WO2022126915A1 - 一种作为液压式加氢工质的离子液体组合物 - Google Patents

一种作为液压式加氢工质的离子液体组合物 Download PDF

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WO2022126915A1
WO2022126915A1 PCT/CN2021/083738 CN2021083738W WO2022126915A1 WO 2022126915 A1 WO2022126915 A1 WO 2022126915A1 CN 2021083738 W CN2021083738 W CN 2021083738W WO 2022126915 A1 WO2022126915 A1 WO 2022126915A1
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ionic liquid
liquid composition
sulfate anion
ethyl
additives
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French (fr)
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徐聪
张红敏
吴丽丽
程宇
王新喜
孙猛
金向华
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苏州金宏气体股份有限公司
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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

Definitions

  • the invention relates to the field of ionic liquid materials, in particular to an ionic liquid composition used as a working fluid for hydraulic hydrogenation.
  • ionic liquids refer to liquids composed entirely of ions.
  • KCI and KOH are in a liquid state at high temperature, and in this case, they are ionic liquids.
  • Substances composed of ions that are liquid at or near room temperature are called room temperature ionic liquids, room temperature molten salts, organic ionic liquids, etc.
  • room temperature ionic liquids the force between anions and cations is the Coulomb force, and its magnitude is related to the number of charges and the radius of the anions and cations.
  • the anions and cations of some ionic compounds are bulky and loose, resulting in low forces between them, such that the melting point is close to room temperature.
  • ionic liquids When compared with traditional organic solvents and electrolytes, ionic liquids have a series of outstanding advantages: (1) a wide range of liquid states, from below or near room temperature to above 300 degrees Celsius, with high thermal and chemical stability; ( 2) The vapor pressure is very small, non-volatile, and will not be evaporated and lost during use and storage, and can be recycled, eliminating the environmental pollution problem of volatile organic compounds (VOCs, namely volatile organic compounds).
  • VOCs volatile organic compounds
  • ionic liquids There are many types of ionic liquids, which can theoretically reach as many as 10 18 types, and their physical and chemical properties will vary greatly with the structure, such as thermal stability, viscosity, volatility, melting point, glass transition temperature, etc. , and these properties are often not at the same time.
  • hydrogen energy is widely respected as one of the cleanest energy sources; in the prior art, compressed hydrogen is transported by hydrogen torpedo vehicles, and the pressure difference inside is also used to unload when hydrogen is transported.
  • hydraulic oil is usually injected into the corresponding steel cylinder to facilitate the discharge of hydrogen pressure in the cylinder; after the compressed hydrogen in the cylinder is nearly emptied, the hydraulic oil injected into it Return to the oil storage device, so that the oil can be reused.
  • the object of the present invention is to provide an ionic liquid composition as a working fluid for hydraulic hydrogenation.
  • the technical scheme adopted in the present invention is: a kind of ionic liquid composition as hydraulic type hydrogenation working medium, in mass, comprising:
  • R 1 and R 2 are the same or different, and are respectively selected from C1-4 saturated alkyl groups; [R 2 -SO 4 ] - is methyl sulfate anion, ethyl sulfate anion, propyl sulfate anion or butyl sulfate anion .
  • the preparation method of the ionic liquid is as follows: under the protection of N , add imidazole derivatives and solvent toluene successively to the 250mL three - necked flask, and dropwise add the corresponding sulfate to the above-mentioned mixed solution, control the reaction temperature and The reaction was stirred; after the reaction was completed, the organic phase in the upper layer of the mixture was poured out, the ionic liquid phase in the lower layer was rotary evaporated, and the solvent toluene was removed by vacuum drying to obtain the product.
  • the ionic liquid of the ionic liquid composition is selected from one or more of the general formulae.
  • the ionic liquid of the ionic liquid composition includes two kinds, and in the general formula, one is: the R 1 is methyl, R 2 is ethyl, and [R 2 -SO 4 ] - is sulfuric acid Ethyl ester anion; the other is: both R 1 and R 2 are ethyl, and [R 2 -SO 4 ] - is ethyl sulfate anion.
  • R 1 is methyl
  • R 2 is n-butyl
  • [R 2 -SO 4 ] - is butyl sulfate anion.
  • the additives include heat stabilizers, defoaming agents, rust inhibitors and extreme pressure antiwear agents.
  • the thermal stabilizer can be one or more of phosphites, glycerides and epoxides
  • the defoaming agent can be mineral silicone oils and polyethers
  • the rust inhibitor can be phosphate esters, fatty acids and the like.
  • the extreme pressure antiwear agent is an organometallic extreme pressure antiwear agent, such as molybdenum dialkyldithiophosphate.
  • the additives may also include emulsifiers, dispersants, viscosity modifiers, gelling agents, sealing additives, foam inhibitors, free radical interceptors, and water conditioners.
  • the additive accounts for less than or equal to 1% of the ionic liquid in terms of mass. Further preferably, the additive accounts for 0.01-0.95% of the ionic liquid, more preferably 0.1-0.7%, more preferably 0.2-0.6%, more preferably 0.3-0.5%.
  • the volatility of the ionic liquid is less than 0.01 g/h at 100 degrees Celsius, it is liquid at room temperature, and the thermal decomposition temperature is greater than 300 degrees Celsius.
  • the present invention has the following advantages compared with the prior art:
  • the present invention has developed a new ionic liquid composition specially used for compressing hydrogen.
  • the ionic liquid not only has excellent thermal stability, but also has extremely low volatility, which can prevent hydrogen from dissolving in the composition. , achieved remarkable results, solved the problems in this field, and made breakthroughs in this field;
  • the ionic liquid composition specially developed for compressing hydrogen gas is non-toxic and harmless, and will not cause harm to the human body. At the same time, the cost of the composition is also low, and it is suitable for industrial application.
  • An ionic liquid composition as a working fluid for hydraulic hydroprocessing, by mass comprising:
  • the ionic liquid of the ionic liquid composition includes two kinds, and in the general formula, one is: the R 1 is a methyl group, R 2 is an ethyl group, and [R 2 -SO 4 ] - is an ethyl sulfate anion The other is: the R 1 and R 2 are both ethyl groups, and [R 2 -SO 4 ] - is an ethyl sulfate anion; the molar ratio of the two is 3:1;
  • the additives include heat stabilizers, defoaming agents, rust inhibitors and extreme pressure antiwear agents.
  • An ionic liquid composition as a working fluid for hydraulic hydroprocessing, by mass comprising:
  • the general formula of the ionic liquid is as follows: Wherein, the R 1 is methyl, R 2 is n-butyl, and [R 2 -SO 4 ] - is butyl sulfate anion;
  • the additives include heat stabilizers, defoaming agents, rust inhibitors and extreme pressure antiwear agents.
  • a commercially available hydraulic oil was used as the hydraulic hydrogenation working fluid, and the hydraulic oil was a high-pressure anti-wear hydraulic oil with the L-HM100 label produced by Shell.
  • the ionic liquid composition of the present invention has excellent thermal stability, and is especially suitable for the high pressure environment of compressed hydrogen tank; in addition, the volatility of the ionic liquid composition of the present invention is very high. It is small, and will not be entrained into the compressed hydrogen gas by vaporization, which ensures the high purity of the hydrogen gas, and at the same time, the hydrogen gas is insoluble in the ionic liquid composition.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

本发明公开了一种作为液压式加氢工质的离子液体组合物，以质量计，包括：离子液体100份；添加剂0～5份；其中，所述离子液体的通式(I)如下：其中：R 1和R 2相同或不同，分别选自C1～4的饱和烷基；[R 2-SO 4] -为硫酸甲酯阴离子、硫酸乙酯阴离子、硫酸丙酯阴离子或硫酸丁酯阴离子。实验证明：该离子液体不仅具有优异的热稳定性，而且挥发性极低，可以防止氢气溶解于组合物之中，取得了显著的效果，解决了本领域的难题，可以使得本领域取得突破性发展。

Description

一种作为液压式加氢工质的离子液体组合物 技术领域
本发明涉及离子液体材料领域，具体涉及一种作为液压式加氢工质的离子液体组合物。
背景技术
现有技术中，离子液体(或称离子性液体)是指全部由离子组成的液体，如高温下的KCI、KOH呈液体状态，此时它们就是离子液体。在室温或室温附近温度下呈液态的由离子构成的物质，称为室温离子液体、室温熔融盐、有机离子液体等，尚无统一的名称，但倾向于简称离子液体。在离子化合物中，阴阳离子之间的作用力为库仑力，其大小与阴阳离子的电荷数量及半径有关，离子半径越大，它们之间的作用力越小，这种离子化合物的熔点就越低。某些离子化合物的阴阳离子体积很大，结构松散，导致它们之间的作用力较低，以至于熔点接近室温。
在与传统有机溶剂和电解质相比时，离子液体具有一系列突出的优点：(1)液态范围宽，从低于或接近室温到300摄氏度以上，有高的热稳定性和化学稳定性；(2)蒸汽压非常小，不挥发，在使用、储藏中不会蒸发散失，可以循环使用，消除了挥发性有机化合物(VOCs，即volatile organic compounds)环境污染问题，(3)电导率高，电化学窗口大，可作为许多物质电化学研究的电解液；(4)通过阴阳离子的设计可调节其对无机物、水、有机物及聚合物的溶解性，并且其酸度可调至超酸；(5)具有较大的极性可调控性，粘度低，密度大，可以形成二相或多相体系，适合作分离溶剂或构成反应—分离耦合新体系；(6)对大量无机和有机物质都表现处良好的溶解能力，且具有溶剂和催化剂的双重功能，可以作为许多化学反应溶剂或催化活性载体。由于离子液体的这些特殊性质和表现，它被认为与超临界CO 2和双水相一起构成三大绿色溶剂，具有广阔的应用前景。
离子液体的种类很多，从理论上来讲可以达到10 18种之多，其物理化学性质会随着结构而有较大的变化，例如热稳定性、粘度、挥发性、熔点、玻璃化温度等等，而且这些性能往往不能同时兼顾。
另一方面，氢能源作为一种最清洁的能源而被广泛推崇；现有技术中，压缩氢气都是通过氢气鱼雷车来运输的，在传输氢气时，也是利用其内的压力差来卸料，为了进一步提高排气效果，现有技术中通常会向对应的钢瓶注入液压油，以有助于钢瓶内压氢气排出；等钢瓶内的压缩氢气接近排空后，使注入到其中的液压油回流到储油装置，从而使得油能够重复循环使用。
然而，现有的液压油大都采用的是矿物油，存在如下问题：(1)液压油的热稳定性差，尤其是在压缩氢气罐这种高压环境下容易发生形变，难以胜任；(2)液压油的挥发性较大，其容易通过汽化夹带到压缩氢气中，从而污染氢气，影响其纯度；(3)在高压状态下，氢气可以溶解于液压油之中，这一点也会影响其排气效果。
因此，开发一种专门用于压缩氢气的离子液体组合物，使其同时兼顾热稳定性、挥发性、粘度、熔点、玻璃化温度等特性，并可以防止氢气溶解于组合物之中，显然具有非凡的意义，更是本领域的当务之急，也必然会使得本领域取得突破性发展。
发明内容
本发明的目的是提供一种作为液压式加氢工质的离子液体组合物。
为达到上述目的，本发明采用的技术方案是：一种作为液压式加氢工质的离子液体组合物，以质量计，包括：
离子液体  100份；
添加剂    1～5份；
其中，所述离子液体的通式如下：
Figure PCTCN2021083738-appb-000001
其中：R 1和R 2相同或不同，分别选自C1～4的饱和烷基；[R 2-SO 4] -为硫酸甲酯阴离子、硫酸乙酯阴离子、硫酸丙酯阴离子或硫酸丁酯阴离子。
上文中，所述离子液体的制备方法如下：在N 2保护下，向250mL三口烧瓶中依次加入咪唑衍生物、溶剂甲苯，并逐滴滴加相应硫酸酯至上述混合 液中，控制反应温度并搅拌反应；反应结束后，将混合物上层的有机相倒出，下层的离子液体相旋蒸，真空干燥除去溶剂甲苯，即得到产物。
优选的，所述离子液体组合物的离子液体选自所述通式中的一种或几种。
优选的，所述离子液体组合物的离子液体包括2种，所述通式中，一种是：所述R 1为甲基，R 2为乙基，[R 2-SO 4] -为硫酸乙酯阴离子；另一种是：所述R 1和R 2都为乙基，[R 2-SO 4] -为硫酸乙酯阴离子。
优选的另一种方案：所述R 1为甲基，R 2为正丁基，[R 2-SO 4] -为硫酸丁酯阴离子。
优选的，所述添加剂包括热稳定剂、消泡剂、防锈剂和极压抗磨剂。
所述热稳定剂可以是亚磷酸盐、甘油酯和环氧化物中的一种或多种、消泡剂可以是矿物硅油类和聚醚类物质、防锈剂可以是磷酸酯、脂肪酸及其衍生物中的一种或几种、极压抗磨剂为有机金属性极压抗磨剂，如二烷基二硫代磷酸氧钼。
所述添加剂还可以包括乳化剂、分散剂、粘度调节剂、胶凝剂、密封添加剂、泡沫抑制剂、自由基拦截剂和水调节剂。
优选的，以质量计，所述添加剂占离子液体的量少于等于1％。进一步优选的，所述添加剂占离子液体的量为0.01～0.95％，更优选为0.1～0.7％，更优选为0.2～0.6％，更优选为0.3～0.5％。
上述技术方案中，所述离子液体的挥发性在100摄氏度时小于0.01g/h，常温下为液体，热分解温度大于300℃。
由于上述技术方案运用，本发明与现有技术相比具有下列优点：
1、本发明研发了一种新的专门用于压缩氢气的离子液体组合物，实验证明：该离子液体不仅具有优异的热稳定性，而且挥发性极低，可以防止氢气溶解于组合物之中，取得了显著的效果，解决了本领域的难题，可以使得本领域取得突破性发展；
2、本发明研发的专门用于压缩氢气的离子液体组合物无毒无害，不会对人体产生伤害，同时，该组合物的成本也较低，适于工业化应用。
具体实施方式
结合实施例对本发明作进一步描述：
实施例一
一种作为液压式加氢工质的离子液体组合物，以质量计，包括：
离子液体  100份；
添加剂    1份；
其中，所述离子液体的通式如下：
Figure PCTCN2021083738-appb-000002
所述离子液体组合物的离子液体包括2种，所述通式中，一种是：所述R 1为甲基，R 2为乙基，[R 2-SO 4] -为硫酸乙酯阴离子；另一种是：所述R 1和R 2都为乙基，[R 2-SO 4] -为硫酸乙酯阴离子；两者的摩尔比为3:1；
所述添加剂包括热稳定剂、消泡剂、防锈剂和极压抗磨剂。
实施例二
一种作为液压式加氢工质的离子液体组合物，以质量计，包括：
离子液体  100份；
添加剂    1份；
其中，所述离子液体的通式如下：
Figure PCTCN2021083738-appb-000003
其中，所述R 1为甲基，R 2为正丁基，[R 2-SO 4] -为硫酸丁酯阴离子；
所述添加剂包括热稳定剂、消泡剂、防锈剂和极压抗磨剂。
对比例一
采用市售的液压油作为液压式加氢工质，所述液压油为壳牌公司生产的型号为L-HM100标号的高压抗磨液压油。
将实施例和对比例的产品进行检测，结果如下表所示：
  挥发性(100摄氏度) 热分解温度
实施例一 0.009mg/m 3·h 322℃
实施例二 0.008m g/m 3·h 310℃
对比例一 0.05mg/m 3·h 210℃
上述检测方法分别是：采用中华人民共和国国家环境保护标准HJ644-2013环境空气挥发性有机物的测定，来检测挥发性。采用中华人民共和国石油化工行业标准SH_T 0209-1992(2004)《压油热稳定性测定法检测热分解温度》。
由上表可见，相比对比例，本发明得到的离子液体组合物具有优异的热稳定性，尤其适用于压缩氢气罐这种高压环境下；此外，本发明的离子液体组合物的挥发性非常小，不会出现汽化而夹带到压缩氢气中，保证了氢气的高纯度，同时氢气也不溶于该离子液体组合物之中。
对所公开的实施例的上述说明，使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的，本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下，在其它实施例中实现。因此，本发明将不会被限制于本文所示的这些实施例，而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。

Claims (7)

  1. 一种作为液压式加氢工质的离子液体组合物，其特征在于，以质量计，包括：
    离子液体    100份；
    添加剂      1～5份；
    其中，所述离子液体的通式如下：
    Figure PCTCN2021083738-appb-100001
    其中：R 1和R 2相同或不同，分别选自C1～4的饱和烷基；[R 2-SO 4] -为硫酸甲酯阴离子、硫酸乙酯阴离子、硫酸丙酯阴离子或硫酸丁酯阴离子。
  2. 如权利要求1所述的离子液体组合物，其特征在于：所述离子液体组合物的离子液体选自所述通式中的一种或几种。
  3. 如权利要求2所述的离子液体组合物，其特征在于：所述离子液体组合物的离子液体包括2种，所述通式中，一种是：所述R 1为甲基，R 2为乙基，[R 2-SO 4] -为硫酸乙酯阴离子；另一种是：所述R 1和R 2都为乙基，[R 2-SO 4] -为硫酸乙酯阴离子。
  4. 如权利要求1所述的离子液体组合物，其特征在于：所述R 1为甲基，R 2为正丁基，[R 2-SO 4] -为硫酸丁酯阴离子。
  5. 如权利要求1所述的离子液体组合物，其特征在于：所述添加剂包括防腐添加剂、氧化保护添加剂、酸拦截剂、极压添加剂和摩擦改进剂。
  6. 如权利要求1所述的离子液体组合物，其特征在于：以质量计，所述添加剂占离子液体的量少于等于1％。
  7. 如权利要求1所述的离子液体组合物，其特征在于：所述离子液体的挥发性在100摄氏度时小于0.01g/h，常温下为液体，热分解温度大于300℃。
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