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Process for synthesizing annular carbonate or oxazolidinone compounds

A phenolic compound and compound technology, which is applied in the field of cyclic carbonate or oxazolidinone compound synthesis, can solve the problem of less three-membered nitrogen heterocyclic compounds, protect the ecological environment, reduce energy consumption, and meet the The effect of continuous development

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 heterocyclic compounds and CO 2 The reaction of the reaction is rarely studied, and most of the obtained polymers
Propylene oxide compounds and three-membered nitrogen heterocyclic compounds and CO 2 The reaction under the synergistic catalysis of phenolic compound or Schiff base and organic base has never been reported.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of embodiment 1 propylene carbonate

[0032] 2.6g (4.5×10 -2 mol) propylene oxide, 5mL solvent, phenol 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%.

Embodiment 2

[0033] The synthesis of embodiment 2 ethylene carbonates

[0034] According to the same steps as in Example 1, R in epoxy compounds 1 = H, R 2 = H, R 3 =H, the main catalyst is m-nitrophenol, and the promoter 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) to obtain 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, R in epoxy compounds 1 =(CH 2 ) 4 CH 3 , R 2 = H, R 3 =H, the main catalyst can be p-methoxyphenol, and the procatalyst 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), 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 rC 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 synthesizing annular carbonate or oxazolidione compound features that reaction of epoxy propane compounds or ternary acacyclic compounds on CO2 under the co-catalysis of phenol compound, schiff base and organic alkali to generate said product which can be used to prepare amidocarbonate and its unsaturated derivatives. Its advantages are cyclnc use of catalyst, high efficiency, 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 A method for producing cyclic carbonates or oxazolidinone compounds through the reaction under the synergistic catalysis of the main catalyst phenolic compound or Schiff base and the co-catalyst organic base. technical background [0002] Cyclic carbonate or oxazolidinone compounds can be used in medicine, pesticide and veterinary medicine in industry. Carbonates can be used as solvents. Its polymers are 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 chloroformate, dialkyl carbonat...

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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