CN111499535B - Preparation method and application of nano surfactant - Google Patents
Preparation method and application of nano surfactant Download PDFInfo
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 5
- 235000015165 citric acid Nutrition 0.000 claims description 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001630 malic acid Substances 0.000 claims description 4
- 235000011090 malic acid Nutrition 0.000 claims description 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000174 gluconic acid Substances 0.000 claims description 3
- 235000012208 gluconic acid Nutrition 0.000 claims description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 claims description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000010453 quartz Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002086 nanomaterial Substances 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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Abstract
The application discloses a preparation method and application of a nano surfactant, wherein the method at least comprises the following steps: and (3) microwave heating and synthesizing the mixture containing the micromolecular acid compound and the fatty amine to obtain the nano surfactant. The nano surfactant is prepared by adopting a microwave tube furnace, has low reaction temperature, short time and uniform heat transfer, and can be industrially produced in large scale.
Description
Technical Field
The application relates to a preparation method and application of a nano surfactant, belonging to the field of chemistry.
Background
Nanomaterials are materials that have one dimension in the three-dimensional range of 1nm to 100nm in length, and when the material or substance is reduced to the nanoscale, it will exhibit some specific properties that are different from those of large-scale substances. The surfactant is a substance which is added in a small amount and can cause the interface state of a solution system to change obviously. The molecular structure of the surfactant has amphipathy, one end of the surfactant is a nonpolar hydrocarbon chain, the affinity with water is extremely low, and the surfactant is often called as a hydrophobic group or a lipophilic group; the other end is polar group (such as-OH, -COOH, -NH, -SOH, etc.), which has great affinity with water, so it is called hydrophilic group or oleophobic group. The application of nanotechnology (nano material) in the surfactant can not only improve partial surface activity performance, but also endow surface activity nano material with properties.
The preparation of the nano surfactant reported now is generally to compound the nano particles and the surfactant or modify the nano particles by the surfactant. However, the surfactant causes serious harm to human body and environmental ecosystem in the process of production and use, and the use of the surfactant in large amount can also cause potential harm to the ecosystem. Therefore, the nano watch prepared by adopting the above thought not only has complex process, but also has certain damage to the environment.
Disclosure of Invention
According to one aspect of the application, a nano surfactant is provided, the nano surfactant is prepared by adopting a microwave tube type oven, the reaction temperature is low, the time is short, the heat transfer is uniform, and the nano surfactant can be industrially produced in large scale.
According to an aspect of the present application, there is provided a method for preparing a nano surfactant, the method at least comprising:
and (3) microwave heating and synthesizing a mixture containing the micromolecular acid compound and the fatty amine to obtain the nano surfactant.
Optionally, the small molecule acid compound is selected from at least one of malic acid, gluconic acid and citric acid.
Optionally, the frequency of the microwave tube furnace is 2-3 GHz; the rated power of the microwave is 3-5 kW; the output power is 0.2-1.30 kW.
Optionally, the temperature of the reaction is 150-220 ℃; the reaction time is 0.5-3 h.
Optionally, the reaction temperature is 150-220 ℃; the reaction time is 0.5-1.5 h.
Optionally, the heating is set by the following program: the heating rate from 25 ℃ to the reaction temperature is 5-10 ℃/min.
Optionally, the fatty amine is selected from at least one of dodecylamine, tetradecylamine, hexadecylamine, and octadecylamine.
Optionally, the method comprises at least: heating the mixture containing the micromolecular acid compound and the fatty amine in a microwave tube furnace at the temperature of 150-170 ℃, and reacting for 0.5-1 h to obtain the water-soluble nano surfactant.
Optionally, the method comprises at least: heating the mixture containing the micromolecular acid compound and the fatty amine in a microwave tube furnace at the temperature of 170-220 ℃, and reacting for 0.5-1 h to obtain the oil-soluble nano surfactant.
Optionally, the preparation method further comprises: treating tail gas generated in the preparation of the nano surfactant.
Optionally, the preparation method comprises: loading the mixture containing the small molecular acid compound and the fatty amine into a heating zone of a microwave tube furnace, closing the air inlet of the tube furnace, connecting the air outlet with a washing bottle (water is filled in the washing bottle and is discharged after tail gas treatment), heating to 150-220 ℃ for reaction for 0.5-1.5 h, and taking out the quartz boat after the reaction is finished.
Optionally, the processing method includes: and treating the tail gas by using water.
Optionally, the mass ratio of the fatty amine to the small molecular acid compound is 1:2 to 1:5.
the application also provides the nano surfactant prepared according to the method.
Optionally, the particle size of the nano surfactant is 20-350 nm.
Optionally, the upper limit of the particle size of the nano-surfactant is independently selected from 350nm, 300nm, 250nm, 200nm, 150nm, 100nm, 50nm, 30nm, and the lower limit is independently selected from 300nm, 250nm, 200nm, 150nm, 100nm, 50nm, 30nm, 20nm.
According to another aspect of the application, the nano-surfactant prepared according to the preparation method and the application of any one of the nano-surfactants in cosmetics, lubricants, emulsifiers, detergents and oilfield chemistry are also provided.
Optionally, the nano-surfactant can be applied by dissolving in water;
the nano surfactant is a water-soluble nano surfactant;
the mass volume ratio of the nano surfactant to the water is 10-200 mg/ml.
Optionally, the nano surfactant can be applied by dissolving in an organic solvent;
the nano surfactant is an oil-soluble nano surfactant;
the mass volume ratio of the nano surfactant to the organic solvent is 10-50 mg/ml.
Optionally, the organic solvent comprises any one of ethanol, tetrahydrofuran, hexane, petroleum ether, toluene.
The application also provides equipment for preparing the nano surfactant, which comprises a microwave tube type oven and a tail gas treatment device;
one end of the microwave tube type oven is provided with an opening-closing type feeding hole, the other end of the microwave tube type oven is provided with an exhaust port, and the exhaust port of the microwave tube type oven is connected with a tail gas treatment device;
and placing the mixture containing the small molecular acid compound and the fatty amine into the microwave tube type furnace through the feed inlet.
Specifically, the raw material aliphatic amine used in the application has low purity, so that small molecular organic amine gas and ammonia gas can volatilize in the product, and a tail gas treatment device is required to be used for tail gas treatment.
This application uses microwave tube furnace to react, and microwave heating makes the sample be heated evenly, and rate of heating is fast, and the required temperature of reaction is low, and reaction time is short, and is safe high-efficient.
The beneficial effects that this application can produce include:
(1) The invention synthesizes the nano surfactant by one step through a microwave tube furnace, has low temperature and short time required by reaction, and can be industrially produced in large scale;
(2) The reaction device has good leakproofness, is connected with a tail gas treatment device, has no pungent smell in the whole preparation process, and is safe and reliable.
(3) The amount of the hydrophilic groups is controlled by adjusting the reaction temperature and the reaction time, and the water-soluble surfactant and the oil-soluble surfactant can be prepared.
Drawings
The left graph in FIG. 1 is the dissolution result of sample A, B, and the right graph is the dissolution result of sample C, D.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
Unless otherwise specified, the raw materials in the examples of the present application were all purchased commercially
The particle size of the Nano surfactant prepared in the embodiment of the present application was measured using a laser particle sizer (marwen Zetasizer Nano ZSE model Nano particle sizer).
Example 1
Weighing 5g of citric acid and 2g of dodecylamine, pouring the citric acid and the dodecylamine into a quartz boat, uniformly mixing the two raw materials by using a key, loading the mixture into a heating zone of a microwave tube furnace, loading flanges at two ends of the tube furnace, connecting a gas outlet with a washing bottle (water solution in the washing bottle), and setting a temperature rise curve: heating the mixture from room temperature to 150 ℃ at a heating rate of 6 ℃/min, preserving the heat for 60min, and taking out the quartz boat after the reaction is finished to obtain the water-soluble nano surfactant A.
Example 2
Weigh 5g gluconic acid and 2.5g tetradecylamine and pour into the quartz boat, with the key with two kinds of raw materials misce benes, pack into the microwave tube furnace zone of heating, then pack the tube furnace both ends flange, the gas outlet connects the wash bottle (wash bottle in the acid solution), then sets for the curve that heaies up: the temperature is raised from room temperature to 160 ℃ at the heating rate of 6.4 ℃/min, and the temperature is kept for 90min. And (4) taking out the quartz boat after the reaction is finished, thus obtaining the water-soluble nano surfactant B.
Example 3
Weighing 5g of malic acid and 2.5g of dodecylamine, pouring the malic acid and the dodecylamine into a quartz boat, uniformly mixing the two raw materials by using a key, loading the mixture into a heating zone of a microwave tube furnace, then loading flanges at two ends of the tube furnace, connecting a gas outlet with a washing bottle (water solution in the washing bottle), and then setting a temperature rise curve: the temperature is raised from room temperature to 180 ℃ at the heating rate of 7.2 ℃/min, and the temperature is kept for 90min. And after the reaction is finished, taking out the quartz boat to obtain the oil-soluble nano surfactant C.
Example 4
Weigh 5g citric acid and 2.5g tetradecylamine and pour into the quartz boat, with the key with two kinds of raw materials misce benes, pack into the microwave tube furnace zone of heating, then pack the tube furnace both ends flange, the gas outlet connects the wash-bottle (the solution of acid in the wash-bottle), then sets for the curve that heaies up: the temperature is raised from room temperature to 220 ℃ at the heating rate of 8.8 ℃/min, and the temperature is kept for 30min. And after the reaction is finished, taking out the quartz boat to obtain the oil-soluble nano surfactant D.
Example 5 particle size testing
The method comprises the following specific steps: 0.05g of each of the nano-surfactants prepared in examples 1 to 2 was dissolved in 10mL of water to obtain a dispersion containing a water-soluble nano-surfactant, 0.05g of each of the nano-surfactants prepared in examples 3 to 4 was dissolved in 10mL of ethanol to obtain a dispersion containing an oil-soluble nano-surfactant, and the dispersion was then measured for particle size of the nano-surfactant using a laser particle sizer, the results of which are shown in Table 1.
TABLE 1
| Dispersion liquid | Particle size of nano surfactant |
| A | 306nm |
| B | 195nm |
| C | 65nm |
| D | 144nm |
Example 6 surface tension test
Examples 1 and 2 were formulated with deionized water to 3000ppm solutions, examples 3 and 4 were formulated with cyclohexane to 3000ppm solutions, and surface tension was measured with a TX500C rotary interfacial tensiometer. The results are shown in Table 2, typically in example 1 and example 4:
TABLE 2
Example 7 solubility comparison
The nano-surfactants of example 1 and example 2 were dissolved in deionized water and the nano-surfactants of example 3 and example 4 were dissolved in cyclohexane to obtain the results shown in fig. 1, the left graph in fig. 1 shows the dissolution results of sample A, B, and the right graph shows the dissolution results of sample C, D.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (11)
1. A method for preparing a nano surfactant, the method comprising:
heating a mixture containing a micromolecular acid compound and aliphatic amine in a microwave tube type oven at the temperature of 150 to 170 ℃ for reaction for 0.5 to 1h to obtain a water-soluble nano surfactant; or the like, or, alternatively,
heating a mixture containing a micromolecular acid compound and aliphatic amine in a microwave tube type oven at the temperature of 170 to 220 ℃, and reacting for 0.5 to 1h to obtain an oil-soluble nano surfactant;
the small molecular acid compound is selected from at least one of malic acid, gluconic acid and citric acid;
the fatty amine is selected from at least one of laurylamine, tetradecylamine, hexadecylamine and octadecylamine.
2. The method according to claim 1, wherein the microwave tube oven has a frequency of 2 to 3GHz; the rated power of the microwave is 3 to 5kW; the output power is 0.2 to 1.30kW.
3. The method according to claim 1, wherein the heating is set by a program of: the temperature rise rate from 25 ℃ to the reaction temperature is 5 to 10 ℃/min.
4. The method of claim 1, further comprising: treating tail gas generated in the preparation of the nano surfactant.
5. The method of claim 4, wherein the treating comprises: and treating the tail gas by using water.
6. The preparation method according to claim 1, wherein the mass ratio of the fatty amine to the small-molecule acid compound is 1:2~1:5.
7. a nano surfactant obtained by the production method according to any one of claims 1 to 6.
8. Use of any of the nano-surfactants prepared according to the process of any of claims 1 to 6, the nano-surfactants of claim 7 in cosmetics, lubricants, emulsifiers, detergents, oilfield chemistry.
9. Use according to claim 8, wherein the nano-surfactant is applied by dissolving in water;
the nano surfactant is a water-soluble nano surfactant;
the mass volume ratio of the nano surfactant to the water is 10 to 200mg/ml.
10. The use according to claim 8, wherein the nano-surfactant is applied by dissolving in an organic solvent;
the nano surfactant is an oil-soluble nano surfactant;
the mass volume ratio of the nano surfactant to the organic solvent is 10 to 50mg/ml.
11. Use according to claim 10, wherein the organic solvent comprises any of ethanol, tetrahydrofuran, hexane, petroleum ether, toluene.
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| CN1778459A (en) * | 2004-11-24 | 2006-05-31 | 李新宝 | Surface activator from citrate three-long chain alkyl triple quaternary ammonium salt cation and preparation thereof |
| CN101886202A (en) * | 2010-05-26 | 2010-11-17 | 上海大学 | A kind of method of microwave-assisted heating synthesis La-Mg hydrogen storage alloy |
| EP2706977A2 (en) * | 2011-05-10 | 2014-03-19 | Archer-Daniels-Midland Company | Dispersants having biobased compounds |
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2020
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1778459A (en) * | 2004-11-24 | 2006-05-31 | 李新宝 | Surface activator from citrate three-long chain alkyl triple quaternary ammonium salt cation and preparation thereof |
| CN101886202A (en) * | 2010-05-26 | 2010-11-17 | 上海大学 | A kind of method of microwave-assisted heating synthesis La-Mg hydrogen storage alloy |
| EP2706977A2 (en) * | 2011-05-10 | 2014-03-19 | Archer-Daniels-Midland Company | Dispersants having biobased compounds |
Non-Patent Citations (1)
| Title |
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| 小分子稠油流动性改进剂及其作用机理;张洁 等;《石油学报（石油加工）》;20131231;第29卷(第6期);第1073页2.1 * |
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