CN105693562A - Purification method of 2-acrylamide-2-methyl propane sulfonic acid crude product - Google Patents
Purification method of 2-acrylamide-2-methyl propane sulfonic acid crude product Download PDFInfo
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- CN105693562A CN105693562A CN201511019031.2A CN201511019031A CN105693562A CN 105693562 A CN105693562 A CN 105693562A CN 201511019031 A CN201511019031 A CN 201511019031A CN 105693562 A CN105693562 A CN 105693562A
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- acrylamide
- crude product
- methylpro panesulfonic
- acid crude
- purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a purification method of a 2-acrylamide-2-methyl propane sulfonic acid crude product. The method comprises the steps that the 2-acrylamide-2-methyl propane sulfonic acid crude product is washed through acrylonitrile, and a washing product is obtained; the washing product is mixed with low carbon alcohol, and a mixture is obtained; the mixture is cooled and kept warm, then solid-liquid separation is conducted, and solid matter is obtained; the solid matter is dried, and a 2-acrylamide-2-methyl propane sulfonic acid pure product is obtained. According to the purification method of the 2-acrylamide-2-methyl propane sulfonic acid crude product, acrylonitrile and low carbon alcohol serve as complex solvents to conduct purification treatment on the 2-acrylamide-2-methyl propane sulfonic acid crude product, the treatment method is simple, water is not needed to serve as a solvent, and the purity and yield of the purified product are high. It is indicated through experiments that the yield of the 2-acrylamide-2-methyl propane sulfonic acid pure product prepared through the purification method ranges from 80% to 85%, and the purity is larger than 99%.
Description
Technical field
The present invention relates to 2-acrylamide-2-methylpro panesulfonic acid technical field, particularly relate to the process for purification of a kind of 2-acrylamide-2-methylpro panesulfonic acid crude product。
Background technology
2-acrylamide-2-methylpro panesulfonic acid (AMPS) is a kind of widely used multifunctional polymeric monomer, its outward appearance is white crystal or powder, there is strong hygroscopicity, slightly tart flavour, soluble in water, dimethylformamide, being slightly soluble in methanol, ethanol, be insoluble in the organic solvent such as acetone, benzene, aqueous solution is in acidity。AMPS molecule makes it have good salt tolerance, heat-resisting quantity, electric conductivity, dyeing affinity containing strong anionic property and hydrophilic functional group's sulfonic group；Simultaneously active in molecule carbon-carbon double bond so that it is copolymerization can be carried out with many vinyl monomers。The homopolymer of AMPS and copolymer can be widely applied to the fields such as petroleum industry, chemical fibre, printing and dyeing, coating, surfactant, antistatic, water process, pottery, photograph, washing assisant, ion exchange resin。
At present, the synthetic method than major AMPS is to react comparatively gentle when with acrylonitrile, oleum and isobutene. for raw material both at home and abroad, prepares AMPS。When generally synthesizing, acrylonitrile and isobutene. are unsaturated monomer molecule, side reaction can be occurred in acid condition to generate N-tert-butyl acrylamide or methallylsulfonic acid etc., the meeting synthetically produced adverse influence to AMPS, it is typically in building-up process and can add the additives such as acid, anhydride or amides compound, or make acrylonitrile carry out effective mode such as mix with sulphuric acid by pipe-line mixer to be controlled, but the purity of product crude product being prepared obtaining is not high, therefore after synthesis AMPS, it is typically conducted purification。The purification process of AMPS mainly has recrystallization method and solvent wash method, and recrystallization method purge process is complicated, is unfavorable for the application in commercial production；Prior art is generally adopted acrylonitrile-water and as solvent, AMPS is washed, and in washing process, AMPS is susceptible to autohemagglutination and decomposition under the effect of water, makes the purity after AMPS purifying crude and yield poor。
Summary of the invention
In view of this, it is an object of the invention to provide the process for purification of a kind of 2-acrylamide-2-methylpro panesulfonic acid crude product, the yield of the 2-acrylamide-2-methylpro panesulfonic acid sterling that process for purification provided by the invention prepares is higher, purity is better。
The invention provides the process for purification of a kind of 2-acrylamide-2-methylpro panesulfonic acid crude product, including:
Adopt acrylonitrile washing 2-acrylamide-2-methylpro panesulfonic acid crude product, obtain washed product；
Described washed product is mixed with low-carbon alcohols, obtains mixture；
After being lowered the temperature by described mixture, insulation, then carries out solid-liquid separation, obtains solid matter；
Described solid matter is dried, obtains 2-acrylamide-2-methylpro panesulfonic acid sterling。
Preferably, the carbon number in described low-carbon alcohols is 1～4。
Preferably, described low-carbon alcohols is methanol, ethanol, ethylene glycol, normal propyl alcohol or isopropanol。
Preferably, the consumption of described low-carbon alcohols is the low-carbon alcohols that every gram of washed product adopts 1mL～5mL。
Preferably, the water content in described acrylonitrile is 1wt%～5wt%。
Preferably, the purity of described 2-acrylamide-2-methylpro panesulfonic acid crude product is 90%～95%。
Preferably, described mixing temperature is 40 DEG C～50 DEG C, and the time of described mixing is 1～3h。
Preferably, the temperature of described cooling is 20 DEG C～35 DEG C。
Preferably, the time of described insulation is 5～10 hours。
Preferably, described dry temperature is 50 DEG C～70 DEG C。
The present invention adopts acrylonitrile and low-carbon alcohols, as double solvents, the crude product of 2-acrylamide-2-methylpro panesulfonic acid is purified process, and processing method is simple, and need not adopt water as solvent, makes the product purity after purification and yield higher。Test result indicate that, the yield adopting the 2-acrylamide-2-methylpro panesulfonic acid sterling that purification process provided by the invention prepares is 80%～85%, purity > 99%。
Detailed description of the invention
Technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described embodiment is only a part of embodiment of the present invention, rather than whole embodiments。Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art obtain under not making creative work premise, broadly fall into the scope of protection of the invention。
The invention provides the process for purification of a kind of 2-acrylamide-2-methylpro panesulfonic acid crude product, including:
Adopt acrylonitrile washing 2-acrylamide-2-methylpro panesulfonic acid crude product, obtain washed product；
Described washed product and low-carbon alcohols are mixed, obtains mixture；
After being lowered the temperature by described mixture, insulation, then carries out solid-liquid separation, obtains solid matter；
Described solid matter is dried, obtains 2-acrylamide-2-methylpro panesulfonic acid sterling。
The present invention adopts acrylonitrile washing 2-acrylamide-2-methylpro panesulfonic acid crude product, obtains washed product。In the present invention, the water content in described acrylonitrile is preferably 1wt%～5wt%；It is more preferably 2wt%～4wt%；It most preferably is 3wt%。The method of described washing is not had special restriction by the present invention, adopts washing technology scheme well known to those skilled in the art to carry out washing。In the present invention, the number of times of described washing is preferably 2 times～3 times。In the present invention, the temperature of described washing is preferably 10 DEG C～40 DEG C, more preferably 20 DEG C～30 DEG C。In the present invention, the time of described washing is preferably 0.5 hour～2 hours；It is more preferably 1 hour～1.5 hours。
The preparation method of described 2-acrylamide-2-methylpro panesulfonic acid crude product is not had special restriction by the present invention, adopts the not purified product that the method for the 2-of preparation acrylamide-2-methylpro panesulfonic acid well known to those skilled in the art prepares to can be used in the present invention。In an embodiment of the present invention, the purity of described 2-acrylamide-2-methylpro panesulfonic acid crude product is 90%～95%。
After obtaining washed product, described washed product and low-carbon alcohols are mixed by the present invention, obtain mixture。In an embodiment of the present invention, the carbon number in described low-carbon alcohols is 1～4；It is preferably methanol, ethanol, ethylene glycol, normal propyl alcohol or isopropanol。In the present invention, the consumption of described low-carbon alcohols is the low-carbon alcohols of every gram of preferred 1mL～5mL of washed product, more preferably the low-carbon alcohols of 2mL～4mL, it is most preferred that for the low-carbon alcohols of 2.5mL～3.5mL。In the present invention, the temperature of described mixing is preferably 40 DEG C～50 DEG C；It is more preferably 42 DEG C～48 DEG C；It most preferably is 44 DEG C～46 DEG C。In an embodiment of the present invention, the time of described mixing is preferably 1 hour～3 hours；It is more preferably 1.5 hours～2.5 hours；It most preferably is 2 hours。
After obtaining mixture, the present invention is incubated after being lowered the temperature by described mixture, then carries out solid-liquid separation, obtains solid product。In the present invention, the temperature of described cooling is preferably 20 DEG C～35 DEG C；It is more preferably 23 DEG C～32 DEG C；It most preferably is 25 DEG C～30 DEG C。In the present invention, the time of described insulation is preferably 5 hours～10 hours；It is more preferably 6 hours～9 hours；It most preferably is 7 hours～8 hours。
In the present invention, the method for described solid-liquid separation is preferably centrifugal filtration。
After obtaining solid matter, described solid matter is dried by the present invention, obtains 2-acrylamide-2-methylpro panesulfonic acid sterling。In the present invention, described dry method is preferably vacuum drying。In the present invention, described dry temperature is preferably 50 DEG C～70 DEG C；It is more preferably 55 DEG C～65 DEG C；It most preferably is 58 DEG C～62 DEG C。In an embodiment of the present invention, the described dry time is preferably 4 hours～6 hours；It is more preferably 4.5 hours～5.5 hours；It most preferably is 5 hours。
Adopting liquid-phase chromatographic analysis to test the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that process for purification provided by the invention prepares, the actual conditions of described liquid-phase chromatographic analysis test is:
ZorbaxSAX chromatographic column,
Mobile phase is 0.1mol/LKH2PO4Solution,
Flow rate of mobile phase is 1.0ml/min,
UV-detector。
Test result is, the purity > 99% of the 2-acrylamide-2-methylpro panesulfonic acid sterling that process for purification provided by the invention prepares。
Raw material used in following example of the present invention is commercial goods。
Embodiment 1
Acrylonitrile is cooled to 0 DEG C, after adding oleum in described acrylonitrile, passes into isobutene., react 2 hours at 45 DEG C, obtain 2-acrylamide-2-methylpro panesulfonic acid crude product。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid crude product that the detection embodiment of the present invention 1 prepares；Testing result is, the purity of the 2-acrylamide-2-methylpro panesulfonic acid crude product that the embodiment of the present invention 1 prepares is 95%。
At 25 DEG C, 1L is adopted to wash above-mentioned 2-acrylamide-2-methylpro panesulfonic acid crude product 2 times containing the acrylonitrile that water quality is 3%, each wash time is 1h, then in glass reaction still, add the dehydrated alcohol of 400mL, add the 2-acrylamide-2-methylpro panesulfonic acid crude product after the above-mentioned washing of 200g when stirring；Being cooled to 20 DEG C after stirring 2 hours at 40 DEG C, maintain this temperature 6 hours, solid is isolated in centrifugal filtration；Being put in by the solid obtained in 50 DEG C of vacuum drying ovens and dry 6h, obtain 2-acrylamide-2-methylpro panesulfonic acid sterling, yield is 83.3%。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that the process for purification that the detection embodiment of the present invention 1 provides prepares；Testing result is, the purity of the sterling that the process for purification that the embodiment of the present invention 1 provides prepares is 99.63%。
Embodiment 2
The 2-acrylamide-2-methylpro panesulfonic acid crude product that embodiment 1 is prepared by the method described in embodiment 1 is refined, and as different from Example 1, adopts the condition being cooled to 20 DEG C in the condition alternative embodiment 1 being cooled to 30 DEG C, and yield is 80.2%。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that the process for purification that the detection embodiment of the present invention 2 provides prepares；Testing result is, the purity of the sterling that the process for purification that the embodiment of the present invention 2 provides prepares is 99.57%。
Embodiment 3
The 2-acrylamide-2-methylpro panesulfonic acid crude product that embodiment 1 is prepared by the method described in embodiment 1 is refined, as different from Example 1, the condition being incubated 6 hours after maintaining cooling in the insulation condition alternative embodiment 1 of 8 hours after adopting maintenance cooling, yield is 81.5%。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that the process for purification that the detection embodiment of the present invention 3 provides prepares；Testing result is, the purity of the sterling that the process for purification that the embodiment of the present invention 3 provides prepares is 99.45%。
Embodiment 4
The 2-acrylamide-2-methylpro panesulfonic acid crude product that embodiment 1 is prepared by the method described in embodiment 1 is refined, and as different from Example 1, adopts the dehydrated alcohol of 400mL in the dehydrated alcohol alternative embodiment 1 of 600mL, and yield is 80.6%。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that the process for purification that the detection embodiment of the present invention 4 provides prepares；Testing result is, the purity of the sterling that the process for purification that the embodiment of the present invention 4 provides prepares is 99.17%。
Embodiment 5
The 2-acrylamide-2-methylpro panesulfonic acid crude product that embodiment 1 is prepared by the method described in embodiment 1 is refined, and as different from Example 1, adopts the dehydrated alcohol in absolute methanol alternative embodiment 1, and yield is 82.8%。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that the process for purification that the detection embodiment of the present invention 5 provides prepares；Testing result is, the purity of the sterling that the process for purification that the embodiment of the present invention 5 provides prepares is 99.40%。
Embodiment 6
The 2-acrylamide-2-methylpro panesulfonic acid crude product that embodiment 1 is prepared by the method described in embodiment 1 is refined, and as different from Example 1, adopts the dehydrated alcohol in isopropanol alternative embodiment 1, and yield is 80.7%。
Method described in technique scheme, the purity of the 2-acrylamide-2-methylpro panesulfonic acid sterling that the process for purification that the detection embodiment of the present invention 6 provides prepares；Testing result is, the purity of the sterling that the process for purification that the embodiment of the present invention 6 provides prepares is 99.25%。
As seen from the above embodiment, the invention provides the process for purification of a kind of 2-acrylamide-2-methylpro panesulfonic acid crude product, including: adopt acrylonitrile washing 2-acrylamide-2-methylpro panesulfonic acid crude product, obtain washed product；Described washed product is mixed with low-carbon alcohols, obtains mixture；After being lowered the temperature by described mixture, insulation, then carries out solid-liquid separation, obtains solid matter；Described solid matter is dried, obtains 2-acrylamide-2-methylpro panesulfonic acid sterling。The present invention adopts acrylonitrile and low-carbon alcohols, as double solvents, the crude product of 2-acrylamide-2-methylpro panesulfonic acid is purified process, and processing method is simple, and need not adopt water as solvent, makes the product purity after purification and yield higher。
Claims (10)
1. a process for purification for 2-acrylamide-2-methylpro panesulfonic acid crude product, including:
Adopt acrylonitrile washing 2-acrylamide-2-methylpro panesulfonic acid crude product, obtain washed product；
Described washed product and low-carbon alcohols are mixed, obtains mixture；
After being lowered the temperature by described mixture, insulation, then carries out solid-liquid separation, obtains solid matter；
Described solid matter is dried, obtains 2-acrylamide-2-methylpro panesulfonic acid sterling。
2. process for purification according to claim 1, it is characterised in that the carbon number in described low-carbon alcohols is 1～4。
3. process for purification according to claim 2, it is characterised in that described low-carbon alcohols is methanol, ethanol, ethylene glycol, normal propyl alcohol or isopropanol。
4. process for purification according to claim 1, it is characterised in that the consumption of described low-carbon alcohols is the low-carbon alcohols that every gram of washed product adopts 1mL～5mL。
5. process for purification according to claim 1, it is characterised in that the water content in described acrylonitrile is 1wt%～5wt%。
6. process for purification according to claim 1, it is characterised in that the purity of described 2-acrylamide-2-methylpro panesulfonic acid crude product is 90%～95%。
7. process for purification according to claim 1, it is characterised in that the temperature of described mixing is 40 DEG C～50 DEG C, and the time of described mixing is 1～3h。
8. process for purification according to claim 1, it is characterised in that the temperature of described cooling is 20 DEG C～35 DEG C。
9. process for purification according to claim 8, it is characterised in that the time of described insulation is 5 hours～10 hours。
10. process for purification according to claim 1, it is characterised in that described dry temperature is 50 DEG C～70 DEG C。
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Cited By (1)
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| CN114195685A (en) * | 2020-09-18 | 2022-03-18 | Spcm股份公司 | Purification method of 2-acrylamide-2-methylpropanesulfonic acid |
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Cited By (2)
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| CN114195685A (en) * | 2020-09-18 | 2022-03-18 | Spcm股份公司 | Purification method of 2-acrylamide-2-methylpropanesulfonic acid |
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Application publication date: 20160622 |