CN116162943A - Preparation method of trimethyl ethyl ammonium hydroxide and quaternary ammonium base aqueous solution prepared by preparation method - Google Patents
Preparation method of trimethyl ethyl ammonium hydroxide and quaternary ammonium base aqueous solution prepared by preparation method Download PDFInfo
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- CN116162943A CN116162943A CN202310110052.3A CN202310110052A CN116162943A CN 116162943 A CN116162943 A CN 116162943A CN 202310110052 A CN202310110052 A CN 202310110052A CN 116162943 A CN116162943 A CN 116162943A
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Abstract
The application discloses a preparation method of trimethyl ethyl ammonium hydroxide and a quaternary ammonium base aqueous solution prepared by the preparation method, which comprises the following steps: s1 quaternization: introducing trimethylamine into a reaction solvent, sealing, stirring, introducing chloroethane, heating to not lower than 60 ℃ for reaction for not less than 3 hours, and recovering a product to prepare trimethyl ethyl ammonium chloride; s2, electrolysis: preparing aqueous solution by trimethyl ethyl ammonium chloride, adding the aqueous solution into an electrolysis device, and electrolyzing to obtain trimethyl ethyl ammonium cation, wherein the trimethyl ethyl ammonium cation enters a cathode chamber through a cation membrane and combines with hydroxide ions generated by a cathode to form trimethyl ethyl ammonium hydroxide, so as to prepare quaternary ammonium alkaline aqueous solution. The preparation method of the trimethyl ethyl ammonium hydroxide has the advantage of improving the product quality.
Description
Technical Field
The application relates to the technical field of high-purity quaternary ammonium base wet electronic chemical production, in particular to a preparation method of trimethyl ethyl ammonium hydroxide and a quaternary ammonium base aqueous solution prepared by the same.
Background
The quaternary ammonium base used as the etchant has the advantages of high etching rate, good crystal orientation selectivity, low toxicity and the like, and is widely used in the fields of wet electronic chemicals such as etching and cleaning of semiconductor integrated circuits along with the high-speed development of electronic information technology. Among them, trimethyl ethyl ammonium hydroxide has great application potential in the field of wet electronic chemicals.
The current common production method of trimethyl ethyl ammonium hydroxide is to react trimethyl amine with halogenated ethane to generate trimethyl ethyl ammonium halide, then exchange ions with ion exchange resin to exchange halogen ions into hydroxyl ions, and prepare trimethyl ethyl ammonium hydroxide. In the technical scheme, ion exchange resin is needed to be used, the ion exchange resin is needed to be soaked by acid and alkali in sequence, and then a large amount of water is used for leaching, so that the pretreatment of the ion exchange resin is completed. A large amount of wastewater is generated, and the operation is complex and tedious, which is not beneficial to industrial production.
In view of the above-mentioned related art, the inventors believe that the ion exchange resin contains a certain amount of impurities such as metal ions, and the ion exchange is difficult to complete, so that the trimethyl ethyl ammonium hydroxide product contains a certain amount of impurities such as metal ions and chloride ions, which affects the product quality.
Disclosure of Invention
In order to improve the quality of the trimethyl ethyl ammonium hydroxide, the application provides a preparation method of the trimethyl ethyl ammonium hydroxide and a quaternary ammonium base aqueous solution prepared by the preparation method.
In a first aspect, the present application provides a preparation method of trimethyl ethyl ammonium hydroxide, which adopts the following technical scheme:
a method for preparing trimethyl ethyl ammonium hydroxide, comprising the following steps:
s1 quaternization: introducing trimethylamine into a reaction solvent, sealing, stirring, introducing chloroethane, heating to not lower than 60 ℃ for reaction for not less than 3 hours, and recovering a product to prepare trimethyl ethyl ammonium chloride;
s2, electrolysis: preparing aqueous solution by trimethyl ethyl ammonium chloride, adding the aqueous solution into an electrolysis device, and electrolyzing to obtain trimethyl ethyl ammonium cation, wherein the trimethyl ethyl ammonium cation enters a cathode chamber through a cation membrane and combines with hydroxide ions generated by a cathode to form trimethyl ethyl ammonium hydroxide, so as to prepare quaternary ammonium alkaline aqueous solution.
By adopting the technical scheme, the trimethyl ethyl ammonium hydroxide is prepared by an electrolytic method, so that impurities such as metal ions, chloride ions and the like in the ion exchange resin in the resin ion exchange method are prevented from entering the product, and the product purity is higher. In the quaternization reaction process, trimethylamine is firstly dissolved into a reaction solvent, and then chloroethane is introduced, so that the chloroethane can timely react with the trimethylamine, thereby being beneficial to avoiding hydrochloric acid formation caused by local excessive chloroethane hydrolysis, being beneficial to avoiding trimethylamine hydrochloride formation in the quaternization reaction process, being beneficial to reducing the concentration of the trimethylamine in a cathode chamber of electrolysis equipment, being beneficial to reducing the corrosion and damage of the trimethylamine to an ion exchange membrane and an electrode plate, being beneficial to reducing impurities and being beneficial to improving the product quality.
Preferably, the reaction solvent is a mixed solvent of acetonitrile and ethanol, and the weight ratio of the ethanol to the acetonitrile is (0.01-0.08): 1, a step of; more preferably, the weight ratio of the ethanol to the acetonitrile is (0.03-0.06): 1.
by adopting the technical scheme, the chloroethane is hydrolyzed to form hydrochloric acid and ethanol, the mixed solvent of ethanol and acetonitrile is used, and a small amount of ethanol is added to inhibit the chloroethane from being hydrolyzed, so that the quality of products is improved. Acetonitrile is used as an aprotic solvent and has a certain promotion effect on the quaternization reaction, and when the ethanol content in the solvent is too high, the reaction rate of the quaternization reaction can be reduced, unreacted materials are easily contained in the product, and the quality of the product is adversely affected. Therefore, the ethanol ratio in the mixed solvent cannot be too low nor too high.
Preferably, the step S1 of recovering the product comprises the steps of: cooling the reaction solution to not higher than 35 ℃, carrying out suction filtration and vacuum drying to obtain trimethyl ethyl ammonium chloride; the vacuum drying pressure is less than or equal to-0.08 MPa, the drying temperature is 60-100 ℃, and the drying time is not less than 180min.
By adopting the technical scheme, the impurities such as ethanol, trimethylamine and the like remained in the quaternization reaction product are removed by vacuum drying, and the product quality is improved.
Preferably, the ratio of the amounts of the substances of trimethylamine to chloroethane is 1: (0.98-1).
By adopting the technical scheme, the trimethylamine is slightly excessive, so that the formation of hydrogen chloride by the hydrolysis of chloroethane is avoided, and the reduction of impurities is facilitated; and excessive trimethylamine can be removed by vacuum drying and other modes, thereby being beneficial to improving the product quality.
Preferably, the ratio of the amount of trimethylamine to acetonitrile is 1: (4-10).
By adopting the technical scheme, the single kettle yield can be improved by adopting the proper reaction solvent dosage on the basis of ensuring the reaction rate, thereby being beneficial to improving the production efficiency and reducing the production cost.
Preferably, the electrolysis equipment used in the electrolysis in the step S2 comprises an anode chamber, an absorption chamber, a raw material chamber and a cathode chamber which are sequentially adjacent; an anode plate is arranged in the anode chamber, a cathode plate is arranged in the cathode chamber, and the anode plate is connected with the cathode plate through a power supply; the anode chamber is communicated with the absorption chamber through a first cationic membrane, the absorption chamber is communicated with the raw material chamber through an anionic membrane, and the raw material chamber is communicated with the cathode chamber through a second cationic membrane; step S2 is to prepare aqueous solution of trimethyl ethyl ammonium chloride, add the aqueous solution into a raw material chamber, electrolyze, make trimethyl ethyl ammonium cation enter the cathode chamber through a second cation membrane, combine with hydroxide ion generated by the cathode, form trimethyl ethyl ammonium hydroxide, and prepare quaternary ammonium alkali aqueous solution.
By adopting the technical scheme, trimethyl ethyl ammonium hydroxide is produced by a four-chamber three-membrane electrolysis method, hydrogen is separated from a cathode to form hydroxyl, and trimethyl ethyl ammonium cations enter a cathode chamber through a second cation membrane and are combined with hydroxyl ions to form trimethyl ethyl ammonium hydroxide; chlorine ions enter the absorption chamber through the anion membrane, oxygen is separated from the anode to form hydrogen ions, and the hydrogen ions enter the absorption chamber through the first cation membrane to form hydrochloric acid. And the trimethyl ethyl ammonium hydroxide is produced by a four-chamber three-membrane electrolysis method, which is beneficial to improving the product quality.
Preferably, water is added to both the anode chamber and the cathode chamber of the step S2, and urea is added to the absorption chamber.
By adopting the technical scheme, the concentration of chloride ions in the absorption chamber is higher, and urea is added into the absorption chamber, so that the urea has a certain reducibility, is favorable for preventing the formation of chlorine gas, is favorable for preventing the ionic membrane from being oxidized, and is favorable for improving the product quality.
Preferably, the mass concentration of urea in the absorption chamber of step S2 is 0.5-2%.
By adopting the technical scheme, the urea with proper concentration is adopted, which is helpful for improving the product quality.
In a second aspect, the present application provides an aqueous quaternary ammonium base solution, which adopts the following technical scheme:
an aqueous quaternary ammonium base is prepared by the preparation method of the trimethyl ethyl ammonium hydroxide.
By adopting the technical scheme, the trimethyl ethyl ammonium hydroxide aqueous solution is produced by the preparation method of the trimethyl ethyl ammonium hydroxide disclosed by the application, which is beneficial to improving the product quality and meeting the requirements of wet electronic chemicals better.
In summary, the present application includes at least one of the following beneficial technical effects:
1. firstly, trimethylamine reacts with chloroethane to prepare trimethyl ethyl ammonium chloride, and then the trimethyl ethyl ammonium chloride is prepared by electrolysis; in the quaternization reaction process, the product quality can be improved by the combination of a mode of dissolving trimethylamine and then adding chloroethane and an electrolysis process;
2. according to the method, the mixed solvent containing ethanol and acetonitrile is used, the ethanol and acetonitrile are properly proportioned, and the hydrolysis of chloroethane can be inhibited under the combined action of a specific feeding sequence, so that the impurities in the product are reduced, and the quality of the product is improved;
3. the urea is added in the electrolysis process, so that oxidation is prevented, impurities in a product are reduced, and the product quality is improved.
Drawings
Fig. 1 is a schematic view of an electrolytic apparatus used in the present application.
Reference numerals: 1. an anode chamber; 2. an absorption chamber; 3. a raw material chamber; 4. a cathode chamber; 5. an anode plate; 6. a cathode plate; 7. a first cationic membrane; 8. an anionic membrane; 9. and a second cationic membrane.
Detailed Description
Compared with other halogenated ethane such as bromoethane, the price of chloroethane is lower, so trimethyl ethyl ammonium chloride is generally prepared by quaternization reaction of trimethylamine and chloroethane, and then trimethyl ethyl ammonium hydroxide is prepared by trimethyl ethyl ammonium chloride. The trimethyl ethyl ammonium hydroxide is produced by an ion exchange method, a certain amount of metal ions and halogen ions remain in the product, the quality of the product is affected, and the product is difficult to meet the quality requirement of wet electronic chemicals. In the quaternization reaction process, chloroethane is easy to hydrolyze to form hydrogen chloride, the hydrogen chloride reacts with trimethylamine to directly generate trimethylamine hydrochloride, and in the electrolysis process, trimethylamine salt cations enter a cathode chamber (product chamber) through a cation membrane; on the one hand, the purity of the product is affected; on the other hand, because hydrogen is separated from the cathode chamber to form hydroxyl, under the strong alkaline environment condition of the cathode chamber, trimethylamine salt cations exist in the form of trimethylamine, more free amine exists in the product, certain corrosion and damage are caused to an ion exchange membrane and an electrode in the electrolysis equipment, impurities such as metal ions on an electrode plate enter the product, and a small amount of impurities such as chloride ions in a raw material chamber enter the product after the ion membrane is damaged, so that the product quality is affected. Based on the above technical background, the present application proposes a technical scheme of trimethyl ethyl ammonium hydroxide capable of improving product quality, and the technical scheme is specifically described by the following specific embodiments.
The water used in the examples below was deionized water with a conductivity of no more than 10 mus/cm. The power supply in the electrolysis process is a direct current power supply. The mass concentration of the trimethyl ethyl ammonium chloride in the raw material chamber in the electrolysis process is not more than 18%, preferably 10-18%. In the electrolysis process, titrating the chloride ion concentration in the raw material chamber by using silver nitrate, measuring the concentration of trimethyl ethyl ammonium chloride through conversion, and tracking the concentration of trimethyl ethyl ammonium chloride in the raw material chamber in the electrolysis process; and (2) supplementing the trimethyl ethyl ammonium chloride prepared in the step S1 into the raw material chamber in the electrolysis process according to the concentration change condition of the trimethyl ethyl ammonium chloride in the raw material chamber, so that the mass concentration of the trimethyl ethyl ammonium chloride in the raw material chamber is kept at 10-18%. The following examples use the same set of electrolysis apparatus. Before the power supply is started to electrolyze, the anode chamber, the raw material chamber and the cathode chamber are all filled with water. In each of the following experiments, new cationic and anionic membranes (ion membranes detachably mounted in the electrolysis apparatus) were used.
The present application is described in further detail below with reference to the accompanying drawings.
Examples
Example 1: the preparation method of the trimethyl ethyl ammonium hydroxide comprises the following steps:
s1 quaternization: 1642g of acetonitrile was added to a 5L high-pressure magnetic-seal reaction vessel, and the vessel was sealed and stirred at a rotation speed of 150 rpm. 236g of trimethylamine are introduced into acetonitrile from below the liquid surface by means of a pressure reducing valve and stirred for 5min. Then 258.1g of chloromethane is slowly (30 min at a constant speed) introduced into the reaction kettle from the lower part of the liquid surface by a pressure reducing valve, the feeding speed is controlled to ensure that the pressure in the kettle is not higher than 0.2MPa, and the kettle is heated to 70 ℃ for reaction for 4h. Cooling the reaction solution to 35 ℃, and carrying out suction filtration; drying the filter cake for 180min at 100 ℃ under vacuum pressure of-0.08 MPa to prepare trimethyl ethyl ammonium chloride.
S2, electrolysis: the electrolysis equipment for electrolysis comprises an anode chamber 1, an absorption chamber 2, a raw material chamber 3 and a cathode chamber 4 which are sequentially adjacent; an anode plate 5 is arranged in the anode chamber 1, a cathode plate 6 is arranged in the cathode chamber 4, and the anode plate 5 is connected with the cathode plate 6 through a power supply; the anode chamber 1 is communicated with the absorption chamber 2 through a first cationic membrane 7, the absorption chamber 2 is communicated with the raw material chamber 3 through an anionic membrane 8, and the raw material chamber 3 is communicated with the cathode chamber 4 through a second cationic membrane 9. Firstly, preparing trimethyl ethyl ammonium chloride into an aqueous solution, adding the aqueous solution into a raw material chamber 3, and electrolyzing to make trimethyl ethyl ammonium cations enter a cathode chamber 4 through a second cationic membrane 9 to combine with hydroxide ions generated by a cathode to form trimethyl ethyl ammonium hydroxide, thereby preparing the quaternary ammonium alkali aqueous solution. In the electrolysis process, materials in the anode chamber 1, the absorption chamber 2, the raw material chamber 3 and the cathode chamber 4 are pumped and circulated by a circulating pump respectively. According to the concentration change condition of the trimethyl ethyl ammonium chloride in the raw material chamber 3, the trimethyl ethyl ammonium chloride aqueous solution is added into the raw material chamber 3 in the electrolysis process, so that the concentration of the trimethyl ethyl ammonium chloride in the raw material chamber 3 is kept at 10-18%. Electrolysis was carried out for 100 hours to obtain 14.5kg of an aqueous solution of trimethylethyl ammonium hydroxide having a mass concentration of 23.86%.
Example 2
Example 2 differs from example 1 in that example 2 step S1 uses a complex solvent of ethanol and acetonitrile, the weight ratio of ethanol to acetonitrile being 0.01:1, all other were identical to example 1.
Example 3
Example 3 differs from example 2 in that urea was added to the absorption chamber 2 at a mass concentration of 0.5% in step S2 of example 3, all other things being consistent with example 2.
Examples 4 to 7
Examples 4-7 differ from example 3 in that the proportions of the raw materials in examples 4-7 are different, and the other are the same as in example 3, and the proportions of the raw materials in examples 4-7 are shown in Table 1.
TABLE 1 proportions of the raw materials of examples 4 to 7
Comparative example
Comparative example 1
Comparative example 1 differs from example 1 in that step S2 of comparative example 1 was ion-exchanged with an ion-exchange resin (D201) without using an electrolytic method.
Comparative example 2
Comparative example 2 differs from example 1 in that methyl chloride was added first and trimethylamine was added later in step S1 of comparative example 2, and the other matters were the same as those of example 1.
Performance detection
1. The method for detecting the content of the quaternary ammonium hydroxide aqueous solution product comprises the following steps: 15g (accurate to 0.0002 g) of the sample solution was weighed and diluted to a 100mL volumetric flask, and shaken well to prepare a sample solution. 10mL of the sample solution was measured, poured into a 250mL triangular flask with a stopper, 10.00mL of a 100g/L barium chloride solution was added, 2-3 drops of a phenolphthalein indicator (0.1 g of a 10g/L phenolphthalein was dissolved in ethanol, and diluted to 100mL with ethanol) were added, and the mixture was stirred by a magnetic stirrer, and titrated with a standard titration solution of hydrochloric acid with a concentration of 0.1000mol/L until the red color was removed as an end point. The volume of standard titration solution consumed was noted as V1. The content (X1%) in mass percent is calculated as follows: x1% = v1c× 105.18; wherein: v1 is the volume of the hydrochloric acid standard solution consumed in measuring the sample solution, in mL; c is the molar concentration of the hydrochloric acid standard solution, and the unit mol/L; m is the mass of the sample, and is the unit g;105.18 is the molar mass of trimethyl ethyl ammonium hydroxide in g/mol.
2. And (3) measuring the content of chloride ions: and (3) taking a sample to be tested, cleaning an ion selection electrode by using ultrapure water, immersing the electrode into the sample to be tested, slowly stirring, and automatically displaying a Stable icon by the instrument after the measured value is Stable. And recording the measured value, and finishing the measurement. Calculation of
& -measured results of sample, ppm;
c-measured value on the sample meter, ppm;
m-mass of sample (unit g).
3. And (3) trimethylamine content measurement: using a chromatographic column DB-624, 30m x 0.53mm x 3 μm; sample inlet temperature: constant current mode at 200 ℃; detector temperature: FID,250 ℃. Column temperature: the temperature is kept at 60 ℃ for 6min, and the temperature is increased to 180 ℃ at 10 ℃ per minute, and the temperature is kept for 5min. Split ratio: 10: column flow rate: 10mL/min. Sample injection mode: headspace sample injection, sample injection amount: 1.00mL. The trimethylamine residual amount was detected by chromatography.
Table 2 comparative table of product quality index prepared in examples
| Experiment number | Product content (%) | Chloride ion content (ppm) | Trimethylamine content (ppm) |
| Example 1 | 23.86 | 29 | 34 |
| Example 2 | 23.91 | 18 | 11 |
| Example 3 | 25.73 | 21 | 12 |
| Example 4 | 25.54 | 15 | 8 |
| Example 5 | 25.87 | 19 | 3 |
| Example 6 | 25.65 | 17 | 2 |
| Example 7 | 25.78 | 20 | 10 |
| Comparative example 1 | 23.64 | 459 | 24 |
| Comparative example 2 | 23.78 | 37 | 93 |
Comparative example 1 an aqueous solution of trimethyl ethyl ammonium hydroxide was prepared by an ion exchange method, and the product had a low trimethylamine content but a high chloride ion content. Comparative example 2 an aqueous solution of trimethyl ethyl ammonium hydroxide was prepared by electrolysis with a low chloride ion content and a high trimethylamine content. Example 1 an aqueous solution of trimethyl ethyl ammonium hydroxide was prepared by electrolysis, and by appropriate addition sequence, the prepared product had lower chloride ion content and trimethylamine content, and the product had better quality.
The experimental results of example 1 and example 2 are compared, the compound solvent of ethanol and acetonitrile is used in example 2, and the trimethylamine content in the product is obviously reduced. The absorption chamber of the electrolysis apparatus of example 3 was charged with urea to increase the product content. Examples 4-7 used proper raw material proportion, the produced products have little impurity content and high product quality.
The embodiments of the present invention are all preferred embodiments of the present application, and are not intended to limit the scope of the present application in this way, therefore: all equivalent changes in structure, shape and principle of this application should be covered in the protection scope of this application.
Claims (9)
1. The preparation method of the trimethyl ethyl ammonium hydroxide is characterized by comprising the following steps of:
s1 quaternization: introducing trimethylamine into a reaction solvent, sealing, stirring, introducing chloroethane, heating to not lower than 60 ℃ for reaction for not less than 3 hours, and recovering a product to prepare trimethyl ethyl ammonium chloride;
s2, electrolysis: preparing aqueous solution by trimethyl ethyl ammonium chloride, adding the aqueous solution into an electrolysis device, and electrolyzing to obtain trimethyl ethyl ammonium cation, wherein the trimethyl ethyl ammonium cation enters a cathode chamber through a cation membrane and combines with hydroxide ions generated by a cathode to form trimethyl ethyl ammonium hydroxide, so as to prepare quaternary ammonium alkaline aqueous solution.
2. The method for preparing the trimethyl ethyl ammonium hydroxide according to claim 1, wherein the method comprises the following steps: the reaction solvent is a mixed solvent of acetonitrile and ethanol, and the weight ratio of the ethanol to the acetonitrile is (0.01-0.08): 1.
3. the method for preparing trimethyl ethyl ammonium hydroxide according to claim 1, wherein said step S1 recovering the product comprises the steps of: cooling the reaction solution to not higher than 35 ℃, carrying out suction filtration and vacuum drying to obtain trimethyl ethyl ammonium chloride; the vacuum drying pressure is less than or equal to-0.08 MPa, the drying temperature is 60-100 ℃, and the drying time is not less than 180min.
4. The method for preparing the trimethyl ethyl ammonium hydroxide according to claim 1, wherein the method comprises the following steps: the ratio of the amounts of the substances of trimethylamine and chloroethane is 1: (0.98-1).
5. The method for preparing the trimethyl ethyl ammonium hydroxide according to claim 2, wherein the method comprises the following steps: the ratio of the amount of the trimethylamine to the acetonitrile is 1: (4-10).
6. The method for preparing the trimethyl ethyl ammonium hydroxide according to claim 1, wherein the method comprises the following steps: the electrolysis equipment used in the step S2 comprises an anode chamber (1), an absorption chamber (2), a raw material chamber (3) and a cathode chamber (4) which are sequentially adjacent; an anode plate (5) is arranged in the anode chamber (1), a cathode plate (6) is arranged in the cathode chamber (4), and the anode plate (5) is connected with the cathode plate (6) through a power supply; the anode chamber (1) is communicated with the absorption chamber (2) through a first cationic membrane (7), the absorption chamber (2) is communicated with the raw material chamber (3) through an anionic membrane (8), and the raw material chamber (3) is communicated with the cathode chamber (4) through a second cationic membrane (9); step S2 is to prepare aqueous solution of trimethyl ethyl ammonium chloride, add the aqueous solution into a raw material chamber (3), electrolyze, make trimethyl ethyl ammonium cation enter a cathode chamber (4) through a second cation membrane (9), combine with hydroxide ion generated by a cathode, and form trimethyl ethyl ammonium hydroxide, thus preparing quaternary ammonium alkali aqueous solution.
7. The method for preparing the trimethyl ethyl ammonium hydroxide according to claim 6, wherein the method comprises the following steps: water is added to both the anode chamber (1) and the cathode chamber (4) of the step S2, and urea is added to the absorption chamber (2).
8. The method for preparing the trimethyl ethyl ammonium hydroxide according to claim 7, wherein the method comprises the following steps: the mass concentration of urea in the absorption chamber (2) of the step S2 is 0.5-2%.
9. An aqueous quaternary ammonium hydroxide solution, characterized in that: a process for preparing the trimethylammonium hydroxide according to any one of claims 1 to 8.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4776929A (en) * | 1986-11-25 | 1988-10-11 | Mitsubishi Gas Chemical Company, Inc. | Process for production of quaternary ammonium hydroxides |
| CN104974048A (en) * | 2014-04-11 | 2015-10-14 | 湖州欧美新材料有限公司 | High-purity tetraalkylammonium chloride water solution, preparation method and application thereof |
| CN114318376A (en) * | 2022-01-26 | 2022-04-12 | 肯特催化材料股份有限公司 | Preparation method of tetrapropylammonium hydroxide and quaternary ammonium alkaline water solution prepared by same |
-
2023
- 2023-02-13 CN CN202310110052.3A patent/CN116162943A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4776929A (en) * | 1986-11-25 | 1988-10-11 | Mitsubishi Gas Chemical Company, Inc. | Process for production of quaternary ammonium hydroxides |
| CN104974048A (en) * | 2014-04-11 | 2015-10-14 | 湖州欧美新材料有限公司 | High-purity tetraalkylammonium chloride water solution, preparation method and application thereof |
| CN114318376A (en) * | 2022-01-26 | 2022-04-12 | 肯特催化材料股份有限公司 | Preparation method of tetrapropylammonium hydroxide and quaternary ammonium alkaline water solution prepared by same |
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