CN100378111C - Compound, synthetic method and application of organosilicon containing carbon-oxygen-ether linkage - Google Patents
Compound, synthetic method and application of organosilicon containing carbon-oxygen-ether linkage Download PDFInfo
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- CN100378111C CN100378111C CNB200510027452XA CN200510027452A CN100378111C CN 100378111 C CN100378111 C CN 100378111C CN B200510027452X A CNB200510027452X A CN B200510027452XA CN 200510027452 A CN200510027452 A CN 200510027452A CN 100378111 C CN100378111 C CN 100378111C
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Abstract
The present invention relates to an organosilicon compound containing a carbon-oxygen-ether linkage, a synthetic method thereof and an application of the organosilicon compound containing the carbon-oxygen-ether linkage in the surface modification of mesoporous silicon materials. The structural formula of the compound is disclosed in the figure I; the compound can be used for synthesizing the following organosilicon materials containing the carbon-oxygen-ether linkage, (which is disclosed in the figure II.), wherein R is hydrocarbyl of C1 to C6, and R1, R2 and R3 are alkyl groups of C1 to C6; mesoporous materials whose mesoporous pore canals are 2.0 to 50 nm have a bidimensional cubic syngony, a bidimensional hexagonal syngony, a tridimensional cubic syngony or a tridimensional hexagonal syngony, which is disclosed in the figure III. The method has the advantages of simplicity, high efficiency, easy obtainment of material, simple operation, convenient post-treatment, high reaction yield, simple reaction device and easy industrial production.
Description
Technical field
The present invention relates to the novel organosilicon containing carbon-oxygen-ether linkage compound of a class, synthetic method and application thereof.The synthetic method of such compound is to generate silicoorganic compound by the alkene hydrosilation reaction.Can synthesize the organosilicon that contains different numbers and dissimilar carbon oxygen-ether linkages by different olefin substrate; Perhaps remarry and receive the silicon materials surface, thus the character of change silicon materials.Silicon materials after the modification can be applicable to the catalyst-loaded of synthetic precious metal catalyst.The also potential absorption that is applied to metal of silicon materials after the modification, the hydrophilic hydrophobic adjusting of material surface, phase-transfer catalysis is for its suitability for industrialized production provides wide prospect.
Background technology
Since the MCM-4 mesoporous silicon material that the scientist of Mobil company in 1992 takes the lead in reporting, " (a) C.T.Kresge, M.E.Leonowicz; W.J.Roth, J.C.Vartuli, J.S.Beck; Nature, 1992,359; 710. (b) J.S.Beck, J.C.Vartuli, W.J.Roth; M.E.Leonowicz; C.T.Kresge, K.D.Schmitt, C.T-W.Chu, D.H.Olson, E.W.Sheppard, S.B.McCullen, J.B.Higgins, J.L.Schlenker, J.Am.Chem.Soc.1992,114,10834. " mesoporous silicon material has obtained numerous scientists' favor.This silicon materials have numerous advantages, such as very high specific surface area (500-1000m
2/ g), the regular mesopore orbit of adjustable homogeneous, very high chemical stability and hydrothermal stability." (a) D.Zhao, J.Feng, Q.Huo; N.Melosh, G.H.Fredrickson, B.F.Chmelka; G.D.Stucky, Science1998,279; 548. (b) Y.Liu, W.Zhang, T.J.Pinnavaia; J.Am.Chem.Soc.2000,122,8791. (c) Y.Liu; W.Zhang, T.J.Pinnavaia, Angew.Chem.Int.Ed.2001,40,1255. (d) Y.Han, F.-S.Xiao, S.Wu, J.Phys.Chem.B 2001,105,7963. (e) Y.Han, D.Li, L.Zhao, F.-S.Xiao, Angew.Chem.Iht.Ed.2003,42,3633. " and the mesoporous silicon material surface have abundant silicon hydroxyl; through surface modified, can synthesize and have polyfunctional mesoporous material.The mesoporous material that these organosilicon modifications are crossed can be applicable to catalysis, " (a) D.E.De Vos, M.Dams; B.F.Sels, P.A.Jacobs, Chem.Rev.2002; 102,3615. (b) R.Raja, J.M.Thomas; M.D.Jones, B.F.G Johnson .D.E.W Vaughan; J.Am.Chem.Soc.2003,125,14982. (c) S.Huh; H.-T.Chen, J.W.Wiench, M.Pruski, V.S.-Y.Lin, J.Am.Chem.Soc.2004,126,1010. (d) C.H.Christensen, K.Johannsen, I.Schmidt, C.H.Christensen, J.Am.Chem.Soc.2003,125,13370. (e) S.K.Mohapatra, S.U.Sonavane, R.V.Jayaram, P.Selvam, Org.Lett.2002; 4,4297. (f) M.Jia; A.Seifert; W.R.Thiel, Chem.Mater.2003,15,2174. (g) M.Jia, A.Seifert, M.Berger, H.Giegengack, S.Schulze, W.R.Thiel, Chem.Mater.2004,16,877. (h) M.V.Vasylyev, R.Neumann, J.Am.Chem.Soc.2004,126,884. (i) K.Mukhopadhyay, A.B.Mandale, R.V.Chaudhari, Chem.Mater.2003,15,1766. (j) V.S.-Y.Lin, D.R.Radu, M.-K.Han, W.Deng, S.Kuroki, B.H.Shanks, M.Pruski, J.Am.Chem.Soc.2002,124,9040. (k) A.Vinu, T.Krithiga, V.Murugesan, M.Hartmann, Adv.Mater.2004,16,1817. (1) R.Becker, H.Parala, F.Hipler, O.P.Tkachenko, K.V.Klementiev, W.Gr ü nert, H.Wilmer, O.Hinrichsen, M.Muhler, A.Birkner, C.W ll, S.Sch fer, R.A.Fischer, Angew.Chem.Inter.Ed.2004,43,2839. (m) M.Chatterjee, F.Y.Zhao, Y.Ikushima, Adv.Syn.﹠amp; Catal.2004,346,459. (n) D.S.Shephard, T.Maschmeyer, B.F.G.Johnson, J.M.Thomas, G.Sankar, D.Ozkaya, W.Zhou, R.D.Oldroyd, R.G.Bell, Angew.Chem.Inter.Ed.1997,36,2242. (o) P.Sreekanth, S.-W.Kim, T.Hyeon, B.M.Kim, Adv.Syn.﹠amp; Catal.2003,345,936. (p) J.H.Clark, A.J.Butterworth, S.J.Tavener, A.J.Teasdale, S.J.Barlow, T.W.Bastock, K.Martin, J.Chem.T ech.Biotechnol.1997,68,367. (q) J.D.Bass, S.L.Anderson, A.Katz, Angew.Chem.Int.Ed.2003,42,5219. (r) P.Ferreira, I.S.Gonc, F.E.K ü hn, A.D.Lopes, M.A.Martins, Ma.Pillinger, A.Pina, J.Rocha, C.C.
A.M.Santos, T.M.Santos, A.A.Valente.Eur.J.Inorg.Chem.2000,2263. (s) K.Mukhopadhyay, A.B.Mandale, R.V.Chaudhart, Chem.Mater.2003,15,1766. " absorption of metal ion, " (a) X.Feng, G.E.Fryxell, L.-Q.Wang, A.Y.Kim, J.Liu, K.M.Kemner, Science, 1997,276,923. (b) L.Mercier, T.J.Pinnavaia, Adv.Mater.1997,9,500. (c) J.Liu, X.Feng, G.E.Fryxell, L.-Q.Wang, A.Y.Kim, M.Gong, Adv.Mater.1998,10,161. (d) A.Walcarius, M.Etienne, B.Lebeau, Chem.Mater.2003,15,2161. (e) A.Walcarius, C.
Chem.Mater.2003,15,4181. (f) V.Antochshuk, Ok.Olkhovyk, Mi.Jaroniec, I.-S.Park, R.Ryoo, Langmuir, 2003,19,3031. " controlling slow release of medicine or guest molecule, " (a) N.K.Mal, M.Fujiwara, Y.Tanaka, Nature 2003,421,350. (b) N.K.Mal, M.Fujiwara, Y.Tanaka, T.Taguchi, M.Matsukata, Chem.Mater.2003,15,3385. (c) C.-Y.Lai, B.G.Trewyn, D.M.Jeftinija, K.Jeftinija, S.Xu, S.Jeftinija, V.S.-Y.Lin, J.Am.Chem.Soc.2003,125,4451. (d) D.R.Radu, C.-Y.Lai, K.Jeftinija, E.W.Rowe, S.Jeftinija, V.S.-Y.Lin, J.Am.Chem.Soc.2004,126,13216. (e) R.Hernandez, H.-R.Tseng, J.W.Wong, J.F.Stoddart, J.I.Zink, J.Am.Chem.Soc.2004,126,3370. " and the preparation of nano material." (a) E.W.Hagaman, H.Zhu, S.H.Overbury, S.Dai; Langmir, 2004,20,9577. " are although reported with the Platinic chloride to be catalyzer in the document " (a) M.E.Havill; I.Joffe, H.W.Post, J.Org.Chem.1948,2; 282. (b) A.Behr, F.Naendrup, D.Obst, Adv.Sunth.Catal; 2002,344,1142 ", generate silicoorganic compound by the alkene hydrosilation reaction, still, this novel carbon-oxygen bond organosilicon that contains was not also reported.Because this organosilicon has the structure that is similar to crown ether, therefore, have complex ability and and the amphipathic property very strong to metal by the mesoporous material of these organosilicon modifications.Here reported first the mesoporous material carried palladium catalyst of modifying by this organosilicon.This catalyzer has shown high catalytic activity in reaction, and stable in the air, and is environmentally friendly, and reusable edible and water are as solvent.
Summary of the invention
The purpose of this invention is to provide a kind of new compound, i.e. the organosilicon containing carbon-oxygen-ether linkage compound.
Purpose of the present invention also provides the synthetic method of above-mentioned organosilicon containing carbon-oxygen-ether linkage compound.
Purpose of the present invention also provides a kind of purposes by above-mentioned silicoorganic compound, promptly is used for the surface-modified of silicon materials.
The structural formula that organosilicon containing carbon-oxygen-ether linkage compound of the present invention is following in addition:
Wherein n is between 1～20, R
1, R
2, R
3Be C
1～6Alkyl, R is C
1～6Alkyl, as C
1～6Alkyl or phenyl
The synthetic method of organosilicon containing carbon-oxygen-ether linkage compound of the present invention can be synthetic by following method, and typical reaction formula is as follows:
Method of the present invention: under-78～70 ℃ of temperature of organic solvent neutralization, will
Obtained carbon oxygen-ether linkage silicoorganic compound in 0.5～48 hour with catalyst reaction.Wherein,
With the mol ratio of catalyzer be 1: 2～100: 0.001～10.0.Recommending mol ratio is 1: 2.2～30: 0.20～0.001.
Catalyst system therefor can be Platinic chloride (H
2PtCl
6) or acetylacetone based rhodium (Rh (acac)
3) etc.Reaction solvent is conventional organic solvent, as normal hexane, hexanaphthene, toluene, tetrahydrofuran (THF), methylene dichloride, dimethyl sulfoxide (DMSO), N, and dinethylformamide, 1,4-dioxane, acetone, ether or acetonitrile etc.
Above-mentioned organosilicon containing carbon-oxygen-ether linkage compound of the present invention can be used for the synthetic of modification silicon materials, organosilicon containing carbon-oxygen-ether linkage material and following structural formula;
Wherein n can be between 1～20, and R can be C
1～6Alkyl, as C
1～6Alkyl or phenyl,
Be mesoporous material, described mesoporous material can be that mesopore orbit is that 2.0～50nm, mesoporous material crystallographic system can be two dimension cube, two dimension six sides, three-dimensional cubic or three-dimensional six sides.The SiO 2 mesoporous materials that preferably meets above-mentioned condition.
It is as follows that above-mentioned carbon oxygen-ether linkage silicoorganic compound are used for the typical reaction formula of synthetic organosilicon containing carbon-oxygen-ether linkage silicon materials:
, wherein n can be between 1～20, and R is C
1～6Alkyl, can be alkyl such as methyl, ethyl, propyl group, hexyl, perhaps phenyl, the organosilicon containing carbon-oxygen-ether linkage compound is as previously mentioned.Mesoporous material can be that mesopore orbit is the silicon materials of 2.0～50nm, and the mesoporous material crystallographic system can be two dimension cube, two dimension six sides, three-dimensional cubic or three-dimensional six sides.The SiO 2 mesoporous materials that preferably meets above-mentioned condition.
Above-mentioned organosilicon containing carbon-oxygen-ether linkage silicon materials synthetic method: be in organic solvent, above-mentioned mesoporous material and silicoorganic compound obtained the silicon materials of carbon oxygen-ether linkage modified with organosilicon compounds 20～200 ℃ of thermotonuses in 2～48 hours.The element silicon mol ratio of mesoporous material and carbon oxygen-ether linkage silicoorganic compound is 10～10000: 1.Recommending mol ratio is 10～300: 1.
Used reaction solvent is conventional organic solvent, as normal hexane, hexanaphthene, toluene, tetrahydrofuran (THF), methylene dichloride, dimethyl sulfoxide (DMSO), N, and dinethylformamide, 1,4-dioxane, acetone, ether, acetonitrile etc.
Above-mentioned organosilicon containing carbon-oxygen-ether linkage silicon materials of the present invention are expected to synthesize the carrying metal catalyzer.
The present invention generates silicoorganic compound by the alkene hydrosilation reaction.Can synthesize the organosilicon that contains different numbers and dissimilar carbon-oxygen bonds by different olefin substrate.This method preparation is simple, is a kind of method easily and effectively.(1) raw material conveniently is easy to get, and is simple to operate, convenient post-treatment.(2) reaction yield is higher.(3) conversion unit is simple, is easy to suitability for industrialized production.
Such silicoorganic compound can grafting arrive the silicon materials surface, thereby change the character of silicon materials.Silicon materials after the modification are hopeful to be used for supporting of metal palladium catalyst.
Embodiment
Following examples help to understand the present invention, but are not limited to content of the present invention:
Embodiment 1
(1) preparation of silicoorganic compound 1:
Operate as follows: Platinic chloride (0.5mol%) adds ethyl-allyl group-tetraethylene glycol (0.1mol), triethoxysilicane hydrogen (0.3mol), stirring at room 1 day 180 ℃ of vacuum-dryings 2 hours.Steam and remove excessive triethoxysilicane hydrogen, the vacuum pump decompression, 178 ℃ steam colourless liquid, obtain product 27.5g.
1H?NMR(300MHz，CDCl
3)：δ3.79(q，J＝7.2Hz，6H)，3.64-3.43(m，18H)，3.39(t，J＝6.9Hz，2H)，1.71-1.61(m，2H)，1.19-1.14(m，12H)，0.59(t，J＝8.4Hz，2H)。
13C NMR (75MHz, CDCl
3): δ 73.4,70.9, and 70.6,70.1,63.0,51.3,17.9,15.5,14.7,8.0; MS m/z (%) 337 (100), 427 (M
+, 35.45); The ultimate analysis calculated value, C
19H
42O
8Si:C, 53.49; H, 9.92; Measured value: C, 53.65; H, 9.70.
Embodiment 2
(2) preparation of silicoorganic compound 2:
Operate as follows: operate as follows: Platinic chloride (0.5mol%) adds methyl-allyl group-tetraethylene glycol (0.1mol), triethoxysilicane hydrogen (0.3mol), stirring at room 1 day 180 ℃ of vacuum-dryings 2 hours.Steam and remove excessive triethoxysilicane hydrogen, the vacuum pump decompression, 178 ℃ steam colourless liquid, obtain product 27.3g.
1H?NMR(300MHz，CDCl
3)：δ3.78(q，J＝7.2Hz，6H)，3.64-3.43(m，18H)，3.39(t，J＝6.9Hz，2H)，3.25(t，J＝8.4Hz，3H)，1.71-1.61(m，2H)，1.23(t，J＝8.2Hz，9H)，0.59(t，J＝8.4Hz，2H)。
13C NMR (75MHz, CDCl
3): δ 70.9,70.6, and 70.1,63.0,53.9,51.3,17.9,15.5,8.0; MS m/z (%) 323 (100), 413 (M
+, 22.23); The ultimate analysis calculated value, C
18H
40O
8Si:C, 52.40; H, 9.77; Measured value: C, 52.62; H, 9.65.
Embodiment 3
(3) preparation of silicoorganic compound 3:
Operate as follows: Platinic chloride (0.5mol%) adds phenyl-allyl group-tetraethylene glycol (0.1mol), triethoxysilicane hydrogen (0.3mol), stirring at room 1 day 180 ℃ of vacuum-dryings 2 hours.Steam and remove excessive triethoxysilicane hydrogen, the vacuum pump decompression, 178 ℃ steam colourless liquid, obtain product 32.8g.
1H?NMR(300MHz，CDCl
3)：δ6.90-6.76(m，5H)，4.20(t，J＝6.9Hz，2H)，3.79(q，J＝7.2Hz，6H)，3.64-3.43(m，16H)，1.70-1.64(m，2H)，1.19-1.14((t，J＝7.2Hz，9H)，0.69(t，J＝8.4Hz，2H)。
13C NMR (75MHz, CDCl
3): δ 158.8,129.1, and 120.1,114.2,73.4,70.9,70.6,70.5,51.3,17.9,15.5,14.7,8.0; MS m/z (%) 385 (100), 475 (M
+, 22.54); The ultimate analysis calculated value, C
23H
42O
8Si:C, 58.20; H, 8.92; Measured value: C, 58.45; H, 8.70.
Embodiment 4
(4) preparation of silicoorganic compound 4:
Operate as follows: Platinic chloride (0.5mol%) adds ethyl-allyl group-triethylene glycol ether (0.1mol), trimethoxy silicon hydrogen (0.3mol), stirring at room 1 day 180 ℃ of vacuum-dryings 2 hours.Steam and remove excessive trimethoxy silicon hydrogen, the vacuum pump decompression, 169 ℃ steam colourless liquid, obtain product 28.6g.
1H?NMR(300MHz，CDCl
3)：δ3.74(q，J＝7.2Hz，6H)，3.64-3.43(m，14H)，3.38(t，J＝6.9Hz，2H)，1.70-1.56(m，2H)，1.17-1.10(m，12H)，0.58(t，J＝8.4Hz，2H)。
13C NMR (75MHz, CDCl
3): δ 73.4,70.9, and 70.6,70.1,63.0,51.3,17.9,15.5,14.7,8.0; MS m/z (%) 293 (100), 383 (M
+, 53.21); The ultimate analysis calculated value, C
19H
42O
8Si:C, 53.37; H, 10.01; Measured value: C, 53.55; H, 9.73.
Embodiment 5
(5) preparation of silicoorganic compound 5:
Operate as follows: Platinic chloride (0.5mol%) adds phenyl-allyl group-triethylene glycol ether (0.1mol), triethoxysilicane hydrogen (0.3mol), stirring at room 1 day 180 ℃ of vacuum-dryings 2 hours.Steam and remove excessive triethoxysilicane hydrogen, the vacuum pump decompression, 178 ℃ steam colourless liquid, obtain product 32.8 g.
1H?NMR(300MHz，CDCl
3)：δ6.90-6.76(m，5H)，4.20(t，J＝6.9Hz，2H)，3.79(q，J＝7.2Hz，6H)，3.64-3.43(m，12H)，1.70-1.64(m，2H)，1.19-1.14((t，J＝7.2Hz，9H)，0.69(t，J＝8.4Hz，2H)。
13C NMR (75MHz, CDCl
3): δ 158.8,129.1, and 120.1,114.2,73.4,70.9,70.6,70.5,51.3,17.9,15.5,14.7,8.0; MS m/z (%) 341 (100), 431 (M
+, 32.22); The ultimate analysis calculated value, C
23H
42O
8Si:C, 58.58; H, 8.89; Measured value: C, 58.29; H, 8.92.
Embodiment 6
(6) preparation of the mesoporous silicon material of usefulness organosilicon 1 modification:
Operate as follows: mesoporous material (SBA-15) 13.0g that handled with alcohol reflux places the 100ml three-necked bottle, 120 ℃ of vacuum-drying 3 hours.After the cooling, add toluene (60ml) and organosilicon 1 (9.6g), 110 ℃ were refluxed 6 hours.Be spin-dried for solvent, 150 ℃ of vacuum-dryings 12 hours, obtain white powder then.Washing with alcohol 3 times is dried the mesoporous material that obtains surface modification in the air.Ultimate analysis, C content are 15.42%, and organosilicon content is 1.0mmol/g.
Embodiment 7
(7) preparation of the mesoporous silicon material of usefulness organosilicon 2 modifications:
Operate as follows: mesoporous material (SBA-15) 10.0g that handled with alcohol reflux places the 100ml three-necked bottle, 120 ℃ of vacuum-drying 3 hours.After the cooling, add toluene (60ml) and organosilicon 1 (8.0g), 110 ℃ were refluxed 6 hours.Be spin-dried for solvent, 150 ℃ of vacuum-dryings 12 hours, obtain white powder then.Washing with alcohol 3 times is dried the mesoporous material that obtains surface modification in the air.Ultimate analysis, C content are 14.93%, and organosilicon content is 1.0mmol/g.
Embodiment 8
(8) preparation of the mesoporous silicon material of usefulness organosilicon 2 modifications:
Operate as follows: mesoporous material (SBA-15) 13.0g that handled with alcohol reflux places the 100ml three-necked bottle, 120 ℃ of vacuum-drying 3 hours.After the cooling, add toluene (60ml) and organosilicon 5 (9.0g), 110 ℃ were refluxed 6 hours.Be spin-dried for solvent, 150 ℃ of vacuum-dryings 12 hours, obtain white powder then.Washing with alcohol 3 times is dried the mesoporous material that obtains surface modification in the air.Ultimate analysis, C content are 16.23%, and organosilicon content is 0.9mmol/g.
Claims (8)
1. organosilicon containing carbon-oxygen-ether linkage compound, its structural formula is as follows:
2. the synthetic method of an organosilicon containing carbon-oxygen-ether linkage compound as claimed in claim 1 is characterized in that by following method synthetic: under-78～70 ℃ of temperature of organic solvent neutralization, incite somebody to action
HSiOR
1OR
2OR
3Obtaining structural formula in 0.5～48 hour with catalyst reaction is
The organosilicon containing carbon-oxygen-ether linkage compound, wherein,
HSiOR
1OR
2OR
3With the mol ratio of catalyzer be 1: 2～100: 0.001～10.0; Catalyzer is Platinic chloride or acetylacetone based rhodium.
3. the synthetic method of an organosilicon containing carbon-oxygen-ether linkage compound as claimed in claim 2 is characterized in that
In the described method
HSiOR
1OR
2OR
3With the mol ratio of catalyzer be 1: 2.2～30: 0.001～0.20.
4. organosilicon containing carbon-oxygen-ether linkage application of compound as claimed in claim 1, it is characterized in that the grafting of described organosilicon containing carbon-oxygen-ether linkage compound carries out modification to organosilicon material surface to organosilicon material, wherein, described organosilicon material is that to be 2.0～50nm, mesoporous material crystallographic system be two dimension cube, two dimension six sides, three-dimensional cubic or three-dimensional six sides' mesoporous material to mesopore orbit.
5. organosilicon containing carbon-oxygen-ether linkage application of compound as claimed in claim 4 is characterized in that described mesoporous material is a SiO 2 mesoporous materials.
6. organosilicon containing carbon-oxygen-ether linkage application of compound as claimed in claim 4, it is characterized in that the grafting of described organosilicon containing carbon-oxygen-ether linkage compound is in organic solvent to the organosilicon material surface, mesoporous material and carbon oxygen-ether linkage silicoorganic compound were obtained the organic-silicon-modified silicon materials of carbon oxygen-ether linkage in 2～48 hours 20～200 ℃ of thermotonuses, described mesoporous material is as described in the claim 4, and carbon oxygen-ether linkage silicoorganic compound according to claim 1.
7. organosilicon containing carbon-oxygen-ether linkage application of compound as claimed in claim 6 is characterized in that the element silicon mol ratio of described mesoporous material and carbon oxygen-ether linkage silicoorganic compound is 10～300: 1.
8. organosilicon containing carbon-oxygen-ether linkage application of compound as claimed in claim 6, it is characterized in that described organic solvent is normal hexane, hexanaphthene, toluene, tetrahydrofuran (THF), methylene dichloride, dimethyl sulfoxide (DMSO), N, dinethylformamide, 1,4-dioxane, acetone, ether or acetonitrile.
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