CN1053057A - Synthesis of choline chloride by self-catalyzed reaction - Google Patents
Synthesis of choline chloride by self-catalyzed reaction Download PDFInfo
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- CN1053057A CN1053057A CN 91100043 CN91100043A CN1053057A CN 1053057 A CN1053057 A CN 1053057A CN 91100043 CN91100043 CN 91100043 CN 91100043 A CN91100043 A CN 91100043A CN 1053057 A CN1053057 A CN 1053057A
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- choline
- reaction
- choline chloride
- chloroethanol
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Abstract
A kind of method of synthesis of choline chloride by self-catalyzed reaction.With Trimethylamine 99 and chloroethanol is raw material, add choline chloride 60 or other choline salt as the autocatalysis agent, Trimethylamine 99 and chloroethanol mol ratio are 1.0: 0.9～1.1, the catalyzer addition is the 0.1-10% of reaction raw materials amount, temperature of reaction 20-150 ℃, reaction pressure normal pressure or low pressure, stirring reaction 2-5 hour total conversion rate and yield can reach more than 99% and 97% respectively.This synthetic method safety, no explosion hazard, speed of response is fast, the product purity height.
Description
The present invention relates to a kind of production technology for choline chloride, particularly a kind of autocatalytic method is produced choline chloride 60 technology.
Choline chloride 60 is a kind of important fodder additives, and pharmaceuticals and organic synthesis reagent have been widely used.The method of in the past producing choline chloride 60 mainly is divided into epoxyethane method and chloroethanol method, and the epoxyethane method cost of material is higher, and explosion hazard is arranged in the production; Chloroethanol method technology is simple, is catalyzer but need add all kinds of alkali, and the inorganics in the catalyzer remains in the product, influences the quality of product.
The objective of the invention is to overcome the deficiency of in the past producing the choline chloride 60 method, a kind of safety is provided, do not add the technology of the synthesizing chlorinated choline of assorted alkaline catalysts, good product quality.
The technical measures that realize the object of the invention are to be raw material with Trimethylamine 99 and chloroethanol, with choline chloride 60 or other choline salt is the autocatalysis agent, synthesizing chlorinated choline under normal temperature and pressure or low pressure, and choline chloride 60 or choline salt are accelerated building-up reactions, improve productive rate, improve quality product.
As the choline chloride 60 that the autocatalysis agent is used, can be the product of industrial goods, chemical reagent or this building-up reactions self, its physico-chemical property is:
Face shaping: colorless solid
Molecular weight: 139.63
Rank: industrial goods or reagent
Proportion: 1.42
Mp:＞240 ℃ of decomposition
n
D: the 1.4080(50% aqueous solution)
Reaction raw materials Trimethylamine 99 and chloroethanol mol ratio are 1.0: 0.9-1.1, be preferably 1.0: 0.97-1.03, catalyzer choline chloride 60 or other choline salt, or the addition that choline adds equimolar amount is the 0.1-10.0% of building-up reactions total stuff amount, is preferably 2-4%, at 1-5atm, 20-150 ℃, reaction is 2-8 hour under constantly stirring in reactor, and transformation efficiency is more than 99%, and yield is 98%.
Compare with method of the present invention, identical in other condition, add other 2 kinds of catalyzer, the transformation efficiency of sodium hydroxide and Tetramethylammonium hydroxide is respectively 94% and 92%.Quality product is not as good as autocatalysis synthesis method products obtained therefrom quality.The results are shown in Table 1.
Embodiment 1
33% industrial goods trimethylamine solution 70ml, 32% industrial goods chloroethanol 50ml, the solid choline chloride 0.4g of content＞95%, add in the 250ml there-necked flask, be heated to 50 ℃, stir 500 rev/mins, reacted 3 hours, sampling analysis is after reaction finishes, added activated carbon decolorizing 20 minutes, the amounts of activated carbon thing is material quantity 1% weight, the elimination gac, obtain containing 31% choline chloride 60 120ml, transformation efficiency 99%, yield is 100%, product purity sees Table 1.
Embodiment 2
This example is a comparative example, 33% industrial goods Trimethylamine 99 70ml, 32% industrial goods chloroethanol 50ml, 50 ℃ of following stirring reactions are after 3 hours, and the activated carbon decolorizing of adding raw material total amount 1% 20 minutes gets 28% choline chloride 60 120ml behind the elimination gac, transformation efficiency 88%, yield is 90%, quality product sees Table 1.
Embodiment 3
This example is a comparative example, 33% industrial goods Trimethylamine 99 70ml, 32% industrial goods chloroethanol 50ml, solid sodium hydroxide 0.4g, under 50 ℃ of normal pressures in the 250ml there-necked flask stirring reaction 3 hours, add up the activated carbon decolorizing 20 minutes of material quantity 1%, filter to such an extent that contain 29% choline chloride 60 120ml, transformation efficiency 94.2%, yield is 94%, quality product sees Table 1.
Embodiment 4
This example also is a comparative example, 33% industrial Trimethylamine 99 70ml, and 32% industrial chloroethanol 50ml adds catalyzer tetramethyl-hydrogen
Ammonium oxide 0.4g, 50 ℃ of following stirring reactions are 3 hours in the 250ml there-necked flask, add the activated carbon decolorizing 20 minutes of raw material total amount 1%, 29% choline chloride solution 120ml, transformation efficiency 91.9%, yield is 92%, the results are shown in Table 1.
Embodiment 5
33% industrial Trimethylamine 99 45kg, volume is 71l, 32% industrial chloroethanol 62.5kg, volume is 52l, drops in the 200l reactor, be 61% in reactor internal volume occupation rate.Add choline chloride 60 0.37kg,, check that reaction is complete substantially in 50 ℃ of following stirring reactions 5 hours.Add the 1.1kg activated carbon decolorizing, getting product after the filtration is 31% choline chloride 60 107kg, and volume is 120l, transformation efficiency 99%, and yield 98%, quality product sees Table 1.
Embodiment 6
Trimethylamine 99 20.8kg, chloroethanol 28.9kg drops into reactor, adds embodiment 5 products therefrom 0.5kg, begin in the time of 20 ℃ to stir, the reaction beginning, pressure is 1.1kg/cm
2, get product mixed solution 49.7kg after 2 hours, wherein choline chloride 60 content is 31.0%, yield is 98.5%.
Embodiment 7
Industry Trimethylamine 99 23.0kg, chloroethanol 31.5kg adds embodiment 6 products therefrom 0.5kg, begins stirring reaction under 80 ℃, and top temperature reaches 150 ℃, and pressure is 4kg/cm
2, after 1.5 hours, obtaining product weight 54.6kg, choline chloride 60 content is 30.0%, yield is 99%.
Embodiment 8
Trimethylamine 99 19.6kg, chloroethanol 30.9kg adds phosphorylcholine 0.5kg, and 50 ℃ of following stirring reactions obtain product 50kg after 3 hours.Choline chloride 60 content 31% in the product, yield are 98%.
Embodiment 9
Trimethylamine 99 19.6kg, chloroethanol 30.9kg adds equimolar choline and hydrochloric acid reaction product 0.5kg, and 50 ℃ of following stirring reactions get product 50kg, choline chloride 60 content 31% in the product after 2.5 hours.Yield is 98%.
Table 1
| Embodiment number | Catalyzer | Temperature of reaction ℃ | Raw material ratio a | Transformation efficiency % | Yield % | Product purity b | ||
| Ammonium salt | Ethylene glycol | Ignition residue | ||||||
| 1 | Choline chloride 60 | 50 | 1.03∶1∶0.03 | 100 | 99 | 0.20 | 0.07 | 0.01 |
| 2 | Do not have | 50 | 1.03∶1∶0 | 90.8 | 88 | 0.40 | 0.08 | 0.02 |
| 3 | NaOH | 50 | 1.03∶1∶0.03 | 94.2 | 95 | 0.29 | 0.10 | 0.06 |
| 4 | （CH)NOH | 50 | 1.03∶1∶0.03 | 91.9 | 92 | 0.30 | 0.16 | 0.02 |
| 5 | Choline chloride 60 | 50 | 1.03∶1∶0.03 | 99 | 98 | 0.20 | 0.11 | 0.01 |
A: Trimethylamine 99: chloroethanol: catalyst molar ratio
B: by the standard analysis of China national veterinary drug
Claims (5)
1, a kind of synthetic method of choline chloride 60, with Trimethylamine 99 and chloroethanol is raw material, with alkali is catalyzer, synthetic under normal temperature and pressure or low pressure, the mol ratio that it is characterized in that Trimethylamine 99 and chloroethanol is 1.0: 0.9～1.1, and catalyzer is a choline salt, the catalyzer addition is the 0.1-10% of reaction material amount, temperature of reaction is 20-150 ℃, and reaction is 2-5 hour in stirred reactor, transformation efficiency＞99%.
2,, it is characterized in that Trimethylamine 99 and chloroethanol optimum mole ratio are 1.0: 0.97～1.03 as the method for the synthesizing chlorinated choline of claim 1.
3,, it is characterized in that catalyzer is choline chloride 60 or other choline salt, or choline adds equimolar amount hydrochloric acid as the method for the synthesizing chlorinated choline of claim 1.
4,, it is characterized in that the more firmly add-on of catalyzer choline chloride 60 or choline salt is the 2-4% of reaction material amount as the method for the synthesizing chlorinated choline of claim 1.
5, as the method for the synthesizing chlorinated choline of claim 1, it is characterized in that catalyzer choline chloride 60 or choline salt, can outer add mode add reaction system, also can the residual mode of product stay in the reaction system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 91100043 CN1053057A (en) | 1991-01-02 | 1991-01-02 | Synthesis of choline chloride by self-catalyzed reaction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 91100043 CN1053057A (en) | 1991-01-02 | 1991-01-02 | Synthesis of choline chloride by self-catalyzed reaction |
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| Publication Number | Publication Date |
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| CN1053057A true CN1053057A (en) | 1991-07-17 |
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| CN 91100043 Pending CN1053057A (en) | 1991-01-02 | 1991-01-02 | Synthesis of choline chloride by self-catalyzed reaction |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633622B (en) * | 2009-07-24 | 2013-03-13 | 杭州海尔希畜牧科技有限公司 | Method for preparing choline chloride |
| CN109180502A (en) * | 2018-08-09 | 2019-01-11 | 绍兴东湖高科股份有限公司 | Utilize the tubular reactor and method of cycocel production End gas production choline chloride |
| CN110172757A (en) * | 2019-06-25 | 2019-08-27 | 中原工学院 | A kind of device and method improving combing sliver quality |
| WO2023017323A1 (en) * | 2021-08-12 | 2023-02-16 | Hafez Varesh | Method of the effective synthesis of active choline chloride ingredient using heterogeneous nanocatalysts based on copper and molybdenum |
-
1991
- 1991-01-02 CN CN 91100043 patent/CN1053057A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633622B (en) * | 2009-07-24 | 2013-03-13 | 杭州海尔希畜牧科技有限公司 | Method for preparing choline chloride |
| CN109180502A (en) * | 2018-08-09 | 2019-01-11 | 绍兴东湖高科股份有限公司 | Utilize the tubular reactor and method of cycocel production End gas production choline chloride |
| CN109180502B (en) * | 2018-08-09 | 2021-04-30 | 绍兴东湖高科股份有限公司 | Tubular reactor and method for producing choline chloride by using chlormequat chloride production tail gas |
| CN110172757A (en) * | 2019-06-25 | 2019-08-27 | 中原工学院 | A kind of device and method improving combing sliver quality |
| CN110172757B (en) * | 2019-06-25 | 2020-07-03 | 中原工学院 | Device and method for improving quality of combed cotton sliver |
| WO2023017323A1 (en) * | 2021-08-12 | 2023-02-16 | Hafez Varesh | Method of the effective synthesis of active choline chloride ingredient using heterogeneous nanocatalysts based on copper and molybdenum |
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