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
- Publication number
- 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
- Authority
- CN
- China
- Prior art keywords
- toluidine
- aminolysis
- purity
- dihydroxyethyl
- initiator
- 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
- 238000000034 method Methods 0.000 title claims abstract description 18
- -1 ethyl para-toluidine Chemical compound 0.000 title abstract 4
- 238000007670 refining Methods 0.000 title abstract 2
- 238000007098 aminolysis reaction Methods 0.000 claims abstract description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 239000003999 initiator Substances 0.000 claims abstract description 15
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 238000000746 purification Methods 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 4
- VDMLVOIDGSOUTA-UHFFFAOYSA-N 2-(4-methylanilino)ethane-1,1-diol Chemical compound CC1=CC=C(NCC(O)O)C=C1 VDMLVOIDGSOUTA-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 13
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 11
- 239000000706 filtrate Substances 0.000 claims description 11
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 5
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 claims description 4
- 229960004839 potassium iodide Drugs 0.000 claims description 3
- 235000007715 potassium iodide Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 7
- 230000035484 reaction time Effects 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 238000004904 shortening Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000013019 agitation Methods 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 |
|---|---|---|---|
| CN2010102653822A CN101941912A (en) | 2010-08-28 | 2010-08-28 | Method for refining high-purity N,N-dihydroxy ethyl para-toluidine |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102653822A CN101941912A (en) | 2010-08-28 | 2010-08-28 | Method for refining high-purity N,N-dihydroxy ethyl para-toluidine |
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| Publication Number | Publication Date |
|---|---|
| CN101941912A true CN101941912A (en) | 2011-01-12 |
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| CN2010102653822A Pending 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 |
-
2010
- 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 |