CN108409575A - The method that nitrate nitrated aromatics are realized under mechanical force - Google Patents

The method that nitrate nitrated aromatics are realized under mechanical force Download PDF

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CN108409575A
CN108409575A CN201710070685.0A CN201710070685A CN108409575A CN 108409575 A CN108409575 A CN 108409575A CN 201710070685 A CN201710070685 A CN 201710070685A CN 108409575 A CN108409575 A CN 108409575A
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nitrate
aromatic
mechanical force
preparation
nitro
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CN108409575B (en
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郭凤超
纪民尊
刘鹏
张璞
秦玉军
郭志新
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Renmin University of China
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/76—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by nitration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention discloses the methods that nitrate nitrated aromatics are realized under mechanical force.A kind of preparation method of aromatic nitro compound provided by the invention, includes the following steps：Under mechanical force, aromatic compound, through nitration reaction, obtains the aromatic nitro compound with metal nitrate or its hydrate；The mechanical force is the external force that can cause substance physically and/or chemically change of properties that machinery provides.The mechanical force can be any one of to compress, shear, impact, rub, stretch, be bent and vibrate.The invention has the advantages that：Without using any solvent, waste liquid generation is avoided；Without the use of acidic materials, reaction completes post-processing simply, to equipment without any damage；High conversion ratio and selectivity can be applied to nitrify conventional aromatic compound.

Description

The method that nitrate nitrated aromatics are realized under mechanical force
Technical field
The present invention relates to nitrate nitrification virtue is realized under the nitration method of aromatic compound more particularly to mechanical force The method of fragrant compounds of group.
Background technology
The research of nitrification aromatic rings is seen in many reports.Fragrant nitration product industrially has extremely important application, Such as manufacture dyestuff, medicine and fine chemistry industry.Under normal conditions, the nitrifying process known to us be using nitration mixture both nitric acid with it is dense Sulfuric acid mixes, at present industry nitration process or more use nitration mixture, but its disadvantage is also evident from, and has both generated a large amount of difficulties It disposes waste liquid and the reaction system has very strong corrosivity to equipment, a large amount of waste water for especially reacting generation seriously pollute environment Treatment cost is high.Also have using gas such as NO simultaneously2、N2O4、N2O5Aromatic rings is nitrified, but gas in gas nitrifying process It is no small problem that preservation, which uses,.
Aromatic rings nitrifying process is mostly liquid phase reactor at present, the use of nitrate nitrifying process is also such.
US 20070255057 elaborates to nitrify nitrogenous fragrance derivatives under the acid conditions such as sulfuric acid, acetic acid, the process The generation of the middle nitrate generated there are substrate and nitric acid with detach.A kind of mono-nitration nitrogenous aromatic compound is provided in the invention Method, while be discussed in detail synthesis 4- morpholine -2 Nitroanisoles method.
IN 191095A1 are illustrated in without using in the case of sulfuric acid, are carried nitrate using montmorillonite and are used 20-40% simultaneously Perchloric acid at -15 DEG C to reacting 0.5-24h nitrofying aromatic hydrocarbon derivatives at+100 DEG C, while nitrate being taken using known method Load and montmorillonite, while extremely can easily extract nitration product using organic reagent.
CN103086892A illustrates the method for preparing paranitrochlorobenzene using nitrogen dioxide Nitration of Chloronitrobenzene, and chlorobenzene is being catalyzed It is reacted with nitrogen dioxide in agent and oxygen atmosphere, prepares paranitrochlorobenzene, included the following steps：(1) by chlorobenzene, catalyst and Molecular sieve, stirring are allowed to uniformly mixed；(2) after being passed through nitrogen dioxide and protection gas, 12-48h is stirred to react to get the thick production of reaction Object；(3) by reacting coarse product Filtration of catalyst and molecular sieve, after standing separation goes out organic phase, use sodium bicarbonate molten successively Repeatedly washing to organic phase is in neutrality for liquid and distilled water, and nitro-chlorobenzene is isolated in vacuum distillation；(4) paranitrochlorobenzene is dried Afterwards, efficient liquid phase chromatographic analysis is carried out by internal standard of nitrobenzene, the nitration product constituent content of chlorobenzene is calculated with internal standard method.
That there are conversion ratios is low for the above method, eurytopicity is poor, the reaction time is long, the shortcomings such as cumbersome.
Invention content
The object of the present invention is to provide the method that nitrate nitrated aromatics are realized under mechanical force, this method Nitrification can be realized under conditions of no solution participates in, there is universality, it is miscellaneous for benzene derivative, polycyclic aromatic compounds and virtue Cycle compound can nitrify；There is quick, efficient, high yield and selectivity simultaneously, and environmentally friendly.
A kind of preparation method of aromatic nitro compound provided by the invention, includes the following steps：In mechanical force Under, aromatic compound, through nitration reaction, obtains the aromatic nitro compound with metal nitrate or its hydrate；It is described Mechanical force is the external force that the energy that provides of machinery can cause substance physically and/or chemically change of properties.
In above-mentioned preparation method, the aromatic nitro compound refer to one in the aromatic ring of aromatic compound or The compound that multiple hydrogen are replaced by nitro can be single nitro-aromatic compound, dinitro aromatic compound and/or more nitros Aromatic compound.
In above-mentioned preparation method, the mechanical force can be compression, shearing, impact, friction, stretch, in bending and vibration It is any.In an embodiment of the present invention, the mechanical force concretely vibratory milling.
In above-mentioned preparation method, the application frequency of the mechanical force can be>5Hz, preferably 5~50Hz, concretely 10 ~40Hz, 10Hz, 15Hz, 20Hz, 30Hz, 40Hz.In an embodiment of the present invention, the frequency of vibrator is specifically adjusted Rate.
In above-mentioned preparation method, the molar ratio of the aromatic compound and the metal nitrate or its hydrate can It is 1：(1~6), concretely 1：3、1：4.5、1：3.6、1：5、1：1、1：2.7、1：2.5、1：1.3、1：2、1：1.2.
In above-mentioned preparation method, the metal nitrate can be bismuth nitrate, chromic nitrate, copper nitrate, cobalt nitrate, nitric acid Any one of iron, lanthanum nitrate, cerous nitrate and indium nitrate；The water content of the hydrate is per 3~9mol of mol metal nitrates Water, such as 3mol, 5mol, 6mol, 9mol.Concretely five nitric hydrate bismuths, three are hydrated nitre to the hydrate of the metal nitrate Sour copper, Fe(NO3)39H2O, Chromium nitrate (Cr(NO3)3),nonahydrate, Nickelous nitrate hexahydrate or cabaltous nitrate hexahydrate.
In above-mentioned preparation method, the aromatic compound can be monocycle or poly-ring aromatic compounds, wrap among these Include their monosubstituted or polysubstituted derivative, such as halogen, alkyl (such as methyl), alkoxy (such as methoxyl group), phenyl, carbonyl Base, sulfonic group, amido, nitroso, nitro, itrile group, hydroxyl, carboxyl etc. be monosubstituted or polysubstituted derivative.The aromatic series Compound can be any one of benzene derivative, fused aromatic compounds and heteroaromatic compounds.The aromatic compound Concretely 4- methoxyl biphenyls, benzene, chlorobenzene, N, accelerine, naphthalene, anthracene, phenanthrene, pyrene, quinoline, isoquinolin or benzo pyrrole It mutters.
In above-mentioned preparation method, time of the reaction can be 10 minutes~2 hours, concretely 10 minutes, 0.5 small When, 1 hour, 1.5 hours or 2 hours.
In above-mentioned preparation method, the method further includes being extracted using organic reagent after the nitration reaction terminates The step of taking reaction product to obtain the aromatic nitro compound, the organic reagent can be arbitrarily to have polar organic examination Agent, such as dichloromethane, toluene, chloroform.
The invention has the advantages that：
1, without using any solvent, waste liquid generation is avoided.
2, it is without the use of acidic materials, reaction completes post-processing simply, to equipment without any damage.
3, high conversion ratio and selectivity can be applied to nitrify conventional aromatic compound.
Description of the drawings
Fig. 1 is the NMR spectra for the 4- methoxyl biphenyl nitro compounds being prepared in embodiment 1.
Fig. 2 is the NMR spectra that nitrobenzene is prepared in embodiment 7.
Fig. 3 is the NMR spectra for the nitro-chlorobenzene being prepared in embodiment 8.
Fig. 4 is the NMR spectra for the nitrobiphenyl that embodiment 10 is prepared.
Fig. 5 is the NMR spectra for the dinitrotoluene that embodiment 11 is prepared.
Fig. 6 is the NMR spectra for the 1,4- dimethoxy -2- nitrobenzenes that embodiment 13 is prepared.
Fig. 7 is the N that embodiment 14 is prepared, the NMR spectra of N- dimethyl benzene nitro compounds.
Fig. 8 is the NMR spectra for the nitronaphthalene that embodiment 15 is prepared.
Fig. 9 is the NMR spectra for the nitropyrene that embodiment 18 is prepared.
Specific implementation mode
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
The mechanical force applied during the reaction in following embodiments is vibratory milling (using vibrator), instead It is popular response tank to answer tank.
Reaction temperature in following embodiments carries out at normal temperatures unless otherwise specified, without additional heating.
Nitrify monocyclic compound
Embodiment 1 prepares 4- methoxyl biphenyl nitro compounds
5mg 4- methoxyl biphenyls and five nitric hydrate bismuths of 39.5mg are added in 2.5ml retort, under the conditions of 20Hz React 0.5h.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 44.7%4 '-nitro -4- first Oxygroup biphenyl and 49.3%3- nitro -4- methoxyl biphenyls (NMR spectra is shown in Fig. 1).
Embodiment 2 prepares 4- methoxyl biphenyl nitro compounds
5mg 4- methoxyl biphenyls and five nitric hydrate bismuths of 39.5mg are added in 2.5ml retort, under the conditions of 10Hz React 0.5h.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 10.6%4 '-nitro -4- first Oxygroup biphenyl, 35%3- nitro -4- methoxyl biphenyls and 54.4%4 '-nitro -4- methoxyl biphenyls.
Embodiment 3 prepares 4- methoxyl biphenyl nitro compounds
5.5mg 4- methoxyl biphenyls and 32.9mg Gerhardites are added in 2.5ml retort, in 20Hz conditions Lower reaction 0.5h.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 58.5%4 '-nitro -4- Methoxyl biphenyl and 37%3- nitro -4- methoxyl biphenyls.
Embodiment 4 prepares 4- methoxyl biphenyl nitro compounds
22mg 4- methoxyl biphenyls and five nitric hydrate bismuths of 174.8mg are added in 2.5ml retort, in 15Hz situations Lower reaction 0.5h.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 43.3%4 '-nitro -4- Methoxyl biphenyl and 37.6%3- nitro -4- methoxyl biphenyls.
Embodiment 5 prepares 4- methoxyl biphenyl nitro compounds
22mg 4- methoxyl biphenyls and 145.6mg Fe(NO3)39H2Os are added in 2.5ml retort, in 20Hz situations Lower reaction 0.5h.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 48.9%4 '-nitro -4- Methoxyl biphenyl and 33.5%3- nitro -4- methoxyl biphenyls.
Embodiment 6 prepares 4- methoxyl biphenyl nitro compounds
5mg 4- methoxyl biphenyls and 39.5mg Chromium nitrate (Cr(NO3)3),nonahydrates are added in 2.5ml retort, under the conditions of 30Hz React 0.5h.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 35.6%4 '-nitro -4- first Oxygroup biphenyl and 40%3- nitro -4- methoxyl biphenyls.
Embodiment 7 prepares nitrobenzene
Five nitric hydrate bismuth of 53.5 μ L benzene and 1.5g is added in 50ml retort, reacts 2h under the conditions of 40Hz.Reaction It completes to extract substrate from solid using dichloromethane, is detected through NMR and generate 80% nitrobenzene (NMR spectra is shown in Fig. 2).
Embodiment 8 prepares nitro-chlorobenzene
Five nitric hydrate bismuth of 60.8 μ L chlorobenzenes and 1.5g is added in 50ml retort, reacts 2h in 40Hz.Instead It should complete to extract substrate from solid using dichloromethane, be detected through NMR and generate 70%2- nitro-chlorobenzenes and 28%4- nitroxyl chlorides Benzene (NMR spectra is shown in Fig. 3).
Embodiment 9 prepares 4- methoxyl biphenyl nitro compounds
700mg 4- methoxyl biphenyls and five nitric hydrate bismuths of 1.5g are added in 50ml retort, it is anti-under the conditions of 15Hz Answer 10min.Reaction is completed to extract substrate from solid using dichloromethane, is detected through NMR and generates 49.2%4 '-nitro -4- first Oxygroup biphenyl and 50.8%3- nitro -4- methoxyl biphenyls.
Embodiment 10 prepares nitrobiphenyl
3.1mg biphenyl and five nitric hydrate bismuths of 43.6mg are added in 2.5ml retort, is reacted under the conditions of 20Hz 1.5h.Reaction terminates, and extracts reaction product using dichloromethane, is detected through NMR, generates 50.9%4- nitrobiphenyls and 40.8% 2 nitro biphenyl (NMR spectra is shown in Fig. 4).
Embodiment 11 prepares dinitrotoluene
Five nitric hydrate bismuth of 63.8 μ L toluene and 1.3g is added in 50mL retort, adds 3g anhydrous magnesium sulfates, Frequency reacts 1h under the conditions of being 20Hz.Reaction terminates, and is extracted using dichloromethane, is detected using NMR it is found that there is 49.6%4- nitre Base toluene and 31%2- nitrotoleunes generate (NMR spectra is shown in Fig. 5).
Embodiment 12 prepares nitrobiphenyl
3.1mg biphenyl and 21.7mg Gerhardites are added in 2.5ml retort, is reacted in 20Hz 1.5h.Reaction terminates, and extracts reaction product using dichloromethane, is detected through NMR, generates 60%4- nitrobiphenyls and 34.8%2- Nitrobiphenyl.
Embodiment 13 prepares 1,4- dimethoxy -2- nitrobenzenes
3.8mg Isosorbide-5-Nitraes-five nitric hydrate bismuth of dimethoxy benzene and 39.5mg is added in 2.5ml retort, in 20Hz items 0.5h is reacted under part.Reaction terminates, and extracts reaction product using dichloromethane, is detected through NMR, generates 100%1,4- dimethoxies Base -2- nitrobenzenes (NMR spectra is shown in Fig. 6).
Embodiment 14 prepares N, N- dimethyl benzene nitro compounds
3.8mg n,N-Dimethylaniline and 31.4mg Fe(NO3)39H2Os are added in 2.5ml retort, in 10Hz items 0.5h is reacted under part.Reaction terminates, and extracts reaction product using dichloromethane, is detected through NMR, generates 60%N, N- dimethyl- 4- nitrobenzenes and 40%N, N- dimethyl -2- nitrobenzenes (NMR spectra is shown in Fig. 7).
Nitrify fused ring compound
Embodiment 15 prepares nitronaphthalene
20mg naphthalenes and 80mg Fe(NO3)39H2Os are added in 2.5ml retort, reacts 1h under the conditions of 20Hz.It has reacted At using chloroform extraction.There are 91% 1- nitronaphthalenes to generate (NMR spectra is shown in Fig. 8) using known to NMR detections.
Embodiment 16 prepares nitroanthracene
30mg anthracenes and 80mg Gerhardites are added in 2.5ml retort, reacts 1h under the conditions of 15Hz.It has reacted At using chloroform extraction.There are 93% 1- nitroanthracenes to generate using known to NMR detections.
Embodiment 17 prepares nitro phenanthrene
30mg phenanthrene and 80mg Fe(NO3)39H2Os are added in 2.5ml retort, reacts 1h in 20Hz.It has reacted At using chloroform extraction.There is 94% 1- nitro phenanthrene to generate using known to NMR detections.
Embodiment 18 prepares nitropyrene
40mg pyrenes and five nitric hydrate bismuths of 80mg are added in 2.5ml retort, reacts 1h under the conditions of 20Hz.It has reacted At using chloroform extraction.There is 100% 1-nitropyrene to generate (NMR spectra is shown in Fig. 9) using known to NMR detections.
Embodiment 19 prepares nitropyrene
40mg pyrenes and 80mg Chromium nitrate (Cr(NO3)3),nonahydrates are added in 2.5ml retort, reacts 1h in 30Hz.It has reacted At using chloroform extraction.There is 100% 1-nitropyrene to generate using known to NMR detections.
Embodiment 20 prepares nitropyrene
80mg pyrenes and 240mg Fe(NO3)39H2Os are added in 50ml retort, frequency reacts 1h in the case of being 40Hz.Instead It should complete, use chloroform extraction.There is 100% 1-nitropyrene to generate using known to NMR detections.
Embodiment 21 prepares nitropyrene
20mg pyrenes and 63mg Nickelous nitrate hexahydrates are added in 2.5ml retort, frequency reacts 1h in the case of being 40Hz.Instead It should complete, use chloroform extraction.There is 100% 1-nitropyrene to generate using known to NMR detections.
Embodiment 22 prepares nitroquinoline
800mg quinoline and 2.40g cabaltous nitrate hexahydrates are added in 50ml retort, frequency is reacted in the case of being 20Hz 1h.Reaction is completed, and chloroform extraction is used.There are 100% 3- nitroquinolines to generate using known to NMR detections.
Embodiment 23 prepares nitroisoquinoline
20mg isoquinolin and 63mg Fe(NO3)39H2Os are added in 2.5ml retort, frequency is reacted in the case of being 30Hz 1h.Reaction is completed, and chloroform extraction is used.There are 80% 1- nitroisoquinolines to generate using known to NMR detections.
Embodiment 24 prepares nitro chromene
20mg chromenes and five nitric hydrate bismuths of 63mg are added in 2.5ml retort, frequency is anti-in the case of being 20Hz Answer 1h.Reaction is completed, and chloroform extraction is used.There are 70% 2- nitro chromenes to generate using known to NMR detections.
Comparative example：
Addition 1mL toluene, five nitric hydrate bismuths of 7.3g are added 40mL dichloroethanes simultaneously and are heated to back in three-necked flask Stream is filtered and is evaporated under reduced pressure after reflux for 24 hours, and it is 21% 2- nitrotoleunes and 22% 4- nitro first to measure product according to NMR Benzene.

Claims (8)

1. a kind of preparation method of aromatic nitro compound, includes the following steps：Under mechanical force, aromatic compound With metal nitrate or its hydrate through nitration reaction, the aromatic nitro compound is obtained；The mechanical force carries for machinery What is supplied can cause the external force of substance physically and/or chemically change of properties.
2. preparation method according to claim 1, it is characterised in that：The aromatic nitro compound is single nitryl aromatic Compounds of group, dinitro aromatic compound and/or more nitro-aromatic compounds.
3. preparation method according to claim 1 or 2, it is characterised in that：The mechanical force is to compress, shear, impacting, rubbing Any one of wipe, stretch, be bent and vibrate.
4. preparation method according to any one of claim 1-3, it is characterised in that：The frequency of the mechanical force is> 5Hz。
5. according to the preparation method described in any one of claim 1-4, it is characterised in that：The aromatic compound with it is described The molar ratio of metal nitrate or its hydrate is 1：(1~6).
6. preparation method according to any one of claims 1-5, it is characterised in that：The metal nitrate is nitric acid Any one of bismuth, chromic nitrate, copper nitrate, cobalt nitrate, ferric nitrate, lanthanum nitrate, cerous nitrate and indium nitrate；The hydrate contains Water is per mol metal nitrate 3~9mol water.
7. according to the preparation method described in any one of claim 1-6, it is characterised in that：The aromatic compound spreads out for benzene Any one of biology, fused aromatic compounds and heteroaromatic compounds.
8. according to the preparation method described in any one of claim 1-7, it is characterised in that：The time of the reaction is 10 minutes ~2 hours.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621095A (en) * 2022-03-03 2022-06-14 安徽东至广信农化有限公司 Clean nitrochlorobenzene production process

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1854114A (en) * 2005-04-21 2006-11-01 北京清华紫光英力化工技术有限责任公司 Use of bismuth nitrate and iron nitrate as nitrification agent in aromatic compound nitrification

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1854114A (en) * 2005-04-21 2006-11-01 北京清华紫光英力化工技术有限责任公司 Use of bismuth nitrate and iron nitrate as nitrification agent in aromatic compound nitrification

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621095A (en) * 2022-03-03 2022-06-14 安徽东至广信农化有限公司 Clean nitrochlorobenzene production process

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