Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fe-Fe hydrogenase model containing functionalized phosphine ligand and preparation method thereof

A technology of iron hydrogenase and phosphine ligand, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, iron organic compounds, etc., to achieve mild conditions, excellent catalytic hydrogen production capacity, and easy availability of raw materials Effect

Inactive Publication Date: 2017-05-10
NANKAI UNIV
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although hydrogen is a clean fuel with high combustion value and renewable, so far there is no efficient catalyst based on cheap metals, which can be used to industrially catalyze protons in water to produce hydrogen

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fe-Fe hydrogenase model containing functionalized phosphine ligand and preparation method thereof
  • Fe-Fe hydrogenase model containing functionalized phosphine ligand and preparation method thereof
  • Fe-Fe hydrogenase model containing functionalized phosphine ligand and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A method for preparing a model substance 1 of iron-iron hydrogenase containing a functionalized phosphine ligand, the chemical formula of the model substance 1 is [{(μ-SCH 2 ) 2 CH 2} Fe 2 (CO) 4 ][PhP(CH 2 Oh) 2 ] 2 , the preparation process is as follows:

[0023]

[0024] Concrete preparation steps are as follows:

[0025] 1) Under nitrogen protection, add 386 mg (1.0 mmol) [(μ-SCH 2 ) 2 CH 2 ] Fe 2 (CO) 6 and 30mL tetrahydrofuran to obtain a reddish-brown solution;

[0026] 2) At room temperature and under nitrogen protection, 408mg (2.4mmol) PhP(CH 2 Oh) 2 The thick substance was directly added dropwise into the reddish-brown solution, and heated to reflux for 30 hours to obtain a black-red solution, and the raw material point basically disappeared as monitored by TLC;

[0027] 3) Dry the solvent under reduced pressure, extract the residue with EtOAc, use petroleum ether / EtOAc=1:1 (v / v) as a developing solvent for thin-layer chromatography separat...

Embodiment 2

[0030] A preparation method of a model substance 2 of iron-iron hydrogenase containing a functionalized phosphine ligand, the chemical formula of the model substance 2 is [{(μ-SCH 2 ) 2 CHCH 2 OH}Fe 2 (CO) 5 ][PhP(CH 2 Oh) 2 ], the preparation process is as follows:

[0031]

[0032] Concrete preparation steps are as follows:

[0033] 1) Under nitrogen protection, add 374 mg (0.9 mmol) [(μ-SCH 2 ) 2 CHCH 2 OH]Fe 2 (CO) 6 and 15mL tetrahydrofuran to obtain a red solution;

[0034] 2) At room temperature and under nitrogen protection, 170mg (1.0mmol) PhP(CH 2 Oh) 2 The thick substance was directly added dropwise to the red solution, and stirred overnight at room temperature to obtain a reddish-brown solution. TLC monitoring showed that a new red spot appeared and a small amount of raw material red spots existed;

[0035] 3) Dry the solvent under reduced pressure, extract the residue with EtOAc, use petroleum ether / EtOAc=2:3 (v / v) as a developer for thin-layer ch...

Embodiment 3

[0038] A preparation method of a model substance 3 of iron-iron hydrogenase containing a functionalized phosphine ligand, the chemical formula of the model substance 3 is [{(μ-SCH 2 ) 2 CH 2} Fe 2 (CO) 5 ][PhP(CH 2 OH)(CH 2 CO 2 Me)], the preparation process is as follows:

[0039]

[0040] Concrete preparation steps are as follows:

[0041] 1) Under nitrogen protection, add 48mg (0.46mmol) CH 2 (CO 2 h) 2 , 68mg (0.56mmol) DMAP and 220mg (1.06mmol) DCC, put it in an ice-water bath down to 0 ° C, inject 20mL CH 2 Cl 2 ;

[0042] 2) After stirring at low temperature for 2 hours, add 243mg (0.46mmol) model substance [{(μ-SCH 2 ) 2 CH 2} Fe 2 (CO) 5 ][PhP(CH 2 Oh) 2 ], remove the ice-water bath and naturally rise to room temperature, continue to stir for 6h, and the TLC monitoring raw material point disappears substantially;

[0043] 3) dry the solvent under reduced pressure, use CH 2 Cl 2 Extract the residue with petroleum ether / CH 2 Cl 2 =2:3(v / v) was...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a Fe-Fe hydrogenase model containing a functionalized phosphine ligand. In the model, a [2Fe2S] catalytic center is connected to a hydrophilic group functionalized phosphine ligand, and the chemical structural formula is as follows: in the structural formula, R is hydrogen or hydroxymethyl (CH2OH), and L is bis(hydroxymethyl) phenylphosphine [PhP(CH2OH)2], hydroxymethyl / methyl acetate phenylphosphine [PhP(CH2OH)(CH2CO2Me)], and bis(methyl acetate) phenylphosphine PhP(CH2CO2Me)2] or (4-hydroxyphenyl)diphenylphosphine [Ph2P(C6H4OH-p)]. The model has the beneficial effects that the Fe-Fe hydrogenase model containing a functionalized phosphine ligand prepared by the method has easily available raw materials, mild conditions, and simple operation; the model is suitable for preparing the Fe-Fe hydrogenase model containing various kinds of functionalized phosphine ligands, and the model has latent excellent catalysis capability for producing hydrogen.

Description

technical field [0001] The invention belongs to the fields of organometallic, energy and material sciences, in particular to a class of iron-iron hydrogenase model substances containing functionalized phosphine ligands and a preparation method thereof. Background technique [0002] Solving energy shortage and environmental pollution is one of the major challenges facing human society today. Although hydrogen is a clean fuel with high combustion value and renewable, so far there is no efficient catalyst based on cheap metals, which can be used to catalyze protons in water to produce hydrogen on an industrial scale. Iron-iron hydrogenase is a metalloenzyme that exists in microorganisms and can efficiently catalyze the reduction of protons to hydrogen. In recent years, scientists have carried out extensive and in-depth research on the structure and function simulation of the active center of iron-iron hydrogenase, in order to synthesize an ideal "artificial enzyme" hydrogen pr...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F19/00B01J31/24
CPCB01J31/24C07F15/02
Inventor 宋礼成王咏祥赵培华
Owner NANKAI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com