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Method for preparing organic carboxylate from olefin through hydroesterification

A technology of organic carboxylate and olefin hydrogen ester, which is applied in the preparation of carbon monoxide or formate, chemical instruments and methods, organic chemistry, etc., can solve the problems of increased investment cost, complicated post-processing, equipment corrosion, etc., and achieve structural Can be designed to promote high-efficiency, low-corrosion effects

Inactive Publication Date: 2012-07-04
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the traditional acid accelerator shows good performance in the hydroesterification reaction, due to its strong acidity, the equipment is severely corroded, so that the hydroesterification reaction needs to be carried out in an acid-resistant reactor, and there is also a complicated post-treatment , serious environmental pollution and other defects will inevitably bring about an increase in investment costs for future industrial applications

Method used

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  • Method for preparing organic carboxylate from olefin through hydroesterification
  • Method for preparing organic carboxylate from olefin through hydroesterification
  • Method for preparing organic carboxylate from olefin through hydroesterification

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] In a 60ml autoclave, sequentially add Pd(OAc) 2 : 0.01mmol, PPh 3 : 0.04mmol, acidic ionic liquid a: 0.1mmol, anhydrous methanol: 10mL, seal the reactor, replace the reactor 3 times with carbon monoxide, charge ethylene: 2g (66.7mmol), and then charge carbon monoxide until the reactor pressure is 4.0MPa. The temperature was controlled by the temperature controller to slowly rise to 80°C, react for 4 hours, cool to room temperature, and unload the kettle. The liquid obtained from the reaction was qualitatively analyzed by Agilent 6890 / 5973 GC and quantitatively analyzed by Agilent 6820 gas chromatography. Ethylene The conversion rate was 98%, and the selectivity of the product methyl propionate was 99%.

Embodiment 2

[0031] With embodiment 1, acidic ionic liquid promotor used is b-y (wherein the single nucleic acid ionic liquid consumption is 0.1mmol, and the binuclear ionic liquid consumption is 0.05mmol), reaction result is shown in the following table:

[0032]

[0033]

Embodiment 3

[0035] In a 60ml autoclave, sequentially add Pd(OAc) 2 : 0.01mmol, dtbpmb: 0.02mmol, acidic ionic liquid a: 0.1mmol, anhydrous methanol: 10mL, seal the reactor, replace the reactor with carbon monoxide for 3 times, fill with ethylene: 2g (66.7mmol), and then fill with carbon monoxide When the pressure of the reactor is 4.0 MPa, the reaction is carried out at 80° C. for 4 hours, the conversion rate of ethylene is 99%, and the selectivity of the product methyl propionate is 99%.

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Abstract

The invention discloses a method for preparing organic carboxylate from olefin through hydroesterification. Terminal olefin, carbon monoxide and an alcoholic compound is catalyzed by a catalyst consisting of a palladium complex, a phosphine ligand and an acid ionic liquid to form the organic carboxylate of which the carbon atom number is one more than that of the olefin. The method has the advantages of mild reaction conditions, wide raw material applicability, high product selectivity and the like. Compared with an organic or inorganic acid accelerator widely used in the conventional hydroesterification, the acid ionic liquid has a small using amount and low corrosion in the reaction.

Description

technical field [0001] The invention relates to a method for preparing organic carboxylate by olefin hydroesterification. Background technique [0002] Organic carboxylic acid esters are an important class of oxygen-containing compounds, which are widely used in fine chemical products, medicine, pesticides, food additives, spices, coatings, paints and other fields. Among the many carbonylation reactions that directly introduce carbonyl groups into the molecules of organic compounds to become oxygenated compounds, the hydroesterification reaction has always been a research hotspot. It is prepared in one step using simple raw materials (unsaturated compounds, carbon monoxide, alcohols) A convenient method for organic carboxylates. At present, the reported catalysts are mainly complexes formed by the coordination of central metal ions and related phosphine ligands. The central metal ions are transition metals of VIII and X subgroups, Rh, Pd, Ni, Co, Cu, etc. are used more, am...

Claims

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Application Information

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IPC IPC(8): C07C67/38C07C69/24C07C69/612B01J31/24
CPCY02P20/54
Inventor 夏春谷刘建华陈静
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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