CN108484686A - Ferronickel hydrogenation catalator object and preparation method of the one kind containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions - Google Patents
Ferronickel hydrogenation catalator object and preparation method of the one kind containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions Download PDFInfo
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- CN108484686A CN108484686A CN201810476935.5A CN201810476935A CN108484686A CN 108484686 A CN108484686 A CN 108484686A CN 201810476935 A CN201810476935 A CN 201810476935A CN 108484686 A CN108484686 A CN 108484686A
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- benzene
- diphenylphosphine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/62—Reductions in general of inorganic substrates, e.g. formal hydrogenation, e.g. of N2
Abstract
Ferronickel hydrogenation catalator object and preparation method thereof of the one kind containing 1,2 bis- (diphenylphosphine) benzene and different complex anions, [NiFe] the catalytic center cationic portion in the class model object contains there are two biphosphine ligand and with butterfly-shaped NiFeS2Unit, anion part are the different complex anions with negative one valence.Its chemical structural formula is as follows：
Description
Technical field
The invention belongs to metal is organic and energy science and technology field, it is especially a kind of containing bis- (diphenylphosphine) benzene of 1,2- with
Ferronickel hydrogenation catalator object of different complex anions and preparation method thereof.
Background technology
With human society and economic continuous development, these three fossil fuels of coal, oil and natural gas can not expire
Demand of the sufficient mankind to the energy, especially because long-term a large amount of uses of fossil fuel, have made a large amount of greenhouse gases CO2With can
Form the gas SO of acid rain2It is discharged among air, to cause serious environmental pollution.In recent years, in order to make green can
Regenerated Hydrogen Energy replaces fossil energy, scientist to carry out a large amount of biomimetic chemistry to the activated centre of natural [NiFe] hydrogenase
Research.Ferronickel hydrogenase is present in multiple-microorganism body, it can efficiently proton reduction be hydrogen and hydrogen in catalytic water
Heterolytic reaction.Referring to：Volbeda,A.；Garcin,E.；Piras,C.；de Lacey,A.L.；Fernandez,V.M.；
Hatchikian,E.C.；Frey,M.；Fontecilla-Camps,J.C.J.Am.Chem.Soc.1996,118,12989；
Tard, C.；Pickett,C.J.Chem.Rev.2009,109,2245；Simmons,T.R.；Berggren,G.；Bacchi,
M.；Fontecave,M.；Artero,V.Coord.Chem.Rev.2014,270–271,127；Schilter,D.；Camara,
J.M.；Huynh,M.T.；Hammes-Schiffer,S.；Rauchfuss,T.B.Chem.Rev.2016,116,8693；Ogo,
S.Coord.Chem.Rev.2017,334,43。
So far, scientist has carried out a large amount of biomimetic chemistry research to ferronickel hydrogenase activity division center, obtains
There is the model object similar with nickel-iron hydrogenase activity division center, department pattern object also to have cracking hydrogen well
Or Catalytic Proton is reduced to the function of hydrogen.Referring to：Ogo,S.；Ichikawa,K.；Kishima,T.；Matsumoto,T.；
Nakai, H.；Kusaka,K.；Ohhara,T.Science 2013,339,682；Manor,B.C.；Rauchfuss,
T.B.J.Am.Chem.Soc.,2013,135,11895；Song,L.-C.；Yang,X.-Y.；Cao,M.；Gao,X.-Y.；Liu,
B.-B.；Zhu,L.；Jiang,F.Chem.Commun.2017.53,3818；Song,L.-C.；Han,X.-F.；Chen,W.；
Li,J.-P.；Wang,X.-Y.Dalton Trans.2017,46,10003.
Invention content
The purpose of the present invention is analyzing in view of the above technology, a kind of bis- (hexichol containing 1,2- are provided by using " one kettle way "
Base phosphine) benzene and different complex anions ferronickel hydrogenation catalator object and preparation method thereof.[NiFe] catalysis in the class model object
Center cation part contains there are two biphosphine ligand and with butterfly-shaped NiFeS2Unit, anion part are with negative one valence
Different complex anions.Model object preparation process is easy to operate, raw material is cheap and easy to get, reaction condition is mild, yield is high, can prepare one
Ferronickel of the series containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object.This synthesized class model simultaneously
Object has the function of potentially producing hydrogen and activation hydrogen heterolytic fission.
Technical scheme of the present invention：
Ferronickel hydrogenation catalator object of the one kind containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions, in the class model object
[NiFe] catalytic center cationic portion contain that there are two biphosphine ligands and with butterfly-shaped NiFeS2Unit, anion part are
Different complex anions with negative one valence.Its chemical structural formula is as follows：
X is tetrafluoroborate, tetraphenylborate, hexafluoro-phosphate radical or perchlorate in structural formula, and R is carbonyl, cyanogen root
Or thiocyanate, n values are 1 or 2.
The preparation method of ferronickel hydrogenation catalator object of the one kind containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions, step
It is rapid as follows：
1) it replaces and is equipped in the reaction bulb of stirring magneton in nitrogen, by [(dppv) Fe (CO)2(pdt)] [dppv=is cis-
1,2- bis- (diphenylphosphoryl group) ethylene, pdt=1,3 dimercaptopropane salt] and (dppbe) NiCl2[bis- (the diphenyl of dppbe=1,2-
Phosphino-) benzene] it is added in organic solvent and is uniformly mixed, obtain mixed liquor；
2) sodium tetrafluoroborate, sodium tetraphenylborate, Potassium Hexafluorophosphate or sodium perchlorate are added in above-mentioned mixed liquor, reacts
2h obtains reaction solution；
3) by above-mentioned reaction solution decompressing and extracting, residue is extracted with dichloromethane, use dichloromethane-acetone mixed liquor as
Solvent carries out TLC separation, collects mass-tone band, and it is containing bis- (diphenylphosphine) benzene of 1,2- and not to obtain orange red color substance
Ferronickel with complex anion hydrogenates catalator object and its framework compound.
4) sodium tetrafluoroborate or into the mixed liquor of step 1) is added, reacts 2h, obtains reaction solution；
5) compound oxidation trimethylamine and tetrabutyl ammonium cyanide or thiocyanic acid are added in the step 4) reaction solution
Potassium, 0 DEG C of controlling reaction temperature react 1h；
6) by step 5) the reaction solution decompressing and extracting, thin-layer chromatography point is carried out as solvent using dichloromethane and acetone
From collection mass-tone band, it is the ferronickel hydrogen containing 1,2- bis- (diphenylphosphine) benzene and different complex anions to obtain Orange red solid substance
Change catalator object.
Organic solvent is acetone or dichloromethane, [(dppv) Fe (CO) in the step 1)2(pdt)], (dppbe) NiCl2
Amount ratio with organic solvent is 0.5mmol：0.5mmol：30mL.
Sodium tetrafluoroborate in the step 2), sodium tetraphenylborate, Potassium Hexafluorophosphate or sodium perchlorate and [(dppv) Fe
(CO)2(pdt)] amount ratio is respectively 0.5mmol：1-5mmol.
The volume ratio of dichloromethane and acetone is 1-20 in the step 3) solvent：1-3.
[(dppv) Fe (CO) in affiliated step 4)2(pdt)], (dppbe) NiCl2Amount ratio with sodium tetrafluoroborate is
0.5mmol：0.5mmol：5mmol.
Sodium tetrafluoroborate and the amount ratio of trimethylamine oxide, tetrabutyl ammonium cyanide or potassium rhodanide are in affiliated step 5)
5mmol：0.5mmol：0.5mmol.
The volume ratio of dichloromethane and acetone is 1 in the step 6) solvent：15.
The advantages of the present invention are:
Preparation process is simple for process, raw material is cheap and easy to get, reaction condition is mild, yield is high；It can by changing carbonyl ligands
Prepare a kind of novel ferronickel hydrogenase model object for containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions.
Specific implementation mode
To more fully understand the present invention, the scheme that will be further illustrated the present invention below by specific embodiment, but this
The protection domain of invention should include the full content of claim, without being limited thereto.
Embodiment 1：
Preparation method containing the ferronickel of bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenation catalator object 1, it is described
The chemical formula of model object 1 is [(dppv) Fe (CO)2(pdt)Ni(dppbe)(2BPh4)], preparation process is as follows：
Specific preparation process is as follows：
1) in the case where 0 DEG C of high pure nitrogen is protected, 307mg is added into dried Schlenk bottles of the 100mL with magneton
(0.5mmol) compound [(dppv) Fe (CO)2(pdt)], 288mg (0.5mmol) compound (dppbe) NiCl2And 342mg
(1mmol) compound N aBPh4, and 30mL dichloromethane is added, which reacts 2h；
2) by above-mentioned reaction solution decompressing and extracting solvent, residue is extracted with dichloromethane, is 20 with volume ratio:1 dichloro
Methane-acetone mixture carries out TLC separation as solvent, collects orange red mass-tone band, obtains red solid (model
Object 1) 791mg, chemical formula is [(dppv) Fe (CO)2(pdt)Ni(dppbe)(2BPh4)], yield 90%.
3) product structure data characterization is as follows：Anal.Calcd for C109H92B2FeNiO2P4S2:Theoretical value：C:
74.47,H:5.27. measured value：C:74.19,H:4.98.IR(KBr disk):νC≡O:2058(m),1994(s)cm-1.1H NMR
(400MHz,Acetone-d6):2.11-2.16,2.55-2.62(2m,6H,3CH2),6.75-7.81(m,84H,C6H4,
16C6H5), 8.52-8.68 (m, 2H, PCH=CHP) ppm.13C{1H}NMR(100MHz,Acetone-d6):30.72,33.28,
37.75(s,SCH2CH2CH2S),122.45-165.71(m,17C6H5), 150.44-151.09 (m, PCH=CHP), 207.65-
208.54(m,CO)ppm.31P{1H}NMR(161.9MHz,Acetone-d6):65.39(s,Fe-P),56.94(s,Ni-P)
ppm。
Embodiment 2：
Preparation method containing the ferronickel of bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenation catalator object 2, it is described
The chemical formula of model object 2 is [(dppv) Fe (CO)2(pdt)Ni(dppbe)(2BPh4)], preparation process is as follows：
Specific preparation process is substantially the same manner as Example 1, the difference is that：
920mg is changed in step 1), the compound K PF of (5mmol)6；
Dichloromethane-acetone mixed liquor is 1 as solvent ratio in step 2):3, obtain Orange red solid after processing
(model object 2) 530mg, chemical formula are [(dppv) Fe (CO)2(pdt)Ni(dppbe)(2PF6)], yield 75%.
Product structure data characterization is as follows：Anal.Calcd for C61H52F12FeNiO2P6S2:Theoretical value：C:51.98,
H:3.72. measured value：C:52.05,H:3.81.IR(KBr disk):νC≡O:2051(m),1989(m)cm-1.1H NMR
(400MHz,DMSO):2.18,2.65(m,3CH2),7.30-7.87(m,44H,C6H4,8C6H5),8.70-8.86(m,2H,PCH
=CHP) ppm.13C{1H}NMR(100MHz,DMSO-d6):30.65,32.11,36.25(s,SCH2CH2CH2S),125.24-
139.10(m,9C6H5), 149.52-152.29 (m, PCH=CHP), 206.42 (m, CO) ppm.31P{1H}NMR(161.9MHz,
Acetone-d6):65.35(s,Fe-P),56.91(s,Ni-P),-144.25(m,PF6)ppm。
Embodiment 3：
Preparation method containing the ferronickel of bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenation catalator object 3, it is described
The chemical formula of model object 3 is [(dppv) Fe (CO)2(pdt)Ni(dppbe)(2PF6)], preparation process is as follows：
Specific preparation process is substantially the same manner as Example 1, the difference is that：
610mg is changed in step 1), the compound N aClO of (5mmol)4,
Dichloromethane-acetone mixed liquor is 1 as solvent ratio in step 2):3, obtain Orange red solid after processing
(model object 3) 480mg, chemical formula are [(dppv) Fe (CO)2(pdt)Ni(dppbe)(2ClO4)], yield 73%.
Product structure data characterization is as follows：Anal.Calcd for C61H52Cl2FeNiO10P4S2:Theoretical value：C:55.97,
H:3.98. measured value：C:55.49,H:3.02.IR(KBr disk):νC≡O:2056(m),1991(vs)cm-1.1H NMR
(400MHz,Acetone-d6):2.01-2.57(m,6H,3CH2),7.17-7.75(m,44H,C6H4,8C6H5),8.58-8.73
(m, 2H, PCH=CHP) ppm.13C{1H}NMR(100MHz,Acetone-d6):30.7,32.136.3(s,SCH2CH2CH2S),
125.2-139.1(m,8C6H5,C6H4), 149.5-150.1 (m, PCH=CHP), 207.1 (s, CO) ppm.31P{H}NMR
(161.9MHz,Acetone-d6):65.21(s,Fe-P),56.89(s,Ni-P)ppm。
Embodiment 4：
Preparation method containing the ferronickel of bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenation catalator object 4, it is described
The chemical formula of model object 4 is [(dppv) Fe (CO) (CN) (pdt) Ni (dppbe) (BF4)], preparation process is as follows：
Specific preparation process is as follows：
1) in the case where 0 DEG C of high pure nitrogen is protected, 307mg is added into dried Schlenk bottles of the 100mL with magneton
(0.5mmol) compound [(dppv) Fe (CO)2(pdt)], 288mg (0.5mmol) compound (dppbe) NiCl2And 550mg
(5mmol) compound N aBF4, and 30mL dichloromethane is added, which reacts 2h, obtains mixed liquor；
2) trimethylamine oxide and 134mg (0.5mmol) of 37.5mg (0.5mmol) are added in above-mentioned mixed liquor
Bu4NCN continues to stir 1h, obtains reaction solution；
3) by above-mentioned reaction solution decompressing and extracting solvent, residue is extracted with dichloromethane, is 1 with volume ratio:15 dichloro
Methane-acetone mixture carries out TLC separation as solvent, collects orange red mass-tone band, obtains Orange red solid (mould
Type object 4) 410mg, chemical formula is [(dppv) Fe (CO) (CN) (pdt) Ni (dppbe) (BF4)], yield 68%.
Product structure data characterization is as follows：Anal.Calcd for C61H52BF4FeNNiOP4S2:Theoretical value：C:60.83,
H:4.35,N:1.16. measured value：C:60.59,H:4.54,N:1.07.IR(KBr disk):νCN:2085(vs)；νC≡O 1958
(vs)cm-1.1H NMR(400MHz,Acetone-d6):2.08-2.69(m,6H,3CH2),7.03-7.59,8.31(m,44H,
8C6H5,C6H4), 8.05-8.19 (m, 2H, HC=CH) ppm.13C{1H}NMR(100MHz,Acetone-d6):30.5,32.3,
37.8(s,SCH2CH2CH2S),128.9-136.8(8C6H5,C6H4), 141.7150.7 (m, HC=CH), 214.4 (s, CO)
ppm.31P{H}NMR(161.9MHz,Acetone-d6):76.70(s,Fe-P),51.86(s,Ni-P)ppm。
Embodiment 5：
Preparation method containing the ferronickel of bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenation catalator object 5, it is described
The chemical formula of model object 5 is [(dppv) Fe (CO) (NCS) (pdt) Ni (dppbe) (BF4)], preparation process is as follows：
Specific preparation process is substantially the same manner as Example 4, the difference is that：
It is changed to the compound K SCN of 48.5mg (0.5mmol) in step 2), Orange red solid (model object 5) is obtained after processing
390mg, chemical formula are [(dppv) Fe (CO) (SCN) (pdt) Ni (dppbe) (BF4)], yield 63%.
Product structure data characterization is as follows：Anal.Calcd for C61H52BF4FeNNiOP4S3:Theoretical value：C:59.25,
H:4.24,N:1.13. measured value：C:59.45,H:4.17,N:1.07.IR(KBr disk):νC≡O:2064(m)；νNCS:1951
(s)cm-1.1H NMR(400MHz,CDCl3):2.27-2.60(m,6H,3CH2),7.17-8.29(m,44H,8C6H5,C6H4),
8.38-8.52 (m, 2H, HC=CH) ppm.13C{1H}NMR(100MHz,CDCl3):29.7,30.1,37.0(s,
SCH2CH2CH2S),128.7-134.3(8C6H5,C6H4), 140.2-148.9 (m, HC=CH), 215.4 (s, CO) ppm.31P{H}
NMR(161.9MHz,Acetone-d6):73.62(s,Fe-P),51.86(s,Ni-P)ppm。
Claims (8)
1. ferronickel hydrogenation catalator object of the one kind containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions, in the class model object
[NiFe] catalytic center cationic portion contains there are two biphosphine ligand and with butterfly-shaped NiFeS2Unit, anion part are band
There are the different complex anions of negative one valence, chemical structural formula as follows：
X is tetrafluoroborate, tetraphenylborate, hexafluoro-phosphate radical or perchlorate in structural formula, and R is carbonyl, cyanogen root or sulphur
Cyanogen root, n values are 1 or 2.
2. the preparation method of ferronickel hydrogenation catalator object of the one kind containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions, step
It is as follows：
1) it replaces and is equipped in the reaction bulb of stirring magneton in nitrogen, by [(dppv) Fe (CO)2(pdt)] [the cis- 1,2- of dppv=
Bis- (diphenylphosphoryl group) ethylene, pdt=1,3 dimercaptopropane salt] and (dppbe) NiCl2[bis- (the diphenylphosphines of dppbe=1,2-
Base) benzene] it is added in organic solvent and is uniformly mixed, obtain mixed liquor；
2) sodium tetrafluoroborate, sodium tetraphenylborate, Potassium Hexafluorophosphate or sodium perchlorate are added in above-mentioned mixed liquor, reacts 2h,
Obtain reaction solution；
3) by above-mentioned reaction solution decompressing and extracting, residue is extracted with dichloromethane, uses dichloromethane-acetone mixed liquor as expansion
Agent carries out TLC separation, collects mass-tone band, and it is to contain bis- (diphenylphosphine) benzene of 1,2- and different networks to obtain orange red color substance
The ferronickel hydrogenation catalator object and its framework compound of anion；
4) sodium tetrafluoroborate or into the mixed liquor of step 1) is added, reacts 2h, obtains reaction solution；
5) compound oxidation trimethylamine and tetrabutyl ammonium cyanide or potassium rhodanide, control are added in the step 4) reaction solution
0 DEG C of reaction temperature processed reacts 1h；
6) by step 5) the reaction solution decompressing and extracting, TLC separation is carried out as solvent using dichloromethane and acetone, is received
Collect mass-tone band, it is the ferronickel hydrogenase mould containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions to obtain Orange red solid substance
Type object.
3. the ferronickel according to claim 2 containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object
Preparation method, which is characterized in that in the step 1) organic solvent be acetone or dichloromethane, [(dppv) Fe (CO)2
(pdt)], (dppbe) NiCl2Amount ratio with organic solvent is 0.5mmol：0.5mmol：30mL.
4. the ferronickel according to claim 2 containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object
Preparation method, which is characterized in that sodium tetrafluoroborate in the step 2), sodium tetraphenylborate, Potassium Hexafluorophosphate or perchloric acid
Sodium and [(dppv) Fe (CO)2(pdt)] amount ratio is respectively 0.5mmol：1-5mmol.
5. the ferronickel according to claim 2 containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object
Preparation method, which is characterized in that in the step 3) solvent volume ratio of dichloromethane and acetone be 1-20：1-3.
6. the ferronickel according to claim 2 containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object
Preparation method, which is characterized in that [(dppv) Fe (CO) in the step 4)2(pdt)], (dppbe) NiCl2With tetrafluoro boric acid
The amount ratio of sodium is 0.5mmol：0.5mmol：5mmol.
7. the ferronickel according to claim 2 containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object
Preparation method, which is characterized in that sodium tetrafluoroborate and trimethylamine oxide, tetrabutyl ammonium cyanide or thiocyanic acid in the step 5)
The amount ratio of potassium is 5mmol：0.5mmol：0.5mmol..
8. the ferronickel according to claim 2 containing bis- (diphenylphosphine) benzene of 1,2- and different complex anions hydrogenates catalator object
Preparation method, which is characterized in that in the step 6) solvent volume ratio of dichloromethane and acetone be 1：15.
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|---|---|---|---|---|
| CN110508325A (en) * | 2019-09-09 | 2019-11-29 | 鲁东大学 | Ferronickel hydrogenates catalator object, ionic ferronickel hydrogenation catalator object and preparation method and application |
| CN110508325B (en) * | 2019-09-09 | 2022-04-05 | 鲁东大学 | Ferronickel hydrogenase model substance, ionic ferronickel hydrogenase model substance, preparation method and application |
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