CN101941912A - Method for refining high-purity N,N-dihydroxy ethyl para-toluidine - Google Patents
Method for refining high-purity N,N-dihydroxy ethyl para-toluidine Download PDFInfo
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- CN101941912A CN101941912A CN2010102653822A CN201010265382A CN101941912A CN 101941912 A CN101941912 A CN 101941912A CN 2010102653822 A CN2010102653822 A CN 2010102653822A CN 201010265382 A CN201010265382 A CN 201010265382A CN 101941912 A CN101941912 A CN 101941912A
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- toluidine
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- dihydroxyethyl
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Abstract
The invention relates to a method for refining high-purity N,N-dihydroxy ethyl para-toluidine, which comprises the following steps: orderly adding para-methylaniline, sodium hydroxide and methanol into the reaction kettle, heating to 50-80 DEG C while stirring, adding a composite aminolysis initiator while keeping the temperature constant, gradually adding chloroethanol, keeping the temperature to react for 2-5 hours, and stopping heating; and cooling to room temperature, filtering and distilling to obtain the finished product of N,N-dihydroxy ethyl para-toluidine. The method prepares N,N-dihydroxy ethyl para-toluidine by using a direct process; the composite aminolysis initiator is added in the reaction process, thereby shortening the aminolysis reaction time of the raw materials to about 2-5 hours and enhancing the production efficiency; and after aminolysis reaction, the purification by filtering, distillation and the like increases the purity of the product.
Description
Technical field
The invention belongs to the organic compound preparation field, relate to the preparation method of a kind of tackiness agent and sealing agent, especially a kind of high-purity N, the process for purification of N-dihydroxyethyl p-toluidine.
Background technology
N, N-dihydroxyethyl p-toluidine (DEPT) is applicable to industrial tamanori and seal applications, also be suitable for building and dentistry tamanori, it is general to have many uses, N in addition, N-dihydroxyethyl p-toluidine (DEPT) is the production of unsaturated polyester or acrylic resin, a kind of anti-xanthochromia solution is provided, can substitute traditional catalyzer, it is coating material solidified that it also is used for UV (ultraviolet ray), the preparation of tackiness agent and sealing agent has higher energy use efficiency, solidify in the industrial production at chemical catalysis, N, the N-dihydroxyethyl p-toluidine has the catalytic curing performance as a kind of important organic compound, application more and more widely.
N, the present production method of N-dihydroxyethyl p-toluidine is: by parachlorotoluene and N, it is synthetic that the N-diethanolamine carries out aminolysis, the problem that this preparation method exists: be difficult to control when 1, carrying out owing to this reaction, reaction times reaches nearly hundred hours, and terminal point is indeterminate; 2, raw materials used N, the N-diethanolamine is difficult to obtain, and production cost is high.Therefore, there is the problem that the production time is long, production efficiency is low and cost is high in aforesaid method, is unfavorable for the raising of business economic benefit.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art part, provide a kind of reaction times short, raw materials cost is low, the high-purity N of production efficiency, the process for purification of N-dihydroxyethyl p-toluidine.
The objective of the invention is to be achieved through the following technical solutions:
A kind of high-purity N, the process for purification of N-dihydroxyethyl p-toluidine, it is characterized in that: may further comprise the steps: in reactor, drop into successively monomethylaniline, sodium hydroxide, methyl alcohol, stirring and be heated to 50-85 ℃, the compound aminolysis initiator of temperature-resistant adding, add chloroethanol more gradually, chloroethanol added the back insulation reaction 2-5 hour, stopped heating; Be cooled to room temperature, more after filtration, the distillation filtrate, promptly get N, N-dihydroxyethyl p-toluidine finished product;
Described compound aminolysis initiator consist of potassiumiodide: lithium iodide: zinc iodide=1: 0.05: 0.1 (m/m/m);
Described to monomethylaniline: chloroethanol: sodium hydroxide: methyl alcohol=1: 3.65: 2: 4.1 (m/m/m/m);
Described compound aminolysis initiator: to monomethylaniline=0.35-0.5: 1 (m/m).
And described reactor has heating unit, electric whipping appts and temperature measuring equipment.
Advantage of the present invention and positively effect are:
1, this high-purity N, the process for purification of N-dihydroxyethyl p-toluidine uses the direct method preparation, add a kind of compound aminolysis initiator in the reaction process, add the aminolysis reaction time that has effectively shortened each raw material behind the compound aminolysis initiator, reaction times reduced to about 2-5 hour, had improved production efficiency, behind the aminolysis reaction after filtration with the purifying of steps such as distillation, improve degree of purity of production, met industrial requirements.
2, the raw material that uses of this process for purification is all raw material commonly used in the chemical industry, and wide material sources not only, and cheap have effectively lowered N, the production cost of N-dihydroxyethyl p-toluidine, and using widely for it provides prerequisite and basis.
3, this high-purity N, the process for purification reaction principle of N-dihydroxyethyl p-toluidine is clear and definite, step is simple, working condition is gentle, raw material sources are extensive, is convenient to realize suitability for industrialized production.
Embodiment
The invention will be further described below by specific embodiment, and following examples are descriptive, is not determinate, can not limit protection scope of the present invention with this.
The used product of following examples is all commercially available.
Embodiment 1
A kind of high-purity N, the process for purification of N-dihydroxyethyl p-toluidine may further comprise the steps:
(1) aminolysis reaction step
Have heating unit to one, electricity stirs, and drops into to monomethylaniline 1000 grams sodium hydroxide 2000 grams in 10 liters of reactors of thermometer successively, methyl alcohol 4100 grams, under agitation be heated to 55 ± 2 ℃ of reactions simultaneously, keep this state of temperature, add compound aminolysis initiator 350 grams, constantly add chloroethanol 3650 grams, chloroethanol added the back insulation reaction 2 hours, stopped heating, and aminolysis reaction stops;
Wherein, compound aminolysis initiator consist of potassiumiodide: lithium iodide: zinc iodide=1: 0.05: 0.1 (m/m/m);
To monomethylaniline: chloroethanol: sodium hydroxide: methyl alcohol=1: 3.65: 2: 4.1 (m/m/m/m);
Compound aminolysis initiator: to monomethylaniline=0.35-0.5: 1 (m/m);
Temperature of reaction is 50-85 ℃ and all can.
(2) filtration step
The mixed solution that obtains behind the aminolysis reaction is cooled to room temperature, filters, collect filtrate, filtrate is oily liquids;
(3) distilation steps
Filtrate is distilled, and 170--185 ℃ of distillatory temperature and 10 ± 2mmHg obtain product N, the N-dihydroxyethyl p-toluidine.
After testing, the N that present embodiment makes, N-dihydroxyethyl p-toluidine, its content 99.0-99.5%.
Embodiment 2
A kind of high-purity N, the process for purification of N-dihydroxyethyl p-toluidine may further comprise the steps:
(1) aminolysis reaction step
Have heating unit to one, electricity stirs, drop into successively in 10 liters of reactors of thermometer monomethylaniline 1000 grams, sodium hydroxide 2000 grams, methyl alcohol 4100 grams under agitation are heated to 55 ± 2 ℃ of reactions simultaneously, keep this state of temperature, add compound aminolysis initiator 380 grams, constantly add chloroethanol 3650 grams, chloroethanol added the back insulation reaction 2 hours.Stop heating, aminolysis reaction stops.
(2) filtration step
The mixed solution that obtains behind the aminolysis reaction is cooled to room temperature, filters, collect filtrate, filtrate is oily liquids;
(3) distilation steps
Filtrate is distilled, and 170--185 ℃ of distillatory temperature and 10 ± 2mmHg obtain product, N, N-dihydroxyethyl p-toluidine.
After testing, the N that present embodiment makes, N-dihydroxyethyl p-toluidine, its content 99.0--99.5%.
Embodiment 3
A kind of high-purity N, the process for purification of N-dihydroxyethyl p-toluidine may further comprise the steps:
(1) aminolysis reaction step
Have heating unit to one, electricity stirs, drop into successively in 10 liters of reactors of thermometer monomethylaniline 1000 grams, sodium hydroxide 2000 grams, methyl alcohol 4100 grams under agitation are heated to 55 ± 2 ℃ of reactions simultaneously, keep this state of temperature, add compound aminolysis initiator 400 grams, constantly add chloroethanol 3650 grams, chloroethanol added the back insulation reaction 2 hours.Stop heating, aminolysis reaction stops.
(2) filtration step
The mixed solution that obtains behind the aminolysis reaction is cooled to room temperature, filters, collect filtrate, filtrate is oily liquids;
(3) distilation steps
Filtrate is distilled, and 170--185 ℃ of distillatory temperature and 10 ± 2mmHg obtain product N, the N-dihydroxyethyl p-toluidine.
After testing, the N that present embodiment makes, N-dihydroxyethyl p-toluidine, its content 99.0-99.5%.
Claims (2)
1. high-purity N, the process for purification of N-dihydroxyethyl p-toluidine, it is characterized in that: may further comprise the steps: in reactor, drop into successively monomethylaniline, sodium hydroxide, methyl alcohol, stirring and be heated to 50-85 ℃, the compound aminolysis initiator of temperature-resistant adding, add chloroethanol more gradually, chloroethanol added the back insulation reaction 2-5 hour, stopped heating; Be cooled to room temperature, more after filtration, the distillation filtrate, promptly get N, N-dihydroxyethyl p-toluidine finished product;
Described compound aminolysis initiator consist of potassiumiodide: lithium iodide: zinc iodide=1: 0.05: 0.1 (m/m/m);
Described to monomethylaniline: chloroethanol: sodium hydroxide: methyl alcohol=1: 3.65: 2: 4.1 (m/m/m/m);
Described compound aminolysis initiator: to monomethylaniline=0.35-0.5: 1 (m/m).
2. high-purity N according to claim 1, the process for purification of N-dihydroxyethyl p-toluidine is characterized in that: described reactor has heating unit, electric whipping appts and temperature measuring equipment.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2010102653822A CN101941912A (en) | 2010-08-28 | 2010-08-28 | Method for refining high-purity N,N-dihydroxy ethyl para-toluidine |
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| CN2010102653822A CN101941912A (en) | 2010-08-28 | 2010-08-28 | Method for refining high-purity N,N-dihydroxy ethyl para-toluidine |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1743364A (en) * | 2004-09-04 | 2006-03-08 | 兰爱克谢斯德国有限责任公司 | Specific mixtures of n,n-bis(2-hydroxyalkyl)-4-toluidine derivatives, their preparation and a method of using such specific mixtures |
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- 2010-08-28 CN CN2010102653822A patent/CN101941912A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1743364A (en) * | 2004-09-04 | 2006-03-08 | 兰爱克谢斯德国有限责任公司 | Specific mixtures of n,n-bis(2-hydroxyalkyl)-4-toluidine derivatives, their preparation and a method of using such specific mixtures |
Non-Patent Citations (5)
| Title |
|---|
| 《广州化工》 19830402 阮邦球等 N,N-二-(alpha-羟乙基)-对-甲苯胺的合成 第63页 1-2 , * |
| YUEE YAN ET AL.: "A novel azathia-crown ether dye chromogenic chemosensor for the selective detection of mercury(II) ion", 《DYES AND PIGMENTS》, vol. 79, 18 January 2008 (2008-01-18), pages 210 - 215, XP022640134, DOI: doi:10.1016/j.dyepig.2008.01.003 * |
| 师华等: "芳胺的N-烷基化反应", 《精细化工中间体》, vol. 38, no. 6, 28 December 2008 (2008-12-28), pages 8 - 11 * |
| 钟爱民等: "具有高二阶极化率噻唑类生色分子的合成与表征", 《化学学报》, vol. 64, no. 4, 28 February 2006 (2006-02-28), pages 343 - 347 * |
| 阮邦球等: "N,N-二-(α-羟乙基)-对-甲苯胺的合成", 《广州化工》, 2 April 1983 (1983-04-02), pages 63 * |
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Application publication date: 20110112 |