CN102344372A - Synthetic method of o-nitrophenol and o-nitroanisole - Google Patents
Synthetic method of o-nitrophenol and o-nitroanisole Download PDFInfo
- Publication number
- CN102344372A CN102344372A CN2011102151089A CN201110215108A CN102344372A CN 102344372 A CN102344372 A CN 102344372A CN 2011102151089 A CN2011102151089 A CN 2011102151089A CN 201110215108 A CN201110215108 A CN 201110215108A CN 102344372 A CN102344372 A CN 102344372A
- Authority
- CN
- China
- Prior art keywords
- nitrochlorobenzene
- methyl ether
- sodium hydroxide
- reaction
- synthesis method
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 title claims abstract description 19
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 title abstract 3
- 238000010189 synthetic method Methods 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002994 raw material Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001308 synthesis method Methods 0.000 claims description 11
- 230000033444 hydroxylation Effects 0.000 claims description 6
- 238000005805 hydroxylation reaction Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a synthetic method of o-nitrophenol and o-nitroanisole, which comprises the following steps: 1) taking o-nitrochlorobenzene, water and sodium hydroxide as raw materials to react in a reaction vessel for synthesizing o-nitrophenol; 2) taking o-nitrochlorobenzene, methanol and sodium hydroxide as raw materials to react for synthesizing o-nitroanisole. The invention has the advantages of less reaction pollution, simple process, easy operation, low cost, raised content of main product, high product purity and high yield.
Description
Technical field
The invention belongs to the compound field, be specifically related to the synthesis method of a kind of o-NP and o-Nitrophenyl methyl ether.
Background technology
O-NP is the raw material of synthetic Ortho-Aminophenol.Because of the Ortho-Aminophenol extensive market, demand is big, makes more people's research and improves the synthetic of o-NP.The o-NP synthetic effect is subjected to obviously influencing of sodium hydroxide concentration, aqueous sodium hydroxide solution concentration, temperature of reaction and reaction times.Feedstock conversion usually takes place finish, but product yield is low and the phenomenon of colour-difference.Have a strong impact on production stability.
O-Nitrophenyl methyl ether is the main raw material of synthetic dyestuff intermediate Fast Red B base.Because of demand is big, also there is more people to study the synthesis method of improvement o-Nitrophenyl methyl ether.The unsteady phenomenon of productive rate and quality also usually takes place in the o-Nitrophenyl methyl ether production process.Its reason also is because the fluctuation of reaction conditions causes the generation of side reaction.
Summary of the invention
The present invention provides the synthesis method of a kind of o-NP and o-Nitrophenyl methyl ether, and it is simple that it has technology, and is easy to operate, and product purity is high, the advantage that yield is high.
For achieving the above object, the present invention adopts following technical scheme:
The synthesis method of a kind of o-NP and o-Nitrophenyl methyl ether comprises:
1. in reaction kettle, be that raw material reacts synthetic o-NP with o-Nitrochlorobenzene, water and sodium hydroxide;
2. be that raw material reacts synthetic o-Nitrophenyl methyl ether at reaction kettle with o-Nitrochlorobenzene, methyl alcohol and sodium hydroxide.
Its reaction equation is following:
The mol ratio of said 1. o-Nitrochlorobenzene and sodium hydroxide is 1: 1.7-4.0, preferred molar ratio is 1: 1-3.0.
The concentration of said 2. used sodium hydroxide in water or in the methyl alcohol is 3-30%, and preferred concentration range for is 6-20%.
Said 1., 2. the temperature of reaction of o-Nitrochlorobenzene hydroxylation and methyl-etherified is 130-180 ℃ the reaction times is 2-8 hour, and preferable reaction temperature is 140-160 ℃.
Said 1., 2. o-Nitrochlorobenzene hydroxylation and methyl-etherified to react used protective material be oxygenant, its molecular formula can be expressed as AmBnCt, A, B are metallic element or non-metallic element, C is a non-metallic element.The m value is 0-2, and the n value is 0-2, and the t value is 1-7, and preferred oxidant is to choose any one kind of them in potassium permanganate, sodium dichromate 99, Manganse Dioxide, potassium bromate, clorox, ydrogen peroxide 50, oxygen, air, the chlorine or several.
Said 1., 2. o-Nitrochlorobenzene hydroxylation and the methyl-etherified 5-50% that to react used protectant consumption be the o-Nitrochlorobenzene mole number.
Advantage of the present invention: this method reaction is polluted few, and technology is simple, and is easy to operate, and cost is low, has improved the content of principal product, and product purity is high, and yield is high.
Embodiment
Embodiment one:
In the 1L autoclave pressure, drop into o-Nitrochlorobenzene 125 grams, water 512 grams, solid sodium hydroxide 102.4 grams, 8.5 grams, 35% ydrogen peroxide 50.In 145-165 ℃ of reaction 4 hours.Reaction is finished, and after the cooling material is poured in the beaker, transfers PH most 5 with sulfuric acid, in 50 ℃ of standing demix, obtains oil reservoir and carries out underpressure distillation and get product o-NP 107.8 grams, GC purity 99.7%.
Embodiment two:
In the 1L autoclave pressure, drop into o-Nitrochlorobenzene 45 grams, water 540 grams, solid sodium hydroxide 22.5 grams, blowing air is to 0.35-0.4Mpa in still.Heat up then in 145-165 ℃ of reaction 4 hours.Reaction is finished, and after the cooling material is poured in the beaker, transfers PH most 5 with sulfuric acid, in 50 ℃ of standing demix, obtains oil reservoir and carries out underpressure distillation and get product o-NP 39 grams, GC purity 99.8%.
Embodiment three:
In the 1L autoclave pressure, drop into o-Nitrochlorobenzene 45 grams, methyl alcohol 435 grams, solid sodium hydroxide 37.5 grams, blowing air is to 0.35-0.4Mpa in still.Heat up then in 115-135 ℃ of reaction 8 hours.Reaction is finished, and concentrates to remove methyl alcohol.In resistates, add water,, obtain oil reservoir and carry out underpressure distillation and get product o-Nitrophenyl methyl ether 42.7 gram, GC purity 99.6% in 30 ℃ of standing demix.
The above; Only be the specific embodiment of the present invention, but protection scope of the present invention is not limited thereto, any technician who is familiar with the present technique field is in the technical scope that the present invention discloses; Can expect easily changing or replacement, all should be encompassed within protection scope of the present invention.Therefore, protection scope of the present invention should be as the criterion with the protection domain of said claim.
Claims (6)
1. the synthesis method of o-NP and o-Nitrophenyl methyl ether is characterized in that, comprising:
1. in reaction kettle, be that raw material reacts synthetic o-NP with o-Nitrochlorobenzene, water and sodium hydroxide;
2. be that raw material reacts synthetic o-Nitrophenyl methyl ether at reaction kettle with o-Nitrochlorobenzene, methyl alcohol and sodium hydroxide.
Its reaction equation is following:
2. the synthesis method of a kind of o-NP according to claim 1 and o-Nitrophenyl methyl ether is characterized in that: the mol ratio of said 1. o-Nitrochlorobenzene and sodium hydroxide is 1: 1.7-4.0.
3. the synthesis method of a kind of o-NP according to claim 1 and o-Nitrophenyl methyl ether is characterized in that: the concentration of said 2. used sodium hydroxide in water or in the methyl alcohol is 3-30%.
4. the synthesis method of a kind of o-NP according to claim 1 and o-Nitrophenyl methyl ether is characterized in that: said 1., 2. the temperature of reaction of o-Nitrochlorobenzene hydroxylation and methyl-etherified is 130-180 ℃, the reaction times is 2-8 hour.
5. the synthesis method of a kind of o-NP according to claim 1 and o-Nitrophenyl methyl ether; It is characterized in that: said 1., 2. o-Nitrochlorobenzene hydroxylation and methyl-etherified to react used protective material be oxygenant; Its molecular formula can be expressed as AmBnCt; A, B are metallic element or non-metallic element, and C is a non-metallic element.The m value is 0-2, and the n value is 0-2, and the t value is 1-7.
6. the synthesis method of a kind of o-NP according to claim 1 and o-Nitrophenyl methyl ether is characterized in that: said 1., 2. o-Nitrochlorobenzene hydroxylation and the methyl-etherified 5-50% that to react used protectant consumption be the o-Nitrochlorobenzene mole number.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011102151089A CN102344372A (en) | 2011-07-29 | 2011-07-29 | Synthetic method of o-nitrophenol and o-nitroanisole |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011102151089A CN102344372A (en) | 2011-07-29 | 2011-07-29 | Synthetic method of o-nitrophenol and o-nitroanisole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102344372A true CN102344372A (en) | 2012-02-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011102151089A Pending CN102344372A (en) | 2011-07-29 | 2011-07-29 | Synthetic method of o-nitrophenol and o-nitroanisole |
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| CN (1) | CN102344372A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108047065A (en) * | 2017-12-11 | 2018-05-18 | 江苏中丹化工技术有限公司 | A kind of preparation method for the adjacent amino phenylate for reducing by-product |
| CN114736128A (en) * | 2022-03-10 | 2022-07-12 | 青岛科技大学 | A kind of method for preparing o-aminophenyl ether |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3283011A (en) * | 1962-02-21 | 1966-11-01 | Universal Oil Prod Co | Preparation of nitrophenols |
| DE1543952A1 (en) * | 1966-10-27 | 1970-02-12 | Universal Oil Prod Co | Process for the production of nitrophenols |
| CN1962593A (en) * | 2006-11-24 | 2007-05-16 | 王在军 | Pyrocatechin and hydroquinone production process |
| CN101643419A (en) * | 2008-08-08 | 2010-02-10 | 夏恩将 | Method for preparing o-nitroanisole |
-
2011
- 2011-07-29 CN CN2011102151089A patent/CN102344372A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3283011A (en) * | 1962-02-21 | 1966-11-01 | Universal Oil Prod Co | Preparation of nitrophenols |
| DE1543952A1 (en) * | 1966-10-27 | 1970-02-12 | Universal Oil Prod Co | Process for the production of nitrophenols |
| CN1962593A (en) * | 2006-11-24 | 2007-05-16 | 王在军 | Pyrocatechin and hydroquinone production process |
| CN101643419A (en) * | 2008-08-08 | 2010-02-10 | 夏恩将 | Method for preparing o-nitroanisole |
Non-Patent Citations (1)
| Title |
|---|
| 王风阁: "合成邻氨基苯甲醚的反应条件的研究", 《烟台师范学院学报(自然科学版)》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108047065A (en) * | 2017-12-11 | 2018-05-18 | 江苏中丹化工技术有限公司 | A kind of preparation method for the adjacent amino phenylate for reducing by-product |
| CN108047065B (en) * | 2017-12-11 | 2019-02-12 | 江苏中丹化工技术有限公司 | A kind of preparation method of o-aminophenyl ether that can reduce by-product |
| CN114736128A (en) * | 2022-03-10 | 2022-07-12 | 青岛科技大学 | A kind of method for preparing o-aminophenyl ether |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120208 |