CN108164421A - The preparation method of o-nitrobenzaldehyde - Google Patents
The preparation method of o-nitrobenzaldehyde Download PDFInfo
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- CN108164421A CN108164421A CN201711251648.6A CN201711251648A CN108164421A CN 108164421 A CN108164421 A CN 108164421A CN 201711251648 A CN201711251648 A CN 201711251648A CN 108164421 A CN108164421 A CN 108164421A
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- Prior art keywords
- nitrobenzaldehyde
- initiator
- hydrogen peroxide
- reaction
- preparation
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- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000003999 initiator Substances 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 16
- 125000006278 bromobenzyl group Chemical group 0.000 claims abstract description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 nitro cyclite Chemical group 0.000 claims abstract description 10
- 239000000428 dust Substances 0.000 claims abstract description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 239000012046 mixed solvent Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- XUZLXCQFXTZASF-UHFFFAOYSA-N nitro(phenyl)methanol Chemical group [O-][N+](=O)C(O)C1=CC=CC=C1 XUZLXCQFXTZASF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 12
- 239000006227 byproduct Substances 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 239000005416 organic matter Substances 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 9
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical group [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to medicine intermediate fields, disclose a kind of preparation method of o-nitrobenzaldehyde, including being 35 by mass ratio：26 ~ 28 ortho-methylnitrobenzene and bromine are dissolved in the in the mixed solvent of water and organic solvent, are heated to 55 ~ 65 DEG C, add in initiator and are reacted to color fade, generate one bromobenzyl of adjacent nitro and adjacent nitro cyclite；70 ~ 75 DEG C are heated to, adding hydrogen peroxide and initiator, the reaction was continued to color fade；Keep temperature-resistant, adding hydrogen peroxide and initiator, the reaction was continued to color fade；Keep temperature-resistant, adding hydrogen peroxide and initiator, the reaction was continued to color fade；It keeps temperature-resistant, hydrogen peroxide and initiator is added to keep the temperature 1.5 ~ 2.5h；Aqueous sodium carbonate is added in, one bromobenzyl of adjacent nitro is hydrolyzed into nitro alcohol；Add dust technology, nitro alcohol is oxidized to o-nitrobenzaldehyde.This method yield is higher, reduces the generation of organic matter by-product and the discharge capacity of inorganic salts (acid) waste water.
Description
Technical field
The present invention relates to the preparation field of medicine intermediate, more particularly to a kind of preparation method of o-nitrobenzaldehyde.
Background technology
In the preparation process of medicine intermediate o-nitrobenzaldehyde, bromine and ortho-methylnitrobenzene are used as former
Material, under the initiation of initiator, the bromide ion that bromine decomposites reacts generation adjacent nitro bromobenzyl with ortho-methylnitrobenzene, herein
In the process, if it is desired to the reaction was complete as possible for ortho-methylnitrobenzene, then can increase the amount of the bromine of addition, but when reaction reaches
Certain balance, the amount of increases bromine simply can't promote reaction to positive direction progress again, and the yield of reaction does not have bright
Aobvious promotion.
Invention content
Goal of the invention：For problems of the prior art, the present invention provides a kind of preparation side of o-nitrobenzaldehyde
Method, this method yield is higher, reduces the generation of organic matter by-product and the discharge capacity of inorganic salts (acid) waste water.
Technical solution：The present invention provides a kind of preparation methods of o-nitrobenzaldehyde, include the following steps：S1：By matter
Amount is than being 35：26 ~ 28 ortho-methylnitrobenzene and bromine is dissolved in the in the mixed solvent of water and organic solvent and adds in mixed solution
Into reaction kettle, 55 ~ 65 DEG C are heated to, initiator is added in and is reacted to color fade, generation one bromobenzyl of adjacent nitro and adjacent nitre
Base cyclite；S2：70 ~ 75 DEG C are heated to, adding hydrogen peroxide and initiator, the reaction was continued to color fade；S3：Keep temperature-resistant,
Adding hydrogen peroxide and initiator, the reaction was continued to color fade；S4：It keeps temperature-resistant, adds hydrogen peroxide and initiator the reaction was continued extremely
Color fade；S5：It keeps temperature-resistant, hydrogen peroxide and initiator is added to keep the temperature 1.5 ~ 2.5h；S6：Aqueous sodium carbonate is added in, it will
System temperature is controlled at 90 ~ 100 DEG C, and one bromobenzyl of adjacent nitro is hydrolyzed into nitro alcohol；S7：Add in dust technology, body
It is that temperature is controlled at 65 ~ 70 DEG C, the nitro alcohol is oxidized to o-nitrobenzaldehyde.
Further, after the S7, S8 is further included：The o-nitrobenzaldehyde is extracted, is remained after extraction
Under mother liquor in add in sodium hydrate aqueous solution, the adjacent nitro cyclite is hydrolyzed into o-nitrobenzaldehyde.Extract adjacent nitro
Adjacent nitro cyclite after benzaldehyde in remaining mother liquor hydrolyzes generation product o-nitrobenzaldehyde by sodium hydrate aqueous solution, carries
High W-response yield.
Preferably, in the S8, a concentration of the 50% of the sodium hydrate aqueous solution.
Preferably, in the S6, a concentration of the 14% of the aqueous sodium carbonate.
Preferably, in the S7, a concentration of the 60% of the dust technology.
Preferably, the organic solvent is dichloroethanes.
Preferably, the initiator is EHP.
Advantageous effect：In the present invention, with excessive bromine under the initiation of initiator bromination occurs for ortho-methylnitrobenzene
It reacts to the color fade of bromine（Illustrate that bromine reacts away completely）, generate one bromobenzyl of adjacent nitro and adjacent nitro cyclite and pair
Then product hydrobromic acid adds in hydrogen peroxide and initiator for the first time, with byproduct hydrobromic acid oxidation reaction can occur for hydrogen peroxide,
Bromide ion in hydrobromic acid is oxidized to bromine, bromine can continue to that substitution reaction occurs up to bromine with ortho-methylnitrobenzene again
Color fade；Similarly, second, third time, the 4th addition hydrogen peroxide and initiator, due to the use of hydrogen peroxide so that most
Whole ortho-methylnitrobenzene can react completely, while promote substitution reaction and carried out to positive direction；When ortho-methylnitrobenzene reacts completely
Fall and then add in aqueous sodium carbonate, one bromobenzyl of adjacent nitro therein is carbonated sodium water solution hydrolysis generation product adjacent nitro
Benzyl alcohol and by-product sodium bromide, nitro alcohol are oxidized to required product o-nitrobenzaldehyde by dust technology again, then
O-nitrobenzaldehyde is extracted.
This method improves product yield and purity, and relatively industrial conventional method improves nearly 1.5 times to yield at present, and this method is total
Yield reaches 65 ~ 75%, and product purity is more than 99.5%；
This method oxidation technology can carry out under low pressure, and the reaction time shortens, the mild conditions such as reaction temperature；
The method reduces the generation of organic matter by-product and inorganic salts (acid) wastewater discharges；
This method can efficiently use molecular bromine, reduce the consumption of bromine；
Bromination and hydrolysis are completed in same reactor in this method, easy to operate；
This method can preparative separation go out high-purity medicine intermediate o-nitrobenzaldehyde.
Specific embodiment
The present invention is described in detail With reference to embodiment.
Embodiment 1：
Ortho-methylnitrobenzene 350 ㎏ and bromine 260kg are dissolved in the solvent of 700 ㎏ of water and 900 ㎏ of dichloroethanes compositions, and are fallen
Enter in 3000 liters of reaction kettle, be heated to 55 ~ 65 DEG C, add in 10 ㎏ of initiator and reacted to color fade, generate adjacent nitro
One bromobenzyl and adjacent nitro cyclite；70 ~ 75 DEG C are heated to, adding hydrogen peroxide 100 ㎏ and initiator 5kg for the first time, the reaction was continued to face
Color takes off；Keep temperature-resistant, adding hydrogen peroxide 100 ㎏ and initiator 5kg for the second time, the reaction was continued to color fade；Keep temperature
Constant, third time adds hydrogen peroxide 80kg and initiator 3kg to color fade；Keep temperature-resistant, the 4th time plus hydrogen peroxide 60kg
2h is kept the temperature with after 2 ㎏ of initiator；Then add in the aqueous sodium carbonate of 1800kg a concentration of 14%, system temperature control 90 ~
100 DEG C, one bromobenzyl of adjacent nitro is hydrolyzed into nitro alcohol；Then the dust technology of 400kg a concentration of 60%, system temperature are added in
Nitro alcohol is oxidized to o-nitrobenzaldehyde by degree control at 65 ~ 70 DEG C；Finally the o-nitrobenzaldehyde of generation is extracted
Out, and after extraction the sodium hydrate aqueous solution of 100kg a concentration of 50% is added in remaining mother liquor, by adjacent nitro therein
Cyclite is hydrolyzed into o-nitrobenzaldehyde.Finally it there are product o-nitrobenzaldehyde 227.5kg.Reaction yield is 65%.
Embodiment 2：
Ortho-methylnitrobenzene 350 ㎏ and bromine 270kg are dissolved in the solvent of 700 ㎏ of water and 900 ㎏ of dichloroethanes compositions, and are fallen
Enter in 3000 liters of reaction kettle, be heated to 55 ~ 65 DEG C, add in 10 ㎏ of initiator and reacted to color fade, generate adjacent nitro
One bromobenzyl and adjacent nitro cyclite；70 ~ 75 DEG C are heated to, adding hydrogen peroxide 100 ㎏ and initiator 5kg for the first time, the reaction was continued to face
Color takes off；Keep temperature-resistant, adding hydrogen peroxide 100 ㎏ and initiator 5kg for the second time, the reaction was continued to color fade；Keep temperature
Constant, third time adds hydrogen peroxide 80kg and initiator 3kg to color fade；Keep temperature-resistant, the 4th time plus hydrogen peroxide 60kg
2h is kept the temperature with after 2 ㎏ of initiator；Then add in the aqueous sodium carbonate of 1600kg a concentration of 14%, system temperature control 90 ~
100 DEG C, one bromobenzyl of adjacent nitro is hydrolyzed into nitro alcohol；Then the dust technology of 350kg a concentration of 60%, system temperature are added in
Nitro alcohol is oxidized to o-nitrobenzaldehyde by degree control at 65 ~ 70 DEG C；Finally the o-nitrobenzaldehyde of generation is extracted
Out, and after extraction the sodium hydrate aqueous solution of 120kg a concentration of 50% is added in remaining mother liquor, by adjacent nitro therein
Cyclite is hydrolyzed into o-nitrobenzaldehyde.Finally it there are product o-nitrobenzaldehyde 245kg.Reaction yield is 70%.
Embodiment 3：
Ortho-methylnitrobenzene 350 ㎏ and bromine 280kg are dissolved in the solvent of 700 ㎏ of water and 900 ㎏ of dichloroethanes compositions, and are fallen
Enter in 3000 liters of reaction kettle, be heated to 55 ~ 65 DEG C, add in 10 ㎏ of initiator and reacted to color fade, generate adjacent nitro
One bromobenzyl and adjacent nitro cyclite；70 ~ 75 DEG C are heated to, adding hydrogen peroxide 100 ㎏ and initiator 5kg for the first time, the reaction was continued to face
Color takes off；Keep temperature-resistant, adding hydrogen peroxide 100 ㎏ and initiator 5kg for the second time, the reaction was continued to color fade；Keep temperature
Constant, third time adds hydrogen peroxide 80kg and initiator 3kg to color fade；Keep temperature-resistant, the 4th time plus hydrogen peroxide 60kg
2h is kept the temperature with after 2 ㎏ of initiator；Then add in the aqueous sodium carbonate of 1500kg a concentration of 14%, system temperature control 90 ~
100 DEG C, one bromobenzyl of adjacent nitro is hydrolyzed into nitro alcohol；Then the dust technology of 330kg a concentration of 60%, system temperature are added in
Nitro alcohol is oxidized to o-nitrobenzaldehyde by degree control at 65 ~ 70 DEG C；Finally the o-nitrobenzaldehyde of generation is extracted
Out, and after extraction the sodium hydrate aqueous solution of 150kg a concentration of 50% is added in remaining mother liquor, by adjacent nitro therein
Cyclite is hydrolyzed into o-nitrobenzaldehyde.Finally it there are product o-nitrobenzaldehyde 262.5kg.Reaction yield is 75%.
The technical concepts and features of the above embodiment only to illustrate the invention, its object is to allow be familiar with technique
People can understand present disclosure and implement according to this, and it is not intended to limit the scope of the present invention.It is all according to the present invention
The equivalent transformation or modification that Spirit Essence is done, should be covered by the protection scope of the present invention.
Claims (7)
1. a kind of preparation method of o-nitrobenzaldehyde, which is characterized in that include the following steps：
S1：It is 35 by mass ratio：26 ~ 28 ortho-methylnitrobenzene and bromine is dissolved in the in the mixed solvent of water and organic solvent and will be mixed
It closes solution to be added in reaction kettle, is heated to 55 ~ 65 DEG C, add in initiator and reacted to color fade, generate adjacent nitro one
Bromobenzyl and adjacent nitro cyclite；
S2：70 ~ 75 DEG C are heated to, adding hydrogen peroxide and initiator, the reaction was continued to color fade；
S3：Keep temperature-resistant, adding hydrogen peroxide and initiator, the reaction was continued to color fade；
S4：Keep temperature-resistant, adding hydrogen peroxide and initiator, the reaction was continued to color fade；
S5：It keeps temperature-resistant, hydrogen peroxide and initiator is added to keep the temperature 1.5 ~ 2.5h；
S6：Aqueous sodium carbonate is added in, system temperature is controlled at 90 ~ 100 DEG C, and one bromobenzyl of adjacent nitro is hydrolyzed into adjacent nitro
Benzyl alcohol；
S7：Dust technology is added in, system temperature is controlled at 65 ~ 70 DEG C, and the nitro alcohol is oxidized to o-nitrobenzaldehyde.
2. the preparation method of o-nitrobenzaldehyde according to claim 1, which is characterized in that after the S7, also wrap
Include S8：The o-nitrobenzaldehyde is extracted, adds in sodium hydrate aqueous solution in remaining mother liquor after extraction, by described in
Adjacent nitro cyclite is hydrolyzed into o-nitrobenzaldehyde.
3. the preparation method of o-nitrobenzaldehyde according to claim 2, which is characterized in that in the S8, the hydrogen
A concentration of the 50% of aqueous solution of sodium oxide.
4. the preparation method of o-nitrobenzaldehyde according to claim 1, which is characterized in that in the S6, the carbon
A concentration of the 14% of acid sodium aqueous solution.
5. the preparation method of o-nitrobenzaldehyde according to claim 1, which is characterized in that described dilute in the S7
A concentration of the 60% of nitric acid.
6. the preparation method of o-nitrobenzaldehyde according to any one of claim 1 to 5, which is characterized in that described to have
Solvent is dichloroethanes.
7. the preparation method of o-nitrobenzaldehyde according to any one of claim 1 to 5, which is characterized in that described to draw
Hair agent is EHP.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711251648.6A CN108164421A (en) | 2017-12-01 | 2017-12-01 | The preparation method of o-nitrobenzaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711251648.6A CN108164421A (en) | 2017-12-01 | 2017-12-01 | The preparation method of o-nitrobenzaldehyde |
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| Publication Number | Publication Date |
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| CN108164421A true CN108164421A (en) | 2018-06-15 |
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| CN201711251648.6A Pending CN108164421A (en) | 2017-12-01 | 2017-12-01 | The preparation method of o-nitrobenzaldehyde |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947848A (en) * | 2018-08-07 | 2018-12-07 | 安庆市长虹化工有限公司 | A kind of nitrification installation and nitration processes method of o-nitrobenzaldehyde preparation |
| CN109810002A (en) * | 2019-02-14 | 2019-05-28 | 安徽泰格生物技术股份有限公司 | A kind of method that useless bromobenzyl prepares benzylamine |
| CN110655457A (en) * | 2019-09-05 | 2020-01-07 | 门希国 | Novel method for preparing p-fluorobenzaldehyde by catalytic oxidation of hydrogen peroxide |
| CN118652181A (en) * | 2024-08-20 | 2024-09-17 | 天津凯莱英医药科技发展有限公司 | A method and continuous device for continuously synthesizing o-nitrobenzyl bromide |
-
2017
- 2017-12-01 CN CN201711251648.6A patent/CN108164421A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947848A (en) * | 2018-08-07 | 2018-12-07 | 安庆市长虹化工有限公司 | A kind of nitrification installation and nitration processes method of o-nitrobenzaldehyde preparation |
| CN109810002A (en) * | 2019-02-14 | 2019-05-28 | 安徽泰格生物技术股份有限公司 | A kind of method that useless bromobenzyl prepares benzylamine |
| CN110655457A (en) * | 2019-09-05 | 2020-01-07 | 门希国 | Novel method for preparing p-fluorobenzaldehyde by catalytic oxidation of hydrogen peroxide |
| CN118652181A (en) * | 2024-08-20 | 2024-09-17 | 天津凯莱英医药科技发展有限公司 | A method and continuous device for continuously synthesizing o-nitrobenzyl bromide |
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Application publication date: 20180615 |