CN1935346A - Bisamide bissulfosalt double surface active agent, and its synthesizing method - Google Patents
Bisamide bissulfosalt double surface active agent, and its synthesizing method Download PDFInfo
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- CN1935346A CN1935346A CN200610021918.XA CN200610021918A CN1935346A CN 1935346 A CN1935346 A CN 1935346A CN 200610021918 A CN200610021918 A CN 200610021918A CN 1935346 A CN1935346 A CN 1935346A
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- ethylenediamine
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- sodium sulfonate
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Abstract
The present invention relates to a kind of bisamide disulfonate double-component surfactant. Said surfactant is ethylene-bis (N-ethyl sulfonate group-alkylamide). Its synthesis method includes the following steps: (1), adding ethylenediamine aqueous solution into a reactor, slowly-drop-adding sodium 2-bromoethyl sulfonate solution, refluxing, stirring, making reaction for 6-8 hr in constant temperature water bath, retaining pH and making it be 8-10, water bath temperature is 50-70deg.C, adding ethyl alcohol, drying separated out solid to obtain sodium N1N1-diethylsulfonate ethylenediamine; and (2), adding the above-mentioned product into a reactor, stirring and adding acyl chloride, at the same time drop-adding triethylamine/acetone solution, retaining pH and making it be about 8, making reaction for 5-8 hr at room temperature, cooling, making precipitation, filtering, washing by using absolute alcohol and drying so as to obtain the invented surfactant.
Description
Technical field
The present invention relates to a kind of novel gemini surfactants and synthetic method thereof, particularly relate to a kind of bisamide bissulfosalt double surface active agent and synthetic method thereof.
Background technology
1971, Bunton etc. were to alkyl-α, the two methyl alkyl ammonium bromide [C of ω-two dialkyl group
mH
2m+1N
+(CH
3)
2Br
-]
2(CH
2)
5Be designated as (m-x-m, 2Br
-) surface nature and critical micelle concentration study, and investigated connecting group and be respectively hydrophilic, hydrophobic, the character of the Gemini surface active agent of flexibility and rigidity, these surfactants are called as " bi-quaternary ammonium salt " " Gemini surface active agent " (C.A.Bunton such as " dimeric surfactants ", L.Robinson.Catalysis of nucleophilcsubstituions by micelles of dieationic detergent[J] F.J.Org.Chem, 1971. (36): 2346-2352).1974, Deinega etc. have synthesized one group of novel amphipathic molecule, its molecular structure is to be the center with the linking group, two hydrophilic ion heads are coupled together, each ion head respectively with a hydrocarbon connection (Y.P.Zhu of oil loving long-chain, A.Masuyama, Deinega, Preparation and properties of double-or-triple-chainsurfactants with two sulfonate groups devised fromN-acyldiethanolamines[J] J.Am.Oil chem.Soc, 1991 (68): 539-543).
Okahara in 1988 etc. are synthetic and studied two alkane chain surfactants (the Zhu YP that connects ion head base with flexible group, Masuyama A, Okahara M.Preparation and surface activeproperties of amphipathic compounds with two sulfate groups and twolipoplulic alkyl chains[J] J Am Oil Chem Soc, 1990,67 (7): 459-463; Zhu.Y P, Masuyama A, Kirito M.Preparation and surface-activeproperties of new amphipathic compounds with two phosphate groupsand two long-chain alkyl groups[J] J Am Oil ChemSoc, 1991,68 (4): 268-271; Zhu Y.P, Masuyama A, Kiriito Y.Preparationand properties of double or triple-chain surfactants with twosulfonate groups derived from N-acyldiethanulamines[J] J Am OilChem Soc, 1991,68 (7) 539-543).The synthetic two alkane chain surfactants that connect ion head base with rigid radical of Menger in 1991, he gives a name for such amphiphile, amphiphilic molecule: " Gemini " (Shuangzi) surfactant (Menger FM, Littau CA.Geminisurfactants:synthesis and properties[J] .J.Am ChemSoc, 1991 (113): 1451-1452).The same year Rosen group adopted " Gemini " name (Rosen, MJ.Geminis:A new Generation of surfactants.[J] J ChemTechnol, 1993 (30): 23-33).Rosen group in 1993 and Zana group have also comparatively systematically been synthesized this class surfactant and have been studied their surface property (Zana R, Talmon Y.Dependence of aggregate morphology on structure of dimericsurfactants [J] Nature, 1993 (362): 228-229).Along with the further announcement of design feature, excellent properties and the structure-activity relationship of Gemini surface active agent, academia becomes increasingly active for the research of Gemini surface active agent.
At present, the Gemini surfactants that has synthesized anion, cation, nonionic and amphoteric ion type abroad.The nineties in last century, the Okahara research group of the Japanese Osaka university synthetic disulfonate anion Gemini surfactant that takes the lead in.Compare with traditional single linked list surface-active agent, these novel surfactants not only have good water-solubility, and can under extremely low concentration, form micella, also can more effectively reduce surface tension (the YP Zhu of solution, A Masuyama, M Okayharaet al.Preparation and surface active properties of amphipathiccompounds with to sulfate groups and two lipophilic alkyl chains.[J] .Am.Oil Chem.Soc., 1990 (67): 459-463; Y P Zhu, A Masuyama, T Nagataet al.Preparation and properties of double-chain surfactantsbearing two sulfonate groups[J] .Jpn.Oil Chem.Soc., 1991 (40): 473-477; Y P Zhu, A Masuyama, Y I Kirito et al.Preparation and properties ofglycerol-based double or triple-chain surfactants with twohydrophilic ionic groups [J] Am.Oil.Chem.Soc., 1992 (69): 626-632; Y PZhu, A Masuyama, Y Kobata et al.Doubl e-chain surfactants with twocarboxylate groups and their relation to similar double-chaincompounds [J] Colloid interf Sci, 1993 (158): 40-45).
Except high surface, the Gemini surfactant also has the advantage that conventional surfactants does not possess: good solubilising, low Krafft point can obviously reduce its application of temperature, good bactericidal property, special aggregated structure in dispersion and the separation function that shows, some Gemini surfactant solution promptly shows viscoelastic properties under low concentration.These character make the Gemini surfactant show wide application space.Because domestic research at the Gemini surfactant is started late, therefore the Gemini kinds of surfactants of exploitation is also more limited.
Summary of the invention
The object of the present invention is to provide a kind of bisamide bissulfosalt double surface active agent and synthetic method thereof, this surfactant has the bisamide disulfonate structure that ethylene connects, has higher surface activity, its synthetic method is simple, the reaction condition gentleness, easy and simple to handle and be easy to purify, separate.This surfactant is expected to be applied to produce household chemicals such as high-duty detergent, solubilizer, emulsifying agent, also can be used for alkali/surfactant binary combination flooding, alkali/surfactant/polymer ternary combination flooding in the tertiary oil recovery etc.
The novel gemini surfactants that the present invention synthesized is that ethylene-two (N-ethyl sulfonic acid alkali-alkylamide) brief note is TM, notes by abridging respectively as n=6,8,10,12,14 the time to be TM-6, TM-8, TM-10, TM-12, TM-14), its structural formula is as follows:
The reaction principle of synthetic this surfactant is as follows:
(1) N of ethylenediamine, N ' disulfonic acid (sodium) substitution reaction:
(2) N, the acylation reaction of N '-diethyl sulfonic acid (sodium) substituted ethylene diamine
This bisamide bissulfosalt double surface active agent and synthetic method thereof may further comprise the steps successively:
(1) in reactor, adds ethylenediamine solution, slowly drip 2-bromoethyl sodium sulfonate solution, the mol ratio of ethylenediamine and 2-bromoethyl sodium sulfonate is 1: 2, refluxes, stir, reaction is 6-8 hour in the water bath with thermostatic control, and pH keeps 8-10, and bath temperature is 50-70 ℃, after having reacted, add ethanol, will separate out solid dry intermediate product N, N '-diethyl sodium sulfonate ethylenediamine;
(2) add aqueous acetone solution in reactor, get a certain amount of N, N '-diethyl sodium sulfonate ethylenediamine adds in the reactor, stirs it is dissolved fully, under strong agitation, adds acyl chlorides, described acyl chlorides C then
nH
2n+1N among the COCl is respectively 7,9,11,13,15, N, the mol ratio of N '-diethyl sodium sulfonate ethylenediamine and acyl chlorides is 1: 2, drip triethylamine/acetone soln simultaneously, keeping pH is about 8, at room temperature reacts 5～8 hours, cooling has precipitation to separate out, suction filtration is used absolute ethanol washing, and dry back is this surfactant of target product.
The checking of the chemistry of intermediate product: in the substitution reaction of the amino hydrogen of above-mentioned ethylenediamine, the bromine that replaces reagent bromoethyl sodium sulfonate exists with the covalency attitude, and the bromine in the product is converted into ionic state.Therefore, utilize Br
-With Ag
+Whether the chemical reaction that generates the AgBr yellow mercury oxide can carry out by confirmatory reaction.The water-soluble back of the intermediate product that takes a morsel drips silver nitrate, light-yellow precipitate occurred, we can say the substitution reaction of having carried out amino hydrogen in the phaneroplasm system.Adopt organic solvent ethanol commonly used that middle product is carried out crystallization, have solid to separate out, carry out the intermediate product N of infrared spectrum analysis and target product, N '-diethyl sodium sulfonate group ethylenediamine conforms to substantially.
Compared with prior art, the present invention has following beneficial effect:
(1) surfactant of the present invention is to be the bisamide disulfonate type surfactant that connects base with the ethylene, and such object is not seen bibliographical information so far;
(2) synthetic method of the present invention is simple, and synthesis program was made of substitution reaction of ethylenediamine amino hydrogen atom and two steps of acylation reaction, the reaction condition gentleness, and simple to operate, product is easy to separate;
(3) object surface-active of the present invention is good, its critical micelle concentration is 0.5mmol/L, be 1/20 of dodecyl sodium sulfate (9.8mmol/L), the surface tension under critical micelle concentration is 29.7mN/m, than the low 9.3mN/m of dodecyl sodium sulfate (39.0mN/m).
Description of drawings
Fig. 1 is intermediate product N of the present invention, the infrared spectrogram of N '-diethyl sodium sulfonate ethylenediamine
Fig. 2 is the infrared spectrogram of Gemini surface active agent TM-10 of the present invention
Fig. 3 is γ-C curve (30 ℃) of TM-10 of the present invention
The specific embodiment
(1) intermediate product N, N '-diethyl sulfonic acid (sodium) ethylenediamine synthetic
Add ethylenediamine (0.06mol) and low amounts of water in the 250mL there-necked flask of agitator, thermometer, reflux condensing tube is housed, slowly drips 2-bromoethyl sodium sulfonate (0.1mol) solution, reaction is 6-8 hour in 50-70 ℃ of water bath with thermostatic control.Adding absolute ethyl alcohol then has solid to separate out, suction filtration, and 50 ℃ of oven dry obtain white solid 18.84g (yield is about 59%).
(2) TM-10's is synthetic
In the there-necked flask of 500mL, add intermediate 8.921g (0.0276mol), distilled water/acetone mixed solution (the v: v=1: 1) that adds 200mL then, make its dissolving, under strong agitation, slowly drip lauroyl chloride 15.097g (0.0690mol), drip triethylamine/acetone soln simultaneously, keeping the pH value is about 8, and reaction is 5-8 hour under the room temperature.Reactant liquor is but spent the night in refrigerator and cooled, have precipitation to separate out, suction filtration is used absolute ethanol washing three times again, and 40 ℃ of oven dry obtain the white solid powder and are TM-10, and weighing is 5.126g (yield is 27%)
(1) presses the method synthetic mesophase product N of embodiment 1, N '-diethyl sulfonic acid (sodium) ethylenediamine.
(2) TM-8's is synthetic
In the there-necked flask of 500mL, add intermediate 5.425g (0.0169mol), distilled water/acetone mixed solution (the v: v=1: 1) that adds 200mL then, make its dissolving, under strong agitation, slowly drip decanoyl chloride 8.048g (0.0423mol), drip triethylamine/acetone soln simultaneously, keeping the pH value is about 8, and reaction is 5-8 hour under the room temperature.Reactant liquor is but spent the night in refrigerator and cooled, have precipitation to separate out, suction filtration, absolute ethanol washing three times, 40 ℃ of oven dry obtain the white solid powder and are TM-8, and weighing is 3.352g (yield is 29%).
The surface-active of embodiment 3 TM series of surfactants is measured
Surface tension is the critical nature of liquid, the capillary ability that surfactant reduces water is to estimate its surface-active important parameter, adopt the around-France surface tension of circle to measure to product solution under the variable concentrations, make TM-10 aqueous solution surface tension with concentration curve, seen Fig. 3.Curve break obtains critical micelle concentration value (cmc) and the surface tension (γ under critical micelle concentration from figure
Cmc).Experiment finds that the critical micelle concentration and the surface tension under the critical micelle concentration of TM series of surfactants are lower, is 5.0 * 10 as the critical micelle concentration of TM-10
-4Mol/L is at critical micelle concentration lower surface tension force (γ
Cmc) be 29.7mN/m.
The infrared spectrum of embodiment 4 intermediate products and target product TM series of surfactants
The infrared spectrum of the intermediate product that obtains by embodiment 1 is seen Fig. 1; The infrared spectrum of TM-10 surfactant is seen Fig. 2, is learnt by spectrum elucidation:
Fig. 1 (intermediate product): 3448.16cm
-1Flexible stretching vibration peak for N-H; 2929cm
-1And 2848cm
-1Be respectively-CH
2-antisymmetry and symmetrical stretching vibration peak; 1638.70cm
-1Be the C-N stretching vibration; 1586.27cm
-1Flexural vibrations peak for secondary amine; 1474.85cm
-1For-CH
2The in-plane bending vibration peak of-N; 1417cm
-1-CH
2-SO
3The in-plane bending vibration peak; 1192.03cm
-1And 1052.23cm
-1For in the intermediate product-the flexible and symmetrical stretching vibration peak of the antisymmetry of S=O; 749.92cm
-1For-CH
2The in-plane bending vibration peak; 616.06cm
-1Antisymmetric stretching vibration peak for-S-O.
Fig. 2 (target product): 2956.88cm
-1And 1458cm
-1Be respectively CH
3The flexible and rocking vibration peak of antisymmetry; 1377.4cm
-1Be CH
3Face in the scissoring vibration peak; 2920.73cm
-1And 2851cm
-1For-CH
2-antisymmetry and symmetrical stretching vibration peak; 1467.75cm
-1And 721.202cm
-1Be respectively-CH
2-face in scissoring vibration and rocking vibration peak; 1639.7cm
-1Characteristic peak for the product teritary amide; 1436.54cm
-1Be carbonyl symmetrical stretching vibration peak; 1192.42cm
-1And 1063.5cm
-1For in the product-the flexible and symmetrical stretching vibration peak of the antisymmetry of S=O; 628.723cm
-1Antisymmetric stretching vibration peak for-SO.
Claims (2)
1 one kinds of bisamide bissulfosalt double surface active agents, this surfactant are ethylene-two (N-ethyl sulfonic acid alkali-alkylamides), and its structural formula is as follows:
The synthetic method of 2 Gemini surface active agents as claimed in claim 1 may further comprise the steps successively:
(1) in reactor, adds ethylenediamine solution, slowly drip 2-bromoethyl sodium sulfonate solution, the mol ratio of ethylenediamine and 2-bromoethyl sodium sulfonate is 1: 2, refluxes, stir, reaction is 6-8 hour in the water bath with thermostatic control, and pH keeps 8-10, and bath temperature is 50-70 ℃, after having reacted, add ethanol, will separate out solid dry intermediate product N, N '-diethyl sodium sulfonate ethylenediamine;
(2) add aqueous acetone solution in reactor, with N, N '-diethyl sodium sulfonate ethylenediamine adds in the reactor, stirs to add acyl chlorides C down
nH
2n+1COCl, described acyl chlorides C
nH
2n+1N among the COCl is respectively 7,9,11,13,15, N, the mol ratio of N '-diethyl sodium sulfonate ethylenediamine and acyl chlorides is 1: 2, drip triethylamine/acetone soln simultaneously, keeping pH is about 8, at room temperature reacts 5～8 hours, cooling has precipitation to separate out, suction filtration is used absolute ethanol washing, and dry back is this surfactant.
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| CN101343254B (en) * | 2008-07-09 | 2010-06-09 | 中北大学 | Gemini surfactant containing triazine ring |
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| CN101480590B (en) * | 2008-11-27 | 2011-05-18 | 齐齐哈尔大学 | Sulphonate Gemini surfactant and preparation method thereof |
| CN102351749A (en) * | 2011-08-05 | 2012-02-15 | 蚌埠丰原医药科技发展有限公司 | Benzenesulphonate anionic gemini surfactant and preparation method thereof |
| CN101554569B (en) * | 2009-04-21 | 2012-06-27 | 西安楚龙达化工有限公司 | Anionic type Gemini surface active agent and synthesizing method |
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| CN101745341B (en) * | 2009-12-18 | 2012-10-10 | 齐齐哈尔大学 | Gemini surface active agent and preparation method thereof |
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| CN101343254B (en) * | 2008-07-09 | 2010-06-09 | 中北大学 | Gemini surfactant containing triazine ring |
| CN101480590B (en) * | 2008-11-27 | 2011-05-18 | 齐齐哈尔大学 | Sulphonate Gemini surfactant and preparation method thereof |
| CN101554569B (en) * | 2009-04-21 | 2012-06-27 | 西安楚龙达化工有限公司 | Anionic type Gemini surface active agent and synthesizing method |
| CN101745341B (en) * | 2009-12-18 | 2012-10-10 | 齐齐哈尔大学 | Gemini surface active agent and preparation method thereof |
| CN102051243B (en) * | 2011-01-04 | 2013-07-24 | 中国石油大学(华东) | Diesel emulsion and preparation method thereof |
| CN102051243A (en) * | 2011-01-04 | 2011-05-11 | 中国石油大学(华东) | Diesel emulsion and preparation method thereof |
| CN102351749A (en) * | 2011-08-05 | 2012-02-15 | 蚌埠丰原医药科技发展有限公司 | Benzenesulphonate anionic gemini surfactant and preparation method thereof |
| CN102351749B (en) * | 2011-08-05 | 2013-06-12 | 蚌埠丰原医药科技发展有限公司 | Benzenesulphonate anionic gemini surfactant and preparation method thereof |
| CN102698648A (en) * | 2012-06-27 | 2012-10-03 | 东北石油大学 | Dendritic sulfonate-type tetramer surfactant and preparation method thereof |
| CN104478755A (en) * | 2014-12-12 | 2015-04-01 | 辽宁石油化工大学 | Preparation method of polymerizable zwitterionic surfactant |
| CN108547607A (en) * | 2018-03-07 | 2018-09-18 | 陕西友邦石油工程技术有限公司 | A kind of broadband for low-permeability oilfield stripper well is acidified seam method |
| CN109321225A (en) * | 2018-08-31 | 2019-02-12 | 中国石油天然气股份有限公司 | A kind of CO suitable for high temperature and high salt oil deposit2Foaming agent system and preparation method thereof |
| CN109321225B (en) * | 2018-08-31 | 2021-01-29 | 中国石油天然气股份有限公司 | CO suitable for high-temperature high-salinity oil reservoir2Foaming agent system and preparation method thereof |
| CN111346570A (en) * | 2020-03-23 | 2020-06-30 | 佛山市天宝利硅工程科技有限公司 | Sulfonic anion gemini surfactant and preparation method thereof |
| CN111450773A (en) * | 2020-04-17 | 2020-07-28 | 辽宁石油化工大学 | Amphiphilic water-based diionic amide surfactant and preparation method thereof |
| CN111450773B (en) * | 2020-04-17 | 2022-04-26 | 辽宁石油化工大学 | Amphiphilic water-based diionic amide surfactant and preparation method thereof |
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