CN105777547B - A kind of synthetic method of m-nitrobenzaldehyde - Google Patents
A kind of synthetic method of m-nitrobenzaldehyde Download PDFInfo
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Abstract
The present invention provides a kind of synthetic method of m-nitrobenzaldehyde, includes the following steps：Step 1：Reaction, specifically：By copper nitrate, water, silver nitrate and benzaldehyde according to mol ratio be 1.03 1.1：20‑40：0.001‑0.0012：1.0 ratio is reacted, and obtains reaction mixture；Step 2：M-nitrobenzaldehyde crude product processed, specifically：Mother liquor is obtained by filtration in reaction mixture while hot, then solid is filtered to take after mother liquor is cooled down up to m-nitrobenzaldehyde crude product；Step 3：The m-nitrobenzaldehyde of preparing high-purity, specifically：Water-soluble solvent will be added in m-nitrobenzaldehyde crude product, by filtering, drying etc. up to high-purity m-nitrobenzaldehyde.The molar yield of m-nitrobenzaldehyde obtained by the method for the present invention is more than 90%, and chromatographic purity is more than 99.8%, and o-nitrobenzaldehyde is less than 0.1%；The production process three wastes are few, environmentally protective.
Description
Technical field
The present invention relates to organic compound synthesis technical fields, and in particular to a kind of synthetic method of m-nitrobenzaldehyde.
Background technology
M-nitrobenzaldehyde is a kind of very important medicine intermediate, is widely used in the synthesis of a variety of medicine, such as chlorine
Shu Long, Cilnidipine, nitrendipine, Nimodipine etc..At present, domestic production producer is considerably less, and reason is existing production
Complex process, ortho para position poor selectivity need repeated recrystallize just to can obtain qualified products, and high purity product is not high and quantity of three wastes
It is very big, it is very big to environmental disruption.
At present, the method for preparing m-nitrobenzaldehyde is as follows：
Fourth was published in into honor et al. in 2005《Zhejiang Polytechnical University's journal》It is and entitled《M-nitrobenzaldehyde synthesis is new
The research of technique》Article, particular content is：Using benzaldehyde as raw material, the benzaldehyde contracting of generation intermediate is reacted with isopropylamine
Imines, then with mixed acid nitrification, then hydrolyze, obtain target product m-nitrobenzaldehyde.Emphasis to the raw material proportioning of nitration reaction,
Reaction temperature, reaction time and hydrolysis time are investigated, and the raw material proportioning for obtaining nitration reaction is：Benzaldehyde contracting imines：
Sulfuric acid (molar ratio)=1：7, benzaldehyde contracting imines：Nitric acid (molar ratio)=1：1.2, reaction temperature is 10~15 DEG C, during reaction
Between for 2h, hydrolysis time 2.5h, the yield of m-nitrobenzaldehyde is 88.4%, mass fraction 99.1%.
Yellow silver China et al. was published in 2008《Petrochemical industry》It is and entitled《The synthesis technology of m-nitrobenzaldehyde》's
Article, particular content are：Benzaldehyde and ammonium hydroxide condensation three benzaldehyde contracting diamines (TBDA) of generation, through mixed acid nitrification, then hydrolyze conjunction
Into m-nitrobenzaldehyde.Have studied condensation, nitration reaction influence factor, optimize reaction condition, the experimental results showed that：Condensation
Reaction preferable condition be：N (benzaldehyde): n (ammonium hydroxide)=1: 2.4,40 DEG C, reaction time 12h of reaction temperature, on this condition
The yield of TBDA is up to 98.7%；The preferable condition of nitration reaction is：N (TBDA): n (concentrated sulfuric acid)=1: 16, n (TBDA): n is (dense
Nitric acid)=1: 8, nitration reaction temperature is 10~15 DEG C, and the nitration reaction time is 2h, and the yield of m-nitrobenzaldehyde crude product reaches
86.3%；Purity is up to 99.8% after petroleum ether-toluene Mixed Solvent (volume ratio 1.5: 1) recrystallization for crude product, nitro
The total recovery of benzaldehyde is 76.4%.
Institutes Of Technology Of Nanjing's chemical engineering was published in 2007《Fine-chemical intermediate》It is and entitled《M-nitro first
The synthesising process research of aldehyde》Article, specifically：It is catalysis with AIBN (azodiisobutyronitrile) using meta-nitrotoluene as raw material
Agent synthesizes m-nitrobenzaldehyde.At n (meta-nitrotoluene): n (chlorine bromic acid): n (hydrogen peroxide)=1: 3: 3, bromination temperature for 65~
75 DEG C, bromination time is 8~9h, and the oxydrolysis time is 8h, and the yield of m-nitrobenzaldehyde is 30.4%, m-nitrobenzaldehyde
Purity be 99.2%.
The Master's thesis that the Diao Chunli of Institutes Of Technology Of Nanjing was delivered in 2008《The synthesis of m-nitrobenzaldehyde》It discloses
The synthetic method of two kinds of m-nitrobenzaldehydes, Details as Follows：(1) it is made using meta-nitrotoluene as raw material by bromo, hydrolysis, oxidation
Standby m-nitrobenzaldehyde, is specifically optimized three-step reaction condition, specifically：When n (meta-nitrotoluene): n (potassium bromate):
N (niter cake)=1：2.5：2.5, bromination time 4h, bromo temperature are 70 DEG C, n (bromination product)：N (sodium carbonate) is 1：
2, hydrolysis time 7h, hydrolysis temperature are 100 DEG C, and oxidizing temperature is 100 DEG C, and the yield of m-nitrobenzaldehyde is 48.2%；(2)
Using meta-nitrotoluene as raw material, manganese sesquioxide managnic oxide is oxidant, and sulfuric acid is the selective oxidation of the meta-nitrotoluene of reaction medium,
When n (meta-nitrotoluene): n (manganese sesquioxide managnic oxide)=1：1.5, reaction temperature is 90 DEG C, reaction time 7h, m-nitrobenzaldehyde
Yield be 65.6%.
Yield of the more than several method with m-nitrobenzaldehyde is low, production cost is high, the technological process of production is long, pollution is big
The defects of, it is not easy to large-scale industrial production.
With the continuous renewal of technology, the patent of invention application No. is 201110173084.5 discloses a kind of m-nitro
The production technology of formaldehyde, specifically：Using benzaldehyde as raw material, analyse and refined and etc. be made through nitrification, addition, alkali.The present invention
Technique makes ortho isomer control 15% hereinafter, using m-nitrobenzaldehyde and ortho isomer by adjusting nitration condition
The larger difference of addition product solubility under certain condition detached overwhelming majority analysis ortho isomers, the chromatography of crude product
Purity reaches 99.2%, and for chromatographic purity up to more than 99.9%, ortho isomer can be controlled in less than 0.06% after refining.This side
Though method also has the disadvantages that with very high yield：Processing step is long, production cost is very high, and the wastewater flow rate generated
It is very big, and also a large amount of nitrate of content and sulphite, environmental pollution are very big in waste water.
It simplifies in conclusion being badly in need of a kind of production technology in industry, the high income of m-nitrobenzaldehyde, pollute small production
Technique is to solve the deficiencies in the prior art.
Invention content
Present invention aims at provide nitre between a kind of production technology is simplified, the high income of m-nitrobenzaldehyde, pollution are small
The synthetic method of benzaldehyde, specific technical solution are as follows：
A kind of synthetic method of m-nitrobenzaldehyde, includes the following steps：
Step 1：Reaction, specifically：Copper nitrate, water and silver nitrate are added in reaction unit, is warming up to 70 DEG C -80 DEG C；
Benzaldehyde is added dropwise, time for adding is 1.8-2.5 hours；85 DEG C -95 DEG C are warming up to, heat preservation obtains reaction mixture in 2-3 hours；From
Sampling carries out chromatography detection in reaction mixture, and the content of benzaldehyde is less than 0.5%, wherein copper nitrate, water, silver nitrate and benzene
The mol ratio of formaldehyde is 1.03-1.1：20-40：0.001-0.0012：1.0；
Step 2：M-nitrobenzaldehyde crude product processed, specifically：Reaction mixture is filtered to remove hydrogen-oxygen at 85 DEG C -95 DEG C
Change copper to precipitate to obtain mother liquor；Mother liquor is cooled to 10 DEG C -20 DEG C；Solid is filtered to take up to m-nitrobenzaldehyde crude product, between described
The content of o-nitrobenzaldehyde is less than 0.5% in nitrobenzaldehyde crude product；
Step 3：The m-nitrobenzaldehyde of preparing high-purity, specifically：M-nitrobenzaldehyde crude product is packed into reaction unit,
The water-soluble solvent of 3.0-3.5 times of m-nitrobenzaldehyde crude product volume is added in, is warming up to 50 DEG C -55 DEG C；Filtering is removed insoluble miscellaneous
The water of water-soluble solvent same volume is added in after matter；Filtering is dried after taking out the solid being precipitated to get high-purity m-nitro
Formaldehyde.
It is preferred in above technical scheme, copper nitrate in the step 1, silver nitrate, benzaldehyde quality standard be common
Technical grade standard.
It is preferred in above technical scheme, mixing component is equipped in the reaction unit, in the step 1 and step 3
The stir speed (S.S.) of mixing component is 120-160 revs/min.
Preferred in above technical scheme, the temperature dried in the step 3 is 40 DEG C -50 DEG C, and the time is small for 8-12
When.
It is preferred in above technical scheme, the water-soluble solvent is methanol, ethyl alcohol, isopropanol, dimethylformamide with
And any one of tetrahydrofuran.
In order to reach superior technique effect, recycling step is further included, the recycling step includes recycling step A and returns
Receiving step B, the recycling step A is specifically：The Kocide SD precipitation that second step obtains is neutralized with nitric acid, by what is obtained
Copper nitrate solution is used for the reaction in the first step；The recycling step B is specifically：It is filtered during third is walked mother liquid obtained at
Reason is used as water-soluble solvent, wherein, water content is less than 10% in treated mother liquor.
Preferred in above technical scheme, the processing step of mother liquor is specifically in the recycling step B：Mother liquor is pumped into back
Solvent rectifying column is received, control temperature is no more than 60 DEG C, and by adjusting reflux ratio, moisture is controlled 10% among hereinafter, collecting
Fraction.
It applies the technical scheme of the present invention, has the advantages that：Based on benzaldehyde, copper nitrate and silver nitrate
Raw material is wanted, it is easy that raw material obtains, and cost of material is low；It is primary raw material using benzaldehyde and copper nitrate, in the catalysis of copper nitrate
Lower synthesis m-nitrobenzaldehyde crude product, m-nitrobenzaldehyde crude product obtained after simply refined high-purity m-nitrobenzaldehyde into
Product, entire process steps are simplified, with short production cycle, and technological parameter is easy to control, convenient for large-scale production；The present invention uses
Copper nitrate is as nitrating agent, because there is its internal copper ion big steric effect (in order to increase the reactivity of copper nitrate, to add
Silver nitrate is as catalytic reagent), it can utmostly avoid the generation of benzaldehyde ortho-nitration object so that nitre between present invention gained
The molar yield of benzaldehyde is more than 90%, and chromatographic purity is more than 99.8%, and o-nitrobenzaldehyde is less than 0.1%；Hydrogen of the present invention
Copper oxide precipitates and the equal recoverable of mother liquor of subtractive process, substantially reduces the discharge of the three wastes, environmentally protective.
Other than objects, features and advantages described above, the present invention also has other objects, features and advantages.
Below with reference to specific embodiment, the present invention is described in further detail.
Specific embodiment
It is described in detail below in conjunction with the embodiment of the present invention, but the present invention can limit and cover according to claim
The multitude of different ways of lid is implemented.
Embodiment 1：
A kind of synthetic method of m-nitrobenzaldehyde, used raw material and instrument refer to table 1.
1 raw material of table and instrument statistical form
| Raw material parameter | Producer | Specification | Content |
| Copper nitrate | It is unlimited | Seconds | >=99.5% |
| Silver nitrate | It is unlimited | Seconds | >=99.0% |
| Benzaldehyde | It is unlimited | Certified products | >=99.0% |
| Reaction unit | It is unlimited | Three-necked flask | - |
The synthesis of the present embodiment m-nitrobenzaldehyde specifically includes following steps：
Step 1：Reaction, specifically：The copper nitrate of 19.70 grams (0.105mol) is added in reaction unit, at room temperature slowly
The slow water for adding in 50 grams (2.78mol) cause copper nitrate be completely dissolved to obtain copper nitrate solution (rate for herein, adding water is adjustable,
Purpose is to realize that copper nitrate can be completely dissolved)；The silver nitrate of 0.017 gram (0.000101mol) is added in copper nitrate solution
Obtain mixed liquor；Mixed liquor is warming up to the benzaldehyde that 10.60 grams (0.10ml) is slowly added dropwise after 70 DEG C (T1), time for adding is
2.0 hours (t1), reaction solution is obtained after being added dropwise to complete；Reaction solution is warming up to 85 DEG C (T2) and keeps the temperature 2.0 hours (t2) afterwards
Obtain reaction mixture；Sampling carries out chromatography detection from reaction mixture, and the content of benzaldehyde is less than 0.5%；
Step 2：M-nitrobenzaldehyde crude product processed, specifically：Reaction mixture is filtered to remove hydrogen-oxygen when temperature is T2
Change copper to precipitate to obtain mother liquor；Mother liquor is cooled to 10 DEG C (T3)；Solid is filtered to take up to m-nitrobenzaldehyde crude product, m-nitro
The weight of formaldehyde crude product is 20 grams, and the content of o-nitrobenzaldehyde is less than 0.5% in the m-nitrobenzaldehyde crude product；
Step 3：The m-nitrobenzaldehyde of preparing high-purity, specifically：M-nitrobenzaldehyde crude product is packed into reaction unit,
60 milliliters of methanol (water-soluble solvent) is added in, is warming up to 50 DEG C (T4)；The water of 60 milliliters of addition after insoluble impurity is removed in filtering；
Filtering is dried (temperature dried herein is 40 DEG C -50 DEG C, and the time is 8-12 hours) to get height after taking out the solid being precipitated
Purity m-nitrobenzaldehyde, the weight of high-purity m-nitrobenzaldehyde is 14.0 grams at this time.
Further include recycling step in the above process, the recycling step includes recycling step A and recycling step B, described
Recycling step A is specifically：The Kocide SD precipitation that second step obtains with nitric acid is neutralized, obtained copper nitrate solution is used
Reaction process in the first step；The recycling step B is specifically：It is filtered during third is walked mother liquid obtained by handling as water
Soluble solvent, wherein, the processing step of mother liquor is specifically：Mother liquor is pumped into recycling design rectifying column, control temperature is no more than 60
DEG C, by adjusting reflux ratio, (design of reflux ratio specifically can accordingly be adjusted according to the prior art and actual conditions, core
The heart is realized moisture control below 10%), moisture is controlled 10% hereinafter, collecting midbarrel.
Mixing component is equipped in the reaction unit, the stir speed (S.S.) of mixing component is in the step 1 and step 3
120-160 rpms (the stir speed (S.S.) ratio of the two is 11 fast ratios).
In the above process, water bath may be used in the control of temperature, realizes the raising of temperature, reduction and constant；Nitric acid
The molecular weight of copper is 187.56, and the molecular weight of water is 18, and the molecular weight of silver nitrate is 169.8731, and the molecular weight of benzaldehyde is
106.12。
There are two chemical equation involved in the above method is main：
1st, copper nitrate and benzaldehyde synthesizes m-nitrobenzaldehyde under silver nitrate and certain reaction temperature and Kocide SD sinks
It forms sediment.
2nd, Kocide SD neutralizes to obtain copper nitrate and water through pernitric acid.
The high-purity m-nitrobenzaldehyde of the present embodiment is detected using chromatography, the results detailed in Table 4.
Chromatographic test strip part：
Chromatograph：Good fortune founds 9790-II high resolution gas chromatography instrument；
Chromatographic column：The equivalent gas chromatographic columns of HP-50；
Detect temperature：1-5min, 80 DEG C, 6-30min, 5 DEG C/min, 30-40min, 200 DEG C.
Embodiment 2- embodiments 6：
6 difference from Example 1 of embodiment 2- embodiments is table 2.
The parametric statistics table of 2 embodiment 2- embodiments 6 of table
6 gained high-purity m-nitrobenzaldehyde of embodiment 2- embodiments uses chromatographic detection method same as Example 1,
The results detailed in Table 4.
Comparative example 1- comparative examples 4：
4 difference from Example 1 of comparative example 1- comparative examples is table 3：
The parametric statistics table of 3 comparative example 1- comparative examples 4 of table
Comparative example 1- comparative examples 4 use detection method same as Example 1, the results are shown in Table 4.
The chromatography testing result statistical form of 4 comparative example 1- comparative examples 4 of table and embodiment 1- embodiments 6
| Embodiment result | M-nitrobenzaldehyde yield/% | Chromatographic purity/% | O-nitrobenzaldehyde content/% | Three wastes situation |
| Embodiment 1 | 92.71 | 99.9 | ＜ 0.1 | <1.0g |
| Embodiment 2 | 90.73 | 99.8 | ＜ 0.1 | <1.0g |
| Embodiment 3 | 90.73 | 99.9 | ＜ 0.1 | <1.0g |
| Embodiment 4 | 91.39 | 99.9 | ＜ 0.1 | <1.0g |
| Embodiment 5 | 92.05 | 99.8 | ＜ 0.1 | <1.0g |
| Embodiment 6 | 90.73 | 99.8 | ＜ 0.1 | <1.0g |
| Comparative example 1 | 86.66 | 99.2 | ＜ 0.1 | <1.0g |
| Comparative example 2 | 88.00 | 99.5 | ＜ 0.1 | <1.0g |
| Comparative example 3 | 89.33 | 99.4 | ＜ 0.1 | <1.0g |
| Comparative example 4 | 87.33 | 99.1 | ＜ 0.1 | <1.0g |
By comparative example 1- comparative examples 3 compared with embodiment 1- embodiments 6, the present invention prepares m-nitro
During formaldehyde, if the ratio of copper nitrate and benzaldehyde is too small (such as comparative example 1-2), benzaldehyde reaction is incomplete,
The yield of nitrobenzaldehyde is relatively low；If the ratio of copper nitrate and benzaldehyde is too big (such as comparative example 3-4), benzaldehyde can be fully
Reaction, but the yield of m-nitrobenzaldehyde not but not has more preferable raising, but also can generate some side reactions, leads to yield
With the decline of quality, it can be seen that, the mol ratio of copper nitrate and benzaldehyde is selected as 1.03-1.1：1.0.
Implement with reference to the prior art (content of background technology), comparative example 1- comparative examples 3 and embodiment 1-
Example 6 is it is found that the present invention has following technique effect：
1st, raw material is easy to get, and production cost is low.
2nd, processing step is simplified, and technological parameter is easy to control, with short production cycle, convenient for industrialized production.
3rd, the high income (being higher than 90%) of m-nitrobenzaldehyde, chromatographic purity is more than 99.8%, and o-nitrobenzaldehyde contains
Measure ＜ 0.1%.
4th, it filters mother liquid obtained can realize in the Kocide SD precipitation and third step that are generated in production technology and recycles profit
With, and the three wastes are few, pollution is few, environmentally protective.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, that is made any repaiies
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (7)
1. a kind of synthetic method of m-nitrobenzaldehyde, which is characterized in that include the following steps：
Step 1：Reaction, specifically：Copper nitrate, water and silver nitrate are added in reaction unit, is warming up to 70 DEG C -80 DEG C；It is added dropwise
Benzaldehyde, time for adding are 1.8-2.5 hours；85 DEG C -95 DEG C are warming up to, heat preservation obtains reaction mixture in 2-3 hours；From reaction
Sampling carries out chromatography detection in mixed liquor, and the mass content of benzaldehyde is less than 0.5%, wherein copper nitrate, water, silver nitrate and benzene
The mol ratio of formaldehyde is 1.03-1.1：20-40：0.001-0.0012：1.0；
Step 2：M-nitrobenzaldehyde crude product processed, specifically：Reaction mixture is filtered to remove Kocide SD at 85 DEG C -95 DEG C
Precipitation obtains mother liquor；Mother liquor is cooled to 10 DEG C -20 DEG C；Solid is filtered to take up to m-nitrobenzaldehyde crude product, it is described between nitro
The mass content of o-nitrobenzaldehyde is less than 0.5% in benzaldehyde crude product；
Step 3：M-nitrobenzaldehyde processed, specifically：M-nitrobenzaldehyde crude product is packed into reaction unit, adds in m-nitro
The water-soluble solvent of 3.0-3.5 times of formaldehyde crude product volume, is warming up to 50 DEG C -55 DEG C；Filtering remove add in after insoluble impurity it is water-soluble
The water of property solvent same volume；Filtering is dried after taking out the solid being precipitated to get m-nitrobenzaldehyde.
2. the synthetic method of m-nitrobenzaldehyde according to claim 1, which is characterized in that the nitric acid in the step 1
Copper, silver nitrate, benzaldehyde quality standard be general industry grade standard.
3. the synthetic method of m-nitrobenzaldehyde according to claim 1, which is characterized in that be equipped in the reaction unit
Mixing component, the stir speed (S.S.) of mixing component is 120-160 revs/min in the step 1 and step 3.
4. the synthetic method of m-nitrobenzaldehyde according to claim 1, which is characterized in that dried in the step 3
Temperature is 40 DEG C -50 DEG C, and the time is 8-12 hours.
5. the synthetic method of m-nitrobenzaldehyde according to any one of claims 1-4, which is characterized in that described water-soluble
Property solvent any one of for methanol, ethyl alcohol, isopropanol, dimethylformamide and tetrahydrofuran.
6. the synthetic method of m-nitrobenzaldehyde according to claim 5, which is characterized in that further include recycling step, institute
State recycling step is specifically including recycling step A and recycling step B, the recycling step A：The hydroxide that second step is obtained
Copper precipitation is neutralized with nitric acid, by obtained copper nitrate solution for the reaction in the first step；The recycling step B is specific
It is：Filtered during third is walked it is mother liquid obtained be used as water-soluble solvent by processing, wherein, water quality content in treated mother liquor
Less than 10%.
7. the synthetic method of m-nitrobenzaldehyde according to claim 6, which is characterized in that female in the recycling step B
The processing step of liquid is specifically：Mother liquor is pumped into recycling design rectifying column, control temperature is no more than 60 DEG C, flows back by adjusting
Than the mass content of moisture being controlled 10% hereinafter, collecting midbarrel.
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| CN102329234A (en) * | 2011-06-24 | 2012-01-25 | 灌南伊斯特化工有限公司 | Production process of m-nitrobenzaldehyde |
| CN103467300A (en) * | 2013-08-19 | 2013-12-25 | 浙江工业大学 | Synthesizing method for o-nitrobenzaldehyde compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329234A (en) * | 2011-06-24 | 2012-01-25 | 灌南伊斯特化工有限公司 | Production process of m-nitrobenzaldehyde |
| CN103467300A (en) * | 2013-08-19 | 2013-12-25 | 浙江工业大学 | Synthesizing method for o-nitrobenzaldehyde compound |
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Address after: 414009 Yunxi Industrial Park, Yueyang, Hunan Applicant after: Hunan Ya Wang Pharmaceutical Technology Co., Ltd. Address before: 414009 Yunxi Industrial Park, Yueyang, Hunan Applicant before: Yueyang Yetop Fine Chemical Co., Ltd. |
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