CN103396318B - Synthetic process for 2,4-dinitroanisole - Google Patents
Synthetic process for 2,4-dinitroanisole Download PDFInfo
- Publication number
- CN103396318B CN103396318B CN201310325839.8A CN201310325839A CN103396318B CN 103396318 B CN103396318 B CN 103396318B CN 201310325839 A CN201310325839 A CN 201310325839A CN 103396318 B CN103396318 B CN 103396318B
- Authority
- CN
- China
- Prior art keywords
- methyl alcohol
- alkali
- reaction
- synthesis technique
- dinitroanisols
- 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
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthetic process for 2,4-dinitroanisole. The synthetic process comprises the following steps of: heating and dissolving composite inorganic base into methanol to obtain a methanol alkali solution, then dropwise adding the methanol alkali solution into a methanol solution containing the 2,4-dinitroanisole to react, after finishing the reaction, carrying out cooling crystallization on the obtained reaction liquid, filtering to obtain a filter cake and filter liquid, washing the filter cake by utilizing water of 30-35 DEG C to obtain solids and washing liquid, and drying the obtained solids to obtain 2,4-dinitroanisole; and regulating the pH of the obtained washing liquid to be 2-4, and carrying out the cooling crystallization, filtering, water washing and drying to obtain 2,4-dinitrophenol. The synthetic process has the advantages that the purity and yield of the 2,4-dinitroanisole are improved, the water volume of mother liquid is effectively reduced, and the mother liquid can be continuously and mechanically applied after being processed, is accordant with industrial production requirements and can be used for industrial production.
Description
Technical field
The invention belongs to catalyst preparation technical field, be specifically related to a kind of synthesis technique of 2,4-dinitroanisol.
Background technology
2,4-dinitroanisol (CAS:119-27-7) is a kind of important fine-chemical intermediate, can be used for the field of fine chemical such as dyestuff, medicine and agricultural chemicals.Traditional 2,4-dinitroanisol is mainly with methanol as solvent, acid binding agent and 2 are done with mineral alkali, 4-DNCB reaction obtains, wherein, methyl alcohol is raw material, is again reaction solvent, consider from cost, catalytic efficiency and availability, the mineral alkali in reaction is generally the aqueous solution of sodium hydroxide.The a large amount of methanol as solvent of general needs in the technique reported at present, and use the aqueous solution of sodium hydroxide to make to bring large water gaging into, long reaction time in reaction, after reaction, mother liquor can not be applied mechanically by persistent loop, and produce a large amount of waste water, environmental hazard is large; Simultaneously because of the strong basicity of liquid caustic soda, DNFB hydrolysis generation 2, the amount of 2, 4-dinitrophenol increases, general gained 2,4-dinitroanisol and 2,2, 4-dinitrophenol total recovery is no more than 95%, and little for the report of 2,4-dinitroanisol purity of synthesis.
Along with the increasingly stringent administered with Environmental that increasingly sharpens of market competition, recently for producing 2 of a large amount of waste water, 4-dinitroanisol liquid caustic soda method synthesis technique is also being updated, mainly be centered around and how reduce methanol usage, simplification synthesis technique, as CN1146450A, CN102391126A; Also be reported in liquid caustic soda reaction system and add phase-transfer catalyst, can Reaction time shorten, improve the transformation efficiency of DNFB to a certain extent, but all do not relate to the report of mother liquid recycle.
Publication number is that the Chinese patent application of CN1146450A discloses a kind of employing 2,4-dinitrochlorobenzene prepares 2, the method of 4-dinitroanisol, this reaction is reacted as acid binding agent with the aqueous sodium hydroxide solution of 40%, temperature of reaction is 50 ~ 55 DEG C, and the yield of 2, the 4-dinitroanisols be obtained by reacting is 95%, but the content of 2,4-DNP contained in product is not described further.
Publication number is that the Chinese patent application of CN102391126A discloses a kind of employing 2,4-dinitrochlorobenzene prepares 2 as raw material, 4-dinitroanisol and 2, the method of 2, 4-dinitrophenol, the method is reacted using the sodium hydroxide solution of 10% ~ 40% as acid binding agent, and temperature of reaction is 56 ~ 70 DEG C, obtain 2, the mixture of 4-dinitroanisol and 2,4-DNP, then obtains respective product respectively through being separated.
In the processing method reported, constantly drip liquid caustic soda in the reaction, due to the strong basicity of liquid caustic soda, at a certain temperature, accelerate DNFB hydrolysis, the content of byproduct 2,4-DNP increases, make 2,4-dinitroanisol purity drop, yield also reduces; Simultaneously the adding of liquid caustic soda, the reaction water yield increases, and produce a large amount of waste water after reaction, mother liquor can not be applied mechanically by persistent loop, then produces a large amount of waste water, produces larger harm to environment, simultaneously the cost also corresponding increase of aftertreatment technology.
Summary of the invention
The invention provides a kind of synthesis technique of 2,4-dinitroanisol, this synthesis technique can obtain 2,4-dinitroanisol with highly selective and high yield, reduces the generation of 2,4-DNP.
A kind of synthesis technique of 2,4-dinitroanisol, comprises the steps:
The heating of composite inorganic alkali is dissolved in methyl alcohol and obtains methyl alcohol alkali lye, then described methyl alcohol alkali lye is dripped to containing 2, react in the methanol solution of 4-dinitrochlorobenzene, after having reacted, by the reaction solution decrease temperature crystalline obtained, then filter and obtain filter cake and filtrate, 30 ~ 35 DEG C of water washings of gained filter cake obtain solid and washing lotion, the solid obtained obtains 2,4-described dinitroanisols through super-dry;
The washing lotion obtained adjusts pH to 2 ~ 4, obtains 2,4-DNP through crystallisation by cooling, filtration, washing and drying;
Described composite inorganic alkali is made up of the alkali of sodium hydroxide and calcic or magnesium.
In the present invention, described calcic or the alkali of magnesium are pH value regulator, by with sodium hydroxide compound after, effectively can suppress the hydrolysis of DNFB, reduce the generation of 2,4-DNP, improve yield and the purity of 2,4-dinitroanisol.Meanwhile, the alkali of sodium hydroxide and calcic or magnesium carries out compound in methanol solvate, decreases the use of a large amount of aqueous solution, reduces the discharge of waste water.
As preferably, described calcic or the alkali of magnesium are at least one in magnesium oxide, calcium oxide, magnesiumcarbonate, calcium carbonate, after these four kinds of alkali and sodium hydroxide compound, can suppress the hydrolysis of DNFB better.
As further preferred, the mol ratio of the alkali of described sodium hydroxide and described calcic or magnesium is 15 ~ 25:1.The consumption of sodium hydroxide is too high, and what can make the byproduct 2,4-DNP in product must measure increase; The consumption of sodium hydroxide is too low, the transformation efficiency of DNFB can be made to reduce, can affect yield and the purity of 2,4-dinitroanisol equally.
As preferably, 2, the mol ratio of the methyl alcohol in the methyl alcohol in 4-dinitrochlorobenzene, described methanol solution, composite inorganic alkali and described methyl alcohol alkali lye is 1:2 ~ 4:1.02 ~ 1.08:3 ~ 5, suitably can be improved the purity of described 2,4-dinitroanisols by the consumption increasing methyl alcohol, but the consumption of methyl alcohol is not easily too much, otherwise product 2 can be made, 4-dinitroanisol is dissolved in methyl alcohol, reduces the yield of product 2,4-dinitroanisol.
The raising of temperature of reaction can increase the transformation efficiency of reaction, but temperature is too high, can accelerate the hydrolysis of described DNFB, can make yield and the purity drop of 2,4-described dinitroanisols on the contrary, and as preferably, the temperature of reaction is 70 ~ 75 DEG C.
Described methyl alcohol alkali lye adds in reaction solution by the mode dripped, and rate of addition is unsuitable too fast, otherwise local concentration of lye can be caused too high, and temperature rises too fast, and side reaction increases, and as preferably, the time for adding of described methyl alcohol alkali lye is 30 ~ 45 minutes.
React the degree of carrying out to be monitored by HPLC or TLC, as preferably, the reaction times is 3 ~ 6 hours.
Last handling process after reaction terminates is as follows: directly lowered the temperature by reaction solution, room temperature is cooled under stirring, suction filtration after crystallization, obtain filter cake and filtrate, the filter cake neutrality that is washed to of 30 ~ 35 DEG C obtains solid and washing lotion, 2, the 4-dinitroanisols obtained, purity (HPLC) is more than 99%, and yield is more than 95%.The gained washing lotion technical hydrochloric acid of 31% regulates pH=2 ~ 4, and 5 ~ 15 DEG C are stirred lower crystallisation by cooling, and filter, be washed to neutrality, obtain byproduct 2,4-DNP, purity (HPLC) is more than 98%, and yield is no more than 3%.
As preferably, described filtrate obtains mother liquor and distillate after underpressure distillation;
Mother liquid obtainedly carry out recycled;
Gained distillate reclaims methyl alcohol through rectifying, and this methyl alcohol can participate in reaction again as solvent, and the object of rectifying is in order to methyl alcohol of purifying further, the water produced in removal reaction, ensures to recycle rear reaction system anhydrous.
Compared with the existing technology, beneficial effect of the present invention is embodied in: the aqueous solution replacing sodium hydroxide in the reaction with the methyl alcohol alkali lye of inorganic compounding alkali, not only increase reaction preference, decrease the generation of by product 2,4-DNP, and effectively reduce methanol usage, mother liquor is sustainable after treatment to be applied mechanically, and wastewater flow rate reduces, and reduces environmental pollution, greatly reduce waste water aftertreatment cost simultaneously, can suitability for industrialized production be carried out.
Accompanying drawing explanation
Fig. 1 is the schema of the synthesis technique of 2,4-dinitroanisols of the present invention.
Embodiment
Flow process below in conjunction with specific embodiment and Fig. 1 is described in further detail the present invention.
Embodiment 1
(1) in the four-hole boiling flask of 150mL, methyl alcohol 32g(1mol is added), slowly add solid sodium hydroxide 16g(0.4mol under stirring) and magnesium oxide 0.8g(0.02mol), control temperature is no more than 65 DEG C and obtains methyl alcohol alkali lye to solid is entirely molten, stand-by.
(2) in the four-hole boiling flask of 500mL, methyl alcohol 45g(1.41mol is added), add DNFB 81g(0.4mol under stirring), be heated to DNFB entirely molten.Drip the methyl alcohol alkali lye that complete step (1) obtains in 30min, 70 DEG C of insulation reaction 3 hours.After be cooled to room temperature, suction filtration after crystal is separated out, collect filtrate 83g, filtrate after underpressure distillation mother liquor 45g.Filter cake with 30 DEG C be washed to neutrality, collect washing lotion, dry cake obtains 2,4-dinitroanisol 76.4g, and in DNFB, yield is 96.3%, liquid chromatographic detection purity 99.3%.The gained washing lotion hydrochloric acid of 31% regulates pH=2 ~ 4, stirs lower 5 ~ 15 DEG C of crystallisation by cooling, filters, be washed to neutrality, obtain 2,4-DNP 1.66g, in DNFB, and yield 2.25%, liquid chromatographic detection purity 98.5%.
Mother liquid recycle: (3) add methyl alcohol 32g(1mol in the four-hole boiling flask of 150mL), slowly add solid sodium hydroxide 16g(0.4mol under stirring) and magnesium oxide 0.8g(0.02mol), control temperature be no more than 65 DEG C entirely molten to solid, stand-by.
(4) add in the four-hole boiling flask of 500mL, mother liquor 45g, methyl alcohol 27g(0.85mol) stir under add DNFB 81g(0.4mol), be heated to DNFB entirely molten.Drip the methyl alcohol alkali lye that complete step (3) obtains in 30min, 70 DEG C of insulation reaction 3 hours.After cool to room temperature, suction filtration after crystal is separated out, collects filtrate 80g, and gained filtrate is obtained mother liquor 45.3g after underpressure distillation, filter cake with 30 DEG C be washed to neutrality, collect washing lotion, dry cake obtains 2,4-dinitroanisol 76.9g, with 2,4-dinitrochlorobenzene meter, yield is 97.0%, liquid chromatographic detection purity 99.0%.The gained washing lotion hydrochloric acid of 31% regulates pH=2 ~ 4, stirs lower 5 ~ 15 DEG C of crystallisation by cooling, filters, be washed to filter cake neutrality, obtain 2,4-DNP 1.67g, in DNFB, and yield 2.27%, liquid chromatographic detection purity 98.2%.After mother liquid recycle, the total productive rate of the product obtained slightly rises, and purity does not decline substantially.
Embodiment 2
Methyl alcohol 40g(1.25mol is added in step (1)) by the method described in embodiment 1.
Methyl alcohol 50g(1.56mol is added in step (2)), 72 DEG C of insulation reaction 5 hours.Obtain filtrate 96g, the mother liquor 58g of filtrate after underpressure distillation, 2,4-dinitroanisol 76.0g, in DNFB, yield is 95.8%, liquid chromatographic detection purity 99.8%.Obtain 2,4-DNP 1.77g, in DNFB, yield 2.4%, liquid chromatographic detection purity 99.0%.
Mother liquid recycle: add methyl alcohol 40g(1.25mol in step (3) by the method described in embodiment 1).
Mother liquor 58g is added, methyl alcohol 25.6g(0.8mol in step (4)), 72 DEG C of insulation reaction 5 hours.Obtain filtrate 108g, 2,4-dinitroanisol 76.5g, in DNFB, yield is 96.5%, liquid chromatographic detection purity 99.5%.Obtain mother liquor 58g after 108g filtrate decompression being distilled, obtain 2,4-DNP 1.80g, in DNFB, yield 2.44%, liquid chromatographic detection purity 98.7%.
Embodiment 3
Methyl alcohol 44.8g(1.4mol is added in step (1)) by the method described in embodiment 1.
Methyl alcohol 57.6g(1.8mol is added in step (2)), 75 DEG C of insulation reaction 6 hours.Obtain filtrate 110g, the mother liquor 70g of filtrate after underpressure distillation, obtains 2,4-dinitroanisol 75.3g, and in DNFB, yield is 95%, liquid chromatographic detection purity 99.5%.Obtain 2,4-DNP 2.12g, in DNFB, yield 2.88%, liquid chromatographic detection purity 98.3%.
Mother liquid recycle: add methyl alcohol 44.8g(1.4mol in step (3) by the method described in embodiment 1).
Mother liquor 70g is added, methyl alcohol 28.8g(1.8mol in step (4)), 75 DEG C of insulation reaction 6 hours.Obtain filtrate 105g, the mother liquor 70g of filtrate after underpressure distillation, obtains 2,4-dinitroanisol 75.5g, and in DNFB, yield is 95.2%, liquid chromatographic detection purity 99.3%.Obtain 2,4-DNP 2.15g, in DNFB, yield 2.92%, liquid chromatographic detection purity 98.2%.
Embodiment 4
Methyl alcohol 40g(1.25mol is added in step (1) by the method described in embodiment 1), solid sodium hydroxide 16.6g(0.415mol) and magnesium oxide 0.72g(0.018mol).
Methyl alcohol 51.2g(1.6mol is added in step (2)), 72 DEG C of insulation reaction 5 hours.Obtain filtrate 98g, the mother liquor 57g of filtrate after underpressure distillation, obtains 2,4-dinitroanisol 75.7g, and in DNFB, yield is 95.5%, liquid chromatographic detection purity 99.6%.Obtain 2,4-DNP 1.78g, in DNFB, yield 2.42%, liquid chromatographic detection purity 98.8%.
Mother liquid recycle: add methyl alcohol 40g(1.25mol in step (3) by the method described in embodiment 1) solid sodium hydroxide 16.6g(0.415mol) and magnesium oxide 0.72g(0.018mol).
Mother liquor 57g is added, methyl alcohol 16g(0.5mol in step (4)), 72 DEG C of insulation reaction 5 hours.Obtain filtrate 88g, filtrate obtains mother liquor 57.2g after underpressure distillation, and 2,4-dinitroanisol 76g, in DNFB, yield is 95.8%, liquid chromatographic detection purity 99.2%, 2,4-DNP 1.84g, with 2,4-dinitrochlorobenzene meter, yield 2.50%, liquid chromatographic detection purity 98.5%.
Embodiment 5
Methyl alcohol 40g(1.25mol is added in step (1) by the method described in embodiment 1), solid sodium hydroxide 15.6g(0.39mol) and magnesium oxide 0.72g(0.018mol).
Methyl alcohol 51.2g(1.6mol is added in step (2)), 72 DEG C of insulation reaction 5 hours.Obtain filtrate 99g, filtrate obtains mother liquor 58.3g, 2,4-dinitroanisol 75.3g after underpressure distillation, and in DNFB, yield is 95.0%, liquid chromatographic detection purity 99.2%.2,4-DNP 1.62g, in DNFB, yield 2.2%, liquid chromatographic detection purity 98.6%.
Mother liquid recycle:
Methyl alcohol 40g(1.25mol is added in step (3) by the method described in embodiment 1) solid sodium hydroxide 15.6g(0.415mol) and magnesium oxide 0.72g(0.018mol).
Mother liquor 58.3g is added, methyl alcohol 12.8g(0.4mol in step (4)), 72 DEG C of insulation reaction 5 hours.Obtain filtrate 104g, the mother liquor 58.2g of filtrate after underpressure distillation, obtains 2,4-dinitroanisol 75.4g, and in DNFB, yield is 95.1%, liquid chromatographic detection purity 99%.2,4-DNP 1.64g, in DNFB, yield 2.23%, liquid chromatographic detection purity 98.5%.
Replace magnesium oxide can obtain identical catalytic effect with the calcium oxide of equivalent or calcium carbonate.
Comparative example 1
Methyl alcohol 48g(1.5mol is added in the four-hole boiling flask of 500mL), add DNFB 81g(0.4mol under stirring), be heated to DNFB entirely molten.Drip the aqueous sodium hydroxide solution 168g of 10%, wherein sodium hydrate content is 16.4g(0.41mol), drip in 30min and finish.70 DEG C of insulation reaction 3 hours.After be cooled to room temperature, to adjust behind pH to 8 ~ 10 crystallization under room temperature, suction filtration after crystal is separated out, filter cake with 30 DEG C be washed to neutrality, collect washing lotion, dry cake obtains 2,4-dinitroanisol 39.3g, with 2,4-dinitrochlorobenzene meter, yield is 49.6%, liquid chromatographic detection purity 96.2%.The gained washing lotion hydrochloric acid of 31% regulates pH=2 ~ 4, stirs lower 5 ~ 15 DEG C of crystallisation by cooling, filters, be washed to neutrality, obtain 2,4-DNP 35.5g, in DNFB, and yield 48.2%, liquid chromatographic detection purity 95.6%.
Comparative example 2
(1) in the four-hole boiling flask of 150mL, methyl alcohol 32g(1mol is added), slowly add solid sodium hydroxide 16.8g(0.42mol under stirring), control temperature is no more than 65 DEG C and obtains methyl alcohol alkali lye to solid is entirely molten, stand-by.
(2) in the four-hole boiling flask of 500mL, methyl alcohol 45g(1.41mol is added), add DNFB 81g(0.4mol under stirring), be heated to DNFB entirely molten.Drip the methyl alcohol alkali lye that complete step (1) obtains in 30min, 70 DEG C of insulation reaction 3 hours.After be cooled to room temperature, suction filtration after crystal is separated out, collect filtrate 81g, filtrate after underpressure distillation mother liquor 45g.Filter cake with 30 DEG C be washed to neutrality, collect washing lotion, dry cake obtains 2,4-dinitroanisol 75.2g, and in DNFB, yield is 94.8%, liquid chromatographic detection purity 98.5%.The gained washing lotion hydrochloric acid of 31% regulates pH=2 ~ 4, stirs lower 5 ~ 15 DEG C of crystallisation by cooling, filters, be washed to neutrality, obtain 2,4-DNP 2.5g, in DNFB, and yield 3.39%, liquid chromatographic detection purity 97.2%.
Claims (7)
1. one kind 2, the synthesis technique of 4-dinitroanisol, it is characterized in that, comprise the steps: the heating of composite inorganic alkali to be dissolved in methyl alcohol to obtain methyl alcohol alkali lye, then described methyl alcohol alkali lye is dripped to containing 2, react in the methanol solution of 4-dinitrochlorobenzene, after having reacted, by the reaction solution decrease temperature crystalline obtained, then filter and obtain filter cake and filtrate, 30 ~ 35 DEG C of water washings of gained filter cake obtain solid and washing lotion, and the solid drying obtained obtains 2,4-described dinitroanisols;
The washing lotion obtained adjusts pH to 2 ~ 4, obtains 2,4-DNP through crystallisation by cooling, filtration, washing and drying;
Described composite inorganic alkali is made up of the alkali of sodium hydroxide and calcic or magnesium;
Described calcic or the alkali of magnesium are at least one in magnesium oxide, calcium oxide, magnesiumcarbonate, calcium carbonate.
2. the synthesis technique of 2,4-dinitroanisols according to claim 1, is characterized in that, the mol ratio of the alkali of described sodium hydroxide and described calcic or magnesium is 15 ~ 25:1.
3. according to claim 12, the synthesis technique of 4-dinitroanisol, it is characterized in that, the mol ratio of the methyl alcohol in the methyl alcohol in DNFB, described methanol solution, composite inorganic alkali and described methyl alcohol alkali lye is 1:2 ~ 4:1.02 ~ 1.08:3 ~ 5.
4. the synthesis technique of 2,4-dinitroanisols according to claim 1, is characterized in that, the temperature of reaction is 70 ~ 75 DEG C.
5. the synthesis technique of 2,4-dinitroanisols according to claim 1, is characterized in that, the time of reaction is 3 ~ 6 hours.
6. the synthesis technique of 2,4-dinitroanisols according to claim 1, is characterized in that, the time for adding of described methyl alcohol alkali lye is 30 ~ 45 minutes.
7. the synthesis technique of 2,4-dinitroanisols according to claim 1, is characterized in that, described filtrate obtains mother liquor and distillate after underpressure distillation;
The mother liquor obtained carries out recycled;
The distillate obtained reclaims methyl alcohol through rectifying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310325839.8A CN103396318B (en) | 2013-07-30 | 2013-07-30 | Synthetic process for 2,4-dinitroanisole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310325839.8A CN103396318B (en) | 2013-07-30 | 2013-07-30 | Synthetic process for 2,4-dinitroanisole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103396318A CN103396318A (en) | 2013-11-20 |
| CN103396318B true CN103396318B (en) | 2015-03-25 |
Family
ID=49560101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310325839.8A Active CN103396318B (en) | 2013-07-30 | 2013-07-30 | Synthetic process for 2,4-dinitroanisole |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103396318B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566121A (en) * | 2014-10-11 | 2016-05-11 | 中国石油化工股份有限公司 | Method for reducing generation of nitrophenol in preparation process of nitroanisole |
| CN105777550B (en) * | 2016-05-13 | 2019-01-15 | 湖北东方化工有限公司 | The method that one kind being continuously synthesizing to 2,4- dinitroanisol |
| CN111187168A (en) * | 2019-12-12 | 2020-05-22 | 中卫市鑫三元化工有限公司 | Clean production process for producing nitrobenzene alkoxy ether by using nitrohalogenated benzene |
| CN114163353B (en) * | 2021-12-14 | 2024-05-28 | 郑州大学 | Preparation method of anisic nitrile |
| CN114507141B (en) * | 2021-12-23 | 2024-01-23 | 中北大学 | Method for controlling 2,4-dinitroanisole crystal form |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1146450A (en) * | 1995-09-29 | 1997-04-02 | 陈陆武 | Technological process for preparation of 2-amino-4- acetaminoanisole by 2,4-dinitro chlorobenzene |
| CN102391126A (en) * | 2011-10-17 | 2012-03-28 | 山东昌邑灶户盐化有限公司 | Method for producing 2, 4-dinitrobenzene methyl ether and 2, 4- dinitrophenol simultaneously |
-
2013
- 2013-07-30 CN CN201310325839.8A patent/CN103396318B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN103396318A (en) | 2013-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103396318B (en) | Synthetic process for 2,4-dinitroanisole | |
| CN103539700B (en) | Preparation method of N-cyanoethylaniline | |
| CN104177250A (en) | Process for producing glycollic acid from methyl glycolate | |
| CN101891649A (en) | Novel 3-cyano methyl benzoate preparing method | |
| CN103724279B (en) | One step to form the loop prepares the convenient synthetic method of 2-methyl-4-amino-5-amino methylpyrimidine | |
| CN106631776A (en) | Green preparation process for synthesizing 12-carbon alcohol ester by double catalytic system | |
| CN101560183A (en) | Method for preparing 5-bromo-2-methylpyridine | |
| CN103951561B (en) | A kind of heteropoly acid catalysis prepares the method for MENTHOL glyoxylic ester monohydrate | |
| CN106187787A (en) | A kind of preparation method of 2 amino 4 chlorodiphenyl ethers | |
| CN103508974A (en) | Method for treating methyl 2-(aminosulfonyl)benzoate crystallization mother solution | |
| CN102786403A (en) | Preparation method for 4-tertiary butyl-4'-methoxy dibenzoyl methane | |
| CN104447509B (en) | A kind of preparation technology of tirofiban hydrochloride | |
| CN102408329B (en) | Preparation method of 2,4-dihydroxy benzoic acid | |
| CN104892371A (en) | Method for producing glycol dimethyl ether | |
| CN108530301A (en) | A kind of synthetic method of tri- fluorin benzyl amines of 2,4,6- | |
| CN103288650A (en) | Hydrochloric acid 1-amino-3, 5-dimethyl adamantane preparation method | |
| CN106957235B (en) | A kind of preparation method of tamoxifen | |
| CN102010325A (en) | Method for synthesizing p-hydroxyphenylacetic acid | |
| CN103755706B (en) | A kind of environment-friendly preparation method synthesizing folic acid | |
| CN106278914A (en) | A kind of synthesis technique of DCPTA | |
| CN102363598B (en) | Method for preparing high-purity gabapentin | |
| CN102633625B (en) | Preparation method of fluorocinnamic acid | |
| CN101607871B (en) | Method for preparing 4,4' -dimethylolbiphenyl | |
| CN103304405B (en) | A kind of method of selective chlorination | |
| CN112142579A (en) | Preparation process of 2-hydroxy-4-methoxybenzophenone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |