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Aromatic dicarboxylic acid ionic liquid, as well as preparation method and application thereof

An aromatic dicarboxylic acid and ionic liquid technology, applied in the chemical industry, can solve problems such as unsatisfactory thermal stability, and achieve ideal thermal stability, excellent anti-friction and anti-wear properties.

Active Publication Date: 2019-03-19
BAOJI UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the thermal decomposition temperature of these ionic liquids is 165-177 ° C, and the thermal stability is not ideal

Method used

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  • Aromatic dicarboxylic acid ionic liquid, as well as preparation method and application thereof
  • Aromatic dicarboxylic acid ionic liquid, as well as preparation method and application thereof
  • Aromatic dicarboxylic acid ionic liquid, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Preparation of 5-butoxy-1,3-isophthalic acid diquaternary ammonium salt

[0031] (1) Weigh 25.9353 g of 5-hydroxy-1,3-benzenedicarboxylic acid, 6.8665 g of p-toluenesulfonic acid, and 89.6000 g of methanol into a round bottom flask. Reflux at 75°C for 24 hours. After the reaction, methanol was distilled off, washed with saturated brine, extracted with ethyl acetate, allowed to stand, separated into layers, and dried. The product, methyl 5-hydroxy-1,3-phthalate, was obtained.

[0032] (2) Methyl 5-hydroxy-1,3-phthalate: Potassium carbonate: 1-bromobutane with a molar ratio of 1:2.5:1.4 Weigh 34.6800g of potassium carbonate and 19.3760g of 1-bromobutane Sequentially add to the flask, add an appropriate amount of N,N-dimethylformamide. Reflux at 85°C for 24 hours. After the reaction, filter off K while hot 2 CO 3 , washed 2 to 3 times with water to remove unreacted K 2 CO 3 . Extract 3 times with petroleum ether, take the organic phase, add anhydrous...

Embodiment 2

[0038] Example 2: Preparation of 5-octyloxy-1,3-isophthalic acid diquaternary ammonium salt

[0039] (1) Weigh 25.9353 g of 5-hydroxy-1,3-benzenedicarboxylic acid, 6.8665 g of p-toluenesulfonic acid, and 89.6000 g of methanol into a round bottom flask. Reflux at 75°C for 24 hours. After the reaction, methanol was distilled off, washed with saturated brine, extracted with ethyl acetate, allowed to stand, separated into layers, and dried. The product, methyl 5-hydroxy-1,3-phthalate, was obtained.

[0040] (2) Methyl 5-hydroxy-1,3-phthalate: Potassium carbonate: 1-bromooctane with a molar ratio of 1:2.5:1.4 Weigh 34.6800g of potassium carbonate and 19.3760g of 1-bromooctane Sequentially add to the flask, add an appropriate amount of N,N-dimethylformamide. Reflux at 85°C for 24 hours. After the reaction, filter off K while hot 2 CO 3 , washed 2 to 3 times with water to remove unreacted K 2 CO 3 . Extract 3 times with petroleum ether, take the organic phase, add anhydrous ...

Embodiment 3

[0046] Example 3: Preparation of 5-dodecyloxy-1,3-isophthalic acid diquaternary ammonium salt

[0047] (1) Weigh 25.9353 g of 5-hydroxy-1,3-benzenedicarboxylic acid, 6.8665 g of p-toluenesulfonic acid, and 89.6000 g of methanol into a round bottom flask. Reflux at 75°C for 24 hours. After the reaction, methanol was distilled off, washed with saturated brine, extracted with ethyl acetate, allowed to stand, separated into layers, and dried. The product, methyl 5-hydroxy-1,3-phthalate, was obtained.

[0048] (2) Methyl 5-hydroxy-1,3-phthalate: Potassium carbonate: 1-bromododecane in a molar ratio of 1:2.5:1.4 Weigh 34.6800g of potassium carbonate, 1-bromododecane 19.3760g was added to the flask in sequence, and an appropriate amount of N,N-dimethylformamide was added. Reflux at 85°C for 24 hours. After the reaction, filter off K while hot 2 CO 3 , washed 2 to 3 times with water to remove unreacted K 2 CO 3 . Extract 3 times with petroleum ether, take the organic phase, a...

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Abstract

The invention provides an aromatic dicarboxylic acid ionic liquid, as well as a preparation method and application thereof. The ionic liquid has a structure as shown in a general formula (I), whereinR1, R2, R3 and R4 are independently and respectively selected from alkyl having carbon atom number of 1-18, and n is an arbitrary integer of 2-12. Due to the intense adsorption effect of two polar carboxyl (-COO-) and introduction of rigid benzene ring, the ionic liquid can form a firm and orderly physical adsorption protective film on the surface of a metal friction pair in the friction process and has excellent friction reduction and abrasion resistance. Furthermore, the aromatic dicarboxylic acid ionic liquid has relatively ideal thermal stability and the highest decomposition temperature of 205 DEG C.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to an aromatic dicarboxylic acid ionic liquid which can be used as a lubricant and a preparation method thereof. Background technique [0002] Friction and wear is one of the main causes of material loss. According to incomplete statistics, 1 / 3 to 1 / 2 of energy is consumed in friction and wear, and about 80% of machine parts failure is caused by wear, so friction and wear Effective control is particularly important. Reducing friction and reducing wear can effectively meet the needs of many industrial developments, which involve basic fields such as manufacturing, pharmaceuticals, energy efficiency and environmental protection, and lubrication technology is an effective way to solve the above problems. Ionic liquids (ILS) have excellent physical and chemical properties such as low volatility, good thermal stability, good electrical conductivity, wide liquid ran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/63C07C65/21C07C51/41C10M133/06C10M129/54C10N30/08C10N30/06
CPCC07C65/21C07C211/63C10M129/54C10M133/06C10M2207/144C10M2215/04C10N2030/06C10N2030/08C10N2020/077
Inventor 凡明锦李文倩董瑞马琳韩云燕
Owner BAOJI UNIV OF ARTS & SCI
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