CN105218375A - A kind of synthetic method of 2-methyl-4-nitrobenzoic acid - Google Patents
A kind of synthetic method of 2-methyl-4-nitrobenzoic acid Download PDFInfo
- Publication number
- CN105218375A CN105218375A CN201510722071.7A CN201510722071A CN105218375A CN 105218375 A CN105218375 A CN 105218375A CN 201510722071 A CN201510722071 A CN 201510722071A CN 105218375 A CN105218375 A CN 105218375A
- Authority
- CN
- China
- Prior art keywords
- methyl
- acid
- massfraction
- temperature
- acetic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of synthetic method of 2-methyl-4-nitrobenzoic acid, belong to chemosynthesis technical field.The present invention take toluene as raw material, add the reaction solution mixing that concentrated nitric acid and the vitriol oil mix, after sodium hydroxide solution washing, react with tindichloride, iron powder, Glacial acetic acid, drip mixed in hydrochloric acid again and obtain 2-amino-5-nitrotoluene, again with acetic acid and vitriol oil hybrid reaction, after the oxidation of oxygenant Sodium peroxoborate, frozen water is lowered the temperature, deionized water wash, again at oxidant potassium permanganate under this oxygenizement, react with mixed in hydrochloric acid, then leave standstill, suction filtration, dry obtained.The invention has the beneficial effects as follows: the method building-up process is simple, and cost is low, and by product is few; Products obtained therefrom productive rate up to more than 95%, high purity more than 99%.
Description
Technical field
The present invention relates to a kind of synthetic method of 2-methyl-4-nitrobenzoic acid, belong to chemosynthesis technical field.
Background technology
Phenylformic acid is also known as M-nitro benzoic acid, and the simplest aromatic acid that carboxyl is directly connected with carbon atoms on a benzene ring is that a hydrogen on phenyl ring is replaced the compound formed by carboxyl (-COOH).For colourless, tasteless tabular crystal.Its steam has very strong pungency, easily causes cough after suction.Be slightly soluble in water, be soluble in ethanol, ether, chloroform, benzene, toluene, dithiocarbonic anhydride, tetracol phenixin and turpentine wet goods organic solvent.Extensively be present in occurring in nature with the form of free acid, ester or derivatives thereof, such as, exist with the form of free acid and benzyl ester in loban; Exist in a free form in the leaf and stem skin of some plants; Exist with the form of methyl esters or benzyl ester in volatile oil; Exist with the form of its derivative urobenzoic acid in horse urine.Phenylformic acid is weak acid, stronger than lipid acid.Their chemical property is similar, can form salt, ester, carboxylic acid halides, acid amides, acid anhydrides etc., all not easily oxidized.Benzoic phenyl ring electrophilic substitution reaction can occur, and between mainly obtaining, position replaces product.The general Chang Zuowei medicine of phenylformic acid or sanitas use, and have the effect of Antifungi, bacterium, mould-growth, are usually coated on skin time medicinal, in order to treat the dermatosis of tinea class.For the synthesis of fiber, resin, coating, rubber, tobacco industry.Initial phenylformic acid is hydrolyzed obtained by loban destructive distillation or buck, also can be hydrolyzed obtained by urobenzoic acid.Industrial phenylformic acid obtains with atmospheric oxidation toluene under the catalyzer such as cobalt, manganese exists; Or obtained by Tetra hydro Phthalic anhydride hydrolysis decarboxylation.Benzoic acid and sodium benzoate can be used as the fungistat of latex, toothpaste, jam or other food, also can make the mordant of dyeing and red ink paste used for seals.
Be a kind of important medicine intermediate with the 2-methyl-4-nitrobenzoic acid of phenylformic acid synthesis, can be used for synthesis series of new antitumor drug.At present, the synthetic method of 2-methyl-4-nitrobenzoic acid mainly contains following several, 2-methyl-4-nitrobenzonitrile hydrolysis method, 4-nitro o xylene oxidation method and 2-methyl-PABA oxidation style, 2-methyl-4-nitrobenzonitrile hydrolysis method mainly adopts hydrochloric acid, hydrogen peroxide-sodium hydroxide system, the method hydrolysis 2-methyl-4-nitrobenzonitriles such as sulfuric acid, hydrochloric acid two-step approach, obtain product 2-methyl-4-nitrobenzoic acid.And 2-methyl-4-nitrobenzonitrile needs with 2-methyl-4-nitrophenylamine for raw material, through diazotization and cyanalation obtained, and 2-methyl-4-nitrophenylamine raw material being not easy to obtain.Therefore, adopt the preparation process of raw material 2-methyl-4-nitrobenzonitrile more complicated, cause route longer, process is loaded down with trivial details.4-nitro o xylene oxidation method adopts chlorine bleach liquor to be oxidized 4-nitro o-Xylol, while obtaining 2-methyl-4-nitrobenzoic acid (35.8%), in reaction process, also generate the 2-methyl-5-nitro phenylformic acid of equivalent and a small amount of 4-nitrophthalic acid (9.6%).The method preparation process is complicated, and products therefrom purity is low, productive rate is low, and by product is many.2-methyl-PABA oxidation style is the N-oxygenase obtained from streptomycete, can on selective oxidation phenyl ring acidic-group to bit amino, obtain 2-methyl-4-nitrobenzoic acid with this.But 2-methyl-PABA material price is expensive, is difficult to obtain, greatly limit the method for this kind of method.Therefore, on this basis, work out the synthetic method of the 2-methyl-4-nitrobenzoic acid that a kind of process is simple, by product is few, productive rate is high, there is important economic benefit and social benefit.
Summary of the invention
Technical problem to be solved by this invention: for 2-methyl-4-nitrobenzonitrile hydrolysis method, 4-nitro o xylene oxidation method and 2-methyl-PABA oxidation style synthesis 2-methyl-4-nitrobenzoic acid expensive starting materials are not easy to obtain, preparation process is more complicated, by product is many, cause route longer, process is loaded down with trivial details, production cost is high, the drawback that productive rate is low, provide a kind of synthetic method of 2-methyl-4-nitrobenzoic acid, the present invention take toluene as raw material, after one step is nitrated, with tindichloride, iron powder, hydrochloric acid reaction, again with acetic acid and vitriol oil hybrid reaction, at oxygenant Sodium peroxoborate, potassium permanganate, under the effect of hydrochloric acid two-step oxidation, leave standstill suction filtration drying obtained.The method building-up process is simple, cost is low, and by product is few, and products obtained therefrom purity is high.
For achieving the above object, the synthetic route of 2-methyl-4-nitrobenzoic acid of the present invention is:
the building-up process of the 2-methyl-4-nitrobenzoic acid that the present invention relates to comprises the following steps:
(1) get 5 ~ 10mL massfraction be 69% nitric acid and 3 ~ 5mL massfraction be 98% sulfuric acid, put into reaction vessel, control temperature is 60 ~ 65 DEG C, rotating speed is 100 ~ 200r/min, be uniformly mixed, treat that nitration mixture is cooled to 20 DEG C, by often dripping/speed of 5s slowly drips 30 ~ 40mL toluene, stirs 20 ~ 30min, be placed in hot water bath reaction 40 ~ 45min, then filtered while hot, filtrate is poured in cold water and is cooled to room temperature, with the washing of 20 ~ 40mL sodium hydrogen carbonate solution to alkalescence, then rinse with clear water, obtain 2,5-dinitrotoluene (DNT);
(2) above-mentioned 2,5-dinitrotoluene (DNT) adds 20 ~ 40g tindichloride and 3 ~ 5g iron powder respectively, add 20 ~ 30mL Glacial acetic acid again, speed setting is 500 ~ 700r/min simultaneously, stirs 20 ~ 30min, to be mixed complete after, control temperature is 80 ~ 85 DEG C, drips the hydrochloric acid that 10 ~ 20mL massfraction is 35% wherein, and raising rotating speed is 900 ~ 1200r/min, stir 30 ~ 50min, obtain 2-amino-5-nitrotoluene;
(3) the 2-amino-5-nitrotoluene of the above-mentioned gained of 20 ~ 30mL is got in 70mL there-necked flask, add 15 ~ 20mL acetic acid wherein, control temperature is 50 ~ 60 DEG C, stir 30 ~ 50min, dripping 10 ~ 15mL massfraction while stirring is wherein 98% sulfuric acid, keep temperature-resistant, magnetic agitation 1 ~ 2h, obtain 2-methyl-4-nitracetanilide;
(4) 10 ~ 15mL hydrogen peroxide and 5 ~ 7g Sodium peroxoborate is added respectively at the 2-methyl-4-nitracetanilide of above-mentioned gained, it is 200 ~ 300 DEG C in temperature, pressure is react 1 ~ 2h under 1 ~ 3MPa condition, add 15 ~ 20mL acetic acid wherein again, be cooled to 60 ~ 70 DEG C, stir 30 ~ 50min, to be mixed complete after, be placed in frozen water 3 ~ 5min, after deionized water wash, obtain 2-methyl-4-oil of mirbane ethanamide;
(5) the 2-methyl-4-oil of mirbane ethanamide of above-mentioned gained is put into 80 ~ 100mL reaction flask, respectively to wherein adding 3 ~ 5g potassium permanganate and 15 ~ 20mL clorox, it is 70 ~ 80 DEG C in temperature, rotating speed is under 800 ~ 900r/min, stirs 30 ~ 40min, and in whipping process, slowly drip 10 ~ 20mL massfraction is the hydrochloric acid of 30%, after being added dropwise to complete, reaction 1 ~ 2h, leaves standstill suction filtration, dry 2-methyl-4-nitrobenzoic acid.
The present invention is compared with additive method, and Advantageous Effects is:
(1) products obtained therefrom productive rate of the present invention is up to more than 95%, high purity more than 99%;
(2) the method building-up process is simple, and cost is low, and by product is few.
Embodiment
First get 5 ~ 10mL massfraction be 69% nitric acid and 3 ~ 5mL massfraction be 98% sulfuric acid, put into reaction vessel, control temperature is 60 ~ 65 DEG C, rotating speed is 100 ~ 200r/min, be uniformly mixed, treat that nitration mixture is cooled to 20 DEG C, by often dripping/speed of 5s slowly drips 30 ~ 40mL toluene, stirs 20 ~ 30min, be placed in hot water bath reaction 40 ~ 45min, then filtered while hot, filtrate is poured in cold water and is cooled to room temperature, with the washing of 20 ~ 40mL sodium hydrogen carbonate solution to alkalescence, then rinse with clear water, obtain 2,5-dinitrotoluene (DNT); Then above-mentioned 2,5-dinitrotoluene (DNT) adds 20 ~ 40g tindichloride and 3 ~ 5g iron powder respectively, add 20 ~ 30mL Glacial acetic acid again, speed setting is 500 ~ 700r/min simultaneously, stirs 20 ~ 30min, to be mixed complete after, control temperature is 80 ~ 85 DEG C, drips the hydrochloric acid that 10 ~ 20mL massfraction is 35% wherein, and raising rotating speed is 900 ~ 1200r/min, stir 30 ~ 50min, obtain 2-amino-5-nitrotoluene; Get the 2-amino-5-nitrotoluene of the above-mentioned gained of 20 ~ 30mL again in 70mL there-necked flask, add 15 ~ 20mL acetic acid wherein, control temperature is 50 ~ 60 DEG C, stir 30 ~ 50min, dripping 10 ~ 15mL massfraction while stirring is wherein 98% sulfuric acid, keep temperature-resistant, magnetic agitation 1 ~ 2h, obtain 2-methyl-4-nitracetanilide; 10 ~ 15mL hydrogen peroxide and 5 ~ 7g Sodium peroxoborate is added respectively at the 2-methyl-4-nitracetanilide of above-mentioned gained, it is 200 ~ 300 DEG C in temperature, pressure is react 1 ~ 2h under 1 ~ 3MPa condition, add 15 ~ 20mL acetic acid wherein again, be cooled to 60 ~ 70 DEG C, stir 30 ~ 50min, to be mixed complete after, be placed in frozen water 3 ~ 5min, after deionized water wash, obtain 2-methyl-4-oil of mirbane ethanamide; Finally the 2-methyl-4-oil of mirbane ethanamide of above-mentioned gained is put into 80 ~ 100mL reaction flask, respectively to wherein adding 3 ~ 5g potassium permanganate and 15 ~ 20mL clorox, it is 70 ~ 80 DEG C in temperature, rotating speed is under 800 ~ 900r/min, stirs 30 ~ 40min, and in whipping process, slowly drip 10 ~ 20mL massfraction is the hydrochloric acid of 30%, after being added dropwise to complete, reaction 1 ~ 2h, leaves standstill suction filtration, dry 2-methyl-4-nitrobenzoic acid.
Example 1
First get 5mL massfraction be 69% nitric acid and 3mL massfraction be 98% sulfuric acid, put into reaction vessel, control temperature is 60 DEG C, rotating speed is 100r/min, is uniformly mixed, and treats that nitration mixture is cooled to 20 DEG C, by often dripping/speed of 5s slowly drips 30mL toluene, stirs 20min, be placed in hot water bath and react 40min, then filtered while hot, filtrate is poured in cold water and is cooled to room temperature, with the washing of 20mL sodium hydrogen carbonate solution to alkalescence, then rinse with clear water, obtain 2,5-dinitrotoluene (DNT); Then above-mentioned 2,5-dinitrotoluene (DNT) adds 20g tindichloride and 3g iron powder respectively, add 20mL Glacial acetic acid again, speed setting is 500r/min simultaneously, stirs 20min, to be mixed complete after, control temperature is 80 DEG C, and dripping 10mL massfraction is wherein the hydrochloric acid of 35%, and raising rotating speed is 900r/min, stir 30min, obtain 2-amino-5-nitrotoluene; Get the 2-amino-5-nitrotoluene of the above-mentioned gained of 20mL again in 70mL there-necked flask, add 15mL acetic acid wherein, control temperature is 50 DEG C, stir 30min, dripping 10mL massfraction wherein is while stirring 98% sulfuric acid, keep temperature-resistant, magnetic agitation 1h, obtain 2-methyl-4-nitracetanilide; 10mL hydrogen peroxide and 5g Sodium peroxoborate is added respectively at the 2-methyl-4-nitracetanilide of above-mentioned gained, it is 200 DEG C in temperature, pressure is react 1h under 1MPa condition, add 15mL acetic acid wherein again, be cooled to 60 DEG C, stir 30min, to be mixed complete after, be placed in frozen water 3min, after deionized water wash, obtain 2-methyl-4-oil of mirbane ethanamide; Finally the 2-methyl-4-oil of mirbane ethanamide of above-mentioned gained is put into 80mL reaction flask, respectively to wherein adding 3g potassium permanganate and 15mL clorox, it is 70 DEG C in temperature, rotating speed is under 800r/min, stirs 30min, and in whipping process, slowly drip 10mL massfraction is the hydrochloric acid of 30%, after being added dropwise to complete, reaction 1h, leaves standstill suction filtration, dry 2-methyl-4-nitrobenzoic acid.The method building-up process is simple, and cost is low, and by product is few; Products obtained therefrom productive rate up to 95.8%, high purity 99.15%.
Example 2
First get 8mL massfraction be 69% nitric acid and 4mL massfraction be 98% sulfuric acid, put into reaction vessel, control temperature is 62 DEG C, rotating speed is 150r/min, is uniformly mixed, and treats that nitration mixture is cooled to 20 DEG C, by often dripping/speed of 5s slowly drips 35mL toluene, stirs 25min, be placed in hot water bath and react 42min, then filtered while hot, filtrate is poured in cold water and is cooled to room temperature, with the washing of 30mL sodium hydrogen carbonate solution to alkalescence, then rinse with clear water, obtain 2,5-dinitrotoluene (DNT); Then above-mentioned 2,5-dinitrotoluene (DNT) adds 30g tindichloride and 4g iron powder respectively, add 25mL Glacial acetic acid again, speed setting is 600r/min simultaneously, stirs 25min, to be mixed complete after, control temperature is 83 DEG C, and dripping 15mL massfraction is wherein the hydrochloric acid of 35%, and raising rotating speed is 1100r/min, stir 40min, obtain 2-amino-5-nitrotoluene; Get the 2-amino-5-nitrotoluene of the above-mentioned gained of 25mL again in 70mL there-necked flask, add 18mL acetic acid wherein, control temperature is 55 DEG C, stir 40min, dripping 13mL massfraction wherein is while stirring 98% sulfuric acid, keep temperature-resistant, magnetic agitation 1.5h, obtain 2-methyl-4-nitracetanilide; 12mL hydrogen peroxide and 6g Sodium peroxoborate is added respectively at the 2-methyl-4-nitracetanilide of above-mentioned gained, it is 250 DEG C in temperature, pressure is react 1.5h under 2MPa condition, add 17mL acetic acid wherein again, be cooled to 65 DEG C, stir 40min, to be mixed complete after, be placed in frozen water 4min, after deionized water wash, obtain 2-methyl-4-oil of mirbane ethanamide; Finally the 2-methyl-4-oil of mirbane ethanamide of above-mentioned gained is put into 90mL reaction flask, respectively to wherein adding 4g potassium permanganate and 17mL clorox, it is 75 DEG C in temperature, rotating speed is under 850r/min, stirs 35min, and in whipping process, slowly drip 15mL massfraction is the hydrochloric acid of 30%, after being added dropwise to complete, reaction 1.5h, leaves standstill suction filtration, dry 2-methyl-4-nitrobenzoic acid.The method building-up process is simple, and cost is low, and by product is few; Products obtained therefrom productive rate up to 96.3%, high purity 99.28%.
Example 3
First get 10mL massfraction be 69% nitric acid and 5mL massfraction be 98% sulfuric acid, put into reaction vessel, control temperature is 65 DEG C, rotating speed is 200r/min, is uniformly mixed, and treats that nitration mixture is cooled to 20 DEG C, by often dripping/speed of 5s slowly drips 40mL toluene, stirs 30min, be placed in hot water bath and react 45min, then filtered while hot, filtrate is poured in cold water and is cooled to room temperature, with the washing of 40mL sodium hydrogen carbonate solution to alkalescence, then rinse with clear water, obtain 2,5-dinitrotoluene (DNT); Then above-mentioned 2,5-dinitrotoluene (DNT) adds 40g tindichloride and 5g iron powder respectively, add 30mL Glacial acetic acid again, speed setting is 700r/min simultaneously, stirs 30min, to be mixed complete after, control temperature is 85 DEG C, and dripping 20mL massfraction is wherein the hydrochloric acid of 35%, and raising rotating speed is 1200r/min, stir 50min, obtain 2-amino-5-nitrotoluene; Get the 2-amino-5-nitrotoluene of the above-mentioned gained of 30mL again in 70mL there-necked flask, add 20mL acetic acid wherein, control temperature is 60 DEG C, stir 50min, dripping 15mL massfraction wherein is while stirring 98% sulfuric acid, keep temperature-resistant, magnetic agitation 2h, obtain 2-methyl-4-nitracetanilide; 15mL hydrogen peroxide and 7g Sodium peroxoborate is added respectively at the 2-methyl-4-nitracetanilide of above-mentioned gained, it is 300 DEG C in temperature, pressure is react 2h under 3MPa condition, add 20mL acetic acid wherein again, be cooled to 70 DEG C, stir 50min, to be mixed complete after, be placed in frozen water 5min, after deionized water wash, obtain 2-methyl-4-oil of mirbane ethanamide; Finally the 2-methyl-4-oil of mirbane ethanamide of above-mentioned gained is put into 100mL reaction flask, respectively to wherein adding 5g potassium permanganate and 20mL clorox, it is 80 DEG C in temperature, rotating speed is under 900r/min, stirs 40min, and in whipping process, slowly drip 20mL massfraction is the hydrochloric acid of 30%, after being added dropwise to complete, reaction 2h, leaves standstill suction filtration, dry 2-methyl-4-nitrobenzoic acid.The method building-up process is simple, and cost is low, and by product is few; Products obtained therefrom productive rate up to 97.5%, high purity 99.36%.
Claims (1)
1. a synthetic method for 2-methyl-4-nitrobenzoic acid, is characterized in that concrete synthesis step is:
(1) get 5 ~ 10mL massfraction be 69% nitric acid and 3 ~ 5mL massfraction be 98% sulfuric acid, put into reaction vessel, control temperature is 60 ~ 65 DEG C, rotating speed is 100 ~ 200r/min, be uniformly mixed, treat that nitration mixture is cooled to 20 DEG C, by often dripping/speed of 5s slowly drips 30 ~ 40mL toluene, stirs 20 ~ 30min, be placed in hot water bath reaction 40 ~ 45min, then filtered while hot, filtrate is poured in cold water and is cooled to room temperature, with the washing of 20 ~ 40mL sodium hydrogen carbonate solution to alkalescence, then rinse with clear water, obtain 2,5-dinitrotoluene (DNT);
(2) above-mentioned 2,5-dinitrotoluene (DNT) adds 20 ~ 40g tindichloride and 3 ~ 5g iron powder respectively, add 20 ~ 30mL Glacial acetic acid again, speed setting is 500 ~ 700r/min simultaneously, stirs 20 ~ 30min, to be mixed complete after, control temperature is 80 ~ 85 DEG C, drips the hydrochloric acid that 10 ~ 20mL massfraction is 35% wherein, and raising rotating speed is 900 ~ 1200r/min, stir 30 ~ 50min, obtain 2-amino-5-nitrotoluene;
(3) the 2-amino-5-nitrotoluene of the above-mentioned gained of 20 ~ 30mL is got in 70mL there-necked flask, add 15 ~ 20mL acetic acid wherein, control temperature is 50 ~ 60 DEG C, stir 30 ~ 50min, dripping 10 ~ 15mL massfraction while stirring is wherein 98% sulfuric acid, keep temperature-resistant, magnetic agitation 1 ~ 2h, obtain 2-methyl-4-nitracetanilide;
(4) 10 ~ 15mL hydrogen peroxide and 5 ~ 7g Sodium peroxoborate is added respectively at the 2-methyl-4-nitracetanilide of above-mentioned gained, it is 200 ~ 300 DEG C in temperature, pressure is react 1 ~ 2h under 1 ~ 3MPa condition, add 15 ~ 20mL acetic acid wherein again, be cooled to 60 ~ 70 DEG C, stir 30 ~ 50min, to be mixed complete after, be placed in frozen water 3 ~ 5min, after deionized water wash, obtain 2-methyl-4-oil of mirbane ethanamide;
(5) the 2-methyl-4-oil of mirbane ethanamide of above-mentioned gained is put into 80 ~ 100mL reaction flask, respectively to wherein adding 3 ~ 5g potassium permanganate and 15 ~ 20mL clorox, it is 70 ~ 80 DEG C in temperature, rotating speed is under 800 ~ 900r/min, stirs 30 ~ 40min, and in whipping process, slowly drip 10 ~ 20mL massfraction is the hydrochloric acid of 30%, after being added dropwise to complete, reaction 1 ~ 2h, leaves standstill suction filtration, dry 2-methyl-4-nitrobenzoic acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510722071.7A CN105218375A (en) | 2015-10-31 | 2015-10-31 | A kind of synthetic method of 2-methyl-4-nitrobenzoic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510722071.7A CN105218375A (en) | 2015-10-31 | 2015-10-31 | A kind of synthetic method of 2-methyl-4-nitrobenzoic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
CN105218375A true CN105218375A (en) | 2016-01-06 |
Family
ID=54987720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510722071.7A Pending CN105218375A (en) | 2015-10-31 | 2015-10-31 | A kind of synthetic method of 2-methyl-4-nitrobenzoic acid |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105218375A (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020072626A1 (en) * | 2000-12-13 | 2002-06-13 | James Kantor | Methods for producing 3-cyano- and 4-cyano-benzoic acid derivative compounds |
CN1403437A (en) * | 2002-10-17 | 2003-03-19 | 中国科学院大连化学物理研究所 | Synthesis of nitroarylamine compound |
JP2003335730A (en) * | 2002-05-14 | 2003-11-28 | Asahi Glass Co Ltd | Method for producing 2,4,5-trifluoro-3-methyl-6- nitrobenzoic acid |
CN101774929A (en) * | 2010-01-28 | 2010-07-14 | 浙江大学 | Preparation method of 2-methyl-4-nitrophenylamine |
US20130303781A1 (en) * | 2010-11-24 | 2013-11-14 | Sequent Scientific Limited | Process for preparation of triclabendazole |
CN103408430A (en) * | 2013-08-30 | 2013-11-27 | 南京理工大学 | Synthesis method of 2-methyl-4-nitrobenzoic acid |
-
2015
- 2015-10-31 CN CN201510722071.7A patent/CN105218375A/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020072626A1 (en) * | 2000-12-13 | 2002-06-13 | James Kantor | Methods for producing 3-cyano- and 4-cyano-benzoic acid derivative compounds |
JP2003335730A (en) * | 2002-05-14 | 2003-11-28 | Asahi Glass Co Ltd | Method for producing 2,4,5-trifluoro-3-methyl-6- nitrobenzoic acid |
CN1403437A (en) * | 2002-10-17 | 2003-03-19 | 中国科学院大连化学物理研究所 | Synthesis of nitroarylamine compound |
CN101774929A (en) * | 2010-01-28 | 2010-07-14 | 浙江大学 | Preparation method of 2-methyl-4-nitrophenylamine |
US20130303781A1 (en) * | 2010-11-24 | 2013-11-14 | Sequent Scientific Limited | Process for preparation of triclabendazole |
CN103408430A (en) * | 2013-08-30 | 2013-11-27 | 南京理工大学 | Synthesis method of 2-methyl-4-nitrobenzoic acid |
Non-Patent Citations (1)
Title |
---|
唐波 等: "2-甲基-4-硝基苯甲酸的合成研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104557639A (en) | Method of preparing 2-nitro-4-methylsulfonyl benzoic acid | |
CN115124465B (en) | Preparation method of quinclorac intermediate | |
CN111747840A (en) | Preparation method of 1, 4-naphthalenedicarboxylic acid | |
CN102603536A (en) | Synthetic method of 3-nitrophthalic acid | |
CN106631761A (en) | Method for preparing benzoic acid by oxidizing methylbenzene at atmospheric pressure and low temperature | |
CN105001155A (en) | Oxosynthesis method of methylpyridine-1-oxide | |
CN106117169B (en) | A kind of synthetic method of 2,5- furandicarboxylic acids | |
CN105218375A (en) | A kind of synthetic method of 2-methyl-4-nitrobenzoic acid | |
CN104262109B (en) | A kind of synthetic method of resorcinol | |
CN104211931B (en) | A kind of pure plant oil based polyenoid class UV-curable prepolymer | |
CN104513198A (en) | 2-chloronicotinic acid synthetic method | |
CN102336733A (en) | Method of catalytic oxidation of cyclohexane | |
CN104151236A (en) | Method for efficiently synthesizing quinoline | |
CN105418442A (en) | Synthesis method of 2,4-diaminobenzoic acid | |
CN101759558A (en) | Method for synthesizing trimesic acid | |
CN115368339A (en) | High-yield continuous synthesis method of 2-acetamido-3, 5-dinitrothiophene | |
CN111170908B (en) | Synthesis method of 2, 4-dimethyl-3-methylsulfonyl halogeno-benzene | |
CN113210016A (en) | Composite catalyst and method for preparing trimellitic anhydride | |
CN104230841A (en) | Catalytic synthesis method of 2-acylbenzothiazole or derivatives thereof | |
CN115385855B (en) | Method for preparing quinclorac by two-step oxidation | |
CN115703703B (en) | Method for continuously synthesizing 2-methyl-1, 4-naphthoquinone | |
CN103420785A (en) | Preparation method of 9, 9'-(4-halogen phenyl) fluorene derivative | |
CN103664765A (en) | Preparation method of 2-amino-3-bromopyridine | |
CN108892653B (en) | Method for preparing trimellitic anhydride by oxidizing pseudocumene | |
CN102161607B (en) | Method for preparing fluorine-containing aromatic compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information |
Address after: 213164 Changzhou Province, north of the New District, Jiangsu Biguiyuan, unit B, room 1601, room 32 Applicant after: Ding Yuqin Address before: 213164 Changzhou Province, north of the new North Industrial Park Road, one hundred environmental protection (Fan Qun drying equipment Co., Ltd.) Applicant before: Ding Yuqin |
|
COR | Change of bibliographic data | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160106 |