CN102380330A - Cathode-non-amphoteric ion type gemini surfactant and synthesis method - Google Patents
Cathode-non-amphoteric ion type gemini surfactant and synthesis method Download PDFInfo
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Abstract
The invention relates to cathode-non-amphoteric ion type gemini surfactant and a synthesis method. Surface activity is high, critical micelle concentration is low, the synthesis method is simple, and reaction conditions are moderate. The surfactant is methylene-double- dodecyl polyoxyethylene ether benzene sulfonic acid sodium salt, and the code of the surfactant is YF-n. The synthesis method includes steps that p-hydroxybenzenesulfonic acid and formaldehyde liquor are added in a three-opening bottle and are reacted for 0.5 hour to 1 hour at the temperature of 90 DEG C, so that methylene-double- p-hydroxybenzenesulfonic acid is prepared, then laurinol polyoxyethylene ether and SOC12 are added in the three-opening bottle, are reacted for 10 hours to 12 hours at the temperature of 70 DEG C to 80 DEG C, are neutralized by NaOH liquor to alkalescence and are static to be layered, an organic solvent layer is washed by diethyl ether and dried at a constant temperature, so that chlorohydrin polyoxyethylene ether is prepared, two intermediate products including the methylene-double- p-hydroxybenzenesulfonic acid and the chlorohydrin polyoxyethylene ether are reacted for 20 hours to 30 hours at the temperature of 80 DEG C, and then the end product YF-n is obtained. The cathode-non-amphoteric ion type gemini surfactant and the synthesis method have the advantages that synthesis procedures are simple, reaction conditions are moderate and surface activity of objective substances is excellent, and are used for oilfield development.
Description
Technical field
The present invention relates to a kind of the moon-non-amphoteric ion type Gemini surface active agent and synthetic method that is used for crude oil exploitation, Chemical Manufacture high-duty detergent, solubilizer and emulsifying agent.
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 (cmc) 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 " " dimeric surfactant " etc.1974, Deinega etc. synthesized one group of novel amphipathic molecule, and its molecular structure is to be the center with the linking group, two hydrophilic ion heads are coupled together, each ion head each with a hydrocarbon connection of oil loving long-chain.Okahara in 1988 etc. are synthetic and studied the two alkane chain surfactants that connect ion head base with flexible group.Menger had synthesized the two alkane chain surfactants that connect ion head base with rigid radical in 1991; He gives a name for such amphiphile, amphiphilic molecule: " Gemini " (title " Gemini " astronomically) surfactant, the same year, Rosen group adopted the name of " Gemini ".Rosen group in 1993 and Zana group have also comparatively systematically been synthesized this type surfactant and have been studied their surface property.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.
Except high surface; The Gemini surfactant also has the advantage that conventional surfactants does not possess: good solubilising property; Low Krafft point can obviously reduce its application of temperature; Good bactericidal property, the 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.
Also can be divided into cationic, anionic, nonionic and amphoteric ion type by the type of hydrophilic radical with the same Gemini surfactant of traditional surfactant.Their synthetic method is varied, and performance is different.For these four kinds of dissimilar Gemini surface active agents relevant report is arranged all in document; This paper has the electric charge identical with reservoir shale to the surfactant of dual anion type; Less in rock surface absorption, be expected to be used for displacing fluid and obtain more outstanding displacement usefulness.And in anion surfactant; The hydrophilic group of sulfonic acid (salt) type belongs to forceful electric power and separates group, compares with carboxyl to have better salt tolerance and temperature tolerance, but considers that the salt-resistance of sulfonate surfactant is limited; And that the non-ionic surface active agent advantage is an anti-salt property is strong; Characteristics such as critical micelle concentration is low, and the performance of anti-polyvalent cation is good, but in the stratum poor stability; Adsorbance is higher than anion surfactant; So consider to combine both to introduce in the same molecular formula, the compound amphoteric surfactant of nonionic and anion designs two kinds of hydrophilic radicals of different nature (non-ionic group and anionic group) in same surfactant molecule, can have the advantage of anion and non-ionic surface active agent concurrently; Form the amphoteric surfactant of mutual supplement with each other's advantages, function admirable, in the hope of better surface-active, heat-resistant salt-resistant property and stable are preferably arranged.
Summary of the invention
The objective of the invention is to: have higher surface activity in order to make surfactant, through the synthetic a series of type YF-n Gemini surface active agents of the ethoxylated dodecyl alcohol that adds different polymerization degree; Its synthetic method is simple simultaneously, reaction condition is gentle relatively, special a kind of the moon-non-amphoteric ion type Gemini surface active agent and the synthetic method that propose.
In order to achieve the above object; The present invention adopts following technical scheme: a kind of the moon-non-amphoteric ion type Gemini surface active agent; Chemical name is that methylene-two-to dodecyl APEO benzene sulfonic acid sodium salt, this Gemini surface active agent code name is YF-n, and its structural formula is following:
Wherein, n=5-50, n are the degree of polymerization.
The synthetic method of this Gemini surface active agent is: in the there-necked flask that agitator, reflux condensate device and dropping funel are installed; The p-hydroxybenzenyl sulfonate solution that adds 0.5mol; Volume is 100ml; Under agitation dropwise adding quality hundred public concentration and be 37% 0.2mol formalin volume is 20ml, and the mol ratio of its p-hydroxybenzenyl sulfonate and formaldehyde is 2:0.8 ~ 0.95, adds hydrochloric acid hierarchy of control pH=2 ~ 3.Heat temperature raising to 90 ℃, isothermal reaction 0.5 ~ 1h stops heating and stirs, the adding suitable quantity of water if material thickens reacts fully and carries out, and treats to use the Rotary Evaporators solvent evaporated after the system cooling, makes intermediate methylene-two-p-hydroxybenzenyl sulfonate; , the there-necked flask of absorption plant adds 0.15 mol ethoxylated dodecyl alcohol, code name AEO then in being housed
9Volume is 100ml, adds 50 ml pyridines and makes solvent or solvent-free, agitator, the slow SOCl that drips 0.20mol in there-necked flask
2, volume is 15ml, its AEO
9With SOCl
2Mol ratio be 1:1.1 ~ 1.3, be 70 ~ 80 ℃ of down reaction 10 ~ 12 h in temperature, reaction system is cooled off; Use mass percentage concentration be 15% NaOH solution to be neutralized to pH be 7 ~ 8, reactant is moved into static layering in the separatory funnel, lower floor separates for the inorganic salts water layer; The upper strata is that organic solvent layer is again with ether washing 4 ~ 5 times; Until non-stimulated smell,, make intermediate product chlorhydrin APEO with 40 ℃ of freeze-day with constant temperature of product; Last is in the there-necked flask of 11.3% sodium hydrate aqueous solution in that 150ml quality percentage composition is housed; The intermediate product methylene that makes above the adding-two-p-hydroxybenzenyl sulfonate 0.05mol is 27g; Under 80 ℃ of stirring conditions of constant temperature, adding the intermediate product chlorhydrin APEO 0.1mol that the front makes again is 60 g, and the mol ratio of its two reactant is 1:2, is 80 ℃ of reaction 20 ~ 30 h down in temperature; After reaction finishes; Use the Rotary Evaporators solvent evaporated, make finally that product methylene-two-to dodecyl APEO benzene sulfonic acid sodium salt, code name is YF-n.
Synthetic route is undertaken by following three step chemical reactions:
(1) condensation reaction (methylene-two-p-hydroxybenzenyl sulfonate):
(2) chlorination
(3) the O-alkylated reaction of the alkyl halide of chloro alcohol ether and condensation product
The checking of end-product chemistry: in above-mentioned chlorination, long-chain chloro alcohol ether and intermediate methylene bis p-hydroxybenzenyl sulfonate react, and raw material long-chain chloro alcohol ether chlorine exists with the covalency attitude, and the chlorine in the product is converted into ionic state.Therefore, utilize Cl
-With Ag
+Whether the chemical reaction that generates the AgCl white precipitate can carry out by confirmatory reaction.Experiment white precipitate occurred after finding to drip silver nitrate in the reaction system, we can say that having carried out alkyl substitution in the phaneroplasm system has chlorination chlorine to produce.
This research adopts infra-red sepectrometry that the various functional groups in the YF-n molecule have been carried out initial analysis.With YF-9 (being n=9) is that example is carried out spectrum analysis, with the sample preparation of KBr compressing tablet, with the Paragon 100 type infrared spectrometers that PE company produces product is made infrared analysis.
Main absworption peak is following:
2800-2900cm
-1Be CH
2Flexible peak of antisymmetry and CH
2The symmetrical stretching vibration peak; 1620-1450 v phenyl ring skeletal vibration peak, 1900,1700,800,500 is the substituted stretching vibration peak of phenyl ring 1-2-4; 1460cm
-1C-H methylene stretching vibration peak, 1380 cm
-1Be C-H methyl stretching vibration peak, 1260-1150 is the flexible peak of the antisymmetry of S=O; 1080-1010 cm
-1Symmetrical stretching vibration peak for S=O; 700-650cm
-1Stretching vibration peak for the S-O key; 1225-1220 cm
-1The O-H stretching vibration peak of vinethene.
Surface tension is the critical nature of liquid, and the capillary ability that surfactant reduces water is to estimate its surface-active important parameter.This research adopts the full-automatic surface tension instrument of BZY-1 type that the surface tension of product solution is measured, and makes this series of surfactants aqueous solution surface tension with concentration curve.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 YF-n series Gemini surface active agent are lower.Critical micelle concentration like YF-9 is 0.084 * 10
-3Mol/L is at critical micelle concentration lower surface tension force (γ
Cmc) be 29.5mN/m.
Compared with prior art, the present invention has following beneficial effect: (1) object of the present invention is a kind of new type amphoteric ion-type Gemini surface active agent, and such object is not seen bibliographical information so far; (2) synthetic method of the present invention is simple relatively, and synthesis program was made up of condensation reaction, chlorination and three steps of substitution reaction, and reaction condition is relatively gentleer, simple to operate; (3) object surface-active of the present invention is good; Its critical micelle concentration is 0.084 mmol/L; Be 1/117 of dodecyl sodium sulfate (9.8 mmol/L), the surface tension under critical micelle concentration is 29.5mN/m, than low 9.5 mN/m of dodecyl sodium sulfate (39.0 mN/m).
Description of drawings
Fig. 1 is the infrared spectrogram of product YF-9 of the present invention.
Fig. 2 is γ-C curve (30oC) of YF of the present invention-9, and γ is a surface tension, and C is a concentration.
Embodiment 1The preparation of intermediate product condensation product
In the there-necked flask that agitator, reflux condensate device and dropping funel are installed; The p-hydroxybenzenyl sulfonate solution 100ml of 0.5mol packs into; Under agitation use the normal pressure dropping funel dropwise to add the formalin 20ml that mass percentage concentration is 37 ℅, add hydrochloric acid hierarchy of control pH=2.5.Be warming up to 90 ℃, and isothermal reaction 0.5h, reaction stopped.If material thickens during this period, can suitably add the entry dilution, reaction can fully be carried out.Treat to use the Rotary Evaporators solvent evaporated then after the system cooling, dry 24h down, get sulfonic group intermediate product methylene-two-p-hydroxybenzenyl sulfonate at 60 ℃.
Embodiment 2The chloro of ethoxylated dodecyl alcohol
, the there-necked flask of absorption plant adds 0.15molAEO in being housed
9Volume is 100 mL, adds the 50ml pyridine and makes solvent (or solvent-free), starts stirring, in there-necked flask, slowly drips 0.2molSOCl
2Volume is 15ml, reacts 10 h down at 70 ℃, until no longer emitting HCl and SO
2Till.Stop reaction, with reactant cooling, standing demix.It is 8 that the upper strata organic layer uses in 15% the NaOH solution with pH, moves in the separatory funnel and isolates the inorganic salts water layer, and organic solvent layer is again with ether washing 5 times, until having no irritating odor.40 ℃ of freeze-day with constant temperature of intermediate product to constant weight, are made the chlorhydrin APEO.
Embodiment 3Target product YF-9's is synthetic
In the mass concentration that 150ml is housed is the intermediate methylene-two-p-hydroxybenzenyl sulfonate 27g that adds 0.05mol in the there-necked flask of 11.3% sodium hydrate aqueous solution; Under 80 ℃ of stirring conditions of constant temperature, in solution, add 0.1mol chlorhydrin APEO 60g, under 80 ℃; Reaction 24h; Reaction is used the Rotary Evaporators solvent evaporated after finishing, and gets end product the moon-non-amphoteric ion type Gemini surface active agent YF-9.
Embodiment 4The surface-active of YF-n Gemini surface active agent is measured
Surface-active with YF-9 is determined as example.The YF-9 solution of preparation series concentration (mmol/L), this experiment adopt the full-automatic surface tension instrument of BZY-1 type to measure the surface tension of liquid solution, make γ-C curve.The critical micelle concentration that can get YF-9 by the slope of curve corresponding coordinate data jumpy is 0.084 * 10
-3Mol/L, the surface tension (γ under critical critical micelle concentration
Cmc) be 29.5mN/m.
Embodiment 5The infrared spectrum of YF-n surfactant
The infrared spectrum of YF-9 Gemini surface active agent that obtains through embodiment 1,2,3 is seen Fig. 1, is learnt by spectrum elucidation, and the target product of gained conforms to the expection product basically.
Claims (2)
1. the moon-non-amphoteric ion type Gemini surface active agent is characterized in that: chemical name is that methylene-two-to dodecyl APEO benzene sulfonic acid sodium salt, code name is YF-n, and its structural formula does
Wherein, n=5-50, n are the degree of polymerization.
2. the synthetic method of the moon of a claim 1-non-amphoteric ion type Gemini surface active agent is characterized in that: in there-necked flask, the p-hydroxybenzenyl sulfonate liquor capacity that adds 0.5mol is 100ml; Under agitation dropwise add 0.2mol formalin, volume is 20ml, and the mol ratio of its p-hydroxybenzenyl sulfonate and formaldehyde is 2:0.8 ~ 0.95; Add hydrochloric acid hierarchy of control pH=2 ~ 3, heat temperature raising to 90 ℃, isothermal reaction 0.5 ~ 1h; Stop heating and stirring; Treat to use the Rotary Evaporators solvent evaporated after the system cooling, make intermediate methylene-two-p-hydroxybenzenyl sulfonate; , the there-necked flask of absorption plant adds 0.15 mol ethoxylated dodecyl alcohol code name AEO in being housed
9Volume is 100 mL, adds 50 mL pyridines and makes solvent or solvent-free, agitator, the slow SOCl that drips 0.20mol in there-necked flask
2, volume is 15ml, its AEO
9With SOCl
2Mol ratio be 1:1.1 ~ 1.3, be 70 ~ 80 ℃ of down reaction 10 ~ 12 h in temperature, reaction system is cooled off; Using mass percentage concentration is that to be neutralized to pH be 7 ~ 8 for 15% NaOH solution; Reactant is moved into static layering in the separatory funnel, and lower floor separates for the inorganic salts water layer, and the upper strata is that organic solvent layer is again with ether washing 4 ~ 5 times; With 40 ℃ of freeze-day with constant temperature of product, make intermediate product chlorhydrin APEO; Last is in the there-necked flask of 11.3% sodium hydrate aqueous solution in that 150ml quality percentage composition is housed; The intermediate product methylene that makes above the adding-two-p-hydroxybenzenyl sulfonate 0.05mol is 27g, under 80 ℃ of stirring conditions of constant temperature, adds the intermediate product chlorhydrin APEO 0.1mol that the front makes again, is 60 g; The mol ratio of its two reactant is 1:2; In temperature is 80 ℃ of reaction 20 ~ 30 h down, and reaction is used the Rotary Evaporators solvent evaporated after finishing; Make finally that product methylene-two-to dodecyl APEO benzene sulfonic acid sodium salt, code name is YF-n.
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Cited By (12)
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|---|---|---|---|---|
| CN102895913A (en) * | 2012-09-28 | 2013-01-30 | 西南石油大学 | Cation type dimeric surfactant containing polyoxyethylene ether and synthetizing method of cation type dimeric surfactant |
| CN107384357A (en) * | 2017-06-14 | 2017-11-24 | 中国石油天然气股份有限公司 | Sub- surfactant of polyoxyethylene benzene sulfonic acid salt form Composite Double and preparation method thereof |
| CN107814755A (en) * | 2017-11-05 | 2018-03-20 | 青岛大学 | A kind of anionic gemini surfactant and preparation method thereof |
| CN108383758A (en) * | 2018-03-19 | 2018-08-10 | 青岛大学 | A kind of preparation method of sulfonic group anionic gemini surfactant |
| 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 |
| CN109652048A (en) * | 2018-12-28 | 2019-04-19 | 中国石油大学(北京) | A kind of compound oil displacement agent and its preparation method and application |
| CN109851530A (en) * | 2019-01-02 | 2019-06-07 | 中国石油天然气股份有限公司 | N, N, N ', four substituted diphenylamine ether sulfonate anionic gemini surfactant of N '-dodecyl and its synthesis |
| CN111068578A (en) * | 2019-12-23 | 2020-04-28 | 万华化学集团股份有限公司 | Surfactant, preparation method and application thereof |
| CN112195021A (en) * | 2020-11-16 | 2021-01-08 | 山东大明精细化工有限公司 | Gemini polyoxyethylene ether succinate surfactant for oil displacement and preparation method thereof |
| CN113429529A (en) * | 2021-07-12 | 2021-09-24 | 西南石油大学 | Preparation method of polyether-containing hydrophobic association polymer and application of polyether-containing hydrophobic association polymer in fracturing fluid |
| US11174424B2 (en) | 2019-01-02 | 2021-11-16 | Petrochina Company Limited | Core-shell structured anionic nano microemulsion system, and preparation and application thereof |
| CN115197106A (en) * | 2022-08-02 | 2022-10-18 | 吉林大学 | Anion-anion type gemini surfactant, preparation method thereof and application thereof in repairing halohydrocarbon polluted aquifer |
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| CN102895913A (en) * | 2012-09-28 | 2013-01-30 | 西南石油大学 | Cation type dimeric surfactant containing polyoxyethylene ether and synthetizing method of cation type dimeric surfactant |
| CN107384357A (en) * | 2017-06-14 | 2017-11-24 | 中国石油天然气股份有限公司 | Sub- surfactant of polyoxyethylene benzene sulfonic acid salt form Composite Double and preparation method thereof |
| CN107384357B (en) * | 2017-06-14 | 2019-10-11 | 中国石油天然气股份有限公司 | Polyoxyethylene-sub- surfactant of benzene sulfonic acid salt form Composite Double and preparation method thereof |
| CN107814755A (en) * | 2017-11-05 | 2018-03-20 | 青岛大学 | A kind of anionic gemini surfactant and preparation method thereof |
| CN107814755B (en) * | 2017-11-05 | 2021-10-29 | 青岛大学 | Anionic gemini surfactant and preparation method thereof |
| CN108383758A (en) * | 2018-03-19 | 2018-08-10 | 青岛大学 | A kind of preparation method of sulfonic group anionic gemini surfactant |
| CN108383758B (en) * | 2018-03-19 | 2021-10-29 | 青岛大学 | Preparation method of sulfonic anionic gemini surfactant |
| 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 |
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| CN109652048A (en) * | 2018-12-28 | 2019-04-19 | 中国石油大学(北京) | A kind of compound oil displacement agent and its preparation method and application |
| CN109652048B (en) * | 2018-12-28 | 2020-07-10 | 中国石油大学(北京) | Composite oil displacement agent and preparation method and application thereof |
| CN109851530B (en) * | 2019-01-02 | 2021-06-01 | 中国石油天然气股份有限公司 | N, N, N ', N' -dodecyl tetra-substituted diphenyl ether sulfonate anionic gemini surfactant and synthesis thereof |
| CN109851530A (en) * | 2019-01-02 | 2019-06-07 | 中国石油天然气股份有限公司 | N, N, N ', four substituted diphenylamine ether sulfonate anionic gemini surfactant of N '-dodecyl and its synthesis |
| US11174424B2 (en) | 2019-01-02 | 2021-11-16 | Petrochina Company Limited | Core-shell structured anionic nano microemulsion system, and preparation and application thereof |
| US11629283B2 (en) | 2019-01-02 | 2023-04-18 | Petrochina Company Limited | N,N,N′,N′-tetradodecyl-substituted diphenyl ether sulfonate anionic Gemini surfactant and synthesis method thereof |
| CN111068578A (en) * | 2019-12-23 | 2020-04-28 | 万华化学集团股份有限公司 | Surfactant, preparation method and application thereof |
| CN112195021A (en) * | 2020-11-16 | 2021-01-08 | 山东大明精细化工有限公司 | Gemini polyoxyethylene ether succinate surfactant for oil displacement and preparation method thereof |
| CN113429529A (en) * | 2021-07-12 | 2021-09-24 | 西南石油大学 | Preparation method of polyether-containing hydrophobic association polymer and application of polyether-containing hydrophobic association polymer in fracturing fluid |
| CN115197106A (en) * | 2022-08-02 | 2022-10-18 | 吉林大学 | Anion-anion type gemini surfactant, preparation method thereof and application thereof in repairing halohydrocarbon polluted aquifer |
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Application publication date: 20120321 |