CN101648927A - Synthesis method of epoxypropyltrimethylammonium chloride - Google Patents
Synthesis method of epoxypropyltrimethylammonium chloride Download PDFInfo
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- CN101648927A CN101648927A CN200910044265A CN200910044265A CN101648927A CN 101648927 A CN101648927 A CN 101648927A CN 200910044265 A CN200910044265 A CN 200910044265A CN 200910044265 A CN200910044265 A CN 200910044265A CN 101648927 A CN101648927 A CN 101648927A
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Abstract
The invention relates to a synthesis method of epoxypropyltrimethylammonium chloride. The method comprises the following steps: adding dichloroethane and epichlorohydrin in a reaction bottle in turn at 20-30 DEG C, injecting trimethylamine gas in the reaction bottle in a constant speed, reacting for 8-10h after injecting, reducing temperature to 5-15 DEG C while stopping stirring, filtrating to obtain white crystals; adding water to separate dichloroethane, heating with water bath to 60-70 DEG C, performing reduced pressure distillation, taking samples to test, stopping distillation when the concentration of epoxypropyltrimethylammonium chloride solution reaches 69%, and reducing temperature to obtain the desired product. The method overcomes the defect that the existing synthesized epoxypropyltrimethylammonium chloride contains impurities; intermediate 3-chloro-2-hydroxypropyltrimethyl ammonium chloride is not needed to prepare and the product is directly prepared so as to avoid the preparation of impurity 1,3-dichloro-2-propanol and bisquaternary ammonium salt, has high product quality and save the cost.
Description
Technical field
The present invention relates to a kind of synthetic method of epoxypropyl trimethylammonium chloride ammonium.
Background technology
At present, most of epoxypropyl trimethylammonium chloride ammonium (being commonly called as: cationic etherifying agent, english abbreviation GTA) all is to be transformed by 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride hydro-oxidation sodium to obtain on the market.
The synthetic method of 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride (english abbreviation CTA) is: earlier trimethylamine solution is added hydrochloric acid reaction and generate trimethylamine hydrochloride, and then add equimolar epichlorohydrin reaction.The advantage of this method is not high to personnel and equipment requirements, but product foreign matter content height, major impurity has epoxy chloropropane, 1,3-two chloro-2-propyl alcohol, bi-quaternary ammonium salt (changing the molten boiling point of product) etc., have a strong impact on the quality of 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride product, thereby also influenced the quality of epoxypropyl trimethylammonium chloride ammonium.
Summary of the invention
At above problem, the invention provides a kind of synthetic method of epoxypropyl trimethylammonium chloride ammonium, this method need not generate intermediate 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride, direct synthesizing epoxy oxypropyl trimethyl ammonium chloride, thereby avoided 1, the generation of 3-two chloro-2-propyl alcohol, these two kinds of impurity of bi-quaternary ammonium salt, the product quality height.
Synthetic method of the present invention is:
(1), adds ethylene dichloride earlier in the reaction flask the inside, add epoxy chloropropane again, temperature is controlled at 20-30 degree centigrade, at the uniform velocity feed Trimethylamine 99 gas in the reaction flask, the tail gas water absorbs, and the mol ratio of more than adding raw material is an ethylene dichloride: epoxy chloropropane: Trimethylamine 99=1.5～2: 1.0～1.5: 0.9～1;
(2), charge Trimethylamine 99 gas and reacted again later on 8～10 hours, reaction is cooled to 5～15 degrees centigrade after finishing, and stops in the temperature-fall period stirring, filter, white crystal;
(3), white crystal is put in the extraction flask, add certain water gaging, rock, left standstill five minutes, tell ethylene dichloride, heating in water bath again, bath temperature is 60-70 degree centigrade, underpressure distillation, sampling detects, and when the concentration of epoxypropyl trimethylammonium chloride ammonium solution reaches after 69%, stops distillation, cooling gets needed product.
Wherein the method for sampling detection may further comprise the steps:
(1), magnesium chloride saturated solution:
According to mol ratio magnesium oxide: water: hydrochloric acid=5.0～5.5: 8～8.5: 0.1～0.5, take by weighing magnesium chloride solids in beaker, be dissolved in water, placed 24 hours, saturated magnesium chloride solution is transferred in the brown reagent bottle, add hydrochloric acid again, after stirring, placed 12 hours, and filtered then, it is stand-by that filtrate is put into brown bottle;
(2), standard solution of sodium hydroxide is: 0.2-0.25mol/l;
(3), take by weighing about 0.6-1g epoxypropyl trimethylammonium chloride ammonium sample, be accurate to 0.001g, put into the 250ml iodine flask, add 25ml magnesium chloride saturated solution again, shake up the back water and seal, in the dark placed 30 minutes, add 2 methyl red indicators and 50ml deionized water, use the standard solution of sodium hydroxide titration to yellow then, do blank test simultaneously.
(4), calculate the concentration of epoxy oxypropyl trimethyl ammonium chloride solution:
The concentration of epoxypropyl trimethylammonium chloride ammonium solution (%)==[(V
0-V) C151.45]/10m
In the formula: V
0The volume (ml) of the standardized solution that----titration blank is consumed;
The volume (ml) of the standardized solution that V------titration sample is consumed;
The concentration of C------standard solution of sodium hydroxide (mol/l);
The weight of the alleged sample of m------(g).
Described reaction flask can be there-necked flask or four-hole boiling flask.
Described water can adopt distilled water or deionized water.
The present invention has following advantage: the synthetic method of epoxypropyl trimethylammonium chloride ammonium provided by the invention, this method need not generate intermediate 3-chloro-2-hydroxypropyl-trimethyl ammonium chloride, direct synthesizing epoxy oxypropyl trimethyl ammonium chloride, thereby avoided 1, the generation of 3-two chloro-2-propyl alcohol, these two kinds of impurity of bi-quaternary ammonium salt, the product quality height, and saved cost, bring very big economic benefit.
Embodiment
Embodiment 1:
(1), add the ethylene dichloride of 2mol earlier in four-hole boiling flask the inside, add the epoxy chloropropane of 1mol again, temperature is controlled at 20-25 degree centigrade, and 0.99mol Trimethylamine 99 gas is at the uniform velocity fed in the four-hole boiling flask, the tail gas water absorbs.
(2), charge Trimethylamine 99 gas and reacted again later on 8 hours, reaction is cooled to 5 degrees centigrade after finishing, and stops in the temperature-fall period stirring, filter, white crystal.
(3), white crystal is put in the extraction flask, add the distilled water of 1mol, rock, left standstill five minutes, tell ethylene dichloride.Heating in water bath again, bath temperature is 65 degrees centigrade, underpressure distillation, sampling detects, and wherein sampling detects and may further comprise the steps:
1. magnesium chloride saturated solution: take by weighing the 500g magnesium chloride solids in beaker, add the 150ml dissolved in purified water, placed 24 hours, saturated magnesium chloride solution is transferred in the brown reagent bottle, adds 11ml hydrochloric acid, after stirring, placed 12 hours, and filtered then, it is stand-by that filtrate is put into brown bottle;
2. sodium hydroxide mark solution is: 0.25mol/l;
3. take by weighing about 0.6 gram epoxypropyl trimethylammonium chloride ammonium sample, be accurate to 0.001g, put into the 250ml iodine flask, add 25ml magnesium chloride saturated solution again, shake up the back water and seal, in the dark placed 30 minutes, add 2 methyl red indicators and 50ml cationic water, use the standard solution of sodium hydroxide titration to yellow then, do blank test simultaneously;
4. calculate the concentration of epoxy oxypropyl trimethyl ammonium chloride solution:
The concentration of epoxypropyl trimethylammonium chloride ammonium solution (%)==[(V
0-V) C151.45]/10m
In the formula: V
0The volume (ml) of the standardized solution that----titration blank is consumed;
The volume (ml) of the standardized solution that V------titration sample is consumed;
The concentration of C------standard solution of sodium hydroxide (mol/l);
The weight of the alleged sample of m------(g).
When the concentration of epoxypropyl trimethylammonium chloride ammonium solution reaches after 69%, stop distillation, cooling, needed product.
Embodiment 2:
(1), add the ethylene dichloride of 2mol earlier in there-necked flask the inside, add the epoxy chloropropane of 1mol again, temperature is controlled at 20-25 degree centigrade, and 0.99mol Trimethylamine 99 gas is at the uniform velocity fed in the there-necked flask, the tail gas water absorbs.
(2), charge Trimethylamine 99 gas and reacted again later on 10 hours, reaction is cooled to 10 degrees centigrade after finishing, and stops in the temperature-fall period stirring, filter, white crystal.
(3), white crystal is put in the extraction flask, add the deionized water of 1mol, rock, left standstill five minutes, tell ethylene dichloride.Heating in water bath again, bath temperature is 68 degrees centigrade, underpressure distillation, sampling detects, and wherein detection method is identical with implementation column 1, when the concentration of epoxypropyl trimethylammonium chloride ammonium solution reaches after 69%, stops distillation, and cooling gets needed product.
Claims (4)
1, a kind of synthetic method of epoxypropyl trimethylammonium chloride ammonium is characterized in that by following steps synthetic:
(1), adds ethylene dichloride earlier in the reaction flask the inside, add epoxy chloropropane again, temperature is controlled at 20-30 degree centigrade, at the uniform velocity feed Trimethylamine 99 gas in the reaction flask, the tail gas water absorbs, and the mol ratio of more than adding raw material is an ethylene dichloride: epoxy chloropropane: Trimethylamine 99=1.5～2: 1.0～1.5: 0.9～1;
(2), charge Trimethylamine 99 gas and reacted again later on 8～10 hours, reaction is cooled to 5～15 degrees centigrade after finishing, and stops in the temperature-fall period stirring, filter, white crystal;
(3), white crystal is put in the extraction flask, add certain water gaging, rock, left standstill five minutes, tell ethylene dichloride, heating in water bath again, bath temperature is 60-70 degree centigrade, underpressure distillation, sampling detects, and when the concentration of epoxypropyl trimethylammonium chloride ammonium solution reaches after 69%, stops distillation, cooling gets needed product.
2, the synthetic method of a kind of epoxypropyl trimethylammonium chloride ammonium according to claim 1 is characterized in that: the method that described sampling detects may further comprise the steps:
(1), magnesium chloride saturated solution:
According to mol ratio magnesium oxide: water: hydrochloric acid=5.0～5.5: 8～8.5: 0.1～0.5, take by weighing magnesium chloride solids in beaker, be dissolved in water, placed 24 hours, saturated magnesium chloride solution is transferred in the brown reagent bottle, add hydrochloric acid again, after stirring, placed 12 hours, and filtered then, it is stand-by that filtrate is put into brown bottle;
(2), standard solution of sodium hydroxide is: 0.2-0.25mol/l;
(3), take by weighing about 0.6-1g epoxypropyl trimethylammonium chloride ammonium sample, be accurate to 0.001g, put into the 250ml iodine flask, add 25ml magnesium chloride saturated solution again, shake up the back water and seal, in the dark placed 30 minutes, add 2 methyl red indicators and 50ml deionized water, use the standard solution of sodium hydroxide titration to yellow then, do blank test simultaneously;
(4), calculate the concentration of epoxy oxypropyl trimethyl ammonium chloride solution:
The concentration of epoxypropyl trimethylammonium chloride ammonium solution (%)==[(V
0-V) C151.45]/10m
In the formula: V
0The volume (ml) of the standardized solution that----titration blank is consumed;
The volume (ml) of the standardized solution that V------titration sample is consumed;
The concentration of C------standard solution of sodium hydroxide (mol/l);
The weight of the alleged sample of m-----(g).
3, the synthetic method of a kind of epoxypropyl trimethylammonium chloride ammonium according to claim 1 is characterized in that: described reaction flask can be there-necked flask or four-hole boiling flask.
4, the synthetic method of a kind of epoxypropyl trimethylammonium chloride ammonium according to claim 1 and 2 is characterized in that: described water can adopt distilled water or deionized water.
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| CN2009100442650A CN101648927B (en) | 2009-09-01 | 2009-09-01 | Synthesis method of epoxypropyltrimethylammonium chloride |
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| CN2009100442650A CN101648927B (en) | 2009-09-01 | 2009-09-01 | Synthesis method of epoxypropyltrimethylammonium chloride |
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| CN101648927A true CN101648927A (en) | 2010-02-17 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103936600A (en) * | 2014-04-16 | 2014-07-23 | 天津大学 | Method for purifying cationic etherifying agent via phosphate ester extraction agent |
| CN107721862A (en) * | 2017-10-17 | 2018-02-23 | 浙江工业大学 | The synthetic method of the adamantyl ammonium halide of N, N, N trimethyl 1 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104371687A (en) * | 2014-12-05 | 2015-02-25 | 陕西延长石油油田化学科技有限责任公司 | Clay stabilizer for oil fields |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1139635C (en) * | 2000-12-22 | 2004-02-25 | 石油大学(北京) | Process for synthesizing cationic additive for electrode of polymer electrolyte and its application |
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2009
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103936600A (en) * | 2014-04-16 | 2014-07-23 | 天津大学 | Method for purifying cationic etherifying agent via phosphate ester extraction agent |
| CN103936600B (en) * | 2014-04-16 | 2016-08-24 | 天津大学 | Phosphoric acid ester extractant purifies the method for cationic etherifying agent |
| CN107721862A (en) * | 2017-10-17 | 2018-02-23 | 浙江工业大学 | The synthetic method of the adamantyl ammonium halide of N, N, N trimethyl 1 |
| CN107721862B (en) * | 2017-10-17 | 2020-04-07 | 浙江工业大学 | Synthesis method of N, N, N-trimethyl-1-adamantyl ammonium halide |
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| CN101648927B (en) | 2012-05-02 |
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