CN105085331B - A kind of synthetic method of Methacrylamide propyl group N, N dimethyl propylene sulfonate - Google Patents
A kind of synthetic method of Methacrylamide propyl group N, N dimethyl propylene sulfonate Download PDFInfo
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- CN105085331B CN105085331B CN201410198820.6A CN201410198820A CN105085331B CN 105085331 B CN105085331 B CN 105085331B CN 201410198820 A CN201410198820 A CN 201410198820A CN 105085331 B CN105085331 B CN 105085331B
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- methacrylamide
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- propyl group
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Abstract
The present invention discloses a kind of Methacrylamide propyl group N, N dimethyl propylene sulfonate（DMAPPS）Synthetic method, including following content：Mass ratio is weighed first as 2:1~9:1 N（3 dimethylamino-propyls）Methacrylamide（DMAP）With 1,3 propane sultones（PS）, and to N（3 dimethylamino-propyls）1,3 propane sultones are added in Methacrylamide；Then 0.5 4h is reacted at a temperature of 10 DEG C~60 DEG C；Last filtered, extracting, dry obtained Methacrylamide propyl group N, N dimethyl propylene sulfonate.This method has the advantages that without using solvent, the reaction time is short, product yield is high, suitable for commercial Application.
Description
Technical field
The present invention relates to a kind of synthetic method of Methacrylamide propyl group-N, N- dimethyl propylene sulfonate.
Background technology
Methacrylamide propyl group-N, N- dimethyl propylene sulfonate（DMAPPS）It is that a kind of methacryl amine spreads out
Biomonomer, its molecular formula are：C12H24N2O4S, molecular weight are：292.395 molecular structural formula is as follows：
DMAPPS is a kind of white powdery solids, soluble in water, is slightly soluble in most of organic solvent.DMAPPS is as one
Kind of new type water-solubility ampholytic monomer, because its chemically and thermally stability is good, hydration capability is strong and containing be not easy to be influenceed by solution ph,
The quaternary ammonium cation and sulfonate anionic of the number such as insensitive to salt and receive much attention.With only containing a kind of the water-soluble of electric charge
Property anionic or cation type polymer are compared, and DMAPPS performance is more unique.In intermolecular and molecule intrachain force
Properties, comprise only a kind of polyelectrolyte of electric charge, and electrostatic force is only electrostatic repulsion；And for amphiphilic polymers, it is quiet
Electro ultrafiltration may be either repulsion, or gravitation, the relative number depending on positive and negative charge in strand.In terms of SOLUTION PROPERTIES,
Macromolecular net charge be zero or strand on the equal amphiphilic polymers of positive and negative charge group numbers, the viscosity of its saline solution is not
But do not reduce, increase on the contrary, show fairly obvious " anti-polyelectrolyte effect " (antipolyelectrolyte
effect).This unique property assigns amphiphilic polymers unique function.At present, in view of formation temperature is high in oil drilling
And salinity it is high the characteristics of, to make to reach wellbore stability in drilling process, the effect of safety drilling, polymer must have very
Tackifying ability and very strong heatproof well, salt resistance and anti-shear ability.Obviously, DMAPPS amphiphilic polymers can meet such
It is required that.
The content of the invention
In view of the shortcomings of the prior art, the present invention provides a kind of Methacrylamide propyl group-N, N- dimethyl propylene sulfonic acid
The synthetic method of salt.This method has the advantages that without using solvent, the reaction time is short, product yield is high, suitable for commercial Application.
A kind of Methacrylamide propyl group-N, N- dimethyl propylene sulfonate（DMAPPS）Synthetic method, the synthesis
Method includes following content：Mass ratio is weighed respectively first as 2:1~9:1 N-（3- dimethylamino-propyls）Methacrylamide
（DMAP）And PS（PS）, and to N-（3- dimethylamino-propyls）1 is added in Methacrylamide, 3-N-morpholinopropanesulfonic acid
Lactone；Then 0.5-4h is reacted at a temperature of 10 DEG C~60 DEG C；Last filtered, extracting, dry obtained Methacrylamide
Propyl group-N, N- dimethyl propylene sulfonate.
N- described in the inventive method（3- dimethylamino-propyls）Methacrylamide（DMAP）With 1, in 3-N-morpholinopropanesulfonic acid
Ester（PS）Mass ratio be 2.5:1~8:1.PS can be added drop-wise to N-（3- dimethylamino-propyls）Metering system
In acid amides, N- directly can also be disposably added to（3- dimethylamino-propyls）In Methacrylamide, the preferred side of being directly added into
Formula.Using N- during directly disposable addition（3- dimethylamino-propyls）Methacrylamide（DMAP）And PS
（PS）Mass ratio is 5.2:1~7.8:1.Using N- during the mode of dropwise addition（3- dimethylamino-propyls）Methacrylamide（DMAP）With
PS（PS）Mass ratio is 2.5:1~5:1, PS can be heated and melted before dropwise addition.
Preferably 1-3h is reacted in the inventive method at a temperature of 20~55 DEG C.
Extraction solvent selects methanol or ethanol, preferred alcohol in the inventive method, and extraction times are 1~3h.Drying temperature
For 30~50 DEG C, drying time is 10~20h.
Compared with prior art, a kind of Methacrylamide propyl group-N, N- dimethyl propylene sulfonate of the present invention
（DMAPPS）Synthetic method have the following advantages that：
（1）PS is added to excessive N- by the inventive method（3- dimethylamino-propyls）Methacryl
In amine, excessive N-（3- dimethylamino-propyls）Methacrylamide acts not only as raw material and participates in reaction, and can
Play a part of solvent, it is solvent to avoid in conventional method using poisonous acetone, is a kind of green synthetic method；
（2）The inventive method is by controlling PS and N-（3- dimethylamino-propyls）Methacrylamide
Quality when feeding mode, solves PS and N-（3- dimethylamino-propyls）Methacrylamide is according to routine
When method is directly reacted（Generally equimolar is than reaction）, it is impossible to the problem of obtaining monomer DMAPPS；
（3）The inventive method is solvent without using poisonous acetone, have it is green, the reaction time is short, product receive
The advantages that rate is high, simple to operate, suitable for commercial Application.
Embodiment
The effect of the inventive method and effect are illustrated with reference to embodiment, but following examples are not formed to this
The limitation of scheme of the invention.
Embodiment 1
Weigh 630gDMAP to be put into reactor, be then placed in thermostat water bath, heat and start to stir.Weigh again
122gPS, it is added directly into DMAP, reaction temperature is 35 DEG C, and DMAPPS crude product is obtained after stirring reaction 1.5h.Will
DMAPPS crude products are transferred in large stretch of filter paper and wrapped, and are positioned in Soxhlet extraction device, the use of ethanol are solvent extraction 1h, take out
Filter paper bag is placed in drying box after carrying, is dried at 40 DEG C, finally gives pure DMAPPS monomers, yield is
91.5%,（Yield is to actually obtain the quality of product and stoichiometrically react the obtained ratio of theoretical product quality, under
Together）.
Embodiment 2
Weigh 940gDMAP to pour into reactor, be then placed in thermostat water bath, heat and start to stir.Weigh again
122gPS, it is added directly into DMAP, reaction temperature is 25 DEG C, and DMAPPS crude product is obtained after stirring reaction 3h.Will
DMAPPS crude products are transferred in large stretch of filter paper and wrapped, and are positioned in Soxhlet extraction device, the use of ethanol are solvent extraction 3h, take out
Filter paper bag is placed in drying box after carrying, is dried at 50 DEG C, finally gives pure DMAPPS monomers, yield is
93.4%。
Embodiment 3
Weigh 785gDMAP to pour into reactor, be then placed in thermostat water bath, heat and start to stir.Weigh again
122gPS, it is added directly into DMAP, reaction temperature is 55 DEG C, and DMAPPS crude product is obtained after stirring reaction 2h.Will
DMAPPS crude products are transferred in large stretch of filter paper and wrapped, and are positioned in Soxhlet extraction device, the use of ethanol are solvent extraction 2.5h,
Filter paper bag is placed in drying box after extracting, is dried at 35 DEG C, finally gives pure DMAPPS monomers, yield is
91.0%。
Embodiment 4
Weigh 314gDMAP to pour into reactor, be then placed in thermostat water bath, heat and start to stir.Weigh again
122gPS, it is slowly added dropwise in DMAP, stirring reaction 1.5h is added dropwise, reaction temperature is 30 DEG C, obtains the thick of DMAPPS
Product.DMAPPS crude products are transferred in large stretch of filter paper and wrapped, are positioned in Soxhlet extraction device, are taken out using ethanol for solvent
1h is carried, filter paper bag is placed in drying box after extracting, is dried at 35 DEG C, finally gives pure DMAPPS monomers, is produced
Rate is 90.4%.
Comparative example 1（Directly react）
According to stoichiometric proportion DMAP：PS is 1:1 reaction.Weigh 170gDMAP to pour into reactor, be then placed in constant temperature
In water-bath, heat and start to stir.122gPS is weighed again, is added directly into DMAP, and reaction temperature is 20 DEG C, stirring reaction
Mass polymerization product is obtained after 0.5h, without DMAPPS monomers, yield 0.During according to stoichiometric reaction, produced in reaction
Substantial amounts of heat can not disperse in time, and temperature moment steeply rises, and causes raw material DMAP and product DMAPPS all to polymerize.
Comparative example 2（Conventional method, using acetone as solvent reaction）
Weigh 180gDMAP to pour into reactor, be then placed in thermostat water bath, heat and start to stir.Weigh again
122gPS is dissolved in 1200g acetone, and mixed solution is added directly into DMAP, and reaction temperature is 60 DEG C, after stirring reaction 4h
To DMAPPS crude product.DMAPPS crude products are transferred in large stretch of filter paper and wrapped, are positioned in Soxhlet extraction device, are used
Ethanol is solvent extraction 2h, and filter paper bag is placed in drying box after extracting, dries, finally gives pure at 35 DEG C
DMAPPS monomers, yield 80.3%.
Claims (9)
- A kind of 1. synthetic method of Methacrylamide propyl group-N, N- dimethyl propylene sulfonate, it is characterised in that：Distinguish first Mass ratio is weighed as 2:1~9:1 N-（3- dimethylamino-propyls）Methacrylamide and PS, and to N- （3- dimethylamino-propyls）PS is added in Methacrylamide；Then reacted at a temperature of 10 DEG C~60 DEG C 0.5-4h；Last filtered, extracting, dry obtained Methacrylamide propyl group-N, N- dimethyl propylene sulfonate.
- 2. according to the method for claim 1, it is characterised in that： N-（3- dimethylamino-propyls）Methacrylamide and 1, The mass ratio of 3-N-morpholinopropanesulfonic acid lactone is 2.5:1~8:1.
- 3. according to the method for claim 1, it is characterised in that：PS is added drop-wise to N-（3- dimethylaminos third Base）In Methacrylamide or directly disposably it is added to N-（3- dimethylamino-propyls）In Methacrylamide.
- 4. the method according to claim 1 or 3, it is characterised in that：PS is directly disposably added to N- （3- dimethylamino-propyls）In Methacrylamide.
- 5. according to the method for claim 3, it is characterised in that：The N- weighed during using directly disposable addition（3- diformazans Aminopropyl）Methacrylamide and PS mass ratio are 5.2:1~7.8:1.
- 6. according to the method for claim 3, it is characterised in that：Using N- during the mode of dropwise addition（3- dimethylamino-propyls）First Base acrylamide and PS mass ratio are 2.5:1~5:1.
- 7. according to the method for claim 1, it is characterised in that：N-（3- dimethylamino-propyls）Methacrylamide and 1,3- Propane sultone reacts 1-3h at a temperature of 20~55 DEG C.
- 8. according to the method for claim 1, it is characterised in that：Extraction solvent selects methanol or ethanol, and extraction times are 1~ 3h。
- 9. according to the method for claim 1, it is characterised in that：Drying temperature be 30~50 DEG C, drying time be 10~ 20h。
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| CN107022050B (en) | 2017-05-16 | 2018-02-06 | 西南石油大学 | A kind of sulphonate betaine type hydrophobic associated polymer and preparation method thereof |
| CN107814881A (en) * | 2017-11-14 | 2018-03-20 | 西南石油大学 | A kind of quick copolymer gel of temperature sensitive salt and preparation method thereof |
| CN109336790A (en) * | 2018-10-31 | 2019-02-15 | 湖北吉和昌化工科技有限公司 | The synthetic method of (3- (methacrylamido) propyl) dimethyl (3- sulfopropyl) ammonium hydroxide inner salt |
| CN117343233B (en) * | 2023-12-05 | 2024-03-08 | 西南石油大学 | Temperature-resistant acidizing steering agent, preparation method and carbonate reservoir acidizing acid liquor |
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| CN103781808A (en) * | 2011-09-01 | 2014-05-07 | 宝洁公司 | Soil adsorption polymers |
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| CN103781808A (en) * | 2011-09-01 | 2014-05-07 | 宝洁公司 | Soil adsorption polymers |
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| Electrophoresis in gels containing zwitterionic groups;Leonard M. Hjelmeland et al.;《Electrophoresis》;19811231;第2卷;第82—90页 * |
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