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Phosphoester containing ethoxy unit, and preparation and use thereof

A technology of ethoxylate and phosphate ester, which is applied in the field of functional materials and chemical energy materials, can solve the problems of high price and inability to meet the electrochemical requirements of lithium-ion batteries, and achieve convenient synthesis, good flame retardancy, and mild reaction conditions. Effect

Inactive Publication Date: 2009-05-27
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reported fluorinated ethers (esters, sulfonates) and ionic liquids have good non-flammability when used as solvents, but such solvents are usually expensive and also have problems that cannot meet the electrochemical requirements of lithium-ion batteries (H.F. Xiang, H.Y.Xu, Z.Z.Wang, C.H.Chen, J.Power Sources[J], 173(2007)562.M. , A. Lewandowski, I. Stepniak, Electrochim. Acta [J], 51 (2006) 5567.)

Method used

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  • Phosphoester containing ethoxy unit, and preparation and use thereof
  • Phosphoester containing ethoxy unit, and preparation and use thereof
  • Phosphoester containing ethoxy unit, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] R=CH 3 , when n=1, the synthetic route is as follows:

[0018]

[0019] Add 12.42g of trimethyl phosphite, 12.46g of the above-mentioned compound 1 and 0.3g of anhydrous nickel chloride to the reaction vessel in sequence, and heat it to 130-140°C to fully react. In order to make the reaction fully, a three-necked flask can be used as the reaction vessel. The three-necked flask is equipped with a reflux condenser and a stirring magnet. The reaction is fully achieved by reflux. Usually, the reaction is 6 to 10 hours until no bubbles emerge. The reaction mixture is heated and collected under reduced pressure at 150 to 160°C. 119°C / 8-9mmHg component, the desired product can be obtained with a yield of 86.2%. Using FT-IR, 1 H NMR, 13 C NMR, 31 The product was characterized by P NMR and ESI HRMS, and the results confirmed that it was the target product 2. FT-IR (KBr): 1370.72 (P=O), 844.32 (P-O); 1 H NMR (CDCl 3 )δ: 3.36(s, 3H, -OCH 3 ), 3.55(t, 2H, -OCH 2 CH 2 O...

Embodiment 2

[0021] R=C 2 h 5 , when n=1, the synthetic route is as follows:

[0022]

[0023] Add 21.20 g of triethyl phosphite, 14.95 g of the above-mentioned compound 1 and 0.36 g of anhydrous nickel chloride to a three-necked flask equipped with a reflux condenser and a stirring magnet, and heat to reflux at 140-150° C. After 10 hours until no bubbles emerged, the reaction mixture was heated after cooling, and the 136-138°C / 8-9mmHg component was collected by vacuum distillation at 160-170°C to obtain the desired product with a yield of 81.6%. Using FT-IR, 1 HNMR, 13 C NMR, 31 The product was characterized by P NMR and ESI HRMS, and the results confirmed that it was the target product 3. FT-IR (KBr): 1393.28 (P=O), 794.75 (P-O); 1 H NMR (CDCl 3 )δ: 1.32(t,6H,-OCH 2 CH 3 ), 3.32(s, 3H, -OCH 3 ), 3.45~3.8(m, 4H, -OCH 2 CH 2 OCH 3 ), 3.83 (d, 2H, -P-CH 2 -), 3.97~4.32(m, 4H, -OCH 2 CH 3 ); 13 C NMR (CDCl 3 )δ: 16.6~16.7, 59.2, 62.5~62.6, 64.4, 66.6, 71.9~72.6; 31 P NM...

Embodiment 3

[0025] R=CF 3 CH 2 , when n=1, the synthetic route is as follows:

[0026]

[0027] Add 28.88g three-(2,2,2-trifluoroethyl) phosphite successively in the there-necked flask that reflux condenser and stirring magnet are housed, 9.97g above-mentioned compound 1 and 0.24g anhydrous nickel chloride, Heat to reflux at 150-170°C, react for 6-10 hours until no bubbles come out, heat the reaction mixture after cooling, and collect the 128-130°C / 8-9mmHg components by vacuum distillation at 150-160°C to obtain Desired product in 79.9% yield. Using FT-IR, 1 H NMR, 13 C NMR and 31 The product was characterized by P NMR, and the result confirmed that it was the target product 4. FT-IR (KBr): 1372.04 (P=O), 846.59 (P-O); 1 H NMR (CDCl 3 )δ: 4.39 ~ 4.49 (m, 4H, -OCH 2 CF 3 ), 3.35(s, 3H, -OCH 3 ), 4.01~4.04 (m, 2H, P-CH 2 -), 3.12~3.54(t, 2H, -OCH 2 CH 2 OCH 3 ), 3.71~3.77 (t, 2H, -OCH 2 CH 2 OCH 3 ); 13 C NMR (CDCl3 )δ: 59.1, 61.9~63.5, 64.3, 66.5, 71.9~73.0, 120.1~124...

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Abstract

The invention discloses organic phosphates containing an ethyoxyl (CH2CH20) unit, a preparation method and application thereof. The organic phosphates have the following structural general formula: in the formula, n is 1 or 2; R can be CH3 or C2H5 or CF3CH2; and radicals of two R are the same. The preparation method is to heat ethylene glycol monomethyl ether containing chloromethyl or diethylene glycol monomethyl ether containing the chloromethyl and phosphite ester containing an R radical as raw materials by taking absolute nickelous chloride as a catalyst for a sufficient reaction, and distill at reduced pressure so as to obtain the organic phosphate. The organic phosphate prepared by the method has excellent flame retardance, thermal stability and excellent electrochemistry performance, can be used as secondary lithium ion battery high-safety electrolysing solution, and has wide industrial application prospect. The method has the advantages of simple steps, short time, completion in a common laboratory and easy popularization.

Description

technical field [0001] The invention relates to a kind of phosphoric acid ester containing ethoxy unit and its preparation method and application, and belongs to the technical field of functional materials and chemical energy materials. Background technique [0002] Safety issues have become an important factor restricting the development and application of lithium-ion batteries, especially when it comes to high-energy battery packs used in electric vehicles and hybrid electric vehicles, safety issues are particularly prominent. Safety issues are mainly caused by highly active electrode materials and highly flammable compounds in the electrolyte. Lithium-ion batteries tend to generate heat internally when subjected to abuse, causing a dramatic rise in temperature that can eventually lead to a serious fire hazard or even an explosion. Therefore, it is very important to find an effective method to prevent the fire and explosion caused by lithium-ion batteries. [0003] In re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09H01M10/40
CPCY02E60/122Y02E60/10
Inventor 吴磊严琨李早英
Owner WUHAN UNIV
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