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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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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| CN2007100090667A CN101066940B (en) | 2007-06-06 | 2007-06-06 | Prepn process of 2-acryl amido-2-methyl propane sulfonic acid |
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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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Denomination of invention: The preparation method of 2-acrylamido-2-methylpropanesulfonic acid Effective date of registration: 20220913 Granted publication date: 20100922 Pledgee: Bank of Weifang Limited by Share Ltd. Changyi branch Pledgor: WEIFANG GOLD STONE ENVIRONMENTAL TECHNOLOGY CO.,LTD. Registration number: Y2022980015023 |
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