CN116589362A - Technological method for preparing tetradecyl trimethyl ammonium bisulfate - Google Patents
Technological method for preparing tetradecyl trimethyl ammonium bisulfate Download PDFInfo
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- CN116589362A CN116589362A CN202211614473.1A CN202211614473A CN116589362A CN 116589362 A CN116589362 A CN 116589362A CN 202211614473 A CN202211614473 A CN 202211614473A CN 116589362 A CN116589362 A CN 116589362A
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- trimethyl ammonium
- tetradecyl trimethyl
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- methanol
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- LRWSTBIEJXJNJY-UHFFFAOYSA-M hydron;trimethyl(tetradecyl)azanium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCCCCCCC[N+](C)(C)C LRWSTBIEJXJNJY-UHFFFAOYSA-M 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000003756 stirring Methods 0.000 claims abstract description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 24
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000012043 crude product Substances 0.000 claims abstract description 18
- 239000000706 filtrate Substances 0.000 claims abstract description 18
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 claims abstract description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims abstract description 12
- 238000000967 suction filtration Methods 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 9
- 239000007787 solid Substances 0.000 claims abstract description 9
- 238000004448 titration Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- 230000001376 precipitating effect Effects 0.000 claims abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 239000012065 filter cake Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000007864 suspending Methods 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 238000004537 pulping Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000007731 hot pressing Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- -1 quaternary ammonium salt compound Chemical class 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a process method for preparing tetradecyl trimethyl ammonium bisulfate. The method of the invention comprises the following steps: adding tetradecyl trimethyl ammonium bromide into methanol, stirring and dissolving, controlling the temperature to be within 30 ℃, dropwise adding a methanol solution of potassium hydroxide, and stirring at room temperature overnight after the dropwise adding is finished; filtering after the reaction is finished, cooling the obtained filtrate to 0-10 ℃, dropwise adding concentrated sulfuric acid for reaction, and stirring at room temperature overnight after the completion of the dropwise adding; concentrating the reaction solution to dryness, adding acetone, heating for dissolution, performing hot press filtration, cooling the obtained filtrate to 0-10 ℃, adding ethyl acetate, precipitating a large amount of white solid, performing suction filtration, and performing suspension washing, suction filtration and drying on the obtained solid by using ethyl acetate to obtain a crude product; and recrystallizing the crude product by butanone to obtain white powder solid, and checking to obtain the target product, namely the tetradecyl trimethyl ammonium bisulfate. The neutralization titration purity of the tetradecyl trimethyl ammonium bisulfate prepared by the invention reaches more than 99%, and the total yield is more than 95%.
Description
Technical Field
The invention relates to a process method for preparing tetradecyl trimethyl ammonium bisulfate, belonging to the technical field of chemical synthesis.
Background
The unique molecular structure of the quaternary ammonium salt compound endows the quaternary ammonium salt compound with a series of physical and chemical effects, such as emulsification, dispersion, solubilization, washing, wetting, foaming, sterilization, coagulation, leveling, corrosion resistance, antistatic and the like, and corresponding practical application, and the unique properties enable the quaternary ammonium salt compound to have very good application prospects in the fields of textiles, dyes, pesticides, medicines, foods, washing and personal care products, high and new technologies and the like.
The tetradecyl trimethyl ammonium bisulfate also belongs to an important organic chemical raw material quaternary ammonium salt, is commonly used in the aspects of some surfactants, ion chromatographic pairs, medicines, pesticides and the like, also belongs to an important phase transfer catalyst in organic medicine synthesis, and has very wide application. Therefore, the synthesis of the novel quaternary ammonium salt compound tetradecyl trimethyl ammonium bisulfate has great research value.
Disclosure of Invention
The purpose of the invention is that: aiming at the prior art, no related report on the preparation of novel quaternary ammonium salt compound tetradecyl trimethyl ammonium bisulfate is provided, and the required process raw materials are easy to obtain, low in cost, high in product conversion rate, simple to operate, free of severe reaction requirements, easy to industrialize, and economical and applicable.
In order to achieve the above object, the present invention provides a process for preparing tetradecyl trimethyl ammonium bisulfate, comprising the steps of:
step 1): methanol is taken as a solvent, tetradecyl trimethyl ammonium bromide is added at the temperature of 20-25 ℃, raw material reaction liquid is obtained after stirring and dissolving, a methanol solution of potassium hydroxide is dripped into the raw material reaction liquid, the temperature of the reaction liquid is controlled to be 30 ℃, and after dripping is finished, stirring and reacting are carried out at room temperature;
step 2): cooling the reaction liquid obtained in the step 1) to 0-10 ℃, preserving heat for 1 hour, starting suction filtration, washing the obtained filter cake with methanol, merging filtrate, then dropwise adding concentrated sulfuric acid into the filtrate, and stirring at room temperature for reaction after the dropwise addition is completed;
step 3): concentrating the reaction solution obtained in the step 2) under reduced pressure until the reaction solution is dried to obtain a concentrated dried substance, adding acetone, heating, stirring and dissolving, hot-pressing and filtering while the solution is hot, cooling the filtrate to below 10 ℃, adding ethyl acetate, precipitating white solid, performing suction filtration, pulping and suspending the obtained filter cake with ethyl acetate, and performing vacuum drying to obtain a crude product;
step 4): and 3) recrystallizing and purifying the crude product obtained in the step 3) through butanone to obtain a pure product of the tetradecyl trimethyl ammonium bisulfate.
Preferably, the weight ratio of the volume of methanol in the reaction raw material liquid in the step 1) to the tetradecyl trimethyl ammonium bromide is 3-5L/kg, the weight ratio of the volume of methanol in the methanol solution of potassium hydroxide to the weight ratio of potassium hydroxide is 2-4L/kg, and the mole ratio of the potassium hydroxide to the tetradecyl trimethyl ammonium bromide is 1-1.5: 1.
preferably, in the step 2), the internal temperature of the reaction is controlled to be within 10 ℃, and concentrated sulfuric acid is added dropwise, wherein the molar ratio of the concentrated sulfuric acid to the tetradecyl trimethyl ammonium bromide is 1-1.2: 1.
preferably, the weight ratio of the volume of the acetone added in the step 3) to the concentrated dry matter is 3-5L/kg, and the volume ratio of the ethyl acetate to the acetone is 2-4: 1.
preferably, the weight ratio of butanone volume to crude product required by Ding Tongchun crystallization in the step 4) is 5-8L/kg; the neutralization titration purity of the pure product is more than 99 percent.
The invention adopts the industrial cheap and easily available tetradecyl trimethyl ammonium bromide, potassium hydroxide and sulfuric acid as main raw materials, and common auxiliary materials such as methanol, ethyl acetate, acetone, butanone and the like, and the target product crude product is obtained through 2 steps of synthesis, and the high-purity product tetradecyl trimethyl ammonium bisulfate is obtained after recrystallization and purification, wherein the neutralization titration purity is more than 99%, and the total yield is more than 95%. The invention has the advantages of low cost of synthetic raw materials, simple process, good reaction controllability, high reaction conversion rate and the like, and is suitable for industrial production.
Compared with the prior art, the invention has the beneficial effects that:
1. the raw materials required by the process method of the invention, namely tetradecyl trimethyl ammonium bromide, potassium hydroxide, sulfuric acid, methanol, ethyl acetate, acetone, butanone and the like, are cheap and easily available industrial products, and have mild reaction conditions and convenient operation; the reaction is easy to control, the side reaction is less, and the reaction conversion rate is high; the purification of the target product is simple, and the whole process is suitable for industrial production;
2. the invention synthesizes tetradecyl trimethyl ammonium bisulfate by adopting a 2-step method; wherein, the tetradecyl trimethyl ammonium bromide reacts with potassium hydroxide to prepare an intermediate, the occurrence of side reaction is reduced and the conversion rate is improved by controlling the temperature of the reaction and the dosage ratio of materials, then the intermediate reacts with concentrated sulfuric acid solution to perform ion exchange, and the obtained crude product is recrystallized and purified by butanone to obtain the high-purity product tetradecyl trimethyl ammonium bisulfate, wherein the neutralization purity is more than 99%, and the total yield is more than 95%.
Detailed Description
In order to make the present invention more comprehensible, preferred embodiments accompanied with the present invention are described in detail below.
Examples 1 and 2 provide a process for preparing tetradecyl trimethyl ammonium bisulfate, wherein the chemical equation of the synthesis process is as follows:
a process method for preparing tetradecyl trimethyl ammonium bisulfate comprises the following steps:
(1) Preparing a 10L glass reaction kettle, filling argon, adding 4.5L of methanol at 20-25 ℃, stirring, adding tetradecyl trimethyl ammonium bromide (1.5 kg,4.46 mol), stirring and dissolving after the addition, slowly dropwise adding a methanol (750 ml) solution of KOH (250 g,4.46 mol), controlling the temperature of a reaction solution to be 30 ℃, dropwise adding, and stirring at room temperature for reaction overnight after the dropwise addition;
(2) Cooling the reaction liquid to 0-10 ℃ by using an ice water bath, preserving heat for 1h, starting suction filtration, suspending and washing a filter cake by using methanol (1L multiplied by 1), merging filtrate, cooling the filtrate to 0-10 ℃ by using the ice water bath, starting dropwise adding concentrated sulfuric acid (437 g,4.46 mol) into the filtrate, controlling the temperature in the reaction kettle to be within 10 ℃, and stirring at room temperature for reaction overnight after the dropwise adding;
(3) Concentrating the reaction solution under reduced pressure at 40 ℃ until the reaction solution is dried to obtain 3kg, adding 9L of acetone, heating to 40 ℃ for stirring and dissolving, hot press filtering, cooling the obtained filtrate to below 10 ℃, adding 27L of ethyl acetate while stirring, precipitating a large amount of white solid, suction filtering, pulping and suspending the filter cake with ethyl acetate (1L multiplied by 1), and drying the crude product at 40 ℃ for 24 hours under vacuum to obtain 1.62kg of dry crude product;
(4) Preparing a 10L glass reaction bottle, adding 8.1L butanone and 1.62kg crude product respectively, stirring, heating and refluxing until the crude product is dissolved, then performing hot filtration, standing and refrigerating filtrate at 0-10 ℃, preserving heat for 3-5 hours, performing suction filtration to obtain a large amount of white solid, and performing vacuum drying at 40 ℃ to obtain 1.52kg compound.
Nuclear magnetic resonance treatment data and neutralization titration of the prepared compound are detected as follows:
1 H-NMR(CDCl 3 ，400MHz，δppm)：δ＝6.54～6.89(1H，br)，3.36(2H，m)，3.26(9H，s)，1.29～1.31(2H，m)，1.24～1.27(22H，m)，0.87(3H，t)ppm
neutralization titration: 99.5%;
the total yield of tetradecyl trimethyl ammonium bisulfate prepared in this example was 96%.
Example 2
A process method for preparing tetradecyl trimethyl ammonium bisulfate comprises the following steps:
(1) Preparing a 10L glass reaction kettle, filling argon, adding 6.0L of methanol at 20-25 ℃, stirring, adding tetradecyl trimethyl ammonium bromide (1.2 kg,3.57 mol), stirring and dissolving after the addition, slowly dropwise adding a methanol (900 ml) solution of KOH (300 g,5.35 mol), controlling the temperature of the reaction solution to be 30 ℃, dropwise adding, and stirring at room temperature for reaction overnight after the dropwise addition;
(2) Cooling the reaction liquid to 0-10 ℃ by using an ice water bath, preserving heat for 1h, starting suction filtration, suspending and washing a filter cake by using methanol (1L multiplied by 1), merging filtrate, cooling the filtrate to 0-10 ℃ by using the ice water bath, starting dropwise adding concentrated sulfuric acid (420 g,4.28 mol) into the filtrate, controlling the temperature in the reaction kettle to be within 10 ℃, and stirring at room temperature for reaction overnight after the dropwise adding;
(3) Concentrating the reaction solution under reduced pressure at 40 ℃ until the reaction solution is dried to obtain 2.7kg, adding 13.5L of acetone, heating to 40 ℃ for stirring and dissolving, hot press filtering, cooling the obtained filtrate to below 10 ℃, adding 40.5L of ethyl acetate while stirring, precipitating a large amount of white solid, carrying out suction filtration, pulping and suspending the filter cake with ethyl acetate (1L multiplied by 1), and carrying out vacuum drying on the crude product at 40 ℃ for 24h to obtain 1.3kg of dry crude product;
(4) Preparing a 20L glass reaction bottle, adding 10.4L butanone and 1.3kg crude product respectively, stirring, heating and refluxing until the crude product is dissolved, then performing hot filtration, standing and refrigerating filtrate at 0-10 ℃, preserving heat for 3-5 hours, performing suction filtration to obtain a large amount of white solid, and performing vacuum drying at 40 ℃ to obtain 1.2kg compound.
Nuclear magnetic resonance treatment data and neutralization titration of the prepared compound are detected as follows:
1 H-NMR(CDCl 3 ，400MHz，δppm)：δ＝6.58～6.84(1H，br)，3.38(2H，m)，3.25(9H，s)，1.28～1.31(2H，m)，1.23～1.28(22H，m)，0.85(3H，t)ppm
neutralization titration: 99.6%;
the total yield of tetradecyltrimethylammonium bisulfate prepared in this example was 95%.
Claims (5)
1. A process method for preparing tetradecyl trimethyl ammonium bisulfate is characterized by comprising the following steps:
step 1): methanol is taken as a solvent, tetradecyl trimethyl ammonium bromide is added at the temperature of 20-25 ℃, raw material reaction liquid is obtained after stirring and dissolving, a methanol solution of potassium hydroxide is dripped into the raw material reaction liquid, the temperature of the reaction liquid is controlled to be 30 ℃, and after dripping is finished, stirring and reacting are carried out at room temperature;
step 2): cooling the reaction liquid obtained in the step 1) to 0-10 ℃, preserving heat for 1 hour, starting suction filtration, washing the obtained filter cake with methanol, merging filtrate, then dropwise adding concentrated sulfuric acid into the filtrate, and stirring at room temperature for reaction after the dropwise addition is completed;
step 3): concentrating the reaction solution obtained in the step 2) under reduced pressure until the reaction solution is dried to obtain a concentrated dried substance, adding acetone, heating, stirring and dissolving, hot-pressing and filtering while the solution is hot, cooling the filtrate to below 10 ℃, adding ethyl acetate, precipitating white solid, performing suction filtration, pulping and suspending the obtained filter cake with ethyl acetate, and performing vacuum drying to obtain a crude product;
step 4): and 3) recrystallizing and purifying the crude product obtained in the step 3) through butanone to obtain a pure product of the tetradecyl trimethyl ammonium bisulfate.
2. The process for preparing tetradecyltrimethylammonium bisulfate according to claim 1, wherein the weight ratio of the volume of methanol to the tetradecyltrimethylammonium bromide in the reaction raw material liquid of the step 1) is 3 to 5L/kg, the weight ratio of the volume of methanol to the weight ratio of potassium hydroxide in the methanol solution of potassium hydroxide is 2 to 4L/kg, and the molar ratio of potassium hydroxide to tetradecyltrimethylammonium bromide is 1 to 1.5:1.
3. the process for preparing tetradecyl trimethyl ammonium bisulfate according to claim 1, wherein in the step 2), concentrated sulfuric acid is dropwise added at a reaction internal temperature of 10 ℃ or less, and a molar ratio of the concentrated sulfuric acid to the tetradecyl trimethyl ammonium bromide is 1-1.2: 1.
4. the process for preparing tetradecyl trimethyl ammonium bisulfate according to claim 1, wherein the weight ratio of the added acetone to the concentrated dried material in the step 3) is 3-5L/kg, and the volume ratio of the ethyl acetate to the acetone is 2-4: 1.
5. the process for preparing tetradecyl trimethyl ammonium bisulfate according to claim 1, wherein the ratio by weight of butanone volume required for crystallization to crude product in the step 4) is 5 to 8L/kg by adopting Ding Tongchun; the neutralization titration purity of the pure product is more than 99 percent.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211614473.1A CN116589362A (en) | 2022-12-15 | 2022-12-15 | Technological method for preparing tetradecyl trimethyl ammonium bisulfate |
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| CN202211614473.1A CN116589362A (en) | 2022-12-15 | 2022-12-15 | Technological method for preparing tetradecyl trimethyl ammonium bisulfate |
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