CN112457202A - Synthesis process of dialkyl dimethyl ammonium chloride - Google Patents
Synthesis process of dialkyl dimethyl ammonium chloride Download PDFInfo
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- CN112457202A CN112457202A CN202011433676.1A CN202011433676A CN112457202A CN 112457202 A CN112457202 A CN 112457202A CN 202011433676 A CN202011433676 A CN 202011433676A CN 112457202 A CN112457202 A CN 112457202A
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- dimethyl ammonium
- dialkyl dimethyl
- halide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
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Abstract
The invention discloses a synthesis process of dialkyl dimethyl ammonium halide, which is to synthesize primary alkyl halide R1X and long-chain alkyldimethylamine R2（CH3）2Mixing N, heating to 130-150 ℃ in a closed container, carrying out heat preservation reaction for 4-6h, cooling, and diluting with an ethanol water solution to obtain dialkyl dimethyl ammonium halide; reaction temperature from R1And R2The number of carbon atoms of (C) is determined by the formula 130 ℃ +2.5 (C)R1+CR2-16) deg.C. In the invention, the primary alkyl halide and the long-chain alkyl dimethylamine directly react to generate the dialkyl dimethyl ammonium halide, thereby avoiding the use of flammable and explosive gaseous raw materials and increasing the production safety; the production process flow and equipment are simple, the production cost is low, the industrial popularization is facilitated, the by-products of acid and salt are not generated, the product purity is high, three wastes are not generated, and the environment is protected.
Description
Technical Field
The invention belongs to the technical field of fine chemical synthesis, and particularly relates to a synthesis process of dialkyl dimethyl ammonium halide.
Background
The quaternary ammonium salt is also called quaternary ammonium salt, and the properties of the inorganic salt are similar, so that the quaternary ammonium salt is easily dissolved in water, and the water solution can conduct electricity. Mainly by reaction of ammonia or amines with primary alkyl halides. It has wide application, and can be used as bactericidal algicide, softening antistatic agent, flocculant, demulsifier, drilling fluid, VES fracturing fluid, drag reducer, thickener, anion synergist, etc.
In recent years, the research on quaternary ammonium salt has the traditional advantages of environmental protection, easy biodegradation and small toxic and side effects, and a series of products are developed. From the simplest alkyldimethylbenzylammonium chlorides to dialkyldimethylammonium halides, from mono-quaternary ammonium salts to bis-quaternary ammonium salts to polyquaternary ammonium salts. The application focus of the above-mentioned kind of products also varies. The quaternary ammonium salt has good bactericidal performance, the quaternary ammonium salt connecting two long carbon chains has good expressive activity, the phase transfer agent has the effect, the bactericidal and decontamination capability of the detergent can be improved by adding a small amount of the quaternary ammonium salt, and the quaternary ammonium salt is widely used in the daily chemical washing industry.
At present, the synthesis of dialkyl dimethyl ammonium halide is mainly carried out in two ways, namely, primary alkyl halide and dimethylamine are reacted in a strong alkali environment to prepare the dialkyl dimethyl ammonium bromide series products by taking alkyl bromide and dimethylamine as raw materials, such as carbofuran and the like. Secondly, tertiary amine is produced by primary alcohol and monomethylamine, and then the tertiary amine reacts with methyl halide to generate dialkyl dimethyl ammonium halide. For example, the sub-peak of the Cao is reacted by n-decanol and monomethylamine under hydrogen environment to generate didecyl methyl tertiary amine, and then the didecyl methyl tertiary amine is reacted with methyl chloride to generate didecyl dimethyl ammonium chloride.
The monomethylamine and dimethylamine used in the two methods are both gases at normal temperature, have low boiling points and low flash points, are flammable and explosive, and are not beneficial to safe production. And when dimethylamine is used, halogenated acid is generated, a large amount of alkali is wasted during neutralization, a large amount of heat is discharged, resources are wasted, the production risk is increased, and when monomethylamine is used, the monomethylamine is mixed with hydrogen for use, and the high-temperature reaction increases the potential safety risk of production. And is not suitable for large-scale production in practical application.
In conclusion, the research and development of the synthesis process of the dialkyl dimethyl ammonium halide, which has the advantages of simple production method, safety, high efficiency and cost saving, has important significance.
Disclosure of Invention
Aiming at the problems of complex process, low safety and high cost of synthesizing the dialkyl dimethyl ammonium halide in the prior art, the invention provides the synthesis process of the dialkyl dimethyl ammonium halide, which avoids the use of gas raw materials, is safe and efficient, and is suitable for industrial production.
The invention is realized by the following technical scheme:
a synthetic process of dialkyl dimethyl ammonium halideTo convert a primary alkyl halide R1X and long-chain alkyldimethylamine R2（CH3）2Mixing N, heating to 130-150 ℃ in a closed container, carrying out heat preservation reaction for 4-6h, cooling, and diluting with an ethanol water solution to obtain dialkyl dimethyl ammonium halide;
wherein X represents a halogen ion.
Further, said primary alkyl halide R1The molar ratio of X to long-chain alkyldimethylamine is 1: 1.
Further, the primary alkyl halide is primary chloroalkane.
Further, said R1The number of carbon atoms in (b) is 8, 10 or 12, and R is2The number of carbon atoms in (b) is 8, 10 or 12.
Further, the reaction temperature is represented by R1And R2The number of carbon atoms of (C) is determined by the formula 130 ℃ +2.5 (C)R1+CR2-16)℃；
Wherein C isR1And CR2Represents R1And R2The number of carbon atoms.
Further, the volume ratio of water to ethanol in the ethanol water solution is 3-5: 1.
Furthermore, the closed container is a high-pressure reaction kettle.
Advantageous effects
(1) In the invention, the primary alkyl halide and the long-chain alkyl dimethylamine directly react to generate the dialkyl dimethyl ammonium halide, thereby avoiding the use of flammable and explosive gaseous raw materials and increasing the production safety;
(2) the invention has simple production process flow and equipment, low production cost, no by-product of acid and salt, high product purity, no three wastes and environmental protection, and is beneficial to industrial popularization.
Detailed Description
The present invention is described in detail below by way of examples, which are intended to be illustrative only and not to be construed as limiting the scope of the invention, and one skilled in the art will be able to make variations within the scope of the invention based on the disclosure herein, in reagents, catalysts and reaction process conditions. All equivalent changes or modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Part of the raw materials and equipment specifications used in the examples:
the purity of tertiary amine is 99%; the chloroalkanes were 98% pure and were all purchased commercially.
Example 1
Adding 157g of octyl dimethyl tertiary amine and 148g of 1-chlorooctane into a high-pressure reaction kettle, sealing, putting into an oven lifted to 130 ℃ in advance, reacting for 4 hours at constant temperature, cooling, and adding 300g of water and ethanol mixed solution with the volume ratio of 5:1 for dilution to obtain 605g of dioctyl dimethyl ammonium chloride aqueous solution with the activity content of 49.64%. The conversion rate of the reaction material (calculated by tertiary amine) is 98.46 percent and the chloride ion content is 5.79 percent by converting the activity of the product (detected by a tetraphenyl borax titration color development method).
Example 2
Adding 213g of dodecyl dimethyl tertiary amine and 204g of 1-chlorododecane into a high-pressure reaction kettle, sealing, putting into an oven lifted to 150 ℃ in advance, reacting for 4 hours at a constant temperature, cooling, and adding 400g of mixed solution of water and ethanol with the volume ratio of 3:1 for dilution to obtain 817g of dioctyl dimethyl ammonium chloride aqueous solution with the activity content of 50.49%. The conversion rate of the reaction materials (calculated by tertiary amine) is 98.92 percent and the chloride ion content is 4.30 percent by converting the activity of the product (detected by a tetraphenyl borax titration color development method).
Comparative example 1
157g of octyl dimethyl tertiary amine and 148g of 1-chlorooctane are added into a high-pressure reaction kettle, the mixture is sealed and then put into an oven lifted to 100 ℃ in advance, after the constant-temperature reaction for 6 hours, the mixture is cooled and then added with 300g of mixed solution of water and ethanol with the volume ratio of 5:1 for dilution, and 605g of dioctyl dimethyl ammonium chloride aqueous solution with the activity content of 27.59% is obtained. The conversion rate of the reaction material (calculated by tertiary amine) is 54.73 percent and the content of chloride ions is 3.21 percent by converting the activity of the product (detected by a tetraphenyl borax titration color development method).
Comparative example 2
157g of octyl dimethyl tertiary amine and 148g of 1-chlorooctane are added into a high-pressure reaction kettle, the mixture is sealed and then put into an oven lifted to 170 ℃ in advance, after the constant-temperature reaction for 4 hours, the mixture is cooled and then added with 300g of mixed solution of water and ethanol with the volume ratio of 5:1 for dilution, and 605g of dioctyl dimethyl ammonium chloride aqueous solution with the activity content of 39.55 percent is obtained. The conversion rate of the reaction material (calculated by tertiary amine) is 78.46% by converting the activity of the product (detected by tetraphenyl borax titration color development method), and the content of chloride ions is 5.85%.
Comparative example 3
The method comprises the following steps: adding 308g of n-decanol and a catalyst into a 1L reaction kettle, heating to 100 ℃, introducing hydrogen, activating the catalyst at 180 ℃, heating to 200 ℃, introducing a mixed gas of hydrogen and monomethylamine according to a molar ratio of 4:1, carrying out amination reaction, collecting water from the outside of a water separator, absorbing excessive monomethylamine with water, cooling and filtering after reacting for 4 hours, and distilling the filtrate under reduced pressure to obtain 297g of colorless and transparent didecyl methyl tertiary amine;
step two: adding 297g of didecyl methyl tertiary amine, 10g of sodium carbonate and 50g of isopropanol into a high-pressure reaction kettle, replacing air with nitrogen, heating to 80-90 ℃, introducing methane chloride, reacting for 4 hours under the pressure of 0.3-0.5 MPa in the kettle to obtain 340g of didecyl dimethyl ammonium chloride. The product is detected, the conversion rate of the intermediate tertiary amine (calculated by alcohol) is 95.6 percent, and the conversion rate of the didecyl dimethyl ammonium chloride (calculated by tertiary amine) is 98.25 percent.
Claims (7)
1. A process for synthesizing dialkyl dimethyl ammonium halide is characterized by that the primary alkyl halide R1X and long-chain alkyldimethylamine R2（CH3）2Mixing N, heating to 130-150 ℃ in a closed container, carrying out heat preservation reaction for 4-6h, cooling, and diluting with an ethanol water solution to obtain dialkyl dimethyl ammonium halide;
wherein X represents a halogen ion.
2. The process of claim 1 wherein said primary alkyl halide R1The molar ratio of X to long-chain alkyldimethylamine is 1: 1.
3. The process of claim 1 wherein the primary alkyl halide is a primary alkyl chloride.
4. The synthetic process of claim 1 wherein R is1The number of carbon atoms in (b) is 8, 10 or 12, and R is2The number of carbon atoms in (b) is 8, 10 or 12.
5. The process of claim 1, wherein the reaction temperature is defined by R1And R2The number of carbon atoms of (C) is determined by the formula 130 ℃ +2.5 (C)R1+CR2-16)℃；
Wherein C isR1And CR2Represents R1And R2The number of carbon atoms.
6. The synthesis process according to claim 1, wherein the volume ratio of water to ethanol in the ethanol aqueous solution is 3-5: 1.
7. The process of claim 1, wherein the closed vessel is an autoclave.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117263807A (en) * | 2023-11-23 | 2023-12-22 | 成都科宏达化学有限责任公司 | High-purity dialkyl dimethyl ammonium chloride and preparation method thereof |
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| JP2005161720A (en) * | 2003-12-03 | 2005-06-23 | Canon Inc | Sizing agent and recording paper using the same |
| CN101428206A (en) * | 2007-08-13 | 2009-05-13 | 中国科学院成都有机化学有限公司 | Double-tail quaternary ammonium salt cation surface active agent and preparation method thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005161720A (en) * | 2003-12-03 | 2005-06-23 | Canon Inc | Sizing agent and recording paper using the same |
| CN101428206A (en) * | 2007-08-13 | 2009-05-13 | 中国科学院成都有机化学有限公司 | Double-tail quaternary ammonium salt cation surface active agent and preparation method thereof |
Non-Patent Citations (2)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117263807A (en) * | 2023-11-23 | 2023-12-22 | 成都科宏达化学有限责任公司 | High-purity dialkyl dimethyl ammonium chloride and preparation method thereof |
| CN117263807B (en) * | 2023-11-23 | 2024-02-06 | 成都科宏达化学有限责任公司 | Dialkyl dimethyl ammonium chloride and preparation method thereof |
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