Acidic room-temperature ionic liquid using acidic functional tetraalkylguanidine as cations and preparation method thereof

A technology of room temperature ionic liquid and tetraalkylguanidine, which is applied in the field of acidic room temperature ionic liquid and its preparation, can solve the problems of easy coke deactivation, poor thermal stability, environmental pollution, etc., and achieves environmental protection, easy separation, no Effects of by-products

Inactive Publication Date: 2011-05-04
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

[0003] In traditional acid-catalyzed reactions, commonly used catalysts include liquid inorganic acids and solid acids, which have equipment corrosion and environmental pollution. Solid acid catalysts are prone to carbon deposition and deactivation, poor thermal stability, and easy to scale.

Method used

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  • Acidic room-temperature ionic liquid using acidic functional tetraalkylguanidine as cations and preparation method thereof
  • Acidic room-temperature ionic liquid using acidic functional tetraalkylguanidine as cations and preparation method thereof
  • Acidic room-temperature ionic liquid using acidic functional tetraalkylguanidine as cations and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: 1,1,3, the synthesis of 3-tetramethyl-2-propanesulfonate guanidine bisulfate ion liquid

[0035] A, preparation 1,1,3,3-tetramethyl-2-propanesulfonate root guanidinium salt

[0036] 1,1,3,3-Tetramethylguanidine (0.3mol) and 1,3-propane sultone (0.3mol) were stirred and reacted for 4 hours at 80-85°C in toluene, and the resulting white solid was washed with toluene After washing three times and vacuum drying, 1,1,3,3-tetramethyl-2-propanesulfonate guanidinium salt was obtained with a yield of 99.7%.

[0037] B. Preparation of 1,1,3,3-tetramethyl-2-propanesulfonate guanidine bisulfate ionic liquid

[0038] 1,1,3,3-Tetramethyl-2-propanesulfonate guanidinium salt (0.1mol) and concentrated sulfuric acid (0.11mol) in toluene, stirred and reacted at 80°C for 4 hours, the reaction solution was divided into upper and lower layers , remove the toluene of the upper layer and unreacted raw materials, wash the lower layer with toluene, and vacuum-dry for 24 hours to ...

Embodiment 2

[0039] Example 2: Synthesis of 1,1,3,3-tetramethyl-2-propanesulfonate guanidine dihydrogen phosphate ionic liquid

[0040] 1,1,3,3-tetramethyl-2-propanesulfonate guanidinium salt (0.1mol) prepared according to Example 1 and 85% phosphoric acid (0.11mol) were in toluene, stirred and reacted for 4 hours at 80°C , the reaction solution is divided into upper and lower layers, remove the toluene and unreacted raw materials in the upper layer, wash the lower layer with toluene, and dry in vacuum for 24 hours to obtain 1,1,3,3-tetramethyl-2-propanesulfonic acid guanidine Dihydrogen phosphate ionic liquid, yield 90.4%, light brown viscous liquid at room temperature.

Embodiment 3

[0041] Example 3: Synthesis of 1,1,3,3-tetramethyl-2-propanesulfonate guanidine nitrate ionic liquid

[0042] 1,1,3,3-tetramethyl-2-propanesulfonate guanidinium salt (0.1mol) prepared according to Example 1 and 65% concentrated nitric acid (0.11mol) in toluene, stirring reaction at 80°C 4 hours, the reaction solution was divided into upper and lower layers, the upper layer of toluene and unreacted raw materials were removed, the lower layer was washed with toluene, and vacuum-dried for 24 hours to obtain 1,1,3,3-tetramethyl-2-propanesulfonic acid Guanidine nitrate ionic liquid, yield 98.2%, light brown viscous liquid at room temperature.

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Abstract

The invention discloses an acidic room-temperature ionic liquid using acidic functional tetraalkylguanidine as cations and a preparation method thereof. The structural formula of the ionic liquid is expressed as Formula (I), wherein R1=R2=CH3, R3=R4=CH3, n-C4H9, -(CH2)4- or -(CH2)5-, and n is 3 or 4; and X<-> stands for the anion group of the ionic liquid, and is selected from one of HSO4<->, H2PO4<->, NO3<->, Cl<->, BF4<->, PF6<->, CF3SO3<->, CH3SO3<->, CH3COO<->, CF3COO<->, C6H4COO<->, C6H4CH2COO<->, CH3(C6H4)SO3<-> and N(CF3SO2)2<->. The preparation method comprises the following steps: stirring tetraalkylguanidine sulfonate, which is used as the raw material, with acid to react at 80-85 DEG C in the medium (phenylmethane), and removing phenylmethane and the unreacted raw material to obtain the ionic liquid. The ionic liquid can be used for acid catalytic reactions of esterification, aldol condensation, etherification, alkylation and the like instead of the traditional acid catalyst.

Description

technical field [0001] The invention relates to an acidic room-temperature ionic liquid using acid-functionalized tetraalkylguanidine as a cation and a preparation method thereof. The ionic liquid can be used in esterification, aldol condensation, etherification and alkylation reactions. Background technique [0002] Room temperature ionic liquids refer to salt compounds composed of organic cations and inorganic or organic anions that are liquid at room temperature or near room temperature, and their physical and chemical properties can be adjusted by changing the structure and type of anions and cations. Introduce specific functional groups on the cation or anion of ionic liquid, can obtain functionalized ionic liquid (J.Mole.Catal.A: Chem., 2002,182-183,419; Chem.Lett., 2004,33,1072; Coor. Chem. Rev., 2004, 248, 2459). At present, functionalized ionic liquids have become a research hotspot, and are widely used in organic synthesis and catalytic reactions mainly as green r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/15C07C303/02C07C309/30C07C303/32C07D295/215B01J31/02B01J31/04C07C67/08C07C41/56C07C41/09C07C37/16C07C69/14C07C69/78C07C43/30C07C43/303C07C43/04C07C39/06
Inventor 夏春谷李臻刘佳梅陈静唐中华
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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