CN102319549A - Preparation method of acetal type dicationic surfactant - Google Patents
Preparation method of acetal type dicationic surfactant Download PDFInfo
- Publication number
- CN102319549A CN102319549A CN201110188820A CN201110188820A CN102319549A CN 102319549 A CN102319549 A CN 102319549A CN 201110188820 A CN201110188820 A CN 201110188820A CN 201110188820 A CN201110188820 A CN 201110188820A CN 102319549 A CN102319549 A CN 102319549A
- Authority
- CN
- China
- Prior art keywords
- surfactant
- preparation
- acetal
- product
- dioxolane
- 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.)
- Pending
Links
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention provides a 1,3-dioxacyclopentane acetal type dicationic surfactant and a preparation method thereof. The preparation method comprises the following preparation steps: enabling n-capric aldehyde and epoxy bromopropane to react so as to get 1,3-dioxacyclopentane acetal, further reacting with benzimidazole and enabling an obtained product to react with dibromoalkane in acetonitrile so as to prepare a product. A 1,3-dioxacyclopentane acetal group I s introduced into the molecular structure of the surfactant, as the acetal group is easy to decompose, the surfactant is an environment-friendly surfactant. The raw materials used in the preparation method are easy to get, the reaction conditions are mild, the operation is simple and the method is easy for realization of industrialization.
Description
Technical field
The present invention relates to surfactant, particularly a kind of acetal type dication surfactant specifically is a kind of 1, the preparation method of 3-dioxolane acetal type dication surfactant.
Background technology
Surfactant is one type of fine chemicals that is widely used in fields such as industry, agricultural, medicine, oil recovery, printing and dyeing, and along with the development of surfactant, Gemini surface active agent is just progressing into people's the visual field with its particular structure and good performance.Research shows that Gemini surface active agent has the capillary ability of stronger reduction, and its ratio of the CMC traditional surfactant is hanged down the 1-2 one magnitude.The acetal type surfactant is the focus of present this area research; Compare with conventional surfactant; The acetal type surfactant not only the chemistry and biological degradability very big improvement has all been arranged; And surface-active improves, and is one type of novel environmental friendliness chemicals, is a direction of " environmental friendliness " surfactant development from now on.From the research situation of recent years, with Shuangzi functional group with can decompose functional groups very few with the bibliographical information of the decomposed Gemini surface active agent in a part.The decomposed Gemini surface active agent of report mainly is surfactant (J Colloid Interface Sci.2007,312 (2): 444-452) that contain ester group at present.And ester group is under alkali condition, to decompose; Acetal radical is under acid condition, to decompose; And acetal radical more be prone to decompose than ester group, and therefore the research to the acetal Gemini surface active agent will have application prospect and value widely in fields such as industry, agricultural, medicine, oil recovery, printing and dyeing.
Summary of the invention
It is a kind of 1 that the object of the invention is to provide, 3-dioxolane acetal type dication surfactant and preparation method thereof.
Provided by the invention a kind of 1,3-dioxolane acetal type dication surfactant, its molecular structure is:
Its preparation method comprises the steps:
(1) makes 1,3-dioxolane acetal with epoxy bromopropane and n-Heptaldehyde reaction;
(2) benzimidazole, TBAB, NaOH solution and toluene are added in the reactor, reflux 1h drips 1; 3-dioxolane acetal continues backflow 18-36h, cooling; The washing of reactant liquor adding distil water separates, and organic facies is through drying; Remove desolvate faint yellow transparent liquid, use column chromatography intermediate product; Wherein: the NaOH liquid quality fraction is 10-20%, 1, and the mol ratio of 3-dioxolane acetal and benzimidazole, NaOH is 1: 0.8-1.5: 2-6;
(3) intermediate product and dibrominated alkane, in acetonitrile solution, reflux 12-36h removes and desolvates, and gets crude product, adds petroleum ether, and suction filtration gets product; Wherein: the mol ratio of intermediate product and dibrominated alkane is 1: 0.5-1.5.
Described dibrominated alkane is 1,4-dibromobutane, 1, pentamethylene bromide, 1,6-dibromo-hexane, 1,7-dibromo-heptane, 1,8-two bromooctanes, 1,9-two bromononanes or 1,10-dibromo-decane.
Technique scheme has following advantage:
(1) dication surfactant provided by the invention contains two acetal groups and two cation groups simultaneously; Novel structure has the capillary ability of stronger reduction, introduces 1 in the molecule; 3-dioxolane acetal groups is eco-friendly surfactant.
(2) research shows that the Gemini surface active agent that is synthesized has the capillary ability of stronger reduction; Its ratio of the CMC traditional surfactant is hanged down the 1-2 one magnitude, has purposes widely in fields such as industry, agricultural, medicine, oil recovery, printing and dyeing.
(3) raw materials used being easy to get among the preparation method of dication surfactant provided by the invention, reaction condition is gentle, and is simple to operate, is prone to realize the industrialization of product.
The specific embodiment
Embodiment 1
Step 1:
In 100mL four neck round-bottomed flasks, add n-Heptaldehyde 4.56g (40mmol), the 40mL carbon tetrachloride, BFEE 0.5mL mixes the 10mL carbon tetrachloride in addition with 6.16g (45mmol) epoxy bromopropane, slowly splash into three neck round-bottomed flasks, drips off within an hour; Temperature keeps 55 ℃, refluxes 8 hours.The back cooling is accomplished in reaction, adds 100mL distilled water, and reactant liquor is with 100mL extracted with diethyl ether three times, and the separation organic facies is with anhydrous MgSO
4Drying is removed solvent, gets the thick product of yellowish-brown, and again with column chromatography for separation, flowing phase is benzinum: ethyl acetate (25: 1), product are colourless liquid, and productive rate is 43.3%.
Step 2:
In 100mL four neck round-bottomed flasks, add benzimidazole 1.30g (0.011mol) successively, TBAB 0.1g, NaOH1.6g (0.04mol), distilled water 10mL, toluene 30mL drips acetal 2.51g in heptan (0.01mol) behind the reflux 1h, continue backflow 24h.After reaction finishes, cooling, reactant liquor adds 50mL distilled water washing, separates organic facies, after the drying, removes and desolvates to such an extent that bullion is faint yellow transparent liquid, and bullion uses column chromatography, and flowing phase is V (ethanol): V (ethyl acetate)=1: 25, productive rate 48.1%.
Step 3:
In 100mL four neck round-bottomed flasks, add step 2 product 2.88g (0.01mol) successively respectively, 1,10-dibromo-decane 1.50g (0.005mol), 30ml acetonitrile, reflux 24h.After reaction finishes, remove and desolvate, get crude product, add petroleum ether, suction filtration gets product, productive rate 42.8%.
Product (n=10 in the compound structure), product appearance: white solid,
1HNMR (CDCl
3), δ ppm:0.85 (t, 6H), 1.16-1.53 (m, 32H), 1.81-2.06 (d, 4H), 3.40 (t, 4H), 3.39-4.87 (m, 8H), 5.01-5.10 (m, 4H), 7.64-7.92 (m, 10H) .IR (KBr), v/cm
-1: 3446,2927,2854,1614,1562,1286,1217,1137,769.
Embodiment 2
Step 1: with embodiment 1;
Step 2: with embodiment 1;
Step 3: in 100mL four neck round-bottomed flasks, add step 2 product 2.88g (0.01mol) successively respectively, 1,6-dibromo-hexane 1.22g (0.005mol), 30ml acetonitrile, reflux 24h.After reaction finishes, remove and desolvate, get crude product, add petroleum ether, suction filtration gets product, productive rate 46.5%.
Product (n=6 in the compound structure), product appearance: white solid,
1HNMR (CDCl
3), δ ppm:0.85 (t, 6H), 1.23-1.85 (m, 20H), 1.87-2.10 (d, 8H), 341 (t, 4H), 3.88-4.71 (m, 8H), 4.83-5.09 (m, 4H), 7.64-7.93 (m, 10H) .IR (KBr), v/cm
-1: 3448,2933,2854,1631,1560,1191,1134,769.
Embodiment 3
Step 1: with embodiment 1;
Step 2: with embodiment 1;
Step 3: in 100mL four neck round-bottomed flasks, add step 2 product 2.88g (0.01mol) successively respectively, 1,4-dibromobutane 1.08g (0.005mol), 30ml acetonitrile, reflux 24h.After reaction finishes, remove and desolvate, get crude product, add petroleum ether, suction filtration gets product, productive rate 37.2%.
Product (n=4 in the compound structure), product appearance: white solid,
1HNMR (CDCl
3), δ ppm:0.83 (t, 6H), 1.14-1.51 (m, 20H), 2.01-241 (d, 4H), 3.48 (t, 4H), 3.86-4.82 (m, 8H), 4.94-5.02 (m, 4H), 7.64-8.05 (m, 10H) .IR (KBr), v/cm
-1: 3434,2950,2856,1620,1564,1280,1217,1137,769.
Claims (3)
1. 3-dioxolane acetal type dication surfactant is characterized in that molecular structure is:
2. as claimed in claim 1 a kind of 1, the preparation method of 3-dioxolane acetal type dication surfactant is characterized in that, comprises the steps:
(1) makes 1,3-dioxolane acetal with epoxy bromopropane and n-Heptaldehyde reaction;
(2) benzimidazole, TBAB, NaOH solution and toluene are added in the reactor, reflux 1h drips 1; 3-dioxolane acetal continues backflow 18-36h, cooling; The washing of reactant liquor adding distil water separates, and organic facies is through drying; Remove desolvate faint yellow transparent liquid, use column chromatography intermediate product; Wherein: the NaOH liquid quality fraction is 10-20%, 1, and the mol ratio of 3-dioxolane acetal and benzimidazole, NaOH is 1: 0.8-1.5: 2-6;
(3) intermediate product and dibrominated alkane, in acetonitrile solution, reflux 12-36h removes and desolvates, and gets crude product, adds petroleum ether, and suction filtration gets product; Wherein: the mol ratio of intermediate product and dibrominated alkane is 1: 0.5-1.5.
3. as claimed in claim 1 a kind of 1, the preparation method of 3-dioxolane acetal type dication surfactant is characterized in that; Described dibrominated alkane is 1,4-dibromobutane, 1, pentamethylene bromide, 1; 6-dibromo-hexane, 1,7-dibromo-heptane, 1,8-two bromooctanes, 1; 9-two bromononanes or 1, the 10-dibromo-decane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110188820A CN102319549A (en) | 2011-07-07 | 2011-07-07 | Preparation method of acetal type dicationic surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110188820A CN102319549A (en) | 2011-07-07 | 2011-07-07 | Preparation method of acetal type dicationic surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102319549A true CN102319549A (en) | 2012-01-18 |
Family
ID=45447455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110188820A Pending CN102319549A (en) | 2011-07-07 | 2011-07-07 | Preparation method of acetal type dicationic surfactant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102319549A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103240033A (en) * | 2013-04-29 | 2013-08-14 | 湖南科技学院 | Easily separated degradable sodium carboxylate surfactant and preparation and performance thereof |
| CN105727828A (en) * | 2016-03-03 | 2016-07-06 | 江南大学 | Cationic gemini surfactants and preparation method thereof |
| CN106365221A (en) * | 2016-11-09 | 2017-02-01 | 烟台史密得机电设备制造有限公司 | Adamantine mono-quaternary ammonium salt cationic three compound combination flooding produced water oil remover |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0568863A (en) * | 1991-09-10 | 1993-03-23 | Japan Tobacco Inc | Nonionic surfactant consisting of oxazolidine derivative |
| CN101185867A (en) * | 2006-11-17 | 2008-05-28 | 天津科技大学 | Gemini quaternary ammonium salt cationic surfactant and preparation method thereof |
| CN101711960A (en) * | 2009-11-19 | 2010-05-26 | 山西大学 | Method for preparing 1,3-dioxane acetal type dianion surface active agent |
-
2011
- 2011-07-07 CN CN201110188820A patent/CN102319549A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0568863A (en) * | 1991-09-10 | 1993-03-23 | Japan Tobacco Inc | Nonionic surfactant consisting of oxazolidine derivative |
| CN101185867A (en) * | 2006-11-17 | 2008-05-28 | 天津科技大学 | Gemini quaternary ammonium salt cationic surfactant and preparation method thereof |
| CN101711960A (en) * | 2009-11-19 | 2010-05-26 | 山西大学 | Method for preparing 1,3-dioxane acetal type dianion surface active agent |
Non-Patent Citations (1)
| Title |
|---|
| 瞿文杰等: "苯并咪唑阳离子缩醛型表面活性剂的合成及性能", 《精细化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103240033A (en) * | 2013-04-29 | 2013-08-14 | 湖南科技学院 | Easily separated degradable sodium carboxylate surfactant and preparation and performance thereof |
| CN103240033B (en) * | 2013-04-29 | 2015-11-25 | 湖南科技学院 | Easily separated degradable sodium carboxylate surfactant and preparation thereof and performance |
| CN105727828A (en) * | 2016-03-03 | 2016-07-06 | 江南大学 | Cationic gemini surfactants and preparation method thereof |
| CN106365221A (en) * | 2016-11-09 | 2017-02-01 | 烟台史密得机电设备制造有限公司 | Adamantine mono-quaternary ammonium salt cationic three compound combination flooding produced water oil remover |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105037363B (en) | A kind of entecavir compound prepared novel synthesis | |
| CN102127092A (en) | Preparation of Everolimus | |
| CN107245045A (en) | A kind of preparation method for the ground ostelin that ends | |
| CN103524403A (en) | Preparation method of doxylamine succinate | |
| CN106365986A (en) | Compounds and preparation methods thereof, and uses of compounds in synthesis of brivaracetam | |
| CN102319549A (en) | Preparation method of acetal type dicationic surfactant | |
| CN104177331B (en) | The preparation method of bilastine | |
| CN104774174B (en) | A kind of method of asymmetric syntheses S carbinoxamines | |
| CN105085168B (en) | Wheat midge sex pheromone precursor and wheat midge sex pheromone | |
| CN101973932A (en) | Preparation method of bisacodyl | |
| CN100460378C (en) | 2,7-dimethyl-octa-2,4,6-trienedial preparation method | |
| CN107857702A (en) | A kind of preparation method of bilastine intermediate | |
| CN104710347B (en) | (R) synthetic method of the tetrahydrochysene piperidines of 1 benzyl, 3 methyl 1,2,3,6 | |
| CN101219938B (en) | Guaiacol synthesizing method | |
| CN102249962B (en) | Preparation method of 1,1-disulfur-1-olefin | |
| CN101781205B (en) | Method for synthesizing substitutional crylic acid phenyl ester | |
| CN102212060A (en) | Method for preparing lafutidine by virtue of aminolysis | |
| CN101580714B (en) | Preparation method of dicyclic hexane liquid crystal monomer | |
| CN106631911A (en) | Method for synthesizing cis-tritosylate | |
| CN1865234A (en) | Capsicine chemical synthesis and purification method | |
| CN101735241A (en) | Prasugrel intermediate and preparation method thereof | |
| CN106967014A (en) | A kind of synthetic method of tea geometrid sex pheromone | |
| CN102140071A (en) | Method for synthesizing 2-(4-tert-butyl-phenyl) malonic mononitrile (2-methoxyl) ethyl ester | |
| CN102516233A (en) | Novel method for producing voriconazole | |
| CN102212061A (en) | Reducing preparation method for lafutidine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120118 |
|
| WD01 | Invention patent application deemed withdrawn after publication |