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Method for preparation of cyclic myrac aldehydes from myrac aldehyde catalyzed by zinc-containing ionic liquid

A technology of ionic liquids and zinc ions, which is applied in the field of zinc-containing ionic liquids to catalyze the conversion of citrus green aldehydes to prepare ring citrus green aldehydes, can solve problems such as environmental pollution, harsh reaction conditions, and waste acid production, and achieve high atom economy, The effect of fast response and mild conditions

Active Publication Date: 2019-04-19
DALIAN 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

The traditional production process of citrus cyanal uses protonic acids such as sulfuric acid, phosphoric acid, p-toluenesulfonic acid, Amberlite H + etc. are catalysts (Bull.Chem.Soc.Chim.Fr.1959,601-606; EP 0743297, priority 16.5.1995to Givaudan [Chem.Abstr.126,103856h]), using a large amount of volatile organic solvents, there is a catalyst dosage Disadvantages such as large size, easy to produce waste acid, relatively harsh reaction conditions, difficult separation of products, serious environmental pollution and non-reusable catalysts

Method used

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  • Method for preparation of cyclic myrac aldehydes from myrac aldehyde catalyzed by zinc-containing ionic liquid
  • Method for preparation of cyclic myrac aldehydes from myrac aldehyde catalyzed by zinc-containing ionic liquid
  • Method for preparation of cyclic myrac aldehydes from myrac aldehyde catalyzed by zinc-containing ionic liquid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of ionic liquid catalyst: refer to literature (Li C, Zhao Z.Adv.Synth.Catal.2007, 349,1847; Webb P B, Sellin M F, Kunen T E, et al.J.Am.Chem.Soc.2003,125 , 15577; NodaA, Watanabe M.Electrochimica Acta.2000,45,1265; Sheldrake G N, Schleck D.GreenChem.2007,9,1044.) and patent (WO 00 / 16902) prepared and purified nine Lewis ionic liquids, Respectively: 1-methyl-3-butylimidazole-zinc chloride [C 4 mim]Zn 2 Cl 5 , 1-methyl-3-ethylimidazole-zinc chloride [C 2 mim]Zn 2 Cl 5 , 1-ethyl-3-butylimidazole-zinc chloride [C 4 C 2 im]Zn 2 Cl 5 , 1-ethyl-3-ethylimidazole-zinc chloride [C 2 C 2 im]Zn 2 Cl 5 , 1-butyl-3-butylimidazole-zinc chloride [C 4 C 4 im]Zn 2 Cl 5 , 1-butyl-3-ethylimidazole-zinc chloride [C 2 C 4 mim]Zn 2 Cl 5 , picoline-zinc chloride [MPy]Zn 2 Cl 5 , ethylpyridine-zinc chloride [C 2 Py]Zn 2 Cl 5 , butylpyridine-zinc chloride [C 4 Py]Zn 2 Cl5 , for the implementation of the patent of the present invention.

Embodiment 2-13

[0024] [C 4 mim]Zn 2 Cl 5 Catalytic selective cyclization of para-citrus aldehyde to prepare citrus aldehyde: 10 g of the reaction substrate and a certain mass of [C 4 mim]Zn 2 Cl 5 Catalysts were added to the reactor respectively, sealed and replaced with nitrogen five times, the initial pressure of nitrogen was 0.1MPa, the temperature was raised to 100-200°C, and the stirring reaction was carried out at a speed of 1000 rpm for 1-10h. After the reaction was completed, it was cooled to room temperature, and the reaction mixture was separated into two layers. The supernatant was poured and then sampled for analysis. The remaining ionic liquid catalyst in the lower layer was washed three times with n-hexane and directly used for the next reaction (see Examples 14-18). Qualitative analysis of the product was carried out by GC-MS technology and standard sample control, and quantitative analysis was realized by gas chromatography internal standard method. The reaction result...

Embodiment 14-18

[0028] [C 4 mim]Zn 2 Cl 5 The repeated use experiment results of catalyzing the selective cyclization of p-citrus aldehyde to prepare cyclocitrus green agent: 10g of p-citrus aldehyde and 1g of [C 4 mim]Zn 2 Cl 5 Catalysts were added to the reactor respectively, sealed and replaced with nitrogen five times, and the initial pressure of nitrogen was 0.1 MPa, the temperature was raised to 150°C, and the stirring reaction was carried out at a speed of 1000 rpm for 4 hours. After the reaction was completed, it was cooled to room temperature, and the reaction mixture was separated into two layers. The supernatant was poured and then sampled for analysis. The remaining ionic liquid catalyst in the lower layer was washed three times with n-hexane and directly used for the next reaction, and was reused five times. Qualitative analysis of the product was carried out by GC-MS technology and standard sample control, and quantitative analysis was realized by gas chromatography intern...

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Abstract

The invention provides a novel method for catalyzing cyclization reaction of myrac aldehyde for conversion to cyclic myrac aldehydes by using a Lewis acidic ionic liquid as a catalyst. According to the method, by using a zinc-containing ionic liquid as a catalyst and under the mild condition, 4-(4-methyl-3-pentenyl)-3-cyclohexenal(p-myrac aldehyde) and 3-(4-methyl-3-pentenyl)-3-cyclohexenal (m-myrac aldehyde) undergo selective cyclization to prepare cyclic myrac aldehydes (1,2,3,4,5,6,7,8-octahydro-,8,8-dimethyl-2-naphthaldehyde and 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2-naphthaldehyde). Incomparison with a traditional cyclic myrac aldehydes production method, the invention has the following distinctive characteristics: the use of a volatile organic solvent is avoided in the reaction; the reaction condition is mild; the target product has high selectivity, and the reaction is rapid; after the reaction, the ionic liquid catalyst and the product are automatically layered and are convenient to separate; the ionic liquid catalyst is recyclable; generation of a waste acid solution by traditional catalysis is avoided; and the method is environmentally friendly.

Description

technical field [0001] The invention provides a new method for catalyzing the cyclization reaction of citrus aldehydes with zinc-containing ionic liquids to convert citrus aldehydes. Specifically, the Lewis acidic ionic liquid generated by the reaction of short-chain dialkylimidazolium chloride or alkylpyridine chloride with 2 mol equivalents of zinc chloride is used as a catalyst, and 4-(4 -Methyl-3-pentenyl)-3-cyclohexenal (para-citrual) and 3-(4-methyl-3-pentenyl)-3-cyclohexenal (meta-citrual Green aldehydes) selective cyclization to prepare ring citrus green aldehydes (1,2,3,4,5,6,7,8-octahydro-,8,8-dimethyl-2-naphthaldehyde and 1,2,3 ,4,5,6,7,8-octahydro-5,5-dimethyl-2-naphthaldehyde). Background technique [0002] The aroma of food and cosmetics is the feeling caused by the particles of volatile substances suspended in the air, stimulating the olfactory nerve through the nostrils, and then transmitted to the brain. With the development of the flavor and fragrance in...

Claims

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Application Information

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IPC IPC(8): C07C45/67C07C47/445
CPCC07C45/67C07C47/445Y02P20/584
Inventor 李昌志代弢季建伟王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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