CN101234970B - Method for purifying multiphenyl ethylene alkyl phenol ethyoxyl methacrylic acid ester - Google Patents
Method for purifying multiphenyl ethylene alkyl phenol ethyoxyl methacrylic acid ester Download PDFInfo
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- CN101234970B CN101234970B CN2008100142613A CN200810014261A CN101234970B CN 101234970 B CN101234970 B CN 101234970B CN 2008100142613 A CN2008100142613 A CN 2008100142613A CN 200810014261 A CN200810014261 A CN 200810014261A CN 101234970 B CN101234970 B CN 101234970B
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- methyl acrylic
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- ethoxy ester
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Abstract
The invention relates to a method for purifying methacrylic acid styrene alkylphenol ethoxylated ester (SEM-25) via column chromatography, comprising removing water of the product containing SEM-25 via azeotropic distillation to obtain a mixture I, separating SEM-25 and methacrylic acid in the mixture I via column chromatography, collecting the effluent liquid only containing SEM-25, depressurizing and distilling solvent to obtain pure SEM-25 product. The method can prepare SEM-25 pure product via simple operation as removing water, separating via column chromatography and depressurizing and distilling solvent, while the product purity is higher than 97.0% and yield reaches 90%, and the solvents in all steps can be recovered.
Description
Technical field
The extracting method of methyl acrylic multi-styrene alkylphenol ethoxy ester of the present invention relates in particular to the method for purifying multiphenyl ethylene alkyl phenol ethyoxyl methacrylic acid ester.
Background technology
Methyl acrylic multi-styrene alkylphenol ethoxy ester can abbreviate SEM-25 as, its structural formula as shown in Equation 1, wherein n is 25.This compound contains two keys, a polyoxyethylene long-chain and a non-ionic group that contains a plurality of phenyl ring.Its trade(brand)name SIPOMER SEM-25 is that French Rhodia produces at present, is the mixture of SEM-25 and water and methacrylic acid, the about 18-22% of water content wherein, the about 18-22% of methacrylic acid content.
The signal formula of formula 1:SEM-25 structural formula and different chemical environment H thereof
SEM-25 can be used as function monomer and is used for letex polymerization, especially is more common in and uses it for preparation caustic solubility associative thickener, and SEM-25 can also be used for the fields such as preparation of other functional latex preparation, polymers functionization, poly (standard) rotaxane.Because the existence of acrylate makes the application of SEM-25 in research and production be subjected to considerable restraint.Therefore preparing the pure product of SEM-25 possesses important meaning.But do not see the method report of purification SEM-25 from SIPOMER SEM-25 both at home and abroad, find no the pure product of SEM-25 yet and sell.
Summary of the invention
In order to remedy the deficiencies in the prior art, the invention provides the method for purification of a kind of methyl acrylic multi-styrene alkylphenol ethoxy ester (SEM-25).
Technical scheme of the present invention is as follows:
The method of a kind of purifying methyl acrylic multi-styrene alkylphenol ethoxy ester (SEM-25) is characterized in that step is as follows:
1. remove moisture in the methyl acrylic multi-styrene alkylphenol ethoxy ester with azeotropic distn, mixture I,
2. with SEM-25 and methacrylic acid among the column chromatography separating mixture I, collect the effluent liquid of only being made up of SEM-25, decompression steams solvent, gets the pure product of SEM-25.
Azeotropic water removing in the above-mentioned steps 1, preferred azeotropic solvent is methylene dichloride or dehydrated alcohol, utilizes azeotropic solvent to remove moisture under lower temperature with the principle that water forms azeotrope.
Preferred when azeotropic solvent is methylene dichloride, the dosage of methylene dichloride is: the mass ratio of water-content and methylene dichloride (0.05-0.20) among the mixture I: 1.
Preferably, when azeotropic solvent was dehydrated alcohol, the dosage of dehydrated alcohol was: the mass ratio of water-content and dehydrated alcohol (0.03-0.045) among the mixture I: 1.
Preferably, the column chromatography of above-mentioned steps 2 separates, and mixture I is added in the chloroform to stir earlier, joins the chromatographic column upper end with dropper, opens chromatographic column lower end valve, treats its liquid level to quartz sand face lower edge, and valve-off adds eluent and carries out drip washing.Collect effluent liquid, and with thin layer chromatography test composition wherein, treat in the effluent liquid SEM-25 component only to be arranged and when not having methacrylic acid, all effluent liquid after collecting steam solvent and obtain product.
The column chromatography for separation of above-mentioned steps 2, preferred eluent is chloroform and methyl alcohol mixed liquor, its preferred proportioning is a chloroform: methyl alcohol=(8-12): 1 (volume ratio).
The raw material explanation
The raw material that the method for purification of SEM-25 of the present invention is used is trade(brand)name SIPOMER SEM-25, and French Rhodia produces and sells.Wherein, the about 18-22%wt of water content, the about 18-22%wt of methacrylic acid content.
The excellent results of the inventive method is as follows:
The 1 method of purification processing ease that the present invention relates to.Only by dewater, column chromatography for separation and decompression steam conventional steps such as solvent and can obtain the pure product of SEM-25.
The 2 method of purification good separating effects that the present invention relates to.Adopt separation method of the present invention, productive rate is up to 90%, and product purity is higher than 97.0%.
The 3 method of purification economical effectivenesss that the present invention relates to are obvious, and the solvent that adopts in each step is all recyclable to be utilized again.
Embodiment
The present invention will be further described below in conjunction with embodiment, but be not limited thereto.
Used medicine is as follows among the embodiment:
Raw material SIPOMER SEM-25, French Rhodia produces, wherein, the about 18-22%wt of water content, the about 18-22%wt of methacrylic acid content.Chloroform (trichloromethane), dehydrated alcohol, ethylene dichloride, methyl alcohol, column chromatography is commercially available with silica gel.
Embodiment 1:SEM-25 method of purification, step is as follows:
1. remove moisture among the SIPOMER SEM-25 with azeotropic distn
Take by weighing 30g SIPOMER SEM-25, wherein moisture about 5.4g-6.6g can add ethylene dichloride 34g, after wherein moisture is all steamed, obtains the mixture of SEM-25 and methacrylic acid.
2. separate SEM-25 and methacrylic acid with column chromatography
1) will add chloroform in the proper silica gel, stir the back and pack in the post, when treating that the silica gel face no longer descends, quartz sand evenly is sprinkled into chromatographic column, thick about 1cm with funnel.
2) will need to stir in the adding chloroform in the isolating sample, join the chromatographic column upper end with dropper, open chromatographic column lower end valve, treat that its liquid level is to quartz sand face lower edge, valve-off adds previously prepared chloroform and carbinol mixture eluent (chloroform/methanol=8/1) and carries out drip washing.
3) collect effluent liquid with the fine taper bottle, and with thin layer chromatography test composition wherein.Treat only to form in the effluent liquid and when not having methacrylic acid all effluent liquid after collecting by SEM-25.Steam solvent and can obtain the pure product of SEM-25.Purity is higher than 97.2%, yield 90%.
Products therefrom characterizes
Above gained SEM-25 has been done
1The HNMR test.The H of different chemical environment is shown in formula 1 as described in the background art among the SEM-25, its nucleus magnetic resonance displacement and belong to as follows: and 1H NMR (δ ppm, D2O): 6.5-7.2 (m, 17H, H-5, H-7); 6.0-6.2. (s, H, H-1a); 5.75-5.3. (s, H, H-1b); 4.1-4.75 (m, 3H, H-6); 3.9-3.3 (m, 100H, H-3); 1.75-1.9 (m, 3H, H-2); 1.05-1.4 (m, 12H, H-4).The number of each H is identical substantially in peak area and the molecular formula, the inclusion-free peak.Prove that this product is the pure product of SEM-25.
Embodiment 2:
As described in embodiment 1, different is:
1. step 1 is used dehydrated alcohol 150g, after the moisture in the raw material is all steamed, obtains the mixture of SEM-25 and methacrylic acid.Products therefrom mixture I.
2. mixture I is added in the chloroform and stir, join the chromatographic column upper end with dropper, open chromatographic column lower end valve, treat that its liquid level is to quartz sand face lower edge, valve-off adds previously prepared chloroform and carbinol mixture eluent (volume ratio chloroform/methanol=12/1) and carries out drip washing.
The pure product of gained SEM-25, purity is higher than 97.5%, yield 90%.
Claims (6)
1. the method for a purifying methyl acrylic multi-styrene alkylphenol ethoxy ester is characterized in that, step is as follows:
(1) remove moisture in the methyl acrylic multi-styrene alkylphenol ethoxy ester with azeotropic distn, mixture I;
Used azeotropic solvent is methylene dichloride or dehydrated alcohol;
(2) with methyl acrylic multi-styrene alkylphenol ethoxy ester and methacrylic acid among the column chromatography separating mixture I, collect the effluent liquid that methyl acrylic multi-styrene alkylphenol ethoxy ester is only arranged, decompression steams solvent, gets the pure product of methyl acrylic multi-styrene alkylphenol ethoxy ester.
2. according to the method for the described purifying methyl acrylic multi-styrene alkylphenol ethoxy ester of claim 1, it is characterized in that, when azeotropic solvent was methylene dichloride, the dosage of methylene dichloride was: the mass ratio of water-content and methylene dichloride (0.05-0.20) among the mixture I: 1.
3. according to the method for the described purifying methyl acrylic multi-styrene alkylphenol ethoxy ester of claim 1, it is characterized in that, when azeotropic solvent was dehydrated alcohol, the dosage of dehydrated alcohol was: the mass ratio of water-content and dehydrated alcohol (0.03-0.045) among the mixture I: 1.
4. according to the method for the described purifying methyl acrylic multi-styrene alkylphenol ethoxy ester of claim 1, it is characterized in that, the column chromatography of step (2) separates, earlier mixture I is added in the chloroform and stir, join the chromatographic column upper end with dropper, open chromatographic column lower end valve, treat that its liquid level is to quartz sand face lower edge, valve-off adds eluent and carries out drip washing; Collect effluent liquid, and with thin layer chromatography test composition wherein, treat only methyl acrylic multi-styrene alkylphenol ethoxy ester to be arranged in the effluent liquid and when not having methacrylic acid, all effluent liquid after collecting steam solvent and obtain product.
5. according to the method for the described purifying methyl acrylic multi-styrene alkylphenol ethoxy ester of claim 4, it is characterized in that used eluent is chloroform and methyl alcohol mixed liquor.
6. according to the method for the described purifying methyl acrylic multi-styrene alkylphenol ethoxy ester of claim 5, it is characterized in that used eluent volume ratio proportioning is a chloroform: methyl alcohol=(8-12): 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100142613A CN101234970B (en) | 2008-02-18 | 2008-02-18 | Method for purifying multiphenyl ethylene alkyl phenol ethyoxyl methacrylic acid ester |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100142613A CN101234970B (en) | 2008-02-18 | 2008-02-18 | Method for purifying multiphenyl ethylene alkyl phenol ethyoxyl methacrylic acid ester |
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| CN101234970A CN101234970A (en) | 2008-08-06 |
| CN101234970B true CN101234970B (en) | 2010-04-07 |
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| CN2008100142613A Expired - Fee Related CN101234970B (en) | 2008-02-18 | 2008-02-18 | Method for purifying multiphenyl ethylene alkyl phenol ethyoxyl methacrylic acid ester |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0390577A2 (en) * | 1989-03-31 | 1990-10-03 | MITSUI TOATSU CHEMICALS, Inc. | Purification and preparation processes for methyl methacrylate |
| CN1241892C (en) * | 2003-12-09 | 2006-02-15 | 上海华谊丙烯酸有限公司 | Method for purifying acrylic acid |
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2008
- 2008-02-18 CN CN2008100142613A patent/CN101234970B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0390577A2 (en) * | 1989-03-31 | 1990-10-03 | MITSUI TOATSU CHEMICALS, Inc. | Purification and preparation processes for methyl methacrylate |
| CN1241892C (en) * | 2003-12-09 | 2006-02-15 | 上海华谊丙烯酸有限公司 | Method for purifying acrylic acid |
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| CN101234970A (en) | 2008-08-06 |
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