CN114380710A - Preparation method of salt-free imidazoline amphoteric surfactant - Google Patents
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- CN114380710A CN114380710A CN202111638723.0A CN202111638723A CN114380710A CN 114380710 A CN114380710 A CN 114380710A CN 202111638723 A CN202111638723 A CN 202111638723A CN 114380710 A CN114380710 A CN 114380710A
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- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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Abstract
The invention provides a preparation method of a salt-free imidazoline amphoteric surfactant, and relates to the technical field of fine chemical preparation. According to the preparation method provided by the invention, on the basis of the traditional oxazoline amphoteric surfactant synthesis process, after the imidazoline intermediate is synthesized, an alkaline substance is introduced into a system in a water solution mode to be mixed with the imidazoline intermediate, so that the ring opening of the imidazoline intermediate is promoted to form a chain structure, and the active site of secondary amine is ensured; then, an alkylation reagent is used for reaction, and an alkaline system is used for hydrolysis to prepare the target product. According to the technical scheme, chloroacetic acid and salts thereof are not used as alkylating reagents, a new synthesis path is provided for preparation of the imidazoline amphoteric surfactant, and the prepared target product does not contain chloroacetic acid and glycolic acid impurities and inorganic salts such as NaCl.
Description
Technical Field
The invention relates to the technical field of fine chemical preparation, and particularly relates to a preparation method of a salt-free imidazoline amphoteric surfactant.
Background
The oxazoline amphoteric surfactant is mainly prepared by fatty acid or ester thereof and polyamine through dehydration condensation, ring closure and new group introduction, and the synthetic steps are mainly divided into two steps: the first step is that fatty acid or fat thereof and polyamine are dehydrated at high temperature to generate imidazoline intermediate as shown in formula (A); the second step is that the imidazoline intermediate and the introduced anion are alkylated under certain conditions to generate the imidazoline amphoteric surfactant shown in the formula (B).
The product has the characteristics of good mildness, low irritation, excellent hard water resistance, pH resistance, sterilization and mildew inhibition, green degradability, good compatibility with other types of surfactants and the like, so that the product is rapidly developed in recent years, has a wide market prospect and is continuously increased in social demand. Especially in the industrial production fields of washing and nursing, cosmetics, textile industry, metal processing, petroleum industry, leather, printing and dyeing, paper making and the like, and the amphoteric surfactant has important application value and gradually becomes an important product in the amphoteric surfactant.
The oxazoline amphoteric surfactant synthesized by the two-step method at present contains 6-8% of NaCl by-products, and the chloroacetic acid and the glycolic acid remained in the system have certain irritation; meanwhile, certain inorganic salt in a product system brings certain instability and difficulty for formulation engineers to produce high value-added products.
Disclosure of Invention
In order to solve the problems in the prior art, the invention mainly aims to provide a preparation method of a salt-free imidazoline amphoteric surfactant, the preparation method has simple reaction steps and good reaction efficiency, and the prepared active agent product has lower salt content, milder performance and low irritation.
In order to achieve the above object, the present invention provides, in a first aspect, a method for preparing a salt-free imidazoline amphoteric surfactant, comprising the steps of:
(1) mixing fatty acid and polyamine for reaction to obtain imidazoline intermediate;
(2) adding an aqueous solution of an alkaline substance into the imidazoline intermediate, and preserving heat for 0.5-2 h at the temperature of 60-90 ℃ to open the imidazoline intermediate to form a chain structure;
(3) adding an alkylating reagent into the system obtained in the step (2), and reacting for 1-10 h at the temperature of 60-90 ℃, wherein the alkylating reagent is acrylic acid or acrylate;
(4) and (4) adding an aqueous solution of an alkaline substance into the system obtained in the step (3), and reacting at 60-110 ℃ to obtain a target product.
The chemical reaction equations corresponding to the preparation method of the invention are shown in formulas (I) to (IV),
on the basis of the traditional oxazoline amphoteric surfactant synthesis process, after an imidazoline intermediate is synthesized, an alkaline substance is introduced into a system in a water solution mode to be mixed with the imidazoline intermediate, so that the ring opening of the imidazoline intermediate is promoted to form a chain structure, and the active site of secondary amine is ensured; then, an alkylation reagent is used for reaction, and an alkaline system is used for hydrolysis to prepare a target product, and an alcohol byproduct is generated in the alkaline system hydrolysis process and is easy to remove.
Compared with the traditional process, the technical scheme of the invention does not use chloroacetic acid and salts thereof as alkylating reagents, and provides a new synthesis path for preparing the imidazoline amphoteric surfactant, so that the prepared target product (namely the salt-free imidazoline amphoteric surfactant) does not contain chloroacetic acid and glycolic acid, and compared with the product prepared by the traditional process, the target product prepared by the technical scheme of the invention does not contain inorganic salts such as NaCl and the like, and is a real salt-free imidazoline amphoteric surfactant.
As a preferable embodiment of the method for preparing the salt-free imidazoline amphoteric surfactant of the present invention, the alkaline substance in the step (2) and the step (4) is at least one of sodium hydroxide and potassium hydroxide.
The inventors have found through experiments that when an organic base is used as the basic additive, side reactions are likely to increase, and the purity of the product is greatly affected, so that an inorganic base is generally used as the basic additive. Further, sodium hydroxide and potassium hydroxide are selected as alkaline additives, considering that most of the surfactants on the market use sodium and potassium as neutralizing agents, and inorganic alkali is also added in the subsequent ester hydrolysis process as ester hydrolysis alkali.
In a preferred embodiment of the method for producing a salt-free imidazoline amphoteric surfactant of the present invention, the molar amount of the basic substance in the step (2) is 3 to 4% of the molar amount of the imidazoline intermediate.
In the process that the alkaline substance in the step (2) is introduced into the system to perform ring-opening reaction with the imidazoline intermediate, the addition amount of the alkaline substance needs to be strictly controlled, if the addition amount of the alkaline substance is too low, the ring opening of the imidazoline intermediate is incomplete, the subsequent reaction cannot be normally performed, and the yield of the target product is reduced; if the amount of the alkaline substance added is too high, a large amount of the alkaline substance remains, and the pH value of the system is affected.
Through a large number of experiments, the inventor finds that when the molar weight of the alkaline substance in the step (2) is 3-4% of that of the imidazoline intermediate, inorganic salt in the prepared imidazoline amphoteric surfactant is detected, the residual methanol content is lower than 0.8%, and the pH value is 9.3-10.8.
As a preferred embodiment of the preparation method of the salt-free imidazoline amphoteric surfactant, the heat preservation temperature in the step (2) is 70-80 ℃, and the heat preservation time is 1-1.5 h.
As a preferred embodiment of the method for preparing the salt-free imidazoline amphoteric surfactant of the present invention, the alkylating agent in the step (3) is at least one of acrylic acid, methyl acrylate and ethyl acrylate.
As a preferred embodiment of the method for preparing the salt-free imidazoline amphoteric surfactant of the present invention, the molar ratio of the imidazoline intermediate to the alkylating agent is: alkylating agent ═ 1: (1-1.2).
As a preferable embodiment of the preparation method of the salt-free imidazoline amphoteric surfactant, the reaction temperature in the step (3) is 75-85 ℃ and the reaction time is 5-8 h.
As a preferred embodiment of the preparation method of the salt-free imidazoline amphoteric surfactant of the present invention, the reaction conditions of the step (4) are as follows: and preserving the heat for 0.5-2 hours at the temperature of 80-100 ℃, and reacting to obtain the target product.
As a preferred embodiment of the preparation method of the salt-free imidazoline amphoteric surfactant of the present invention, the step (1) specifically comprises the following steps: mixing fatty acid and polyamine, heating to 90-110 ℃ under the protection of inert gas, vacuumizing to-0.06-0.09 MPa, reacting for 6-7 h at 180-200 ℃, and removing residual impurities in the system to obtain the imidazoline intermediate.
As a preferable embodiment of the method for preparing the salt-free imidazoline amphoteric surfactant of the present invention, in the step (1), the alkyl chain of the fatty acid contains 8 to 22 carbon atoms, the polyamine is diethylenetriamine or hydroxyethylethylenediamine, and the molar ratio of the fatty acid to the polyamine is fatty acid: and (1.1-2) a polyamine.
Compared with the prior art, the invention has the beneficial effects that:
according to the technical scheme, on the basis of the traditional oxazoline amphoteric surfactant synthesis process, after an imidazoline intermediate is synthesized, an alkaline substance is introduced into a system in a water solution mode to be mixed with the imidazoline intermediate, so that the ring opening of the imidazoline intermediate is promoted to form a chain structure, and the active site of secondary amine is ensured; then, an alkylation reagent is used for reaction, and an alkaline system is used for hydrolysis to prepare the target product. Compared with the traditional process, the technical scheme of the invention does not use chloroacetic acid and salts thereof as alkylating reagents, provides a new synthetic path for preparing the imidazoline amphoteric surfactant, and the prepared target product does not contain chloroacetic acid and glycolic acid impurities and inorganic salts such as NaCl.
Drawings
FIG. 1 is an IR spectrum of the salt-free imidazoline amphoteric surfactant prepared in example 1;
FIG. 2 is a plot of the γ -lg c of the salt-free imidazoline amphoteric surfactant prepared in example 1.
Detailed Description
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to the following specific examples.
Example 1
The preparation method of the salt-free imidazoline amphoteric surfactant comprises the following steps;
(1) adding 50g of lauric acid and 37g of hydroxyethyl ethylenediamine into a 250mL three-neck flask provided with a stirrer, a thermometer and a vacuum condenser, introducing nitrogen, heating to 100 ℃, then closing the nitrogen, vacuumizing to the vacuum degree of-0.06 MPa, heating to 190 ℃, reacting for 4 hours, continuously vacuumizing to the vacuum degree of-0.09 MPa, reacting for 2 hours, vacuumizing to the vacuum degree of less than-0.10 MPa to evaporate water generated in a system, continuously increasing the temperature to 210 ℃, keeping the temperature for 1 hour to remove the excessive hydroxyethyl ethylenediamine until no distilled component exists, stopping heating, cooling to 70 ℃, and then closing the vacuum pump to obtain 66.2g of light yellow solid, namely an imidazoline intermediate;
(2) adding the imidazoline intermediate into a 250mL three-neck flask provided with a stirrer, a thermometer and a constant pressure titration funnel, heating and dissolving, adding 0.34g of sodium hydroxide and 5g of water, and preserving heat for 1h at 75 ℃ to open the imidazoline intermediate into a chain structure;
(3) after the temperature is raised to 80 ℃, 23.5g of methyl acrylate is slowly dripped into a three-neck flask in a constant pressure titration funnel, and the temperature is kept for 5 hours after the dripping is finished;
(4) and (4) adding 24g of sodium hydroxide aqueous solution with solute mass percent of 32% into the system obtained in the step (3), reacting at 90 ℃ for 1h, vacuumizing until no component is distilled off, stopping heating, and cooling to room temperature to obtain a light yellow viscous salt-free imidazoline amphoteric surfactant product.
The IR spectrum of the salt-free imidazoline amphoteric surfactant prepared in this example is shown in FIG. 1, wherein 2925 cm and 2855cm in FIG. 1-1: C-H shock absorption peak; 1640cm-1: c is the symmetric stretching vibration peak of O; 1563 and 1405cm-1: COO-antisymmetric stretching vibration peak on the carboxylate.
The gamma-lg c curve of the salt-free imidazoline amphoteric surfactant prepared in the example is shown in fig. 2, and in fig. 2, the critical micelle concentration cmc: 0.95 mmol. L-1(ii) a Corresponding surface tension gammacmc：32.08mN·m-1。
The detection result of the salt-free imidazoline amphoteric surfactant prepared in the embodiment shows that the pH value is 9.6, the residual methanol content is less than 0.6%, and the detection result shows that inorganic salt exists.
Example 2
The preparation method of the salt-free imidazoline amphoteric surfactant comprises the following steps;
(1) adding 50g of lauric acid and 37g of hydroxyethyl ethylenediamine into a 250mL three-neck flask provided with a stirrer, a thermometer and a vacuum condenser, introducing nitrogen, heating to 110 ℃, closing the nitrogen, vacuumizing to the vacuum degree of-0.06 MPa, heating to 180 ℃, reacting for 4 hours, continuously vacuumizing to the vacuum degree of-0.09 MPa, reacting for 2 hours, vacuumizing to the vacuum degree of less than-0.10 MPa to evaporate water generated in a system, continuously increasing the temperature to 220 ℃, keeping the temperature for 1 hour to remove the excessive hydroxyethyl ethylenediamine until no distilled component exists, stopping heating, cooling to 70 ℃, and closing the vacuum pump to obtain 65.7g of light yellow solid, namely an imidazoline intermediate;
(2) adding the imidazoline intermediate into a 250mL three-neck flask provided with a stirrer, a thermometer and a constant pressure titration funnel, heating and dissolving, adding 0.34g of sodium hydroxide and 5g of water, and preserving heat for 1h at 75 ℃ to open the imidazoline intermediate into a chain structure;
(3) heating to 90 ℃, slowly dripping 29.1g of ethyl acrylate into a three-neck flask in a constant pressure titration funnel, and preserving heat for 5 hours after dripping is finished;
(4) and (3) adding 30g of sodium hydroxide aqueous solution with solute mass percent of 32% into the system obtained in the step (3), reacting at 90 ℃ for 1h, vacuumizing until no component is distilled off, stopping heating, and cooling to room temperature to obtain a light yellow viscous salt-free imidazoline amphoteric surfactant product.
The pH value of the salt-free imidazoline amphoteric surfactant product prepared in the embodiment is 10.1 through detection, and inorganic salt is detected.
Example 3
The preparation method of the salt-free imidazoline amphoteric surfactant comprises the following steps;
(1) adding 51g of lauric acid and 35g of hydroxyethyl ethylenediamine into a 250mL three-neck flask provided with a stirrer, a thermometer and a vacuum condenser, introducing nitrogen, heating to 110 ℃, closing the nitrogen, vacuumizing to the vacuum degree of-0.06 MPa, heating to 190 ℃, reacting for 5 hours, continuously vacuumizing to the vacuum degree of-0.09 MPa, reacting for 2 hours, vacuumizing to the vacuum degree of less than-0.10 MPa to evaporate water generated in a system, continuously increasing the temperature to 210 ℃, keeping the temperature for 1.5 hours to remove the excessive hydroxyethyl ethylenediamine until no distillate component exists, stopping heating, cooling to 70 ℃, and closing the vacuum pump to obtain 67g of light yellow solid, namely an imidazoline intermediate;
(2) adding the imidazoline intermediate into a 250mL three-neck flask provided with a stirrer, a thermometer and a constant pressure titration funnel, heating and dissolving, adding 0.34g of sodium hydroxide and 5g of water, and preserving heat for 1.5 hours at 70 ℃ to enable the imidazoline intermediate to form a chain structure through ring opening;
(3) after the temperature is raised to 80 ℃, 23.6g of methyl acrylate is slowly dripped into a three-neck flask in a constant pressure titration funnel, and the temperature is kept for 6 hours after the dripping is finished;
(4) and (3) adding 26g of sodium hydroxide aqueous solution with solute mass percent of 32% into the system obtained in the step (3), reacting at 95 ℃ for 1h, vacuumizing until no component is distilled off, stopping heating, and cooling to room temperature to obtain a light yellow viscous salt-free imidazoline amphoteric surfactant product.
The detection result of the salt-free imidazoline amphoteric surfactant prepared in the embodiment shows that the pH value is 9.8, the residual methanol content is less than 0.5%, and the detection result shows that inorganic salt exists.
Example 4
The preparation method of the salt-free imidazoline amphoteric surfactant comprises the following steps;
(1) adding 103g of coconut oil acid and 70g of hydroxyethyl ethylenediamine into a 500mL three-neck flask provided with a stirrer, a thermometer and a vacuum condenser, introducing nitrogen, heating to 90 ℃, closing the nitrogen, vacuumizing to the vacuum degree of-0.06 MPa, heating to 190 ℃, reacting for 5 hours, continuously vacuumizing to the vacuum degree of-0.09 MPa, reacting for 2 hours, vacuumizing to the vacuum degree of less than-0.10 MPa to evaporate water generated in the system, continuously increasing the temperature to 220 ℃, keeping the temperature for 1.5 hours to remove the excessive hydroxyethyl ethylenediamine until no distilled component exists, stopping heating, cooling to 70 ℃, and closing the vacuum pump to obtain 131.8g of light yellow waxy solid, namely an imidazoline intermediate;
(2) adding the imidazoline intermediate into a 500mL three-neck flask provided with a stirrer, a thermometer and a constant pressure titration funnel, heating and dissolving, adding 0.7g of sodium hydroxide and 10g of water, and preserving heat for 1h at 70 ℃ to open the imidazoline intermediate into a chain structure;
(3) after the temperature is raised to 80 ℃, 41.5g of methyl acrylate is slowly dripped into a three-neck flask in a constant pressure titration funnel, and the temperature is kept for 6 hours after the dripping is finished;
(4) and (4) adding 56.2g of sodium hydroxide aqueous solution with solute mass percent of 32% into the system obtained in the step (3), reacting at 95 ℃ for 1h, vacuumizing until no component is distilled off, stopping heating, and cooling to room temperature to obtain a light yellow viscous salt-free imidazoline amphoteric surfactant product.
The detection result of the salt-free imidazoline amphoteric surfactant prepared in the embodiment shows that the pH value is 10.2, the residual methanol content is less than 0.8%, and the detection result shows that inorganic salt exists.
Example 5
The preparation method of the salt-free imidazoline amphoteric surfactant comprises the following steps;
(1) adding 102.0g of lauric acid and 71.0g of hydroxyethyl ethylenediamine into a 500mL three-neck flask provided with a stirrer, a thermometer and a vacuum condenser, introducing nitrogen, heating to 100 ℃, then closing the nitrogen, firstly vacuumizing to the vacuum degree of-0.06 MPa, heating to 200 ℃, reacting for 5 hours, continuously vacuumizing to the vacuum degree of-0.09 MPa, reacting for 2 hours, vacuumizing to the vacuum degree of less than-0.10 MPa to evaporate water generated in the system, continuously increasing the temperature to 220 ℃, keeping the temperature for 1 hour to remove the excessive hydroxyethyl ethylenediamine until no distillate exists, stopping heating, cooling to 70 ℃, and then closing the vacuum pump to obtain 135.7g of light yellow waxy solid, namely an imidazoline intermediate;
(2) adding the imidazoline intermediate into a 500mL three-neck flask provided with a stirrer, a thermometer and a constant pressure titration funnel, heating and dissolving, adding 0.68g of sodium hydroxide and 12g of water, and preserving heat for 1h at 70 ℃ to open the imidazoline intermediate into a chain structure;
(3) after the temperature is raised to 90 ℃, 57.6g of ethyl acrylate is slowly dripped into a three-neck flask in a constant pressure titration funnel, and the temperature is kept for 6 hours after the dripping is finished;
(4) and (4) adding 45g of sodium hydroxide aqueous solution with solute mass percent of 32% into the system obtained in the step (3), reacting for 0.5h at 95 ℃, vacuumizing until no component is distilled off, stopping heating, and cooling to room temperature to obtain a light yellow viscous salt-free imidazoline amphoteric surfactant product.
The pH value of the salt-free imidazoline amphoteric surfactant product prepared in the embodiment is 9.3 through detection, and inorganic salt is detected.
Example 6
This example is prepared substantially identically to example 1, except that: in this example, step (2), 0.25g of sodium hydroxide and 5g of water were added.
After the salt-free imidazoline amphoteric surfactant product prepared in the embodiment is placed for a period of time, insoluble precipitates are separated out, and the separated-out substances are imidazoline intermediates, which are caused by low reaction conversion rate due to incomplete hydrolysis of the imidazoline intermediates.
Example 7
This example is prepared substantially identically to example 1, except that: in this example, step (2), 0.5g of sodium hydroxide and 5g of water were added.
The viscosity of the system is increased after the salt-free imidazoline amphoteric surfactant prepared in the embodiment is added into the acrylic acid derivative, because excessive sodium hydroxide can hydrolyze part of the acrylic acid derivative into acrylic acid in advance, so that the viscosity of the system is rapidly increased, and excessive sodium hydroxide can make the system too strong in alkalinity and easily activate the terminal hydroxyl of an imidazoline intermediate, so that side reactions of the system are increased, the purity of the product is influenced, and the conversion rate of the system reaction is low. The product prepared in this example was tested to have a pH of 11.3 and was found to be free of inorganic salts.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. The preparation method of the salt-free imidazoline amphoteric surfactant is characterized by comprising the following steps:
(1) mixing fatty acid and polyamine for reaction to obtain imidazoline intermediate;
(2) adding an aqueous solution of an alkaline substance into the imidazoline intermediate, and preserving heat for 0.5-2 h at the temperature of 60-90 ℃ to open the imidazoline intermediate to form a chain structure;
(3) adding an alkylating reagent into the system obtained in the step (2), and reacting for 1-10 h at the temperature of 60-90 ℃, wherein the alkylating reagent is acrylic acid or acrylate;
(4) and (4) adding an aqueous solution of an alkaline substance into the system obtained in the step (3), and reacting at 60-110 ℃ to obtain a target product.
2. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the alkaline substance in the step (2) and the step (4) is at least one of sodium hydroxide and potassium hydroxide.
3. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the molar amount of the basic substance in the step (2) is 3 to 4% of the molar amount of the imidazoline intermediate.
4. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the temperature of the step (2) is 70-80 ℃ and the holding time is 1-1.5 h.
5. The method for preparing the salt-free imidazoline amphoteric surfactant of claim 1, wherein the alkylating agent in the step (3) is at least one of acrylic acid, methyl acrylate and ethyl acrylate.
6. The method of preparing the salt-free imidazoline amphoteric surfactant of claim 1, wherein the molar ratio of the imidazoline intermediate to the alkylating agent is imidazoline intermediate: alkylating agent ═ 1: (1-1.2).
7. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the reaction temperature in the step (3) is 80-90 ℃ and the reaction time is 5-8 h.
8. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the reaction conditions of the step (4) are as follows: and preserving the heat for 0.5-2 hours at the temperature of 80-100 ℃, and reacting to obtain the target product.
9. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the step (1) comprises the following steps: mixing fatty acid and polyamine, heating to 90-110 ℃ under the protection of inert gas, vacuumizing to-0.06-0.09 MPa, reacting for 6-7 h at 180-200 ℃, and removing residual impurities in the system to obtain the imidazoline intermediate.
10. The method for preparing the salt-free imidazoline amphoteric surfactant according to claim 1, wherein the alkyl chain of the fatty acid in the step (1) contains 8-22 carbon atoms, the polyamine is diethylenetriamine or hydroxyethylethylenediamine, and the molar ratio of the fatty acid to the polyamine is fatty acid: and (1.1-2) a polyamine.
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