Heteropoly tridemorph quaternary ammonium salt as well as preparation method and application of quaternary ammonium salt

A technology of tridemorpholine and quaternary ammonium salt, which is applied in the field of preparation of tridemorpholine quaternary ammonium salt of heteropolyacid, can solve the problems of difficult recovery, lower use cost, poor solubility, etc., and achieve simplified production process and high activity , the effect of easy separation

Inactive Publication Date: 2014-06-25
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the heteropoly acid has good water solubility and poor solubility in the organic phase. In the actual application process, there is unstable catalytic activity caused by uneven distribution.
At the same time, its good water solubility makes recycling difficult, and compared with other acid catalysts, the price is high, and the disadvantages of high price and difficulty in recycling make it impossible to apply to industrial production; supported heteropolyacid catalysts reduce the cost of use, At the same time, the catalytic performance has been improved, but further research is needed for practical application.

Method used

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  • Heteropoly tridemorph quaternary ammonium salt as well as preparation method and application of quaternary ammonium salt
  • Heteropoly tridemorph quaternary ammonium salt as well as preparation method and application of quaternary ammonium salt

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Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1: the preparation of tridemorpholine quaternary ammonium salt

[0019] 44.6g (0.150mol) tridecylmorpholine and 20.6g (0.150mol) n-butyl bromide were stirred and reacted at 120°C for 48 hours to obtain a yellow semi-solid crude product, which was recrystallized from ethyl acetate to obtain tridecabromide as a pale yellow solid Morpholine n-butylammonium 63.2g, yield 96.9%.

Embodiment 2

[0020] Embodiment 2: Preparation of n-butyl trimorpholine ammonium phosphotungstic acid

[0021] 4.3g (0.010mol) n-butyl trimorphinium bromide and 28.8g (0.010mol) H 3 PW 12 o 40 Heat to reflux in 100mL of 1,2-dichloroethane, stir the reaction, use the suction device to absorb the hydrogen bromide generated, until no hydrogen bromide gas is generated, distill off the solvent to obtain 32.3g of milky white n-butyl phosphotungstic acid Trimorpholine ammonium salt, 100% yield.

[0022] The assay result of gained phosphotungstic acid n-tridemorpholine quaternary ammonium salt:

[0023] H NMR spectrum ( 1 H NMR, 300MHz, D 2 O) δ3.67-3.61(m, 2H), 3.52-3.49(m, 4H), 3.24-3.22(m, 4H), 1.34-1.32(m, 22H), 1.73(m, 4H), 1.21(d , J=7.2Hz, 6H), 0.97(t, J=7.2Hz, 3H), 0.96(t, J=7.2Hz, 3H).

[0024] Fourier transform infrared spectrum (potassium bromide tablet): 3404cm -1 (broad front) is the stretching vibration peak of H-O bond; 2959cm -1 、2873cm -1 It is the stretching vibration pe...

Embodiment 3

[0025] Embodiment 3: the preparation of epoxidized soybean oil

[0026] Install an electric mixer and a reflux condenser on a 250mL three-necked bottle, add 100.0g soybean oil (130 iodine value, 0.50 acid value), 2.0g n-butyltridecmorpholine ammonium phosphotungstic acid catalyst to the bottle, and control the reaction temperature 55°C, under stirring, slowly add 65mL of 30% hydrogen peroxide dropwise through the constant pressure dropping funnel. Determination, the epoxy value is 6.3%, the iodine value is 4.25g / 100g, and the acid value is 0.35mg / g.

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Abstract

The invention discloses heteropoly tridemorph quaternary ammonium salt as well as a preparation method and application of the quaternary ammonium salt. The heteropoly tridemorph quaternary ammonium salt is prepared from a two-step reaction, i.e., alkylation of tridemorph and anion exchange. The compound, as an epoxidation catalyst, is applicable to preparation of epoxidized soybean oil through an epoxidation reaction of soybean oil and hydrogen peroxide. The heteropoly tridemorph quaternary ammonium salt disclosed by the invention has the advantages that the heteropoly tridemorph quaternary ammonium, as a catalyst for preparing the epoxidized soybean oil through the soybean oil, is not only high in catalytic activity, but also easy to separate and recover after the reaction and good in repeated use performance.

Description

technical field [0001] The invention relates to a preparation method of tridemorpholine quaternary ammonium salt of heteropoly acid. Background technique [0002] Heteropolyacids have unique acidity and redox properties, and are less corrosive. They are good catalysts for the epoxidation of soybean oil and hydrogen peroxide to prepare epoxidized soybean oil. However, the heteropoly acid has good water solubility and poor solubility in the organic phase, and has unstable catalytic activity caused by uneven distribution in the actual application process. At the same time, its good water solubility makes recycling difficult, and compared with other acid catalysts, the price is high, and the disadvantages of high price and difficulty in recycling make it impossible to apply to industrial production; supported heteropolyacid catalysts reduce the cost of use, At the same time, the catalytic performance has been improved, but further research is needed for practical application. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/30B01J31/34C11C3/00
CPCB01J31/34B01J2231/72C07D265/30C07D303/42C07D413/06C11C3/006Y02P20/584
Inventor 吴锦明沈爱宝史春越蔡燕曹亚云
Owner NANTONG UNIVERSITY
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