CN104324751B - A kind of catalyst for hydrosilylation of olefins, its preparation method and use the hydrosilylation of olefins of this catalyst - Google Patents
A kind of catalyst for hydrosilylation of olefins, its preparation method and use the hydrosilylation of olefins of this catalyst Download PDFInfo
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Abstract
The present invention relates to organic chemistry filed, be specifically related to a kind of catalyst for hydrosilylation of olefins, its preparation method and use the hydrosilylation of olefins of this catalyst.This catalyst is, after the double N heterocycle carbine platinum complexes containing polyether segment are cyclized by dibasic carboxylic acid slaine, to be prepared from.The catalyst of preparation has preferable selectivity and activity, good stability, and is easily isolated, and the repeatable utilization rate of catalyst is high.
Description
Technical field
The present invention relates to organic chemistry filed, be specifically related to a kind of catalyst for hydrosilylation of olefins, its preparation method
And use the hydrosilylation of olefins of this catalyst.
Background technology
The hydrosilylation of catalysis unsaturated compound and silane containing hydrogen is the important topic (J. of organosilicon chemistry and industry
Organomet.Chem., 2003,681,91-97), the most important thing in this problem is then the research and development of effective catalyst.Alkene
Hydrosilylation is synthesizing organo-silicon coupling agent and one of function organo-silicon compound and the most important approach of polymer, for alkene
Hydrocarbon Si-H addition reaction, industry and laboratory generally use Speier catalyst (aqueous isopropanol of chloroplatinic acid) and Karstedt at present
Catalyst (the tetramethyl divinyl disiloxane coordination compound of platinum), according to using condition and suitable substrates, auxiliary agent to be added,
To improve above-mentioned two class catalyst system and catalyzing catalysis activity and selectivitys.Mark ó etc. report, for Karstedt catalyst, utilize N-
Heterocycle carbine replaces its part tetramethyl divinyl disiloxane as part, and obtained N-heterocycle carbine platinum complex is to alkene
Si-H addition reaction has a high activity, simultaneously in course of reaction, catalyst system stabiliser, do not produce platinum black precipitation (Science, 2002,
298,204).It addition, research shows, carboxylic acid function's polyethylene glycol improves platinum catalysis hydrosilylation of olefins activity and selects
Property (Appl.Organomet.Chem., 2011,25,400-405).
And for catalyst for addition reaction of hydrogen and silicon and current catalyst that existing market solves the problems referred to above the most accordingly is universal
Shortcomings.
Summary of the invention
The invention aims to overcome problem described above, it is provided that a kind of catalyst for hydrosilylation of olefins,
Its preparation method and use the hydrosilylation of olefins of this catalyst
In order to reach foregoing invention purpose, the present invention by the following technical solutions:
A kind of catalyst for hydrosilylation of olefins, described catalyst is that dibasic carboxylic acid slaine is cyclized polyethers-N-heterocycle card
Guest's platinum complex, the structural formula of described catalyst is:
In structural formula:
M (L)=
M (1) is bivalent metal ion；
M=1 or 2 or 3；
N=4 or 6 or 8 or 12.
As preferably, described catalyst is that the double N-heterocycle carbine platinum complexes containing polyether segment are cyclized by dibasic carboxylic acid slaine
After, it is prepared from.
As preferably, the metal in carboxylic metallic salt in described catalyst is ferrum, zinc, calcium or magnesium, described bivalent metal ion
For Fe (II), Zn (II), Ca (II) or Mg (II).
The preparation method of a kind of catalyst for hydrosilylation of olefins, comprises the following steps:
(1) with the Polyethylene Glycol that mean molecule quantity is 200,300,400,600, it is raw material with thionyl chloride and imidazoles respectively,
Preparing tetra-kinds of end group imidazoles Polyethylene Glycol of A, B, C, D (that is: end position is imidazole radicals Polyethylene Glycol), structural formula is:
Tetra-kinds of end group imidazoles Polyethylene Glycol of described A, B, C, D, the n=4 in A, the n=6 in B, the n=8 in C, D
In n=12；
(2) by above-mentioned prepared four kinds of end groups imidazoles Polyethylene Glycol A, B, C, D respectively with 1-chlorinated carboxylic acid according to mol ratio
1:2 joins in the reaction vessel with magnetic agitation, heater and condensing unit, and makees reaction dissolvent with trichloroethane,
At 60-90 DEG C, stirring reaction 12h；
(3) the mixture cooling then above-mentioned reaction obtained, cleans twice by ethyl acetate after going the supernatant, decompression again
Remove residual solvent, be carboxylic acid functional imidazole salts, stand-by；
(4) above-mentioned prepared carboxylic acid functional imidazole salts is dissolved in dehydrated alcohol, according to carboxylic acid functional imidazole salts and metal alcoxyl
The mol ratio of based compound is the ratio of 1:1, adds ferrous iron, copper, zinc, calcium or the alkoxide compound of magnesium, at 40-60 DEG C,
Stirring reaction 3h, then removal of solvent under reduced pressure, obtain solid product；
(5) above-mentioned gained solid product is suspended in anhydrous tetrahydro furan, under room temperature, adds tert-butyl group potassium alcoholate, stir 30 points
Clock, is subsequently adding karstedt catalyst stirring 1h, removes solvent, obtain the catalyst for hydrosilylation of olefins.
The addition of tert-butyl group potassium alcoholate and imidazole radicals equivalent.Calculate according to reaction.
As preferably, in karstedt catalyst, the mol ratio of platinum and alkyl imidazole is 1:1.
A kind of hydrosilylation of olefins using above-mentioned a kind of catalyst for hydrosilylation of olefins, with catalyst,
Alkene and silane containing hydrogen mol ratio are (0.1-0.2): 1:(1-1.3) ratio, in 80-100 DEG C of silicone oil bath react 5-8h, reaction terminates
After be cooled to room temperature, separate upper strata product with decanting process, catalyst be used for lower secondary response.
As preferably, described alkene is 1-hexene, 1-octene, 1-decene, 1-laurylene, styrene, allyl chloride, acrylic acid
Methyl ester, methyl methacrylate, butyl acrylate, butyl methacrylate, allyl glycidyl ether.
As preferably, described silane containing hydrogen is triethoxy hydrogen silane, dichloromethylsilane, trichlorosilane alkane.
The present invention compared with prior art, provides the benefit that:
1, using polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst, this catalyst has preferably selection
Property good and active, good stability, and being easily isolated.
2, the catalyst of the present invention comprises bimetallic, plays promoting catalysis by introducing the second metal, improves β addition product in product
Selectivity；The polyether segment introduced, can play co-catalysis and stablize center platinum effect；The highly polar ionic bond introduced,
Causing catalyst immiscible with product so that catalyst is easily isolated, convenient recycling, the repeatable utilization rate of catalyst is high.
3, the preparation method of the catalyst of the present invention is simple and quick, using the teaching of the invention it is possible to provide colory catalyst.
4, addition product prepared by the method for preparing catalyst of the hydrosilylation of the catalyst of the present invention, the conversion of reactant are used
Rate is high, product
Detailed description of the invention
Below by specific embodiment, technical scheme is further described explanation.
If without specified otherwise, the raw material employed in embodiments of the invention is raw material commonly used in the art, institute in embodiment
The method used, is the conventional method of this area.
The preparation method of a kind of catalyst for hydrosilylation of olefins, comprises the following steps:
(1) with the Polyethylene Glycol that mean molecule quantity is 200,300,400,600, it is raw material with thionyl chloride and imidazoles respectively,
Preparing tetra-kinds of end group imidazoles Polyethylene Glycol of A, B, C, D, structural formula is:
Tetra-kinds of end group imidazoles Polyethylene Glycol of described A, B, C, D, the n=4 in A, the n=6 in B, the n=8 in C, D
In n=12；
This preparation method is according to document New J.Chem., and the method in 2013,37,269 is carried out；
(2) by above-mentioned prepared four kinds of end groups imidazoles Polyethylene Glycol A, B, C, D respectively with 1-chlorinated carboxylic acid according to mol ratio
1:2 joins in the reaction vessel with magnetic agitation, heater and condensing unit, and makees reaction dissolvent with trichloroethane,
At 60-90 DEG C, stirring reaction 12h；
(3) the mixture cooling then above-mentioned reaction obtained, cleans twice by ethyl acetate after going the supernatant, decompression again
Remove residual solvent, be carboxylic acid functional imidazole salts, stand-by；
(4) above-mentioned prepared carboxylic acid functional imidazole salts is dissolved in dehydrated alcohol, according to carboxylic acid functional imidazole salts and metal alcoxyl
The mol ratio of based compound is the ratio of 1:1, adds ferrous iron, copper, zinc, calcium or the alkoxide compound of magnesium, at 40-60 DEG C,
Stirring reaction 3h, then removal of solvent under reduced pressure, obtain solid product；
(5) above-mentioned gained solid product is suspended in anhydrous tetrahydro furan, under room temperature, adds tert-butyl group potassium alcoholate, stir 30 points
Clock, is subsequently adding karstedt catalyst (platinum/alkyl imidazole mol ratio is 1:1) stirring 1h, removes solvent, obtain for alkene
The catalyst of hydrocarbon hydrosilylation.
A kind of catalyst for hydrosilylation of olefins prepared, is cyclized polyethers-N-heterocycle card for dibasic carboxylic acid slaine
Guest's platinum complex, the structural formula of described catalyst is:
In structural formula:
M (L)=Platinum is tetravalence；
M (1) is bivalent metal ion；M=1 or 2 or 3；N=4 or 6 or 8 or 12.
The preparation of catalyst:
Embodiment 1:
In the there-necked flask of 100 milliliters, add imidazole radicals Polyethylene Glycol A3.38g, monoxone 1.88g, trichloroethane 30 milli
Rise, be warming up to 80 DEG C of stirring reaction 12h, be cooled to room temperature.Decanting process removes trichloroethane, with ethyl acetate (25mL × 2)
Cleaning, decompression removes residual solvent.Solid, with 50 milliliters of anhydrous alcohol solutions, adds 1.98g bis-tert-butoxy ferrous iron Fe (OtBu)2,
50 DEG C of stirring reaction 3h, rotary evaporation removes ethanol, is dried 24h in 70 DEG C of vacuum drying ovens.Gained solid is suspended in 25 milliliters
Anhydrous tetrahydro furan, adds tert-butyl group potassium alcoholate 2.24g, stirs 30 minutes, adds the karstedt catalyst 39g of platinum content 10%,
Stirring 1h, removes solvent, prepares carboxylic metallic salt cyclisation polyethers-N-heterocycle carbine platinum complex integration catalyst.
Take this catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain close
Closing in container, react 8h in 80 DEG C of silicone oil baths, styrene conversion rate is 78.7%, and β addition compound product selectivity is 90.3%.
Separate upper strata product, add another part of 1mol styrene and 1.1mol triethoxy hydrogen silane, react 10h at the same terms,
Styrene conversion rate is 80.6%, and β addition compound product selectivity is 92.4%.
Embodiment 2:
Take the catalyst of 0.1mmol embodiment 1,1mol 1-hexene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic agitation
In sub hermetic container, reacting 4h, 1-hexene conversion ratio in 80 DEG C of silicone oil baths is 99.3%, and β addition compound product selectivity is 99.4%.
Separate upper strata product, add another part of 1mol 1-hexene and 1.1mol triethoxy hydrogen silane, react 4h at the same terms,
1-hexene conversion ratio is 99.0%, and β addition compound product selectivity is 99.7%.
Embodiment 3:
Take 0.1mmol embodiment 1 catalyst, 1mol 1-octene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar
Obtaining in hermetic container, reacting 4h, 1-octene conversion in 80 DEG C of silicone oil baths is 98.3%, and β addition compound product selectivity is 99.1%.
Embodiment 4:
Taking 0.1mmol embodiment 1 catalyst, 1mol 1-hexene and 1.1mol dichloromethylsilane are placed in and fill magnetic stir bar
Obtaining in hermetic container, reacting 4h, 1-hexene conversion ratio in 80 DEG C of silicone oil baths is 99.5%, and β addition compound product selectivity is 99.3%.
Embodiment 5:
Taking 0.1mmol embodiment 1 catalyst, 1mol 1-octene and 1.1mol dichloromethylsilane are placed in and fill magnetic stir bar
Obtaining in hermetic container, reacting 4h, 1-octene conversion in 80 DEG C of silicone oil baths is 98.5%, and β addition compound product selectivity is 99.2%.
Embodiment 6:
In embodiment 1, replace monoxone with 1-chloropropionic acid 2.16g, prepare polyethers, N-heterocycle carbine platinum complex carboxylic acid metal
Salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 82.1%, and β addition compound product selectivity is 85.7%.
Embodiment 7:
Take 0.1mmol embodiment 6 catalyst, 1mol 1-hexene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar
Obtaining in hermetic container, reacting 4h, 1-hexene conversion ratio in 80 DEG C of silicone oil baths is 98.3%, and β addition compound product selectivity is 99.1%.
Embodiment 8:
In embodiment 1, replace monoxone with 1-chloro-butyric acid 2.44g, prepare polyethers, N-heterocycle carbine platinum complex carboxylic acid metal
Salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 82.1%, and β addition compound product selectivity is 90.3%.
Embodiment 9:
Take 0.1mmol embodiment 8 catalyst, 1mol 1-hexene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar
Obtaining in hermetic container, reacting 4h, 1-hexene conversion ratio in 80 DEG C of silicone oil baths is 99.5%, and β addition compound product selectivity is 99.6%.
Embodiment 10:
Take 0.1mmol embodiment 8 catalyst, 1mol 1-octene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar
Obtaining in hermetic container, reacting 4h, 1-octene conversion in 80 DEG C of silicone oil baths is 96.5%, and β addition compound product selectivity is 99.1%.
Embodiment 11:
In embodiment 1, replace imidazole radicals Polyethylene Glycol A with imidazole radicals Polyethylene Glycol B4.26g, prepare N-heterocycle carbine platinum and join
Compound carboxylic metallic salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 93.1%, and β addition compound product selectivity is 94.8%.
Embodiment 12:
In embodiment 1, replace imidazole radicals Polyethylene Glycol A with imidazole radicals Polyethylene Glycol C5.14g, prepare N-heterocycle carbine platinum and join
Compound carboxylic metallic salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 90.1%, and β addition compound product selectivity is 92.8%.
Embodiment 13:
In embodiment 1, imidazole radicals Polyethylene Glycol D6.9g replaces imidazole radicals Polyethylene Glycol A, prepares polyethers, N-heterocycle carbine platinum
Complex carboxylic acids acid metal salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 89.3%, and β addition compound product selectivity is 87.6%.
Embodiment 14:
Take the made catalyst of 0.1mmol embodiment 13,1mol allyl chloride and 1.1mol trichlorosilane alkane to be placed in and fill magnetic force and stir
Mixing in sub hermetic container, react 5h in 80 DEG C of silicone oil baths, allyl chloride conversion ratio is 94.3%, γ-chloropropyl trichloro-silane choosing
Selecting property is 89.2%.
Embodiment 15:
Take the made catalyst of 0.1mmol embodiment 13,1mol allyl glycidyl ether and 1.1mol dichloromethylsilane to put
Obtaining in hermetic container in filling magnetic stir bar, react 5h in 80 DEG C of silicone oil baths, allyl glycidyl ether conversion ratio is 93.3%,
2-glycidoxypropyl dichlorosilane selectivity 86.3%.
Embodiment 16:
Take the made catalyst of 0.1mmol embodiment 13,1mol butyl acrylate and 1.1mol dichloromethylsilane to be placed in and fill
Magnetic stir bar obtains in hermetic container, reacts 5h in 80 DEG C of silicone oil baths, and butyl acrylate conversion ratio is 87.4%, 2-methyl dichloro
Silica-based butyl propionate selectivity 86.3%.
Embodiment 17:
Take the made catalyst of 0.1mmol embodiment 12,1mol butyl acrylate and 1.1mol trichlorosilane alkane to be placed in and fill magnetic force
Stirrer obtains in hermetic container, reacts 5h in 80 DEG C of silicone oil baths, and butyl acrylate conversion ratio is 85.3%, the silica-based propanoic acid of 2-trichlorine
Butyl ester selectivity 85.6%.
Embodiment 18:
Take the made catalyst of 0.1mmol embodiment 13,1mol methyl methacrylate and 1.1mol trichlorosilane alkane to be placed in and fill
Magnetic stir bar obtains in hermetic container, reacts 5h in 80 DEG C of silicone oil baths, and methyl methacrylate conversion ratio is 90.3%, 2-trichlorine
Silica-based-1-methylpropanoic acid methyl ester selectivity 86.6%.
Embodiment 19:
In embodiment 1, with two tert-butoxy zinc Zn (OtBu)22.07g replaces Fe (OtBu)2, prepare polyethers, N-heterocycle carbine platinum
Complex carboxylic acids acid metal salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 87.3%, and β addition compound product selectivity is 90.5%.
Embodiment 20:
In embodiment 1, with diethoxy magnesium Mg (OEt)21.14g replaces Fe (OtBu)2, preparing polyethers, N-heterocycle carbine platinum is joined
Compound carboxylic metallic salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 80.4%, and β addition compound product selectivity is 85.4%.
Embodiment 21:
In embodiment 1, with diethoxy calcium Ca (OEt)21.3g replaces Fe (OtBu)2, preparing polyethers, N-heterocycle carbine platinum coordinates
Thing carboxylic metallic salt integration catalyst.
Take the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic stir bar and obtain
In hermetic container, reacting 10h in 80 DEG C of silicone oil baths, styrene conversion rate is 93.4%, and β addition compound product selectivity is 94.5%.
Embodiment 22:
Take catalyst in 0.05mmol embodiment 21,1mol styrene and 1.1mol triethoxy hydrogen silane to be placed in and fill magnetic force
Stirrer obtains in hermetic container, reacts 10h in 80 DEG C of silicone oil baths, and styrene conversion rate is 85.4%, and β addition compound product selectivity is
89.5%.
Claims (7)
1. the catalyst for hydrosilylation of olefins, it is characterised in that described catalyst is that the cyclisation of dibasic carboxylic acid slaine is poly-
Ether-N-heterocycle carbine platinum complex, the structural formula of described catalyst is:
In structural formula:
M (L)=
M (1) is bivalent metal ion；
M=1 or 2 or 3；
N=4 or 6 or 8 or 12.
A kind of catalyst for hydrosilylation of olefins the most according to claim 1, it is characterised in that described catalyst is
After double N-heterocycle carbine platinum complexes containing polyether segment are cyclized by dibasic carboxylic acid slaine, it is prepared from.
A kind of catalyst for hydrosilylation of olefins the most according to claim 1, it is characterised in that in described catalyst
Carboxylic metallic salt described in bivalent metal ion be Fe (II), Zn (II), Ca (II) or Mg (II).
The preparation method of a kind of catalyst for hydrosilylation of olefins the most according to claim 1, it is characterised in that bag
Include following steps:
(1) with the Polyethylene Glycol that mean molecule quantity is 200,300,400,600, it is raw material with thionyl chloride and imidazoles respectively, system
For obtaining tetra-kinds of end group imidazoles Polyethylene Glycol of A, B, C, D, structural formula is:
Tetra-kinds of end group imidazoles Polyethylene Glycol of described A, B, C, D, the n=4 in A, the n=6 in B, the n=8 in C, in D
N=12；
(2) by above-mentioned prepared four kinds of end groups imidazoles Polyethylene Glycol A, B, C, D respectively with 1-chlorinated carboxylic acid according to mol ratio 1:2
Join in the reaction vessel with magnetic agitation, heater and condensing unit, and make reaction dissolvent with trichloroethane,
At 60-90 DEG C, stirring reaction 12h；
(3) the mixture cooling then above-mentioned reaction obtained, cleans twice by ethyl acetate after going the supernatant again, and decompression removes
Residual solvent, is carboxylic acid functional imidazole salts, stand-by；
(4) above-mentioned prepared carboxylic acid functional imidazole salts is dissolved in dehydrated alcohol, according to carboxylic acid functional imidazole salts and metal alkoxide
The mol ratio of compound is the ratio of 1:1, adds ferrous iron, zinc, calcium or the alkoxide compound of magnesium, at 40-60 DEG C, stirs
Mix reaction 3h, then removal of solvent under reduced pressure, obtain solid product；
(5) above-mentioned gained solid product is suspended in anhydrous tetrahydro furan, under room temperature, adds tert-butyl group potassium alcoholate, stir 30 minutes,
It is subsequently adding karstedt catalyst stirring 1h, removes solvent, obtain the catalyst for hydrosilylation of olefins.
5. use an alkene Si-H addition reaction method for a kind of catalyst for hydrosilylation of olefins described in claim 1, its
Be characterised by, with catalyst, alkene and silane containing hydrogen mol ratio for (0.1-0.2): 1:(1-1.3) ratio, at 80-100 DEG C of silicone oil bath
Middle reaction 5-8h, reaction is cooled to room temperature after terminating, separates upper strata product with decanting process, and catalyst is used for lower secondary response.
A kind of alkene Si-H addition reaction method the most according to claim 5, it is characterised in that described alkene be 1-hexene, 1-octene,
1-decene, 1-laurylene, styrene.
A kind of alkene Si-H addition reaction method the most according to claim 6, it is characterised in that described silane containing hydrogen is triethoxy hydrogen
Silane, dichloromethylsilane, trichlorosilane alkane.
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