CN103611471B - One class contains carboxylate surface active agent of aromatic group and preparation method thereof - Google Patents
One class contains carboxylate surface active agent of aromatic group and preparation method thereof Download PDFInfo
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- CN103611471B CN103611471B CN201310664201.7A CN201310664201A CN103611471B CN 103611471 B CN103611471 B CN 103611471B CN 201310664201 A CN201310664201 A CN 201310664201A CN 103611471 B CN103611471 B CN 103611471B
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Abstract
The present invention relates to a class and contain carboxylate surface active agent of aromatic group and preparation method thereof, its molecular structure is as follows:
r=C
8h
17, C
10h
21, C
12h
25or C
14h
29ar=any aryl groups that contain no more than3aryl groups wherein R is straight chained alkyl C
8h
17, C
10h
21, C
12h
25or C
14h
29in any one; Ar represents that molecule includes the aromatic group that aromatic ring number is no more than 3.The preparation of this surfactant mainly comprises the synthesis of 2-bromo acid esters, the synthesis of 2-aryloxy alkyl ester and saponification three step.This surfactant is due to containing aromatic group, can be used as and there is surface-active fluorescence probe for detecting the microscopic appearance of the sight aggregation that is situated between, also can be used in surfactant compound system, have important application in fields such as washing agent, medicinal slow release agent, cosmetic skincare products.
Description
Technical field
The present invention relates to a class and contain carboxylate surface active agent of aromatic group and preparation method thereof.This surfactant has good water-soluble, can be used for, in surfactant compound system and fluorescence analysis method, belonging to surfactant scientific domain.
Background technology
Surfactant molecule has amphiphilic structure, can form multiple gathering pattern in aqueous.The performance seeing aggregation that is situated between often determines surfactant system macroscopic property, thus has a wide range of applications in multiple field.And surfactant is situated between, and to see the form of aggregation and character and molecular structure closely related.The research of Surfactant structure-performance is the focus of surfactant scientific research always.The change of any structural element, all likely affects the self-organizing performance of surfactant, and then has influence on form and the character of aggregation.
What surfactant formed the process dependence of aggregation is intermolecular interaction force, and modal is the electrostatic interaction between head base or the hydrophobic interaction between dipole effect and hydrophobic chain.In fact, the π-π that intermolecular interaction also comprises between hydrogen bond, aromatic ring acts on.If autotelic introducing can produce the functional group of above-mentioned effect in the molecular structure of surfactant, just likely rely on the interaction between different kinds of molecules, construct the surfactant aggregates with novel structure.The present invention proposes a class and contain structure of the surfactant of aromatic group and preparation method thereof, be convenient for people to study the relation containing between the self-organizing behavior of aromatic group surfactant and molecular structure, be also conducive to deepening people to the understanding of interaction of molecules rule.
Summary of the invention
The present invention relates to a class and contain carboxylate surface active agent of aromatic group and preparation method thereof.With aliphatic acid, phenol etc. as predominant starting material, synthesize the carboxylate surface active agent of a class containing aromatic group.
Containing the carboxylate surface active agent of aromatic group, structural formula is as follows:
R=C
8H
17，C
10H
21，C
12H
25Or C
14H
29
Ar=any aryl groups that contain no more than3aryl groups
A kind ofly prepare the described method containing aromatic group carboxylate surface active agent, with aliphatic acid and thionyl chloride or oxalyl chloride is obtained by reacting acyl chlorides, the acyl chlorides obtained is obtained by reacting 2-bromacyl chloride with bromine again, in 2-bromacyl chloride, drip methyl alcohol obtain 2-bromo acid esters, 2-bromo acid esters and phenol are obtained by reacting 2-aryloxy alkyl ester, and namely 2-aryloxy alkyl ester obtains the carboxylate surface active agent containing aromatic group through saponification.Concrete reaction equation is as follows:
Synthetic route containing the carboxylate surface active agent of aromatic group:
In the reaction of synthesis 2-bromo acid esters, with aliphatic acid and thionyl chloride or oxalyl chloride is obtained by reacting acyl chlorides, acyl chlorides is obtained by reacting 2-bromacyl chloride with simple substance bromine again, methyl alcohol is dripped or ethanol obtains 2-bromo acid esters in 2-bromacyl chloride, wherein the mol ratio of aliphatic acid and chloride reagent is 1:1 ~ 5, the mol ratio of aliphatic acid and bromine is 1:1 ~ 10, and the mol ratio of aliphatic acid and alcohol is 1:1 ~ 20.The crude product obtained, through decompression distillation, is collected the cut that boiling point is 195 DEG C (5mmHg), is obtained water white liquid.
In the reaction of synthesis 2-aryloxy alkyl ester, the mol ratio of 2-bromo acid esters and phenol is 1:1 ~ 10, and reaction condition is react 8 ~ 20 hours at 90 DEG C, and solvent for use is DMF, and crude product ester is through silica gel column chromatogram separating purification.
Contain in the reaction of the carboxylate surface active agent of aromatic group in synthesis, the mol ratio of 2-aryloxy alkyl ester and NaOH is 1:1 ~ 5, reaction condition be at 80 DEG C react 8 ~ 20 hours, solvent for use be any one solvent such as absolute methanol, absolute ethyl alcohol or isopropyl alcohol or they with arbitrary proportion mixing mixed solvent.
The present invention obtains following effect:
1. the present invention mainly contains the carboxylate surface active agent of aromatic group through three-step reaction synthesis, explores concrete reaction condition and achieves good productive rate.
2. the carboxylate surface active agent containing aromatic group of synthesis, its critical micelle concentration cmc can reach 3.24 × 10
-3mol/L
-1, show stronger ability of aggregation.
Accompanying drawing explanation
Fig. 1 is the nuclear magnetic resonance of embodiment target product
1hNMR spectrogram, solvent for use is CD
3oD.
Fig. 2 is the surface tension curve of embodiment target product, records in the alkali lye of pH12.
Detailed description of the invention
The present embodiment is for illustrating and the protection domain of unrestricted this patent.
Embodiment 1
Containing the synthesis of aromatic group surfactant 2-phenoxy group sodium laurate, its synthetic route is as follows:
(1) preparation of 2-bromolauric acid methyl esters
In three-necked bottle, add laurate (130.2g, 0.65mol), load onto reflux condensing tube, device for absorbing tail gas and constant pressure funnel.First slowly will bathe temperature rise to 50 DEG C, and solid be melted, then slowly drips thionyl chloride (105.2g, 0.81mol).After reaction terminates, add 0.5g iodine as catalyst, temperature is risen to 90 DEG C, slowly drip through the dried bromine (121.1g, 0.758mol) of the concentrated sulfuric acid, about 5h drips off, and continues reaction 3h after dripping.Temperature is down to 55 DEG C, and stir lower dropping 100ml absolute methanol, reflux after adding 4h again.Reaction is cooled to room temperature, washes away bromine residual in crude product with saturated sodium sulfite solution, leaves standstill, point water-yielding stratum, organic layer washed with water, and with anhydrous magnesium sulfate drying, collect the cut that boiling point is 195 DEG C (5mmHg), obtain water white liquid, productive rate 78.3%.
The preparation of (, 2) 2-phenoxy group methyl dodecanoate
K is added in eggplant-shape bottle
2cO
3(30g, 0.217mol) and appropriate DMF, N
2protection, starts magnetic stirring apparatus, after stirring 0.5h, adds phenol (10.2g, 0.108mol), is warming up to 60 DEG C, then add 2-bromolauric acid methyl esters (20.0g, 0.068mol), is warming up to 80 DEG C and continues reaction 6h after 1h.After question response liquid is down to room temperature, under agitation add suitable quantity of water to reactant liquor, with appropriate petroleum ether extraction three times, merge organic layer, after organic layer washed with water three times, rotary evaporation goes out whole benzinum and part water, and the thick product silica gel column chromatography obtained is separated and obtains sterling, productive rate 75.1%.
(3) synthesis of 2-phenoxy group sodium laurate
2-phenoxy group methyl dodecanoate (14.3g is added in eggplant-shape bottle, 0.047mol), NaOH (2.06g, 0.051mol) and appropriate absolute ethyl alcohol, 70 DEG C of magnetic agitation backflow 12h, question response liquid is cooled to room temperature, revolve and steam except desolventizing, solids washed with acetone 4 ~ 6 times, vacuum drying, obtain 2-phenoxy group sodium laurate, productive rate 92.5%.
Embodiment 2
The capillary mensuration of 2-phenoxy group sodium laurate
2-phenoxy group sodium laurate is dissolved in the alkali lye of pH12, prepares the surfactant solution of serial variable concentrations, at 25 DEG C, then measure the equilibrium surface tension of this surfactant.
Claims (6)
1. a class is containing the carboxylate surface active agent of aromatic group, and its molecular structure is as follows:
Wherein R is straight chained alkyl C
8h
17, C
10h
21, C
12h
25or C
14h
29in any one; Ar represents that molecule includes the aromatic group that aromatic ring number is no more than 3.
2. a class according to claim 1 is containing the carboxylate surface active agent of aromatic group, it is characterized in that, such carboxylate surface active agent containing aromatic group has Krafft point water-soluble and lower preferably.
3. a class according to claim 1 is containing the carboxylate surface active agent of aromatic group, it is characterized in that, such ability of aggregation containing the carboxylate surface active agent of aromatic group is comparatively strong, and its critical micelle concentration is lower than 5mmolL
-1.
4. prepare a method for the carboxylate surface active agent containing aromatic group as claimed in claim 1, preparation process mainly comprises the synthesis of 2-bromo acid esters, the synthesis of 2-aryloxy alkyl ester and saponification three step.Its synthetic route is as follows:
5. the preparation method containing aromatic group surfactant according to claim 4, it is characterized in that, wherein R is straight chained alkyl C
8h
17, C
10h
21, C
12h
25or C
14h
29in any one; Ar represents that molecule includes the aromatic group that aromatic ring number is no more than 3.
6. the preparation method containing aromatic group surfactant according to claim 4, is characterized in that, the purification process of 2-aryloxy alkyl ester is that silica gel column chromatography is separated.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106179111B (en) * | 2016-07-16 | 2018-08-14 | 江南大学 | A kind of viscoelastic solution formed by carboxylate anion's surfactant and two polyquaterniums |
| CN106512848B (en) * | 2016-09-30 | 2018-07-17 | 武汉工程大学 | A kind of cyclic quaternary ammonium salts Gemini surface active agent and preparation method thereof |
| CN107088386B (en) * | 2017-06-14 | 2019-06-07 | 江南大学 | A kind of Long carbon chain carboxylate surface active agent of high-dissolvability and its viscoelastic solution of formation |
| CN110585991B (en) * | 2019-09-23 | 2020-10-09 | 江南大学 | Two-phase transition emulsion with stable carboxylate surfactant and nanoparticles |
| CN111054263B (en) * | 2019-12-23 | 2021-07-23 | 万华化学集团股份有限公司 | Fluorescent surfactant and preparation method thereof |
| CN111635390A (en) * | 2020-06-30 | 2020-09-08 | 江南大学 | Low-foam alpha-tocopherol surfactant and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4867972A (en) * | 1985-05-06 | 1989-09-19 | Rhone-Poulenc Specialites Chimiques | Novel surface-active compositions containing polydicarboxylic acid polymer and surfactant |
| CN1730144A (en) * | 2004-08-04 | 2006-02-08 | 大庆高新区鑫诺精细化工有限公司 | Carboxylate surface active agent, its formula system and its application in tertiary oil extraction |
| CN101723822A (en) * | 2008-10-29 | 2010-06-09 | 天津工业大学 | Polymerizable negative ion surfactant and preparing method thereof |
-
2013
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4867972A (en) * | 1985-05-06 | 1989-09-19 | Rhone-Poulenc Specialites Chimiques | Novel surface-active compositions containing polydicarboxylic acid polymer and surfactant |
| CN1730144A (en) * | 2004-08-04 | 2006-02-08 | 大庆高新区鑫诺精细化工有限公司 | Carboxylate surface active agent, its formula system and its application in tertiary oil extraction |
| CN101723822A (en) * | 2008-10-29 | 2010-06-09 | 天津工业大学 | Polymerizable negative ion surfactant and preparing method thereof |
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