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Process for reaction of CO2 on heterocyclic compound under co-catalysis of transistion metal complex and organic alkali

A transition metal and compound technology, applied in the field of cyclic carbonate or oxazolidinone compound synthesis, can solve the problem of less three-membered nitrogen heterocyclic compounds, and achieve the effects of protecting the ecological environment, mild conditions and low energy consumption

Inactive Publication Date: 2002-09-18
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, three-membered nitrogen heterocycles and CO 2 The reaction of the reaction is rarely studied, and most of the obtained polymers

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthesis of embodiment 1 propylene carbonate

[0031] 2.6 g (4.5×10 -2 mol) propylene oxide, 5mL solvent, metal complex 125mg (4.5×10 -5 mol), and organic base 4-(N,N-dimethyl)-pyridine 11mg (9.0×10 -5 mol) was added to the reactor, and CO 2 The gas was replaced three times, and then the CO 2 up to 1.01×10 6 Pa, placed in an oil bath and heated to 100 ° C, after 16 hours of reaction. Take out the autoclave and place it in ice water to cool to room temperature. Open the autoclave to vent the gas. The rest was transferred to a round-bottomed flask, spin-dried on a rotary evaporator, and passed through a column. 4.13 g of colorless liquid was obtained, and the yield was 90%. IR (CHCl 3 )v1798(C=O)cm -1 ; 1 H NMR (CDCl 3 , TMS, 300MHz) δ1.51 (3H, d, J=6.11Hz), 4.02-4.07 (1H, m), 4.57 (1H, m), 4.57 (1H, t, J=8.55, 6.11Hz), 4.84 -4.91(1H, m); calculated value C 4 h 4 o 3 : C, 40.92; H, 4.58%, Found:: C, 40.90, H, 4.51%.

[0032] Thi...

Embodiment 2

[0033] The synthesis of embodiment 2 ethylene carbonates

[0034] According to the same steps as in Example 1, the R 1 , R 2 , R 3 The propylene oxide compound of =H, main catalyst is metal complex 13, and cocatalyst is DBU (1,8-diazacyclo[4.3.0]-5-nonene), DMAP (4-(N, N-dimethyl)-pyridine), triethylamine or DABCO (1,4-diazacyclo[2.2.2]octane) was reacted to give a colorless liquid, 3.60 g, 92%. IR (CHCl 3 )v1798(C=O)cm -1 ; 1 H NMR (CDCl 3 , TMS, 300MHz) δ4.51 (4H, s, CH 2 ); computed value C 3 h 4 o 3 : C, 47.06; H, 5.92%. Found: C, 47.12, H, 5.89%.

Embodiment 3

[0035] Example 3 Synthesis of 4-pentyl-[1,3]dioxolan-2-one

[0036] According to the same steps as in Example 1, the R 1 =(CH 3 ) 4 CH 3 , R 2 = H, R 3 The propylene oxide compound of =H, main catalyst is metal complex 13, and cocatalyst is DBU (1,8-diazacyclo[4.3.0]-5-nonene), DMAP (4-(N, N-dimethyl)-pyridine), triethylamine or DABCO (1,4-diazacyclo[2.2.2]octane) was reacted to obtain a colorless liquid, 6.4g, 90%. IR (CHCl 3 )v1799(C=O)cm -1 ; 1 H NMR (CDCl 3 , TMS, 300MHz) δ0.70-1.98 (11H, m), 3.89-4.19 (1H, m), 4.35-4.90 (2H, m); calculated value C 8 h 14 o 3 : C, 60.74; H, 8.92%. Found: C, 60.82, H, 8.91%.

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Abstract

A process for preparing annular carbonate or oxazolidinone compound features that reaction of epoxy propane compound or ternary acacyclic compound on CO2 under the co-catalysis of dinaphthylamine-transition metal complex and organic alkali to generate said product, which can be used to prepare amidocarbonate and its unsaturated derivatives, used as furnace, dihydrofuranone, etc. Its advantages are high output rate, less consumption of catalyst, and no poison and pollution.

Description

technical field [0001] The present invention relates to a new synthetic method of cyclic carbonate or oxazolidinone compound, further said to be composed of propylene oxide compound or ternary nitrogen heterocyclic compound and CO 2 The method for producing cyclic carbonate or oxazolidinone compounds through the reaction under the synergistic catalysis of the main catalyst binaphthylamine transition metal complex and the cocatalyst organic base. technical background [0002] Cyclic carbonate or oxazolidinone compounds can be used in medicine, pesticide and veterinary medicine in industry. Propylene carbonate can be used as a solvent. Its polymers can be used in fabrics, sugar-coated tablets for tablets, lubricant additives, rust inhibitors, foaming agents, softeners, dyeing aids, fabric waterproofing agents, etc. [0003] Cyclic carbonates or oxazolidinones are traditionally formed by the reaction of phosgene and alcohols or the condensation of phosgene or ethyl chloroform...

Claims

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Application Information

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IPC IPC(8): C07D263/06C07D317/34C07D317/36
Inventor 沈玉梅段伟良施敏
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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