CN114276281B - Light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant and preparation method and application thereof - Google Patents
Light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant and preparation method and application thereof Download PDFInfo
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- CN114276281B CN114276281B CN202111626493.6A CN202111626493A CN114276281B CN 114276281 B CN114276281 B CN 114276281B CN 202111626493 A CN202111626493 A CN 202111626493A CN 114276281 B CN114276281 B CN 114276281B
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- polyoxyethylene ether
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Abstract
The invention discloses a preparation method of a light-colored 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 liquid 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. According to the preparation method, cardanol polyoxyethylene ether and sulfamic acid are used as raw materials, a reducing agent is added as a color stabilizer, and the reaction is carried out under the action of a catalyst, so that light-color cardanol polyoxyethylene ether ammonium sulfate is obtained.
Description
Technical Field
The invention relates to the technical field of surfactants, in particular to a light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant, a preparation method and application thereof.
Background
The alkylphenol polyoxyethylene ether ammonium sulfate is developed from countries such as Europe and America in the 80 th century, has the outstanding advantages of strong permeability, high detergency, good compatibility, quick dissolution and the like, has good foamability and foam stability, has high solubilization capacity for inorganic salts 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 mainly reacts with sulfamic acid under the condition that urea is used as a catalyst. Because alkylphenol polyoxyethylene ether ammonium sulfate is synthesized from petroleum alkylphenol, which causes environmental pollution, and is forbidden by many developed countries, the synthesis of polyoxyethylene ether ammonium sulfate by using natural phenol instead of 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 ℃, and 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 ℃, the 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 of the product is in an alkaline condition, and the color of the product can be further darkened. 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 can be quickly deepened.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention provides a light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant, and a preparation method and application thereof.
In order to achieve the above purpose, the present invention provides the following technical solutions: the preparation method of the light-colored 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 liquid 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 a carboxamide or dicyandiamide.
Preferably, the reducing agent comprises hypophosphorous acid or hypophosphite.
Preferably, 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).
Preferably, in step 2), sulfamic acid is added to the reaction solution obtained in step 1) in portions.
Preferably, in step 3), the alcoholic solvent is C 1-4 Monohydric alcohols, including methanol, ethanol, or isobutanol.
Preferably, the cardanol polyoxyethylene ether has an effective content of more than 90 percent, the structural formula is shown as follows,
wherein n is 0, 2, 4, 6; m is 2 to 7
Preferably, the rest components of the cardanol polyoxyethylene ether comprise the cardiotonic polyoxyethylene ether and the 2-methyl cardiotonic polyoxyethylene ether.
The surfactant is prepared by the preparation method of the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant.
The surfactant is applied to daily chemical cleaning.
In summary, 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 still effectively maintained after high-temperature treatment, has excellent detergency while keeping light color, and has very good cleaning effect on standard dirty cloth when being applied to daily chemical cleaning.
Detailed Description
The invention will be further described.
The embodiment discloses a preparation method of a light-colored 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 a carboxamide or dicyandiamide and the reducing agent comprises hypophosphorous acid or hypophosphite;
2) Adding sulfamic acid into the reaction liquid obtained in the step 1) in batches, wherein each batch is divided into 10 minutes; wherein, the molar 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 preserving heat for 3-6 hours;
4) Cooling to 60-75 ℃ after the reaction is finished, adding an alcohol solvent for viscosity reduction, filtering to remove insoluble substances, drying the filtered materials, vacuumizing to remove the solvent, and obtaining a product, wherein the alcohol solvent is C 1-4 Monohydric alcohols, including methanol, ethanol, or isobutanol.
The cardanol polyoxyethylene ether has an effective content of more than 90 percent and a structural formula of
Wherein n is 0, 2, 4, 6; m is 2-7, and the rest components comprise the cardiotonic phenol polyoxyethylene ether and the 2-methyl cardiotonic phenol polyoxyethylene ether.
The surfactant prepared by the preparation method of the light-colored 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. 564g (about 1 mol), 18g (about 0.3 mol) of carbonamide and 13.2g (about 0.1 mol) of hypophosphorous acid are added into a four-mouth bottle, the temperature is raised to 90 ℃, and the vacuum dehydration is carried out for 30 minutes;
2. adding 107g (about 1.1 mol) of sulfamic acid in four times at intervals of 10 minutes, gradually heating to 115 ℃ after the addition, and preserving heat for 4 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75deg.C, vacuumizing to remove ethanol, and discharging.
Example 2
1. 564g (about 1 mol), 18g (about 0.3 mol) of carbonamide and 39.6g (about 0.3 mol) of hypophosphorous acid are added into a four-mouth bottle, the temperature is raised to 95 ℃, and the vacuum dehydration is carried out for 30 minutes;
2. adding 107g (about 1.1 mol) of sulfamic acid in four times, wherein each time is 10 minutes apart, gradually heating to 115 ℃ after the addition, and preserving heat for 3 hours;
3. cooling to 65deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70deg.C, vacuumizing to remove ethanol, and discharging.
Example 3
1. 564g (about 1 mol), 30g (about 0.5 mol) of carbonamide and 21.2 (about 0.2 mol) of sodium hypophosphite of cardanol polyoxyethylene ether (6) are added into a four-mouth bottle, the temperature is raised to 100 ℃, and the vacuum dehydration is carried out for 30 minutes;
2. 112g (about 1.15 mol) of sulfamic acid is added in four times, each time is separated by 10 minutes, the temperature is gradually increased to 120 ℃ after the addition, and the reaction is carried out for 3 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75deg.C, vacuumizing to remove ethanol, and discharging.
Example 4
1. 564g (about 1 mol), 24g (about 0.4 mol) of carbonamide and 26.4 (about 0.2 mol) of hypophosphorous acid are added into a four-mouth bottle, the temperature is raised to 105 ℃, and the vacuum dehydration is carried out for 40 minutes;
2. 97g (about 1 mol) of sulfamic acid is added in four times, each time is separated by 10 minutes, the temperature is gradually increased to 110 ℃ after the addition, and the reaction is carried out for 5 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75deg.C, vacuumizing to remove ethanol, and discharging.
Example 5
1. 476g (about 1 mol) of cardanol polyoxyethylene ether (4), 30g (about 0.5 mol) of carbonamide and 26.4 (about 0.2 mol) of hypophosphorous acid are added into a four-mouth bottle, the temperature is raised to 100 ℃, and the vacuum dehydration is carried out for 40 minutes;
2. 112g (about 1.15 mol) of sulfamic acid is added in four times, each time is separated by 10 minutes, and after the addition is finished, the temperature is gradually increased to 110 ℃, and the reaction is carried out for 5 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating to 70deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 1
1. 564g (about 1 mol) of cardanol polyoxyethylene ether (6), 18g (about 0.3 mol) of carbonamide and 24 (about 0.2 mol) of sodium dihydrogen phosphite are added into a four-mouth bottle, the temperature is raised to 95 ℃, and the vacuum dehydration is carried out for 40 minutes;
2. adding 107g (about 1.1 mol) of sulfamic acid in four times at intervals of 10 minutes, gradually heating to 115 ℃ after the addition, and preserving heat for reaction for 5 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating to 70deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 2:
1. 564g (about 1 mol) of cardanol polyoxyethylene ether (6) and 18g (about 0.3 mol) of carbonamide are added into a four-mouth bottle, the temperature is raised to 95 ℃, and the vacuum dehydration is carried out for 30 minutes;
2. adding 107g (about 1.1 mol) of sulfamic acid in five times at intervals of 10 minutes, gradually heating to 120 ℃ after the addition, and preserving heat for 4 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 75deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 3
1. 564g (about 1 mol) of cardanol polyoxyethylene ether (6) and 18g (about 0.3 mol) of carbonamide are added into a four-mouth bottle, the temperature is raised to 100 ℃, and the vacuum dehydration is carried out for 20 minutes;
2. adding 107g (about 1.1 mol) of sulfamic acid in five times at intervals of 10 minutes, gradually heating to 125 ℃ after the addition, and preserving heat for reaction for 3 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70deg.C, vacuumizing to remove ethanol, adding 30% hydrogen peroxide, heating to 80deg.C, vacuumizing to dehydrate, stirring for 60 min, and discharging.
Comparative example 4:
1. 564g (about 1 mol) of cardanol polyoxyethylene ether (6) and 13.2g (about 0.1 mol) of hypophosphorous acid are added into a four-mouth bottle, and the temperature is raised to 100 ℃;
2. adding 107g (about 1.1 mol) of sulfamic acid in four times at intervals of 10 minutes, gradually heating to 115 ℃ after the addition, and preserving heat for 4 hours;
3. cooling to 70deg.C, adding ethanol, filtering to remove insoluble impurities, heating to 70deg.C, vacuumizing to remove ethanol, and discharging.
Comparative example 5:
1. 564g (about 1 mol) of cardanol polyoxyethylene ether (6) is added into a four-mouth bottle, and the temperature is raised to 95 ℃;
2. adding 107g (about 1.1 mol) of sulfamic acid in four times at intervals of 10 minutes, gradually heating to 115 ℃ after the addition, and preserving heat for reaction for 5 hours;
3. cooling to 65deg.C, adding ethanol, filtering to remove insoluble impurities, heating the filtered material to 70deg.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 significant conversion advantages and small color number, and remain effective after high temperature treatment. The color is kept light, and meanwhile, the detergent has excellent detergency.
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 examples, and all technical solutions belonging to the concept of the present invention belong to the protection scope of the present invention. It should be noted that modifications and adaptations to the present invention may occur to one skilled in the art without departing from the principles of the present invention and are intended to be within the scope of the present invention.
Claims (4)
1. The preparation method of the light-colored cardanol polyoxyethylene ether ammonium sulfate anionic surfactant is characterized by comprising the following steps of:
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 liquid obtained in the step 1), and then heating to 100-125 ℃ for heat preservation reaction;
3) Cooling to 60-75 ℃ after the reaction is finished, adding an alcohol solvent to reduce viscosity, filtering to remove insoluble substances, and drying the filtered material to obtain a product;
the catalyst is a carboxamide; the reducing agent is hypophosphorous acid or hypophosphite;
the molar 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 to 1.2);
the effective content of the cardanol polyoxyethylene ether is more than 90%, and the structural formula is
Wherein n is 0, 2, 4, 6, m is 2-7; the rest components of the cardanol polyoxyethylene ether are cardiotonic polyoxyethylene ether and 2-methyl cardiotonic polyoxyethylene ether.
2. The process for producing a pale cardanol polyoxyethylene ether ammonium sulfate anionic surfactant according to claim 1, wherein sulfamic acid is added to the reaction solution obtained in step 1) in step 2) in several steps.
3. The process for producing a pale cardanol polyoxyethylene ether ammonium sulfate anionic surfactant according to claim 1, which is characterized in thatCharacterized in that in the step 3), the alcohol solvent is C 1-4 Monohydric alcohols.
4. The process for preparing a pale cardanol polyoxyethylene ether ammonium sulfate anionic surfactant according to claim 3, wherein the said C 1-4 The monohydric alcohol is methanol, ethanol or isobutanol.
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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 |
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| CN101235001A (en) * | 2007-12-21 | 2008-08-06 | 王伟松 | Method for synthesizing aliphatic alcohol sulfate |
| 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 |
| CN102746198A (en) * | 2012-06-29 | 2012-10-24 | 成都达威化工科技有限公司 | Method for preparing leather fat-liquoring agent |
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