CN103288617A - Method for selectively adsorbing and separating acetophenone and alpha-methyl benzyl alcohol - Google Patents
Method for selectively adsorbing and separating acetophenone and alpha-methyl benzyl alcohol Download PDFInfo
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- CN103288617A CN103288617A CN2013101854461A CN201310185446A CN103288617A CN 103288617 A CN103288617 A CN 103288617A CN 2013101854461 A CN2013101854461 A CN 2013101854461A CN 201310185446 A CN201310185446 A CN 201310185446A CN 103288617 A CN103288617 A CN 103288617A
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- Prior art keywords
- methyl phenyl
- phenyl ketone
- beta
- cyclodextrin
- jia
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 title claims abstract description 122
- 238000000034 method Methods 0.000 title claims abstract description 26
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 title abstract description 7
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 title abstract 4
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 43
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 41
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract description 41
- 239000001116 FEMA 4028 Substances 0.000 claims abstract description 34
- 229960004853 betadex Drugs 0.000 claims abstract description 34
- 238000001179 sorption measurement Methods 0.000 claims abstract description 22
- 238000000926 separation method Methods 0.000 claims abstract description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 230000000274 adsorptive effect Effects 0.000 claims description 11
- 238000005194 fractionation Methods 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002594 sorbent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000003795 desorption Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000003463 adsorbent Substances 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 1
- GJSJZQZEDAUFBH-UHFFFAOYSA-N benzene;pentan-3-one Chemical compound CCC(=O)CC.C1=CC=CC=C1 GJSJZQZEDAUFBH-UHFFFAOYSA-N 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 244000167230 Lonicera japonica Species 0.000 description 1
- 235000017617 Lonicera japonica Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The method discloses a method for selectively adsorbing and separating acetophenone and alpha-methyl benzyl alcohol. Based on the characteristics of the difference of the adsorption capacity of beta-cyclodextrin to the acetophenone and the alpha-methyl benzyl alcohol, the insolubility of the beta-cyclodextrin in a mixing solution of the acetophenone and the alpha-methyl benzyl alcohol and the like, the purpose of separation and purification is realized by performing preferential adsorption on the acetophenone under an moderate condition by taking the beta-cyclodextrin as an adsorbent. The method is moderate in separation condition, good in separation effect, simple in process, energy-saving, environmental-friendly and the like; and the adsorbent can be used repeatedly.
Description
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Technical field
The present invention relates to the isolation technique of methyl phenyl ketone and α-Jia Jibianchun, specifically, relate to the method for a kind of selective adsorption separation of benzene ethyl ketone and α-Jia Jibianchun.
Background technology
Methyl phenyl ketone and α-Jia Jibianchun (having another name called the 1-phenylethyl alcohol) are important Organic Chemicals, are widely used in aspects such as spices and essence, medicine.Methyl phenyl ketone has as similar fragrance such as almond, cherry, Japanese Honeysuckle, jasmine and strawberry, therefore can be used as spice additive, and it still is a kind of important source material of synthetic pharmaceutical prod; α-Jia Jibianchun also can be widely used in industries such as medicine and spices.Contain a large amount of methyl phenyl ketones and α-Jia Jibianchun in some coarse raw materials, by product and the waste material of a lot of petrochemical enterprises, the total content of the two contains the methyl phenyl ketone of 75% mass content of having an appointment and the α-Jia Jibianchun of 18% mass content more than 90% usually such as producing in the cinnamic by product.Therefore, if can will have very significantly energy economy ﹠ environment benefit from methyl phenyl ketone and the 1-phenylethyl alcohol that wherein extracts higher degree.
Yet, the molecular structure of methyl phenyl ketone and α-Jia Jibianchun and physical properties are very approaching, such as, the boiling point of methyl phenyl ketone is 202 ℃, and the boiling point of α-Jia Jibianchun is 204 ℃, and the atmospheric boiling point difference has only 2 ℃, relative volatility is very little, under normal pressure or decompression, be easy to form azeotrope, adopt the means of rectifying that they are separated, need to consume very high energy.And both zero pour also are difficult to both are separated by the fusion-crystallization method also very near (being all 20 ℃).
(CN102627544A) openly in the patent of applicant's application early because thereby beta-cyclodextrin has high efficiency separation that the ability of selectivity inclusion methyl phenyl ketone can realize methyl phenyl ketone and α-Jia Jibianchun by the inclusion partition method.The inventive method proposes to compare more simple separation method with the inclusion partition method, and described method is directly used methyl phenyl ketone and the α-Jia Jibianchun in the beta-cyclodextrin powder fractionation by adsorption mixed solution.For the separation scheme of methyl phenyl ketone and 1-phenylethyl alcohol, the selective adsorption method that present method proposes can provide efficiently, the separating technology of environmental protection.
Summary of the invention
The object of the present invention is to provide the method for a kind of selective adsorption separation of benzene ethyl ketone and α-Jia Jibianchun.
To achieve these goals, the present invention adopts following technical scheme:
The method of a kind of fractionation by adsorption methyl phenyl ketone and α-Jia Jibianchun, be sorbent material with the beta-cyclodextrin, at the mixed solution that contains methyl phenyl ketone and α-Jia Jibianchun, under mild conditions, utilize the b-cyclodextrin that the difference of methyl phenyl ketone and α-Jia Jibianchun adsorptive power is realized both separation.
In the method for above-mentioned selective adsorption separation of benzene ethyl ketone and α-Jia Jibianchun mixture, adopt following steps: under 20 ~ 40 ℃, normal pressure, beta-cyclodextrin is joined in the mixed solution that contains methyl phenyl ketone and α-Jia Jibianchun, beta-cyclodextrin carries out preferentially adsorbed to methyl phenyl ketone, desorption is carried out with desorbing agent in the absorption back, and the beta-cyclodextrin after the recovery is reused.
In the method for above-mentioned selective adsorption separation of benzene ethyl ketone and α-Jia Jibianchun mixture, described mixed solution is to contain the aqueous solution of methyl phenyl ketone and α-Jia Jibianchun or contain methyl phenyl ketone and the water/ethanolic soln of α-Jia Jibianchun.The solvent that is described mixed solution is that water or water mix with ethanol.
In the method for above-mentioned selective adsorption separation of benzene ethyl ketone and α-Jia Jibianchun mixture, in the described mixed solution, the total content of methyl phenyl ketone and α-Jia Jibianchun is 10 g/L ~ 40 g/L.
In the method for above-mentioned selective adsorption separation of benzene ethyl ketone and α-Jia Jibianchun mixture, described desorbing agent is a kind of in ethyl acetate, methyl alcohol or the ethanol.
Compared with prior art, the present invention has following beneficial effect:
1. the present invention is sorbent material with the beta-cyclodextrin, utilize beta-cyclodextrin to the difference of methyl phenyl ketone and α-Jia Jibianchun adsorptive power and beta-cyclodextrin characteristics such as insoluble in methyl phenyl ketone and α-Jia Jibianchun mixing solutions, and realize that both separate in the selective adsorption under mild conditions.The present invention adopts gentle adsorptive separation technology, therefore, has avoided rectifying to separate shortcomings such as the very approaching methyl phenyl ketone of rerum natura and the existing energy consumption height of α-Jia Jibianchun, efficient are low with crystallization processes.
2. the present invention need not to make the water-soluble back of beta-cyclodextrin selectivity inclusion guest molecule, but beta-cyclodextrin directly is applied to the fractionation by adsorption of methyl phenyl ketone and α-Jia Jibianchun as a kind of sorbing material.
3. the recyclable repeated use of sorbent material beta-cyclodextrin of the present invention's employing, and its repeat performance is highly stable.
4. sorbent material beta-cyclodextrin of the present invention is cheap and easy to get, separating technology is simply gentle, easily realizes suitability for industrialized production.
Embodiment
The present invention is described further below in conjunction with embodiment and Comparative Examples, but protection scope of the present invention is not limited thereto.
Embodiment 1
1.135 g beta-cyclodextrins are put in the aqueous solution that 25 mL contain 5 g/L methyl phenyl ketones and 5 g/L α-Jia Jibianchuns, after vibration, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with ethyl acetate elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on beta-cyclodextrin is respectively 0.1055 g and 0.0505 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 0.78 g/L and 2.98 g/L in the debris, and the fractionation by adsorption factor is 9.05.
Embodiment 2
1.135 g beta-cyclodextrins are put in the aqueous solution that 25 mL contain 8 g/L methyl phenyl ketones and 8 g/L α-Jia Jibianchuns, after vibration, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with ethyl acetate elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on beta-cyclodextrin is respectively 0.1490g and 0.0334 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 2.04 g/L and 6.66 g/L in the debris, and the fractionation by adsorption factor is 14.56.
Embodiment 3
1.135 g beta-cyclodextrins are put in water/ethanolic soln that 25 mL contain 15 g/L methyl phenyl ketones and 15 g/L α-Jia Jibianchuns, after vibration, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with ethyl acetate elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on beta-cyclodextrin is respectively 0.1362 g and 0.0314 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 9.55 g/L and 13.74 g/L in the debris, and the fractionation by adsorption factor is 6.23.
Embodiment 4
1.135 g beta-cyclodextrins are put in the aqueous solution that 25 mL contain 8 g/L methyl phenyl ketones and 8 g/L α-Jia Jibianchuns, after stirring, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with ethyl acetate elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on beta-cyclodextrin is respectively 0.1471 g and 0.0332 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 2.12 g/L and 6.67 g/L in the debris, and the fractionation by adsorption factor is 13.95.
Embodiment 5
1.135 g beta-cyclodextrins are put in the aqueous solution that 25 mL contain 8 g/L methyl phenyl ketones and 8 g/L α-Jia Jibianchuns, after vibration, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with methyl alcohol elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on beta-cyclodextrin is respectively 0.1476 g and 0.0326 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 2.10 g/L and 6.70 g/L in the debris, and the fractionation by adsorption factor is 14.46.
Embodiment 6
1.135 g beta-cyclodextrins are put in the aqueous solution that 25 mL contain 4 g/L methyl phenyl ketones and 16 g/L α-Jia Jibianchuns, after vibration, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with ethyl acetate elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on the b-cyclodextrin is respectively 0.0594 g and 0.0515 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 1.62 g/L and 13.94 g/L in the debris, and the fractionation by adsorption factor is 10.07.
Embodiment 7
1.135 g beta-cyclodextrins are put in water/ethanolic soln that 25 mL contain 16 g/L methyl phenyl ketones and 4 g/L α-Jia Jibianchuns, after vibration, filtering, methyl phenyl ketone and the α-Jia Jibianchun that will be adsorbed on the beta-cyclodextrin with ethyl acetate elute under 30 ℃, normal pressure.Pass through gas chromatographic detection, methyl phenyl ketone and the α-Jia Jibianchun adsorptive capacity on beta-cyclodextrin is respectively 0.1492 g and 0.0011 g, the content of methyl phenyl ketone and α-Jia Jibianchun is respectively 10.03 g/L and 3.96 g/L in the debris, and the fractionation by adsorption factor is 53.23.
Claims (5)
1. the method for a fractionation by adsorption methyl phenyl ketone and α-Jia Jibianchun, it is characterized in that with the beta-cyclodextrin being sorbent material, at the mixed solution that contains methyl phenyl ketone and α-Jia Jibianchun, under mild conditions, utilize beta-cyclodextrin that the difference of methyl phenyl ketone and α-Jia Jibianchun adsorptive power is realized both separation.
2. method according to claim 1, it is characterized in that adopting following steps: under 20 ~ 40 ℃, normal pressure, beta-cyclodextrin is joined in the mixed solution that contains methyl phenyl ketone and α-Jia Jibianchun, beta-cyclodextrin carries out preferentially adsorbed to methyl phenyl ketone, desorption is carried out with desorbing agent in the absorption back, and the beta-cyclodextrin after the recovery is reused.
3. method according to claim 1 is characterized in that described mixed solution is to contain the aqueous solution of methyl phenyl ketone and α-Jia Jibianchun or contain methyl phenyl ketone and the water/ethanolic soln of α-Jia Jibianchun.
4. method according to claim 1 is characterized in that in the described mixed solution, and the total content of methyl phenyl ketone and α-Jia Jibianchun is 10 g/L ~ 40 g/L.
5. method according to claim 1 is characterized in that described desorbing agent is a kind of in ethyl acetate, methyl alcohol or the ethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101854461A CN103288617A (en) | 2013-05-20 | 2013-05-20 | Method for selectively adsorbing and separating acetophenone and alpha-methyl benzyl alcohol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101854461A CN103288617A (en) | 2013-05-20 | 2013-05-20 | Method for selectively adsorbing and separating acetophenone and alpha-methyl benzyl alcohol |
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| CN103288617A true CN103288617A (en) | 2013-09-11 |
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| CN2013101854461A Pending CN103288617A (en) | 2013-05-20 | 2013-05-20 | Method for selectively adsorbing and separating acetophenone and alpha-methyl benzyl alcohol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418397A (en) * | 2015-10-28 | 2016-03-23 | 衢州群颖化学科技有限公司 | Separation method for acetophenone and 1-phenylethanol |
| CN105418380A (en) * | 2015-12-21 | 2016-03-23 | 广西大学 | Acetophenone and 1-phenethyl alcohol separation method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1261395A (en) * | 1997-07-03 | 2000-07-26 | 埃克森化学专利公司 | Removal of benzene from organic streams using cyclodextrins |
| CN101891609A (en) * | 2010-07-07 | 2010-11-24 | 天津大学 | Inclusion separating method and application of isomerides of 3-diphenic acid and 4-diphenic acid |
| CN102627544A (en) * | 2012-03-26 | 2012-08-08 | 中山大学 | Method for separating acetophenone and alpha-methyl benzylalcohol |
-
2013
- 2013-05-20 CN CN2013101854461A patent/CN103288617A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1261395A (en) * | 1997-07-03 | 2000-07-26 | 埃克森化学专利公司 | Removal of benzene from organic streams using cyclodextrins |
| CN101891609A (en) * | 2010-07-07 | 2010-11-24 | 天津大学 | Inclusion separating method and application of isomerides of 3-diphenic acid and 4-diphenic acid |
| CN102627544A (en) * | 2012-03-26 | 2012-08-08 | 中山大学 | Method for separating acetophenone and alpha-methyl benzylalcohol |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418397A (en) * | 2015-10-28 | 2016-03-23 | 衢州群颖化学科技有限公司 | Separation method for acetophenone and 1-phenylethanol |
| CN106866395A (en) * | 2015-10-28 | 2017-06-20 | 江西科苑生物药业有限公司 | A kind of separation method of acetophenone and 1 benzyl carbinol |
| CN106866396A (en) * | 2015-10-28 | 2017-06-20 | 江西科苑生物药业有限公司 | A kind of separation method of acetophenone and 1 benzyl carbinol |
| CN106866395B (en) * | 2015-10-28 | 2020-09-22 | 江西科苑生物药业有限公司 | Method for separating acetophenone and 1-phenethyl alcohol |
| CN106866396B (en) * | 2015-10-28 | 2020-09-22 | 江西科苑生物药业有限公司 | Method for separating acetophenone and 1-phenethyl alcohol |
| CN105418380A (en) * | 2015-12-21 | 2016-03-23 | 广西大学 | Acetophenone and 1-phenethyl alcohol separation method |
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Application publication date: 20130911 |