CN112300016B - Alkyl betaines and process for their preparation - Google Patents
Alkyl betaines and process for their preparation Download PDFInfo
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Abstract
The application relates to the technical field of betaine, and particularly discloses a preparation method of alkyl betaine. The preparation method comprises the following steps: step 1), mixing chloroacetic acid, sodium hydroxide and water, heating while stirring, wherein the heating temperature is less than 60 ℃, and uniformly stirring to form a premix; step 2), adding dodeca/tetradecyl tertiary amine into the premix to form a mixture; step 3), adding a catalyst into the mixture, then adjusting the temperature to 40-60 ℃, reacting for 1-3h, and taking the reacted mixture to obtain the alkyl betaine; the catalyst in the step 2) is stannous octoate and monobutyl tin oxide. The preparation method has the advantage of further improving the production efficiency of the alkyl betaine.
Description
Technical Field
The application relates to the technical field of betaine, in particular to alkyl betaine and a preparation method thereof.
Background
Betaine is a quaternary ammonium compound found in various organisms including bacteria, hemophilus, marine invertebrates, plants, mammals, etc., and many derivatives can be obtained by subjecting betaine to a certain chemical treatment, for example, when the methyl group of betaine is substituted with other substituent, various polyalkyl aromatic betaines or alkylamidopropyl betaines can be obtained.
The alkyl betaine serving as one of the common betaines can be compatible with various dyes, surfactants and cosmetic raw materials, has excellent stability under acidic and alkaline conditions, is good in compatibility, can remarkably improve the softness, conditioning and low-temperature stability of washing products when being compatible for use, is low in skin durability and good in biodegradability, has excellent decontamination, sterilization, softness, antistatic property, decontamination, sterilization, antirust property and the like, and has wide application prospects.
At present, the alkyl betaine type zwitterionic surfactant is prepared by reacting long-chain alkyl dimethyl tertiary amine or long-chain amidopropyl dimethyl tertiary amine with chloroacetic acid at 80-100 ℃ for 3-8 hours by adopting the quaternization of aliphatic tertiary amine in the market.
In view of the above-mentioned related technologies, the inventors believe that there is room for improvement in the processes for preparing alkyl betaines in the related technologies, which require higher temperature and longer reaction time, slower reaction rate and higher energy consumption, resulting in lower production efficiency of alkyl betaines, lower active substance content and higher preparation cost.
Disclosure of Invention
In order to further improve the production efficiency of the alkyl betaine, the application provides the alkyl betaine and a preparation method thereof.
In a first aspect, the present application provides a method for preparing alkyl betaine, which adopts the following technical scheme:
a preparation method of alkyl betaine comprises the following steps:
step 1), mixing chloroacetic acid, sodium hydroxide and water, stirring and reacting, controlling the reaction temperature to be less than 60 ℃, and uniformly stirring to form a premix;
step 2), adding dodeca/tetradecyl tertiary amine into the premix to form a mixture;
step 3), adding a catalyst into the mixture, then adjusting the temperature to 40-60 ℃, reacting for 1-3h, and taking the reacted mixture to obtain alkyl betaine;
the catalyst in the step 3) is stannous octoate and monobutyl tin oxide.
By adopting the technical scheme, the catalyst has good activity by controlling specific temperature and specific reaction time, so that the forward reaction rate of the reaction is better promoted, the temperature and time required by the reaction are reduced, the energy consumption is reduced, the production efficiency is further improved, and the production cost is reduced as much as possible.
By controlling the neutralization reaction temperature, the neutralization reaction of chloroacetic acid and sodium hydroxide is a violent exothermic reaction, and the temperature is controlled in a lower range, so that the neutralization reaction is promoted better, and the neutralization effect is better.
By controlling the temperature of the catalytic reaction and the reaction time, the method is favorable for promoting the reaction, so that the forward reaction rate is higher, the side reaction and the reverse reaction are favorably inhibited better, the generation of byproducts is reduced, and meanwhile, the cost can be saved while the production efficiency is improved.
By adopting the dodecatertiary amine/tetradecyl tertiary amine, the dodecatertiary amine/tetradecyl tertiary amine is an excellent intermediate for preparing the surfactant, has higher biodegradability and lower irritation to skin.
By adopting stannous octoate and monobutyl tin oxide as catalysts, the stannous octoate and monobutyl tin oxide cooperate with each other to catalyze the reaction of neutralization products sodium chloroacetate and dodeca/tetradecyl tertiary amine, so that the catalytic effect is better, the reaction temperature is reduced, the reaction time is shortened, higher reaction temperature and long-time reaction are not needed, higher conversion rate is obtained, the production cost is saved, reactants are easier to be converted into target products when the stannous octoate and monobutyl tin oxide cooperate with each other for use, the reaction is more complete, fewer by-products are produced, the production efficiency of alkyl betaine is improved, the monobutyl tin oxide and the stannous octoate have synergistic effect, the catalytic capability of the stannous octoate is stronger, the reaction catalytic effect can be further improved, the forward reaction rate of the reaction is improved, the side reaction and the reverse reaction can be effectively inhibited, the production efficiency is improved better, and the production cost is reduced.
Preferably, in the step 1), the reaction temperature is controlled to be 40-50 ℃.
By adopting the technical scheme, the temperature of the neutralization reaction is controlled to be 40-50 ℃, and the neutralization reaction is more complete because the chloroacetic acid and the sodium hydroxide are in violent exothermic reaction, and the chloroacetic acid is easy to hydrolyze at high temperature and is controlled at a lower reaction temperature, so that the quaternization reaction is facilitated to be more complete.
Preferably, the mass of the catalyst added is 4% to 8% of the mass of the premix.
By adopting the technical scheme, the adding quality of the catalyst is controlled to be 4% -8% of the quality of the premix, so that the catalyst can better play a catalytic role, the reaction rate is improved, the reaction time of the mixture is shortened, the conversion rate is further improved, the generation of impurities after the reaction is reduced, and the production cost is saved to a certain extent.
Preferably, in the step 3), molybdate is also added when the catalyst is added.
Through adopting above-mentioned technical scheme, through adopting the molybdate, through the cooperation of molybdate and stannous octoate, monobutyl tin oxide, the molybdate can further promote stannous octoate and monobutyl tin oxide synergistic effect, is favorable to strengthening stannous octoate and monobutyl tin oxide's catalytic effect better for the forward reaction rate of reaction is higher, thereby is favorable to reducing reaction time better, improves production efficiency.
Preferably, the addition mass of the molybdate is 0.2 to 0.4 percent of the mass of the catalyst.
By adopting the technical scheme, the addition amount of the molybdate is controlled to be 0.2-0.4% of the mass of the catalyst, so that the catalytic action of the catalyst is further promoted, the side reaction and the reverse reaction are further reduced, and the generation of impurities after the reaction is reduced, thereby saving the production cost and being beneficial to improving the catalytic efficiency.
Preferably, the molybdate is one or a compound of more of ammonium molybdate, sodium molybdate, potassium molybdate and lithium molybdate.
By adopting the technical scheme, one or more of ammonium molybdate, sodium molybdate, potassium molybdate and lithium molybdate are compounded to be used as the auxiliary catalyst, so that the stability is better, the catalytic effect of the catalyst is better, and the forward reaction rate of the reaction is higher.
Preferably, in the step 1), the mass ratio of the chloroacetic acid to the sodium hydroxide is 1:4-6.
By adopting the technical scheme, the mass ratio of the chloroacetic acid to the sodium hydroxide is controlled to be 1:4-6, which is beneficial to the complete reaction of reactants, thereby being beneficial to the complete proceeding of the quaternization reaction, and leading the yield and the purity of the quaternization reaction to be higher.
Preferably, in the step 3), the temperature is adjusted to 45-55 ℃.
By adopting the technical scheme, the reaction temperature is controlled, so that the reaction rate is favorably accelerated, the reaction time is shorter, the production rate is better improved, and the production cost is reduced.
Preferably, in step 2), the dodecyltetradecylamine is vacuum drawn into the premix.
By adopting the technical scheme, the dodecat/tetradecyl tertiary amine is pumped into the premix in a vacuum manner, so that oxygen is not easy to be pumped into the premix, and water vapor in the premix is easier to be discharged along with vacuumized airflow, thereby being beneficial to better reducing the occurrence of side reactions, inhibiting the reverse reaction to a certain extent and improving the yield.
In summary, the present application has the following beneficial effects:
1. because this application has adopted stannous octoate and monobutyl tin oxide as the catalyst, because stannous octoate is done and monobutyl tin oxide both cooperate the catalysis neutralization product sodium chloroacetate and the catalytic effect of the reaction of dodeca/tetradecyl tertiary amine preferred with monobutyl tin oxide, be favorable to reducing the temperature of reaction and shorten the time of reaction simultaneously, and reactant is changeed into the target product more easily when both cooperate and use to make the reaction more complete, the accessory substance that produces is less, and then improves the production efficiency of alkyl betaine.
2. Preferentially adopt stannous octoate and monobutyl tin oxide as the catalyst in this application, monobutyl tin oxide has synergistic effect with stannous octoate for stannous octoate's catalytic capability is stronger, can further promote reaction catalytic effect, thereby improves the forward reaction rate of reaction, can comparatively effectual suppression side reaction and reverse reaction, and then is favorable to promoting production efficiency better, reduces the cost of production.
3. Preferentially adopt the molybdate in this application, through the cooperation of molybdate and stannous octoate, monobutyl tin oxide, be favorable to strengthening stannous octoate and monobutyl tin oxide's catalytic effect better for the forward reaction rate of reaction is higher, thereby is favorable to reducing reaction time better, improves production efficiency.
Detailed Description
The present application will be described in further detail with reference to examples.
The information on the source of each raw material component in the following examples and comparative examples is shown in Table 1.
TABLE 1
Examples 1 to 3
An alkyl betaine comprising the following components:
chloroacetic acid, sodium hydroxide, dodecyl/tetradecyl tertiary amine, a catalyst and water.
The catalyst is stannous octoate and monobutyl tin oxide.
In examples 1-3, the amounts (in Kg) of the ingredients added are specified in Table 2.
TABLE 2
| Example 1 | Example 2 | Example 3 | |
| Chloroacetic acid | 0.1 | 0.1 | 0.1 |
| Sodium hydroxide (NaOH) | 0.4 | 0.5 | 0.6 |
| Dodecyl/tetradecyl tertiary amine | 22 | 25 | 28 |
| Stannous octoate | 2 | 3 | 4 |
| Monobutyl tin oxide | 2 | 3 | 4 |
| Water (I) | 77.5 | 74.4 | 71.3 |
In examples 1 to 3, a method for preparing an alkyl betaine, comprising the steps of:
step 1), adding water into a reaction kettle at a stirring speed of 60r/min, adding chloroacetic acid into the reaction kettle in a manual feeding mode while stirring, adding sodium hydroxide into a dissolution head tank for dissolution in the manual feeding mode, slowly adding the dissolved sodium hydroxide into the reaction kettle at a speed of 20g/min for neutralization reaction, starting circulating cooling water to control the neutralization reaction temperature at 45 ℃, stirring for 20 minutes, and uniformly stirring to form a premix;
step 2), pumping the dodecat/tetradecyl tertiary amine into a reaction kettle in vacuum, adding stannous octoate and monobutyl tin oxide, rotating at 60r/min, and stirring for 15 minutes to form a mixture;
and 3), heating the mixture in the reaction kettle to 50 ℃, reacting for 1h, and cooling to room temperature to obtain the alkyl betaine.
Example 4
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
the neutralization reaction temperature in step 1) was 40 ℃.
Example 5
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
the neutralization reaction temperature in the step 1) is 50 DEG C
Examples 6 to 10
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
in step 3), the reaction temperature and reaction time are detailed in Table 3.
TABLE 3
| Example 6 | Example 7 | Example 8 | Example 9 | Example 10 | |
| Reaction temperature/. Degree.C | 40 | 45 | 50 | 55 | 60 |
| Reaction time/h | 1.5 | 1 | 2 | 3 | 3 |
Examples 11 to 13
An alkyl betaine which differs from example 2 only in that:
the alkyl betaine also comprises the following components: and (4) molybdate.
The molybdate is ammonium molybdate.
In examples 11 to 13, the amounts (in Kg) of the respective components charged are specified in Table 4.
TABLE 4
| Example 11 | Example 11 | Example 13 | |
| Chloroacetic acid | 0.1 | 0.1 | 0.1 |
| Sodium hydroxide (NaOH) | 0.5 | 0.5 | 0.5 |
| Dodecyl/tetradecyl tertiary amine | 25 | 25 | 25 |
| Stannous octoate | 3 | 3 | 3 |
| Monobutyl tin oxide | 3 | 3 | 3 |
| Water (W) | 74.4 | 74.4 | 74.4 |
| Ammonium molybdate | 0.12 | 0.18 | 0.24 |
And (3) adding ammonium molybdate, stannous octoate and monobutyl tin oxide into the reaction kettle in the step 2), and uniformly stirring.
Comparative example 1
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
in the step 2), equivalent water is adopted to replace stannous octoate and monobutyl tin oxide.
Comparative example 2
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
in step 2), the same amount of water is used instead of monobutyltin oxide.
Comparative example 3
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
in the step 2), equivalent water is adopted to replace stannous octoate.
Comparative example 4
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
in the step 2), equivalent copper stearate is adopted to replace stannous octoate and monobutyl tin oxide.
Comparative example 5
An alkyl betaine which differs from example 2 only in that:
the preparation method of the alkyl betaine comprises the following steps:
in the step 2), equivalent hydroquinone is adopted to replace stannous octoate and monobutyl tin oxide.
Performance detection
The physicochemical indexes of the alkyl betaine prepared in the above examples are detected and recorded according to light industry standard QB/T2344-2012, namely amphoteric surfactant fatty alkyl dimethyl betaine, and the detected pH value is 7.0-8.0, the content of sodium chloride is less than 7.5%, the color is less than 80%, and chloroacetic acid is less than 20mg/kg, which all meet the standard.
Experiment 1
The active substance content as well as the unreacted amine content of the alkyl betaines prepared in the examples and comparative examples were tested according to the light industry standard QB/T2344-2012 "amphoteric surfactant fatty alkyl dimethyl betaine".
The assay data for experiment 1 are detailed in table 5.
TABLE 5
According to the comparison of the data of comparative example 2 and comparative example 1 in table 5, the content of active substances is increased to a certain extent and the content of unreacted amine is reduced to a certain extent by adding stannous octoate alone as a catalyst, and the change is not obvious, which proves that adding stannous octoate alone as a catalyst has no obvious negative effect on the reaction between a neutralization product and dodecyl/tetradecyl tertiary amine.
As can be seen from comparison of the data of comparative example 3 with that of comparative example 1 in Table 5, the addition of monobutyltin oxide alone as a catalyst did not significantly change the active material content from the content of unreacted amine, demonstrating that the addition of monobutyltin oxide alone had no significant negative effect on the rate of reaction between the neutralized product and dodeca-/tetradecyltriethylamine within a specific reaction time.
According to the comparison of the data of the example 2 and the comparative examples 2 and 3 in the table 5, the content of the active substances is greatly improved by adding the stannous octoate and the monobutyl tin oxide, and meanwhile, the content of the unreacted amine is obviously reduced to a certain extent, so that the coordination of the stannous octoate and the monobutyl tin oxide as the catalyst can catalyze the reaction of the neutralization product sodium chloroacetate and the dodeca/tetradecyl tertiary amine to a large extent, which is beneficial to reducing the reaction temperature and shortening the reaction time, so that higher reaction temperature and longer reaction time are not needed, higher conversion rate is obtained, energy consumption is reduced, the production cost can be greatly reduced to a certain extent, resources are saved, and meanwhile, higher yield is achieved.
According to the comparison of the data of comparative examples 4 and 5 with those of examples 2 and 1 in table 5, the content of active substances is increased to a certain extent, the content of unreacted amines is decreased to a certain extent, and the change is not large, so that the addition of the conventional catalyst can catalyze the reaction of sodium chloroacetate and dodecatetradecyltriethylamine, which are neutralization products, to a certain extent, but the catalytic effect is relatively general, and the combination of stannous octoate and monobutyltin oxide as the catalyst has a better catalytic effect, can increase the reaction rate to a large extent, and thus has a higher conversion rate at a lower reaction time and reaction temperature.
According to the comparison of the data of examples 4-5 and example 2 in table 5, the content of unreacted amine is slightly reduced by controlling the temperature of neutralization reaction, thereby showing that the neutralization reaction can be more complete by reducing the temperature of neutralization reaction in a certain range, which is beneficial to promoting the reaction rate of the neutralized product and the dodeca/tetradecyltriethylamine, so that the reaction is more complete, and the conversion rate is further improved.
According to the comparison of the data of the examples 6-10 and the example 2 in the table 5, the reaction time and the reaction temperature of the neutralization product sodium chloroacetate and the dodecat/tetradecyl tertiary amine are controlled, the reaction temperature is 45-50 ℃, the reaction time is 1h, and the conversion rate is higher, so that the reaction temperature can be reduced to a greater extent while the reaction time is shortened by adding the stannous octoate and the monobutyl tin oxide to be matched as the catalyst, and the reaction temperature and the reaction time have no obvious negative influence on the catalytic effect of the reaction product in a certain range.
According to the comparison of the data of examples 1 to 3 in table 5, the neutralization reaction is performed at a lower temperature by controlling the temperature of the neutralization reaction, so that the hydrolysis of chloroacetic acid at a high temperature is reduced, the neutralization reaction is more complete, and the conversion rate of the reaction is improved by controlling the addition mass ratio of chloroacetic acid to sodium hydroxide, so that the content of active substances is improved, the content of amine to be reacted is reduced, and the yield of the alkyl betaine is improved.
As can be seen from the comparison of the data of examples 11-13 and example 2 in table 5, the addition of ammonium molybdate facilitates the promotion of the catalytic effect of the catalyst, so that the reaction rate is faster in the same time, and the content of active substances is increased, thereby facilitating the production of alkyl betaine with higher yield at lower temperature and in shorter time; by controlling the addition amount of ammonium molybdate, the method is also favorable for better playing the promotion effect of the ammonium molybdate on the catalytic effect of the catalyst, and further reducing side reactions and reverse reactions, thereby being favorable for better reducing the content of unreacted amine.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (5)
1. A preparation method of alkyl betaine is characterized by comprising the following steps: the method comprises the following steps:
step 1), mixing chloroacetic acid, sodium hydroxide and water, stirring and reacting, controlling the reaction temperature to be less than 60 ℃, and uniformly stirring to form a premix;
step 2), adding dodeca/tetradecyl tertiary amine into the premix to form a mixture;
step 3), adding a catalyst into the mixture, then adjusting the temperature to 40-60 ℃, reacting for 1-3h, and taking the reacted mixture to obtain alkyl betaine;
the catalyst in the step 3) is stannous octoate and monobutyl tin oxide, and molybdate is added when the catalyst is added, wherein the addition mass of the molybdate is 0.2-0.4% of the mass of the catalyst;
in the step 1), the mass ratio of the chloroacetic acid to the sodium hydroxide is 1:4-6;
the adding mass of the catalyst is 4-8% of the mass of the mixture.
2. The method for producing an alkyl betaine according to claim 1, wherein: in the step 1), the reaction temperature is controlled to be 40-50 ℃.
3. The method for producing an alkyl betaine according to claim 1, wherein: the molybdate is one or a compound of more of ammonium molybdate, sodium molybdate, potassium molybdate and lithium molybdate.
4. The method for producing an alkyl betaine according to any one of claims 1 to 2, wherein: in the step 3), the temperature is adjusted to 45-55 ℃.
5. The method for producing an alkyl betaine according to any one of claims 1 to 2, wherein: in said step 2), the dodecyltetradecanoic amine is vacuum pumped into the premix.
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| US7314951B2 (en) * | 2003-09-25 | 2008-01-01 | Baker Hughes Incorporated | Process and composition for lower toxicity quaternary ammonium compounds |
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