CN110813186A - Quaternary ammonium salt surfactant based on kitchen waste oil and preparation method thereof - Google Patents
Quaternary ammonium salt surfactant based on kitchen waste oil and preparation method thereof Download PDFInfo
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- CN110813186A CN110813186A CN201911132590.2A CN201911132590A CN110813186A CN 110813186 A CN110813186 A CN 110813186A CN 201911132590 A CN201911132590 A CN 201911132590A CN 110813186 A CN110813186 A CN 110813186A
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- C07—ORGANIC CHEMISTRY
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Abstract
The invention provides a quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof. The method can realize the recycling of the kitchen waste oil, and the obtained quaternary ammonium salt has excellent surface activity performance, so that the additional economic value of the kitchen waste oil recycling can be greatly improved.
Description
Technical Field
The invention relates to the technical field of comprehensive utilization of kitchen waste oil, and particularly relates to a quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof.
Background
The main component of the kitchen waste oil is triglyceride of long-chain fatty acid, and the long-chain fatty acid can be obtained by hydrolysis reaction under the condition of acid or alkali. The long-chain fatty acid is a chemical raw material with wide application, and can be used for preparing biodegradable quaternary ammonium salt derivatives with high added value. The comprehensive utilization of the kitchen waste oil can be realized, the harm of the kitchen waste oil flowing back to a dining table is reduced, and a method with a high added value is provided for the utilization of the kitchen waste oil. For example, patent CN107674030A provides a preparation method of imidazoline sulfate quaternary ammonium salt based on kitchen waste oil, to obtain an excellent corrosion inhibitor; for example, patent CN 105176693B provides a preparation method of quaternary ammonium salt based on polyhydroxy kitchen waste oil, and an excellent antistatic agent is obtained.
With the development of technology in recent years, the kinds of quaternary ammonium salts are increasing. The fatty amide propyl quaternary ammonium salt surfactant is another modified derivative which is proposed after long-chain alkyl surfactants in recent years, has low irritation, fine and rich foam, better thickening performance, excellent softness and antistatic property, is well compounded with other surfactants, and is not easy to generate precipitation. Therefore, a new idea is provided for recycling the kitchen waste oil by using the long-chain fatty acid which is the hydrolysate of the kitchen waste oil to prepare the fatty amide propyl quaternary ammonium salt.
Disclosure of Invention
Based on the above, the invention provides a quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof. The quaternary ammonium salt surfactant is prepared by taking the kitchen waste oil as a raw material, so that the waste kitchen waste oil is recycled.
In order to achieve the purpose, the quaternary ammonium salt surfactant based on the kitchen waste oil and the preparation method thereof comprise the following steps:
step 1: preparing kitchen waste oleic acid:
adding the kitchen waste oil from which insoluble substances are removed into a reaction container, adding sulfuric acid aqueous solution with the same mass, stirring and reacting for 5-8 h at 75 ℃, standing and separating after the reaction is finished and the system is cooled to room temperature, collecting oil phase, and washing with purified water for 3-5 times;
step 2: preparing kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine:
adding the kitchen waste oleic acid into a reaction container, adding a small amount of water carrying agent, heating to reaction temperature under stirring, slowly dropwise adding N, N-dimethyl-1, 3-propanediamine into the reaction container, refluxing, collecting water generated by the reaction by using a water separator until the water in the water separator is not increased any more, stopping dropwise adding the N, N-dimethyl-1, 3-propanediamine, and finishing the reaction; then distilling the mixture under reduced pressure to remove the water carrying agent and the unreacted N, N-dimethyl-1, 3-propane diamine;
and step 3: preparing kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt:
dissolving kitchen waste oleamide propyl-N, N-dimethyl tertiary amine in isopropanol, then adding the mixture into a reaction container, heating to a reaction temperature, slowly dropwise adding diethyl sulfate, stirring and refluxing until the amine value in the system is not changed, and stopping dropwise adding the diethyl sulfate and heating; and distilling the mixture under reduced pressure to remove isopropanol, recrystallizing the obtained crystals by using acetone, and collecting the crystals, namely the kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt.
Further, the concentration of the sulfuric acid aqueous solution in the step 1 is 4-8% (w/w).
Further, in the step 2, the water carrying agent may be one of benzene, toluene, petroleum ether, cyclohexane, chloroform, and carbon tetrachloride.
Further, in the step 2, the reaction temperature is 140-160 ℃, and the reaction time is 10-24 hours.
Further, in the step 3, the mass ratio of the kitchen waste oleamide propyl-N, N-dimethyl tertiary amine to the isopropanol is 1: 1-2, and the reaction temperature is 80-85 ℃.
The kitchen waste oil is hydrolyzed under an acidic condition to obtain kitchen waste oleic acid, the kitchen waste oleic acid is used for synthesizing kitchen waste oil aminopropyl-N, N-dimethyl tertiary amine, and the product is further quaternized to obtain the quaternary ammonium salt with a fatty amide structure. The method can realize the recycling of the kitchen waste oil, and the obtained quaternary ammonium salt has excellent surface activity performance, so that the additional economic value of the kitchen waste oil recycling can be greatly improved.
Detailed Description
Example 1
A quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof comprise the following steps:
step 1: preparing kitchen waste oleic acid:
adding 100g of kitchen waste oil from which insoluble substances are removed into a three-neck flask, adding 100g of sulfuric acid aqueous solution with the mass fraction of 4% into the three-neck flask, stirring and reacting for 5 hours at 75 ℃, after the reaction is finished, cooling the system to room temperature, standing and separating liquid, and washing the oil phase with purified water for 3-5 times;
step 2: preparing kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine:
adding 100g of kitchen waste oleic acid into a reaction container, adding 10g of toluene, heating to 140 ℃ under a stirring condition, slowly dropwise adding N, N-dimethyl-1, 3-propanediamine into the reaction container, refluxing, collecting water generated by the reaction by using a water separator, stopping dropwise adding the N, N-dimethyl-1, 3-propanediamine until the water in the water separator is not increased any more, and finishing the reaction; after the reaction is finished, distilling the mixture under reduced pressure to remove the water carrying agent and the unreacted N, N-dimethyl-1, 3-propane diamine;
and step 3: preparing kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt:
dissolving 50g of kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine in 50g of isopropanol, then adding the mixture into a reaction container, heating to 82 ℃, and stirring and refluxing; detecting the amine value in the reaction system every half hour until the amine value is unchanged, and finishing the reaction; and distilling the mixture under reduced pressure to remove isopropanol, and recrystallizing with acetone to obtain a crystal, namely the kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt.
Example 2
A quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof are as follows:
step 1: preparing kitchen waste oleic acid:
adding 100g of kitchen waste oil from which insoluble substances are removed into a three-neck flask, adding 100g of sulfuric acid aqueous solution with the mass fraction of 4% into the three-neck flask, stirring the mixture at 75 ℃ for reaction for 5 hours, cooling the reaction system to room temperature, standing the mixture for liquid separation, and washing the oil phase with purified water for 3-5 times;
step 2: preparing kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine:
adding 100g of kitchen waste oleic acid into a reaction container, adding 10g of toluene, heating to 150 ℃ under a stirring condition, slowly dropwise adding N, N-dimethyl-1, 3-propanediamine into the reaction container, refluxing, collecting water generated by the reaction by using a water separator, stopping dropwise adding the N, N-dimethyl-1, 3-propanediamine until the water in the water separator is not increased any more, and finishing the reaction; after the reaction is finished, distilling the mixture under reduced pressure to remove the water carrying agent and the unreacted N, N-dimethyl-1, 3-propane diamine;
and step 3: preparing kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt:
dissolving 50g of kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine in 50g of isopropanol, then adding the mixture into a reaction container, heating to 82 ℃, and stirring and refluxing; detecting the amine value in the reaction system every half hour until the amine value is unchanged, and finishing the reaction; and distilling the mixture under reduced pressure to remove isopropanol, and recrystallizing with acetone to obtain a crystal, namely the kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt.
Example 3
A quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof are as follows:
step 1: preparing kitchen waste oleic acid:
adding 100g of kitchen waste oil from which insoluble substances are removed into a three-neck flask, adding 100g of sulfuric acid aqueous solution with the mass fraction of 4% into the three-neck flask, stirring the mixture at 75 ℃ for reaction for 5 hours, cooling the reaction system to room temperature, standing the mixture for liquid separation, and washing the oil phase with purified water for 3-5 times;
step 2: preparing kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine:
adding 100g of kitchen waste oleic acid into a reaction container, adding 10g of toluene, heating to 160 ℃ under a stirring condition, slowly dropwise adding N, N-dimethyl-1, 3-propanediamine into the reaction container, refluxing, collecting water generated by the reaction by using a water separator, stopping dropwise adding the N, N-dimethyl-1, 3-propanediamine until the water in the water separator is not increased any more, and finishing the reaction; after the reaction is finished, distilling the mixture under reduced pressure to remove the water carrying agent and the unreacted N, N-dimethyl-1, 3-propane diamine;
and step 3: preparing kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt:
dissolving 50g of kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine in 50g of isopropanol, then adding the mixture into a reaction container, heating to 82 ℃, and stirring and refluxing; detecting the amine value in the reaction system every half hour until the amine value is unchanged, and finishing the reaction; and distilling the mixture under reduced pressure to remove isopropanol, and recrystallizing with acetone to obtain a crystal, namely the kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt.
Example 4
Sample surface active Property test
The surface tension of the quaternary ammonium salt prepared in the embodiment is measured by a hanging ring method, the measuring temperature is 25 ℃, and the solution concentration is 0.1%; the foam surface type is measured by adopting a Roche foam instrument method in GB/T13173.6-2000, the measurement temperature is 40 ℃, and the solution concentration is 0.25%; the emulsifying property is measured by taking 0.1 percent of water solution and 20ml of 0# diesel oil to be evenly mixed in a measuring cylinder with a plug, and measuring the time for separating 5ml of water phase, wherein the longer the time for separating water is, the better the emulsifying property is; the test data are shown in the following table:
table 1 surface Property test data
The data in the table show that the quaternary ammonium salt prepared in the example has better surface activity performance.
The above embodiment is a further introduction to the present invention, and the key factor affecting the yield of the quaternary ammonium salt of the present invention is the conversion rate of the kitchen waste oleamide propyl-N, N-dimethyl tertiary amine in step 2, and the main factors affecting the conversion rate include the molar ratio of the kitchen waste oleic acid to the N, N-dimethyl-1, 3-propane diamine, and the reaction temperature; in the method, the N, N-dimethyl-1, 3-propane diamine is excessively added, so that the main reason influencing the conversion rate is the reaction temperature; in the embodiments 1-3, the reaction temperature of the step 2 is 140 ℃, 150 ℃ and 160 ℃, the conversion rates of the corresponding kitchen waste oleic acid are sequentially increased, and finally the yield of the quaternary ammonium salt is increased.
Meanwhile, the components of the kitchen waste oil from different sources have some differences, and the reaction conditions need to be optimized according to actual conditions when the method is implemented. Accordingly, the present invention includes, but is not limited to, the above-described embodiments, which are intended to be illustrative, not limiting. Those skilled in the art should appreciate that they can readily use the disclosed conception and specific embodiments as a basis for designing or modifying other structures for carrying out the same purposes of the present invention.
Claims (5)
1. A quaternary ammonium salt surfactant based on kitchen waste oil and a preparation method thereof are characterized by comprising the following steps:
step 1: preparing kitchen waste oleic acid:
adding the kitchen waste oil from which insoluble substances are removed into a reaction container, adding sulfuric acid aqueous solution with the same mass, stirring and reacting for 5-8 h at 75 ℃, standing and separating after the reaction is finished and the system is cooled to room temperature, collecting oil phase, and washing with purified water for 3-5 times;
step 2: preparing kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine:
adding the kitchen waste oleic acid into a reaction container, adding a small amount of water carrying agent, heating to reaction temperature under stirring, slowly dropwise adding N, N-dimethyl-1, 3-propanediamine into the reaction container, refluxing, collecting water generated by the reaction by using a water separator until the water in the water separator is not increased any more, stopping dropwise adding the N, N-dimethyl-1, 3-propanediamine, and finishing the reaction; then distilling the mixture under reduced pressure to remove the water carrying agent and the unreacted N, N-dimethyl-1, 3-propane diamine;
and step 3: preparing kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt:
dissolving kitchen waste oleamide propyl-N, N-dimethyl tertiary amine in isopropanol, then adding the mixture into a reaction container, heating to a reaction temperature, slowly dropwise adding diethyl sulfate, stirring and refluxing until the amine value in the system is not changed, and stopping dropwise adding the diethyl sulfate and heating; and distilling the mixture under reduced pressure to remove isopropanol, recrystallizing the obtained crystals by using acetone, and collecting the crystals, namely the kitchen waste oil amidopropyl-N, N-dimethyl quaternary ammonium salt.
2. The quaternary ammonium salt surfactant based on the kitchen waste oil and the preparation method thereof according to claim 1, wherein the quaternary ammonium salt surfactant is characterized in that: the mass percentage concentration of the sulfuric acid aqueous solution in the step 1 is 4-8%.
3. The quaternary ammonium salt surfactant based on kitchen waste oil and the preparation method thereof according to claim 1, wherein the water carrying agent in the step 2 can be one of benzene, toluene, petroleum ether, cyclohexane, chloroform and carbon tetrachloride.
4. The quaternary ammonium salt surfactant based on kitchen waste oil and the preparation method thereof according to claim 1, wherein the reaction temperature in the step 2 is 140-160 ℃, and the reaction time is 10-24 hours.
5. The quaternary ammonium salt surfactant based on kitchen waste oil and the preparation method thereof according to claim 1, wherein in the step 3, the mass ratio of the kitchen waste oil amidopropyl-N, N-dimethyl tertiary amine to the isopropanol is 1: 1-2, and the reaction temperature is 80-85 ℃.
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| CN111454209A (en) * | 2020-03-18 | 2020-07-28 | 滨州德润化工有限责任公司 | Preparation process of corrosion inhibitor imidazoline for oil field water treatment |
| CN112694416A (en) * | 2020-12-28 | 2021-04-23 | 浙江传化华洋化工有限公司 | Ester-based quaternary ammonium salt paper-making drying cylinder stripping agent and preparation method thereof |
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