CN104324751A - Catalyst used for olefin hydrosilylation reaction, preparation method thereof and the olefin hydrosilylation reaction employing the catalyst - Google Patents
Catalyst used for olefin hydrosilylation reaction, preparation method thereof and the olefin hydrosilylation reaction employing the catalyst Download PDFInfo
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Abstract
The invention relates to the field of organic chemistry and particularly relates to a catalyst used for an olefin hydrosilylation reaction, a preparation method thereof and the olefin hydrosilylation reaction employing the catalyst. The catalyst is prepared by carrying out a divalent metal carboxylate cyclization reaction to a double N-heterocyclic carbine platinum complex containing a polyether chain segment. The catalyst is good in selectivity and activity, is good in stability, is easy to separate and is high in recyclable ratio.
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 adopt the hydrosilylation of olefins of this catalyst.
Background technology
The hydrosilylation of catalysis unsaturated compound and silane containing hydrogen is the important topic (J.Organomet.Chem., 2003,681,91-97) of organosilicon chemistry and industry, and the most important thing in this problem is then the research and development of effective catalyst.Hydrosilylation of olefins is synthesizing organo-silicon coupling agent and one of function organo-silicon compound and the most important approach of polymer, for alkene Si―H addition reaction, current industry and laboratory use Speier catalyst (aqueous isopropanol of chloroplatinic acid) and Karstedt catalyst (the tetramethyl divinyl disiloxane complex of platinum) usually, according to service condition and suitable substrates, often auxiliary agent will be added, to improve above-mentioned two class catalyst system and catalyzing catalytic activitys and selective.The reports such as Mark ó, for Karstedt catalyst, N-heterocycle carbine is utilized to make its part tetramethyl divinyl disiloxane of ligand-displacement, obtained N-heterocycle carbine platinum complex has high activity to alkene Si―H addition reaction, simultaneously in course of reaction, and catalyst system stabiliser, do not produce platinum black precipitation (Science, 2002,298,204).In addition, research shows, carboxylic acid function's polyethylene glycol improves platinum catalysis hydrosilylation of olefins activity and selective (Appl.Organomet.Chem., 2011,25,400-405).
And existing market does not solve the problem accordingly for catalyst for addition reaction of hydrogen and silicon, and current catalyst ubiquity is not enough.
Summary of the invention
The object of the invention is to overcome problem described above, a kind of catalyst for hydrosilylation of olefins, its preparation method being provided and adopting the hydrosilylation of olefins of this catalyst
In order to reach foregoing invention object, the present invention by the following technical solutions:
For a catalyst for hydrosilylation of olefins, described catalyst is dibasic carboxylic acid slaine cyclisation polyethers-N-heterocycle carbine platinum complex, and 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 be containing two N-heterocycle carbine platinum complexes of polyether segment by after the cyclisation of dibasic carboxylic acid slaine, be prepared from.
As preferably, the metal in the carboxylic metallic salt in described catalyst is iron, zinc, calcium or magnesium, and described bivalent metal ion is Fe (II), Zn (II), Ca (II) or Mg (II).
For a preparation method for the catalyst of hydrosilylation of olefins, comprise the following steps:
(1) with mean molecule quantity be 200,300,400,600 polyethylene glycol, be raw material with thionyl chloride and imidazoles respectively, prepare A, B, C, D tetra-kinds of end group imidazoles polyethylene glycol (that is: holding position to be imidazole radicals polyethylene glycol), structural formula is:
Described A, B, C, D tetra-kinds of end group imidazoles polyethylene glycol, the n=4 in A, the n=6 in B, the n=8 in C, the n=12 in D;
(2) above-mentioned obtained four kinds of end group imidazoles polyethylene glycol A, B, C, D are joined in the reaction vessel with magnetic agitation, heater and condensing unit with 1-chlorinated carboxylic acid according to mol ratio 1:2 respectively, and make reaction dissolvent with trichloroethanes, at 60-90 DEG C, stirring reaction 12h;
(3) then by the above-mentioned mixture cooling be obtained by reacting, clean twice with ethyl acetate again after removing supernatant liquor, decompression removing residual solvent, is carboxylic acid functional imidazole salts, stand-by;
(4) above-mentioned obtained carboxylic acid functional imidazole salts is dissolved in absolute ethyl alcohol, be the ratio of 1:1 according to the mol ratio of carboxylic acid functional imidazole salts and metal alkoxide, add the alkoxide compound of ferrous iron, copper, zinc, calcium or magnesium, at 40-60 DEG C, stirring reaction 3h, then removal of solvent under reduced pressure, obtains 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, then add karstedt catalyst and stir 1h, except desolventizing, obtain the catalyst for hydrosilylation of olefins.
Addition and the imidazole radicals equivalent of tert-butyl group potassium alcoholate.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 adopting above-mentioned a kind of catalyst for hydrosilylation of olefins, be (0.1-0.2): 1:(1-1.3 with catalyst, alkene and silane containing hydrogen mol ratio) ratio, 5-8h is reacted in 80-100 DEG C of silicone oil bath, room temperature is cooled to after reaction terminates, separate upper strata product with decanting process, catalyst is used for lower secondary response.
As preferably, described alkene is 1-hexene, 1-octene, 1-decene, 1-laurylene, styrene, allyl chloride, methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, allyl glycidyl ether.
As preferably, described silane containing hydrogen is triethoxy hydrogen silane, dichloromethylsilane, trichlorosilane alkane.
Compared with prior art, beneficial effect is in the present invention:
1, use polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst, this catalyst has good selective good and active, good stability, and is easy to be separated.
2, catalyst of the present invention comprises bimetallic, plays promoting catalysis by introducing the second metal, and in raising product, β addition product is selective; The polyether segment introduced, can play co catalysis and the effect of stable center platinum; The strong polar ion key introduced, causes catalyst and product immiscible, makes catalyst be easy to separation, conveniently recycles, catalyst can recycling rate of waterused high.
3, the preparation method of catalyst of the present invention is simple and quick, can provide colory catalyst.
4, the addition product adopting the method for preparing catalyst of the hydrosilylation of catalyst of the present invention to prepare, the conversion ratio of reactant is high, product
Detailed description of the invention
Below by specific embodiment, explanation is further described to technical scheme of the present invention.
If without specified otherwise, the raw material adopted in embodiments of the invention is the conventional raw material in this area, and the method adopted in embodiment, is the conventional method of this area.
For a preparation method for the catalyst of hydrosilylation of olefins, comprise the following steps:
(1) with mean molecule quantity be 200,300,400,600 polyethylene glycol, be raw material with thionyl chloride and imidazoles respectively, prepare A, B, C, D tetra-kinds of end group imidazoles polyethylene glycol, structural formula is:
Described A, B, C, D tetra-kinds of end group imidazoles polyethylene glycol, the n=4 in A, the n=6 in B, the n=8 in C, the n=12 in D;
This preparation method is according to document New J.Chem., 2013,37, and the method in 269 is carried out;
(2) above-mentioned obtained four kinds of end group imidazoles polyethylene glycol A, B, C, D are joined in the reaction vessel with magnetic agitation, heater and condensing unit with 1-chlorinated carboxylic acid according to mol ratio 1:2 respectively, and make reaction dissolvent with trichloroethanes, at 60-90 DEG C, stirring reaction 12h;
(3) then by the above-mentioned mixture cooling be obtained by reacting, clean twice with ethyl acetate again after removing supernatant liquor, decompression removing residual solvent, is carboxylic acid functional imidazole salts, stand-by;
(4) above-mentioned obtained carboxylic acid functional imidazole salts is dissolved in absolute ethyl alcohol, be the ratio of 1:1 according to the mol ratio of carboxylic acid functional imidazole salts and metal alkoxide, add the alkoxide compound of ferrous iron, copper, zinc, calcium or magnesium, at 40-60 DEG C, stirring reaction 3h, then removal of solvent under reduced pressure, obtains solid product;
(5) above-mentioned gained solid product is suspended in anhydrous tetrahydro furan, under room temperature, add tert-butyl group potassium alcoholate, stir 30 minutes, then add karstedt catalyst (platinum/alkyl imidazole mol ratio is 1:1) and stir 1h, except desolventizing, obtain the catalyst for hydrosilylation of olefins.
A kind of catalyst for hydrosilylation of olefins prepared, be dibasic carboxylic acid slaine cyclisation polyethers-N-heterocycle carbine 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, trichloroethanes 30 milliliters, be warming up to 80 DEG C of stirring reaction 12h, be cooled to room temperature.Decanting process removing trichloroethanes, with ethyl acetate (25mL × 2) cleaning, decompression removing residual solvent.Solid 50 milliliters of anhydrous alcohol solutions, add the ferrous Fe (O of 1.98g bis-tert-butoxy
tbu)
2, 50 DEG C of stirring reaction 3h, rotary evaporation removing ethanol, 70 DEG C of vacuum drying chamber inner drying 24h.Gained Solid Suspension, in 25 milliliters of anhydrous tetrahydro furans, adds tert-butyl group potassium alcoholate 2.24g, stirs 30 minutes, add the karstedt catalyst 39g of platinum content 10%, stir 1h, except desolventizing, obtained carboxylic metallic salt cyclisation polyethers-N-heterocycle carbine platinum complex integration catalyst.
Get this catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 8h in 80 DEG C of silicone oil baths, styrene conversion rate be 78.7%, β addition compound product selective be 90.3%.
Separate upper strata product, add another part of 1mol styrene and 1.1mol triethoxy hydrogen silane, the same terms reaction 10h, styrene conversion rate be 80.6%, β addition compound product selective be 92.4%.
Embodiment 2:
Get the catalyst of 0.1mmol embodiment 1,1mol 1-hexene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-hexene conversion ratio be 99.3%, β addition compound product selective be 99.4%.
Separate upper strata product, add another part of 1mol 1-hexene and 1.1mol triethoxy hydrogen silane, the same terms reaction 4h, 1-hexene conversion ratio be 99.0%, β addition compound product selective be 99.7%.
Embodiment 3:
Get 0.1mmol embodiment 1 catalyst, 1mol 1-octene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-octene conversion be 98.3%, β addition compound product selective be 99.1%.
Embodiment 4:
Get 0.1mmol embodiment 1 catalyst, 1mol 1-hexene and 1.1mol dichloromethylsilane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-hexene conversion ratio be 99.5%, β addition compound product selective be 99.3%.
Embodiment 5:
Get 0.1mmol embodiment 1 catalyst, 1mol 1-octene and 1.1mol dichloromethylsilane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-octene conversion be 98.5%, β addition compound product selective be 99.2%.
Embodiment 6:
In embodiment 1, replace monoxone with 1-chloropropionic acid 2.16g, obtained polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 82.1%, β addition compound product selective be 85.7%.
Embodiment 7:
Get 0.1mmol embodiment 6 catalyst, 1mol 1-hexene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-hexene conversion ratio be 98.3%, β addition compound product selective be 99.1%.
Embodiment 8:
In embodiment 1, replace monoxone with 1-chloro-butyric acid 2.44g, obtained polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 82.1%, β addition compound product selective be 90.3%.
Embodiment 9:
Get 0.1mmol embodiment 8 catalyst, 1mol 1-hexene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-hexene conversion ratio be 99.5%, β addition compound product selective be 99.6%.
Embodiment 10:
Get 0.1mmol embodiment 8 catalyst, 1mol 1-octene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 4h in 80 DEG C of silicone oil baths, 1-octene conversion be 96.5%, β addition compound product selective be 99.1%.
Embodiment 11:
In embodiment 1, replace imidazole radicals polyethylene glycol A with imidazole radicals polyethylene glycol B4.26g, obtained N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 93.1%, β addition compound product selective be 94.8%.
Embodiment 12:
In embodiment 1, replace imidazole radicals polyethylene glycol A with imidazole radicals polyethylene glycol C5.14g, obtained N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 90.1%, β addition compound product selective be 92.8%.
Embodiment 13:
In embodiment 1, imidazole radicals polyethylene glycol D6.9g replaces imidazole radicals polyethylene glycol A, obtained polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 89.3%, β addition compound product selective be 87.6%.
Embodiment 14:
Get 0.1mmol embodiment 13 controlling catalysts, 1mol allyl chloride and 1.1mol trichlorosilane alkane are placed in and fill magnetic stir bar and obtain in closed container, react 5h in 80 DEG C of silicone oil baths, allyl chloride conversion ratio be 94.3%, γ-chloropropyl trichloro-silane selective be 89.2%.
Embodiment 15:
Get 0.1mmol embodiment 13 controlling catalysts, 1mol allyl glycidyl ether and 1.1mol dichloromethylsilane are placed in and fill magnetic stir bar and obtain in closed container, 5h is reacted in 80 DEG C of silicone oil baths, allyl glycidyl ether conversion ratio is 93.3%, 2-glycidoxypropyl dichlorosilane selective 86.3%.
Embodiment 16:
Get 0.1mmol embodiment 13 controlling catalysts, 1mol butyl acrylate and 1.1mol dichloromethylsilane are placed in and fill magnetic stir bar and obtain in closed container, react 5h in 80 DEG C of silicone oil baths, butyl acrylate conversion ratio is the silica-based butyl propionate of 87.4%, 2-methyl dichloro selective 86.3%.
Embodiment 17:
Get 0.1mmol embodiment 12 controlling catalysts, 1mol butyl acrylate and 1.1mol trichlorosilane alkane are placed in and fill magnetic stir bar and obtain in closed container, react 5h in 80 DEG C of silicone oil baths, butyl acrylate conversion ratio is the silica-based butyl propionate of 85.3%, 2-trichlorine selective 85.6%.
Embodiment 18:
Get 0.1mmol embodiment 13 controlling catalysts, 1mol methyl methacrylate and 1.1mol trichlorosilane alkane are placed in and fill magnetic stir bar and obtain in closed container, 5h is reacted in 80 DEG C of silicone oil baths, methyl methacrylate conversion ratio is 90.3%, 2-trichlorine silica-based-1-methylpropanoic acid methyl esters selective 86.6%.
Embodiment 19:
In embodiment 1, with two tert-butoxy zinc Zn (O
tbu)
22.07g replaces Fe (O
tbu)
2, obtained polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 87.3%, β addition compound product selective be 90.5%.
Embodiment 20:
In embodiment 1, with diethoxy magnesium Mg (OEt)
21.14g replaces Fe (O
tbu)
2, obtained polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 80.4%, β addition compound product selective be 85.4%.
Embodiment 21:
In embodiment 1, with diethoxy calcium Ca (OEt)
21.3g replaces Fe (O
tbu)
2, obtained polyethers, N-heterocycle carbine platinum complex carboxylic metallic salt integration catalyst.
Get the above-mentioned catalyst of 0.1mmol, 1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 93.4%, β addition compound product selective be 94.5%.
Embodiment 22:
Get catalyst in 0.05mmol embodiment 21,1mol styrene and 1.1mol triethoxy hydrogen silane are placed in and fill magnetic stir bar and obtain in closed container, react 10h in 80 DEG C of silicone oil baths, styrene conversion rate be 85.4%, β addition compound product selective be 89.5%.
Claims (8)
1. for a catalyst for hydrosilylation of olefins, it is characterized in that, described catalyst is dibasic carboxylic acid slaine cyclisation polyethers-N-heterocycle carbine platinum complex, and 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.
2. a kind of catalyst for hydrosilylation of olefins according to claim 1, is characterized in that, described catalyst be containing two N-heterocycle carbine platinum complexes of polyether segment by after the cyclisation of dibasic carboxylic acid slaine, be prepared from.
3. a kind of catalyst for hydrosilylation of olefins according to claim 1, it is characterized in that, metal in carboxylic metallic salt in described catalyst is iron, zinc, calcium or magnesium, and described bivalent metal ion is Fe (II), Zn (II), Ca (II) or Mg (II).
4. the preparation method of a kind of catalyst for hydrosilylation of olefins according to claim 1, is characterized in that, comprise the following steps:
(1) with mean molecule quantity be 200,300,400,600 polyethylene glycol, be raw material with thionyl chloride and imidazoles respectively, prepare A, B, C, D tetra-kinds of end group imidazoles polyethylene glycol, structural formula is:
Described A, B, C, D tetra-kinds of end group imidazoles polyethylene glycol, the n=4 in A, the n=6 in B, the n=8 in C, the n=12 in D;
(2) above-mentioned obtained four kinds of end group imidazoles polyethylene glycol A, B, C, D are joined in the reaction vessel with magnetic agitation, heater and condensing unit with 1-chlorinated carboxylic acid according to mol ratio 1:2 respectively, and make reaction dissolvent with trichloroethanes, at 60-90 DEG C, stirring reaction 12h;
(3) then by the above-mentioned mixture cooling be obtained by reacting, clean twice with ethyl acetate again after removing supernatant liquor, decompression removing residual solvent, is carboxylic acid functional imidazole salts, stand-by;
(4) above-mentioned obtained carboxylic acid functional imidazole salts is dissolved in absolute ethyl alcohol, be the ratio of 1:1 according to the mol ratio of carboxylic acid functional imidazole salts and metal alkoxide, add the alkoxide compound of ferrous iron, copper, zinc, calcium or magnesium, at 40-60 DEG C, stirring reaction 3h, then removal of solvent under reduced pressure, obtains 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, then add karstedt catalyst and stir 1h, except desolventizing, obtain the catalyst for hydrosilylation of olefins.
5. the preparation method of a kind of catalyst for hydrosilylation of olefins according to claim 4, is characterized in that, in karstedt catalyst, the mol ratio of platinum and alkyl imidazole is 1:1.
6. one kind adopts the hydrosilylation of olefins of a kind of catalyst for hydrosilylation of olefins according to claim 1, it is characterized in that, be (0.1-0.2): 1:(1-1.3 with catalyst, alkene and silane containing hydrogen mol ratio) ratio, 5-8h is reacted in 80-100 DEG C of silicone oil bath, room temperature is cooled to after reaction terminates, separate upper strata product with decanting process, catalyst is used for lower secondary response.
7. a kind of hydrosilylation of olefins according to claim 6, it is characterized in that, described alkene is 1-hexene, 1-octene, 1-decene, 1-laurylene, styrene, allyl chloride, methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, allyl glycidyl ether.
8. a kind of hydrosilylation of olefins according to claim 7, is characterized in that, described silane containing hydrogen is triethoxy hydrogen silane, dichloromethylsilane, trichlorosilane alkane.
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| CN109647532A (en) * | 2017-10-11 | 2019-04-19 | 中国科学院大连化学物理研究所 | A kind of application of the platinum orphan's atom of non-olefinic coordination in hydrosilylation |
| CN111690452A (en) * | 2020-06-22 | 2020-09-22 | 金陵科技学院 | Method for preparing organic silicon cottonseed oil base lubricating oil base oil |
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