CN112279773B - A kind of synthetic method of high-quality m-phenylenediamine - Google Patents

A kind of synthetic method of high-quality m-phenylenediamine Download PDF

Info

Publication number
CN112279773B
CN112279773B CN202011179650.9A CN202011179650A CN112279773B CN 112279773 B CN112279773 B CN 112279773B CN 202011179650 A CN202011179650 A CN 202011179650A CN 112279773 B CN112279773 B CN 112279773B
Authority
CN
China
Prior art keywords
phenylenediamine
reaction
isophthalonitrile
synthetic method
isophthalimide
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.)
Active
Application number
CN202011179650.9A
Other languages
Chinese (zh)
Other versions
CN112279773A (en
Inventor
王立芹
魏凤
张晓谦
孟宪兴
舒永
陈琦
冯维春
邢文国
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong Xingqiang Chemical Industry Technology Research Institute Co Ltd
Qingdao University of Science and Technology
Original Assignee
Shandong Xingqiang Chemical Industry Technology Research Institute Co Ltd
Qingdao University of Science and Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shandong Xingqiang Chemical Industry Technology Research Institute Co Ltd, Qingdao University of Science and Technology filed Critical Shandong Xingqiang Chemical Industry Technology Research Institute Co Ltd
Priority to CN202011179650.9A priority Critical patent/CN112279773B/en
Priority to PCT/CN2020/129931 priority patent/WO2022088301A1/en
Publication of CN112279773A publication Critical patent/CN112279773A/en
Application granted granted Critical
Publication of CN112279773B publication Critical patent/CN112279773B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
    • C07C209/58—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from or via amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/90—Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C07C231/065—By hydration using metals or metallic ions as catalyst

Landscapes

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

Abstract

本发明属于石油化工有机合成技术领域，具体涉及一种高品质间苯二胺的合成方法。本发明以间苯二腈、无水碳酸钠和双氧水为原料，催化剂作用下合成异邻苯二甲酰亚胺；然后异邻苯二甲酰亚胺与次氯酸钠反应，反应完毕，向其中加入抗氧剂进行后处理，得间苯二胺。本发明合成工艺简单，后处理简单，有效解决了间苯二胺易氧化、品质不高的问题，采用本发明收率达95％以上，纯度达99％以上，大大降低了生产成本，满足市场对于高品质间苯二酚的需求。The invention belongs to the technical field of petrochemical organic synthesis, in particular to a method for synthesizing high-quality m-phenylenediamine. The present invention uses isophthalonitrile, anhydrous sodium carbonate and hydrogen peroxide as raw materials, and synthesizes isophthalimide under the action of a catalyst; then isophthalimide reacts with sodium hypochlorite, and after the reaction is completed, an anti-oxidant is added therein. Oxygen for post-treatment to obtain m-phenylenediamine. The invention has simple synthesis process and simple post-treatment, effectively solves the problems of easy oxidation and low quality of m-phenylenediamine, the yield of the invention is over 95%, the purity is over 99%, the production cost is greatly reduced, and the market is satisfied. Demand for high quality resorcinol.

Description

Synthesis method of high-quality m-phenylenediamine
Technical Field
The invention belongs to the technical field of petrochemical organic synthesis, and particularly relates to a synthesis method of high-quality m-phenylenediamine.
Background
M-phenylenediamine is white needle-like crystal, has a melting point of 62-63 ℃, and is a large amount of known fine chemicals with wide application in related fields such as petroleum, dye, pigment, medicine, pesticide, building auxiliary materials and the like. The traditional process adopts benzene as a starting material, and the process involves double nitration reaction in a nitric acid/sulfuric acid strong corrosive medium and subsequent metal catalysis and/or high-pressure hydrogenation double reduction reaction (iron powder reduction or catalytic hydrogenation, CN108164425, CN 107540554). In the traditional post-treatment process of the m-phenylenediamine, because the reaction solution contains a large amount of iron mud and wastewater which are difficult to treat, the yield is low (about 70 percent), the post-treatment is complex, the m-phenylenediamine product is easy to oxidize in the production process, the product purity is not high, and the high-purity and high-quality m-phenylenediamine is not in demand.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a synthesis method of high-quality m-phenylenediamine, and the product obtained by the method has high purity, high yield, simple post-treatment and low cost.
The invention relates to a synthesis method of high-quality m-phenylenediamine, which comprises the following steps:
(1) dissolving isophthalonitrile in dimethyl sulfoxide, adding anhydrous sodium carbonate and hydrogen peroxide, then adding a catalyst, reacting at 60-80 ℃, and filtering and washing to obtain isophthalimide after the reaction is finished;
(2) under the protection of nitrogen, dissolving sodium hypochlorite in water, controlling the temperature to be-5-20 ℃, adding the isophthalimide under rapid stirring, after the addition, carrying out heat preservation reaction for 2 hours, and then heating to 40-50 ℃ for reaction for 2-3 hours;
(3) and after the reaction is finished, adjusting the pH value of the reaction solution to 7.5-8.5, adding an antioxidant into the reaction solution, distilling under reduced pressure, extracting, and concentrating to obtain the m-phenylenediamine.
In the step (1), the addition amount of dimethyl sulfoxide is 10-15 times of the mass of isophthalonitrile, and the mass of anhydrous sodium carbonate is 5-10% of the mass of isophthalonitrile.
In the step (1), the catalyst is MnO2/SiO2Or Au/TiO2Or Raney-Cu, the adding amount of the catalyst is 0.5 to 2.0 percent of the mol amount of the isophthalonitrile.
In the step (1), the mass fraction of the hydrogen peroxide is 32%, and the molar ratio of the pure substances is as follows: h2O2＝1:1.2～1.3。
In the step (2), the mass of the water is 4.5-8.0 times of that of the sodium hypochlorite.
In step (2), the molar ratio of isophthalimide: sodium hypochlorite 1: 2.2-2.5.
In the step (3), the antioxidant is selected from hindered phenol antioxidants BBMBP or Cyanox2246 or BHT; antioxidant, in terms of mole ratios: isophthalimide is 0.5-1: 1.
In the step (3), after reduced pressure distillation, extracting the kettle substrate by using an organic solvent, wherein the amount of the organic solvent is 3-7 times of the weight of the isophthalimide, and equally dividing into three times of extraction. The organic solvent is selected from ethanol or dimethyl sulfoxide or acetone.
Compared with the prior art, the invention has the beneficial effects that: the synthesis process is simple, the post-treatment is simple, the problems of easy oxidation and low quality of the m-phenylenediamine are effectively solved, the yield reaches more than 95 percent, the purity reaches more than 99 percent, the production cost is greatly reduced, and the market demand on high-quality resorcinol is met.
Detailed Description
In order to better understand the technical scheme of the present invention, the following detailed description of the present invention is provided by way of examples, but the present invention should not be construed as limited to the above description.
The percentages mentioned in the following examples are given by mass.
Example 1
128g of isophthalonitrile is dissolved in 1280g of dimethyl sulfoxide, 12.8g of anhydrous sodium carbonate and 127.2g of 32% hydrogen peroxide are added into the reaction solution at a time, and then Au/TiO is added2，Au/TiO2The addition amount of the isophthalonitrile is 0.5 percent of the molar amount of the isophthalonitrile, the temperature is reduced after the catalytic hydrolysis reaction is carried out for 4 hours at the temperature of 80 ℃, and the reaction solution is filtered and washed to obtain 160.8g of pure product of the isophthalimide.
Under the protection of nitrogen, firstly, 160.4g of sodium hypochlorite is dissolved in 800g of water, 160.8g of isophthalimide is added under the condition of rapid stirring, the feeding temperature is controlled to be-5 ℃, the reaction is carried out for 2 hours under the heat preservation condition after the addition is finished, and then the temperature is raised to 50 ℃ for reaction for 2 hours;
after the reaction is finished, the temperature is reduced to normal temperature, hydrochloric acid is used for adjusting the pH value of reaction liquid to be 7.5, meanwhile, 0.9mol of antioxidant BHT is added, the water is removed by reduced pressure distillation, 500g of ethanol is used for extraction in three batches at the bottom of a kettle, the ethanol extraction liquid is concentrated to obtain 104.8g of offwhite product m-phenylenediamine, the yield is 97.0 percent based on isophthalonitrile, and the purity of the product m-phenylenediamine is 99.8 percent through gas chromatography detection.
Example 2
128g of isophthalonitrile is dissolved in 1280g of dimethyl sulfoxide, 12.8g of anhydrous sodium carbonate and 137.8g of 32% hydrogen peroxide are added to the reaction solution at a time, and MnO is added2/SiO2，MnO2/SiO2The addition amount of the compound is 0.5 percent of the molar amount of the isophthalonitrile, the temperature is reduced after the catalytic hydrolysis reaction is carried out for 5 hours at the temperature of 80 ℃, and the reaction solution is filtered and washed to obtain 158.8g of pure product of the isophthalimide.
Under the protection of nitrogen, firstly, 180g of sodium hypochlorite is dissolved in 1400g of water, 158.8g of isophthalimide is added under the condition of rapid stirring, the feeding temperature is controlled to be 20 ℃, the reaction is carried out for 2 hours after the feeding is finished, and then the temperature is raised to 50 ℃ for reaction for 3 hours;
after the reaction is finished, the temperature is reduced to normal temperature, hydrochloric acid is used for adjusting the pH value of reaction liquid to be 8.5, meanwhile, 0.5mol of antioxidant BHT is added, the water is removed by reduced pressure distillation, 1000g of ethanol is used for extraction in three batches at the bottom of a kettle, ethanol extract is concentrated to obtain 103.1g of off-white product m-phenylenediamine, the yield is 95.5 percent based on isophthalonitrile, and the purity of the product m-phenylenediamine is 99.7 percent detected by gas chromatography.
Example 3
128g of isophthalonitrile was dissolved in 1920g of dimethyl sulfoxide, and 6.4g of anhydrous sodium carbonate and 128.4g of 32% hydrogen peroxide were added to the reaction solution at a time, followed by addition of MnO2/SiO2，MnO2/SiO2The addition amount of the compound is 2.0 percent of the molar amount of the isophthalonitrile, the temperature is reduced after 5 hours of catalytic hydrolysis reaction at 60 ℃, and the reaction solution is filtered and washed to obtain 159.8g of pure product of the isophthalimide.
Under the protection of nitrogen, firstly, 166.7g of sodium hypochlorite is dissolved in 1000g of water, 159.8g of the intermediate isophthalimide is added under the rapid stirring, the feeding temperature is controlled to be minus 5 ℃, the reaction is carried out for 2 hours under the heat preservation after the addition is finished, and then the temperature is raised to 50 ℃ for reaction for 2 hours;
after the reaction is finished, the temperature is reduced to normal temperature, hydrochloric acid is used for regulating the pH value of reaction liquid to be 7.5, cyanox22460.6mol is added at the same time, reduced pressure distillation is carried out to remove water, 800g of ethanol is used for extraction at the bottom of a kettle in three batches, ethanol extract is concentrated to obtain an off-white product, namely m-phenylenediamine 103.8g, the yield is 96.1 percent based on the content of the isophthalonitrile, and the purity of the m-phenylenediamine is 99.5 percent through gas chromatography detection.
Example 4
128g of isophthalonitrile is dissolved in 1520g of dimethyl sulfoxide, 9g of anhydrous sodium carbonate and 130.6g of 32% hydrogen peroxide are added into the reaction solution at one time, then Raney-Cu is added, the addition amount of the Raney-Cu is 2.0% of the molar amount of the isophthalonitrile, the temperature is reduced after the catalytic hydrolysis reaction is carried out for 3h at the temperature of 60 ℃, and 161.8g of pure isophthalimide is obtained after the reaction solution is filtered and washed with water.
Under the protection of nitrogen, firstly, 161.4g of sodium hypochlorite is dissolved in 1130g of water, 161.8g of the intermediate isophthalimide is added under the condition of rapid stirring, the feeding temperature is controlled to be 10 ℃, the reaction is carried out for 2 hours under the heat preservation condition after the addition is finished, and then the temperature is raised to 40 ℃ for reaction for 3 hours;
after the reaction is finished, the temperature is reduced to normal temperature, hydrochloric acid is used for regulating the pH value of reaction liquid to be 8.0, 0.9mol of antioxidant BBMBP is added at the same time, the water is removed by reduced pressure distillation, 900g of ethanol is used for extraction in three batches at the bottom of a kettle, the ethanol extraction liquid is concentrated to obtain an off-white product m-phenylenediamine of 104.4g, the yield is 96.7 percent based on the content of isophthalonitrile, and the purity of the m-phenylenediamine product is 99.3 percent by gas chromatography detection.
Example 5
128g of isophthalonitrile is dissolved in 1660g of dimethyl sulfoxide, 10.2g of anhydrous sodium carbonate and 133.6g of 32% hydrogen peroxide are added to the reaction solution at a time, and then Au/TiO is added2，Au/TiO2The addition amount of the compound is 2.0 percent of the molar amount of the isophthalonitrile, the temperature is reduced after the catalytic hydrolysis reaction is carried out for 3.5h at the temperature of 65 ℃, and the reaction solution is filtered and washed to obtain 161.2g of pure isophthalimide.
Under the protection of nitrogen, firstly 182.7g of sodium hypochlorite is dissolved in 1000g of water, 161.2g of the intermediate isophthalimide is added under the condition of rapid stirring, the feeding temperature is controlled at 10 ℃, the reaction is carried out for 2 hours under the heat preservation condition after the addition is finished, and then the temperature is raised to 40 ℃ for reaction for 2 hours;
after the reaction is finished, the temperature is reduced to normal temperature, hydrochloric acid is used for regulating the pH value of reaction liquid to be 7.5, 0.6mol of antioxidant BBMBP is added at the same time, the water is removed by reduced pressure distillation, 900g of dimethyl sulfoxide is used for extraction in three batches at the bottom of a kettle, the extraction liquid of the dimethyl sulfoxide is concentrated to obtain 103.8g of off-white product m-phenylenediamine, the yield is 96.1 percent based on the isophthalonitrile, and the purity of the product m-phenylenediamine is 99.6 percent detected by gas chromatography.
Example 6
128g of isophthalonitrile is dissolved in 1600g of dimethyl sulfoxide, 9g of anhydrous sodium carbonate and 130.6g of 32% hydrogen peroxide are added into the reaction solution at one time, then Raney-Cu is added, the addition amount of the Raney-Cu is 1.0% of the molar amount of the isophthalonitrile, the temperature is reduced after the catalytic hydrolysis reaction is carried out for 3h at the temperature of 60 ℃, and the reaction solution is filtered and washed by water to obtain 160.0g of pure isophthalimide.
Under the protection of nitrogen, firstly 181.4g of sodium hypochlorite is dissolved in 1000g of water, 160.0g of the intermediate isophthalimide is added under the condition of rapid stirring, the feeding temperature is controlled to be 5 ℃, the reaction is carried out for 2 hours under the heat preservation after the addition is finished, and then the temperature is raised to 40 ℃ for reaction for 3 hours;
after the reaction is finished, the temperature is reduced to normal temperature, hydrochloric acid is used for adjusting the pH value of reaction liquid to be 8.5, antioxidant Cyanox22460.9mol is added at the same time, the reduced pressure distillation is carried out to remove the water, 1000g of acetone is used for extraction in three batches at the bottom of a kettle, the acetone extraction liquid is concentrated to obtain an off-white product, namely m-phenylenediamine 104.2g, the yield is 96.5 percent based on the content of the isophthalonitrile, and the purity of the m-phenylenediamine is 99.4 percent through gas chromatography detection.

Claims (7)

1.一种间苯二胺的合成方法，其特征在于，包括以下步骤：1. a synthetic method of m-phenylenediamine, is characterized in that, comprises the following steps: (1)将间苯二腈溶于二甲基亚砜中，向其中加入无水碳酸钠和双氧水，然后加入催化剂，60～65℃反应，反应完毕，经过滤、水洗得异邻苯二甲酰亚胺；(1) dissolving isophthalonitrile in dimethyl sulfoxide, adding anhydrous sodium carbonate and hydrogen peroxide to it, then adding a catalyst, reacting at 60～65 ℃, the reaction is completed, and isophthalic acid is obtained by filtration and washing with water imide; (2)氮气保护下，将次氯酸钠溶解于水中，控住温度为-5-20℃，快速搅拌下加入异邻苯二甲酰亚胺，加毕，保温反应2h，然后再升温至40～50℃反应2～3h；(2) Under the protection of nitrogen, dissolve sodium hypochlorite in water, control the temperature to -5-20°C, add isophthalimide under rapid stirring, and keep the reaction for 2h after the addition, and then heat up to 40～50°C ℃ reaction 2～3h; (3)反应完毕，反应液调pH值为7.5～8.5，向其中加入抗氧剂，减压蒸馏，抽提，浓缩得间苯二胺；(3) after the reaction is completed, the pH value of the reaction solution is adjusted to 7.5 to 8.5, an antioxidant is added therein, the vacuum distillation is performed, the extraction is performed, and the m-phenylenediamine is concentrated by concentration; 步骤(1)中，无水碳酸钠为间苯二腈质量的5～10％；所述催化剂为MnO2/SiO2或Au/TiO2或Raney-Cu，催化剂的加入量为间苯二腈摩尔量的0.5％～2.0％；所述双氧水的质量分数为32％，以纯物质的摩尔比计，间苯二腈：H2O2＝1:1.2～1.3。In step (1), the anhydrous sodium carbonate is 5-10% of the mass of isophthalonitrile; the catalyst is MnO 2 /SiO 2 or Au/TiO 2 or Raney-Cu, and the amount of catalyst added is isophthalonitrile 0.5%-2.0% of the molar amount; the mass fraction of the hydrogen peroxide is 32%, and in terms of the molar ratio of pure substances, isophthalonitrile: H 2 O 2 =1:1.2-1.3. 2.根据权利要求1所述的一种间苯二胺的合成方法，其特征在于，步骤(1)中，二甲基亚砜加入量为间苯二腈质量的10～15倍。2. the synthetic method of a kind of m-phenylenediamine according to claim 1, is characterized in that, in step (1), dimethyl sulfoxide addition is 10～15 times of isophthalonitrile quality. 3.根据权利要求1所述的一种间苯二胺的合成方法，其特征在于，步骤(2)中，水的质量为次氯酸钠质量的4.5～8.0倍。3. the synthetic method of a kind of m-phenylenediamine according to claim 1, is characterized in that, in step (2), the quality of water is 4.5～8.0 times of sodium hypochlorite quality. 4.根据权利要求1所述的一种间苯二胺的合成方法，其特征在于，步骤(2)中，以摩尔比计，异邻苯二甲酰亚胺：次氯酸钠＝1:2.2-2.5。4. the synthetic method of a kind of m-phenylenediamine according to claim 1, is characterized in that, in step (2), in mol ratio, isophthalimide: sodium hypochlorite=1:2.2-2.5 . 5.根据权利要求1所述的一种间苯二胺的合成方法，其特征在于，步骤(3)中，所述抗氧剂选自受阻酚类抗氧剂BBMBP或Cyanox2246或BHT；以摩尔比计，抗氧剂：异邻苯二甲酰亚胺＝0.5-1:1。5. the synthetic method of a kind of m-phenylenediamine according to claim 1, is characterized in that, in step (3), described antioxidant is selected from hindered phenolic antioxidant BBMBP or Cyanox2246 or BHT; Ratio meter, antioxidant: isophthalimide=0.5-1:1. 6.根据权利要求1所述的一种间苯二胺的合成方法，其特征在于，步骤(3)中，减压蒸馏后，釜底物采用有机溶剂抽提，有机溶剂用量为异邻苯二甲酰亚胺重量的3～7倍，均分成三次抽提。6. the synthetic method of a kind of m-phenylenediamine according to claim 1, is characterized in that, in step (3), after underpressure distillation, still bottom adopts organic solvent extraction, and organic solvent consumption is iso-o-phenylene 3 to 7 times the weight of the dicarboximide is divided into three extractions. 7.根据权利要求6所述的一种间苯二胺的合成方法，其特征在于，所述有机溶剂选自乙醇或二甲基亚砜或丙酮。7. the synthetic method of a kind of m-phenylenediamine according to claim 6, is characterized in that, described organic solvent is selected from ethanol or dimethyl sulfoxide or acetone.
CN202011179650.9A 2020-10-29 2020-10-29 A kind of synthetic method of high-quality m-phenylenediamine Active CN112279773B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202011179650.9A CN112279773B (en) 2020-10-29 2020-10-29 A kind of synthetic method of high-quality m-phenylenediamine
PCT/CN2020/129931 WO2022088301A1 (en) 2020-10-29 2020-11-19 Method for synthesizing m-phenylenediamine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202011179650.9A CN112279773B (en) 2020-10-29 2020-10-29 A kind of synthetic method of high-quality m-phenylenediamine

Publications (2)

Publication Number Publication Date
CN112279773A CN112279773A (en) 2021-01-29
CN112279773B true CN112279773B (en) 2022-01-07

Family

ID=74373344

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202011179650.9A Active CN112279773B (en) 2020-10-29 2020-10-29 A kind of synthetic method of high-quality m-phenylenediamine

Country Status (2)

Country Link
CN (1) CN112279773B (en)
WO (1) WO2022088301A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112142615B (en) * 2020-10-29 2021-11-23 山东兴强化工产业技术研究院有限公司 Preparation method of isophthalimide
CN112174828B (en) * 2020-10-29 2022-01-07 山东兴强化工产业技术研究院有限公司 A kind of method for preparing m-phenylenediamine

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05255214A (en) * 1992-03-11 1993-10-05 Showa Denko Kk Hydration of nitrile compound
CN102285850B (en) * 2011-08-30 2014-01-22 复旦大学 Method for preparing amide from nitrile by hydration in presence of supported gold as catalyst
CN108430994B (en) * 2015-10-06 2022-04-12 蛋白质平衡治疗股份有限公司 Compounds, compositions and methods for modulating CFTR
CN110437080A (en) * 2019-08-13 2019-11-12 上海哈峰新材料科技有限公司 The preparation method of m-phenylene diamine (MPD)
CN111100012B (en) * 2019-12-16 2021-01-22 上海交通大学 Method for preparing m-phenylenediamine
CN111440074A (en) * 2020-03-24 2020-07-24 深圳有为技术控股集团有限公司 Hofmann rearrangement method for preparing m-phenylenediamine

Also Published As

Publication number Publication date
WO2022088301A1 (en) 2022-05-05
CN112279773A (en) 2021-01-29

Similar Documents

Publication Publication Date Title
CN112279773B (en) A kind of synthetic method of high-quality m-phenylenediamine
CN107216289A (en) A kind of preparation method of Edaravone
US9707547B2 (en) Oxidation catalyst for furfural compounds and applying method thereof
CN112300009A (en) Preparation method of m-phenylenediamine
CN109574814B (en) Method for preparing benzaldehyde and benzyl alcohol by liquid-phase catalytic oxidation of toluene
CN113480433A (en) Preparation method of 3-methyl-4-nitrobenzoic acid
CN112645799A (en) Resorcinol post-treatment process
CN117720490A (en) 2, 5-furandicarboxylic acid and purification method thereof
CN112174828B (en) A kind of method for preparing m-phenylenediamine
CN102936213B (en) Clean preparation method of 1, 8-dinitro-3, 6-naphthalenedisulfonic acid
RU2333195C1 (en) Method for obtaining palladium acetate
KR102604509B1 (en) Method for preparing 2,5-diaminotoluene sulfate
CN112142615B (en) Preparation method of isophthalimide
CN111116430B (en) Preparation method of sodium taurate
CN113354623B (en) Preparation method of ilaprazole key intermediate 5- (1H-pyrrole-1-yl) -2-mercaptobenzimidazole
CN116589379B (en) A post-treatment process for m-trifluoromethylacetophenone oxime
CN115286593B (en) Preparation method of dibenzothiazyl disulfide serving as rubber vulcanization accelerator
CN115650860B (en) Synthesis method of 2,2 ', 5' -tetrachlorobenzidine
CN114249352B (en) Method for treating wastewater generated in production of 6-methoxy tetralone
CN118771968B (en) A method for separating and utilizing 2,4-dichloro-5-fluoroacetophenone mother liquor
CN112142587B (en) Acetophenone acid and preparation method and application thereof
CN116102531B (en) Preparation method of salicyl fluorone
WO2024087156A1 (en) Scalable production method for 4-hydroxy-n,n,2-trimethylbenzimidazole-6-carboxamide
CN119552075A (en) A method for preparing 1,1-ethylene glycol diacetate
CN119751280A (en) Preparation method of 2-methyl-4-methoxy diphenylamine

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant