CN103951604A - Method for separation and purification of indole - Google Patents
Method for separation and purification of indole Download PDFInfo
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- CN103951604A CN103951604A CN201410142972.4A CN201410142972A CN103951604A CN 103951604 A CN103951604 A CN 103951604A CN 201410142972 A CN201410142972 A CN 201410142972A CN 103951604 A CN103951604 A CN 103951604A
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- indoles
- polar solvent
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- indole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for separation and purification of indole comprises: utilizing mixed methylnaphthalene with the indole content of 4-6% or vessel residual oil with the indole content of 8-30% and obtained after beta-methylnaphthalene is extracted, mixing with a nonpolar solvent according to a certain ratio, then employing a polar solvent to perform first extraction, so as to obtain a heavy phase rich in indole and a light phase containing a small amount of residual indole; adding a certain ratio of water into the heavy phase, then utilizing a nonpolar solvent to perform secondary extraction on the water-added heavy phase, so as to obtain a heavy phase (when the solvent content is not calculated) with the indole content of 85% or more (corresponding to the mixed methylnaphthalene raw material) or the indole content of 99% or more (corresponding to the vessel residual oil raw material); and performing rectification separation on the heavy phase obtained through secondary extraction, so as to obtain a polar solvent contains no indole and crude indole with the indole content of 85% or more or the indole finished product with the indole content of 99% or more. The technology is simple in process, short in flow, high in indole recovery rate and low in production cost.
Description
Technical field
The present invention relates to a kind of method of indoles Separation & Purification of field of coal tar deep processing, specifically, relate to the method for Separation & Purification indoles a kind of still Residual oil after mixed methylnaphthalene or extraction beta-methylnaphthalene.
Background technology
About the leaching process of indoles, existing many patents or documents and materials, wherein typically comprise: the way with solvent pairs (polar solvent and non-polar solvent) extracting and separating indoles, highly efficient distilling purification indoles that application number 200410066250.1 is mentioned; The permanent good fortune of water etc. is mentioned in " coal tar separates with refining ", can in polar solvent, add water to improve the selectivity of indoles extraction process, and the way of mentioning with application number 200410066250.1 is similar; Application number 200410066247.X has proposed the method for the separating indole of saline extraction, way by salt adding in the aqueous solution of alcohol, glycol or alcamines is to improve the selectivity of solvent to indoles, thereby in raising extraction phase, indoles content is (while referring to disregard the content of solvent and salt, lower same), to reduce follow-up indoles rectifying separation difficulty.
Above-mentioned disclosed patent application data and patent in the past mainly concentrate on selectivity how to pass through to improve solvent, thereby indoles content or reduce the content of the neutral substances such as methylnaphthalene in extraction phase in raising extraction phase, thereby reduce follow-up indoles rectifying separation difficulty.Problem is, in any case, in the extraction phase that above-mentioned separation method obtains, indoles content can only reach the mixed methylnaphthalene raw material of 45～65%(corresponding to indoles content 4～6%) or 60～80%(corresponding to the still residual feedstocks of indoles content 8～30%), need to indoles content be improved to 90～95% by follow-up highly efficient distilling, and then by the way of solvent crystallization, further to improve indoles content.Because indoles is that methylnaphthalene, biphenyl etc. exist azeotropic problem with major impurity wherein, above-mentioned rectifying difficulty is very large, and yield generally only has 30～60%, and is all to operate under large reflux ratio, and energy consumption is very high; Equally, the devices such as follow-up crystallization needs are freezing, solvent Distillation recovery, energy consumption is also very high.Certainly, also can utilize above-mentioned 45～80% indoles fractions more than a step rectifying to 99%, but in separation principle, there is no material alterations, actual recovery is also lower.For the disclosed saline extraction way of 200410066247.X, also reluctant problem in the production of one, inevitable area, be exactly how salt reclaims, salt in pyrogenic distillation process the problem such as the heavy corrosion to equipment, saline crystallization difficulty of transportation.Generally speaking, there is complex technical process, Production Flow Chart is long, facility investment is large, production cost is high, process yield is low problem in above-mentioned extracting process, on producing, there is no practical significance, so that so far there are no industrialized report.
Summary of the invention
The present invention adds a certain proportion of water in the heavy phase after single extraction, then remove the neutral impurity such as methylnaphthalene, biphenyl wherein by the way of reextraction, thereby directly obtain the heavy phase (while referring to disregard solvent) of indoles content more than 85% (corresponding to mixed methylnaphthalene raw material) or 99% above (corresponding to still residual feedstocks).Because the method process efficiency is high, select common cheap non-polar solvent just can reach extraordinary effect, significantly shorten technical process, improve process yield, thereby greatly save production cost, indoles extractive technique is of practical significance, and has set up at home first cover industrialized unit.
Preferred embodiment is:
Technical scheme 1: a kind of method of indoles Separation & Purification, comprising following steps: the mixed methylnaphthalene that utilizes indoles content 3～6% is raw material, mix with non-polar solvent by a certain percentage, then carry out single extraction with polar solvent, obtain being rich in the heavy phase of indoles and the light phase containing a small amount of remaining indoles; In heavy phase, add the water of 0.1～0.7 times, then the heavy phase adding water is carried out to reextraction, the above product of indoles content 85% while obtaining disregarding solvent with non-polar solvent; Then the rectifying separation that heavy phase reextraction being obtained is carried out, obtains not polar solvent and the more than 85% thick indoles of content containing indoles.
Technical scheme 2: a kind of method of indoles Separation & Purification, comprising following steps: utilizing the still Residual oil after the extraction beta-methylnaphthalene of indoles content 8～30% is raw material, mix with non-polar solvent by a certain percentage, then carry out single extraction with polar solvent, obtain being rich in the heavy phase of indoles and the light phase containing a small amount of remaining indoles; In heavy phase, add the water of 0.1～0.7 times, then the heavy phase adding water is carried out to reextraction with non-polar solvent, more than 99% heavy phase of indoles content while obtaining disregarding solvent (; Then the rectifying separation that heavy phase reextraction being obtained is carried out, obtains not polar solvent and the more than 99% indoles finished product of content containing indoles.
The method of indoles Separation & Purification described in technical scheme 1 or 2, described polar solvent is triglycol, ethylene glycol, dimethyl sulfoxide (DMSO) or thanomin; Described non-polar solvent is the kerosene, 200 of 160～200 DEG C of boiling points
#solvent oil, octane or sherwood oil.
The method of indoles Separation & Purification described in technical scheme 1 or 2, described polar solvent consumption is 0.3～1.0 times of indoles raw material, the consumption of non-polar solvent is 0.3～1.5 times of indoles raw material; In described reextraction, the consumption of non-polar solvent is heavy phase 0.5～3.0 times.
The method of indoles Separation & Purification described in technical scheme 1 or 2, described single extraction or reextraction, be all the counter-current extraction carrying out in the extraction plant of 3～20 grades.
Embodiment
Embodiment 1:
The still residual feedstocks of indoles content 8%, with the kerosene of 160～200 DEG C of the boiling points of 0.3 times of triglycol and 0.7 times, carry out single extraction, extraction progression is 3 grades, in the heavy phase obtaining, add the water of 0.4 times, then carry out reextraction with the kerosene of 1.0 times, extraction progression is 4 grades, when gained heavy phase indoles content reaches 99.0%(and refers to disregard wherein water and solvent), obtain 99.0% finished product indoles through dephlegmate and solvent.
Embodiment 2:
The mixed methylnaphthalene raw material of indoles content 3%, with 200 of 1.0 times of ethylene glycol and 0.3 times
#solvent oil, carries out single extraction, extraction progression be 20 grades, in the heavy phase obtaining, add the water of 0.1 times, and then with 0.5 times 200
#the capable reextraction of solvent oil, extraction progression is 15 grades, when gained heavy phase indoles content reaches 85.1%((and refers to disregard wherein water and solvent), obtain 85.1% thick indoles through dephlegmate and solvent.
Embodiment 3:
The still residual feedstocks of indoles content 30%, carry out single extraction with the octane of 0.7 times of dimethyl sulfoxide (DMSO) and 1.0 times, extraction progression is 10 grades, in the heavy phase obtaining, add the water of 0.7 times, and then carry out reextraction with the octane of 1.5 times, extraction progression is 12 grades, when gained heavy phase indoles content reaches 99.3%(and refers to disregard wherein water and solvent), obtain 99.3% finished product indoles through dephlegmate and solvent.
Embodiment 4:
The still residual feedstocks of indoles content 15%, carry out single extraction with the sherwood oil of 1.0 times of thanomins and 1.5 times, extraction progression is 6 grades, in the heavy phase obtaining, add the water of 0.4 times, and then carry out reextraction with the octane of 3.0 times, extraction progression is 7 grades, when gained heavy phase indoles content reaches 99.2%(and refers to disregard wherein water and solvent), obtain 99.2% finished product indoles through dephlegmate and solvent.
Comparative example 1:
Carry out single extraction by the raw material of embodiment 1 and condition, but do not carry out reextraction, in the heavy phase obtaining, indoles content is that 70%(is while referring to disregard wherein solvent), obtain 70% indoles fraction through dephlegmate and solvent, illustrate that, if without reextraction, indoles content does not far reach 99%.
Comparative example 2:
Carry out single extraction and reextraction by the raw material of embodiment 1 and condition, difference is, in reextraction process, do not add water, in the heavy phase obtaining, indoles content is that 91%(is while referring to disregard wherein solvent), remove desolventizing through distillation and obtain 91% indoles fraction, if illustrate that indoles content does not reach 99% yet if do not added water when reextraction.
Comparative example 3:
Carry out single extraction by the raw material of embodiment 2 and condition, but do not carry out reextraction, in the heavy phase obtaining, indoles content is that 47.0%(is while referring to disregard wherein solvent), obtain 47.0% indoles fraction through dephlegmate and solvent, illustrate that, if without reextraction, indoles content does not far reach 85%.
Comparative example 4:
Carry out single extraction and reextraction by the raw material of embodiment 2 and condition, difference is, in reextraction process, do not add water, in the heavy phase obtaining, indoles content is that 80.2%(is while referring to disregard wherein solvent), remove desolventizing through distillation and obtain 80.2% indoles fraction, if illustrate that indoles content does not reach 85% yet if do not added water when reextraction.
Claims (5)
1. the method for indoles Separation & Purification, comprising following steps: the mixed methylnaphthalene that utilizes indoles content 3～6% is raw material, mix with non-polar solvent by a certain percentage, then carry out single extraction with polar solvent, obtain being rich in the heavy phase of indoles and the light phase containing a small amount of remaining indoles; In heavy phase, add the water of 0.1～0.7 times, then the heavy phase adding water is carried out to reextraction, the above product of indoles content 85% while obtaining disregarding solvent with non-polar solvent; Then the rectifying separation that heavy phase reextraction being obtained is carried out, obtains not polar solvent and the more than 85% thick indoles of content containing indoles.
2. the method for indoles Separation & Purification, comprising following steps: utilizing the still Residual oil after the extraction beta-methylnaphthalene of indoles content 8～30% is raw material, mix with non-polar solvent by a certain percentage, then carry out single extraction with polar solvent, obtain being rich in the heavy phase of indoles and the light phase containing a small amount of remaining indoles; In heavy phase, add the water of 0.1～0.7 times, then the heavy phase adding water is carried out to reextraction with non-polar solvent, more than 99% heavy phase of indoles content while obtaining disregarding solvent (; Then the rectifying separation that heavy phase reextraction being obtained is carried out, obtains not polar solvent and the more than 99% indoles finished product of content containing indoles.
3. the method for indoles Separation & Purification described in claim 1 or 2, described polar solvent is triglycol, ethylene glycol, dimethyl sulfoxide (DMSO) or thanomin; Described non-polar solvent is the kerosene, 200 of 160～200 DEG C of boiling points
#solvent oil, octane or sherwood oil.
4. the method for indoles Separation & Purification described in claim 1 or 2, described polar solvent consumption is 0.3～1.0 times of indoles raw material, the consumption of non-polar solvent is 0.3～1.5 times of indoles raw material; In described reextraction, the consumption of non-polar solvent is heavy phase 0.5～3.0 times.
5. the method for indoles Separation & Purification described in claim 1 or 2, described single extraction or reextraction, be all the counter-current extraction carrying out in the extraction plant of 3～20 grades.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410142972.4A CN103951604B (en) | 2014-04-11 | 2014-04-11 | A kind of method of indoles Separation ＆ Purification |
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| CN201410142972.4A CN103951604B (en) | 2014-04-11 | 2014-04-11 | A kind of method of indoles Separation ＆ Purification |
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| CN103951604B CN103951604B (en) | 2018-08-28 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151226A (en) * | 2014-08-26 | 2014-11-19 | 江苏万年长药业有限公司 | Extracting recycle method of indole from indole synthesis waste water |
| CN104876847A (en) * | 2015-05-09 | 2015-09-02 | 辽宁科技学院 | Method for extracting indole from methyl naphthalene fraction |
| CN106631967A (en) * | 2016-12-20 | 2017-05-10 | 北京化工大学 | Method for extraction separation of indole from washing oil by quaternary ammonium salt extraction agent |
| CN112279799A (en) * | 2019-07-26 | 2021-01-29 | 中石化南京化工研究院有限公司 | Method for preparing spice-grade indole by extraction crystallization |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04356458A (en) * | 1990-04-27 | 1992-12-10 | Kawasaki Steel Corp | Extraction of indoles |
| WO2002068005A1 (en) * | 2001-02-26 | 2002-09-06 | The Procter & Gamble Company | Composition for aroma delivery with improved stability and reduced foaming |
| CN1746159A (en) * | 2004-09-09 | 2006-03-15 | 上海宝钢化工有限公司 | Indole separation and purification |
| CN1746158A (en) * | 2004-09-09 | 2006-03-15 | 上海宝钢化工有限公司 | indole salt-adding extraction separation method |
-
2014
- 2014-04-11 CN CN201410142972.4A patent/CN103951604B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04356458A (en) * | 1990-04-27 | 1992-12-10 | Kawasaki Steel Corp | Extraction of indoles |
| WO2002068005A1 (en) * | 2001-02-26 | 2002-09-06 | The Procter & Gamble Company | Composition for aroma delivery with improved stability and reduced foaming |
| CN1746159A (en) * | 2004-09-09 | 2006-03-15 | 上海宝钢化工有限公司 | Indole separation and purification |
| CN1746158A (en) * | 2004-09-09 | 2006-03-15 | 上海宝钢化工有限公司 | indole salt-adding extraction separation method |
Non-Patent Citations (1)
| Title |
|---|
| 肖瑞华: "《煤焦油化工学》", 28 February 2009 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104151226A (en) * | 2014-08-26 | 2014-11-19 | 江苏万年长药业有限公司 | Extracting recycle method of indole from indole synthesis waste water |
| CN104876847A (en) * | 2015-05-09 | 2015-09-02 | 辽宁科技学院 | Method for extracting indole from methyl naphthalene fraction |
| CN106631967A (en) * | 2016-12-20 | 2017-05-10 | 北京化工大学 | Method for extraction separation of indole from washing oil by quaternary ammonium salt extraction agent |
| CN106631967B (en) * | 2016-12-20 | 2019-03-29 | 北京化工大学 | A method of with indoles in Arquad extraction and separation washing oil |
| CN112279799A (en) * | 2019-07-26 | 2021-01-29 | 中石化南京化工研究院有限公司 | Method for preparing spice-grade indole by extraction crystallization |
| CN112279799B (en) * | 2019-07-26 | 2022-02-22 | 中石化南京化工研究院有限公司 | Method for preparing spice-grade indole by extraction crystallization |
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| CN103951604B (en) | 2018-08-28 |
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