, 5 mL methylene dichloride, 2.0 mL nitrogen peroxide, magnetic agitation in the air atmosphere, reaction is 11 hours under 80 ℃ of temperature and pressure 5.0 MPa.After reaction times reaches, use the deionized water termination reaction.Mixture filters with glass funnel, the elimination catalyzer.The filtrate standing separation goes out organic phase.The sodium bicarbonate aqueous solution of getting 5 mL5% washs three times, is washed with distilled water to organic phase again for neutral, rotary evaporation in vacuo.With oil of mirbane is that interior mark carries out efficient liquid phase chromatographic analysis, calculates the component concentration of each isomer of nitrated back of 1-nitro-naphthalene with marker method.1,5-dinitronaphthalene and 1, the quality of 8-dinitronaphthalene is 0.15 g, productive rate is 61%.Wherein 1,5-dinitronaphthalene quality is 0.07 g, and massfraction is 47%; 1,8-dinitronaphthalene quality is 0.08 g, and massfraction is 53%.
Other conditions are constant, change reaction pressure, carry out under normal pressure, 1.0,5.0,10.0,12.0,16.0 MPa pressure respectively.Improve reaction pressure, can improve speed of response.
Claims (9)
1. one kind is synthesized 1,5-dinitronaphthalene and 1, and the method for 8-dinitronaphthalene is characterized in that may further comprise the steps:
A, 1-nitro-naphthalene, nitrogen peroxide are added in the reactor;
B, reactor pressure is set at normal pressure to 16MPa;
C, temperature of reactor is set at-50 to 300 ℃;
D, fully reaction.
2. according to claim 1 a kind of synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene is characterized in that: described reactor pressure is a normal pressure, described temperature of reactor is a room temperature.
3. according to claim 1 synthetic 1,5-dinitronaphthalene and 1, the method that the 8-dinitronaphthalene is high is characterized in that further comprising the steps of: feed oxygen-containing gas in reactor.
4. according to claim 1 a kind of synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene is characterized in that further comprising the steps of: add catalyzer in reactor, described catalyzer is a zeolite [molecular sieve.
5. according to claim 4 a kind of synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene is characterized in that: described catalyzer is ZSM-11 and SAPO-34.
6. according to claim 1 synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene, it is characterized in that: add solvent in reactor, described solvent is a methylene dichloride, 1,2-ethylene dichloride, 1,1-ethylene dichloride, 1,2-propylene dichloride, acetonitrile, propionitrile.
7. according to claim 6 synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene is characterized in that: described solvent is methylene dichloride and acetonitrile.
8. according to claim 1 synthetic 1,5-dinitronaphthalene and 1, the method of 8-dinitronaphthalene is characterized in that further comprising the steps of: feed oxygen-containing gas in reactor, add catalyzer, add solvent, described catalyzer is a zeolite [molecular sieve, and described solvent is a methylene dichloride, 1,2-ethylene dichloride, 1,1-ethylene dichloride, 1,2-propylene dichloride, acetonitrile, propionitrile.
9. according to claim 8 synthetic 1,5-dinitronaphthalene and 1, the method for 8-dinitronaphthalene, it is characterized in that: reactor pressure is a normal pressure, and temperature of reactor is a room temperature, and oxygen-containing gas is a pure oxygen, catalyzer is ZSM-11 and SAPO-34, methylene chloride and acetonitrile.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102827007A (en) * | 2012-09-21 | 2012-12-19 | 安徽淮化股份有限公司 | Preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene |
| CN102850225A (en) * | 2012-09-21 | 2013-01-02 | 安徽淮化股份有限公司 | Method for synthesizing alpha-nitronaphthalene and beta-nitronaphthalene |
| CN103086892A (en) * | 2012-11-22 | 2013-05-08 | 安徽淮化股份有限公司 | Method for preparing p-nitrochlorobenzene by nitrifying chlorobenzene by using nitrogen dioxide |
| CN107325012A (en) * | 2017-08-04 | 2017-11-07 | 连云港市工业投资集团有限公司 | Nitrogen dioxide nitrifies the method that 4 (dimethylamino) benzaldehydes prepare 3 nitro 4 (dimethylamino) benzaldehydes |
| CN114805079A (en) * | 2022-04-28 | 2022-07-29 | 宁夏瑞泰科技股份有限公司 | Method for continuously preparing dinitronaphthalene |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102827007A (en) * | 2012-09-21 | 2012-12-19 | 安徽淮化股份有限公司 | Preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene |
| CN102850225A (en) * | 2012-09-21 | 2013-01-02 | 安徽淮化股份有限公司 | Method for synthesizing alpha-nitronaphthalene and beta-nitronaphthalene |
| CN102850225B (en) * | 2012-09-21 | 2014-07-16 | 安徽淮化股份有限公司 | Method for synthesizing alpha-nitronaphthalene and beta-nitronaphthalene |
| CN103086892A (en) * | 2012-11-22 | 2013-05-08 | 安徽淮化股份有限公司 | Method for preparing p-nitrochlorobenzene by nitrifying chlorobenzene by using nitrogen dioxide |
| CN107325012A (en) * | 2017-08-04 | 2017-11-07 | 连云港市工业投资集团有限公司 | Nitrogen dioxide nitrifies the method that 4 (dimethylamino) benzaldehydes prepare 3 nitro 4 (dimethylamino) benzaldehydes |
| CN114805079A (en) * | 2022-04-28 | 2022-07-29 | 宁夏瑞泰科技股份有限公司 | Method for continuously preparing dinitronaphthalene |
| CN114805079B (en) * | 2022-04-28 | 2024-07-05 | 宁夏瑞泰科技股份有限公司 | Method for continuously preparing dinitronaphthalene |
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