CN105439867A - A preparing method of 2-nitrobenzaldehyde - Google Patents
A preparing method of 2-nitrobenzaldehyde Download PDFInfo
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Abstract
The invention discloses a preparing method of 2-nitrobenzaldehyde. 2-nitrotoluene is adopted as a raw material and is brominated with bromine under catalytic function of azo-bis alkyl nitrile to generate 2-nitrobenzyl bromide and hydrogen bromide. The 2-nitrobenzyl bromide is hydrolyzed under catalytic function of an aqueous carbonate solution to generate 2-nitrobenzyl alcohol. The 2-nitrobenzyl alcohol is oxidized with hydrogen peroxide under catalytic function of sodium hydroxide to generate the objective compound, namely the 2-nitrobenzaldehyde. A hydrogen peroxide oxidation manner is adopted by the method, thus improving cleanliness of industrial preparation reactions, and reducing environment pollution. Oxidation is catalyzed by adopting the inorganic solid alkali catalyst and no metal organic complex catalyst is used, thus improving reaction stability and greatly reducing the cost of industrial preparation. An azo-bis alkyl nitrile solid catalyst in place of a peroxydicarbonate liquid catalyst is adopted to catalyze the bromination, thus improving reaction operation safety of industrial preparation. The method increases the product yield. The yield of the method is increased by about 5% than that of traditional industrial methods at present. The total yield can reach 77% and product purity is higher than 99%.
Description
Technical field
The present invention relates to a kind of preparation method of known compound, is exactly a kind of industrial clean method for preparing of Ortho Nitro Benzaldehyde.
Background technology
Ortho Nitro Benzaldehyde is micro-yellow solid, and fusing point 41-43 DEG C is water insoluble, is soluble in the organic solvents such as alcohol, ether, aromatic hydrocarbons, halohydrocarbon, ester.Ortho Nitro Benzaldehyde molecular formula is C
7h
5nO
3, relative molecular mass is 151.1.Ortho Nitro Benzaldehyde chemical structural formula is:
Ortho Nitro Benzaldehyde is the important pharmaceutical intermediate organic functional material of a class, mainly prevents and treats hypertension and cardiovascular disease medicine as preparing nifedipine etc., and to eliminate the phlegm anti-inflammation drugs as preparing Ambroxol etc.Ortho Nitro Benzaldehyde is also the important source material of synthesizing new plant growth regulator ' Inshuzhi ', and for the synthesis of series product such as ortho-nitrophenyl vinyl and o-nitrocinnamic acid classes.Ortho Nitro Benzaldehyde also can be used as synthesising racemation four porphyrin, and this material can be made abzyme to substitute with halogen enzyme.Therefore, Ortho Nitro Benzaldehyde high selectivity has environmental economy social benefit.
The existing preparation method of Ortho Nitro Benzaldehyde has multiple, according to the difference of basic raw material, its synthetic method mainly contains: be Material synthesis with Ortho Nitro Toluene, be Material synthesis with o-nitroethylbenzene, take toluene as Material synthesis, with ortho-nitrophenyl formyl chloride for Material synthesis, be most widely used with Ortho Nitro Toluene in raw material many above.
(1) taking Ortho Nitro Toluene as raw material, in diacetyl oxide medium, is oxygenant with chromic oxide, dichromate or potassium permanganate, oxidized side chain synthesis Ortho Nitro Benzaldehyde.This method reaction preference is poor, and form by product o-Carboxynitrobenzene, productive rate is low, and produces a large amount of unmanageable acid waste water containing heavy metallic salt, and environmental pollution is serious.
(2) take toluene as raw material, produce benzyl chloride through superchlorination, obtain target product through nitrated generation nitrobenzyl chloride, further hydrolysis and oxidation again.This method needs to apply chlorine, and benzyl chloride has lacrimation; The mixture of second step nitration reaction application nitric acid and Niobium Pentxoxide solid super-strong acid is as nitrating agent, ortho-nitration poor selectivity, but still form adjacent nitro benzyl chloride, a nitro benzyl chloride, p-nitrobenzyl chloride three kinds of isomer, separation difficulty, have strong lacrimation equally, metal oxide is difficult to regeneration.
(3) take Ortho Nitro Toluene as raw material, adjacent nitro bromobenzyl is formed by reacting with bromine, nitro alcohol is formed again through sodium carbonate catalytic hydrolysis, further through a metal-organic complex oxygen catalytic oxidation synthesis Ortho Nitro Benzaldehyde, although significantly improve reaction preference, improve productive rate, but the organo-peroxide liquid catalyst of bromination reaction operation, its industrial application poor heat stability; The a metal-organic complex catalyzer that 3rd step oxidizing reaction operation uses is difficult to regeneration, and dioxygen oxidation is liquid phase reaction system, need to react under certain pressure condition, therefore, cause production cost and industrial operation etc. conveniently not to have clear superiority.
Summary of the invention
The object of the present invention is to provide that a kind of reaction conditions is gentle, selectivity is good, yield is high, and be suitable for industrialization low cost, cleaning method that Ortho Nitro Toluene aldehyde is prepared in safety operation, meet the dual demand for development of environmental economy.
Technical scheme of the present invention is: a kind of preparation method of Ortho Nitro Benzaldehyde, comprises the steps:
(1) bromination reaction
In reactor, add Ortho Nitro Toluene, solvent halogenated aryl hydrocarbon, the two alkyl nitrile of catalyzer azo, constantly stir lower control temperature 40-50 DEG C of dropping bromine, the using dosage of bromine is 0.5-0.6 times of theoretical amount, drip off post-heating back flow reaction to bromine color fade, then add hydrogen peroxide back flow reaction and be no less than 2h, generate o-nitrobenzyl bromide reaction solution;
(2) hydrolysis reaction
In the reaction solution of the first step, add aqueous sodium carbonate, reflux hydrolysis reaction, generate nitro alcohol target product and Sodium Bromide by product.Liquid liquid Separation organic phase and aqueous phase, organic phase primary product is nitro alcohol, and aqueous phase is aqueous sodium bromide.
(3) oxidizing reaction
In nitro alcohol organic phase, add sodium hydroxide, drip hydrogen peroxide in temperature 25-35 DEG C under constantly stirring, heating reflux reaction, generate final product Ortho Nitro Benzaldehyde.
The two alkyl nitrile of azo described in step (1) to be selected from the different caprylic nitrile of Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile) or azo two any one, preferred 2,2'-Azobis(2,4-dimethylvaleronitrile); The consumption of described catalyzer is the 1%-20% of Ortho Nitro Toluene quality; Described halogenated aryl hydrocarbon is selected from chlorobenzene, orthodichlorobenzene or bromobenzene.
Carbonate described in step (2) is salt of wormwood or sodium carbonate, preferred salt of wormwood, and the consumption of carbonate is the 5%-100% of Ortho Nitro Toluene quality; Reflux time is 16-30h.
Hydrogen peroxide mass percent concentration described in step (3) is 10%-50%, preferred 20%-35%; The consumption of sodium hydroxide is the 10%-20% of Ortho Nitro Toluene quality, and reflux time is 20-30h.
Synthetic route of the present invention is as follows:
Take Ortho Nitro Toluene as raw material, adjacent nitro bromobenzyl and hydrogen bromide (hydrogen bromide enters reaction system recycle after being become simple substance bromine by hydrogen peroxide oxidation) is generated with the two alkyl nitrile catalysis bromine bromination Ortho Nitro Toluene of azo, the adjacent nitro bromobenzyl of carbonate aqueous solution catalysis is hydrolyzed to nitro alcohol, and sodium hydroxide catalyzed hydrogen peroxide oxidation nitro alcohol generates target product Ortho Nitro Benzaldehyde.
Present method has significant advantage compared with traditional technology, principal feature has: (1) present method application hydrogen peroxide oxidation method, comparatively other inorganic heavy metal salts and inorganic mineral acid oxidation process, improve the spatter property of industrial preparation feedback, reduce environmental pollution.(2) present method application hydrogen peroxide oxidation method, realizes normal pressure liquid phase preparation feedback, comparatively the compressive reaction of the liquid phase of air (oxygen) method for oxidation, and reaction conditions is gentle, improves industrial preparation manipulation security, energy-conservation.(3) present method improves product yield, and the more current industrial traditional method of productive rate improves about 5%, and present method total recovery reaches 77%, product purity more than 99%.(4) present method application inoganic solids alkaline catalysts catalytic oxidation, does not use a metal-organic complex catalyzer, improves reaction stability, greatly reduces industrial preparation cost.(5) the two alkyl nitrile solid catalyst of present method application azo substitutes peroxycarbonates liquid-phase catalyst, and catalytic bromination reacts, and improves industrial preparation feedback processing safety.(6) present method uses halogenated aryl hydrocarbon solvent medium, instead of halogenated alkane solvents medium, avoids the pollution of lower boiling volatile organic solvent.(7) present method can be reacted at ambient pressure, and reaction conditions is gentle, and industrial preparation manipulation is easy.(8) The method reduces organism by product to generate and inorganic salt (acid) wastewater discharge.(9) present method can according to the market requirement, and preparative separation goes out high purity intermediate compound nitro alcohol.
Accompanying drawing explanation
Fig. 1 is present invention process schema.
Embodiment
Further detailed technology explanation is done below in conjunction with accompanying drawing 1 pair of novel method.
By reference to the accompanying drawings 1, present method comprises three unit process operations, i.e. bromination, hydrolysis, oxidizing reaction.At the first bromination reaction process stages, the two alkyl nitrile catalysis bromine of application azo and Ortho Nitro Toluene react, reaction system recycle is entered after the hydrogen bromide co-product formed is become simple substance bromine by hydrogen peroxide oxidation, so not only reduce the consumption of bromine and decrease waste discharge amount, can production cost be reduced simultaneously.This operation application chlorinated aromatic hydrocarbons substitutes halogenated alkane, avoids the use of volatile organic solvent.At the second hydrolysis reaction process stages, the reaction mixture of the first process stages was directly entered the second reaction process stage, reduce environmental pollution, energy-saving and emission-reduction, the lock out operation in process simplification, is easy to through engineering approaches and implements, except generating nitro alcohol, also have a small amount of Ortho Nitro Benzaldehyde final product, the nitro alcohol in this stage can extract as product separation, and purity is very high.At the 3rd oxidizing reaction process stages, hydrogen peroxide is a kind of cheap environmentally friendly oxygenant, adopt inoganic solids base catalysis hydrogen peroxide oxidation nitro alcohol, highly selective generates Ortho Nitro Benzaldehyde, synthesis under normal pressure, mild condition, simple to operate, do not use a metal-organic complex, greatly reduce material cost.Novel method comparatively conventional industrial process improves about 5% productive rate, decreases organism by product and generates, and avoids the impact on environment such as transition metal salt, has environmental economy dual nature.
Carrying out process in detail with specific embodiment below adopts three unit process operations to prepare Ortho Nitro Benzaldehyde, but does not represent restriction scope of the invention content.
Embodiment 1
In the reactor, add 100g chlorobenzene, 16.4g Ortho Nitro Toluene, 3.3g 2,2'-Azobis(2,4-dimethylvaleronitrile), at 50 DEG C, in 30min, slowly drip 11.5g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 8.5g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the wet chemical of 54.7g30%, stirring and refluxing reaction 16h, after Distillation recovery chlorobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, add 3.2g sodium hydroxide, mixing control temperature 30 DEG C drips the hydrogen peroxide of 58.5g35% in 30min, heating reflux reaction 23h.Be cooled to room temperature after having reacted, standing separation goes out organic phase, and after washing, concentrated organic solvent, refines to obtain 13.6g Ortho Nitro Benzaldehyde through ethanol, GC purity 99.2%, yield 75.1%.
Embodiment 2
In the reactor, add 100g chlorobenzene, 16.4g Ortho Nitro Toluene, 1.5g 2,2'-Azobis(2,4-dimethylvaleronitrile), at 45 DEG C, in 30min, slowly drip 10.8g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 8.5g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the wet chemical of 60.0g30%, stirring and refluxing reaction 16h, after Distillation recovery chlorobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, add 1.5g sodium hydroxide, mixing control temperature 30 DEG C drips the hydrogen peroxide of 75.0g27.5% in 30min, heating reflux reaction 23h.Be cooled to room temperature after having reacted, standing separation goes out organic phase, and after washing, concentrated organic solvent, refines to obtain 14.0g Ortho Nitro Benzaldehyde through ethanol, GC purity 99.1%, yield 77.3%.
Embodiment 3
In the reactor, add 100g orthodichlorobenzene, 16.4g Ortho Nitro Toluene, the different caprylic nitrile of 1.5g azo two, at 45 DEG C, in 30min, slowly drip 10.8g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 8.5g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the wet chemical of 60.0g30%, stirring and refluxing reaction 16h, after Distillation recovery orthodichlorobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, add 1.5g sodium hydroxide, mixing control temperature 30 DEG C drips the hydrogen peroxide of 41.3g50% in 30min, heating reflux reaction 23h.Be cooled to room temperature after having reacted, standing separation goes out organic phase, and after washing, concentrated organic solvent, refines to obtain 13.0g Ortho Nitro Benzaldehyde through ethanol, GC purity 99.0%, yield 71.8%.
Embodiment 4
In the reactor, add 100g chlorobenzene, 16.4g Ortho Nitro Toluene, 1.5g Diisopropyl azodicarboxylate, at 45 DEG C, in 30min, slowly drip 10.8g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 8.5g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the wet chemical of 85.0g22%, after stirring and refluxing reaction 16h, Distillation recovery 85g chlorobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, 2.0g sodium hydroxide, mixing control temperature 30 DEG C drips the hydrogen peroxide of 45.0g27.5% in 30min, heating reflux reaction 26h.Be cooled to room temperature after having reacted, standing separation goes out organic phase, obtains 13.8g Ortho Nitro Benzaldehyde, GC purity 99.3%, yield 76.2% through sodium bisulfite reaction Hydrolysis kinetics.
Embodiment 5
In the reactor, add 100g chlorobenzene, 16.4g Ortho Nitro Toluene, 2.0g Diisopropyl azodicarboxylate, at 45 DEG C, in 30min, slowly drip 10.8g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 8.5g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the wet chemical of 60.0g30%, stirring and refluxing reaction 16h, after Distillation recovery chlorobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, add 2.0g sodium hydroxide, mixing control temperature 30 DEG C drips the hydrogen peroxide of 82.5g20% in 30min, heating reflux reaction 22h.Be cooled to room temperature after having reacted, isolate organic phase, refine to obtain 13.0g Ortho Nitro Benzaldehyde through steam distillation, GC purity 99.7%, yield 71.8%.
Embodiment 6
In the reactor, add 100g chlorobenzene, 16.4g Ortho Nitro Toluene, 1.5g Diisopropyl azodicarboxylate, at 45 DEG C, in 30min, slowly drip 10.8g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 8.5g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the wet chemical of 60.0g25%, stirring and refluxing reaction 30h, after Distillation recovery chlorobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, add 10.0g20% aqueous sodium hydroxide solution, mixing control temperature 30 DEG C drips the hydrogen peroxide of 59.0g35% in 30min, heating reflux reaction 22h.Be cooled to room temperature after having reacted, isolate organic phase, refine to obtain 13.5g Ortho Nitro Benzaldehyde through ethanol, GC purity 99.3%, yield 74.6%.
Embodiment 7
In the reactor, add 100g bromobenzene, 16.4g Ortho Nitro Toluene, 0.1g Diisopropyl azodicarboxylate, at 40 DEG C, in 30min, slowly drip 9.6g bromine, after dropwising, stirring heating back flow reaction is to bromine color fade.The hydrogen peroxide of 7.0g27.5% is slowly dripped, stirring and refluxing reaction 2h in 30min.In this reaction solution, add the aqueous sodium carbonate of 2.7g30%, stirring and refluxing reaction 20h, after Distillation recovery bromobenzene, cool standing separation aqueous phase and contain nitro alcohol organic phase.Organic phase proceeded in reactor, add 1.6g sodium hydroxide, mixing control temperature 35 DEG C drips 204.7g10% hydrogen peroxide in 30min, heating reflux reaction 26h.Be cooled to room temperature after having reacted, standing separation goes out organic phase, and after washing, concentrated organic solvent, refines to obtain 9.3g Ortho Nitro Benzaldehyde through ethanol, GC purity 99.1%, yield 51.3%.
Claims (7)
1. a preparation method for Ortho Nitro Benzaldehyde, is characterized in that, comprises the steps:
(1) bromination reaction
In reactor, add Ortho Nitro Toluene, solvent halogenated aryl hydrocarbon, the two alkyl nitrile of catalyzer azo, constantly stir lower control temperature 40-50 DEG C of dropping bromine, the using dosage of bromine is 0.5-0.6 times of theoretical amount, drip off post-heating back flow reaction to bromine color fade, then add hydrogen peroxide back flow reaction and be no less than 2h, generate o-nitrobenzyl bromide reaction solution;
(2) hydrolysis reaction
In the reaction solution of the first step, add aqueous sodium carbonate, reflux hydrolysis reaction, generate nitro alcohol target product and Sodium Bromide by product.Liquid liquid Separation organic phase and aqueous phase, organic phase primary product is nitro alcohol, and aqueous phase is aqueous sodium bromide.
(3) oxidizing reaction
In nitro alcohol organic phase, add sodium hydroxide, drip hydrogen peroxide in temperature 25-35 DEG C under constantly stirring, heating reflux reaction, generate final product Ortho Nitro Benzaldehyde.
2. the preparation method of Ortho Nitro Benzaldehyde as claimed in claim 1, is characterized in that, the two alkyl nitrile of the azo described in step (1) to be selected from the different caprylic nitrile of Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile) or azo two any one; The consumption of described catalyzer is the 1%-20% of Ortho Nitro Toluene quality; Described halogenated aryl hydrocarbon is selected from chlorobenzene, orthodichlorobenzene or bromobenzene.
3. the preparation method of Ortho Nitro Benzaldehyde as claimed in claim 1 or 2, is characterized in that, the two alkyl nitrile of the azo described in step (1) is selected from 2,2'-Azobis(2,4-dimethylvaleronitrile).
4. the preparation method of Ortho Nitro Benzaldehyde as claimed in claim 1, it is characterized in that, the carbonate described in step (2) is salt of wormwood or sodium carbonate, and the consumption of carbonate is the 5%-100% of Ortho Nitro Toluene quality; Reflux time is 16-30h.
5. the preparation method of the Ortho Nitro Benzaldehyde as described in claim 1 or 4, is characterized in that, the carbonate described in step (2) is salt of wormwood.
6. the preparation method of Ortho Nitro Benzaldehyde as claimed in claim 1, it is characterized in that, the hydrogen peroxide mass percent concentration described in step (3) is 10%-50%; The consumption of sodium hydroxide is the 10%-20% of Ortho Nitro Toluene quality, and reflux time is 20-30h.
7. the preparation method of the Ortho Nitro Benzaldehyde as described in claim 1 or 6, is characterized in that, the hydrogen peroxide mass percent concentration described in step (3) is 20%-35%.
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Cited By (10)
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| CN107032968A (en) * | 2017-05-23 | 2017-08-11 | 连云港市工业投资集团有限公司 | A kind of synthesis technique of 2,3 dichlorobenzaldehyde |
| CN107043321A (en) * | 2017-04-25 | 2017-08-15 | 连云港市工业投资集团有限公司 | A kind of method of the dichlorobenzaldehyde of high selectivity 2,3 |
| CN107778181A (en) * | 2016-08-29 | 2018-03-09 | 浙江中山化工集团股份有限公司 | A kind of new synthesis process of adjacent nitro bromobenzyl |
| CN108707078A (en) * | 2018-06-18 | 2018-10-26 | 东莞市联洲知识产权运营管理有限公司 | A kind of production method of the o-nitrobenzaldehyde based on potassium ethoxide/niobium |
| CN108947848A (en) * | 2018-08-07 | 2018-12-07 | 安庆市长虹化工有限公司 | A kind of nitrification installation and nitration processes method of o-nitrobenzaldehyde preparation |
| CN109810002A (en) * | 2019-02-14 | 2019-05-28 | 安徽泰格生物技术股份有限公司 | A kind of method that useless bromobenzyl prepares benzylamine |
| CN113735712A (en) * | 2021-09-17 | 2021-12-03 | 迈奇化学股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN114195645A (en) * | 2021-11-26 | 2022-03-18 | 金凯(辽宁)生命科技股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN114315588A (en) * | 2021-11-26 | 2022-04-12 | 金凯(辽宁)生命科技股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN115819201A (en) * | 2022-11-22 | 2023-03-21 | 江苏万隆化学有限公司 | Green synthesis process of o-chlorobenzaldehyde catalyzed by titanium silicalite molecular sieve |
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| CN107778181B (en) * | 2016-08-29 | 2020-04-28 | 浙江中山化工集团股份有限公司 | Novel synthesis process of o-nitrobenzyl bromide |
| CN107778181A (en) * | 2016-08-29 | 2018-03-09 | 浙江中山化工集团股份有限公司 | A kind of new synthesis process of adjacent nitro bromobenzyl |
| CN107043321A (en) * | 2017-04-25 | 2017-08-15 | 连云港市工业投资集团有限公司 | A kind of method of the dichlorobenzaldehyde of high selectivity 2,3 |
| CN107043321B (en) * | 2017-04-25 | 2021-01-15 | 连云港市工业投资集团有限公司 | Method for high-selectivity synthesis of 2, 3-dichlorobenzaldehyde |
| CN107032968A (en) * | 2017-05-23 | 2017-08-11 | 连云港市工业投资集团有限公司 | A kind of synthesis technique of 2,3 dichlorobenzaldehyde |
| CN108707078A (en) * | 2018-06-18 | 2018-10-26 | 东莞市联洲知识产权运营管理有限公司 | A kind of production method of the o-nitrobenzaldehyde based on potassium ethoxide/niobium |
| CN108947848A (en) * | 2018-08-07 | 2018-12-07 | 安庆市长虹化工有限公司 | A kind of nitrification installation and nitration processes method of o-nitrobenzaldehyde preparation |
| CN109810002A (en) * | 2019-02-14 | 2019-05-28 | 安徽泰格生物技术股份有限公司 | A kind of method that useless bromobenzyl prepares benzylamine |
| CN113735712A (en) * | 2021-09-17 | 2021-12-03 | 迈奇化学股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN113735712B (en) * | 2021-09-17 | 2024-03-08 | 迈奇化学股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN114195645A (en) * | 2021-11-26 | 2022-03-18 | 金凯(辽宁)生命科技股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN114315588A (en) * | 2021-11-26 | 2022-04-12 | 金凯(辽宁)生命科技股份有限公司 | Preparation method of o-nitrobenzaldehyde |
| CN115819201A (en) * | 2022-11-22 | 2023-03-21 | 江苏万隆化学有限公司 | Green synthesis process of o-chlorobenzaldehyde catalyzed by titanium silicalite molecular sieve |
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Application publication date: 20160330 |