CN101050185A - Ion liquid of quaternaries of naphthenic acid - Google Patents
Ion liquid of quaternaries of naphthenic acid Download PDFInfo
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- CN101050185A CN101050185A CN 200710099180 CN200710099180A CN101050185A CN 101050185 A CN101050185 A CN 101050185A CN 200710099180 CN200710099180 CN 200710099180 CN 200710099180 A CN200710099180 A CN 200710099180A CN 101050185 A CN101050185 A CN 101050185A
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Abstract
This invention discloses a method for preparing naphthenic acid quaternary ammonium salt ionic liquid. The method adopts one of naphthenic acid compounds as the anion donor, one of tertiary amine or quaternary ammonium alkali compounds as the cation donor, and one or more of water, methanol, ethanol, isopropanol, acetone and cyclohexane as the reaction medium. At normal temperature and pressure, the anion donor and the cation donor at a mol. Ratio of 1:1 are subjected to one-step neutralization reaction to obtain naphthenic acid quaternary ammonium salt ionic liquid. The method has such advantages as easy operation, high efficiency and no byproducts. The obtained naphthenic acid quaternary ammonium salt ionic liquid has such advantages as high electric conductivity, high heat resistance and wide electrochemical stable range.
Description
Invention field: the present invention relates to the synthetic of a kind of ion liquid of quaternaries of naphthenic acid of chemical field.
Background of invention:
Ionic liquid is by organic cation and the compound that is in a liquid state under room temperature and adjacent temperature inorganic or that organic anion is formed.
Compare with ionogen with traditional organic solvent, ionic liquid has a series of outstanding advantages: almost there is not vapour pressure under (1) room temperature, and non-volatile, can be used for the reaction under the high vacuum condition, can reduce the problem of environmental pollution that produces because of volatilization simultaneously; (2) have good chemistry, thermodynamic stability and suitable viscosity, can be used as the stationary phase of liquid chromatography; (3) have the height designability, can be by changing yin, yang ionic size, the alkyl chain length minor saves its polarity, potential of hydrogen and its to the solvability of inorganics, water, organism and polymkeric substance etc.; (4) do not dissolve each other with some organic solvents, a non-water, two-phase system that polarity is adjustable can be provided, can reduce traditional molecular solvent effectively phenomenons such as the solvation of solute, solvolysises; (5) wider range that exists as liquid form helps thermodynamic control; (6) have higher ion migration and velocity of diffusion, thereby have good electrical conductivity, the electrochemical window of broad can be used as the electrolytic solution of many material electrochemical researchs.
Because these special nature of ionic liquid, it can replace traditional organic solvent and ionogen, aspect organic synthesis, electrochemistry, catalytic chemistry, Materials science and the mineral solution chemistry wide application prospect being arranged, also be expected to open up new road for green non-pollution industry.Therefore, we need synthesize increasing novel, have the specific function ionic liquid material, to adapt to ion liquid research demand.
Ion liquid synthetic method can be divided into one-step synthesis and two step synthesis methods usually.Wherein one-step synthesis mainly is by acid-base neutralisation reaction or quaternary ammonium reaction one-step synthesis ionic liquid, and the operation economical and convenient does not have by product, easy purification of products.Two step synthesis methods mainly are at first to prepare by quaternary ammonium reaction to contain the cationic halogen of target, react with it with big negatively charged ion displacement halogen ion or adding Lewis acid then to obtain object ion.The advantage of two step synthesis methods is that universality is good, but maximum problem is that anion exchange reaction will produce inorganic salt by-product in synthetic, and is unfriendly to environment in the preparation process.There is simultaneously a spot of inorganic salt impurity to be difficult to measure inevitably and removes, the purifying of ionic liquid product has been caused certain difficulty.Therefore comparatively speaking, one-step synthesis is more paid close attention to.
Summary of the invention
The objective of the invention is to synthetic a kind of is the negatively charged ion donor with the naphthenic series compound, is the novel ion liquid of positively charged ion donor with tertiary amines and quaternary amine alkali compounds.
Concrete grammar of the present invention is: choose the naphthenic series compound: a kind of for the negatively charged ion donor in Cyclopentane carboxylic acid, hexahydrobenzoic acid, hexanaphthene diacetic acid, 1-methyl isophthalic acid-hexahydrobenzoic acid, 4-amyl group hexahydrobenzoic acid, dicyclohexyl acetate, cyclohexenecarboxylic acid, suberyl formic acid, cyclopentyl formic acid, phenylformic acid, Whitfield's ointment, acetylsalicylic acid, sylvic acid, Septochol, 5 β-ursodeoxycholic acid, the 18-β-glycyrrhetinic acid; Choose tertiary amine compounds: N, the N-diethylethanolamine, N, the N-dimethylethanolamine, N, the N-dimethyl propanol amine, N, the N-dimethylisopro panolamine, N, the N-diethyl-p-tlouidine, N, the N-Diethyl Aniline, N, the N-xylidene(s), N, dinethylformamide, N, the N-dimethylcyclohexylamine, N, the N-diisopropylethylamine, tri-n-butylamine, Tri-n-Propylamine, three allyls (base) amine, N, N, N ', a kind of or quaternary amine alkali compounds in N '-Tetramethyl Ethylene Diamine: Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, TPAOH, TBAH, benzyltrimethylammonium hydroxide, benzyl triethyl ammonium ammonium hydroxide, the dodecyl trimethylammonium hydroxide, the trioctylphosphine ammonium hydroxide, choline, vagusstoff, BuCh, benzoylcholine, a kind of in the phosphatidylcholine is the positively charged ion donor, with water, methyl alcohol, ethanol, Virahol, acetone, the mixture of one or several in the hexanaphthene is as reaction medium, according to etc. mol ratio at normal temperature, normal pressure generates ion liquid of quaternaries of naphthenic acid by a step neutralization reaction down.This route reaction efficient height does not have by product.The ionic liquid that generates has higher specific conductivity, higher thermostability and the electrochemical stability interval of broad, and value has a wide range of applications.
Embodiment:
The present invention illustrates with following example, but the present invention is not limited to following embodiment, under the scope of described aim, changes and implements to be included in the technical scope of the present invention before and after not breaking away from.
Embodiment 1
Precision takes by weighing 0.02mol hexahydrobenzoic acid meter 2.563g, adds in the round-bottomed flask, again to wherein adding 10ml ethanol, and fully stir hexahydrobenzoic acid dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the choline solution meter 5.246g that wherein slowly drips 45wt%.React 18h at ambient temperature.Reactant is rotary evaporation in vacuo 90min under 50 ℃ condition, and most of ethanol is removed, and the liquid with gained places 50 ℃ of dry 48h of vacuum drying oven then, and is final that proterties is product 4.367g colourless, thick liquid.
Embodiment 2
Precision takes by weighing Whitfield's ointment 2.763g, adds in the round-bottomed flask, again to wherein adding 10ml ethanol, and fully stir Whitfield's ointment dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the choline solution 5.306g that wherein slowly drips 45wt%.Under 25 ℃ temperature condition, react 20h.Reactant is rotary evaporation in vacuo 60min under 50 ℃ condition, and most of ethanol is removed, and the liquid with gained places 50 ℃ of dry 48h of vacuum drying oven then, and is final that proterties is product 4.526g faint yellow, thick liquid.
Embodiment 3
Precision takes by weighing hexahydrobenzoic acid 2.585g, adds in the round-bottomed flask, again to wherein adding 5ml methyl alcohol, and fully stir hexahydrobenzoic acid dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the methanol solution 8.401g of the benzyltrimethylammonium hydroxide that wherein slowly drips 40wt%.Under 20 ℃ temperature condition, react 22h.Reactant is rotary evaporation in vacuo 90min under 40 ℃ condition, and most of methyl alcohol is removed, and the product with gained places 50 ℃ of dry 48h of vacuum drying oven then, the final product 5.210g that gets.
Embodiment 4
Precision takes by weighing Whitfield's ointment 1.381g, adds in the round-bottomed flask, again to wherein adding 10ml ethanol, and fully stir Whitfield's ointment dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the methanol solution 4.189g of the benzyltrimethylammonium hydroxide that wherein slowly drips 40wt%.Under 15 ℃ temperature condition, react 24h.Reactant is rotary evaporation in vacuo 60min under 40 ℃ condition, methyl alcohol in the methanol solution of most of reaction medium ethanol and benzyltrimethylammonium hydroxide is removed, product with gained places 50 ℃ of dry 48h of vacuum drying oven then, the final product 2.592g that gets.
Claims (6)
1. ion liquid of quaternaries of naphthenic acid, it is characterized in that such ionic liquid is is the negatively charged ion donor with the naphthenic series compound, with tertiary amines and quaternary amine alkali compounds is the positively charged ion donor, in certain medium according to etc. mol ratio, reaction certain hour synthetic under certain temperature, pressure condition, such ion liquid structural formula is as follows:
Wherein, negatively charged ion is that main body is the monocarboxylic acid of five-ring or six-ring, n=1～5, and R is the alkyl substituent;
If positively charged ion donor tertiary amine compounds, R
1Be H, R
2, R
3, R
4For identical or different carbonatomss is 1～4 alkyl, the substituent of hydroxyl; If positively charged ion donor quaternary amine alkali compounds, R
1, R
2, R
3, R
4It for identical or different carbonatomss the substituent of 1～12 alkyl, hydroxyl or aryl.
2. method according to claim 1, wherein such ion liquid negatively charged ion donor is the naphthenic series compound, mainly comprises Cyclopentane carboxylic acid, hexahydrobenzoic acid, 1-methyl isophthalic acid-hexahydrobenzoic acid, 4-amyl group hexahydrobenzoic acid, dicyclohexyl acetate, cyclohexenecarboxylic acid, cyclopentyl formic acid, phenylformic acid, acetylsalicylic acid, sylvic acid, Septochol, 5 β-ursodeoxycholic acid, 18-β-glycyrrhetinic acid.
3. method according to claim 1, wherein such ion liquid positively charged ion donor is tertiary amines and quaternary amine alkali compounds, wherein tertiary amine compounds mainly comprises N, N-diethylethanolamine, N, N-dimethylethanolamine, N, N-dimethyl propanol amine, N, N-dimethylisopro panolamine, N, N-diethyl-p-tlouidine, N, N-Diethyl Aniline, N, N-xylidene(s), N, dinethylformamide, N, N-dimethylcyclohexylamine, N, N-diisopropylethylamine, tri-n-butylamine, Tri-n-Propylamine; The quaternary amine alkali compounds mainly comprises Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, TPAOH, TBAH, benzyltrimethylammonium hydroxide, benzyl triethyl ammonium ammonium hydroxide, dodecyl trimethylammonium hydroxide, trioctylphosphine ammonium hydroxide, choline, vagusstoff, BuCh, benzoylcholine, phosphatidylcholine.
4. according to the described method of claim 1～3, wherein such ion liquid synthetic mainly be to choose a kind of in the above-mentioned yin, yang ion donor compound separately, according to etc. mol ratio finish by a step neutralization reaction, the reaction efficiency height does not have by product.
5. method according to claim 1, wherein Fan Ying medium is mainly one or more the mixture in water, methyl alcohol, ethanol, Virahol, acetone, the hexanaphthene.
6. method according to claim 1, wherein such ionic liquid is under normal pressure, 10～50 ℃ temperature condition is reaction 2～24h synthetic down.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105238926A (en) * | 2015-11-13 | 2016-01-13 | 厦门稀土材料研究所 | Extraction separation method for yttrium |
| CN106265697A (en) * | 2016-08-16 | 2017-01-04 | 武汉软件工程职业学院 | Salicylic acid mixture and preparation method thereof, salicylic acid ionic liquid solution and the purposes of ionic liquid |
| US10428405B2 (en) | 2015-05-25 | 2019-10-01 | Xiamen Institute Of Rare Earth Materials | Extractant and method for extracting and separating yttrium |
| CN111606814A (en) * | 2020-04-28 | 2020-09-01 | 廊坊师范学院 | Ionic liquid containing citrazinic acid anions and application thereof in iodine absorption |
| CN112593078A (en) * | 2020-12-03 | 2021-04-02 | 江西理工大学 | Synthetic method of organic quaternary ammonium salt |
-
2007
- 2007-05-16 CN CN 200710099180 patent/CN101050185A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10428405B2 (en) | 2015-05-25 | 2019-10-01 | Xiamen Institute Of Rare Earth Materials | Extractant and method for extracting and separating yttrium |
| CN105238926A (en) * | 2015-11-13 | 2016-01-13 | 厦门稀土材料研究所 | Extraction separation method for yttrium |
| CN105238926B (en) * | 2015-11-13 | 2017-07-21 | 厦门稀土材料研究所 | A kind of extraction separating method of yttrium |
| CN106265697A (en) * | 2016-08-16 | 2017-01-04 | 武汉软件工程职业学院 | Salicylic acid mixture and preparation method thereof, salicylic acid ionic liquid solution and the purposes of ionic liquid |
| CN111606814A (en) * | 2020-04-28 | 2020-09-01 | 廊坊师范学院 | Ionic liquid containing citrazinic acid anions and application thereof in iodine absorption |
| CN111606814B (en) * | 2020-04-28 | 2023-03-17 | 廊坊师范学院 | Ionic liquid containing citrazinic acid anions and application thereof in iodine absorption |
| CN112593078A (en) * | 2020-12-03 | 2021-04-02 | 江西理工大学 | Synthetic method of organic quaternary ammonium salt |
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