CN102924304A - Preparation method of m-dimethylaminophenol - Google Patents
Preparation method of m-dimethylaminophenol Download PDFInfo
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- CN102924304A CN102924304A CN2012104140115A CN201210414011A CN102924304A CN 102924304 A CN102924304 A CN 102924304A CN 2012104140115 A CN2012104140115 A CN 2012104140115A CN 201210414011 A CN201210414011 A CN 201210414011A CN 102924304 A CN102924304 A CN 102924304A
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- dimethylaminophenol
- resorcinol
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- dimethylamine
- preparation
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Abstract
The invention relates to a preparation method of m-dimethylaminophenol. The preparation method comprises the following steps of putting resorcinol and benzyl triethylamine served as a catalyst into a reaction container according to a mass ratio of 1:(0.003-0.005), wherein the pressure of nitrogen in the reaction container always keeps 1.8+/-0.2mPa; heating the reaction container to melt resorcinol totally, and starting stirring; adding dimethylamine to resorcinol in the reaction container, wherein the mass ratio of dimethylamine to resorcinol is 1:(0.4-0.6), and the temperature of the inside of the reaction container is controlled below 160 DEG; after dimethylamine is totally added, increasing the temperature of the inside of the reaction container to be 190+/-10 DEG and then keeping the temperature to react for 3 hours; carrying out vacuum distillation on the reaction products, and adding methylbenzene to m-dimethylaminophenol crude product after the vacuum distillation, wherein the mass ratio of methylbenzene to m-dimethylaminophenol crude product is 1:(1.0-1.6); heating under the normal pressure stirring conditions to totally dissolve the crude products, cooling down so that a great amount of white crystal is separated, filtering, and drying after taking out a filter cake to obtain m-dimethylaminophenol. The preparation method of m-dimethylaminophenol disclosed by the invention has the advantages of short process route, no pollution, more than 99% of product purity and stable product quality.
Description
Technical fieldThe present invention relates to a kind of preparation method of fine chemical product.
Background technologyBetween dimethyl phenol be high-quality fine chemical product, its preparation method is roughly as follows: become the m-dimethyl amino Phenylsulfonic acid by N, accelerine through sulfonation, form through alkali fusion.The m-dimethylaminophenol that adopts the method to obtain can be used as the intermediate of electron stain intermediate and makeup, and it also can be used for the intermediate of synthetic ophthalmic medicine dedicated, but can not use because its purity is low.
Summary of the inventionThe object of the present invention is to provide a kind of purity height can treat the preparation method of the m-dimethylaminophenol of eye illness pharmaceutical intermediate.
Raw material of the present invention has Resorcinol (preferably purity is more than 98%), dimethylamine (preferably purity is more than 98%) and benzyl Triethylamine catalyst, three's mass ratio is Resorcinol: dimethylamine: benzyl Triethylamine catalyst=1:0.4-0.6:0.003-0.005.
Of the present invention being prepared as follows:
1, Resorcinol and benzyl Triethylamine catalyst are dropped in the reaction vessel, and pass into nitrogen in container, the control nitrogen flow makes the pressure in the container remain at 1.8mPa ± 0.2.
2, treating that nitrogen is filled finishes the post-heating container, and the Resorcinol in the container is melted gradually, and Resorcinol all melts when temperature is raised to 120 ℃ of left and right sides, starts stirring.
3, the Resorcinol that melts in the container slowly adds dimethylamine, and temperature will remain at below 160 ℃ in the control container.After dimethylamine all adds, slowly be warmed up to 190 ℃ ± 10 ℃ insulation reaction 3 hours, afterwards naturally cooling.The water vapour and the low boilers that produce between this reaction period are all drained by venting port.
4, above-mentioned reaction product is moved in the distil container, carry out vacuum distilling under agitation condition, vacuum tightness reaches-0.098mpa ± 0.002, when temperature has m-dimethylaminophenol to steam and collects at 160 ℃.
5, the overhead product that obtains to above-mentioned vacuum distilling is to add toluene in the m-dimethylaminophenol crude product, both mass ratioes are m-dimethylaminophenol crude product: toluene=1:1.0-1.6, heating is all dissolved crude product under the normal pressure agitation condition, then cooling, then there are a large amount of white crystals to separate out, filter, get filtration cakes torrefaction, getting outward appearance is the xln of white, and purity is greater than 99%.
The present invention compared with prior art has following advantage:
1, operational path of the present invention is short, pollution-free, product purity is high and constant product quality, foreign matter content are low, and product crude product purity has just reached 95%, and through refining, purity reaches (chromatography) more than 99%, and the acetonitrile insolubles is less than 0.2%.2, the present invention " three wastes " discharging trends towards minimizing, and easily administers, and compares with the old technique of classics, and waste water, the waste residue of production have reduced 90%, particularly can not produce the byproduct of unsaleable adjacent hydroxyl dimethylamino phenol.
Embodiment
Example 1
Be that 99% 225g Resorcinol and 1g benzyl Triethylamine catalyst join in the 500ml autoclave with purity, and pass into nitrogen in container, the control nitrogen flow makes the pressure in the container remain at 1.6mPa.Treat that nitrogen is filled and finish the post-heating container, Resorcinol in it melts gradually, when being warmed up to 120 ℃, Resorcinol starts stirring after all dissolving, slowly add purity in the Resorcinol that melts in the container and be 98.5% dimethylamine 110g, the control amount of filling keeps the interior temperature of container below 160 ℃.After all adding, dimethylamine slowly is warmed up to 200 ℃ of insulation reaction 3 hours, afterwards naturally cooling.Above-mentioned reaction product is moved in the there-necked flask, slowly heat up under agitation condition and carry out vacuum distilling, vacuum tightness-0.1mpa is when temperature has water to steam at 60 ℃, when temperature has m-dimethylaminophenol to steam and collects at 160 ℃.In the m-dimethylaminophenol crude product of distillation acquisition, add toluene, both mass ratioes are m-dimethylaminophenol: toluene=1:1, normal pressure stir lower heating, and the m-dimethylaminophenol crude product is all dissolved, then cooling, then there are a large amount of white particulate materials to separate out, filter, get the filter cake seasoning and get the xln dry product 130g that outward appearance is white, again the toluene in the filtrate is steamed, residuum cools off seasoning again, can obtain again the 17g outward appearance and be the xln dry product of white, and dry product adds up to: 147g.Through its purity of gas chromatographic detection more than or equal to 99.0%.
Example 2
Be that 99.5% 225g Resorcinol and 1g benzyl Triethylamine catalyst join in the 500ml autoclave with purity, and pass into nitrogen in container, the control nitrogen flow makes the pressure in the container remain at 2.0mPa.Treat that nitrogen is filled and finish the post-heating container, Resorcinol in it melts gradually, when being warmed up to 120 ℃, Resorcinol starts stirring after all dissolving, slowly add purity in the Resorcinol that melts in the container and be 99% dimethylamine 110g, the control amount of filling keeps the interior temperature of container below 160 ℃.After all adding, dimethylamine slowly is warmed up to 180 ℃ of insulation reaction 3 hours, afterwards naturally cooling.Above-mentioned reaction product is moved in the there-necked flask, slowly heat up under agitation condition and carry out vacuum distilling, vacuum tightness-0.096mpa is when temperature has water to steam at 60 ℃, when temperature has m-dimethylaminophenol to steam and collects at 160 ℃.In the m-dimethylaminophenol crude product of distillation acquisition, add toluene, both mass ratioes are m-dimethylaminophenol: toluene=1:1.6, normal pressure stir lower heating, and the m-dimethylaminophenol crude product is all dissolved, then cooling, then there are a large amount of white particulate materials to separate out, filter, get the filter cake seasoning and get the xln dry product 102g that outward appearance is white, again the toluene in the filtrate is steamed, residuum cools off seasoning again, can obtain again the 11g outward appearance and be the xln dry product of white, and dry product adds up to: 113g.Through its purity of gas chromatographic detection more than or equal to 99.2%.
Claims (3)
1. the preparation method of a m-dimethylaminophenol is characterized in that:
1) be Resorcinol in mass ratio with Resorcinol and benzyl Triethylamine catalyst: benzyl Triethylamine catalyst=1:0.003-0.005 drops in the reaction vessel, and in container, pass into nitrogen, the control nitrogen flow makes the pressure in the container remain at 1.8mPa ± 0.2;
2), treat that nitrogen is filled and finish the post-heating container, the Resorcinol in the container is melted gradually, and Resorcinol starts stirring after all melting when temperature is raised to 120 ℃ of left and right sides;
3) Resorcinol that, melts in the container slowly adds dimethylamine, both mass ratioes are Resorcinol: dimethylamine=1:0.4-0.6, and temperature will remain at below 160 ℃ in the control container, after dimethylamine all adds, slowly be warmed up to 190 ℃ ± 10 ℃ insulation reaction 3 hours, afterwards naturally cooling;
4), above-mentioned reaction product is moved in the distil container, carry out vacuum distilling under agitation condition, vacuum tightness reaches-0.098mpa ± 0.002, when temperature has m-dimethylaminophenol to steam and collects at 160 ℃;
5) overhead product that, obtains to above-mentioned vacuum distilling is to add toluene in the m-dimethylaminophenol crude product, both mass ratioes are m-dimethylaminophenol crude product: toluene=1:1.0-1.6, heating is all dissolved crude product under the normal pressure agitation condition, then cooling, then there are a large amount of white crystals to separate out, filter, get filtration cakes torrefaction.
2. the preparation method of m-dimethylaminophenol according to claim 1, it is characterized in that: the toluene in the step 5) filtrate is steamed, residuum cools off seasoning more again.
3. the preparation method of m-dimethylaminophenol according to claim 1 and 2, it is characterized in that: the purity of Resorcinol and dimethylamine is all more than 98%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104140115A CN102924304A (en) | 2012-10-26 | 2012-10-26 | Preparation method of m-dimethylaminophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104140115A CN102924304A (en) | 2012-10-26 | 2012-10-26 | Preparation method of m-dimethylaminophenol |
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| CN102924304A true CN102924304A (en) | 2013-02-13 |
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| CN2012104140115A Withdrawn CN102924304A (en) | 2012-10-26 | 2012-10-26 | Preparation method of m-dimethylaminophenol |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154743A (en) * | 1977-02-11 | 1979-05-15 | Ciba-Geigy Corporation | 3-Oxobenzofuranyl-2-idenyl, haloacetic acids |
| GB1575860A (en) * | 1977-03-31 | 1980-10-01 | Hoechst Ag | Process for the manufacture of m-aminophenols |
| US5130489A (en) * | 1986-06-26 | 1992-07-14 | Indspec Chemical Corporation | Process for the preparation of M-aminophenols from resorcinol |
| JPH0585994A (en) * | 1991-09-30 | 1993-04-06 | Mitsui Petrochem Ind Ltd | Production of n,n-dialkylaminophenols |
| CN102381993A (en) * | 2011-12-02 | 2012-03-21 | 青岛俪徕精细化工有限公司 | Preparation method of 3-(N,N-dimethylamino)phenol |
-
2012
- 2012-10-26 CN CN2012104140115A patent/CN102924304A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154743A (en) * | 1977-02-11 | 1979-05-15 | Ciba-Geigy Corporation | 3-Oxobenzofuranyl-2-idenyl, haloacetic acids |
| GB1575860A (en) * | 1977-03-31 | 1980-10-01 | Hoechst Ag | Process for the manufacture of m-aminophenols |
| US5130489A (en) * | 1986-06-26 | 1992-07-14 | Indspec Chemical Corporation | Process for the preparation of M-aminophenols from resorcinol |
| JPH0585994A (en) * | 1991-09-30 | 1993-04-06 | Mitsui Petrochem Ind Ltd | Production of n,n-dialkylaminophenols |
| CN102381993A (en) * | 2011-12-02 | 2012-03-21 | 青岛俪徕精细化工有限公司 | Preparation method of 3-(N,N-dimethylamino)phenol |
Non-Patent Citations (1)
| Title |
|---|
| 曹广宏: "苄基三乙基氯化铵的制备及其在有机合成中的应用", 《辽宁化工》 * |
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Application publication date: 20130213 |
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