CN112442405A - Ionic liquid composition as hydraulic hydrogenation working medium - Google Patents
Ionic liquid composition as hydraulic hydrogenation working medium Download PDFInfo
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- CN112442405A CN112442405A CN202011469645.1A CN202011469645A CN112442405A CN 112442405 A CN112442405 A CN 112442405A CN 202011469645 A CN202011469645 A CN 202011469645A CN 112442405 A CN112442405 A CN 112442405A
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- Prior art keywords
- ionic liquid
- liquid composition
- sulfate anion
- ethyl
- hydraulic
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/70—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
- C10M2215/2245—Imidazoles used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/042—Sulfate esters
Abstract
The invention discloses an ionic liquid composition as a hydraulic hydrogenation working medium, which comprises the following components in mass: 100 parts of ionic liquid; 0-5 parts of an additive; wherein the general formula of the ionic liquid is as follows:
wherein: r1And R2The alkyl groups are the same or different and are respectively selected from saturated alkyl groups of C1-4; [ R ]2‑SO4]‑Is a methyl sulfate anion, an ethyl sulfate anion, a propyl sulfate anion or a butyl sulfate anion. Experiments prove that: the ionic liquid has excellent thermal stability and extremely low volatility, can prevent hydrogen from being dissolved in the composition, achieves remarkable effect, solves the problems in the field,can lead the field to achieve breakthrough development.
Description
Technical Field
The invention relates to the field of ionic liquid materials, in particular to an ionic liquid composition serving as a hydraulic hydrogenation working medium.
Background
In the prior art, ionic liquid (or called ionic liquid) refers to liquid composed of ions, such as KCI and KOH at high temperature are in liquid state, and in this case, they are ionic liquid. Substances composed of ions which are liquid at or around room temperature, referred to as room-temperature ionic liquids, room-temperature molten salts, organic ionic liquids, and the like, are not uniformly named, but are intended to be simply referred to as ionic liquids. In the ionic compound, the acting force between the anions and cations is coulomb force, the magnitude of which is related to the charge quantity and radius of the anions and cations, and the larger the ionic radius is, the smaller the acting force between the anions and the cations is, and the lower the melting point of the ionic compound is. Certain ionic compounds have bulky anions and cations and loose structures, resulting in low forces between them, such that the melting point is close to room temperature.
Ionic liquids have a number of distinct advantages when compared to traditional organic solvents and electrolytes: (1) the liquid state range is wide, the temperature is from lower than or close to room temperature to more than 300 ℃, and the thermal stability and the chemical stability are high; (2) the electrolyte has the advantages that the vapor pressure is very small, the electrolyte is non-volatile, cannot be evaporated and dissipated in use and storage, can be recycled, eliminates the problem of environmental pollution caused by Volatile Organic Compounds (VOCs), has high conductivity and large electrochemical window, and can be used as the electrolyte for electrochemical research of a plurality of substances; (4) the solubility of the compound to inorganic matters, water, organic matters and polymers can be adjusted through the design of anions and cations, and the acidity of the compound can be adjusted to be super-acid; (5) the product has high polarity controllability, low viscosity and high density, can form a two-phase or multi-phase system, and is suitable for being used as a separation solvent or forming a new reaction-separation coupling system; (6) has good dissolving capacity for a large amount of inorganic and organic substances, has double functions of solvent and catalyst, and can be used as solvent or catalyst for many chemical reactionsActivating the carrier. Due to these specific properties and behavior of ionic liquids, it is believed to be associated with supercritical CO2Three green solvents are formed together with the aqueous two phases, and the method has wide application prospect.
The ionic liquid is of various types, and theoretically, the ionic liquid can reach 1018Many of them have physical and chemical properties that vary greatly with the structure, such as thermal stability, viscosity, volatility, melting point, glass transition temperature, etc., and these properties are often not compatible.
On the other hand, hydrogen energy is widely preferred as the cleanest energy; in the prior art, compressed hydrogen is transported by a hydrogen torpedo car, and is unloaded by utilizing the pressure difference in the hydrogen during the hydrogen transportation, so that the exhaust effect is further improved, hydraulic oil is usually injected into a corresponding steel cylinder in the prior art to facilitate the discharge of the hydrogen in the steel cylinder; after the compressed hydrogen in the steel cylinder is nearly exhausted, the hydraulic oil injected into the steel cylinder flows back to the oil storage device, so that the oil can be recycled.
However, most of the existing hydraulic oil adopts mineral oil, and has the following problems: (1) the hydraulic oil has poor thermal stability, and is easy to deform and hard to perform in a high-pressure environment such as a compressed hydrogen tank; (2) the hydraulic oil has high volatility and is easy to be entrained into compressed hydrogen through vaporization, so that the hydrogen is polluted and the purity of the hydrogen is influenced; (3) under high pressure, hydrogen can dissolve in the hydraulic oil, which also affects the venting effect.
Therefore, it is obvious that developing an ionic liquid composition specifically for compressing hydrogen gas, which simultaneously takes into account characteristics such as thermal stability, volatility, viscosity, melting point, glass transition temperature, etc., and can prevent hydrogen gas from dissolving in the composition, has an extraordinary significance, is a urgent need in the field, and will certainly lead to breakthrough development in the field.
Disclosure of Invention
The invention aims to provide an ionic liquid composition serving as a hydraulic hydrogenation working medium.
In order to achieve the purpose, the invention adopts the technical scheme that: an ionic liquid composition as a hydraulic hydrogenation working fluid, which comprises the following components in mass:
100 parts of ionic liquid;
1-5 parts of an additive;
wherein the general formula of the ionic liquid is as follows:
wherein: r1And R2The alkyl groups are the same or different and are respectively selected from saturated alkyl groups of C1-4; [ R ]2-SO4]-Is a methyl sulfate anion, an ethyl sulfate anion, a propyl sulfate anion or a butyl sulfate anion.
Hereinbefore, the preparation method of the ionic liquid is as follows: in N2Under protection, sequentially adding an imidazole derivative and a solvent toluene into a 250 mL three-neck flask, dropwise adding corresponding sulfate into the mixed solution, controlling the reaction temperature and stirring for reaction; and after the reaction is finished, pouring out the organic phase at the upper layer of the mixture, carrying out rotary evaporation on the ionic liquid phase at the lower layer, and carrying out vacuum drying to remove the solvent toluene to obtain the product.
Preferably, the ionic liquid of the ionic liquid composition is selected from one or more of the general formulas.
Preferably, the ionic liquid of the ionic liquid composition comprises 2 species, one of the general formulae being: the R is1Is methyl, R2Is ethyl, [ R ]2-SO4]-Is an ethyl sulfate anion; the other is as follows: the R is1And R2Are all ethyl, [ R ]2-SO4]-Is an ethyl sulfate anion.
Another preferred scheme is as follows: the R is1Is methyl, R2Is n-butyl, [ R ]2-SO4]-Is a butyl sulfate anion.
Preferably, the additives include a heat stabilizer, an antifoaming agent, a rust inhibitor and an extreme pressure antiwear agent.
The heat stabilizer can be one or more of phosphite, glyceride and epoxide, the defoaming agent can be mineral silicon oil and polyether substances, the antirust agent can be one or more of phosphate, fatty acid and derivatives thereof, and the extreme pressure antiwear agent is an organic metallic extreme pressure antiwear agent, such as molybdenum dialkyl dithiophosphate.
The additives may also include emulsifiers, dispersants, viscosity modifiers, gelling agents, sealing additives, foam inhibitors, free radical blockers, and water modifiers.
Preferably, the additive accounts for 1% or less of the ionic liquid by mass. Further preferably, the additive accounts for 0.01 to 0.95% of the ionic liquid, more preferably 0.1 to 0.7%, more preferably 0.2 to 0.6%, and more preferably 0.3 to 0.5%.
In the technical scheme, the volatility of the ionic liquid is less than 0.01g/h at 100 ℃, the ionic liquid is liquid at normal temperature, and the thermal decomposition temperature is more than 300 ℃.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
1. the invention develops a novel ionic liquid composition special for compressing hydrogen, and experiments prove that: the ionic liquid has excellent thermal stability and extremely low volatility, can prevent hydrogen from being dissolved in the composition, achieves remarkable effect, solves the problem in the field and can lead the field to achieve breakthrough development;
2. the ionic liquid composition specially used for compressing hydrogen developed by the invention is non-toxic and harmless, does not harm human bodies, and meanwhile, has lower cost and is suitable for industrial application.
Detailed Description
The invention will be further described with reference to the following examples:
example one
An ionic liquid composition as a hydraulic hydrogenation working fluid, which comprises the following components in mass:
100 parts of ionic liquid;
1 part of an additive;
wherein the general formula of the ionic liquid is as follows:
；
the ionic liquid of the ionic liquid composition comprises 2 species, one of the general formulas being: the R is1Is methyl, R2Is ethyl, [ R ]2-SO4]-Is an ethyl sulfate anion; the other is as follows: the R is1And R2Are all ethyl, [ R ]2-SO4]-Is an ethyl sulfate anion; the molar ratio of the two is 3: 1;
the additive comprises a heat stabilizer, a defoaming agent, an antirust agent and an extreme pressure antiwear agent.
Example two
An ionic liquid composition as a hydraulic hydrogenation working fluid, which comprises the following components in mass:
100 parts of ionic liquid;
1 part of an additive;
wherein the general formula of the ionic liquid is as follows:
wherein, said R1Is methyl, R2Is n-butyl, [ R ]2-SO4]-Is a butyl sulfate anion;
the additive comprises a heat stabilizer, a defoaming agent, an antirust agent and an extreme pressure antiwear agent.
Comparative example 1
The method is characterized in that commercially available hydraulic oil is used as a hydraulic hydrogenation working medium, and the hydraulic oil is high-pressure anti-wear hydraulic oil with a model number of L-HM100 produced by Shell company.
The products of the examples and comparative examples were tested and the results are shown in the following table:
| volatility (100 degree centigrade) | Temperature of thermal decomposition | |
| Example one | 0.009 mg/m3·h | 322℃ |
| Example two | 0.008 m g/m3·h | 310℃ |
| Comparative example 1 | 0.05 mg/m3·h | 210℃ |
The detection method comprises the following steps: the volatility is detected by adopting the national environmental protection standard HJ644-2013 of the people's republic of China to measure the volatile organic compounds in the ambient air. The thermal decomposition temperature is detected by adopting the petrochemical industry standard SH _ T0209-.
As can be seen from the above table, compared with the comparative ratio, the ionic liquid composition obtained by the present invention has excellent thermal stability, and is particularly suitable for the high pressure environment of the compressed hydrogen tank; in addition, the ionic liquid composition of the invention has very low volatility, does not generate vaporization and is entrained in compressed hydrogen, high purity of the hydrogen is ensured, and meanwhile, the hydrogen is not dissolved in the ionic liquid composition.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (7)
1. An ionic liquid composition as a hydraulic hydrogenation working fluid, which is characterized by comprising the following components in mass:
100 parts of ionic liquid;
1-5 parts of an additive;
wherein the general formula of the ionic liquid is as follows:
wherein: r1And R2The alkyl groups are the same or different and are respectively selected from saturated alkyl groups of C1-4; [ R ]2-SO4]-Is a methyl sulfate anion, an ethyl sulfate anion, a propyl sulfate anion or a butyl sulfate anion.
2. The ionic liquid composition of claim 1, wherein: the ionic liquid of the ionic liquid composition is selected from one or more of the general formulas.
3. The ionic liquid composition of claim 2, wherein: the ionic liquid of the ionic liquid composition comprises 2 species, one of the general formulas being: the R is1Is methyl, R2Is ethyl, [ R ]2-SO4]-Is an ethyl sulfate anion; the other is as follows: the R is1And R2Are all ethyl, [ R ]2-SO4]-Is an ethyl sulfate anion.
4. Such as rightThe ionic liquid composition of claim 1, wherein: the R is1Is methyl, R2Is n-butyl, [ R ]2-SO4]-Is a butyl sulfate anion.
5. The ionic liquid composition of claim 1, wherein: the additives include anti-corrosion additives, oxidation protection additives, acid interceptors, extreme pressure additives, and friction modifiers.
6. The ionic liquid composition of claim 1, wherein: the additive accounts for less than or equal to 1% of the ionic liquid by mass.
7. The ionic liquid composition of claim 1, wherein: the volatility of the ionic liquid is less than 0.01g/h at 100 ℃, the ionic liquid is liquid at normal temperature, and the thermal decomposition temperature is more than 300 ℃.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011469645.1A CN112442405A (en) | 2020-12-15 | 2020-12-15 | Ionic liquid composition as hydraulic hydrogenation working medium |
| PCT/CN2021/083738 WO2022126915A1 (en) | 2020-12-15 | 2021-03-30 | Ionic liquid composition as hydraulic hydrogenation working medium |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011469645.1A CN112442405A (en) | 2020-12-15 | 2020-12-15 | Ionic liquid composition as hydraulic hydrogenation working medium |
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| CN112442405A true CN112442405A (en) | 2021-03-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202011469645.1A Pending CN112442405A (en) | 2020-12-15 | 2020-12-15 | Ionic liquid composition as hydraulic hydrogenation working medium |
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| WO (1) | WO2022126915A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114085190A (en) * | 2021-11-12 | 2022-02-25 | 苏州金宏气体股份有限公司 | Ionic liquids, compositions and methods of making the same |
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| US20060060817A1 (en) * | 2004-09-23 | 2006-03-23 | Tempel Daniel J | Ionic liquid based mixtures for gas storage and delivery |
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| CN101023272A (en) * | 2004-09-24 | 2007-08-22 | 林德股份公司 | Method and device for compressing a gaseous medium |
| CN101189437A (en) * | 2005-05-06 | 2008-05-28 | 林德有限公司 | Liquid for compressing a gaseous medium and use of the same |
| US20100154924A1 (en) * | 2008-12-23 | 2010-06-24 | Texaco Inc. | Variable volume hydrogen storage |
| WO2019007556A1 (en) * | 2017-07-04 | 2019-01-10 | Linde Aktiengesellschaft | Ionic liquid comprising a dry lubricant |
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| CN106190483A (en) * | 2016-07-15 | 2016-12-07 | 山东源根石油化工有限公司 | A kind of complete synthesis antiwear hydraulic oil of environmental protection and energy saving and preparation method thereof |
| CN111139118A (en) * | 2019-12-26 | 2020-05-12 | 山东源根石油化工有限公司 | Environment-friendly energy-saving hydraulic oil and preparation method thereof |
| CN112408318B (en) * | 2020-12-15 | 2022-09-23 | 苏州金宏气体股份有限公司 | Ionic liquid composition for compressing hydrogen |
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2020
- 2020-12-15 CN CN202011469645.1A patent/CN112442405A/en active Pending
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2021
- 2021-03-30 WO PCT/CN2021/083738 patent/WO2022126915A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101023270A (en) * | 2004-09-17 | 2007-08-22 | 巴斯福股份公司 | Method for operating a liquid ring compressor |
| US20060060817A1 (en) * | 2004-09-23 | 2006-03-23 | Tempel Daniel J | Ionic liquid based mixtures for gas storage and delivery |
| CN101023272A (en) * | 2004-09-24 | 2007-08-22 | 林德股份公司 | Method and device for compressing a gaseous medium |
| CN101189437A (en) * | 2005-05-06 | 2008-05-28 | 林德有限公司 | Liquid for compressing a gaseous medium and use of the same |
| US20100154924A1 (en) * | 2008-12-23 | 2010-06-24 | Texaco Inc. | Variable volume hydrogen storage |
| WO2019007556A1 (en) * | 2017-07-04 | 2019-01-10 | Linde Aktiengesellschaft | Ionic liquid comprising a dry lubricant |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114085190A (en) * | 2021-11-12 | 2022-02-25 | 苏州金宏气体股份有限公司 | Ionic liquids, compositions and methods of making the same |
| CN114085190B (en) * | 2021-11-12 | 2023-09-12 | 金宏气体股份有限公司 | Ionic liquid, composition and preparation method thereof |
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| WO2022126915A1 (en) | 2022-06-23 |
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Application publication date: 20210305 |