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Salen-Fe-like complex, and preparation method and application thereof

A kind of complex and type of technology, applied in the direction of iron-group organic compounds without C-metal bonds, organic compound/hydride/coordination complex catalysts, iron-organic compounds, etc., can solve the problem of cost increase, harsh reaction conditions, step cumbersome and other problems, to achieve the effect of convenient operation, easy control of conditions, and good selectivity

Inactive Publication Date: 2015-04-29
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a catalyst for the coupling reaction of carbon disulfide and epoxycyclohexane, specifically a Salen-Fe complex, which is based on the Salen metal complex with one of the carbon nitrogen bis The bond becomes a carbon-sulfur single bond, making it a metal complex with an asymmetric center. The preparation method is firstly to use cysteine ​​hydrochloride, 3,5-di-tert-butyl salicylaldehyde and 2,4- Raw materials such as di-tert-butylphenol are synthesized into a novel Salen-like ligand through a two-step method, and then the ligand is used to react with anhydrous ferric chloride to generate a Salen-Fe complex. This catalyst is easy to prepare and has a simple process. Good controllability and environmental friendliness, inheriting the advantages of asymmetric Salen metal complexes in catalytic activity and selectivity, and overcoming the disadvantages of cumbersome steps, increased cost, and harsh reaction conditions in the synthesis of asymmetric Salen metal complexes

Method used

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  • Salen-Fe-like complex, and preparation method and application thereof
  • Salen-Fe-like complex, and preparation method and application thereof
  • Salen-Fe-like complex, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] In the first step, put 0.1mol 2,4-di-tert-butylphenol in a three-necked round-bottomed flask, dissolve in anhydrous methanol (the amount of methanol should be dissolved), add 0.15mol sodium hydroxide, stir at room temperature for 30min, then add 25ml Formaldehyde solution (concentration: 37%-40% (mass fraction)), after adding, stir at room temperature for 26 hours. Pour the resulting light yellow reaction solution into a beaker filled with 250ml of distilled water, the solution becomes turbid and large yellow particles are formed, and the pH is adjusted to between 2 and 3 with concentrated hydrochloric acid (concentration is 37.5%). Extracted with dichloromethane, combined and washed with saturated brine, a small amount several times to obtain a light yellow clear solution. Dry with anhydrous sodium sulfate, filter with suction, and rotary evaporate to obtain a light yellow solid. Recrystallized with petroleum ether and dried to obtain white needle-like crystals, namel...

Embodiment 2

[0036] Take by weighing the class Salen ligand 0.5mmol Lig that obtains in the example 1 1 h 2 Put it in a branch bottle, pump it with argon three times, and under the protection of argon, add dichloromethane to dissolve it, then add dropwise a methanol solution containing 1mmol anhydrous ferric chloride and 1.5mmol anhydrous sodium acetate, Stir at room temperature for 24 hours to obtain a black liquid, which was rotary evaporated, extracted with dichloromethane, washed with saturated brine, and the organic layer was dried with anhydrous sodium sulfate, left to stand for suction filtration, rotary evaporated, and dried in a vacuum oven to obtain a black metallic Shiny Salen-Fe-like complex Cat1 in 63% yield. Infrared (υin cm -1 ): 2959, 1610, 1539, 1458, 1385, 1255, 1180, 1096, 878, 803, 669, 551, 484. Elemental analysis: C 63.90% (63.94%), H 7.92%, (7.88%), O 5.24% (5.32%), N 2.27% (2.34%), S 5.28 (5.33%), Cl 5.83% (5.90%) . The UV spectrum of the complex Cat1 is attach...

Embodiment 3

[0038] Put 0.5 μmol of bistriphenylphosphine ammonium chloride (PPNCl) into a three-necked round-bottomed flask, pump three times with argon, and then add 0.0125mol of carbon disulfide and 0.025mol of epoxy cyclohexane in sequence, that is, carbon disulfide and epoxy ring The molar ratio of hexane is 1:2. React for 4 hours at 120°C, pour the resulting reaction liquid into a beaker filled with methanol to obtain a precipitate, filter with suction to obtain a precipitate, wash with methanol, and dry in vacuo to obtain 0.13 g of the product . 1 HNMR: (400MHz, CDCl 3 ,δin ppm): 1.43~1.52(m,2H,CH 2 ),1.67~1.77(m,2H,CH 2 ),1.91~2.00(m,2H,CH 2 ),2.20~2.23(m,2H,CH 2 )), 4.05 ~ 4.13 (m, H, CHS), the product's infrared spectrum, nuclear magnetic hydrogen spectrum, nuclear magnetic carbon spectrum, respectively see attached Figure 4 , 5 , 6, these characterizations indicated that the product was a cyclic trithiocarbonate.

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Abstract

The invention relates to a Salen-Fe-like complex, and a preparation method and application thereof. The structure of the complex is disclosed in the specification. The preparation method comprises the following steps: carrying out a two-step process on cysteine hydrochloride, 3,5-di-tert-butyl salicylaldehyde, 2,4-di-tert-butyl phenol and the like to synthesize a novel Salen-like ligand, and reacting the ligand with anhydrous ferric chloride to generate the Salen-Fe-like complex. The complex and bis triphenylphosphine ammonium chloride can be used as a catalyst to successfully generate cyclic trithiocarbonate; and the conversion rate of carbon bisulfide can reach 100%, the yield is 60%, and the catalytic efficiency is 9980 mol cyclic trithiocarbonate / mol catalyst.

Description

technical field [0001] The invention relates to the reaction of carbon disulfide and epoxycyclohexane, in particular to a Salen-Fe complex and its preparation method and application. technical background [0002] Carbon disulfide (CS 2 ) is a toxic organosulfur compound, widely present in natural gas, coke oven, coal gas, water gas, refinery gas and Claus tail gas, and a small amount of carbon disulfide in the chemical fiber industry. due to CS 2 It is highly toxic, highly volatile, and has a low boiling point. It is easily emitted into the air during production and use, causing serious pollution and harm to the environment and the human body. Continuously emitted carbon disulfide is easily oxidized to sulfur dioxide in the stratosphere, causing acid rain. Due to the harm of carbon disulfide to the environment, scientists have been exploring ways to utilize carbon disulfide. [0003] Cyclic trithiocarbonates can be used as pesticide intermediates due to their biological ...

Claims

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Application Information

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IPC IPC(8): C07F15/02B01J31/22B01J31/24C07D339/06
CPCB01J31/2217B01J31/24B01J2531/0252C07D339/06C07F15/025
Inventor 段中余温洁
Owner HEBEI UNIV OF TECH
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