CN104045522A - Method for extraction of 2,4,6-trimethylphenol from 2, 6-dimethylphenol waste - Google Patents
Method for extraction of 2,4,6-trimethylphenol from 2, 6-dimethylphenol waste Download PDFInfo
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- CN104045522A CN104045522A CN201410187094.8A CN201410187094A CN104045522A CN 104045522 A CN104045522 A CN 104045522A CN 201410187094 A CN201410187094 A CN 201410187094A CN 104045522 A CN104045522 A CN 104045522A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
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Abstract
The invention relates to a method for extraction of 2,4,6-trimethylphenol, and provides a method for extraction of the 2,4,6-trimethylphenol from 2, 6-dimethylphenol waste, and the method comprises the following steps: 1) decoloration, to be more specific, distillation treatment of the 2, 6-dimethylphenol waste is performed, and a distilled liquid is condensed to be used as a 2,4,6-trimethylphenol recovery crude product; 2) recrystallization, to be more specific, a solvent is tert butyl alcohol or cyclohexane or an ethanol and water mixture two-phase solvent; and 3) drying to obtain the finished product,. The method solves the problems that impurities in the 2, 6-dimethylphenol waste are close in boiling points and are difficult to separate by distillation, and the method has the advantages of mild conditions and simple recovery operation.
Description
Technical field
The present invention relates to a kind of extracting method of 2，4，6-trimethyl phenol, be specifically related to a kind of method environment-friendly type, extract 2，4，6-trimethyl phenol from 2,6-xylenol waste material.
Background technology
Current 2,4, the production method of 6-pseudocuminol is mainly: (1) take p-methyl phenol and methyl alcohol is raw material, under high temperature catalyst exists, the ortho-methylated reaction of hydroxyl generates 2,4,6-tri-cresols, the subject matter of this method is that production Raw cost is high, and complete processing is complicated, and equipment is once invested larger.Cost of goods manifactured is naturally also larger, ten thousand yuans of the 4-5 that approximately need per ton; (2) utilize principles of rectification to extract from coal tar, though also can extract, be difficult to obtain the finished product that purity is higher.
2,6-xylenol is for producing the monomer of polyphenylene oxide.2,6-xylenol is that to take phenol and methyl alcohol be raw material, and under the condition of high temperature and catalyzer, reaction makes.In reaction production process, except phenol conversion is for generating polyphenylene oxide monomer 2, outside 6-xylenol, also generate in a large number with 2,4,6-tri-cresols are main by product.Crude product after rectifying tower rectifying, obtain purity higher 2,6-xylenol, these by products are discharged through tower bottom of rectifying tower, and major ingredient is 2,6-xylenol, 2,4,6-pseudocuminol, 2,6-dimethylanisole, 2,4,6-Three methyl Benzene methyl ether, 2,3,6-pseudocuminol etc., complicated.Boiling point and 2 due to some impurity, 4,6-, tri-cresols boiling points are more approaching, if to obtain purity higher 2,4,6-pseudocuminol, but can not realize by the method for direct rectifying, is treated for many years with waste always, in order to reduce nature discharge, avoid causing environmental pollution, it is burnt in oil-firing boiler with low-grade fuel, this is also a kind of no small waste in fact.
Summary of the invention
Not enough for prior art, the object of this invention is to provide a kind of method of extracting 2，4，6-trimethyl phenol from 2,6-xylenol waste material.
For achieving the above object, the invention provides a kind of method of extracting 2，4，6-trimethyl phenol from 2,6-xylenol waste material, comprise the following steps:
1) decolouring: the distillation of 2,6-xylenol waste material is processed, and after distillate condensation, the crude product of 2，4，6-trimethyl phenol is reclaimed in conduct;
2) recrystallization: described solvent is the trimethyl carbinol or hexanaphthene or the mixed biphasic solvent of second alcohol and water;
3) dry, obtain finished product.
Preferably, step 1) distillation described in is under 120-200 ℃, the absolute pressure condition that is 3-15KPa in temperature, stirs, vacuum distilling.
Preferably, step 2) described in, in recrystallization process, by described crude product and solvent, be heated to 80-90 ℃, stop heating, crystallisation by cooling, when temperature is reduced to 0-20 ℃, filters, and obtains filter cake.
Preferably, filtrate is carried out recycled solvent.
Preferably, bake out temperature step 3) is 40-50 ℃.
Preferably, described step 2) after, also comprise repeatedly recrystallization.
Preferably, when solvent is the biphasic solvent of second alcohol and water, the usage ratio of etoh solvent and filter cake is 1:1, and the usage ratio of ethanol and water is 1:0.6～1.
Beneficial effect of the present invention: the invention solves in 2,6-xylenol waste material impurity boiling point close, be difficult to separated difficulty with rectifying, the method has mild condition, the simple advantage of reclaimer operation.
Embodiment
Following examples are used for illustrating the present invention, but are not used for limiting the scope of the invention.
Embodiment 1
By 800 gram 2,6-xylenol waste material joins in tower reactor 1000ml distillation tower, in temperature, is 120-200 ℃, under the condition that absolute pressure is 3-15KPa, and stirring, vacuum distilling.After distillate condensation, as the crude product that reclaims 2，4，6-trimethyl phenol, bottom product is returned to recycle bin.
Embodiment 2
The 2，4，6-trimethyl phenol crude product of getting 192 grams of decolourings (detects with gas-chromatography machine, the content of 2，4，6-trimethyl phenol in crude product is 71.95%), add in the there-necked flask of 1000ml, then add 128 grams of trimethyl carbinols, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 67 grams of filter cakes (containing 2,4,6-pseudocuminol 89.82%).
Gained filter cake is added to 45 grams of trimethyl carbinols, add in the there-necked flask of 1000ml, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the second time, filter, obtain 45 grams of filter cakes (containing 2,4,6-, tri-cresols 94.1%).
Embodiment 3
The 2，4，6-trimethyl phenol crude product of 100 grams of decolourings (is detected with gas-chromatography machine, the content of 2,4,6-, tri-cresols in crude product is 77.2%), add in the there-necked flask of 1000ml, then add 100 grams of hexanaphthenes, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 50 grams of filter cakes (containing 2,4,6-pseudocuminol 90.85%).
Gained filter cake is added to 50 grams of hexanaphthenes, add in the there-necked flask of 1000ml, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the second time, filter, obtain 39 grams of filter cakes (containing 2，4，6-trimethyl phenol 95.73%).
Embodiment 4
The 2，4，6-trimethyl phenol crude product of 100 grams of decolourings (is detected with gas-chromatography machine, the content of 2，4，6-trimethyl phenol in crude product is 77.2%), add in the there-necked flask of 1000ml, then add 100 grams of ethanol and 70 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 39 grams of filter cakes (containing 2,4,6-pseudocuminol 94.25%).
Embodiment 5
The 2，4，6-trimethyl phenol crude product of 100 grams of decolourings (is detected with gas-chromatography machine, the content of 2，4，6-trimethyl phenol in crude product is 77.2%), add in the there-necked flask of 1000ml, then add 100 grams of ethanol and 60 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 34 grams of filter cakes (containing 2,4,6-pseudocuminol 95.66%).
Embodiment 6
The 2，4，6-trimethyl phenol crude product of 100 grams of decolourings (is detected with gas-chromatography machine, the content of 2，4，6-trimethyl phenol in crude product is 84.64%), add in the there-necked flask of 1000ml, then add 100 grams of ethanol and 80 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 65 grams of filter cakes (containing 2,4,6-pseudocuminol 97.3%).
Embodiment 7
The 2，4，6-trimethyl phenol crude product of 100 grams of decolourings (is detected with gas-chromatography machine, the content of 2，4，6-trimethyl phenol in crude product is 84.64%), add in the there-necked flask of 1000ml, then add 100 grams of ethanol and 90 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 67 grams of filter cakes (containing 2,4,6-pseudocuminol 97.03%).
Embodiment 8
The 2，4，6-trimethyl phenol crude product of 100 grams of decolourings (is detected with gas-chromatography machine, the content of 2，4，6-trimethyl phenol in crude product is 82.17%), add in the there-necked flask of 1000ml, then add 100 grams of ethanol and 90 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the first time, filter, obtain 60 grams of filter cakes (containing 2,4,6-pseudocuminol 97.27%).
Embodiment 9
The intermediate that a recrystallization of the method gained of embodiment 8 is obtained, after mixing, (with gas-chromatography machine, detect, 2,4, the content of 6-pseudocuminol in crude product is 94.49%) get in 100 grams of there-necked flasks that join 1000ml, add again 100 grams of ethanol and 90 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization for the second time, filter, obtain 74 grams of filter cakes (containing 2,4,6-pseudocuminol 99.11%).
The filter cake of recrystallization gained is put into constant temperature convection oven and at 50 ℃, dry, dry 6 hours, obtain 55.3 grams of finished products.
Embodiment 10
Get 150 grams of finished products that obtain by the method for embodiment 9, join in the there-necked flask of 1000ml, then add 150 grams of ethanol and 120 grams of water, under stirring, be heated to 80 ℃, after insulation 10min, stop heating, with mixture of ice and water, condense to 15 ℃, carry out recrystallization, filter, obtain 110 grams of filter cakes (containing 2，4，6-trimethyl phenol 99.89%).
The filter cake of recrystallization gained is put into constant temperature convection oven, at 50 ℃, dry, dry 6 hours, obtain 57 grams of top grade product.
Although, above used general explanation, embodiment and test, the present invention is described in detail, on basis of the present invention, can make some modifications or improvements it, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements, all belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (7)
1. a method of extracting 2，4，6-trimethyl phenol from 2,6-xylenol waste material, is characterized in that, comprises the following steps:
1) decolouring: the distillation of 2,6-xylenol waste material is processed, and after distillate condensation, the crude product of 2，4，6-trimethyl phenol is reclaimed in conduct;
2) recrystallization: described solvent is the trimethyl carbinol or hexanaphthene or the mixed biphasic solvent of second alcohol and water;
3) dry, obtain finished product.
2. method according to claim 1, is characterized in that step 1) described in distillation in temperature, be under 120-200 ℃, the absolute pressure condition that is 3-15KPa, stir, vacuum distilling.
3. method according to claim 1 and 2, is characterized in that step 2) described in recrystallization process, by described crude product and solvent, be heated to 80-90 ℃, stop heating, crystallisation by cooling, when temperature is reduced to 0-20 ℃, filters, and obtains filter cake.
4. method according to claim 3, is characterized in that, filtrate is carried out recycled solvent.
5. method according to claim 1, is characterized in that step 3) described in bake out temperature be 40-50 ℃.
6. according to the arbitrary described method of claim 1-5, it is characterized in that described step 2) after, also comprise repeatedly recrystallization.
7. method according to claim 6, is characterized in that, when solvent is the biphasic solvent of second alcohol and water, the usage ratio of etoh solvent and filter cake is 1:1, and the usage ratio of ethanol and water is 1:0.6～1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410187094.8A CN104045522A (en) | 2014-05-05 | 2014-05-05 | Method for extraction of 2,4,6-trimethylphenol from 2, 6-dimethylphenol waste |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410187094.8A CN104045522A (en) | 2014-05-05 | 2014-05-05 | Method for extraction of 2,4,6-trimethylphenol from 2, 6-dimethylphenol waste |
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| CN104045522A true CN104045522A (en) | 2014-09-17 |
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| CN201410187094.8A Pending CN104045522A (en) | 2014-05-05 | 2014-05-05 | Method for extraction of 2,4,6-trimethylphenol from 2, 6-dimethylphenol waste |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558610A (en) * | 2018-04-28 | 2018-09-21 | 江苏焕鑫新材料股份有限公司 | A kind of enriching and purifying technique of low content 2,3,5- pseudocuminols |
| CN113736047A (en) * | 2020-05-29 | 2021-12-03 | 南通星辰合成材料有限公司 | Phenolic aldehyde modified amine curing agent taking industrial waste as raw material and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985812A (en) * | 1968-10-02 | 1976-10-12 | Continental Oil Company | Caustic refining of 2,3,6-trimethylphenol |
| CN1919817A (en) * | 2006-04-12 | 2007-02-28 | 哈尔滨市依兰中太化工有限公司 | 2,3,5-trimethylphenol and preparation method for the same |
-
2014
- 2014-05-05 CN CN201410187094.8A patent/CN104045522A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985812A (en) * | 1968-10-02 | 1976-10-12 | Continental Oil Company | Caustic refining of 2,3,6-trimethylphenol |
| CN1919817A (en) * | 2006-04-12 | 2007-02-28 | 哈尔滨市依兰中太化工有限公司 | 2,3,5-trimethylphenol and preparation method for the same |
Non-Patent Citations (2)
| Title |
|---|
| 张志德等: "2,6-二甲基苯酚的合成研究", 《精细与专用化学品》 * |
| 郗英欣等主编: "《有机化学实验》", 28 February 2014, 西安交通大学出版社 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558610A (en) * | 2018-04-28 | 2018-09-21 | 江苏焕鑫新材料股份有限公司 | A kind of enriching and purifying technique of low content 2,3,5- pseudocuminols |
| CN108558610B (en) * | 2018-04-28 | 2021-02-12 | 江苏焕鑫新材料股份有限公司 | Enrichment and purification process of low-content 2,3, 5-trimethylphenol |
| CN113736047A (en) * | 2020-05-29 | 2021-12-03 | 南通星辰合成材料有限公司 | Phenolic aldehyde modified amine curing agent taking industrial waste as raw material and preparation method thereof |
| CN113736047B (en) * | 2020-05-29 | 2024-04-16 | 南通星辰合成材料有限公司 | Phenolic aldehyde modified amine curing agent with industrial waste as raw material and preparation method thereof |
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