CN106916068B - A kind of simple and convenient benzalkonium chloride production method - Google Patents
A kind of simple and convenient benzalkonium chloride production method Download PDFInfo
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- CN106916068B CN106916068B CN201710182475.0A CN201710182475A CN106916068B CN 106916068 B CN106916068 B CN 106916068B CN 201710182475 A CN201710182475 A CN 201710182475A CN 106916068 B CN106916068 B CN 106916068B
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- benzalkonium chloride
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- ethyl acetate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
Abstract
The invention discloses a kind of production methods of benzalkonium chloride monomer, this method is by 12 (14 or 16) alkyl dimethyl tertiary amides and benzyl chloride with 1:(1~1.4) after the ratio of (mol/mol) mixing insulation reaction 8-10 hours under conditions of ethyl acetate, after fully reacting, it is cooled to crystal precipitation, it is filtered after crystal is precipitated completely, filter cake is added ethyl acetate and is recrystallized, and crystallization filters afterwards completely, is drying to obtain.Using the present invention, reaction yield is up to 98%, and obtained benzalkonium chloride purity is up to 99%, which can be directly used in pharmaceuticals industry.When preparing high-purity benzalkonium chloride using the present invention, raw material used does not need to refine, it is only necessary to which single step reaction reduces feed purification step, and conventional reaction vessel is used only it is achieved that therefore the present invention can effectively reduce production cost in the present invention.
Description
Technical field
The present invention relates to technology of fine chemicals, it is more particularly related to a kind of, the present invention relates to one kind
Simple and convenient benzalkonium chloride production method.
Background technique
Benzalkonium chloride is a kind of cationic surfactant, also known as geramine, has wide spectrum, efficient sterilization algae removal energy
Power can efficiently control bacterium algae breeding and foundry loam growth in water, and have good sludge stripping effect and certain dispersion, seep
Effect thoroughly, at the same have it is certain deoil, deodorizing capability and corrosion inhibition, in recent years, about grinding for benzalkonium chloride antibacterial activity
Study carefully report it is increasing, benzalkonium chloride in pharmaceuticals industry application show huge potentiality.
Currently, the preparation method of benzalkonium chloride is using Dodecyl Dimethyl Amine and benzyl chloride as raw material, by benzyl chloride
It is dripped into Dodecyl Dimethyl Amine solution dropwise, to obtain the final product, obtained benzalkonium chloride is mostly technical grade to insulation reaction,
It is dfficult to apply to field of medicaments.Dodecyl Dimethyl Amine and benzyl chloride must be subjected to essence before the benzalkonium chloride preparation of pharmaceutical grade
System, the production method process is complicated, and instrument and equipment requires height, and many medicinal benzalkonium chloride production companies can not prepare benzene
Oronain is pricked, the cost of benzalkonium chloride medical product is increased.
Summary of the invention
The purpose of the present invention is to provide a kind of production methods of simple and convenient benzalkonium chloride.This process simplify benzene to prick chlorine
The production procedure of ammonium, reduces equipment requirement, improves production efficiency, reduces the production cost of medicinal benzalkonium chloride.
In order to achieve the above-mentioned object of the invention, the invention adopts the following technical scheme:
A, it is dissolved in ethyl acetate after mixing alkyl dimethyl tertiary amide according to a certain percentage with benzyl chloride；
B, mixed liquor is pumped into 300L glassed steel reaction vessels, opens the agitating device of reaction kettle and the steaming of TCU control
The heating device of vapour heating, system after insulation reaction 7-10 hours, are naturally cooling to crystal and analyse completely under the conditions of 70-100oC
It is filtered after out；Divide 2-5 cleaning crystal with ethyl acetate during filtering, retains filter cake；
C, by it is above-mentioned filter rear dissolution of crystals heat ethyl acetate in recrystallize, taken out after crystal is precipitated completely
Filter, crystal are dried under vacuum to constant weight under the conditions of -1.5Mpa, 60 DEG C up to high-purity pharmaceutical grade benzalkonium chloride monomer.
Further, alkyl dimethyl tertiary amide can be Dodecyl Dimethyl Amine, dodecyldimethylamine in the step A
Base tertiary amine and hexadecyldimethyl benzyl ammonium tertiary amine.
Further, alkyl dimethyl tertiary amide and benzyl chloride mixing and ratio are 1:(1~1.4 in the step A) (mol/
Mol).
Further, temperature of the mixed liquor in insulation reaction is 70-100oC in the step B, and the insulation reaction time is
7-10 hours.
Further, heating device described in the step B is the steam-heated collet of TCU control.
Further, in the step B ethyl acetate wash number in final crystal by fatty alkyl dimethyl tertiary amine
It is lower than subject to 0.005% with benzyl chloride content.
Further, the temperature in ethyl acetate hot in the step C is 40~70 DEG C.
Further, ethyl acetate additional amount, which is subject to, in recrystallizing in the step C is completely dissolved crystal.
Further, be: the purity of the resulting benzalkonium chloride of step C is greater than 99%.
A kind of production method of simple and convenient benzalkonium chloride of the present invention has the advantages that.
For a kind of production method of simple and convenient benzalkonium chloride of the present invention compares traditional handicraft, benzene obtained is pricked
Oronain purity is up to that 99%, impurity is few, and use is safe, can be effectively applied in field of medicaments；The present invention is using the side such as recrystallization
Method purifies benzalkonium chloride, can be effectively reduced production cost；Benzalkonium chloride yield prepared by the present invention is up to 98%, reduces
The generation of side reaction, reduces production cost；In addition, the invention uses dodecyldimethylamine base tertiary amine, hexadecane
Base dimethyl tertiary amine is raw material to produce benzalkonium chloride, and raw material used does not need to refine, it is only necessary to which single step reaction reduces raw material
Purification step improves production efficiency, and conventional reaction vessel is used only it is achieved that therefore the present invention can have in the present invention
The reduction production cost of effect.
Specific embodiment
Below with reference to specific embodiment to a kind of production method of simple and convenient benzalkonium chloride of the present invention do into
The elaboration of one step, it is more complete, accurate and deep to help those skilled in the art to have inventive concept of the invention, technical solution
The understanding entered.
Embodiment 1
A kind of production method of simple and convenient benzalkonium chloride, includes the following steps:
A, it after taking 30mol Dodecyl Dimethyl Amine (6.40kg) to mix with 30mol benzyl chloride (3.40kg), is added
The dissolution of 100L ethyl acetate；
B, mixed liquor is pumped into 300L glassed steel reaction vessels, the steam heating of agitating device and the TCU control of reaction kettle
Heating device, system after insulation reaction 8 hours, is naturally cooling to filter after crystal is precipitated completely under the conditions of 85-95oC；
With 3 cleaning crystal of ethyl acetate point during filtering, retain filter cake；
C, by it is above-mentioned filter rear dissolution of crystals heat ethyl acetate in recrystallize, taken out after crystal is precipitated completely
Filter, crystal are dried under vacuum to constant weight under the conditions of -1.5Mpa, 60 DEG C up to high-purity pharmaceutical grade benzalkonium chloride monomer 9.31Kg.
Embodiment 2
A kind of production method of simple and convenient benzalkonium chloride, includes the following steps:
A, it after taking 30mol dodecyldimethylamine base tertiary amine (7.24kg) to mix with 30mol benzyl chloride (3.40kg), is added
The dissolution of 100L ethyl acetate；
B, mixed liquor is pumped into 300L glassed steel reaction vessels, the steam heating of agitating device and the TCU control of reaction kettle
Heating device, system after insulation reaction 8-10 hours, is naturally cooling to take out after crystal is precipitated completely under the conditions of 85-95oC
Consider；With 4 cleaning crystal of ethyl acetate point during filtering, retain filter cake；
C, by it is above-mentioned filter rear dissolution of crystals heat ethyl acetate in recrystallize, taken out after crystal is precipitated completely
Filter, crystal are dried under vacuum to constant weight under the conditions of -1.5Mpa, 60 DEG C up to high-purity pharmaceutical grade benzalkonium chloride monomer 10.1Kg.
Embodiment 3
A, it after 30mol hexadecyldimethyl benzyl ammonium tertiary amine (8.08kg) is mixed with 30mol benzyl chloride (3.40kg), is added
The dissolution of 100L ethyl acetate；
B, mixed liquor is pumped into 300L glassed steel reaction vessels, the steam heating of agitating device and the TCU control of reaction kettle
Heating device, system after insulation reaction 9 hours, is naturally cooling to filter after crystal is precipitated completely under the conditions of 85-95oC；
With 5 cleaning crystal of ethyl acetate point during filtering, retain filter cake；
C, by it is above-mentioned filter rear dissolution of crystals heat ethyl acetate in recrystallize, taken out after crystal is precipitated completely
Filter, crystal are dried under vacuum to constant weight under the conditions of -1.5Mpa, 60 DEG C up to high-purity pharmaceutical grade benzalkonium chloride monomer 10.9Kg.
Comparative example 1
Domiphen is squeezed into destilling tower, is distilled 30 hours under reduced pressure atmosphere, after distillation, leads to cool brine
Freezing 5 hours, and centrifugation is stirred, later by material by filtering kettle, room temperature filtering obtains material A；Benzyl chloride is pumped into steaming again
Tower is evaporated, is distilled 4 hours in the environment of 60 DEG C, obtains material B；Material A is pumped into reaction kettle, then material B is pumped into head tank,
It is heated while stirring in the environment of 56-60 DEG C and instills material B in reaction kettle, insulation reaction 2 hours, be then turned on circulation
Cooling water is cooled to room temperature to get product.
The performance difference for the benzalkonium chloride that embodiment 1-3 and comparative example 1 are prepared is as shown in table 1.
Table 1
。
For the ordinary skill in the art, specific embodiment is only exemplarily described the present invention,
Obviously the present invention specific implementation is not subject to the restrictions described above, as long as use the inventive concept and technical scheme of the present invention into
The improvement of capable various unsubstantialities, or not improved the conception and technical scheme of the invention are directly applied to other occasions
, it is within the scope of the present invention.
Claims (7)
1. a kind of production method of benzalkonium chloride, it is characterised in that the following steps are included: A, by alkyl dimethyl tertiary amide and chlorination
Benzyl after the molar ratio mixing of 1:1 to be dissolved in ethyl acetate；B, mixed liquor is added in 300L glassed steel reaction vessels, is opened anti-
The steam-heated heating device of the agitating device and TCU control of answering kettle is analysed after natural cooling after warm reaction a period of time
Crystal out, decompression filter, and divide 2-5 cleaning crystal with ethyl acetate during suction filtration, retain filter cake；It C, will be brilliant after above-mentioned suction filtration
Body is dissolved in the ethyl acetate of heat and is recrystallized, and filters after crystal is precipitated completely, crystal is in -1.5Mpa, 60 DEG C of conditions
Under be dried under vacuum to constant weight up to purity be greater than 99% benzalkonium chloride monomer, belong to pharmaceutical grade benzalkonium chloride monomer.
2. a kind of production method of benzalkonium chloride according to claim 1, it is characterised in that: alkyl two in the step A
Methyl tertiary amine is Dodecyl Dimethyl Amine, dodecyldimethylamine base tertiary amine or hexadecyldimethyl benzyl ammonium tertiary amine.
3. a kind of production method of benzalkonium chloride according to claim 1, it is characterised in that: mixed liquor in the step B
Temperature in insulation reaction is 70-100oC, insulation reaction time are 7-10 hours.
4. a kind of production method of benzalkonium chloride as described in claim 1, which is characterized in that add described in the step B
Hot charging is set to the steam-heated collet of TCU control.
5. a kind of production method of benzalkonium chloride as described in claim 1, which is characterized in that ethyl acetate in the step B
Wash number is subject to fatty alkyl dimethyl tertiary amine and benzyl chloride content in final crystal lower than 0.05%.
6. a kind of production method of benzalkonium chloride according to claim 1, it is characterised in that: hot second in the step C
Temperature in acetoacetic ester is 40~70oC。
7. a kind of production method of benzalkonium chloride according to claim 1, it is characterised in that: recrystallized in the step C
Middle ethyl acetate additional amount, which is subject to, is completely dissolved crystal.
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| CN1287021A (en) * | 2000-07-05 | 2001-03-14 | 北京清华紫光英力化工技术有限责任公司 | Compound phase-transferring quaternary ammonium salt catalyst in beta-hydroxyl structure and its preparation |
| JP2002030044A (en) * | 2000-07-12 | 2002-01-29 | Sakai Chem Ind Co Ltd | Method for producing tetraalkylammonium halide |
| CN101050182A (en) * | 2006-04-06 | 2007-10-10 | 浙江华特实业集团华特化工有限公司 | Method for preparing quaternary ammonium salt |
| CN103351301A (en) * | 2013-07-01 | 2013-10-16 | 安徽奔马先端科技有限公司 | Synthetic method for high-purity quaternary ammonium salt |
| CN104163763A (en) * | 2014-07-14 | 2014-11-26 | 安徽奔马先端科技有限公司 | New synthesis method of high purity quaternary ammonium salt |
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- 2017-03-24 CN CN201710182475.0A patent/CN106916068B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1287021A (en) * | 2000-07-05 | 2001-03-14 | 北京清华紫光英力化工技术有限责任公司 | Compound phase-transferring quaternary ammonium salt catalyst in beta-hydroxyl structure and its preparation |
| JP2002030044A (en) * | 2000-07-12 | 2002-01-29 | Sakai Chem Ind Co Ltd | Method for producing tetraalkylammonium halide |
| CN101050182A (en) * | 2006-04-06 | 2007-10-10 | 浙江华特实业集团华特化工有限公司 | Method for preparing quaternary ammonium salt |
| CN103351301A (en) * | 2013-07-01 | 2013-10-16 | 安徽奔马先端科技有限公司 | Synthetic method for high-purity quaternary ammonium salt |
| CN104163763A (en) * | 2014-07-14 | 2014-11-26 | 安徽奔马先端科技有限公司 | New synthesis method of high purity quaternary ammonium salt |
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Effective date of registration: 20180706 Address after: 515000 block B, Chengde Square, Shantou Free Trade Zone, Shantou, Guangdong. Applicant after: Guangdong loest Pharmaceutical Co. Ltd. Address before: 515000 Shantou City, Guangdong province free trade zone Applicant before: Wu Lian |
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Address after: 515000 one of the second floor of building 0001, block e08-4, Shantou Free Trade Zone, Shantou City, Guangdong Province Patentee after: Guangdong loest Pharmaceutical Co.,Ltd. Address before: 515000 block B, Chengde Square, Shantou Free Trade Zone, Shantou, Guangdong. Patentee before: Guangdong loest Pharmaceutical Co.,Ltd. |
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