CN101565375A - Adamantyl quaternary ammonium salt and preparation method thereof - Google Patents
Adamantyl quaternary ammonium salt and preparation method thereof Download PDFInfo
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Abstract
The invention discloses an adamantyl quaternary ammonium salt and a preparation method thereof. The structural formula of the adamantyl quaternary ammonium salt is shown as right formula, wherein R represents phenmethyl or alkyl containing 1 to 18 carbon atoms; and X represents Cl, Br or I. The preparation method of the adamantyl quaternary ammonium salt adopts amantadine as a material and adopts two-step reaction as follows: adopting amantadine to synthesize adamantyl dimethyl-tert-amine and then synthesizing the adamantyl quaternary ammonium salt through quaterisation of the adamantyl dimethyl-tert-amine. The invention has easy operation, mild reaction process, high yield and purity and low product eco-toxicity. The cation surface active agent of the adamantyl quaternary ammonium salt can be potentially applied to high and new technology fields of micro-electronics, biomedicine, pharmacy, nanometer material and the like.
Description
Technical field
The present invention relates to a kind of adamantyl quaternary ammonium salt and preparation method thereof.
Background technology
Quarternary ammonium salt compound is the important fine chemicals of a class, can be used as washing composition, sterilant, static inhibitor, softening agent, the main component of template, at household chemicals, automobile, weaving, electronics, oil production, biomedical, pharmacy, there is extensive and important purposes in fields such as novel material preparation, substituting group on the quarternary ammonium salt compound N atom of having reported so far mostly is straight chained alkyl or aromatic base, the type and the range of application of quaternary ammonium salt are restricted, for example, many quaternary ammonium alkyl salt compound only just has fungicidal activity preferably during as sterilizing agent under higher concentration, and it is bad to the part microorganism effect, particularly to some virus, antimicrobial spectrum is little, invalid to clear water virus, sterilization application is limited in scope.For the kind and the application of expanding quarternary ammonium salt compound, in recent years, the research and development of novel quaternary ammonium salt are constantly carried out; double type quaternary cationics (CN101385957 wherein; CN101337169, CN101279218, US 6; 794; 345, US 6,777; 384) cause general interest with performances such as its excellent surface activity, antistatic, sterilizations, but the preparation of gemini quaternary ammonium salt cats product and purification techniques are comparatively complicated, large-scale production acquires a certain degree of difficulty.
Summary of the invention
The object of the present invention is to provide a kind of adamantyl quaternary ammonium salt and preparation method thereof.
A kind of quarternary ammonium salt compound that contains the diamantane group provided by the invention and preparation method thereof, utilize diamantane height symmetry, high inflexible cage shape molecular structure and unique physicochemical property thereof, design and synthesize out an adamantane-like based quaternary ammonium salt cationic surfactant, this adamantyl quaternary ammonium salt cats product has potential use at high-technology fields such as microelectronics, biomedicine, pharmacy, nano materials.
Technical scheme of the present invention is as follows:
Adamantyl quaternary ammonium salt involved in the present invention, its structural formula is as follows:
In the formula: R represents benzyl or contains the alkyl of 1～18 carbon atom; X represents Cl, Br or I.
The concrete preparation method of adamantyl quaternary ammonium salt involved in the present invention is as follows:
(1) the adamantyl dimethyl tertiary amine is synthetic: amantadine is dissolved in the organic solvent, under 10 ℃～65 ℃ temperature condition, slowly add formic acid and formaldehyde respectively, then under 70 ℃～120 ℃, reacted 5～30 hours, transfer to alkalescence with sodium hydroxide solution again, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine.
(2) the adamantyl dimethyl tertiary amine is quaternized: synthetic adamantyl dimethyl tertiary amine is added fully dissolving in the organic solvent, slowly add quaternizing agent again, reacted 3～45 hours down in 60 ℃～120 ℃ temperature condition, underpressure distillation removes and desolvates, with excessive ether washing, vacuum-drying obtains corresponding adamantyl quaternary ammonium salt then.
The mass ratio of described amantadine of step (1) and organic solvent is 1: 1～1: 10, and the mol ratio of described amantadine and formic acid is 1: 2～1: 10, and the mol ratio of described amantadine and formaldehyde is 1: 2～1: 10.
The mass ratio of described adamantyl dimethyl tertiary amine of step (2) and organic solvent is 1: 0.5～1: 10, and the mol ratio of described adamantyl dimethyl tertiary amine and quaternizing agent is 1: 1～1: 5.
Aforesaid organic solvent is low-carbon alcohol or its mixture that contains 1～5 carbon atom.
The general structure of the quaternizing agent of described step (2) is RX;
Wherein: R is benzyl or the alkyl that contains 1～18 carbon atom; X is Cl, Br or I.
The invention has the beneficial effects as follows:
The present invention is a raw material with the amantadine, and is promptly first by amantadine synthesizing adamantane base dimethyl tertiary amine by two-step reaction, and then passes through the quaterisation synthesizing adamantane based quaternary ammonium salt of adamantyl dimethyl tertiary amine.Operation is simple for present method, the reaction conditions gentleness, products therefrom yield height, purity height, product eco-toxicity are low, and this adamantyl quaternary ammonium salt cats product has potential use at high-technology fields such as microelectronics, biomedicine, pharmacy, nano materials.
Embodiment
Below in conjunction with embodiment the present invention is made further specifying, but the present invention is not limited to these embodiment.
Embodiment 1
In the 500mL there-necked flask that reflux condensing tube is housed, add the 15.1g amantadine, 189mL methyl alcohol, heating while stirring prior to 10 ℃, adds 46g formic acid in the 40min, under 50 ℃, add 46g formaldehyde in the 4.5h; Be warming up to 70 ℃ then, reaction 30h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 91%.
15g adamantyl dimethyl tertiary amine and 185mL methyl alcohol are dropped in the 500mL there-necked flask, add the 53.1g benzyl chloride again, being warming up to 60 ℃ continues to stir 20 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethylbenzyl based quaternary ammonium salt, yield 97%.
Embodiment 2
In the 100mL there-necked flask that reflux condensing tube is housed, add the 15.1g amantadine, the 19mL Pentyl alcohol, heating while stirring prior to 20 ℃, adds 9.2g formic acid in the 40min, under 65 ℃, add 6g formaldehyde in the 4.5h; Be warming up to 120 ℃ then, reaction 5h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 88%.
15g adamantyl dimethyl tertiary amine and 9.5mL Pentyl alcohol are dropped in the 100mL there-necked flask, add the 10.7g benzyl chloride again, being warming up to 120 ℃ then continues to stir 3 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethylbenzyl based quaternary ammonium salt, yield 94%.
Embodiment 3
In the 500mL there-necked flask that reflux condensing tube is housed, add the 30g amantadine, the 200mL Virahol, heating while stirring prior to 35 ℃, adds 46g formic acid in the 40min, under 50 ℃, add 24g formaldehyde in the 4.5h; Be warming up to 80 ℃ then, reaction 21h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 92%.
30g adamantyl dimethyl tertiary amine and 190mL Virahol are dropped in the 500mL there-necked flask, add the 25.3g benzyl chloride again, being warming up to 80 ℃ then continues to stir 9 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethylbenzyl based quaternary ammonium salt, yield 96%.
Embodiment 4
In the 500mL there-necked flask that reflux condensing tube is housed, add the 30g amantadine, the 200mL Virahol, heating while stirring prior to 35 ℃, adds 36.8g formic acid in the 40min, under 50 ℃, add 30g formaldehyde in the 4.5h; Be warming up to 80 ℃ then, reaction 21h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 91%.
30g adamantyl dimethyl tertiary amine and 190mL ethanol are dropped in the 500mL there-necked flask, add the 31.53g bromotoluene again, being warming up to 77 ℃ then continues to stir 8 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethylbenzyl based quaternary ammonium salt, yield 97%.
Embodiment 5
In the 500mL there-necked flask that reflux condensing tube is housed, add the 24g amantadine, 160mL ethanol, heating while stirring prior to 35 ℃, adds 44g formic acid in the 40min, under 50 ℃, add 24g formaldehyde in the 4.5h; Be warming up to 78 ℃ then, reaction 18h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 92%.
20g adamantyl dimethyl tertiary amine and 100mL ethanol are dropped in the 250mL there-necked flask, add the 18.46g methyl iodide again, being warming up to 75 ℃ then continues to stir 10 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl trimethyl quaternary ammonium salt, yield 97%.
Embodiment 6
In the 500mL there-necked flask that reflux condensing tube is housed, add the 30g amantadine, 120mL ethanol, heating while stirring prior to 35 ℃, adds 36.8g formic acid in the 40min, under 50 ℃, add 18g formaldehyde in the 4.5h; Be warming up to 78 ℃ then, reaction 23h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 89%.
30g adamantyl dimethyl tertiary amine and 200mL Virahol are dropped in the 500mL there-necked flask, add the 29.86g bromination of n-butane again, being warming up to 80 ℃ then continues to stir 9 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl n butyl quaternary ammonium salt, yield 95%.
Embodiment 7
In the 250mL there-necked flask that reflux condensing tube is housed, add the 24g amantadine, the 90mL Virahol, heating while stirring prior to 35 ℃, adds 44g formic acid in the 40min, under 50 ℃, add 19.2g formaldehyde in the 4.5h; Be warming up to 80 ℃ then, reaction 21h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 90%.
20g adamantyl dimethyl tertiary amine and 100mL Virahol are dropped in the 250mL there-necked flask, add the 24.66g iodo-n-butane again, being warming up to 80 ℃ then continues to stir 10 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl n butyl quaternary ammonium salt, yield 96%.
Embodiment 8
In the 250mL there-necked flask that reflux condensing tube is housed, add the 20g amantadine, 100mL Virahol and alcohol mixeding liquid (volume ratio 1: 1), heating while stirring prior to 35 ℃, adds 29.9g formic acid in the 40min, under 50 ℃, adding 15.6g formaldehyde in the 4.5h; Be warming up to 80 ℃ then, reaction 20h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 91%.
In 20g adamantyl dimethyl tertiary amine and 100mL Virahol and alcohol mixeding liquid (volume ratio 1: 1) input 250mL there-necked flask, add the 36.35g bromododecane again, being warming up to 80 ℃ then continues to stir 12 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl dodecyl quaternary ammonium salt, yield 95%.
Embodiment 9
In the 500mL there-necked flask that reflux condensing tube is housed, add the 15.1g amantadine, the 152mL propyl carbinol, heating while stirring prior to 55 ℃, adds 32.2g formic acid in the 40min, under 60 ℃, add 12g formaldehyde in the 4.5h; Be warming up to 110 ℃ then, reaction 15h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 89%.
15g adamantyl dimethyl tertiary amine and 96mL methyl alcohol are dropped in the 250mL there-necked flask, add the 38.34g bromooctane again, being warming up to 70 ℃ then continues to stir 38 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl-octa alkyl quaternary ammonium salts, yield 90%.
Embodiment 10
In the 500mL there-necked flask that reflux condensing tube is housed, add the 15.1g amantadine, the 196mL primary isoamyl alcohol, heating while stirring prior to 65 ℃, adds 36.8g formic acid in the 40min, under 65 ℃, add 18g formaldehyde in the 4.5h; Be warming up to 120 ℃ then, reaction 10h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 91%.
16g adamantyl dimethyl tertiary amine and 161mL propyl carbinol are dropped in the 500mL there-necked flask, add the 129.36g bromohexadecane again, being warming up to 120 ℃ then continues to stir 30 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl hexadecyl quaternary ammonium salt, yield 91%.
Embodiment 11
In the 500mL there-necked flask that reflux condensing tube is housed, add the 22.65g amantadine, 173mL methyl alcohol, heating while stirring prior to 50 ℃, adds 44.85g formic acid in the 40min, under 55 ℃, add 22.5g formaldehyde in the 4.5h; Be warming up to 70 ℃ then, reaction 22h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 92%.
24g adamantyl dimethyl tertiary amine and 300mL ethanol are dropped in the 1000mL there-necked flask, add the 132.36g bromo-octadecane again, being warming up to 80 ℃ then continues to stir 45 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl stearyl quaternary ammonium salt, yield 93%.
Embodiment 12
In the 500mL there-necked flask that reflux condensing tube is housed, add the 19.63g amantadine, the 175mL n-propyl alcohol, heating while stirring prior to 30 ℃, adds 32.8g formic acid in the 40min, under 40 ℃, add 19.5g formaldehyde in the 4.5h; Be warming up to 95 ℃ then, reaction 18h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 90%.
In 20g adamantyl dimethyl tertiary amine and 230mL methyl alcohol and Virahol mixed solution (volume ratio 1: 2) input 1000mL there-necked flask, add the 81.31g chlorinated dodecane again, being warming up to 80 ℃ then continues to stir 40 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl dodecyl quaternary ammonium salt, yield 92%.
Embodiment 13
In the 500mL there-necked flask that reflux condensing tube is housed, add the 27.18g amantadine, the 240mL dehydrated alcohol, heating while stirring prior to 25 ℃, adds 33.12g formic acid in the 40min, under 38 ℃, add 24.3g formaldehyde in the 4.5h; Be warming up to 80 ℃ then, reaction 20h.Transfer to alkalescence with sodium hydroxide solution again after reaction finishes, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine, yield 90%.
In 25g adamantyl dimethyl tertiary amine and 220mL primary isoamyl alcohol and alcohol mixeding liquid (volume ratio 1: 4) input 1000mL there-necked flask, add the 215.82g chloro-hexadecane again, being warming up to 83 ℃ then continues to stir 45 hours, underpressure distillation removes and desolvates then, with excessive ether washing, vacuum-drying obtains corresponding adamantyl dimethyl dodecyl quaternary ammonium salt, yield 90%.
Claims (6)
1, a kind of adamantyl quaternary ammonium salt is characterized in that the structural formula of adamantyl quaternary ammonium salt is as follows:
In the formula: R represents benzyl or contains the alkyl of 1～18 carbon atom; X represents Cl, Br or I.
2, the preparation method of the described adamantyl quaternary ammonium salt of a kind of claim 1, step is as follows:
(1) the adamantyl dimethyl tertiary amine is synthetic: amantadine is dissolved in the organic solvent, under 10 ℃～65 ℃ temperature condition, slowly add formic acid and formaldehyde respectively, then under 70 ℃～120 ℃, reacted 5～30 hours, transfer to alkalescence with sodium hydroxide solution again, isolate upper solution, and be washed to water layer and be neutral, organic layer vacuum-drying obtains the adamantyl dimethyl tertiary amine;
(2) the adamantyl dimethyl tertiary amine is quaternized: synthetic adamantyl dimethyl tertiary amine is added fully dissolving in the organic solvent, slowly add quaternizing agent again, reacted 3～45 hours down in 60 ℃～120 ℃ temperature condition, underpressure distillation removes and desolvates, with excessive ether washing, vacuum-drying obtains corresponding adamantyl quaternary ammonium salt then.
3, the preparation method of adamantyl quaternary ammonium salt according to claim 2, the mass ratio that it is characterized in that described amantadine of step (1) and organic solvent is 1: 1～1: 10, the mol ratio of described amantadine and formic acid is 1: 2～1: 10, and the mol ratio of described amantadine and formaldehyde is 1: 2～1: 10.
4, the preparation method of adamantyl quaternary ammonium salt according to claim 2, the mass ratio that it is characterized in that described adamantyl dimethyl tertiary amine of step (2) and organic solvent is 1: 0.5～1: 10, and the mol ratio of described adamantyl dimethyl tertiary amine and quaternizing agent is 1: 1～1: 5.
5, the preparation method of adamantyl quaternary ammonium salt according to claim 2 is characterized in that described organic solvent is low-carbon alcohol or its mixture that contains 1～5 carbon atom.
6, the preparation method of adamantyl quaternary ammonium salt according to claim 2, the general structure that it is characterized in that described quaternizing agent is RX;
Wherein: R is benzyl or the alkyl that contains 1～18 carbon atom; X is Cl, Br or I.
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Cited By (11)
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| CN101735078A (en) * | 2009-12-22 | 2010-06-16 | 广东工业大学 | Adamantine-based ethoxyl quaternary ammonium salt and method for preparing same |
| CN101935286A (en) * | 2009-06-26 | 2011-01-05 | 出光兴产株式会社 | Method for producing quaternary ammonium salt having adamantyl group |
| CN102115448A (en) * | 2010-12-06 | 2011-07-06 | 上海博康精细化工有限公司 | Admantyl quaternary ammonium base and preparation method thereof |
| CN102174116A (en) * | 2011-03-24 | 2011-09-07 | 华南理工大学 | 1-amantadine hydrochloride carboxylic acid cellulose ester and method for preparing same |
| CN102513023A (en) * | 2011-10-31 | 2012-06-27 | 广东工业大学 | Trimeric surfactant and its synthetic method |
| CN102978915A (en) * | 2012-10-31 | 2013-03-20 | 浙江安诺其助剂有限公司 | Alkali decrement promoter and preparation method thereof |
| CN103420857A (en) * | 2013-09-03 | 2013-12-04 | 天津民祥药业有限公司 | Method for preparing quaternary ammonium salt with adamantyl |
| CN106365221A (en) * | 2016-11-09 | 2017-02-01 | 烟台史密得机电设备制造有限公司 | Adamantine mono-quaternary ammonium salt cationic three compound combination flooding produced water oil remover |
| CN109836349A (en) * | 2017-11-27 | 2019-06-04 | 贺州学院 | A kind of Gemini surface active and its synthetic method containing adamantane |
| US10538482B2 (en) | 2015-07-28 | 2020-01-21 | Institut National De La Santé Et De La Recherche Médicale (Inserm) | Adamantane and memantine derivatives as peripheral NMDA receptor antagonists |
| CN110746310A (en) * | 2019-10-12 | 2020-02-04 | 青岛大学 | Preparation method of novel low-permeability reservoir water lock relieving agent |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101935286A (en) * | 2009-06-26 | 2011-01-05 | 出光兴产株式会社 | Method for producing quaternary ammonium salt having adamantyl group |
| CN101735078A (en) * | 2009-12-22 | 2010-06-16 | 广东工业大学 | Adamantine-based ethoxyl quaternary ammonium salt and method for preparing same |
| CN102115448A (en) * | 2010-12-06 | 2011-07-06 | 上海博康精细化工有限公司 | Admantyl quaternary ammonium base and preparation method thereof |
| CN102115448B (en) * | 2010-12-06 | 2013-10-30 | 上海博康精细化工有限公司 | Admantyl quaternary ammonium base and preparation method thereof |
| CN102174116A (en) * | 2011-03-24 | 2011-09-07 | 华南理工大学 | 1-amantadine hydrochloride carboxylic acid cellulose ester and method for preparing same |
| CN102174116B (en) * | 2011-03-24 | 2013-03-20 | 华南理工大学 | 1-amantadine hydrochloride carboxylic acid cellulose ester and method for preparing same |
| CN102513023B (en) * | 2011-10-31 | 2014-04-02 | 广东工业大学 | Trimeric surfactant and synthetic method thereof |
| CN102513023A (en) * | 2011-10-31 | 2012-06-27 | 广东工业大学 | Trimeric surfactant and its synthetic method |
| CN102978915A (en) * | 2012-10-31 | 2013-03-20 | 浙江安诺其助剂有限公司 | Alkali decrement promoter and preparation method thereof |
| CN103420857A (en) * | 2013-09-03 | 2013-12-04 | 天津民祥药业有限公司 | Method for preparing quaternary ammonium salt with adamantyl |
| US10538482B2 (en) | 2015-07-28 | 2020-01-21 | Institut National De La Santé Et De La Recherche Médicale (Inserm) | Adamantane and memantine derivatives as peripheral NMDA receptor antagonists |
| CN106365221A (en) * | 2016-11-09 | 2017-02-01 | 烟台史密得机电设备制造有限公司 | Adamantine mono-quaternary ammonium salt cationic three compound combination flooding produced water oil remover |
| CN109836349A (en) * | 2017-11-27 | 2019-06-04 | 贺州学院 | A kind of Gemini surface active and its synthetic method containing adamantane |
| CN109836349B (en) * | 2017-11-27 | 2022-02-15 | 贺州学院 | Adamantane-containing Gemini surfactant and synthesis method thereof |
| CN110746310A (en) * | 2019-10-12 | 2020-02-04 | 青岛大学 | Preparation method of novel low-permeability reservoir water lock relieving agent |
| CN110746310B (en) * | 2019-10-12 | 2023-05-26 | 青岛大学 | Preparation method of low-permeability oil reservoir water lock release agent |
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Application publication date: 20091028 |