CN101898971A - Method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave - Google Patents
Method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave Download PDFInfo
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Abstract
The invention belongs to a method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave. N-methyldiethanolamine and octadecyl bromide are used as raw materials, and n-hexanol or n-pentanol is used as a solvent. The method comprises the following steps of: performing microwave reflux under the power of 400 to 600W, and reacting the raw materials for 15 to 25 minutes to obtain octadecyl methyl dihydroxyethyl ammonium bromide, wherein the obtained the octadecyl methyl dihydroxyethyl ammonium bromide is a crude product; and re-crystallizing the crude product for several times by using acetone, filtering the solution to obtain bright white crystal, and drying the crystal to obtain the high-purity octadecyl methyl dihydroxyethyl ammonium bromide, wherein the purity reaches over 99 percent. The synthesizing method has short reaction time and lower energy consumption; compared with a traditional heating method, the reaction rate is improved by nearly 23 times; and the method has high conversion rate which can reach over 95 percent, has high utilization rate of raw materials, and further saves the cost.
Description
Technical field
The invention belongs to chemical field, relate to a kind of method of synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave.
Background technology
Along with the develop rapidly of science and technology, continuing to bring out of novel process, novel material and new technology, the application of tensio-active agent that is referred to as " industrial monosodium glutamate " is also extensive day by day.Wherein cats product is owing to its special structure presents particular performances such as static resistance, bactericidal properties, flexibility etc., and these properties are that the tensio-active agent of other type is irreplaceable.Studies show that, show better surfactivity during the composite use of yin, yang ionic surface active agent.But in most cases, the yin, yang ionic surface active agent is met and get along well the generation precipitation mutually and is lost surfactivity.The Application Areas of cats product is constantly widened in recent years, has obtained to use widely in new and high technology.There is data to show that in recent years, the rate of growth of cats product was more faster than negatively charged ion, nonionic.About the synthetic method and the performance study of quaternary ammonium cation tensio-active agent, more report is arranged also both at home and abroad.Prior synthesizing method mainly is to make by long carbochain fat tertiary amine and alkylating reagent (methyl chloride, Benzyl Chloride, methyl-sulfate etc.) reaction.This series products has the applicating history of decades, is badly in need of developing new product variety to satisfy the growth requirement of relevant industries.
Octadecyl methyl diethyl brometo de amonio is compared with common quaternary ammonium salt, not only contain N+ in its molecular structure, and two hydroxyethyls of connection on the N atom, improved wetting ability greatly, make it and anion surfactant is composite can not produce precipitation, surfactivity improves greatly, is a kind of new and effective cats product.Because it has stronger adsorptive power to the material that has negative charge, can be used as the sterilant and the fabric softener of various bacteria, improved antibiotic, the softness and the whiteness of fabric preferably.It has good static resistance in addition, can be used as plastic anti-static agent and textile auxiliary agent.Therefore, octadecyl methyl diethyl brometo de amonio more and more is subject to people's attention as the application of aspects such as tensio-active agent, yarn fabric auxiliary agent.But at present, the synthetic method of octadecyl methyl diethyl brometo de amonio is still comparatively traditional, fails to satisfy the demand of present stage for octadecyl methyl diethyl brometo de amonio.
Microwave chemical is to grow up on the characteristic of material in to microwave field and the interactional further investigation basis thereof, mainly is heat effect and the non-thermal effect that utilizes microwave.Interaction---the microwave chemical of research microwave and chemical reaction system, development in recent years is very fast, and obtains more and more many concerns, can reduce energy consumption, reduce and pollute, improve product property, therefore be described as " Green Chemistry ", great application prospect is arranged.Though microwave synthesis method has been applied to the synthetic of multiple compound, has reached preferable effect.But, aspect synthetic octadecyl methyl diethyl brometo de amonio, do not see any report yet.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of simple possible is provided, the method for the synthetic octadecyl methyl diethyl brometo de amonio that transformation efficiency height, speed of reaction are fast.
Above-mentioned purpose of the present invention is achieved by the following technical programs:
The invention provides a kind of method of utilizing the synthetic octadecyl methyl diethyl brometo de amonio of microwave, be to be raw material with N methyldiethanol amine and bromo-octadecane, with n-hexyl alcohol or Pentyl alcohol is solvent, carries out microwave and reflux under power 400～600W, reaction 15～25min and obtaining.This moment, the octadecyl methyl diethyl brometo de amonio that obtained was thick product, by with acetone recrystallization several times after, suction filtration gets the brilliant white crystal, get final product after the drying highly purified octadecyl methyl diethyl brometo de amonio.
The reaction formula of synthetic octadecyl methyl dihydroxy ethyl brometo de amonio is as follows:
In the above-mentioned reaction, the mol ratio of N methyldiethanol amine and bromo-octadecane is 1: 1, and the ratio of the consumption of described solvent and N methyldiethanol amine or bromo-octadecane is 500～600ml/mol.The preferred n-hexyl alcohol of solvent, the ratio of its consumption and N methyldiethanol amine or bromo-octadecane are 535ml/mol.
Remove this, preferred microwave power and reaction times are respectively 570W and 25min.
Above-mentioned synthetic method is to influence microwave synthetic factor and test by choosing different solvents, reaction times, solvent volume, microwave power etc., transformation efficiency with N methyldiethanol amine is an index, the process test of many times draws after groping, and this method high conversion ground at short notice obtains highly purified octadecyl methyl diethyl brometo de amonio.
Compared with prior art, the present invention has following beneficial effect:
(1) synthetic method reaction times weak point provided by the present invention, energy consumption are still less compared with the traditional heating method, and speed of reaction has improved nearly 23 times.
(2) synthetic method transformation efficiency height provided by the present invention can reach more than 95%, and the raw material availability height has further been saved cost.
(3) synthetic method provided by the present invention can obtain highly purified product through simple recrystallization, and product purity reaches more than 99%, has obtained good product performance simultaneously.
In order to verify beneficial effect of the present invention, invention has also adopted following means that this synthetic method is assessed:
1. transformation efficiency is measured
Generate quaternary ammonium salt according to tertiary amine and hydrochloric acid reaction, tertiary amine has alkalescence, and quaternary ammonium salt does not have alkalescence, therefore makes the PH indicator with tetrabromophenol sulfonphthalein, comes the content of unhindered amina in the assaying reaction process, thereby draws the transformation efficiency of N methyldiethanol amine.Take by weighing the 1.0g reaction soln in the 100mL Erlenmeyer flask before and after the reaction, use the 5mL anhydrous alcohol solution, add 3～4 0.1% tetrabromophenol sulfonphthalein indicator, the hydrochloric acid-ethanol standard solution titration with 0.25mol/L is terminal point by blueness to yellow extremely then.Calculation formula is:
In the formula, V
0Be the hydrochloric acid-ethanol standardized solution volume that consumes before reacting, ml;
V
1Be the hydrochloric acid-ethanol standardized solution volume of reaction post consumption, ml.
2. purity check
According to the two-phase titration principle, (BPB) makes the two-phase indicator with tetrabromophenol sulfonphthalein, and ethylene dichloride is done to divide phase solvent, with cats product solution titration SDS standardized solution to be measured, shows blue to lower floor's solvent layer.
Accurately take by weighing the 0.1g sample, after water dissolution, constant volume is in the 500mL volumetric flask, as titrating solution.Pipette SDS standardized solution 5mL with transfer pipet and place Erlenmeyer flask, add deionized water 10mL, 10%Na
2CO
3Solution 0.5mL, 0.5g NaCl, 7 0.05% tetrabromophenol sulfonphthaleins and ethylene dichloride 10mL.Fully vibration is down with sample solution titration to be measured, is terminal point when being titrated to lower floor's ethylene dichloride and showing blueness.Do a blank assay by same operation.Be calculated as follows the massfraction of sample:
V in the formula
1Volume (mL) for sample solution that sample consumes;
V
0The volume (mL) of the sample solution that is consumed during for blank assay;
M is the relative molecular mass of sample; M is sample quality (g);
Ca, Va are the concentration (mol/L) and the volume (mL) of SDS standardized solution.
3. product performance are measured
Utilize the digital display melting point detector to measure the fusing point of product;
Utilize the full-automatic interfacial tensimeter of ZL2100 to measure the surface tension of product;
Adopt the dye well ultraviolet-visible spectrophotometry to measure the micelle-forming concentration of product.
Description of drawings
Fig. 1 represents the influence of differential responses time to combined coefficient of the present invention;
Fig. 2 represents the influence of different solvents capacity to combined coefficient of the present invention;
Fig. 3 represents the influence of different microwave to combined coefficient of the present invention;
Fig. 4 represents the thin-layer chromatogram behind the institute of the present invention sintetics recrystallization, and wherein the direction of arrow is the developping agent direction;
Fig. 5 represents the infrared absorpting light spectra behind the gained sintetics recrystallization of the present invention;
Fig. 6 represents gained sintetics of the present invention
1H NMR spectrogram
Fig. 7 represents the visible absorption spectra of gained sintetics of the present invention system under different OMDAB concentration
Fig. 8 represents the interaction of solvent volume of the present invention and microwave power;
Fig. 9 represents the interaction in solvent volume of the present invention and reaction times;
Figure 10 represents the interaction in microwave power of the present invention and reaction times;
Embodiment
Below further specify technical scheme of the present invention by specific embodiment.
Embodiment 1
With mol ratio is that 1: 1 N methyldiethanol amine (0.02mol) and bromo-octadecane (0.02mol) add in the Florence flask, measure 10ml ethanol, n-propyl alcohol, propyl carbinol, Pentyl alcohol, n-hexyl alcohol dissolving mixing respectively, at microwave power is 600W, carries out microwave under the condition of reaction times 25min and refluxes synthetic.
Assess the transformation efficiency of above-mentioned reaction, the result is as shown in table 1.
Table 1 solvent is to the influence of transformation efficiency
By the result as can be known, in above 5 reactions, reaction solution transfers yellow to gradually by colourless, and color is deepened gradually, viscosity increases.The color of product can directly reflect the transformation efficiency of reactant.Transformation efficiency is the highest when as can be seen from the above table, making solvent with n-hexyl alcohol.This may be because the strong and weak heat effect that can influence microwave of polarity of solvent, because the polarity of n-hexyl alcohol is less, the heat effect of microwave is just relatively poor, the micro-wave energy that solvent absorbing is less, make reactant obtain more energy, aggravated the reactant molecule motion, molecule and collision of molecules probability are increased, helped reaction and carry out.In addition since the reflux temperature of n-hexyl alcohol than other solvent height, reaction system can obtain more energy, the collision between the aggravation molecule promotes reaction to carry out, and therefore selects n-hexyl alcohol as the solvent that reacts.
Embodiment 2
With mol ratio is that 1: 1 N methyldiethanol amine (0.02mol) and bromo-octadecane (0.02mol) add in the Florence flask, measures 10ml n-hexyl alcohol mixed dissolution, under the microwave power of 600W, reacts 5,10,15,20 respectively, 25min.The results are shown in shown in Figure 1.
By the result as can be known, all can there be higher transformation efficiency in the reaction times more than 20min, and this is because along with time lengthening, the probability that collides between the molecule increases greatly, makes reaction be tending towards fully, and when the reaction times was 25min, transformation efficiency was 93.87%.Though the reaction times further prolonged afterwards, but the amplitude that transformation efficiency improves is little, and this may be because concentration of reactants reduces, and makes the gradient of reaction reduce, based on the consideration of production energy consumption, select the optimization range of 15～25min simultaneously as microwave irradiation time.
Embodiment 3
With mol ratio is that 1: 1 N methyldiethanol amine (0.02mol) and bromo-octadecane (0.02mol) add in the Florence flask, measures 8,9,10,11,12,15 respectively, the n-hexyl alcohol of 18ml, under the microwave power of 600W, and reaction 25min.The result as shown in Figure 2.
By the result as can be known, along with the increase of solvent volume, transformation efficiency increases, and transformation efficiency maximum when solvent volume is 11mL descends on the contrary but continue to increase the solvent volume transformation efficiency.This is that viscosity is too big because of solvent volume very little, is unfavorable for reaction, increases solvent volume, and the reactant uniform mixing makes that the probability of collision between the molecule increases, and helps reaction and carries out.But along with solvent volume continues to increase, solvent meeting absorption reaction system more energy makes reactant obtain energy and reduce, so the transformation efficiency of reactant descends.So, select the optimization range of 10～12ml as solvent volume.
Embodiment 4
With mol ratio is that 1: 1 N methyldiethanol amine (0.02mol) and bromo-octadecane (0.02mol) add in the Florence flask, measure 11ml n-hexyl alcohol mixed dissolution, react 25min respectively under the microwave power of 100W, 200W, 300W, 400W, 500W, 600W, 700W, 800W, the result as shown in Figure 3.
By the result as can be known, when irradiation power improved, the transformation efficiency of reactant obviously increased, and this is that reaction system obtains more energy because improve microwave power, and the energy that reactant absorbs increases, the aggravation of molecular motion state, and speed of reaction improves; When microwave power reaches 600W continuation raising, the reaction-ure conversion-age increasing degree is little, this may be because microwave power offers the energy of reaction system during for 600W can have been satisfied molecule and reach maximum rate, even improve power again, also can not continue to aggravate the molecular motion state.Therefore, select the optimization range of 400～600W as microwave power.
The comparison of microwave synthesis method of the present invention and traditional heating synthetic method:
Microwave synthesis method of the present invention: with mol ratio is that 1: 1 N methyldiethanol amine (0.02mol) and bromo-octadecane (0.02mol) add in the Florence flask, measures n-hexyl alcohol 10.7ml mixed dissolution, carries out the microwave back flow reaction under 570W.
The traditional heating method: with mol ratio is that 1: 1 N methyldiethanol amine (0.02mol) and bromo-octadecane (0.02mol) add in the Florence flask, measures n-hexyl alcohol 10.7ml mixed dissolution, evenly stirs until reaction complete substantially under condensing reflux.
Reaction finishes the transformation efficiency of back assaying reaction thing, and the result is as shown in table 2.
The comparison of the different synthesis techniques of table 2
The result shows that the traditional heating transformation efficiency reaches 88.56% needs 540min, and transformation efficiency reaches 95.30% need 25min under microwave exposure, and the reaction required time only is the former 4.63%, and speed of reaction has improved nearly 23 times.With traditional heating method contrast as can be known: microwave method is shorter than the traditional heating method reaction times, energy consumption still less, transformation efficiency is higher.
The analysis and characterization of product: the product of the synthetic gained of microwave method among the embodiment 5 is carried out following analysis:
1. tlc
Behind the thick product recrystallization 5 times, adopt the right product of tlc to analyze.Method is as follows: use the pencil drawing straight line as baseline at silica-gel plate apart from the about 0.5cm of end place, with kapillary 1.0% the product aqueous solution is carried out point sample at the baseline place that mark is crossed, again silica-gel plate baseline end is immersed in and launches in the pond (submergence highly is no more than baseline in the developping agent), with methyl alcohol is developping agent, allows methyl alcohol upwards be deployed into the 0.5cm place of thin plate upper end.From launch the pond, take out silica-gel plate, wait solvent evaporates on the silica-gel plate to fall after, develop the color with iodine staining, and with pencil sign colour developing spot.
A spot only appears in thin-layer chromatography such as Fig. 4 in the color atlas, illustrate that the product after the crystallization is an one matter.Simultaneously the product purity that records after the crystallization according to the two-phase titration principle is 99.06%.
2. ultimate analysis
The results of elemental analyses of sintetics sees Table 3.By table 3 as seen, C, H, N element massfraction and theoretical value difference are little, show that product purity is higher.
The results of elemental analyses of table 3 product
3. infrared absorption spectrum
With infrared absorption spectrometer the product (using the KBr compressing tablet) behind the recrystallization 5 times is done infrared absorption spectrum, the infrared absorpting light spectra of sintetics is seen Fig. 5.
By as can be known to the analysis of infrared absorpting light spectra, 3350cm
-1A near absorption peak that strong and wide absorption peak is the O-H stretching vibration that occurs, 2925cm
-1And 2853cm
-1Be the stretching vibration absorption peak of methyl and methylene radical, 1462cm
-1Near be CH
3, CH
2The unsymmetrically flexural vibration, 1392cm
-1Near be the vibration absorption peak of quaternary ammonium group, 1058cm
-1Neighbouring is the absorption peak of C-O formation vibration, 723cm
-1Near be the scissoring vibration absorption peak of methyl and methylene radical, and the C-Br key in the raw material do not show in collection of illustrative plates, so can this product of preliminary evaluation be octadecyl methyl dihydroxy ethyl brometo de amonio by infrared absorpting light spectra.
4. proton nmr spectra
Make solvent with acetone, mark in TMS does is done the proton nmr spectra of sintetics, Fig. 6 be sintetics proton nmr spectra (
1HNMR) figure.Right
1The analysis and the deduction of H NMR spectrum see Table 4.
Table 4
1The analysis and the deduction of H NMR spectrum
As seen from Figure 6,2.80 places are the dry inadequately less water peak that produces of sample, do not influence the judgement to product structure.As can be seen from Table 3, the ownership of each group and its structural formula meet substantially.
By
1H NMR, IR and ultimate analysis analysis-by-synthesis prove the structure of institute's sintetics and theoretic
Structure conforms to fully.
Embodiment 7
The performance analysis of product: the product of microwave synthesis method gained among the embodiment 5 is carried out following analysis:
1. surface tension
The quaternary ammonium salt solution of preparation 0.1% uses Boshan sea, Zibo to divide the ZL2100 of instrument plant type full-automatic interfacial tensimeter, adopts the platinum loop method to measure the quaternary ammonium salt solution surface tension.Recording its surface tension is 22.7Nm
-1, this as can be known tensio-active agent has the surface of good activity, can reduce the surface tension of water preferably, is a kind of novel efficient surfactant product.This may be because contain long alkyl chain in the molecular structure, makes this quaternary ammonium salt have stronger hydrophobic interaction, therefore can reduce the surface tension of water to a great extent.
2. micelle-forming concentration
Adopt the dye well ultraviolet-visible spectrophotometry to survey the micelle-forming concentration (CMC) of sintetics.Compound concentration 0～0.08mmolL
-1Each 50ml of quaternary ammonium salt solution, totally 16 samples, the concentration of eosin in each solution example (EY) is 0.025mmolL
-1Adopt ultraviolet spectrophotometer under 400～600nm, scan every 1nm, and each scanning curve is carried out the match of Gauss's multimodal, make the graph of a relation of product concentration and eosin master absorption peak peak width at half height after the match and see Fig. 7 with Origin7.5 software.
(the EY concentration fixed is 0.025mmolL at OMDAB-EY
-1) in the water solution system, when concentration was very little, OMDAB existed with molecularity, because the little EY of concentration mainly exists in solution with the unit molecule state, ultraviolet-visible absorption spectroscopy shows as EY aqueous solution absorption peak.If fixing EY concentration, OMDAB concentration in the increase system gradually, micelle progressively forms, EY progressively forms EY dimerization or polymer in order the water-wet side adsorption and enrichment and relative arrangement of micelle, spectral signature obviously changes, and shows as that main peak is subjected to displacement with acromion, the relative absorbancy with acromion of main peak changes and halfwidth changes.
By eosin master absorption peak halfwidth and OMDAB concentration relationship graphic representation as can be known, the main absorption peak halfwidth of eosin increases with the increase of OMDAB concentration, reaches 0.0318mmolL about OMDAB concentration
-1Shi Fasheng turnover, i.e. the micelle-forming concentration CMC=0.0318mmolL of OMDAB
-1
3.Krafft the point
Whether prepare 0.1% quaternary ammonium salt aqueous solution, be positioned over temperature and be lower than in 0 ℃ the saturated aqueous common salt, observing has crystal or solid matter to separate out.Found that do not have crystal or solid matter to separate out in the quaternary ammonium salt aqueous solution, the solution clear, the Krafft's point that product is described is less than 0 ℃.As seen this quaternary ammonium salt has good water-solubility, and this may be owing to contain 2 hydrophilic hydroxyls in the quaternary ammonium salt molecular structure, makes it have good water-solubility.
4. fusing point
Product after using WS-1 numeral fusing point instrument to crystallization carries out fusing point test, notes the data of incipient melting and fine melt, averages after repeatedly measuring.
Table 5 fusing point test result
The melting range that uses digital melting point detector to record octadecyl methyl dihydroxy ethyl brometo de amonio is 120.02～120.82 ℃, and the melting range of this product is 0.8 ℃, in 1 ℃, can illustrate that product has higher purity.Get repeatedly average value measured, the fusing point of this material is 120.56 ℃.
Embodiment 8
The optimization of synthesis technique and response surface analysis:
Adopt Design Expert7.0 software that the synthesis condition of quaternary ammonium salt has been set up numerical relationship model between a transformation efficiency and each factor.Determine the span of each factor according to the experiment of single factor result, adopt Design Expert7.0 software design experimental program, carry out 3 factors, 3 levels (as table 6) of microwave power, reaction times, solvent volume, regression model is set up in the response surface analysis of totally 20 experimental points experiment.Table 3 is single level of factor table of response surface experiment, and table 7 is the response surface experimental result.
Single level of factor table of table 6 response surface experiment
Table 7 response surface experimental result
According to experimental result, the reaction conditions mathematical model of being set up by Design Expert 7.0 softwares is: R1 (%)=-189.7835+6.33009A+31.47559B-0.15985C+0.23650 * AB-(2.87000 * 10
-3) * AC+ (5.0750000 * 10
-3) * BC-0.10589A
2-1.41587 * B
2+ (2.460874 * 10
-4) * C
2
In the formula: R1 is a transformation efficiency, and A is quantity of solvent (mL), and B is power (W), and C is reaction times (min).
The mathematical model of being set up is carried out variance analysis, the results are shown in Table 8." Prob＞F " is if value, illustrates that corresponding factor to the influence of response face amount significantly less than 0.05.As shown in Table 8, " Prob＞F " of above-mentioned mathematical model is 0.0001, shows this mathematical model highly significant.The interaction of time, solvent volume, power, solvent volume and power, solvent volume and time belongs to the significant factor of influence.3 single factors are followed successively by the influence of transformation efficiency: microwave irradiation time＞quantity of solvent＞microwave power.By Fig. 8-10 as can be seen, microwave irradiation time and microwave power are bigger to the experimental result influence.
The analysis of variance table of table 8 quadratic power model
Carry out the parameter optimization analysis according to the mathematical model that Design Expert 7.0 softwares are set up, the best synthesis technique that obtains is: solvent volume 10.7ml, microwave power 570W, reaction times 25min.Doing 3 times by the processing parameter after the above-mentioned optimization verifies, obtain transformation efficiency and be respectively 95.36%, 95.24%, 95.31%, the mean value of transformation efficiency is 95.30%, very approaching with predictor, show that the synthetic technological condition of the mathematical model optimizing octadecyl methyl diethyl brometo de amonio that uses the foundation of response surface analysis method is feasible.
Claims (9)
1. the method for a synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave, it is characterized in that: with N methyldiethanol amine and bromo-octadecane is raw material, is solvent with n-hexyl alcohol or Pentyl alcohol, reacts under microwave condition.
2. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 1, its feature is being: described microwave condition is microwave power 400～600W.
3. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 2, it is characterized in that: described microwave power is 570W.
4. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 1, its feature is being: the described reaction times is 15～25min.
5. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 4, it is characterized in that: the described reaction times is 25min.
6. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 1, it is characterized in that: the mol ratio of described N methyldiethanol amine and bromo-octadecane is 1: 1.
7. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 1, it is characterized in that: the ratio of the consumption of described solvent and N methyldiethanol amine or bromo-octadecane is 500～600ml/mol.
8. the method for synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave as claimed in claim 1, it is characterized in that: described solvent is a n-hexyl alcohol, the ratio of its consumption and N methyldiethanol amine or bromo-octadecane is 535ml/mol.
9. as the method for the described synthesizing octadecyl methyl dihydroxyethyl ammonium bromide by using microwave of the arbitrary claim of claim 1～8, it is characterized in that: the gains after finish the reaction back are also through using acetone recrystallization, suction filtration and drying again.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102381987A (en) * | 2011-09-01 | 2012-03-21 | 广州科技贸易职业学院 | Solvent-free synthesis method for octodecyl methyl dihydroxy ethyl ammonium bromide |
| CN112986306A (en) * | 2019-12-16 | 2021-06-18 | 北京泓泰天诚科技有限公司 | Memory, and method, device and equipment for measuring purity of N-methyldiethanolamine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01238565A (en) * | 1988-03-18 | 1989-09-22 | Oki Electric Ind Co Ltd | High-molecular-weight thermotropic liquid crystal and amphiphatic resin material |
-
2010
- 2010-05-21 CN CN2010101863255A patent/CN101898971A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01238565A (en) * | 1988-03-18 | 1989-09-22 | Oki Electric Ind Co Ltd | High-molecular-weight thermotropic liquid crystal and amphiphatic resin material |
Non-Patent Citations (3)
| Title |
|---|
| MICHAEL ARKAS ET AL: "Smectic Mesophases from Dihydroxy Derivatives of Quaternary Alkylammonium Salts", 《CHEM. EUR. J.》 * |
| 张学同等: "N-甲基二乙醇胺三个季铵盐衍生物的合成与表征", 《合成化学》 * |
| 毛桃嫣等: "十二烷基甲基二羟乙基溴化铵的微波合成及性能研究", 《精细化工》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102381987A (en) * | 2011-09-01 | 2012-03-21 | 广州科技贸易职业学院 | Solvent-free synthesis method for octodecyl methyl dihydroxy ethyl ammonium bromide |
| CN112986306A (en) * | 2019-12-16 | 2021-06-18 | 北京泓泰天诚科技有限公司 | Memory, and method, device and equipment for measuring purity of N-methyldiethanolamine |
| CN112986306B (en) * | 2019-12-16 | 2023-11-24 | 北京泓泰天诚科技有限公司 | Purity determination method, device and equipment for memory and N-methyldiethanolamine |
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