CN1176892C - Phenylbenzyl ketone purifying method - Google Patents
Phenylbenzyl ketone purifying methodInfo
- Publication number
- CN1176892C CN1176892C CNB011390557A CN01139055A CN1176892C CN 1176892 C CN1176892 C CN 1176892C CN B011390557 A CNB011390557 A CN B011390557A CN 01139055 A CN01139055 A CN 01139055A CN 1176892 C CN1176892 C CN 1176892C
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- China
- Prior art keywords
- phenylbenzyl ketone
- purification process
- phenylbenzyl
- add
- gac
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Abstract
The present invention relates to a method for purifying phenylbenzyl ketone. A desoxybenzoin crude product is dissolved by methanol or alcohol or benzene. Active carbon is added for heating, return and decoloring. Active carbon is removed by filtration. Ligarine with the temperature of 60 DEG C to 120 DEG C or n-hexane or n-pentane is added in a filtered solution to make the phenylbenzyl ketone crystallized, cooled and separated. The phenylbenzyl ketone after purification is obtained. The method of the present invention has the advantages of simple operation, simple equipment, low preparation cost and high yield and is suitable for industrial preparation in a large scale. The obtained product has high purity and stable properties.
Description
Technical field
The present invention relates to a kind of purification process of phenylbenzyl ketone.
Background technology
Phenylbenzyl ketone (Deoxybenzoin), another name deoxybenzoin, phenylbenzyl ketone, benzyl phenyl ketone, molecular formula C
14H
12O, molecular weight 196.25.Phenylbenzyl ketone is a very important fine chemicals, can be used as medicine, essence and flavoring agent intermediate.
In the prior art, ORGANIC SYNTHESES (12,16,156-158) a kind of purification process of phenylbenzyl ketone is disclosed, be with 91～92g phenylbenzyl ketone crude product earlier under 160 ℃, 5mmHg underpressure distillation obtain 81～82g phenylbenzyl ketone, use recrystallizing methanol then, be further purified, obtain the pure product 67～70g of phenylbenzyl ketone at last.This method is at first wanted underpressure distillation, and is temperature required all higher with vacuum tightness from the suitability for industrialized production angle, inconvenient operation, and also need with the further crystallization of methyl alcohol, production process is complicated, influences product yield, and production cost is higher.
J.C.S. (1959,475-477) disclosed phenylbenzyl ketone purification process is with 95% ethanol the phenylbenzyl ketone crude product to be carried out recrystallization purifying, this method is all right for the effect of the higher crude product of phenylbenzyl ketone content, and for impure more crude product, color and purity by its phenylbenzyl ketone product of primary crystallization all are difficult to reach requirement, must just can obtain the higher phenylbenzyl ketone product of purity by recrystallization repeatedly, solvent load is very big, yield also reduces with the increase of recrystallization number of times, the also corresponding raising of purifying cost.
Tetrahedron Letter (1982,23 (30), 3085-3088) disclosed method is to be eluent with normal hexane-ether, and the phenylbenzyl ketone crude product is carried out purification by silica gel column chromatography.J.Org.Chem. (2000,65,6458-6461) disclosed method is to be eluent with normal hexane-ethyl acetate, and the phenylbenzyl ketone crude product is carried out silica gel column chromatography, carries out purifying with ethyl alcohol recrystallization again.Above-mentioned two kinds of methods adopt silica gel column chromatography, only are suitable for laboratory scale separation preparation, be difficult to realize in suitability for industrialized production, and solvent load are very big, and cost is very high.
Summary of the invention
At the deficiency of above-mentioned phenylbenzyl ketone purification process, the purpose of this invention is to provide a kind of purification process of phenylbenzyl ketone, this method is easy and simple to handle, and product cost is low, purity is high, and the phenylbenzyl ketone yield is also high, is suitable for suitability for industrialized production.
Method of the present invention is to realize like this.The purification process of phenylbenzyl ketone of the present invention comprises following operation steps: the phenylbenzyl ketone crude product is with methyl alcohol or ethanol or benzene dissolving, add the decolouring of gac reflux again, remove by filter gac, in filtrate, add temperature and be 60 ℃～120 ℃ sherwood oil or normal hexane or Skellysolve A and make the phenylbenzyl ketone crystallization, cooling, separate, obtain the phenylbenzyl ketone behind the purifying.
Phenylbenzyl ketone purification process of the present invention, the purity of described phenylbenzyl ketone crude product are 65～98% (weight).
Phenylbenzyl ketone purification process of the present invention adopts proper amount of solvent earlier with the phenylbenzyl ketone dissolving crude product, can suitably heat (40 ℃～60 ℃), is beneficial to the dissolving of phenylbenzyl ketone crude product.Described solvent is methyl alcohol, ethanol, benzene etc., and its add-on is the phenylbenzyl ketone crude product: methyl alcohol or ethanol or benzene=1: 2.5～5 (weight).
Phenylbenzyl ketone purification process of the present invention adopt to add gac and refluxes and adsorb coloring matter in the phenylbenzyl ketone crude product, removes by filter gac then, and the filtrate color after the decolouring is more shallow, is generally faint yellow.The temperature of described gac reflux is controlled at 40 ℃～60 ℃, and return time was controlled at 20～40 minutes.The add-on of gac is the phenylbenzyl ketone crude product: gac=1: 0.015～0.1 (weight), the fineness of gac are 200～400 orders.
Phenylbenzyl ketone purification process of the present invention, it removes by filter the filtrate of gac, to wherein adding the less solvent of polarity phenylbenzyl ketone is crystallized out.Adopting the less solvent of polarity mainly is the difference of utilizing phenylbenzyl ketone solubleness in the opposed polarity solvent, particularly less sherwood oil of polarity etc. can make the phenylbenzyl ketone that is dissolved in the ethanol equal solvent separate out fast, improve yield, and the phenylbenzyl ketone crystalline solid of separating out is white, purity height.The less solvent of described polarity is sherwood oil, normal hexane, Skellysolve A etc., and its add-on is sherwood oil or normal hexane or Skellysolve A: methyl alcohol or ethanol or benzene=1: 2.5～5 (weight).
Phenylbenzyl ketone purification process of the present invention compared with prior art has the following advantages: one, method of the present invention adopts activated carbon decolorizing, cheap, good decolorizing effect, by in filtrate, adding the less solvent of polarity, can make the phenylbenzyl ketone rapid crystallization, production unit is simple, and turndown ratio is big, cost is low, is fit to large-scale industrial production.Two, the product purity height that obtains of method of the present invention, product property is stable, and its purity can reach more than 99%, and fusing point is 54.5～56 ℃, and product yield height can reach more than 93%.
Embodiment
Further specify the present invention below by detailed description, but embodiment not a limitation of the present invention to specific embodiments of the invention.
Embodiment 1
Outward appearance is 65% phenylbenzyl ketone crude product 100g for red, purity, pour into and have in the churned mechanically there-necked flask, in there-necked flask, add the 250g dehydrated alcohol, a little the heating, temperature is controlled at 40 ℃, treat that the phenylbenzyl ketone crude product dissolves fully after, add 5g 350 purpose gacs, reflux 30 minutes, reflux temperature is 40 ℃, filtered while hot is removed gac, in filtrate, add the 100g sherwood oil again, temperature is controlled at about 60～65 ℃, places cooling, separates, get white phenylbenzyl ketone solid 52.0g, purity 〉=99%, 54.5～56 ℃ of fusing points, yield 80.0%.
Embodiment 2
Outward appearance is yellow, purity is 80% phenylbenzyl ketone crude product 1000g, pour into and have in the churned mechanically there-necked flask, in there-necked flask, add the 3000g dehydrated alcohol, a little the heating, temperature is controlled at 60 ℃, treat that the phenylbenzyl ketone crude product dissolves fully after, add 30g 250 purpose gacs, reflux 25 minutes, reflux temperature is 60 ℃, filtered while hot is removed gac, in filtrate, add the 1000g sherwood oil again, temperature is controlled at about 110～120 ℃, places cooling, separates, get white phenylbenzyl ketone solid 680g, purity 〉=99%, 54.5～56 ℃ of fusing points, yield 85.0%.
Embodiment 3
Outward appearance is 95% phenylbenzyl ketone crude product 1000g for yellow, purity, pour into and have in the churned mechanically reactor, in reactor, add the 3000g dehydrated alcohol, a little the heating, temperature is controlled at 50 ℃, treat that the phenylbenzyl ketone crude product dissolves fully after, add 20g 200 purpose gacs, reflux 20 minutes, reflux temperature is 60 ℃, filtered while hot is removed gac, in filtrate, add the 1000g sherwood oil again, temperature is controlled at about 90～100 ℃, places cooling, separates, get white phenylbenzyl ketone solid 874g, purity 〉=99%, 54.5～56 ℃ of fusing points, yield 92.0%.
Embodiment 4
Outward appearance is 95% phenylbenzyl ketone crude product 4kg for yellow, purity, pour into and have in the churned mechanically reactor, in reactor, add 16kg methyl alcohol, a little the heating, temperature is controlled at 50 ℃, treat that the phenylbenzyl ketone crude product dissolves fully after, add 400g 200 purpose gacs, reflux 20 minutes, reflux temperature is 60 ℃, filtered while hot is removed gac, in filtrate, add the 16kg normal hexane again, temperature is controlled at about 90～120 ℃, places cooling, separates, get white phenylbenzyl ketone solid 3.48kg, purity 〉=99%, 54.5～56 ℃ of fusing points, yield 91.6%.
Embodiment 5
Outward appearance is 98% phenylbenzyl ketone crude product 100g for yellow, purity, pour into and have in the churned mechanically there-necked flask, in there-necked flask, add the 250g solvent benzol, a little the heating, temperature is controlled at 50 ℃, treat that the phenylbenzyl ketone crude product dissolves fully after, add 5g 400 purpose gacs, reflux 40 minutes, reflux temperature is 60 ℃, filtered while hot is removed gac, in filtrate, add the 500g Skellysolve A again, temperature is controlled at about 60～90 ℃, places cooling, separates, get white phenylbenzyl ketone solid 91.2g, purity 〉=99%, 54.5～56 ℃ of fusing points, yield 93.1%.
Claims (8)
1, a kind of purification process of phenylbenzyl ketone, it is characterized in that this method comprises following operation steps: the phenylbenzyl ketone crude product is with methyl alcohol or ethanol or benzene dissolving, add the decolouring of gac reflux again, remove by filter gac, in filtrate, add temperature and be 60 ℃～120 ℃ sherwood oil or normal hexane or Skellysolve A and make the phenylbenzyl ketone crystallization, cooling separates, and obtains the phenylbenzyl ketone behind the purifying.
2, purification process as claimed in claim 1, the purity that it is characterized in that the phenylbenzyl ketone crude product are 65～98% (weight).
3, purification process as claimed in claim 1, the add-on that it is characterized in that described methyl alcohol or ethanol or benzene are the phenylbenzyl ketone crude products: methyl alcohol or ethanol or benzene=1: 2.5～4 (weight).
4, purification process as claimed in claim 1, the add-on that it is characterized in that described gac are the phenylbenzyl ketone crude products: gac=1: 0.015～0.1 (weight).
5, as claim 1 or 4 described purification process, the fineness that it is characterized in that described gac is 200～400 orders.
6, purification process as claimed in claim 1 is characterized in that the temperature of described gac reflux is controlled at 40 ℃～60 ℃.
7, purification process as claimed in claim 1, the time that it is characterized in that described gac reflux is 20～40 minutes.
8, purification process as claimed in claim 1, the add-on that it is characterized in that described sherwood oil or normal hexane or Skellysolve A are sherwood oil or normal hexane or Skellysolve A: methyl alcohol or ethanol or benzene=1: 2.5～5 (weight).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011390557A CN1176892C (en) | 2001-12-05 | 2001-12-05 | Phenylbenzyl ketone purifying method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011390557A CN1176892C (en) | 2001-12-05 | 2001-12-05 | Phenylbenzyl ketone purifying method |
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| CN1422838A CN1422838A (en) | 2003-06-11 |
| CN1176892C true CN1176892C (en) | 2004-11-24 |
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| CNB011390557A Expired - Fee Related CN1176892C (en) | 2001-12-05 | 2001-12-05 | Phenylbenzyl ketone purifying method |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435464A (en) * | 2013-09-03 | 2013-12-11 | 山东诚创医药技术开发有限公司 | Preparation method of diphenylethanone |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107954845B (en) * | 2016-10-14 | 2022-08-19 | 西姆莱斯有限公司 | Process for purifying 4-hydroxyacetophenone |
-
2001
- 2001-12-05 CN CNB011390557A patent/CN1176892C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435464A (en) * | 2013-09-03 | 2013-12-11 | 山东诚创医药技术开发有限公司 | Preparation method of diphenylethanone |
| CN103435464B (en) * | 2013-09-03 | 2014-11-26 | 山东诚创医药技术开发有限公司 | Preparation method of diphenylethanone |
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| Publication number | Publication date |
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| CN1422838A (en) | 2003-06-11 |
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