CN104926697A - Combined production method - Google Patents
Combined production method Download PDFInfo
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- CN104926697A CN104926697A CN201510297545.8A CN201510297545A CN104926697A CN 104926697 A CN104926697 A CN 104926697A CN 201510297545 A CN201510297545 A CN 201510297545A CN 104926697 A CN104926697 A CN 104926697A
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Abstract
The invention provides a combined production method which comprises the following steps: according to a weight ratio of acrylonitrile to concentrated sulfuric acid being 5:(1-2), sufficiently mixing acrylonitrile and concentrated sulfuric acid to obtain a mixture A; according to a weight ratio of the mixture A to isobutene being 13:(1-3), sufficiently mixing the mixture A and isobutene to obtain a mixture B, wherein a solid in the mixture B is precipitated; conducting solid-liquid separation on the mixture B to obtain a solid C and a filtration liquid D; drying the solid C to obtain a product E, namely 2-acrylamide-2-methylpropane sulfonic acid; distilling the filtration liquid D to obtain an acrylonitrile solution and a concentrated solution F through recovery; adding water of which the weight is the same as the concentrated solution F into the concentrated solution F to ensure that a solid is precipitated from the concentrated solution F, and then carrying out filtration to obtain a solid product G, namely N-tert-butyl acrylamide. The combined production method has the advantages that residues from the production of 2-acrylamide-2-methyl-1-propanesulfonic acid are utilized, so that resource conservation is realized, and the production cost is reduced.
Description
Technical field
The present invention relates to chemical technology field, be specifically related to a kind of co-production.
Background technology
At present, the production of 2-acrylamide-2-methylpro panesulfonic acid generally adopts and directly mixes obtained by vinyl cyanide, sulfuric acid, iso-butylene.The parameter of this production method process is all arranged for unique Product 2-acrylamide-2-methylpro panesulfonic acid usually.It is residual that the material that the some by products produced in production process remain after filtrate is distilled recovery enters still, and find after testing, the material during still is residual can produce N tert butyl acrylamide after treatment.In traditional production, N tert butyl acrylamide generally adopts vinyl cyanide to mix with iso-butylene to be hydrolyzed after acid catalysis and obtains.2-acrylamide-2-methylpro panesulfonic acid and N tert butyl acrylamide are diverse materials, and its industrial production is method and apparatus alone.Although N tert butyl acrylamide can obtain as a small amount of impurity producing 2-acrylamide-2-methylpro panesulfonic acid, yet there are no these two kinds of materials all simultaneously as production object and at the co-production of synthesis phase set comprehensive optimum condition and parameter index.
Summary of the invention
In order to solve the problem, the invention provides a kind of co-production, comprising:
Vinyl cyanide is fully mixed with weight ratio 5:1-2 with the vitriol oil, obtains mixture A;
Mixture A is fully mixed with weight ratio 13:1-3 with iso-butylene, obtains the mixture B that solid is separated out;
Mixture B is carried out solid-liquid separation, obtains solid C and filtrate D;
Obtain product E by after solid C drying, product E is 2-acrylamide-2-methylpro panesulfonic acid;
Filtrate D is distilled, reclaims and obtain acrylonitrile solution and concentrated solution F;
Concentrated solution F is put into one pressure filter, add and mix with the water of concentrated solution F equal in quality, to there being solid to separate out, then filter and obtain solid product G, solid product G is product N tert butyl acrylamide after drying.
Preferably, the mixing temperature of described vinyl cyanide and the vitriol oil is-5 DEG C-20 DEG C.
Preferably, the mixing temperature of described vinyl cyanide and the vitriol oil is 10 DEG C-15 DEG C.
Preferably, the mixing temperature of described mixture A and iso-butylene is 10 DEG C-45 DEG C.
Preferably, the mixing temperature of described mixture A and iso-butylene is 30 DEG C-40 DEG C.
Preferably, the mixing temperature of described mixture A and iso-butylene is 35 DEG C.
Preferably, described filtrate D adopts the condition of negative pressure 78 DEG C to distill.
The beneficial effect of the preferred embodiment of the present invention is: 1, the leftover waste material of producing AMPS can use by co-production of the present invention, has saved resource, has reduced production cost; 2, the condition of the present invention to co-production is optimized, and adopts best working condition, make the output of 2-acrylamide-2-methylpro panesulfonic acid and the N tert butyl acrylamide obtained and purity all very high, the needs of production application can be met.
Accompanying drawing explanation
Fig. 1 is the schema of co-production of the present invention;
Fig. 2 is the high-efficient liquid phase chromatogram of 2-acrylamide-2-methylpro panesulfonic acid standard substance;
Fig. 3 is the high-efficient liquid phase chromatogram of the 2-acrylamide-2-methylpro panesulfonic acid that co-production of the present invention obtains;
Fig. 4 is the high-efficient liquid phase chromatogram of N tert butyl acrylamide standard substance;
Fig. 5 is the high-efficient liquid phase chromatogram that co-production of the present invention obtains the N tert butyl acrylamide also after refining.
Embodiment
Below in conjunction with accompanying drawing, technical scheme of the present invention is further described.
As shown in Figure 1, co-production of the present invention, comprises the following steps:
(1) vinyl cyanide is fully mixed with weight ratio 5:1-2 with the vitriol oil, obtain mixture A, if in the blending ratio of vinyl cyanide and the vitriol oil, increase the ratio of the vitriol oil, in final products therefrom, the ratio of 2-acrylamide-2-methylpro panesulfonic acid raises, if reduce the ratio of the vitriol oil, in final product, the ratio of product E raises; The mixing temperature of vinyl cyanide and the vitriol oil is-5 DEG C-20 DEG C, and preferred mixing temperature is 10 DEG C-15 DEG C.
(2) mixture A is fully mixed with weight ratio 13:1-3 with iso-butylene, obtain the mixture B that solid is separated out; The mixing temperature of mixture A and iso-butylene is 10 DEG C-45 DEG C, and preferred mixing temperature is 30 DEG C-40 DEG C, and best preferred mixing temperature is 35 DEG C.With best mixing temperature 35 DEG C for stagnation point, the mixing temperature of mixture A and iso-butylene raises, and in mixture B, solid is separated out more, and namely in final product, the output of product E is more; The mixing temperature of mixture A and iso-butylene reduces, and in mixture B, solid is separated out less, and namely in final product, the output of product G is more, adopts the mixing temperature of 35 DEG C, the ratio of final product E and product G can be made suitable.
(3) mixture B is carried out solid-liquid separation, obtain solid C and filtrate D; Product E is obtained by after solid C drying; Adopt the condition of negative pressure 78 DEG C to distill filtrate D, reclaim and obtain acrylonitrile solution and concentrated solution F, reclaim the recycle that the acrylonitrile solution obtained is reused for step (1).
(4) in concentrated solution F, add the water with concentrated solution F identical weight, after adding water, in concentrated solution F, have solid to separate out, then filter and obtain solid product G wet feed, after drying, be product G.
The obtained product of the co-production of embodiment of the present invention optimum condition is adopted to adopt high performance liquid chromatography to analyze, the high-efficient liquid phase chromatogram condition that product E and 2-acrylamide-2-methylpro panesulfonic acid standard substance adopt, identical with the high-efficient liquid phase chromatogram condition that N tert butyl acrylamide standard substance adopt with product G, namely the chromatographic condition of these two kinds of substance-measurings is all: C18 reverse-phase chromatographic column, moving phase is chromatogram methyl alcohol: ultrapure water=40:60, flow velocity 0.7mL/min, UV-detector, absorbing wavelength 210nm.
As shown in Figure 2-5, Fig. 2 is the high-efficient liquid phase chromatogram of 2-acrylamide-2-methylpro panesulfonic acid standard substance, Fig. 3 is the high-efficient liquid phase chromatogram of the product E that embodiment of the present invention co-production obtains, Fig. 2 and Fig. 3 contrast can be found out, the product E that embodiment of the present invention co-production obtains is identical with the peak shape of 2-acrylamide-2-methylpro panesulfonic acid standard substance, appearance time is consistent, and (appearance time of 2-acrylamide-2-methylpro panesulfonic acid standard substance is 2.633min, the appearance time of the product E that embodiment of the present invention co-production obtains is 2.688min), the purity of product E chromatographic peak is very high, therefore can judge that product E is 2-acrylamide-2-methylpro panesulfonic acid.Fig. 4 is the high-efficient liquid phase chromatogram of N tert butyl acrylamide standard substance, Fig. 5 is the high-efficient liquid phase chromatogram of the product G that embodiment of the present invention co-production obtains, Fig. 4 and Fig. 5 contrast can be found out, the product G that embodiment of the present invention co-production obtains is identical with the peak shape of N tert butyl acrylamide standard substance, appearance time is consistent, and (appearance time of N tert butyl acrylamide standard substance is 11.305min, the appearance time of the product G that embodiment of the present invention co-production obtains is 11.270min), the purity of product G chromatographic peak is very high, therefore can judge that product G is N tert butyl acrylamide.
From above-mentioned analysis, the co-production of the embodiment of the present invention is adopted to can be good at preparation 2-acrylamide-2-methylpro panesulfonic acid and N tert butyl acrylamide, and two kinds of obtained product purity are very high, the purity of more than 98% can be reached after refining, the needs of production application can be reached.
Set forth a lot of detail in the above description so that fully understand the present invention.But above description is only preferred embodiment of the present invention, the present invention can be much different from alternate manner described here to implement, and therefore the present invention is not by the disclosed concrete restriction implemented above.Any those skilled in the art are not departing under technical solution of the present invention ambit simultaneously, the Method and Technology content of above-mentioned announcement all can be utilized to make many possible variations and modification to technical solution of the present invention, or be revised as the Equivalent embodiments of equivalent variations.Every content not departing from technical solution of the present invention, according to technical spirit of the present invention to any simple modification made for any of the above embodiments, equivalent variations and modification, all still belongs in the scope of technical solution of the present invention protection.
Claims (7)
1. a co-production, is characterized in that, comprises the following steps:
Vinyl cyanide is fully mixed with weight ratio 5:1-2 with the vitriol oil, obtains mixture A;
Mixture A is fully mixed with weight ratio 13:1-3 with iso-butylene, obtains the mixture B that solid is separated out;
Mixture B is carried out solid-liquid separation, obtains solid C and filtrate D;
Obtain product E by after solid C drying, product E is 2-acrylamide-2-methylpro panesulfonic acid;
Filtrate D is distilled, reclaims and obtain acrylonitrile solution and concentrated solution F;
Concentrated solution F is put into one pressure filter, add and mix with the water of concentrated solution F equal in quality, to there being solid to separate out, then filter and obtain solid product G, solid product G is product N tert butyl acrylamide after drying.
2. co-production according to claim 1, is characterized in that, the mixing temperature of described vinyl cyanide and the vitriol oil is-5 DEG C-20 DEG C.
3. co-production according to claim 2, is characterized in that, the mixing temperature of described vinyl cyanide and the vitriol oil is 10 DEG C-15 DEG C.
4. co-production according to claim 1, is characterized in that, the mixing temperature of described mixture A and iso-butylene is 10 DEG C-45 DEG C.
5. co-production according to claim 4, is characterized in that, the mixing temperature of described mixture A and iso-butylene is 30 DEG C-40 DEG C.
6. co-production according to claim 1, is characterized in that, the mixing temperature of described mixture A and iso-butylene is 35 DEG C.
7. co-production according to claim 1, is characterized in that, described filtrate D adopts the condition of negative pressure 78 DEG C to distill.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510297545.8A CN104926697A (en) | 2015-06-01 | 2015-06-01 | Combined production method |
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| CN201510297545.8A CN104926697A (en) | 2015-06-01 | 2015-06-01 | Combined production method |
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| CN104926697A true CN104926697A (en) | 2015-09-23 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112047855A (en) * | 2020-09-19 | 2020-12-08 | 寿光市荣晟新材料有限公司 | N-tert-butyl acrylamide extraction method |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005029476A (en) * | 2003-07-08 | 2005-02-03 | Toagosei Co Ltd | METHOD FOR PRODUCING tert-BUTYLACRYLAMIDE |
| JP2010229250A (en) * | 2009-03-26 | 2010-10-14 | Toagosei Co Ltd | Method for producing 2-acrylamido-2-methylpropanesulfonic acid |
| CN101874017A (en) * | 2007-12-06 | 2010-10-27 | 东亚合成株式会社 | 2-acrylamide-2-methylpropanesulfonic acid and process for producing the same |
| JP2012025672A (en) * | 2010-07-20 | 2012-02-09 | Toagosei Co Ltd | METHOD FOR PRODUCING HIGH-PURITY N-tert-BUTYLACRYLAMIDE AND SUBLIMATION PURIFICATION APPARATUS |
-
2015
- 2015-06-01 CN CN201510297545.8A patent/CN104926697A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005029476A (en) * | 2003-07-08 | 2005-02-03 | Toagosei Co Ltd | METHOD FOR PRODUCING tert-BUTYLACRYLAMIDE |
| CN101874017A (en) * | 2007-12-06 | 2010-10-27 | 东亚合成株式会社 | 2-acrylamide-2-methylpropanesulfonic acid and process for producing the same |
| JP2010229250A (en) * | 2009-03-26 | 2010-10-14 | Toagosei Co Ltd | Method for producing 2-acrylamido-2-methylpropanesulfonic acid |
| JP2012025672A (en) * | 2010-07-20 | 2012-02-09 | Toagosei Co Ltd | METHOD FOR PRODUCING HIGH-PURITY N-tert-BUTYLACRYLAMIDE AND SUBLIMATION PURIFICATION APPARATUS |
Non-Patent Citations (1)
| Title |
|---|
| DRAGAN DEMETRA: "On the Ritter synthesis of N-tert-butyl acrylamide. 1. Reaction between isobutylene and acrylonitrile in nonaqueous medium", 《REVUE ROUMAINE DE CHIMIE》, vol. 38, no. 9, 31 December 1993 (1993-12-31), pages 1073 - 1082 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112047855A (en) * | 2020-09-19 | 2020-12-08 | 寿光市荣晟新材料有限公司 | N-tert-butyl acrylamide extraction method |
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