CN102728272A - Cashew-based quaternary ammonium salt cationic surfactant and its preparation method - Google Patents
Cashew-based quaternary ammonium salt cationic surfactant and its preparation method Download PDFInfo
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- CN102728272A CN102728272A CN2012102125144A CN201210212514A CN102728272A CN 102728272 A CN102728272 A CN 102728272A CN 2012102125144 A CN2012102125144 A CN 2012102125144A CN 201210212514 A CN201210212514 A CN 201210212514A CN 102728272 A CN102728272 A CN 102728272A
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Abstract
The invention belongs to the technical field of surfactant, and discloses a cashew-based quaternary ammonium salt cationic surfactant and its preparation method. The general formula is shown in the specification, wherein R1, R2 and R3 are C1-C4 alkyl group, and X is halogen. 3-meta-pentadecyl phenol, formaldehyde, secondary amine are reacted to generate an intermediate Mannich base, the intermediate is reacted with halogenated alkane to generate quaternary ammonium salt cationic surfactant. The prepared cationic surfactant molecules possesses a hydrophobic alkyl chain connected with benzene ring, a quaternary ammonium cation and hydrophilic phenolic hydroxyl group. According to the invention, the inherent performance of the quaternary ammonium compound is kept, and the hydrophilic part in the compound molecules can increase solubility of the surfactant in water.
Description
Technical field
The invention belongs to technical field of surfactant, particularly a kind of cashew nut based quaternary ammonium salt cationic surfactant and preparation method thereof.
Background technology
Surfactant (or interfacial agent) is the material that can significantly reduce surface tension of liquid or two-phase interface tension force.Have surface-active material and be called amphiphile, amphiphilic molecule, promptly contain hydrophilic in the molecule and two parts of oleophylic, oleophilic moiety is generally C
7-C
21Long alkyl chain, hydrophilic segment is generally water soluble group.In general; Hydrophilic group makes molecule introduce water, and lipophilic group makes the molecule leaving water introduce oil, and these two kinds of groups lay respectively at the two ends of molecule; Cause the asymmetric of molecule; Therefore surfactant molecule is the molecule of a kind of not only hydrophilic but also oleophylic, has and anion surfactant (fatty acid soaps) opposite configuration, to such an extent as to it also is called as the commentaries on classics saponification.
Traditional surfactant is raw material mostly with petrochemicals, and still along with the exhaustive exploitation of oil, coal, the shortage of the energy, raw material will become the bottleneck of surfactant industrial development.On the other hand, traditional oil and chemical industry further worsen environment, three wastes difficult treatment.In addition, surfactant is applied in medicine, food, cosmetics and the various personal cleanliness's articles for use more and more, thus, and the security of the also increasing concern surfactant of people.So; From the being easy to get property of resource, the aspects such as sustainability of the security of environment and human body and compatibility, industry development are considered; Research and development is raw material with the natural reproducible resource, and preparation low toxicity, surfactant renewable and good biodegradability properties are very necessary.
By the alkene of Petroleum refining is that the nonyl phenol of feedstock production is one type of important source material and intermediate of producing surfactant, can prepare APEO and APEO derivatives class surfactant, quaternary ammonium salt cationic surfactant and sulfonic acid type surfactant etc. by nonyl phenol.But nonyl phenol has the endocrine disturbing effect for human body, but is a kind of carcinogenic substance, and a series of surfactants that made by nonyl phenol exist seriously polluted, defective such as biological degradability is poor, and security performance is low.Simultaneously in China, the output of nonyl phenol is difficult to satisfy domestic demand always, relies on import for a long time, and causing with the nonyl phenol is that a series of surfactant production costs of raw material are higher.
With pentadecyl phenol between the 3-of refining anacardol preparation is raw material; Problem to the existence of nonyl phenol series of surfactants; Expectation is carried out the synthetic and technical study of surfactant with pentadecyl phenol between 3-as the substitute of nonyl phenol; Raw material derives from the natural biomass resource at all, has advantages such as renewable, low-cost, environmental protection.As the substitute research of nonyl phenol, can solve the predicament that current nonyl phenol series of surfactants is produced, and be the development and application developing approach of new material.As the synthetic quaternary ammonium salt cationic surfactant of raw material, outside in the past starch base class, cellulose family, aminosugars control surface activating agent field, open up new research field and new research approach with natural biomass phenol, have great importance.
Summary of the invention
The object of the present invention is to provide a kind of cashew nut based quaternary ammonium salt cationic surfactant and preparation method thereof.
For realizing above-mentioned purpose, the technical scheme that the present invention takes is following:
A kind of cashew nut based quaternary ammonium salt cationic surfactant, its general formula is:
A kind of preparation method of cashew nut based quaternary ammonium salt cationic surfactant: pentadecyl phenol, 37% (mass percent) formalin, secondary amine between 3-are joined in the solvent; Earlier at 10 ~ 40 ℃ of following Mannich reaction 0.5 ~ 4 h; Back flow reaction 1 ~ 4 h obtains intermediate Mannich alkali after the separation purification again; Mannich alkali and halogenated alkane are joined in the solvent, alkylated reaction 12 ~ 48 h under 65 ~ 85 ℃ of counterflow conditions, separation obtains the cashew nut based quaternary ammonium salt cationic surfactant after purifying; The solvent of said Mannich reaction and alkylated reaction is methyl alcohol, ethanol, 1-propyl alcohol, 1-butanols or isopropyl alcohol.
The general formula of said secondary amine is NHR
1R
2, the general formula of said halogenated alkane is R
3X.
The mol ratio of pentadecyl phenol, formaldehyde and secondary amine is 1 ︰ (2.5 ~ 5.0) ︰ (2.5 ~ 5.0) between 3-.
The mol ratio of Mannich alkali and halogenated alkane is 1 ︰ (3 ~ 9).
During the Mannich reaction, the consumption of solvent guarantees that the concentration of pentadecyl phenol between 3-is controlled at 0.2 ~ 1mol/L; During alkylated reaction, the consumption of solvent guarantees that the concentration of Mannich alkali is controlled at 0.2 ~ 1mol/L.
The preparation process of quaternary cationics of the present invention, shown in following reaction equation:
In the superincumbent reaction equation, after pentadecyl phenol, formaldehyde, secondary amine react between 3-, generate intermediate Mannich alkali, this intermediate reacts with halogenated alkane again, generates quaternary cationics.
Cationic surfactant of the present invention is that raw material prepares with pentadecyl phenol, formaldehyde, secondary amine and halogenated alkane between 3-; Cost of material is lower; Through having a hydrophobic alkyl chain that links to each other with phenyl ring, a quaternary ammonium salt cationic and hydrophilic phenolic hydroxyl group in the cationic surfactant molecule that Mannich reacts and alkylated reaction is prepared; The present invention through the hydrophilic segment in this compound molecule, can improve its solubility in water when keeping the quaternary ammonium compound proper property.
Description of drawings
Fig. 1 is the infrared spectrum sketch map of cashew nut based quaternary ammonium salt cationic surfactant among the embodiment 1.
Fig. 2 is the relation curve sketch map of the surface tension and the concentration of cashew nut based quaternary ammonium salt cationic surfactant among the embodiment 1.
The specific embodiment
In four-hole boiling flask, add pentadecyl phenol, the diethylamine of 18.5 g (0.25 mol) and the ethanol of 500 mL between the 3-of 30.4 g (0.1 mol); Stir; And drip 20.3 g (0.25 mol), 37% formalin; After dropwising, 10 ℃ are reacted 0.5 h, back flow reaction 1 h down.Tell while hot organic facies and the decompression steam solvent, obtaining 6-diethylin methyl-3-pentadecyl phenol is intermediate (Mannich alkali).
In four-hole boiling flask, add intermediate (Mannich alkali), the bromoethane of 16.2 g (0.15 mol) and the ethanol of 50 mL of 19.45 g (0.05 mol), 65 ℃ of refluxed are reacted 12 h.Revolve to steam to remove and desolvate, obtain thick liquid, a large amount of Off-white solid appear in cooling slightly, use re-crystallizing in ethyl acetate, and vacuum drying, obtain the white powder crystallization and are pure cationic surfactant.
The infrared spectrum of product is seen Fig. 1.From the infrared spectrogram of Fig. 1, can see, at 3182.61 cm
-1Absworption peak is the characteristic absorption peak of hydroxyl; 2848.43 cm
-1, 2924.43cm
-1Characteristic absorption peak for the methyl methylene; 1616.38 cm
-1, 1427.09 cm
-1Skeleton shock absorbing peak for amide groups, amino and aromatic ring; 874.64 791.90,725.81 is that 1,3,6 three of phenyl ring replaces characteristic absorption peak.Can know that from above analysis main peak is able to ownership, can infer the structure of product basically, turns out to be surfactant of the present invention.
Adopt drop-volume method to measure the surface tension of product in the aqueous solution, surface tension is with as shown in Figure 2 with the relation curve sketch map of concentration.As can be seen from Figure 2, along with the increase of cashew nut based quaternary ammonium salt cationic surfactant concentration of aqueous solution, the surface tension of system reduces rapidly, and catastrophe point occurs, is critical micelle concentration cmc here.Reach after the critical micelle concentration, surface tension is tending towards definite value.The critical micelle concentration cmc that can obtain this surfactant from the catastrophe point of curve is 3.5 mmol/L, and corresponding critical surface tension is 38.13 mN/m.
Embodiment 2
In four-hole boiling flask, add pentadecyl phenol, the dimethylamine of 22.8 g (0.5 mol) and the methyl alcohol of 100 mL between the 3-of 30.4 g (0.1 mol); Stir, and drip 40.6 g (0.5 mol), 37% formalin, after dropwising; 40 ℃ are reacted 4 h, back flow reaction 4 h down.Tell while hot organic facies and at a certain temperature the decompression steam solvent, obtaining 6-dimethylamino methyl-3-pentadecyl phenol is intermediate (Mannich alkali).
In four-hole boiling flask, add intermediate (Mannich alkali), the bromoethane of 48.6 g (0.45 mol) and the methyl alcohol of 250 mL of 18.5 g (0.05 mol), 85 ℃ of refluxed are reacted 48 h.Revolve to steam to remove and desolvate, obtain thick liquid, a large amount of Off-white solid appear in cooling slightly, use re-crystallizing in ethyl acetate, and vacuum drying, obtain the white powder crystallization and are pure cationic surfactant.
Each functional group and embodiment 1 similar (figure slightly) in the infrared spectrum of embodiment 2.
Adopt drop-volume method to measure the surface tension of product in the aqueous solution, surface tension is with similar with Fig. 2 with the relation curve variation tendency of concentration.Along with the increase of cashew nut based quaternary ammonium salt cationic surfactant concentration of aqueous solution, the surface tension of system reduces rapidly, and catastrophe point occurs, is critical micelle concentration cmc here.Reach after the critical micelle concentration, surface tension is tending towards definite value.The critical micelle concentration cmc that can obtain this surfactant from the catastrophe point of curve is 2.9 mmol/L, and corresponding critical surface tension is 35.13 mN/m.
Embodiment 3
In four-hole boiling flask, add pentadecyl phenol, the diethylamine of 27.75 g (0.375 mol) and the 1-propyl alcohol of 250 mL between the 3-of 30.4 g (0.1 mol); Stir; And drip 30.4 g (0.375 mol), 37% formalin; After dropwising, 35 ℃ are reacted 1 h, back flow reaction 2 h down.Tell while hot organic facies and at a certain temperature the decompression steam solvent, obtaining 6-diethylin methyl-3-pentadecyl phenol is intermediate (Mannich alkali).
In four-hole boiling flask, add intermediate (Mannich alkali), the Celfume of 28.2 g (0.3 mol) and the isopropyl alcohol of 125mL of 19.45 g (0.05 mol), 80 ℃ of refluxed are reacted 24 h.Revolve to steam to remove and desolvate, obtain thick liquid.A large amount of Off-white solid appear in cooling slightly.Use re-crystallizing in ethyl acetate, and vacuum drying, obtain the white powder crystallization and be pure cationic surfactant.
Each functional group and embodiment 1 similar (figure slightly) in the infrared spectrum of embodiment 3.
Adopt drop-volume method to measure the surface tension of product in the aqueous solution, surface tension is with similar with Fig. 2 with the relation curve variation tendency of concentration.Along with the increase of cashew nut based quaternary ammonium salt cationic surfactant concentration of aqueous solution, the surface tension of system reduces rapidly, and catastrophe point occurs, is critical micelle concentration cmc here.Reach after the critical micelle concentration, surface tension is tending towards definite value.The critical micelle concentration cmc that can obtain this surfactant from the catastrophe point of curve is 3.1 mmol/L, and corresponding critical surface tension is 36.29 mN/m.
Embodiment 4
In four-hole boiling flask, add pentadecyl phenol, the diethylamine of 18.5 g (0.25 mol) and the 1-butanols of 100 mL between the 3-of 30.4 g (0.1 mol); Stir; And drip 30.4 g (0.375 mol), 37% formalin; After dropwising, 35 ℃ are reacted 1 h, back flow reaction 2 h down.Tell while hot organic facies and at a certain temperature the decompression steam solvent, obtaining 6-diethylin methyl-3-pentadecyl phenol is intermediate (Mannich alkali).
In four-hole boiling flask, add intermediate (Mannich alkali), the N-Propyl Bromide of 54.8 g (0.45 mol) and the 1-butanols of 100 mL of 19.45 g (0.05 mol), 80 ℃ of refluxed are reacted 12 h.Revolve to steam to remove and desolvate, obtain thick liquid.A large amount of Off-white solid appear in cooling slightly.Use re-crystallizing in ethyl acetate, and vacuum drying, obtain the white powder crystallization and be pure cationic surfactant.
Each functional group and embodiment 1 similar (figure slightly) in the infrared spectrum of embodiment 4.
Adopt drop-volume method to measure the surface tension of product in the aqueous solution, surface tension is with similar with Fig. 2 with the relation curve variation tendency of concentration.Along with the increase of cashew nut based quaternary ammonium salt cationic surfactant concentration of aqueous solution, the surface tension of system reduces rapidly, and catastrophe point occurs, is critical micelle concentration cmc here.Reach after the critical micelle concentration, surface tension is tending towards definite value.The critical micelle concentration cmc that can obtain this surfactant from the catastrophe point of curve is 3.9 mmol/L, and corresponding critical surface tension is 42.58 mN/m.
In four-hole boiling flask, add pentadecyl phenol, the diethylamine (0.25 mol) of 18.5 g and the ethanol of 100 mL between the 3-of 30.4 g (0.1 mol); Stir; And drip 30.4 g (0.375 mol), 37% formalin; After dropwising, 35 ℃ are reacted 1 h, back flow reaction 2 h down.Tell while hot organic facies and at a certain temperature the decompression steam solvent, obtaining 6-diethylin methyl-3-pentadecyl phenol is intermediate (Mannich alkali).
In four-hole boiling flask, add intermediate (Mannich alkali), the Celfume of 42.4 g (0.45 mol) and the ethanol of 100 mL of 19.45 g (0.05 mol), 80 ℃ of refluxed are reacted 48 h.Revolve to steam to remove and desolvate, obtain thick liquid.A large amount of Off-white solid appear in cooling slightly.Use re-crystallizing in ethyl acetate, and vacuum drying, obtain the white powder crystallization and be pure cationic surfactant.
Each functional group and embodiment 1 similar (figure slightly) in the infrared spectrum of embodiment 5.
Adopt drop-volume method to measure the surface tension of product in the aqueous solution, surface tension is with similar with Fig. 2 with the relation curve variation tendency of concentration.Along with the increase of cashew nut based quaternary ammonium salt cationic surfactant concentration of aqueous solution, the surface tension of system reduces rapidly, and catastrophe point occurs, is critical micelle concentration cmc here.Reach after the critical micelle concentration, surface tension is tending towards definite value.The critical micelle concentration cmc that can obtain this surfactant from the catastrophe point of curve is 3.4 mmol/L, and corresponding critical surface tension is 37.17 mN/m.
The foregoing description is the preferred embodiment of the present invention, but embodiment of the present invention is not restricted to the described embodiments, and other the change that any the present invention of not deviating from did all should be the substitute mode of equivalence, is included within protection scope of the present invention.
Claims (6)
1. cashew nut based quaternary ammonium salt cationic surfactant is characterized in that its general formula is:
R wherein
1, R
2, R
3Be C
1-C
4Alkyl, X is a halogen.
2. method for preparing cashew nut based quaternary ammonium salt cationic surfactant as claimed in claim 1; It is characterized in that: pentadecyl phenol, 37% formalin, secondary amine between 3-are joined in the solvent; Earlier at 10 ~ 40 ℃ of following Mannich reaction 0.5 ~ 4 h; Back flow reaction 1 ~ 4 h obtains intermediate Mannich alkali after the separation purification again; Mannich alkali and halogenated alkane are joined in the solvent, alkylated reaction 12 ~ 48 h under 65 ~ 85 ℃ of counterflow conditions, separation obtains the cashew nut based quaternary ammonium salt cationic surfactant after purifying; The solvent of said Mannich reaction and alkylated reaction is methyl alcohol, ethanol, 1-propyl alcohol, 1-butanols or isopropyl alcohol.
3. preparation method as claimed in claim 2 is characterized in that: the general formula of said secondary amine is NHR
1R
2, the general formula of said halogenated alkane is R
3X.
4. preparation method as claimed in claim 3 is characterized in that: the mol ratio of pentadecyl phenol, formaldehyde and secondary amine is 1 ︰, 2.5 ~ 5.0 ︰ 2.5 ~ 5.0 between 3-.
5. preparation method as claimed in claim 4 is characterized in that: the mol ratio of Mannich alkali and halogenated alkane is 1 ︰ 3 ~ 9.
6. preparation method as claimed in claim 5 is characterized in that: during the Mannich reaction, the consumption of solvent guarantees that the concentration of pentadecyl phenol between 3-is controlled at 0.2 ~ 1mol/L; During alkylated reaction, the consumption of solvent guarantees that the concentration of Mannich alkali is controlled at 0.2 ~ 1mol/L.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145568A (en) * | 2013-03-18 | 2013-06-12 | 东北石油大学 | Cardanol cationoid quaternary ammonium salt and preparation method thereof |
| CN103357348A (en) * | 2013-07-12 | 2013-10-23 | 北京工商大学 | Cardanol ether surfactant containing trisiloxane and preparation method of surfactant |
| CN103357347A (en) * | 2013-07-12 | 2013-10-23 | 北京工商大学 | Cardanol novel surfactant containing siloxane and preparation method of surfactant |
| CN104722240A (en) * | 2015-01-28 | 2015-06-24 | 武汉工程大学 | Trimerization surfactant with head group containing hydroxyl and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101289408A (en) * | 2007-04-18 | 2008-10-22 | 中国科学院上海药物研究所 | Non-steroid progestogen receptor regulator, preparation thereof, pharmaceutical compositions and uses |
| CN101941926A (en) * | 2009-07-09 | 2011-01-12 | 滨州美东树脂有限公司 | Cardanol polyoxyethylene ether ammonium sulfate and preparation method thereof |
| EP2314271A2 (en) * | 2009-10-21 | 2011-04-27 | Evonik Goldschmidt GmbH | Stable water-in-oil emulsion system |
-
2012
- 2012-06-26 CN CN2012102125144A patent/CN102728272A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101289408A (en) * | 2007-04-18 | 2008-10-22 | 中国科学院上海药物研究所 | Non-steroid progestogen receptor regulator, preparation thereof, pharmaceutical compositions and uses |
| CN101941926A (en) * | 2009-07-09 | 2011-01-12 | 滨州美东树脂有限公司 | Cardanol polyoxyethylene ether ammonium sulfate and preparation method thereof |
| EP2314271A2 (en) * | 2009-10-21 | 2011-04-27 | Evonik Goldschmidt GmbH | Stable water-in-oil emulsion system |
Non-Patent Citations (1)
| Title |
|---|
| 张燕晓等: "一种新型季铵盐的合成及表征", 《河南化工》, vol. 27, no. 8, 31 August 2010 (2010-08-31), pages 51 - 54 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145568A (en) * | 2013-03-18 | 2013-06-12 | 东北石油大学 | Cardanol cationoid quaternary ammonium salt and preparation method thereof |
| CN103357348A (en) * | 2013-07-12 | 2013-10-23 | 北京工商大学 | Cardanol ether surfactant containing trisiloxane and preparation method of surfactant |
| CN103357347A (en) * | 2013-07-12 | 2013-10-23 | 北京工商大学 | Cardanol novel surfactant containing siloxane and preparation method of surfactant |
| CN103357347B (en) * | 2013-07-12 | 2015-04-01 | 北京工商大学 | Cardanol novel surfactant containing siloxane and preparation method of surfactant |
| CN103357348B (en) * | 2013-07-12 | 2015-04-01 | 北京工商大学 | Cardanol ether surfactant containing trisiloxane and preparation method of surfactant |
| CN104722240A (en) * | 2015-01-28 | 2015-06-24 | 武汉工程大学 | Trimerization surfactant with head group containing hydroxyl and preparation method thereof |
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Application publication date: 20121017 |