CN109553536A - A kind of synthetic method of fatty alkyl dimethylbenzyl based quaternary ammonium salt - Google Patents
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Abstract
The invention discloses a kind of preparation methods of fatty alkyl dimethylbenzyl based quaternary ammonium salt.The preparation method of the fatty alkyl dimethylbenzyl based quaternary ammonium salt comprising fatty alkyl dimethyl tertiary amine and halogenation benzyl at 30~70 DEG C, are carried out salt-forming reaction in organic solvent by following steps；Wherein, in the fatty alkyl tertiary amine, the R is C6H13~C22H45；In the halogenation benzyl, " halogen " is chlorine, bromine or iodine；The organic solvent is one of methanol, ethyl alcohol, normal propyl alcohol, isopropanol, acetone and acetonitrile or a variety of.Preparation method high income of the invention, up to 90% or more；Purity is high, up to 99% or more, water content is low, it can be achieved that product appearance form is good, the simple effect of post-processing, can reduce energy consumption, be suitble to industrialized production.
Description
Technical field
The present invention relates to a kind of synthetic methods of fatty alkyl dimethylbenzyl based quaternary ammonium salt.
Background technique
Fatty alkyl dimethylbenzyl based quaternary ammonium salt is a kind of cationic surfactant, belongs to non oxidizing bactericide, tool
There is very efficient sterilizing ability.The method of synthctic fat alkyldimethylbenzylammonium quaternary ammonium salt can be divided into two kinds at present.It is a kind of
It is to be synthesized with fatty alkyl dimethyl tertiary amine with halogenation benzyl；Another kind is with halogenated aliphatic alkane and N, the conjunction of N- dimethyl benzylamine
At.
Document 1 (CN 1267405C), which is disclosed, synthesizes dodecylbenzyl chlorine with benzyl chloride with corresponding tertiary amine mixture
Change the mixture of ammonium and myristyl benzyl ammonium chloride.It should be pointed out that there are many drawbacks for this method.Firstly, being terrible
To the higher alkyldimethylbenzylammonium quaternary ammonium salt of purity, this method has selected the benzyl chloride of high-temperature pressure distil(l) as reaction
Object, this undoubtedly increases energy consumption of reaction, improves the cost of reaction.Extremely toxic substance benzyl chloride content highest in final product reaches unexpectedly
4.82%.
Document 2 (US 5414124) reports the in the mixed solvent synthesis of alkyl dimethylbenzyl based quaternary ammonium salt in glycol and water
The method of solution.The disadvantages of the method are as follows reaction temperature is excessively high, the concentration of quaternary ammonium salt is lower in final reaction product.
Document 3 (RU 2123491) is reported with the mixed tertiary amine (fatty alkyl two of mainly 12-16 carbon chain lengths
Methyl tertiary amine) and benzyl chloride alkyl diol and water in the mixed solvent, reaction finally obtain concentration be 50-80% fatty alkyl
Dimethyl benzyl quaternary ammonium salt solution.But the final product purity of this method is not high, is mixture, it is difficult to by the pure of each component
Compound separates.When post-processing, higher temperature is needed to remove wherein solvent, leads to the shade deviation of product in this way, be in yellow, with
And contain the reactants such as untreated complete benzyl chloride.
Although document 4 (CN 102807494A) provides a kind of method of synthctic fat zephiran.
But anhydride is prepared in this method that purity is poor, easy to absorb moisture.And disclosed embodiment 1 operates in the method, and ten
The molar ratio of dialkyl dimethyl tertiary amine and benzyl chloride is 1:0.95, i.e. Dodecyl Dimethyl Amine is excessive, but
In method disclosed in CN 102807494A, there is no disclose specific purification step.And the product of 174.4kg is finally obtained, it presses
According to the purity 98.8% of final product, calculating its foreign body content is about 2.09kg (174.4kg*1.2%)；But it feeds intake
In, excessive tertiary amine has 5.11kg (24mol), is far longer than 2.09kg's.In addition from disclosed reaction and last handling process point
Analysis, system does not have material loss, but yield is only 90.3%, and purity but reaches 98% or more, it should be its undisclosed anhydride
Purification process.If the complete raw material of unreacted does not have purification process, the purity for causing product final is relatively low, and easily inhales
Tide, and the product that this method is produced is not able to satisfy medicinal demand.And since purity is not high enough, it is improved in post-processing
The stability of product joined a certain amount of water, and the water content of product is caused to increase, net purity decline, and product viscosity
Greatly, slice crushing need to be carried out with slicer, it is not easy to handle.
Document 5 (CN 101525295), which also discloses, uses urea as solvent synthctic fat zephiran
Method.But this method reaction temperature is high (130 DEG C), the quaternary ammonium salt content in final products is low, also containing untreated molten
Agent urea is not suitable with the production of large-scale.
In document 6 (journal of applied biomedicine 12 (2014) 245-253), give using fourth
Ketone makees solvent, the method that crystallization prepares fatty alkyl dimethylbenzyl based quaternary ammonium salt.But this method, last post-processing need
In -30 DEG C of crystallization 12h.This more harsh condition is industrially worthless.And final product has the crystallization water, with
Document 4 is similar, and the water content for having resulted in product increases, net purity decline.
In document 7 (J.Phys.Chem., 1990,94 (1), 381-387), gives and ethyl alcohol is used to synthesize as solvent,
And use the method for ethyl acetate, ethyl acetate+ethyl alcohol or crystallizing from ether.But need to carry out 3 to 4 knots in this method
It is brilliant.It is in actual production and undesirable which increase the operating procedure of production.
Also have with the method for halogenated aliphatic alkane and N, N- dimethyl benzylamine synthctic fat alkyldimethylbenzylammonium quaternary ammonium salt
Document report (Kamil Kuca et al.Preparation of Benzalkonium Salts Differing in the
Length of a Side Alkyl Chain；Molecules 2007,12,2341-2347；et al.A general
method for the quaternization of N,N-dimethyl benzylamines with long chain n-
alkylbromides；J.Appl.Biomed.2004,2,195-198).But this method is only suitable for preparing fatty alkyl two
Methylbenzyl bromide.Since chloro fat alkane is weaker than the activity of bromo fat alkane, so the process for forming quaternary ammonium salt compares
Difficulty, thus it is low with this method synthctic fat alkyldimethylbenzylammonium villaumite yield.
In summary the prior art analyze, at present the method for synthctic fat alkyldimethylbenzylammonium quaternary ammonium salt be largely by
Tertiary amine mixture is reacted with benzyl chloride, but the purity of universal final product is not high, contains a large amount of unreacting material
And benzyl alcohol, the related substance such as benzaldehyde, it needs further to refine the standard that can be only achieved pharmaceutical grade.And it is prepared
Fatty alkyl dimethylbenzyl based quaternary ammonium salt be mostly yellow glue or cake mass, subsequent weighing use when very not side
Just.
Therefore needing to develop a kind of fatty alkyl dimethylbenzyl based quaternary ammonium salt obtained with high purity, related, substance is few, contains
Water is few, and product appearance form is good, easy-to-handle preparation method.
Summary of the invention
The technical problem to be solved by the present invention is in order to overcome fatty alkyl dimethylbenzyl based quaternary ammonium salt in the prior art
Preparation method that there are yields is low, containing toxic by-products, purity is low, water content is high, post-processing is unstable, easy to change etc. scarce
It falls into, and provides a kind of preparation method of fatty alkyl dimethylbenzyl based quaternary ammonium salt.Preparation method high income of the invention, purity
Height, water content is low, and reaction temperature is low, it can be achieved that product appearance form is good, the simple effect of post-processing, can reduce energy consumption, fit
Close industrialized production.
The present invention provides a kind of preparation methods of fatty alkyl dimethylbenzyl based quaternary ammonium salt comprising following steps,
In organic solvent, at 30~70 DEG C, fatty alkyl dimethyl tertiary amine and halogenation benzyl are subjected to salt-forming reaction；
Wherein, in the fatty alkyl dimethyl tertiary amine, the R is C6~C22Alkyl；
In the halogenation benzyl, " halogen " is chlorine, bromine or iodine；
The organic solvent is one of methanol, ethyl alcohol, normal propyl alcohol, isopropanol, acetone and acetonitrile or a variety of.
In the fatty alkyl dimethyl tertiary amine, the R is preferably C6~C22Even number alkyl, more preferably for
C12H25、C14H29Or C16H33Straight chained alkyl.
The molar ratio of the fatty alkyl dimethyl tertiary amine and the halogenation benzyl can be such salt-forming reaction of this field
The molar ratio of middle conventional molar ratio, heretofore described fatty alkyl dimethyl tertiary amine and the halogenation benzyl is preferably
1:(0.9~1.1), it is more preferably 1:1.
The dosage of the organic solvent can be the dosage of such salt-forming reaction of this field routine, and heretofore described has
The mass ratio of solvent and the fatty alkyl dimethyl tertiary amine is preferably (2~5): 1, it is more preferably (3~4): 1.
The salt-forming reaction preferably carries out in anhydrous conditions, and described is anhydrous with this field routine, such as not
Influence reaction.
The temperature of the salt-forming reaction is preferably 40~60 DEG C, is more preferably 50 DEG C.
The salt-forming reaction preferably carries out under an inert atmosphere；The inert atmosphere be preferably nitrogen, argon and
One of helium is a variety of.
In the salt-forming reaction, the process of the reaction can be using the routine monitoring method (example in this field
Such as TLC, HPLC or NMR) it is monitored, as reaction end when generally being disappeared using halogenation benzyl compound or no longer being reacted.The present invention
In, the time of the salt-forming reaction is preferably 3~5h.
The salt-forming reaction may also include following post-processing step: it is after reaction, cooling, solid is precipitated；Compared with
Goodly after reaction, reaction system is cooled to -10 DEG C~10 DEG C, and crystallization filters.
On the basis of common knowledge of the art, above-mentioned each optimum condition, can any combination to get each preferable reality of the present invention
Example.
The reagents and materials used in the present invention are commercially available.
The positive effect of the present invention is that: preparation method high income of the invention, up to 90% or more；Purity is high,
Up to 99% or more, water content is low, it can be achieved that product appearance form is good, the simple effect of post-processing, can reduce energy consumption, be suitble to
Industrialized production.
Detailed description of the invention
Fig. 1 is that the HPLC of dodecyl benzyl dimethyl ammonium chloride schemes
Fig. 2 is dodecyl benzyl dimethyl ammonium chloride1H NMR figure
Specific embodiment
The present invention is further illustrated below by the mode of embodiment, but does not therefore limit the present invention to the reality
It applies among a range.In the following examples, the experimental methods for specific conditions are not specified, according to conventional methods and conditions, or according to quotient
The selection of product specification.
The preparation of 1 hexyl dimethylbenzyl ammonium bromide of embodiment
The hexyl dimethyl tertiary amine of 4.00kg (31.0mol) is added in 50L reaction kettle, 5.83kg's (34.1mol)
The isopropanol of cylite and 20.00kg stirs 3h at 70 DEG C.Then -10 DEG C are cooled to.After solid precipitation, filtering, dry
8.61kg white solid, total recovery 92.6%.Hexyl dimethylbenzyl ammonium bromide purity is 99.4%.
The preparation of 2 octyl dimethyl benzyl ammonium chloride of embodiment
The octyl dimethyl tertiary amine of 4.50kg (28.7mol) is added in 50L reaction kettle, 3.81kg's (30.1mol)
The acetonitrile of benzyl chloride and 18.00kg stirs 5h at 50 DEG C.Then 10 DEG C are cooled to.After solid precipitation, filtering, dry
7.48kg white solid, total recovery 91.9%.Octyl dimethyl benzyl ammonium chloride purity is 99.5%.
The preparation of 3 decyl dimethyl benzyl ammonium iodide of embodiment
The decyl dimethyl tertiary amine of 4.00kg (21.6mol) is added in 50L reaction kettle, 4.48kg's (20.5mol)
The methanol of iodate benzyl and 12.00kg stirs 3h at 60 DEG C.Then -10 DEG C are cooled to.After solid precipitation, filtering, dry
7.70kg white solid, total recovery 93.2%.Decyl dimethyl benzyl ammonium iodide purity is 99.3%.
The preparation of 4 dodecyl benzyl dimethyl ammonium chloride of embodiment
The Dodecyl Dimethyl Amine of 100.00kg (469.5mol), 62.40kg are added in 1000L reaction kettle
The benzyl chloride of (493.0mol) and the acetone of 300.00kg stir 3h at 40 DEG C.Then it is cooled to 0 DEG C.After solid precipitation, mistake
Filter, dry 145.88kg white solid, total recovery 92.5%.Dodecyl benzyl dimethyl ammonium chloride purity is
99.6%.
The preparation of 5 dodecyl benzyl dimethyl ammonium chloride of embodiment
The Dodecyl Dimethyl Amine of 100.00kg (469.5mol), 59.42kg are added in 1000L reaction kettle
The benzyl chloride of (469.5mol) and the isopropanol of 400.00kg stir 5h at 30 DEG C.Then 5 DEG C are cooled to.After solid precipitation,
Filtering, dry 147.30kg white solid, total recovery 92.4%.Dodecyl benzyl dimethyl ammonium chloride purity is
99.7%.
The preparation of 6 myristyl benzyl dimethyl ammonium chloride of embodiment
The dodecyldimethylamine base tertiary amine of 75.00kg (311.2mol), 35.45kg are added in 500L reaction kettle
The benzyl chloride of (280.1mol) and the ethyl alcohol of 250.00kg stir 5h at 40 DEG C.Then -5 DEG C are cooled to.After solid precipitation,
Filtering, dry 94.00kg white solid, total recovery 91.3%.Myristyl benzyl dimethyl purity of ammonia chloride is
99.6%.
The preparation of 7 myristyl benzyl dimethyl ammonium chloride of embodiment
The dodecyldimethylamine base tertiary amine of 75.00kg (311.2mol), 37.40kg are added in 500L reaction kettle
The benzyl chloride of (295.6mol) and the acetonitrile of 200.00kg stir 3h at 50 DEG C.Then it is cooled to 0 DEG C.After solid precipitation, mistake
Filter, dry 98.31kg white solid, total recovery 90.5%.Myristyl benzyl dimethyl purity of ammonia chloride is 99.5%.
The preparation of 8 cetalkonium chloride of embodiment
The hexadecyldimethyl benzyl ammonium tertiary amine of 7.00kg (26.0mol), 3.36kg (26.5mol) are added in 50L reaction kettle
Benzyl chloride and 17.50kg normal propyl alcohol, stir 3h at 50 DEG C.Then -5 DEG C are cooled to.After solid precipitation, filter, it is dry
Obtain 9.47kg white solid, total recovery 92.1%.Cetalkonium chloride purity is 99.5%.
The preparation of 9 cetalkonium chloride of embodiment
The hexadecyldimethyl benzyl ammonium tertiary amine of 7.00kg (26.0mol), 3.22kg (25.5mol) are added in 50L reaction kettle
Benzyl chloride and 25.00kg methanol, stir 4h at 30 DEG C.Then -5 DEG C are cooled to.After solid precipitation, filtering, dry
9.16kg white solid, total recovery 90.9%.Cetalkonium chloride purity is 99.6%.
The preparation of 10 octadecyl dimethyl benzyl ammonium bromide of embodiment
The octadecyldimethyl tertiary amine of 8.00kg (26.9mol), 4.38kg (25.6mol) are added in 50L reaction kettle
Cylite and 16.00kg acetonitrile, stir 3h at 60 DEG C.Then 10 DEG C are cooled to.After solid precipitation, filtering, dry
11.14kg white solid, total recovery 93.0%.Octadecyl dimethyl benzyl ammonium bromide purity is 99.4%.
The preparation of 11 eicosyl dimethyl benzyl ammonium iodide of embodiment
The eicosyl dimethyl tertiary amine of 4.00kg (12.3mol), 2.76kg (12.7mol) are added in 50L reaction kettle
Iodate benzyl and 20.00kg acetone, stir 3h at 40 DEG C.Then 5 DEG C are cooled to.After solid precipitation, filtering, dry
6.18kg white solid, total recovery 92.5%.Eicosyl dimethyl benzyl ammonium iodide purity is 99.6%.
The preparation of 12 docosyl dimethyl benzyl ammonium chloride of embodiment
The docosyl dimethyl tertiary amine of 6.00kg (17.0mol), 2.10kg are added in 50L reaction kettle
The benzyl chloride of (16.7mol) and the ethyl alcohol of 21.00kg stir 4h at 50 DEG C.Then it is cooled to 0 DEG C.After solid precipitation, mistake
Filter, dry 7.27kg white solid, total recovery 90.8%.Docosyl dimethyl benzyl ammonium chloride purity is
99.5%.
Comparative example 1
Comparative result is carried out according to 1 disclosure of that of embodiment of CN 102807494A.
Comparative example 2
It is carried out according to the method in document " Journal of applied biomedicine 12 (2014) 245-253 "
The preparation of dodecyl benzyl dimethyl ammonium chloride, compares.Specific step is as follows: 21.3g is added in 250mL flask
It is anti-to be heated to 80 DEG C of reflux for (0.1mol) Dodecyl Dimethyl Amine, 12.6g (0.1mol) benzyl chloride and 100mL butanone
Answer 12h.Then 1.8mL water is added, continues back flow reaction 6h.Then -30 DEG C of crystallisation by cooling 12h are cooled to.Crude product was passed through
It is dried under reduced pressure after filter, obtains the dodecyl benzyl dimethyl ammonium chloride containing two molecular crystalline water of 32.5g, yield is
96.0%, purity 95.3%, moisture 9.6%.
Comparative example 3
It is carried out according to the method in document " Journal of applied biomedicine 12 (2014) 245-253 "
The preparation of dodecyl benzyl dimethyl ammonium chloride is that water is added without in last handling process with 2 difference of comparative example, is carried out
Comparison.Specific step is as follows: 21.3g (0.1mol) Dodecyl Dimethyl Amine, 12.6g being added in 250mL flask
(0.1mol) benzyl chloride and 100mL butanone are heated to 80 DEG C of back flow reaction 18h.Then -30 DEG C of crystallisation by cooling 12h are cooled to.
Crude product is dried under reduced pressure after filtering, obtains the dodecyl benzyl dimethyl ammonium chloride without containing the crystallization water of 32.7g, is received
Rate is 90.4%, purity 94.1%, moisture 0.8%.
Comparative example 4
According to document, " J.Phys.Chem., 1990,94 (1), the method in 381-387 " carry out dodecyl dimethyl benzyl
The preparation of ammonium chloride, compares.Specific step is as follows: 21.3g (0.1mol) dodecyl two being added in 250mL flask
Methyl tertiary amine, 12.6g (0.1mol) benzyl chloride and 100mL dehydrated alcohol, are heated to 80 DEG C of back flow reaction 36-48h.Reaction knot
Shu Hou, solvent evaporated and unreacted reactant.Crude product is crystallized 3 times with ethyl acetate.It is dried under reduced pressure, obtains 21.80g dodecyl two
Methylbenzyl chloride solid.Yield is 64.3%, purity 99.3%, moisture 0.9%.
Comparative example 5
According to document " Molecules 2007,12,2341-2347 " and " J.Appl.Biomed.2004,2,195-198 "
In method carry out dodecyl benzyl dimethyl ammonium chloride preparation, compare.Specific step is as follows: in 50mL flask
1.0g (0.007mol) dimethyl benzylamine, 2.0g (0.01mol) chlorinated dodecane and 25mL dehydrated alcohol is added, is heated to 80
DEG C back flow reaction 28h.After reaction, solvent evaporated.Crude product carries out column chromatography, and eluent is chloroform/methanol (100/1).
It is finally dried under reduced pressure, obtains 0.84g dodecyl benzyl dimethyl ammonium chloride solid.Yield is 35.3%, and purity is
99.2%, moisture 0.9%.
Effect example 1
The inspection of moisture and purity is carried out to embodiment 1-12, comparative example 1-5, as a result such as table 1.
The Comparative result of 1 embodiment 1-6 of table, comparative example 1-4
In table 1, purity data be with the Mass Calculation of fatty alkyl dimethylbenzyl based quaternary ammonium salt dry product, and it is aqueous
It is unrelated to measure size.It can be seen that from the experimental data in table 1 by fatty alkyl dimethylbenzyl based quaternary ammonium salt produced by the invention
Yield is up to 90% or more, and for water content less than 1.0%, purity may be up to 99% or more.
Disclosed in 102807494 A of CN in method, do not disclose specific purification step.According to finally obtaining
The product of 174.4kg and the water 18.6kg of addition are calculated, and the water content of product is 10.7%.
Comparative example 2, although yield 96% is higher than the present invention, its purity 95.3% is well below the present invention；It is right
Than embodiment 3, water not being added on the basis of comparative example 2 and is crystallized, total recovery is 90.4% close with the present invention,
Purity 94.1% is far below the present invention.But the concrete operation step of comparative example 3, compared with the present invention, the reaction time is more
Long, reaction temperature is higher.Speculate that reaction temperature is excessively high or the reaction time is too long, will lead to the raw material decomposes of part, so right
Purity than 3 final product of embodiment is much smaller than the present invention.Most importantly, crystallization temperature needs in comparative example 2 and 3
At -30 DEG C, need to be cooled down with liquefied ammonia in the industrial production, and the cooling of -10 DEG C~10 DEG C of the present invention only needs to make
Use brine ice.The two is compared, the former cost is 5~10 times of the latter.
Comparative example 4 and 5, due to the change of method for crystallising and solvent either starting material, yield is below this
Invention.
Claims (8)
1. a kind of preparation method of fatty alkyl dimethylbenzyl based quaternary ammonium salt, which is characterized in that include the following steps, organic molten
In agent, at 30~70 DEG C, fatty alkyl dimethyl tertiary amine and halogenation benzyl are subjected to salt-forming reaction；
Wherein, in the fatty alkyl dimethyl tertiary amine, the R is C6~C22Alkyl；
In the halogenation benzyl, " halogen " is chlorine, bromine or iodine；
The organic solvent is one of methanol, ethyl alcohol, normal propyl alcohol, isopropanol, acetone and acetonitrile or a variety of.
2. preparation method as described in claim 1, which is characterized in that in the fatty alkyl dimethyl tertiary amine, the R
For C6~C22Even number alkyl；
And/or the molar ratio of the fatty alkyl dimethyl tertiary amine and the halogenation benzyl is 1:(0.9~1.1)；
And/or the mass ratio of the organic solvent and the fatty alkyl dimethyl tertiary amine is (2~5): 1.
3. preparation method as described in claim 1, which is characterized in that the R is C12H25、C14H29Or C16H33Straight chain alkane
Base；
And/or the molar ratio of the fatty alkyl dimethyl tertiary amine and the halogenation benzyl is 1:1；
And/or the mass ratio of the organic solvent and the fatty alkyl dimethyl tertiary amine is (3~4): 1.
4. preparation method as claimed in any one of claims 1 to 3, which is characterized in that the salt-forming reaction is in anhydrous conditions
It carries out；
And/or the temperature of the reaction is 40~60 DEG C；
And/or the salt-forming reaction carries out under an inert atmosphere；
And/or the time of the salt-forming reaction is 3~5h.
5. preparation method as claimed in claim 4, which is characterized in that the temperature of the reaction is 50 DEG C；
And/or the inert atmosphere is one of nitrogen, argon and helium or a variety of.
6. preparation method as claimed in claim 4, which is characterized in that the salt-forming reaction may also include following post-processing step
It is rapid: it is after reaction, cooling, solid is precipitated.
7. preparation method as claimed in claim 6, which is characterized in that after reaction, reaction system is cooled to -10 DEG C~10
DEG C, crystallization, filtering.
8. preparation method as claimed in claim 7, which is characterized in that after reaction, reaction system is cooled to -5 DEG C~5
DEG C, crystallization filters, dry.
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| CN113527106B (en) * | 2020-04-16 | 2023-10-20 | 广东先强药业有限公司 | Preparation method of pharmaceutical grade sitagliptin chloride |
| CN115124428A (en) * | 2022-07-20 | 2022-09-30 | 山东鑫泰水处理技术股份有限公司 | Composite bactericide containing dialkyl methyl benzyl quaternary ammonium salt and preparation method thereof |
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