CN114276281A - Light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as well as preparation method and application thereof - Google Patents
Light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as well as preparation method and application thereof Download PDFInfo
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- CN114276281A CN114276281A CN202111626493.6A CN202111626493A CN114276281A CN 114276281 A CN114276281 A CN 114276281A CN 202111626493 A CN202111626493 A CN 202111626493A CN 114276281 A CN114276281 A CN 114276281A
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- polyoxyethylene ether
- cardanol polyoxyethylene
- ammonium sulfate
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- anionic surfactant
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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Abstract
The invention discloses a preparation method of a light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant, which comprises the following steps: 1) mixing cardanol polyoxyethylene ether, a catalyst and a reducing agent, and then heating to 80-110 ℃ for dehydration; 2) adding sulfamic acid into the reaction solution obtained in the step 1), and then heating to 100-125 ℃ for heat preservation reaction; 3) and after the reaction is finished, cooling to 60-75 ℃, simultaneously adding an alcohol solvent for viscosity reduction, filtering to remove insoluble substances, and drying the filtered material to obtain the product. The preparation method comprises the steps of taking cardanol polyoxyethylene ether and sulfamic acid as raw materials, adding a reducing agent as a color stabilizer, and reacting under the action of a catalyst to obtain light-color cardanol polyoxyethylene ether ammonium sulfate.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as well as a preparation method and application thereof.
Background
The alkylphenol polyoxyethylene ether ammonium sulfate salt is developed by countries such as Europe and America in the 80 th of the 20 th century, has the outstanding advantages of strong permeability, high detergency, good compatibility, rapid dissolution and the like, has good foamability and foam stability, high solubilizing ability on inorganic salt and weak irritation to human skin, and can be used in the fields of personal care, petroleum industry, textile industry, pesticide production, industrial cleaning and the like.
At present, alkylphenol polyoxyethylene ether ammonium sulfate is mainly prepared by reacting alkylphenol polyoxyethylene ether with sulfamic acid under the condition that urea is used as a catalyst. Because the alkylphenol polyoxyethylene ether ammonium sulfate is synthesized by petroleum alkylphenol, environmental pollution is caused, and the alkylphenol polyoxyethylene ether ammonium sulfate is forbidden by many developed countries, the synthesis of the polyoxyethylene ether ammonium sulfate by adopting natural phenol to replace petroleum phenol has important environmental advantages.
Chinese patent CN101941926A discloses a cardanol polyoxyethylene ether sulfate ammonium salt and a preparation method thereof, wherein cardanol polyoxyethylene ether, sulfamic acid and a catalyst are adopted to react at 110-150 ℃, then sodium hydroxide is used for neutralization, and the product is obtained after cooling and filtering. However, under the long-term high-temperature reaction condition of 110-150 ℃, cardanol polyoxyethylene ether/cardanol polyoxypropylene polyoxyethylene ether/cardanol polyoxyethylene polyoxypropylene ether can be oxidized, so that the color of a finished product is very dark, and in the process of replacing ammonia with alkali, the pH value of the product is under an alkaline condition, and the color of the product can be further dark. Although hydrogen peroxide can be used for bleaching subsequently, the bleaching effect is poor, and once the hydrogen peroxide is completely decomposed, the color of the product quickly becomes darker.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as well as a preparation method and application thereof.
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of a light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant comprises the following steps:
1) mixing cardanol polyoxyethylene ether, a catalyst and a reducing agent, and then heating to 80-110 ℃;
2) adding sulfamic acid into the reaction solution obtained in the step 1), and then heating to 100-125 ℃ for heat preservation reaction;
4) and after the reaction is finished, cooling to 60-75 ℃, simultaneously adding an alcohol solvent for viscosity reduction, filtering to remove insoluble substances, and drying the filtered material to obtain the product.
Preferably, the catalyst comprises carbamide or dicyandiamide.
Preferably, the reducing agent comprises hypophosphorous acid or a hypophosphite.
Preferably, the cardanol polyoxyethylene ether, the catalyst, the reducing agent and the sulfamic acid are in a molar ratio of 1: (0.2-0.6): (0.05-0.3): (1.0-1.2).
Preferably, in step 2), sulfamic acid is added to the reaction solution obtained in step 1) in portions.
Preferably, in step 3), the alcohol solvent is C1-4Monohydric alcohols including methanol, ethanol or isobutanol.
Preferably, the effective content of the cardanol polyoxyethylene ether is more than 90%, the structural formula of the cardanol polyoxyethylene ether is shown as follows,
wherein n is 0, 2, 4 or 6; m is 2 to 7
Preferably, the rest of the cardanol polyoxyethylene ether comprises cardol polyoxyethylene ether and 2-methyl cardol polyoxyethylene ether.
The surfactant prepared by the preparation method of the light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant.
The surfactant is applied to daily chemical cleaning.
In conclusion, the invention has the following beneficial effects:
1. the preparation method has simple process and high conversion rate;
2. the product prepared by the preparation method has small color number, light color and high color stability, can be effectively maintained after high-temperature treatment, has excellent detergency while maintaining the light color, and has very good cleaning effect on standard dirty cloth when being applied to daily chemical cleaning.
Detailed Description
The present invention is further explained.
The embodiment discloses a preparation method of a light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant, which comprises the following steps:
1) mixing cardanol polyoxyethylene ether, a catalyst and a reducing agent, starting stirring, heating to 80-110 ℃, and vacuumizing and dehydrating for 20-60 minutes; wherein the catalyst comprises carbamide or dicyandiamide and the reducing agent comprises hypophosphorous acid or hypophosphite;
2) adding sulfamic acid into the reaction solution obtained in the step 1) for several times, wherein the interval between every two times is 10 minutes; wherein the mol ratio of the cardanol polyoxyethylene ether to the catalyst to the reducing agent to the sulfamic acid is 1: (0.2-0.6): (0.05-0.3): (1.0-1.2).
3) Then heating to 100-125 ℃, and carrying out heat preservation reaction for 3-6 hours;
4) after the reaction is finished, cooling to 60-75 ℃, simultaneously adding an alcohol solvent for viscosity reduction, filtering to remove insoluble substances, drying the filtered material, vacuumizing to remove the solvent, and further obtaining the product, wherein the alcohol solvent is C1-4Monohydric alcohols including methanol, ethanol or isobutanol.
The effective content of the cardanol polyoxyethylene ether is more than 90 percent, and the structural formula is
Wherein n is 0, 2, 4 or 6; m is 2-7, and the rest components comprise cardol polyoxyethylene ether and 2-methyl cardol polyoxyethylene ether.
The surfactant prepared by the preparation method of the light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant.
The surfactant is applied to daily chemical cleaning.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
Example 1
1. Adding 564g (about 1mol) of cardanol polyoxyethylene ether (6), 18g (about 0.3mol) of carbamide and 13.2g (about 0.1mol) of hypophosphorous acid into a four-mouth bottle, heating to 90 ℃, and vacuumizing and dehydrating for 30 minutes;
2. adding 107g (about 1.1mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually heating to 115 ℃ after the addition, and carrying out heat preservation reaction for 4 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75 deg.C, vacuumizing to remove ethanol, and discharging.
Example 2
1. Adding 564g (about 1mol) of cardanol polyoxyethylene ether (6), 18g (about 0.3mol) of carbamide and 39.6g (about 0.3mol) of hypophosphorous acid into a four-mouth bottle, heating to 95 ℃, and vacuumizing and dehydrating for 30 minutes;
2. adding 107g (about 1.1mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually raising the temperature to 115 ℃ after the addition, and keeping the temperature for reaction for 3 hours;
3. cooling to 65 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70 deg.C, vacuumizing to remove ethanol, and discharging.
Example 3
1. Adding 564g (about 1mol) of cardanol polyoxyethylene ether (6), 30g (about 0.5mol) of carbamide and 21.2 (about 0.2mol) of sodium hypophosphite into a four-mouth bottle, heating to 100 ℃, and vacuumizing and dehydrating for 30 minutes;
2. adding 112g (about 1.15mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually raising the temperature to 120 ℃ after the addition, and carrying out heat preservation reaction for 3 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75 deg.C, vacuumizing to remove ethanol, and discharging.
Example 4
1. Adding 564g (about 1mol) of cardanol polyoxyethylene ether (6), 24g (about 0.4mol) of carbamide and 26.4 (about 0.2mol) of hypophosphorous acid into a four-mouth bottle, heating to 105 ℃, and vacuumizing and dehydrating for 40 minutes;
2. adding 97g (about 1mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually heating to 110 ℃ after the addition, and carrying out heat preservation reaction for 5 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75 deg.C, vacuumizing to remove ethanol, and discharging.
Example 5
1. Adding 476g (about 1mol) of cardanol polyoxyethylene ether (4), 30g (about 0.5mol) of carbamide and 26.4 (about 0.2mol) of hypophosphorous acid into a four-mouth bottle, heating to 100 ℃, and vacuumizing and dehydrating for 40 minutes;
2. adding 112g (about 1.15mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually raising the temperature to 110 ℃ after the addition, and keeping the temperature for reaction for 5 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70 deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 1
1. Adding 564g (about 1mol) of cardanol polyoxyethylene ether (6), 18g (about 0.3mol) of carbamide and 24 (about 0.2mol) of sodium dihydrogen phosphite into a four-mouth bottle, heating to 95 ℃, and vacuumizing and dehydrating for 40 minutes;
2. adding 107g (about 1.1mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually heating to 115 ℃ after the addition, and carrying out heat preservation reaction for 5 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70 deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 2:
1. adding 564g (about 1mol) of cardanol polyoxyethylene ether (6) and 18g (about 0.3mol) of carbamide into a four-mouth bottle, heating to 95 ℃, and vacuumizing and dehydrating for 30 minutes;
2. adding 107g (about 1.1mol) of sulfamic acid in five times, wherein the time interval is 10 minutes, gradually raising the temperature to 120 ℃ after the addition, and keeping the temperature for reaction for 4 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75 deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 3
1. Adding 564g (about 1mol) of cardanol polyoxyethylene ether (6) and 18g (about 0.3mol) of carbamide into a four-mouth bottle, heating to 100 ℃, and vacuumizing and dehydrating for 20 minutes;
2. adding 107g (about 1.1mol) of sulfamic acid five times, wherein the time interval is 10 minutes, gradually raising the temperature to 125 ℃ after the addition, and keeping the temperature for reaction for 3 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70 deg.C, vacuum-pumping to remove ethanol, adding 30% hydrogen peroxide, heating to 80 deg.C, vacuum-pumping to dewater, stirring for 60 min, and discharging.
Comparative example 4:
1. adding 564g (about 1mol) of cardanol polyoxyethylene ether (6) and 13.2g (about 0.1mol) of hypophosphorous acid into a four-mouth bottle, and heating to 100 ℃;
2. adding 107g (about 1.1mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually heating to 115 ℃ after the addition, and carrying out heat preservation reaction for 4 hours;
3. cooling to 70 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70 deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 5:
1. 564g (about 1mol) of cardanol polyoxyethylene ether (6) is added into a four-mouth bottle, and the temperature is raised to 95 ℃;
2. adding 107g (about 1.1mol) of sulfamic acid for four times, wherein the time interval is 10 minutes, gradually heating to 115 ℃ after the addition, and carrying out heat preservation reaction for 5 hours;
3. cooling to 65 deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70 deg.C, vacuumizing to remove ethanol, and discharging.
The experimental results of examples 1 to 5 and comparative examples 1 to 5 are shown in the following table 1:
TABLE 1
As can be seen from Table 1, the examples have the advantages of obvious conversion rate, small color number and effective maintenance after high-temperature treatment. The detergent has excellent detergency while keeping light color.
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and embellishments within the scope of the invention may occur to those skilled in the art without departing from the principle of the invention, and are considered to be within the scope of the invention.
Claims (10)
1. A preparation method of a light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant is characterized by comprising the following steps:
1) mixing cardanol polyoxyethylene ether, a catalyst and a reducing agent, and then heating to 80-110 ℃ for dehydration;
2) adding sulfamic acid into the reaction solution obtained in the step 1), and then heating to 100-125 ℃ for heat preservation reaction;
3) and after the reaction is finished, cooling to 60-75 ℃, simultaneously adding an alcohol solvent for viscosity reduction, filtering to remove insoluble substances, and drying the filtered material to obtain the product.
2. The method of making the light colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant of claim 1, wherein said catalyst comprises carbamide or dicyandiamide.
3. The method for preparing the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in claim 1 or 2, wherein the reducing agent comprises hypophosphorous acid or hypophosphite.
4. The method for preparing the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in claim 3, wherein the molar ratio of the cardanol polyoxyethylene ether, the catalyst, the reducing agent and the sulfamic acid is 1: (0.2-0.6): (0.05-0.3): (1.0-1.2).
5. The method for preparing the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in claim 1, wherein in step 2), sulfamic acid is added to the reaction solution obtained in step 1) in portions.
6. The method for preparing the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in claim 1, wherein in step 3), the alcohol solvent is C1-4Monohydric alcohols including methanol, ethanol or isobutanol.
7. The preparation method of the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in claim 1, wherein the effective content of cardanol polyoxyethylene ether is more than 90%, and the structural formula of cardanol polyoxyethylene ether is shown in the specification
Wherein n is 0, 2, 4 or 6, and m is 2-7.
8. The method for preparing the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in claim 1, wherein the rest of cardanol polyoxyethylene ether comprises cardol polyoxyethylene ether and 2-methyl cardol polyoxyethylene ether.
9. The surfactant prepared by the preparation method of the light-color cardanol polyoxyethylene ether ammonium sulfate anionic surfactant as claimed in any one of claims 1-8.
10. Use of a surfactant according to claim 9 in daily chemical cleaning.
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| CN115417983A (en) * | 2022-09-05 | 2022-12-02 | 华东理工大学 | Cardanol polyether sulfate and preparation method and application thereof |
| CN116350541A (en) * | 2023-01-13 | 2023-06-30 | 华东理工大学 | Cleansing water with cardanol polyoxyethylene ether as surfactant component |
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| WO2023227358A1 (en) | 2022-05-27 | 2023-11-30 | Unilever Ip Holdings B.V. | Premix and composition and method of preparing the same |
| WO2023227357A1 (en) | 2022-05-27 | 2023-11-30 | Unilever Ip Holdings B.V. | Composition |
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