CN101066940B - Prepn process of 2-acryl amido-2-methyl propane sulfonic acid - Google Patents
Prepn process of 2-acryl amido-2-methyl propane sulfonic acid Download PDFInfo
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- CN101066940B CN101066940B CN2007100090667A CN200710009066A CN101066940B CN 101066940 B CN101066940 B CN 101066940B CN 2007100090667 A CN2007100090667 A CN 2007100090667A CN 200710009066 A CN200710009066 A CN 200710009066A CN 101066940 B CN101066940 B CN 101066940B
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- sulfonic acid
- propane sulfonic
- methyl propane
- acrylamido
- acetic acid
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- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title abstract description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 59
- 238000001035 drying Methods 0.000 claims abstract description 25
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 24
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000001953 recrystallisation Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- -1 propylene nitrile Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 3
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 18
- 238000001514 detection method Methods 0.000 description 17
- 239000000843 powder Substances 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 239000003519 biomedical and dental material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is preparation process of 2-acryl amido-2-methyl propane sulfonic acid, and relates to compound synthesis process. The preparation process has low cost and high product purity, and is suitable for industrial production. The preparation process includes the following steps: reaction of acrylonitrile, fuming sulfuric acid and introduced gasified isobutene in a reactor at the temperature from -4 deg.c to 0 deg.c, cooling, separating and drying to obtain coarse 2-acryl amido-2-methyl propane sulfonic acid product; dissolving the coarse product in 0.5-50 wt% concentration acetic acid solution at 70-100 deg.c, cooling to 65-60 deg.c, vacuum distilling to separate 1/3-1/2 of the acetic acid solution, cooling to 20 deg.c, maintaining for 1 hr and centrifugally drying to operate high purity 2-acryl amido-2-methyl propane sulfonic acid.
Description
Technical field
The present invention relates to a kind of synthetic method of compound, especially relate to the preparation method of a kind of 2-acrylamido-2-methyl propane sulfonic acid.
Background technology
Because 2-acrylamido-2-methyl propane sulfonic acid (AMPS) is a kind of water miscible sulfonic acid group with strong anionic property, make it have dyeing affinity, electroconductibility, ion exchangeable and to the good tolerance of divalent cation; Amide group makes it have good stability to hydrolysis, antiacid, alkali resistant and thermostability; And active pair of key makes it have addition and polymerization, can produce multipolymer with multiple hydro carbons monomer.Therefore, chemical fields such as biomedical material, man-made fiber, magnetic pipe recording material, weaving (spinning, dyeing), plastics, papermaking, coating, sewage disposal and oil production have been widely used in, produced the static inhibitor, staining agent, dispersion agent, water-retaining agent, flocculation agent, suds-stabilizing agent, speciality coating, oilfield chemistry agent of excellent property etc., be with broad prospects for development water-soluble organic in the middle of monomer.
The synthetic of AMPS is seen in foreign patent the earliest, along with updating of synthetic method, new method again successively in national applications such as American and Britain, moral, days patent.Domestic study on the synthesis about AMPS has a small amount of bibliographical information, focuses on the optimization experiment condition to improve productive rate and product purity.These class methods are raw material with iso-butylene, vinyl cyanide and sulfuric acid, adopt the synthetic AMPS in single stage method laboratory, and generally about 90%, product purity reaches as high as 99.62% to its productive rate.Chinese patent (CN91110942.0) has been reported the method for the synthetic AMPS in a kind of laboratory, be provided at the compound that adds the organic acid anhydride class in the reaction mixture, make the monomeric prepared in laboratory method of the higher AMPS of purity by vinyl cyanide, sulfuric acid and iso-butylene single step reaction, its productive rate does not coexist 75%～90% with reaction conditions.The industrial production aspect, being reported in the specialist additive existence is raw material with vinyl cyanide, iso-butylene, the trimethyl carbinol and the vitriol oil down, one-step synthesis AMPS, purity can reach (polymerization-grade) more than 97%; With iso-butylene, vinyl cyanide and oleum is raw material, low-temperature atmosphere-pressure, sulfonation addition reaction, make thick AMPS, obtain the AMPS product of higher degree, its reaction yield 〉=90% (iso-butylene meter) by solvent wash, recrystallization, refining yield 〉=60% (with thick AMPS, the wt meter).
Summary of the invention
Purpose of the present invention aims to provide and a kind ofly reduces cost, the product purity height, be suitable for the preparation method of the 2-acrylamido-2-methyl propane sulfonic acid of suitability for industrialized production.
The present invention includes following steps:
1) the raw material propylene nitrile is added in the reactor;
2) under-4～0 ℃ of temperature, at the uniform velocity add oleum in the reactor;
3) add after oleum finishes, the iso-butylene back of at the uniform velocity vaporizing is fed reactor and reacts, reaction finishes back constant temperature, cooling, after separating drying, thick 2-acrylamido-2-methyl propane sulfonic acid product;
4) the preparation water content is 0.5%～50% acetic acid;
5) acetic acid is added in the recrystallization still, the thick 2-acrylamido-2-methyl propane sulfonic acid of step 2 preparation is put into the recrystallization still and mixed with acetic acid, be warmed up to 70～100 ℃, dissolving is carried out underpressure distillation, the acetic acid separated with 1/3～1/2 when being cooled to 65～60 ℃ then, distillation finishes, continue at the uniform velocity to be cooled to 20 ℃, centrifugal drying behind the constant temperature 1h obtains high purity 2-acrylamido-2-methyl propane sulfonic acid product then.
The purity of vinyl cyanide is best 〉=and 99.0%, moisture is 0.05%～1%, preferably moisture is 0.2%～0.7%.Reaction mass vinyl cyanide in molar ratio: oleum: iso-butylene is (5～10): 1: 1, be preferably (7～9): 1: 1.
The free state SO of oleum
3Content is 0.1%～20%, is preferably 2%～8%.The purity of iso-butylene is best 〉=and 99.0%, iso-butylene vaporized at the uniform velocity to feed the temperature that reactor reacts be 35～45 ℃ in the back, mixing speed is 120～160r/min.The water content of acetic acid is preferably 5%～20%.Acetic acid add-on in molar ratio: thick the 2-acrylamido-2-methyl propane sulfonic acid add-on is (2～8): 1, be preferably (3～5): 1, acetic acid is added in the recrystallization still, the thick 2-acrylamido-2-methyl propane sulfonic acid of step 3 preparation is put into still and mixed with acetic acid, preferably be warmed up to 85～90 ℃ of dissolvings.
The present invention is by using excessive propene nitrile double as solvent, not only can improve the monomeric products yield, and the product crystalline particle is thicker, be easy to from reactant, separate out, be easy to dry the separation, the product yield in recrystallization stage reaches more than 85% (in the thick 2-acrylamido-2-methyl propane sulfonic acid), and purity (liquid chromatograph detection) reaches more than 99.0%.Vinyl cyanide and the also retortable recovery of acetic acid after synthetic and re-crystallization step is centrifugal utilize again, save cost, are suitable for suitability for industrialized production.
Embodiment
The invention will be further described below by embodiment.
Embodiment 1
720kg high-purity propylene nitrile is changed in the reactor with pump, turn on agitator, mixing speed 120～160r/min is cooled to-4 ℃ with refrigerating fulid, is formulated into 0.2% with vinyl cyanide in the reactor is moisture in the temperature-fall period.Cooling finishes, in 40min with 147.5kg free state SO
3Content is that 3.5% high purity oleum at the uniform velocity is added drop-wise in the reactor, and this process temperature in the kettle is controlled at-2 ± 1 ℃; Sulfuric acid dropwises, and with hot water material in reactor is warming up to 15 ℃ rapidly, begins to feed high-purity isobutylene simultaneously.In the logical iso-butylene process,, feed from the reactor bottom through the metering back with gaseous form then and react at first with liquid iso-butylene vaporization; Iso-butylene feeding amount is 90kg, time 90min (0-60min flow 70kg/h; 60-90min flow 40kg/h), require steadily evenly to add, this process temperature in the kettle is controlled at 39 ± 1 ℃.The iso-butylene adding finishes, and material in reactor is carried out constant temperature handle, and temperature in the kettle is controlled at 39 ± 1 ℃, time 1h.Constant temperature finishes, and with material in reactor uniform decrease in temperature to 10 ℃, separates dry then in 1h.Get the thick 2-acrylamido of white powder-2-methyl propane sulfonic acid product 292kg after the drying, product purity is 95.7% (liquid chromatographic detection).The high purity Glacial acetic acid is mixed with moisture 10% aqueous acetic acid as solvent.The 1200kg acetate solvate is changed in the recrystallization still, and turn on agitator adds the thick 2-acrylamido-2-methyl propane sulfonic acid that makes in the reactor, begins to be warming up to 87 ℃ of dissolvings then, and this process control time finishes in 35min.After the dissolving, begin to lower the temperature with refrigerating fulid.When temperature in the kettle is reduced to 65 ℃, will introduce vacuum in the still, heat and carry out underpressure distillation, in 120min, distill out the 500kg solvent.Distillation finishes, and continues to lower the temperature with refrigerating fulid, at the uniform velocity is cooled to 20 ℃ in 2h, then centrifugal drying behind the constant temperature 1h.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 256kg after the drying, yield 88% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 99.3% (liquid chromatographic detection).
Embodiment 2
Reactor and working method with embodiment 1 only change the vinyl cyanide add-on into 850kg.Get the thick 2-acrylamido of 270kg white powder-2-methyl propane sulfonic acid product after the drying respectively, product purity is 95.2% (liquid chromatographic detection).Recrystallization still and working method with embodiment 1.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 239kg after the drying, yield 89% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 99.2% (liquid chromatographic detection).
Embodiment 3
Reactor and working method with embodiment 1 only change the vinyl cyanide add-on into 450kg.Temperature control instability in the reaction process, the reaction mass thickness, the cooling difficulty was not easily separated after reaction was finished.Get the thick 2-acrylamido of 262kg pale yellow powder shape-2-methyl propane sulfonic acid product after the drying respectively, product purity is 93.2% (liquid chromatographic detection).Recrystallization still and working method with embodiment 1 only are adjusted to 2% with the acetate solvate water content.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 235kg after the drying, yield 90% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 98.3% (liquid chromatographic detection).
Embodiment 4
With reactor and the working method of embodiment 1, identical feed ratio is only with free state SO in the high purity oleum
3Content is adjusted into 0.05%.Get the thick 2-acrylamido of 278kg white powder-2-methyl propane sulfonic acid product after the drying, product purity is 93.2% (liquid chromatographic detection).Recrystallization still and working method with embodiment 1 are adjusted to 40% with the acetate solvate water content.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 248kg after the drying respectively, yield 89% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 98.6% (liquid chromatographic detection).
Embodiment 5
With reactor and the working method of embodiment 1, identical vinyl cyanide and iso-butylene are only with free state SO in the high purity oleum
3Content is adjusted into 15%.Get the thick 2-acrylamido of 283kg pale yellow powder shape-2-methyl propane sulfonic acid product after the drying, product purity is 93.4% (liquid chromatographic detection).Recrystallization still and working method with embodiment 1 are adjusted to 18% with the acetate solvate water content.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 250kg after the drying respectively, yield 88% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 99.2% (liquid chromatographic detection).
Embodiment 6
With reactor and the working method of embodiment 1, identical oleum and iso-butylene are adjusted into 0.05% with vinyl cyanide is moisture.Get the thick 2-acrylamido of 285kg pale yellow powder shape-2-methyl propane sulfonic acid product after the drying, product purity is 93.5% (liquid chromatographic detection).Recrystallization still and working method with embodiment 1 are adjusted to 18% with the acetate solvate water content.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 254kg after the drying respectively, yield 89% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 99.0% (liquid chromatographic detection).
Embodiment 7
With reactor and the working method of embodiment 1, identical oleum and iso-butylene only are adjusted into 0.8% with vinyl cyanide is moisture.Get the thick 2-acrylamido of 268kg white powder-2-methyl propane sulfonic acid product after the drying, product purity is 93.2% (liquid chromatographic detection).Recrystallization still and working method with embodiment 1, the acetate solvate water content is adjusted to 10%, dissolve thick 2-acrylamido-2-methyl propane sulfonic acid down in 95 ℃, all the other operations are with embodiment 1, get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 237kg after the drying respectively, yield 88% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 99.3% (liquid chromatographic detection).
Embodiment 8
With reactor and the working method of embodiment 1, identical reaction mass, the temperature-rise period after sulfuric acid dropwised omits, and the reaction heat controlled temperature of logical iso-butylene process is at 30 ± 1 ℃.Get the thick 2-acrylamido of white powder-2-methyl propane sulfonic acid product 250kg after the drying, product purity is 93.6% (liquid chromatographic detection).With recrystallization still and the working method of embodiment 1, only vacuum distillation process is removed.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product 166kg after the drying, yield 66% (in thick 2-acrylamido-2-methyl propane sulfonic acid), product purity is 99.4% (liquid chromatographic detection).
Embodiment 9
With reactor and the working method of embodiment 1, identical reaction mass omits thermostatic process, and the reaction heat controlled temperature of logical iso-butylene process is at 45 ± 1 ℃.Get the thick 2-acrylamido of white powder-2-methyl propane sulfonic acid product after the drying.
With recrystallization still and the working method of embodiment 1, only vacuum distillation process is removed.Get white powder high purity 2-acrylamido-2-methyl propane sulfonic acid product after the drying.
Claims (4)
1.2-the preparation method of acrylamido-2-methyl propane sulfonic acid is characterized in that it may further comprise the steps:
1) the raw material propylene nitrile is added in the reactor purity of vinyl cyanide 〉=99.0%;
2) under-4～0 ℃ of temperature, oleum is at the uniform velocity added in the reactor free state SO of oleum
3Content is 0.1%～20%;
3) after the adding oleum finishes, at the uniform velocity vaporizing iso-butylene afterwards, the feeding reactor reacts, the temperature of reaction is 35～45 ℃, mixing speed is 120～160r/min, and reaction finishes back constant temperature, cooling, after separating drying, get thick 2-acrylamido-2-methyl propane sulfonic acid product, in molar ratio, vinyl cyanide: oleum: iso-butylene is 7～9: 1: 1, and the purity of iso-butylene 〉=99.0%;
4) the preparation water content is 0.5%～50% acetic acid;
5) acetic acid is added in the recrystallization still, the thick 2-acrylamido-2-methyl propane sulfonic acid of step 3) preparation is put into the recrystallization still and mixed with acetic acid, be warmed up to 70～100 ℃, dissolving is carried out underpressure distillation, the acetic acid separated with 1/3～1/2 when being cooled to 65～60 ℃ then, distillation finishes, continue at the uniform velocity to be cooled to 20 ℃, centrifugal drying behind the constant temperature 1h obtains 2-acrylamido-2-methyl propane sulfonic acid product then.
2. the preparation method of 2-acrylamido as claimed in claim 1-2-methyl propane sulfonic acid, the water content that it is characterized in that vinyl cyanide is 0.05%～1%.
3. the preparation method of 2-acrylamido as claimed in claim 1-2-methyl propane sulfonic acid, the water content that it is characterized in that acetic acid is 5%～20%.
4. the preparation method of 2-acrylamido as claimed in claim 1-2-methyl propane sulfonic acid, it is characterized in that acetic acid is added in the recrystallization still, the thick 2-acrylamido-2-methyl propane sulfonic acid of step 3 preparation is put into still and mixed with acetic acid, be warmed up to 85～90 ℃ of dissolvings.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2007100090667A CN101066940B (en) | 2007-06-06 | 2007-06-06 | Prepn process of 2-acryl amido-2-methyl propane sulfonic acid |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2007100090667A CN101066940B (en) | 2007-06-06 | 2007-06-06 | Prepn process of 2-acryl amido-2-methyl propane sulfonic acid |
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| CN101066940A CN101066940A (en) | 2007-11-07 |
| CN101066940B true CN101066940B (en) | 2010-09-22 |
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Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8247601B2 (en) * | 2007-12-06 | 2012-08-21 | Toagosei Co., Ltd. | 2-acrylamide-2-methylpropanesulfonic acid and process for producing the same |
| CN102452963B (en) * | 2010-10-15 | 2014-02-05 | 中国石油化工股份有限公司 | Production method for 2-acrylamide-2-methylpro panesulfonic acid |
| CN102452962A (en) * | 2010-10-15 | 2012-05-16 | 中国石油化工股份有限公司 | Synthesis method of 2-acrylamide-2-methylpropanesulfonic acid |
| CN102351744A (en) * | 2011-08-25 | 2012-02-15 | 潍坊泉鑫化工有限公司 | Synthesis process for 2-acrylamido-2-methyl propane sulfonic acid through continuous method |
| CN102952050A (en) * | 2011-08-30 | 2013-03-06 | 中国石油化工股份有限公司 | 2-acrylamide-2-methylpropanesulfonic acid (AMPS) and refining method thereof |
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| US4219498A (en) * | 1978-06-12 | 1980-08-26 | Nitto Chemical Industry Co., Ltd. | Process for preparing highly pure-2-acrylamido-2-methylpropanesulfonic acid |
| CN1072406A (en) * | 1991-11-21 | 1993-05-26 | 中国科学院长春应用化学研究所 | Synthesis of acrylamide alkyl sulfonic acid |
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