CN103130688A - Preparing method of 2-acrylamide alkyl sulfonic acid - Google Patents
Preparing method of 2-acrylamide alkyl sulfonic acid Download PDFInfo
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- CN103130688A CN103130688A CN2013100520660A CN201310052066A CN103130688A CN 103130688 A CN103130688 A CN 103130688A CN 2013100520660 A CN2013100520660 A CN 2013100520660A CN 201310052066 A CN201310052066 A CN 201310052066A CN 103130688 A CN103130688 A CN 103130688A
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- CN
- China
- Prior art keywords
- alkyl sulfonic
- acrylamide alkyl
- oleum
- olefin
- alpha
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- -1 alkyl sulfonic acid Chemical compound 0.000 title abstract description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000004711 α-olefin Substances 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 6
- 235000011149 sulphuric acid Nutrition 0.000 abstract 4
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- 238000012805 post-processing Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- MPLIJWMZXSTSDQ-UHFFFAOYSA-N 2-(prop-2-enoylamino)dodecane-1-sulfonic acid Chemical compound CCCCCCCCCCC(CS(O)(=O)=O)NC(=O)C=C MPLIJWMZXSTSDQ-UHFFFAOYSA-N 0.000 description 2
- XNYBUIUOTDPTMX-UHFFFAOYSA-N 2-(prop-2-enoylamino)hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCC(CS(O)(=O)=O)NC(=O)C=C XNYBUIUOTDPTMX-UHFFFAOYSA-N 0.000 description 2
- ZJCOXZXHUMVTTE-UHFFFAOYSA-N 2-(prop-2-enoylamino)tetradecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCC(CS(O)(=O)=O)NC(=O)C=C ZJCOXZXHUMVTTE-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a preparing method of 2-acrylamide alkyl sulfonic acid and belongs to the technical field of high-polymer material monomer synthesis, wherein the 2-acrylamide alkyl sulfonic acid is a polymerizable surface active agent monomer. Raw materials of the 2-acrylamide alkyl sulfonic acid are alpha-olefin, industrial grade acrylonitrile, 10%-20% of fuming sulphuric acid and sulfur trioxide. A quantity relative ratio of the raw materials is n (the alpha-olefin): n (sulfuric acid (H2SO4) +sulfur trioxide (SO3)): n (the acrylonitrile) = 1: (0.95-1.15): (5-11), wherein n (H2SO4): n (SO3) =1: (1.23-2.28). 10%-20% of the fuming sulphuric acid and the sulfur trioxide serve as sulfonating agents. The industrial grade acrylonitrile which serves as the raw material and solvent can be directly applied without dehydration. In the process of preparation, no dehydration agent is needed. In addition, the yield of target products is larger than 80%, the purity is larger than 98%, the reaction process is stable and easy to control, the post processing of the products and the solvent is simple, and the industrial production is facilitated.
Description
Technical field:
The present invention relates to a kind of preparation method of 2-acrylamide alkyl sulfonic acids, 2-acrylamide alkyl sulfonic acids is a kind of polymerisable surfactant monomer, belongs to macromolecular material monomer synthesis technical field.
Technical background:
Vinyl monomer and polymkeric substance thereof with sulfonic acid group, the special performance that not only has strong acid, and hydrolysis, temperature and divalent cation had specific stability, application has in some aspects become irreplaceable monomer and polymkeric substance, as more and more wider in the range of application aspect letex polymerization, printing and dyeing, oil field, water treatment industry.
2-acrylamido-2-methyl propane sulfonic acid (AMPS) is the amide group sulfonic acid monomer that can make high-molecular weight polymer that early obtains.Developed on this basis acrylamido chain alkyl sulfonic acid, as 2-acrylamido n-Hexadecane sulfonic acid (AMC
16S), 2-acrylamido dodecane sulfonic acid (AMC
12S), 2-acrylamido tetradecane sulfonic acid (AMC
14S).With hydrophobic chain alkyl and hydrophilic sulfonic group, amide group, be a kind of polymerisable surface active monomer in this type of monomer molecule.The monomer copolymerizations such as such monomer and acrylamide, can obtain having the multipolymer of ionic surfactant side chain, this analog copolymer obtains good salt resistance by the congregation that salt brings out the surfactivity side chain, can be used for oil-displacing agent and drilling fluid additive under the high temperature and high salinity formation condition.
periodical 1998 during chemical industry, 12 (4) disclose a kind of synthetic 2-acrylamido dodecane sulfonic acid, chemical science and technology 2000, 8 (1) disclose a kind of synthetic 2-acrylamido tetradecane sulfonic acid, guizhou chemical industry 1997, 4 disclose a kind of synthetic 2-acrylamido n-Hexadecane sulfonic acid, but this class acrylamido chain alkyl sulfonic acid is all to use vinyl cyanide in synthetic, long-chain olefin and oleum are raw material, oleum used must be 50% above oleum (being solid-state under room temperature), not easy to operate in preparation, and need to adopt dewatering agent, brought trouble for product later stage purifying.
Summary of the invention:
Purpose of the present invention is exactly that to be to overcome the preparation of prior art not easy to operate, and needs to adopt dewatering agent, and the problem of product later stage purifying and solvent recuperation trouble provides a kind of preparation method of 2-acrylamide alkyl sulfonic acids.
A kind of preparation method of 2-acrylamide alkyl sulfonic acids by take alpha-olefin and technical grade vinyl cyanide, oleum and sulphur trioxide as raw material, is the n(alpha-olefin by molar ratio): n (H
2SO
4+ SO
3): n (vinyl cyanide)=1:(0.95～1.15): (5～11), wherein n (H
2SO
4): n (SO
3)=1:(1.23～2.28) be prepared from, comprise the following steps:
(1) vinyl cyanide, alpha-olefin are added in reaction flask with stirring, thermometer, dropping funnel, airway and condenser, stir and with the cryosel water-bath, the temperature of system is down to below-5 ℃ afterwards, add oleum in system in 30～60 minutes, keep temperature of reaction to be no more than 10 ℃ in adition process;
(2) after oleum adds, pass into sulphur trioxide in the system of step (1) gained in 45～90 minutes, keep temperature of reaction to be no more than 15 ℃ in adition process, after the sulphur trioxide amount reaches, add 2～5mL water, stirring reaction 3～10h under room temperature;
(3) the 2-acrylamide alkyl sulfonic acids crystallization that step (2) reaction is generated is filtered with glass sand core funnel, the gained crystal is respectively with after vinyl cyanide washing 2 times, in 60 ℃ of lower vacuum-dryings, namely get product of the present invention, reusable edible after the distillation of filtrate process or fractionation.
In described oleum, free sulfur trioxide content is 10%～20%, can be by the vitriol oil of 25% oleum and 98% according to the different ratios mixed preparing.
Described alpha-olefin is hendecene-1, laurylene-1, tridecylene-1, tetradecene-1, ten pentaenes-1, hexadecene-1,17 alkene-1, octadecylene-1 or 19 alkene-1.
The described oleum that first adds, then the order of addition(of ingredients) of logical sulphur trioxide, or for first leading to sulphur trioxide, then add the feed way of oleum.
The invention has the beneficial effects as follows: the oleum of employing 10%～20% and sulphur trioxide are as sulphonating agent, to the water content of vinyl cyanide without strict demand, industrial vinyl cyanide as raw material and solvent is directly used without dehydration, and do not adopt dewatering agent in preparation, the target product yield greater than 80%, purity is greater than 98%, reaction process is easily control steadily, and product and solvent aftertreatment are simple, are easy to suitability for industrialized production; The present invention can be used for the polymerisable surfactant of letex polymerization with sulfonic group and two keys, also can be used for polymer oil-displacing agent, fracturing fluid gelatinizer and drilling fluid additive synthetic of printing and dyeing thickening material, the anti-salt of novel heatproof.
Embodiment:
The present invention will be further described below in conjunction with specific embodiment.But the present invention is not limited in following embodiment.
Embodiment 1:
According to the n(alpha-olefin): n (H
2SO
4+ SO
3): n (vinyl cyanide)=1:0.95:5, n (H
2SO
4): n (SO
3The ratio of)=1:2.28,265.3 gram vinyl cyanide, 196.37 gram tetradecene-1 are added in reaction flask with stirring, thermometer, dropping funnel, airway and condenser, stir and with the cryosel water-bath, the temperature of system is down to-5 ℃ afterwards, with adding the oleum of 35.52 grams 20% in 60 minutes clockwise systems, keep temperature of reaction to be no more than 10 ℃ in adition process; After oleum adds, pass into 45.67 gram sulphur trioxides in the clockwise system with 45 minutes, keep temperature of reaction to be no more than 15 ℃ in adition process, after the sulphur trioxide amount reaches, add 5mL water, stirring reaction 10h under room temperature; The 2-acrylamide alkyl sulfonic acids crystallization that reaction generates is filtered with glass sand core funnel, the gained crystal is respectively with after vinyl cyanide washing 2 times, in 60 ℃ of lower vacuum-dryings, obtain 278.3 gram products, in tetradecene-1, yield 80.2%, content 99.31%, platinum-cobalt colorimetric number is 3, filtrate through distillation or fractionation after recycle.
Embodiment 2:
According to the n(alpha-olefin): n (H
2SO
4+ SO
3): n (vinyl cyanide)=1:1.15:11, n (H
2SO
4): n (SO
3The ratio of)=1:1.23,583.66 gram vinyl cyanide, 168.32 gram laurylene-1 are added in reaction flask with stirring, thermometer, dropping funnel, airway and condenser, stir and with the cryosel water-bath, the temperature of system is down to-6 ℃ afterwards, with adding the oleum of 54.84 grams 10% in 30 minutes clockwise systems, keep temperature of reaction to be no more than 10 ℃ in adition process; After oleum adds, pass into 43.86 gram sulphur trioxides in the clockwise system with 90 minutes, keep temperature of reaction to be no more than 15 ℃ in adition process, after the sulphur trioxide amount reaches, add 2mL water, stirring reaction 3h under room temperature; The 2-acrylamide alkyl sulfonic acids crystallization that reaction generates is filtered with glass sand core funnel, the gained crystal is respectively with after vinyl cyanide washing 2 times, in 60 ℃ of lower vacuum-dryings, get 269.6 gram products, in laurylene-1, yield 84.5%, content 98.67%, platinum-cobalt colorimetric number is 4, filtrate through distillation or fractionation after recycle.
Embodiment 3:
According to the n(alpha-olefin): n (H
2SO
4+ SO
3): n (vinyl cyanide)=1:1:9, n (H
2SO
4): n (SO
3The ratio of)=1:1.84,477.54 gram vinyl cyanide, 224.43 gram hexadecene-1s are added in reaction flask with stirring, thermometer, dropping funnel, airway and condenser, stir and with the cryosel water-bath, the temperature of system is down to-8 ℃ afterwards, with adding the oleum of 40.63 grams 15% in 45 minutes clockwise systems, keep temperature of reaction to be no more than 10 ℃ in adition process; After oleum adds, pass into 45.71 gram sulphur trioxides in the clockwise system with 60 minutes, keep temperature of reaction to be no more than 15 ℃ in adition process, after the sulphur trioxide amount reaches, add 3.5mL water, stirring reaction 6h under room temperature; The 2-acrylamide alkyl sulfonic acids crystallization that reaction generates is filtered with glass sand core funnel, the gained crystal is respectively with after 350g vinyl cyanide washing 2 times, in 60 ℃ of lower vacuum-dryings, get 322.9 gram products, in hexadecene-1, yield 86.1%, content 99.12%, platinum-cobalt colorimetric number is 3, filtrate through distillation or fractionation after recycle.
According to the method for embodiment 3, only change alpha-olefin and consumption thereof, embodiment 4～9 test-results see Table 1.
Table 1 embodiment 4～9 is particular sheet as a result
| Embodiment | 4 | 5 | 6 | 7 | 8 | 9 |
| Alpha-olefin | Hendecene-1 | Tridecylene-1 | Ten pentaenes-1 | 17 alkene-1 | Octadecylene-1 | 19 alkene-1 |
| Consumption/gram | 154.3 | 182.31 | 210.42 | 238.42 | 252.48 | 266.51 |
| Product/gram | 244.9 | 277.1 | 309.0 | 330.3 | 330.9 | 330.7 |
| Yield/% | 80.3 | 83.2 | 85.6 | 84.9 | 82.1 | 80.21 |
| Content/% | 98.09 | 99.01 | 99.14 | 99.00 | 98.62 | 98.03 |
| Platinum-cobalt colorimetric | 4 | 5 | 4 | 4 | 5 | 4 |
The yield of above-described embodiment greater than 80%, purity is greater than 98%, platinum-cobalt colorimetric number value is less than or equal to 5, finds out thus, product yield of the present invention is higher, purity is very high.
Claims (5)
1. the preparation method of a 2-acrylamide alkyl sulfonic acids is characterized in that: by take alpha-olefin and technical grade vinyl cyanide, oleum and sulphur trioxide as raw material, be the n(alpha-olefin by molar ratio): n (H
2SO
4+ SO
3): n (vinyl cyanide)=1:(0.95～1.15): (5～11), wherein n (H
2SO
4): n (SO
3)=1:(1.23～2.28) be prepared from.
2. the preparation method of a kind of 2-acrylamide alkyl sulfonic acids according to claim 1 is characterized in that: comprise the following steps:
(1) vinyl cyanide, alpha-olefin are added in reaction flask with stirring, thermometer, dropping funnel, airway and condenser, stir and with the cryosel water-bath, the temperature of system is down to below-5 ℃ afterwards, add oleum in system in 30～60 minutes, keep temperature of reaction to be no more than 10 ℃ in adition process;
(2) after oleum adds, pass into sulphur trioxide in the system of step (1) gained in 45～90 minutes, keep temperature of reaction to be no more than 15 ℃ in adition process, after the sulphur trioxide amount reaches, add 2～5mL water, stirring reaction 3～10h under room temperature;
(3) the 2-acrylamide alkyl sulfonic acids crystallization that step (2) reaction is generated is filtered with glass sand core funnel, and the gained crystal is respectively with after vinyl cyanide washing 2 times, in 60 ℃ of lower vacuum-dryings and get final product.
3. the preparation method of a kind of 2-acrylamide alkyl sulfonic acids according to claim 1 and 2 is characterized in that: in described oleum, free sulfur trioxide content is 10%～20%.
4. the preparation method of a kind of 2-acrylamide alkyl sulfonic acids according to claim 1 and 2, it is characterized in that: described alpha-olefin is hendecene-1, laurylene-1, tridecylene-1, tetradecene-1, ten pentaenes-1, hexadecene-1,17 alkene-1, octadecylene-1 or 19 alkene-1.
5. the preparation method of a kind of 2-acrylamide alkyl sulfonic acids according to claim 1 and 2 is characterized in that: the described oleum that first adds, then the order of addition(of ingredients) of logical sulphur trioxide, or for first leading to sulphur trioxide, then add the feed way of oleum.
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|---|---|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312550A (en) * | 2014-08-22 | 2015-01-28 | 中国石油化工集团公司 | Anionic surfactant for micro-foam drilling fluid and preparation method thereof |
| CN104311455A (en) * | 2014-06-05 | 2015-01-28 | 中国石油化工集团公司 | Preparation method of 2-acrylamido-2-methylpropane sulfonic acid |
| CN105461598A (en) * | 2014-09-03 | 2016-04-06 | 中国石油化工股份有限公司 | Acrylamide monomer, acrylamide copolymer and preparation method therefor and applicationthereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104311455A (en) * | 2014-06-05 | 2015-01-28 | 中国石油化工集团公司 | Preparation method of 2-acrylamido-2-methylpropane sulfonic acid |
| CN104311455B (en) * | 2014-06-05 | 2018-02-27 | 中国石油化工集团公司 | A kind of preparation method of 2 acrylamido 2 methyl-prop (alkane) sulfonic acid |
| CN104312550A (en) * | 2014-08-22 | 2015-01-28 | 中国石油化工集团公司 | Anionic surfactant for micro-foam drilling fluid and preparation method thereof |
| CN104312550B (en) * | 2014-08-22 | 2018-11-06 | 中国石油化工集团公司 | A kind of anionic micro-foam drilling fluid surfactant and preparation method thereof |
| CN105461598A (en) * | 2014-09-03 | 2016-04-06 | 中国石油化工股份有限公司 | Acrylamide monomer, acrylamide copolymer and preparation method therefor and applicationthereof |
| CN105461598B (en) * | 2014-09-03 | 2017-09-29 | 中国石油化工股份有限公司 | Acrylamide monomers, acrylamide based copolymer and its preparation method and application |
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| Publication number | Publication date |
|---|---|
| CN103130688B (en) | 2017-05-17 |
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