CN105396504A - Anionic gemini surfactant and preparation method thereof - Google Patents
Anionic gemini surfactant and preparation method thereof Download PDFInfo
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- CN105396504A CN105396504A CN201510687619.9A CN201510687619A CN105396504A CN 105396504 A CN105396504 A CN 105396504A CN 201510687619 A CN201510687619 A CN 201510687619A CN 105396504 A CN105396504 A CN 105396504A
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
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- C07—ORGANIC CHEMISTRY
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
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Abstract
The invention discloses an anionic gemini surfactant and a preparation method thereof. The method comprises the following steps: mixing 10 parts of fatty alcohol, 3-6 parts of chloropropylene oxide, 0.3-0.5 parts of a phase-transfer catalyst and 3-6 parts of an alkaline compound, and reacting at 30-80DEG C for 3-5h to obtain a product A; adding the product A and 5-10 parts of succinic anhydride to 10-20 parts of tetrahydrofuran, mixing, and reacting for 10-15h to obtain a product B; mixing the product B with 3-6 parts of the alkaline compound, reacting for 2-3h, washing with ethanol, and carrying out reduced pressure distillation to remove tetrahydrofuran and ethanol in order to obtain a crude anionic gemini surfactant; and re-crystallizing with ethanol twice, and carrying out vacuum drying until constant weight in order to obtain the anionic gemini surfactant. Compared with the prior art, the preparation method has the advantages of simple preparation process, short reaction time and easy realization of industrial production due to addition of a cationic surfactant in the preparation process.
Description
Technical field
The present invention relates to surfactant and preparing technical field thereof, particularly a kind of anionic gemini surfactant and preparation method thereof.
Background technology
Surfactant, owing to can reduce oil water interfacial tension significantly, thus improves oil recovery factor field at chemical method and is used widely.Gemini surface active agent is as a kind of novel high performance surface activating agent, this kind of surfactant is owing to having linking group in structure, the electrostatic repulsion between hydrophilic group can be reduced, make the active component close contact of surfactant but do not destroy the hydrophilic profile of hydrophilic group; Again because molecule has two or more hydrophilic group and hydrophobic group, therefore this kind of surfactant has extremely strong micellization ability and surface/interface activity, the Gemini surface active agent of some structure has confirmed to reduce extremely low by oil water interfacial tension at much lower concentrations, the Gemini aggregation system of some structure shows good thickening property and viscoplasticity, also has water-soluble, resistance to hard water, emulsibility etc. preferably simultaneously.For the advantage reducing oil water interfacial tension and improve sweep efficiency two aspect comprehensively can be played during the displacement of reservoir oil, demonstrate such surfactant and improving the good application prospect in recovery ratio field.
Because the sandstone formation surface of oil reservoir is generally electronegative, use anion surfactant can reduce its Electrostatic Absorption on Reservoir Minerals, thus reducing the consumption of surfactant, the surfactant that therefore current oil field is used as oil displacement agent is generally anion surfactant.But most of anionic gemini surfactant synthesis step is comparatively complicated, and yield is low, this causes difficulty for it enters displacement of reservoir oil application on a large scale.For realizing its industrial applications, the product that raw material is easy to get, yield is higher, synthesis condition is suitable just must be synthesized.
Summary of the invention
The object of the invention is to provide a kind of anionic gemini surfactant and preparation method thereof.
For achieving the above object, the present invention implements according to following technical scheme:
A kind of anionic gemini surfactant, is made up of the component of following weight portion:
Further, described alkali compounds is NaOH or potassium hydroxide.
As present invention further optimization scheme, described phase transfer catalyst is cationic surfactant.
As present invention further optimization scheme, described cationic surfactant is one or more in benzyltriethylammoinium chloride, DTAC, TBAB and methyl tricapryl ammonium chloride.
A preparation method for anionic gemini surfactant, comprises the following steps:
1) 10 parts of fatty alcohols, 3-6 part epoxychloropropane, 0.3-0.5 part phase transfer catalyst and 3-6 part alkali compounds are mixed, under 30-80 DEG C of condition, carry out reaction 3-5 hour, obtain product A;
2) product A and 5-10 part succinyl oxide are joined in 10-20 part oxolane and mix, reaction 10-15 hour, obtains product B;
3) carry out product B and the mixing of 3-6 part alkali compounds with ethanol washing after reaction 2-3 hour, decompression distillation removing oxolane and ethanol, obtain product crude product;
4) with ethyl alcohol recrystallization twice, vacuum drying obtains anionic gemini surfactant to constant weight.
Synthesis step: fatty alcohol and epoxychloropropane are obtained by reacting alkyl monoglycidyl ether under the condition of phase transfer catalyst, alkyl monoglycidyl ether and succinyl oxide and oxolane are total to the dicarboxylic acids that molten acquisition ester group is connected, dicarboxylic acids and alkali compounds that ester group connects carry out neutralizing rear decompress filter and isolate crude product and obtains anionic gemini surfactant crude product and dicarboxylate, crude crystalline purification acquisition anionic gemini surfactant.
Compared with prior art, add cationic surfactant in manufacturing process of the present invention, make manufacture craft simple, the reaction time is short, is easy to realize suitability for industrialized production.Gemini surface active agent provided by the invention has higher surface-active, its critical micelle concentration (CMC) will a low 2-3 order of magnitude than corresponding common anionic surfactants lauryl sodium sulfate (SDS), its temperature tolerance, salt-resistance, foaming characteristic, emulsibility are comparatively strong, and other classes of surfactant has good Synergistic ability.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described, is used for explaining the present invention in this illustrative examples of inventing and explanation, but not as a limitation of the invention.
Embodiment 1
1) 100g fatty alcohol, 30g epoxychloropropane, 3g phase transfer catalyst and 30g NaOH are mixed, under 30 DEG C of conditions, carry out reaction 3 hours, obtain product A;
2) product A and 50g succinyl oxide are joined in 100g oxolane mix, react 10 hours, obtain product B;
3) product B and the mixing of 30g alkali compounds are carried out reaction with ethanol washing after 2 hours, decompression distillation removing oxolane and ethanol, obtain product crude product;
4) with ethyl alcohol recrystallization twice, vacuum drying obtains anionic gemini surfactant to constant weight.
Embodiment 2
1) 100g fatty alcohol, 60g epoxychloropropane, 5g phase transfer catalyst and 60g potassium hydroxide are mixed, under 80 DEG C of conditions, carry out reaction 5 hours, obtain product A;
2) product A and 100g succinyl oxide are joined in 200g oxolane mix, react 15 hours, obtain product B;
3) product B and the mixing of 60g potassium hydroxide are carried out reaction with ethanol washing after 3 hours, decompression distillation removing oxolane and ethanol, obtain product crude product;
4) with ethyl alcohol recrystallization twice, vacuum drying obtains anionic gemini surfactant to constant weight.
Embodiment 3
1) 100g fatty alcohol, 50g epoxychloropropane, 4g phase transfer catalyst and 50g potassium hydroxide are mixed, under 60 DEG C of conditions, carry out reaction 4 hours, obtain product A;
2) product A and 80g succinyl oxide are joined in 170g oxolane mix, react 12 hours, obtain product B;
3) product B and the mixing of 50g potassium hydroxide are carried out reaction with ethanol washing after 2.5 hours, decompression distillation removing oxolane and ethanol, obtain product crude product;
4) with ethyl alcohol recrystallization twice, vacuum drying obtains anionic gemini surfactant to constant weight.
Technical scheme of the present invention is not limited to the restriction of above-mentioned specific embodiment, the technology distortion that every technical scheme according to the present invention is made, and all falls within protection scope of the present invention.
Claims (5)
1. an anionic gemini surfactant, is characterized in that, is made up of the component of following weight portion:
2. anionic gemini surfactant according to claim 1, is characterized in that: described alkali compounds is NaOH or potassium hydroxide.
3. anionic gemini surfactant according to claim 1, is characterized in that: described phase transfer catalyst is cationic surfactant.
4. anionic gemini surfactant according to claim 2, is characterized in that: described cationic surfactant is one or more in benzyltriethylammoinium chloride, DTAC, TBAB and methyl tricapryl ammonium chloride.
5. the preparation method of a kind of anionic gemini surfactant as claimed in claim 1, is characterized in that, comprise the following steps:
1) 10 parts of fatty alcohols, 3-6 part epoxychloropropane, 0.3-0.5 part phase transfer catalyst and 3-6 part alkali compounds are mixed, under 30-80 DEG C of condition, carry out reaction 3-5 hour, obtain product A;
2) product A and 5-10 part succinyl oxide are joined in 10-20 part oxolane and mix, reaction 10-15 hour, obtains product B;
3) carry out product B and the mixing of 3-6 part alkali compounds with ethanol washing after reaction 2-3 hour, decompression distillation removing oxolane and ethanol, obtain product crude product;
4) with ethyl alcohol recrystallization twice, vacuum drying obtains anionic gemini surfactant to constant weight.
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| CN201510687619.9A CN105396504A (en) | 2015-10-21 | 2015-10-21 | Anionic gemini surfactant and preparation method thereof |
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| CN201510687619.9A CN105396504A (en) | 2015-10-21 | 2015-10-21 | Anionic gemini surfactant and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN108929238A (en) * | 2018-07-16 | 2018-12-04 | 福州大学 | A kind of Gemini surface active and preparation method thereof containing rigid radical |
| CN114213649A (en) * | 2021-12-30 | 2022-03-22 | 艾茵化学(深圳)有限公司 | Cardanol polyoxyethylene ether succinate and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6204297B1 (en) * | 1996-11-26 | 2001-03-20 | Rhodia Inc. | Nonionic gemini surfactants |
| CN102029123A (en) * | 2010-11-02 | 2011-04-27 | 中国海洋石油总公司 | Gemini surfactant and preparation method thereof |
-
2015
- 2015-10-21 CN CN201510687619.9A patent/CN105396504A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6204297B1 (en) * | 1996-11-26 | 2001-03-20 | Rhodia Inc. | Nonionic gemini surfactants |
| CN102029123A (en) * | 2010-11-02 | 2011-04-27 | 中国海洋石油总公司 | Gemini surfactant and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 张爽: "羧酸盐型双子表面活性剂合成研究进展", 《化学工程师》 * |
| 柳建新等: "二烷基乙氧基硫酸钠阴离子双子表面活性剂的合成及其表面活性", 《精细化工》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN108929238A (en) * | 2018-07-16 | 2018-12-04 | 福州大学 | A kind of Gemini surface active and preparation method thereof containing rigid radical |
| CN114213649A (en) * | 2021-12-30 | 2022-03-22 | 艾茵化学(深圳)有限公司 | Cardanol polyoxyethylene ether succinate and preparation method thereof |
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