CN101168511A - Method for preparing hydroxypropyl diquaternary ammonium salt - Google Patents
Method for preparing hydroxypropyl diquaternary ammonium salt Download PDFInfo
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Abstract
The invention discloses a preparation method of hydroxy propyl bisquaternary ammonium salt, and the preparation method has the advantages that the process is simple, and the process is green and environment-protective. The invention comprises the following steps: under the required air atmosphere, the HX water solution in the formula (1) is poured into a reaction vessel, the control temperature is 15 DEG C to 60 DEG C, chloroepoxy propane is dropped into the reaction vessel, after the reaction, the substance in the formula (2) is added at one time or in several times, or dropped continuously, the temperature rises to 40 DEG C to 120 DEG C, after the sufficient reaction, the target product of hydroxy propyl bisquaternary ammonium salt can be obtained, and the structure of the target product is expressed with the formula (3). The product can be extensively applied in the preparation of sterilization and algae extermination, metal anticorrosion, fabric dyeing and finishing, asphalt emulsification, waste paper deinking, fiber dispersion and electropositive ion monomer containing repellency water base.
Description
Technical field
The present invention relates to a kind of tensio-active agent---the preparation method of hydroxypropyl diquaternary ammonium salt.
Background technology
The excellent properties of current bi-quaternary ammonium salt tensio-active agent is just progressively approved and is had to popularize the trend of using, but its study on the synthesis work far lags behind applied research.This may technical scaleization be not relevant as yet with this series products, and the preparation of a small amount of trial target substantially all rests on the experimental phase, considers not enough to cost and operation.Present more use be two step method, promptly make halo hydroxypropyl mono-quaternaries earlier and purify, quaternized with another tertiary amine again, complex operation, production cost height have also proposed stability requirement to the alkyl on the nitrogen in addition like this, and many kinds can't be produced.
Summary of the invention
Technical problem to be solved by this invention is: will provide that a kind of technology is simple, the preparation method of the hydroxypropyl diquaternary ammonium salt of technological process environmental protection.
For solving the problems of the technologies described above, the technical solution used in the present invention is: the preparation method of described hydroxypropyl diquaternary ammonium salt, comprise the steps: under required atmosphere, the HX aqueous solution of formula (1) is dropped into reactor, controlled temperature is 15 ℃～60 ℃, in reactor, drip epoxy chloropropane, the time that drips can be controlled at more than one hour, reaction Bi Yici adding or gradation add or drip continuously the material of formula (2), be warming up to 40 ℃～120 ℃, fully promptly obtain the target product hydroxypropyl diquaternary ammonium salt after the reaction, the reaction times can be controlled at more than six hours, and the structure of target product is represented with formula (3); Can also remove or not remove moisture content and relevant solvent orange 2 A in the product at last as required.
Wherein R1, R2, R3, R4 are selected from the saturated or unsaturated alkyl that contains a carbon atom at least independently of one another, special preferable methyl, ethyl, allyl group.R5, R6 are selected from the straight chain of methyl, ethyl, allyl group, ethyl propenoate base, Jia Jibingxisuanyizhi base, methacryloyl amido propyl group and 4 carbon to 22 carbon independently of one another or contain the saturated or unsaturated alkyl of side chain; X represents a kind of halogen atom that combines with positively charged ion.
In actual fabrication process, identical with (2) formula as (1) formula, then the two can add when feeding intake simultaneously.
Above-mentioned required gas is the miscellany of nitrogen, argon gas, carbonic acid gas, oxygen, air or above-mentioned any several gases.
Mol ratio between above-mentioned formula (1) and the epoxy chloropropane is 2: 1 to 1: 2; Mol ratio between formula (2) and the epoxy chloropropane is 2: 1 to 1: 2.
The HX aqueous solution of above-mentioned formula (1) is made by following method: under the described atmosphere of claim 1, formula (1) is dropped into reactor, add entry, solvent orange 2 A, heating up to stir makes it dissolving, and controlled temperature is 10 ℃-80 ℃ and splashes into the HX aqueous solution; Wherein solvent orange 2 A is selected from the mixture of methyl alcohol, ethanol, Virahol, the trimethyl carbinol, acetone, dimethyl formamide or above-mentioned any several materials; X represents halogen, refers to chlorine, bromine, iodine especially.And the mol ratio between formula (1) and the HX is 2: 1 to 1: 2.
Among the present invention, the target product of gained can also be obtained crystal more than 90% by crystallization process again, concrete steps are: add solvent B in products obtained therefrom, stirring, filtration, washing, dry cake promptly get required crystal.Described solvent B is selected from the mixture of Virahol, the trimethyl carbinol, acetone, dimethyl formamide, ether or above-mentioned any several materials.
The invention has the beneficial effects as follows: described method is succinct, easy handling, and facility investment is few, and the three wastes are few, energy consumption is low, and resulting liquid intermediates just can directly apply to the downstream and produce, and can realize that covering device fecund product are shared.Of many uses, the excellent performance of described series product, in many industries are upgradings of currently available products, and, make the various application advantages of bi-quaternary ammonium salt be able to play a role in each field for the industrialization of each kind hydroxypropyl diquaternary ammonium salt provides an easy access.
Embodiment
Below in conjunction with specific embodiment the present invention is done to describe further, but the present invention should not only limit to these embodiment.
Embodiment 1
In the 500ml reactor, add 203g dodecyl dimethyl tertiary amine, 80g ethanol, start and stir and backflow, with nitrogen replacement three times, splash into 20% hydrochloric acid 84.4g, the control dropping temperature is not more than 60 ℃, be warming up to 50 ℃ after dripping off, begin to drip the 46.26g epoxy chloropropane, with the water-bath cooling, control material temperature is not more than 60 ℃, drips off the back 50-85 ℃ of insulation 1 hour, slowly be warming up to backflow (80-90 ℃), constant temperature 8 hours is cooled to and mends 30g ethanol below 60 ℃, is cooled to 40 ℃ with the bottom discharge analysis.Obtain the 433.7g light yellow transparent liquid, survey quaternized thing active matter content 59.5%, unhindered amina 0.7% calculates yield 98.5%.
Get above-mentioned weak yellow liquid 500g, add 150g acetone while stirring, remove by filter solvent, dry and obtain the 262g white crystal.
Embodiment 2
In the 500ml reactor, add 101.5g dodecyl dimethyl tertiary amine, 80g ethanol, start and stir and backflow, with nitrogen replacement three times, splash into 20% hydrochloric acid 84.4g, the control dropping temperature is not more than 60 ℃, be warming up to 50 ℃ after dripping off, begin to drip the 46.26g epoxy chloropropane, with the water-bath cooling, control material temperature is not more than 60 ℃, drip off the back 50-85 ℃ of insulation 1 hour, once add second batch of 101.5g dodecyl dimethyl tertiary amine then, slowly be warming up to backflow (80-90 ℃), constant temperature 8 hours, be cooled to and mend 30g ethanol below 60 ℃, be cooled to 40 ℃ with the bottom discharge analysis.Obtain the 455.0g light yellow transparent liquid, survey quaternized thing active matter content 56.02%, unhindered amina 0.83% calculates yield 98.1%.
Embodiment 3
In the 500ml reactor, add 229.39g tetradecyl dimethyl tertiary amine, 80g Virahol, start and stir and backflow, with nitrogen replacement three times, splash into 20% hydrochloric acid 88g, the control dropping temperature is not more than 60 ℃, be warming up to 50 ℃ after dripping off, begin to drip the 46.26g epoxy chloropropane, with the water-bath cooling, control material temperature is not more than 60 ℃, drips off the back 50-85 ℃ of insulation 1 hour, slowly be warming up to backflow (80-90 ℃), constant temperature 12 hours is cooled to and mends 20g ethanol below 60 ℃, is cooled to 40 ℃ with the bottom discharge analysis.Obtain light yellow transparent liquid, survey quaternized thing active matter content 56.7%, unhindered amina 0.88% calculates yield 96.9%.
Embodiment 4
In the 1000ml reactor, add 439.2gC16-18 alkyl dimethyl tertiary amide (70%C18 alkyl dimethyl tertiary amide, the 30%C16 alkyl dimethyl tertiary amide), 326.8g ethanol, start and stir and backflow, with nitrogen replacement three times, splash into 20% hydrochloric acid 147.06g, 45-60 ℃ of control dropping temperature, be warming up to 55 ℃ after dripping off, begin to drip the 75.4g epoxy chloropropane, cool off with water-bath, control material temperature is not more than 65 ℃, drip off the back 65-70 ℃ of insulation 1 hour, slowly be warming up to backflow (85-90 ℃), constant temperature 16 hours, be cooled to and mend 20g ethanol below 60 ℃, be cooled to 40 ℃ with the bottom discharge analysis.Obtain white lotion, survey quaternized thing active matter content 51.15%, unhindered amina 0.67% calculates yield 98.39%.
Embodiment 5
In the 500ml reactor, add 101.5g dodecyl dimethyl tertiary amine, 80g ethanol, start and stir and backflow, with nitrogen replacement three times, splash into 20% hydrochloric acid 84.4g, the control dropping temperature is not more than 60 ℃, be warming up to 50 ℃ after dripping off, begin to drip the 46.26g epoxy chloropropane, with the water-bath cooling, control material temperature is not more than 60 ℃, drip off the back 50-85 ℃ of insulation 1 hour, once add 114.69g tetradecyl dimethyl tertiary amine then, slowly be warming up to backflow (80-90 ℃), constant temperature 12 hours, be cooled to and mend 30g ethanol below 60 ℃, be cooled to 40 ℃ with the bottom discharge analysis.Obtain the 431.5g yellow transparent liquid, loss 25.35g solvent is surveyed quaternized thing active matter content 53.2%, and unhindered amina 0.79% calculates yield 97.1%.
Embodiment 6
In the 500ml reactor, add 46.32g trimethylamine hydrochloride, 75g deionized water, start and stir and backflow, use nitrogen replacement three times, be warming up to 50 ℃, begin to drip the 46.26g epoxy chloropropane, with the water-bath cooling, control material temperature is not more than 60 ℃, drip off the back 50-85 ℃ of insulation 1 hour, once add 101.5g dodecyl dimethyl tertiary amine then, slowly be warming up to backflow (80-90 ℃), constant temperature 6.5 hours, be cooled to and mend 20g ethanol below 60 ℃, be cooled to 40 ℃ with the bottom discharge analysis.Obtain the 285.1g light yellow transparent liquid, survey quaternized thing active matter content 67.6%, unhindered amina 0.32% calculates yield 99.5%.
Embodiment 7
In the 500ml reactor, add 101.5g dodecyl dimethyl tertiary amine, the 100g deionized water, start and stir and backflow, with nitrogen replacement three times, splash into 20% hydrochloric acid 84.4g, the control dropping temperature is not more than 60 ℃, be warming up to 50 ℃ after dripping off, begin to drip the 46.26g epoxy chloropropane, cool off with water-bath, control material temperature is not more than 60 ℃, drip off the back 65 ℃ of insulations 1 hour, once add 82.51g dimethylaminopropyl methacrylamide (DMAPMA) then, switching nitrogen is the slow bubbling of air, slowly be warming up to 65-70 ℃, constant temperature 16 hours is cooled to and adds 20g MEHQ (MEHQ) below 40 ℃, stops bubbling, discharging is analyzed.Obtain light yellow transparent liquid, survey quaternized thing active matter content 57.45%, unhindered amina 0.66%.
Claims (10)
1. the preparation method of hydroxypropyl diquaternary ammonium salt, it is characterized in that: under required atmosphere, the HX aqueous solution of formula (1) is dropped into reactor, controlled temperature is 15 ℃～60 ℃, drip epoxy chloropropane in reactor, reaction Bi Yici adding or gradation add or drip continuously the material of formula (2), are warming up to 40 ℃～120 ℃, fully promptly obtain the target product hydroxypropyl diquaternary ammonium salt after the reaction, its structure is represented with formula (3).
Wherein R1, R2, R3, R4 are selected from the saturated or unsaturated alkyl that contains a carbon atom at least independently of one another; R5, R6 are selected from the straight chain of methyl, ethyl, allyl group, ethyl propenoate base, Jia Jibingxisuanyizhi base, methacryloyl amido propyl group, 4 carbon to 22 carbon independently of one another or contain the saturated or unsaturated alkyl of side chain; X represents a kind of halogen atom that combines with positively charged ion.
2. preparation method as claimed in claim 1 is characterized in that: R1, R2, R3, R4 are selected from methyl, ethyl, allyl group independently of one another.
3. preparation method as claimed in claim 1 or 2 is characterized in that: identical with (2) formula as (1) formula, then the two can add when feeding intake simultaneously.
4. preparation method as claimed in claim 1 or 2 is characterized in that: required gas is the miscellany of nitrogen, argon gas, carbonic acid gas, oxygen, air or above-mentioned any several gases.
5. preparation method as claimed in claim 1 or 2 is characterized in that: the mol ratio between formula (1) and the epoxy chloropropane is 2: 1 to 1: 2; Mol ratio between formula (2) and the epoxy chloropropane is 2: 1 to 1: 2.
6. preparation method as claimed in claim 1, it is characterized in that: the HX aqueous solution of formula (1) is made by following method: under the described atmosphere of claim 1, formula (1) is dropped into reactor, add entry, solvent orange 2 A, heating up to stir makes it dissolving, and controlled temperature is 10 ℃-80 ℃ and splashes into the HX aqueous solution; Wherein solvent orange 2 A is selected from the mixture of methyl alcohol, ethanol, Virahol, the trimethyl carbinol, acetone, dimethyl formamide or above-mentioned any several materials; X represents halogen.
7. as claim 1 or 6 described preparation methods, it is characterized in that: X represents chlorine, bromine, iodine.
8. as claim 6 or 7 described preparation methods, it is characterized in that: the mol ratio between formula (1) and the HX is 2: 1 to 1: 2.
9. preparation method as claimed in claim 1, it is characterized in that: the target product of gained is obtained crystal more than 90% by crystallization process again, concrete steps are: add solvent B in products obtained therefrom, stirring, filtration, washing, dry cake promptly get required crystal.
10. preparation method as claimed in claim 9 is characterized in that: described solvent B is selected from the mixture of Virahol, the trimethyl carbinol, acetone, dimethyl formamide, ether or above-mentioned any several materials.
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Cited By (18)
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| CN101637155A (en) * | 2009-08-26 | 2010-02-03 | 北京拓凯化工技术有限公司 | Bactericidal and algaecidal composition for intermediate water system, preparation method and application thereof |
| CN102511479A (en) * | 2011-12-06 | 2012-06-27 | 孙安顺 | Dual-cation bactericide, preparation method and application thereof |
| CN102516095A (en) * | 2011-11-18 | 2012-06-27 | 江苏博特新材料有限公司 | Compound containing multielement alkamines, and preparation method and application thereof |
| CN102531928A (en) * | 2011-12-15 | 2012-07-04 | 成都齐达水处理工程股份有限公司 | Asymmetric bis-quaternary ammonium salt as well as preparation method and application thereof |
| CN101711527B (en) * | 2009-12-31 | 2013-02-20 | 蚌埠丰原医药科技发展有限公司 | Bactericidal composition and preparation method thereof |
| CN103406063A (en) * | 2013-08-08 | 2013-11-27 | 上海发凯化工有限公司 | Cationic gemini surfactant preparation method |
| CN103980132A (en) * | 2013-02-08 | 2014-08-13 | 上海龙孚材料技术有限公司 | Hydroxypropyl diquaternary ammonium salt, emulsified bitumen and preparation methods and application thereof |
| CN104128120A (en) * | 2014-07-22 | 2014-11-05 | 武汉工程大学 | Preparation method of cationic gemini surfactant with connection chain containing hydroxy group |
| CN104592045A (en) * | 2014-12-04 | 2015-05-06 | 常州大学 | One-step synthetic method of didodecyl gamma-diquaternium salt |
| CN104604934A (en) * | 2015-01-21 | 2015-05-13 | 成都科宏达科技有限公司 | Novel composite iodine disinfectant as well as preparation method and application thereof |
| CN106221514A (en) * | 2016-08-27 | 2016-12-14 | 安徽省金盾涂料有限责任公司 | A kind of high-hardness, wearable coating |
| CN106279680A (en) * | 2016-08-12 | 2017-01-04 | 贯硕磉 | Quaternary cationics and preparation method thereof |
| CN106268495A (en) * | 2016-08-04 | 2017-01-04 | 中国日用化学工业研究院 | A kind of N, N, N cocoyl hydroxyethyl methyl N ', N ', N ' the double ammonium chloride surfactant of dihydroxy ethyl methyl trimethylene and preparation method |
| CN107619076A (en) * | 2017-11-08 | 2018-01-23 | 山东利水环保科技有限公司 | The formula of the special water purification agent of aquaculture class |
| CN108840803A (en) * | 2018-07-11 | 2018-11-20 | 山东泰和水处理科技股份有限公司 | A kind of synthetic method of asymmetry biquaternary ammonium salts bactericides |
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| CN113666835A (en) * | 2021-10-22 | 2021-11-19 | 北京诺苇生物技术有限公司 | Dodecyl dimethyl hydroxypropyl trimethyl diammonium chloride and synthetic method and application thereof |
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2007
- 2007-11-22 CN CNA2007101904075A patent/CN101168511A/en active Pending
Cited By (23)
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| CN101637155A (en) * | 2009-08-26 | 2010-02-03 | 北京拓凯化工技术有限公司 | Bactericidal and algaecidal composition for intermediate water system, preparation method and application thereof |
| CN101711527B (en) * | 2009-12-31 | 2013-02-20 | 蚌埠丰原医药科技发展有限公司 | Bactericidal composition and preparation method thereof |
| CN102516095A (en) * | 2011-11-18 | 2012-06-27 | 江苏博特新材料有限公司 | Compound containing multielement alkamines, and preparation method and application thereof |
| CN102516095B (en) * | 2011-11-18 | 2014-04-16 | 江苏博特新材料有限公司 | Compound containing multielement alkamines, and preparation method and application thereof |
| CN102511479A (en) * | 2011-12-06 | 2012-06-27 | 孙安顺 | Dual-cation bactericide, preparation method and application thereof |
| CN102531928A (en) * | 2011-12-15 | 2012-07-04 | 成都齐达水处理工程股份有限公司 | Asymmetric bis-quaternary ammonium salt as well as preparation method and application thereof |
| CN102531928B (en) * | 2011-12-15 | 2013-11-06 | 成都齐达水处理工程股份有限公司 | Asymmetric bis-quaternary ammonium salt as well as preparation method and application thereof |
| CN103980132A (en) * | 2013-02-08 | 2014-08-13 | 上海龙孚材料技术有限公司 | Hydroxypropyl diquaternary ammonium salt, emulsified bitumen and preparation methods and application thereof |
| CN103406063A (en) * | 2013-08-08 | 2013-11-27 | 上海发凯化工有限公司 | Cationic gemini surfactant preparation method |
| CN104128120A (en) * | 2014-07-22 | 2014-11-05 | 武汉工程大学 | Preparation method of cationic gemini surfactant with connection chain containing hydroxy group |
| CN104592045A (en) * | 2014-12-04 | 2015-05-06 | 常州大学 | One-step synthetic method of didodecyl gamma-diquaternium salt |
| CN104604934A (en) * | 2015-01-21 | 2015-05-13 | 成都科宏达科技有限公司 | Novel composite iodine disinfectant as well as preparation method and application thereof |
| CN104604934B (en) * | 2015-01-21 | 2017-11-03 | 成都科宏达科技有限公司 | A kind of compound iodine disinfectant and its preparation method and application |
| CN106268495A (en) * | 2016-08-04 | 2017-01-04 | 中国日用化学工业研究院 | A kind of N, N, N cocoyl hydroxyethyl methyl N ', N ', N ' the double ammonium chloride surfactant of dihydroxy ethyl methyl trimethylene and preparation method |
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| CN107619076B (en) * | 2017-11-08 | 2020-08-14 | 山东利水环保科技有限公司 | Formula of special water purifying agent for aquaculture |
| CN108840803A (en) * | 2018-07-11 | 2018-11-20 | 山东泰和水处理科技股份有限公司 | A kind of synthetic method of asymmetry biquaternary ammonium salts bactericides |
| CN108840803B (en) * | 2018-07-11 | 2021-03-12 | 山东泰和水处理科技股份有限公司 | Method for synthesizing asymmetric biquaternary ammonium salt bactericide |
| CN109896974A (en) * | 2019-03-07 | 2019-06-18 | 西南石油大学 | A kind of bielectron type polymerisable surfactant monomer, preparation method and application |
| CN110973142A (en) * | 2019-12-24 | 2020-04-10 | 甘肃泰升化工科技有限公司 | Power plant sterilization algicide and preparation method thereof |
| CN113666835A (en) * | 2021-10-22 | 2021-11-19 | 北京诺苇生物技术有限公司 | Dodecyl dimethyl hydroxypropyl trimethyl diammonium chloride and synthetic method and application thereof |
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