- One-step, acid-mediated method for modification of glass surfaces with N-hydroxysuccinimide esters and its application to the construction of microarrays for studies of biomolecular interactions
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Microarray technologies have received considerable attention owing to the fact that they serve as powerful tools for the high-throughput analysis of biomolecular interactions and the identification of bioactive substances that bind to biomolecules. Most of the current methods used to construct microarrays rely on the immobilization of substances on properly derivatized surfaces. Among various functional groups used for this purpose, the N-hydroxysuccinimide (NHS) ester group has been largely employed because it can be readily reacted with amine or hydrazide functionalities in substances of interest. However, the NHS ester group is usually introduced onto the surface of a glass slide by employing inconvenient and time-consuming multistep processes. In recent studies, we have developed an efficient, single step method for derivatization of glass surfaces with NHS ester groups that takes advantage of an acid-mediated reaction of NHS ester functionalized dimethallylsilanes with silanols on the glass surface. Conditions for the surface modification procedure that utilize TfOH rather than Sc(OTf)3 were found to be superior. Protein and RNA-binding experiments show that glass surfaces modified by employing this method are suitable for efficient immobilization of various substances that are appended by amine, hydrazide, and alcohol functionalities. The microarrays, generated in this way, are applicable to procedures for rapid analysis of protein-protein, protein-glycan, protein-small molecule, and peptide-RNA interactions, as well as for profiling enzyme activities. The newly developed acid-mediated, glass surface modification method should be generally applicable to the preparation of various functional group-modified surfaces.
- Park, Sungjin,Pai, Jaeyoung,Han, Eun-Hee,Jun, Chul-Ho,Shin, Injae
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Read Online
- Method for removing methyldichlorosilane and silicon tetrachloride impurities in trimethyl chlorosilane
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The invention relates to a method for removing methyldichlorosilane and silicon tetrachloride impurities in trimethyl chlorosilane, which comprises a hydrosilylation reaction, a partial esterification reaction and a complete esterification reaction. Firstly, a mixture of trimethylsilyl chloride containing methyldichlorosilane and silicon tetrachloride impurities is added to a reactor for hydrosilylation reaction, and the reaction product enters a separation system. The silicon tetrachloride in the mixture is partially esterified and reacted by adding the low-carbon alcohol as an esterifying agent, and the reaction product enters a separation system. Finally, the partially esterified product is further fully esterified to valuable tetraalkoxy silicon products. The high-efficiency recycling of trimethylchlorosilane is realized, and high-value utilization is also realized.
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Paragraph 0051-0054; 0062
(2021/08/25)
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- A magnetically recyclable superparamagnetic silica supported Pt nanocatalyst through a multi-carboxyl linker: Synthesis, characterization, and applications in alkene hydrosilylation
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To simplify separation procedures, improve the reusability and decrease the loss of Pt, two Pt catalysts anchored on superparamagnetic silica (Fe3O4@SiO2-EDTA@Pt and Fe3O4@SiO2-DTPA@Pt) were prepared for the first time. The stable magnetic properties made them easily recyclable using a magnet rather than filtration, decantation or centrifugation. After 12 catalytic runs for both 30-50 nm Pt catalysts, the yield of 1-heptylmethyldichlorosilane was still up to 90%. The average loss of Pt in each reaction was only 0.87% for Fe3O4@SiO2-EDTA@Pt and 0.66% for Fe3O4@SiO2-DTPA@Pt owing to the strong interaction between Pt and carboxyl. The unprecedented activity and selectivity of the two Pt nanoparticle catalysts were observed in the hydrosilylation of alkenes. The turnover number in the reaction between 1-hexene and methyldichlorosilane using 5 × 10-8 mol of the Pt approached 662733 for Fe3O4@SiO2-EDTA@Pt and 579947 for Fe3O4@SiO2-DTPA@Pt over 12 h. The corresponding hydrosilylation products in excellent yields were obtained when we employed a broad range of alkenes as substrates, including 5 isomerous hexenes and 14 important industry raw materials. Fe3O4@SiO2-DTPA@Pt showed a better activity. They have potential for catalyzing more reactions and replacing the current homogeneous Pt catalysts in industry.
- Li, Laiming,Li, Youxin,Yan, Jincong,Cao, Hang,Shao, Dongyun,Bao, James J.
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p. 12696 - 12709
(2019/05/06)
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- Production method of chloropropylmethyldichlorosilane
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The invention relates to a production method of chloropropylmethyldichlorosilane and belongs to the field of organic chemistry. The production method comprises the following steps: firstly, enabling chloroplatinic acid to react with isopropanol, acetic acid, phenyl silicone oil and the like; secondly, neutralizing by adopting sodium acetate, enabling part of the isopropanol complexed with platinum to be completely substituted under the alkaline conditions, thereby enabling a ligand of a catalyst to be directly substituted with the acetic acid and the phenyl silicone oil; after substitution, by taking tributylamine as a promoter, avoiding the inactivation of the catalyst in the addition reaction; during synthesis, reacting by adopting mixed feeding, adding at low temperature, and raising the temperature for continuous reaction after most reaction is finished; after the reaction is finished, completely distilling low boiling point products at normal pressure, and then distilling foreshot under vacuum conditions; after the foreshot are distilled, obtaining a chloropropylmethyldichlorosilane product with the content of 99.5 percent or above. The synthesized product disclosed by the invention has the advantages of high yield, low capacity, fewer byproducts, low requirement on equipment, and the like; in addition, the production method is relatively-simple in industrial production.
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Paragraph 0015; 0016
(2017/02/17)
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- Mechanistic insights into the hydrosilylation of allyl compounds - Evidence for different coexisting reaction pathways
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The hydrosilylation of allyl compounds is often accompanied by the formation of high amounts of byproducts. The formation processes have not been fully understood so far. In this work, the allyl hydrosilylation mechanism is investigated in detail and experimental and theoretical evidence for multiple, coexisting reaction pathways is provided. Based on earlier reports and the observations during an extensive catalytic study, different pathways, leading to the observed byproducts, were identified and proven by labeling experiments and DFT calculations. Oxidative addition of the silane and the insertion of the allyl compound into the Pt-H bond turned out to be the crucial, selectivity-determining steps within the catalytic cycle. Based on these findings, it should be possible to systematically influence these steps and pave the way to a rational and straightforward design of more selective catalysts.
- Gigler, Peter,Drees, Markus,Riener, Korbinian,Bechlars, Bettina,Herrmann, Wolfgang A.,Kuehn, Fritz E.
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- METHOD FOR HYDROSILYLATION USING A PLATINUM CATALYST
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The selectivity of hydrosilylation of unsaturated organic compounds by Si—H functional organosilicon compounds is improved by use of a silyl polyphosphate ester in conjunction with a platinum hydrosilylation catalyst.
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Page/Page column 4
(2013/02/27)
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- METHOD FOR HYDROSILYLATING
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Minimization of byproducts in hydrosilylation reactions is achieved by use of a catalyst system which contains a platinum (O) complex catalyst and an oranic amine oxide and/or hydrate thereof.
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Page/Page column 5
(2012/04/11)
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- Surface Modified Inorganic Material and Producing Method Thereof
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A surface-modified inorganic material and a preparation method thereof. A surface-modified inorganic material is provided which is obtained by allowing an organosilane compound having allyl or an allyl derivative to react with an inorganic material, particularly solid silica or ITO glass, in the presence of an acid and an organic solvent, to introduce an organic group into the inorganic material even at room temperature, as well as a preparation method thereof. The invention can effectively introduce the organic group into the inorganic material even at room temperature, and thus is very effective in introducing compounds having a thermally sensitive functional group, for example, natural compounds or proteins. It is possible to introduce various organic groups into an inorganic material and to separate and purify organic molecule-bonded organosilane compounds using a silica gel column to effectively bond them to inorganic materials. Accordingly, the invention is very useful in the chemical industry.
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Page/Page column 7; 8
(2009/10/31)
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- Continuous Preparation of Organosilanes
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The invention relates to a process for the continuous preparation of organosilanes in a reactive distillation column, wherein a homogenous hydrosilylation catalyst is introduced into the column.
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Page/Page column 4-5
(2008/06/13)
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- Sc(OTf)3-mediated silylation of hydroxy functional groups on a solid surface: A catalytic grafting method operating at room temperature
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(Chemical Equation Presented) Surface paradise: Facile catalytic post-grafting of the surface of glass or indium tin oxide (ITO, see picture) with a variety of functional groups has been achieved. Methallylsilanes serve as the grafting reagent and the surfaces show remarkable chemical stability.
- Yeon, Ye-Rim,Park, Young Jun,Lee, Ji-Sung,Park, Jung-Woo,Kang, Sin-Gun,Jun, Chul-Ho
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p. 109 - 112
(2008/09/19)
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- SURFACE MODIFIED ORGANIC·INORGANIC HYBRID GLASS, PROTECTING GROUP INDUCED ALCOHOL OR ITS DERIVATIVE AND PRODUCING METHOD THEREOF
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Disclosed are a protected alcohol or derivative thereof, a surface- modified organic-inorganic hybrid glass, and preparation methods thereof. More specifically, disclosed are a protected alcohol or derivative thereof and a surface-modified organic-inorganic hybrid glass, which are prepared by allowing a silane compound, having vinyl or a vinyl derivative, to react with an alcohol or derivative thereof or with an organic-inorganic hybrid glass, in the presence of an acid catalyst, a transition metal catalyst and an organic solvent, so as to introduce an organic group thereto even at room temperature, as well as preparation methods thereof. The disclosed invention allows a functional group to be effectively introduced into alcohol or a derivative thereof or into an organic-inorganic hybrid glass, not only high temperatures but also room temperature, and thus is highly effective in introducing compounds having a thermally sensitive functional group, for example, natural compounds or proteins. Also, the invention makes it possible to introduce various organic groups and to separate and purify organic macromolecule-bonded organosilane compounds using a silica gel column so as to effectively introduce large organic functional groups to inorganic materials. Accordingly, the invention is highly useful in the chemical industry.
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Page/Page column 35
(2010/11/28)
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- Continuous hydrosilylation process
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Continuous hydrosilylation of compounds (A) bearing C—C multiple bonds by means of silicon compounds (B) having Si—H groups, in which the reaction components (A) and (B) are reacted continuously in an integrated loop-tube reactor, with reaction mixture being conveyed from the tube into the loop and back again so that a section of the tube is part of the loop circuit, provides a highly controllable reaction process with high product yields.
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Page/Page column 4-5
(2008/06/13)
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- New multifunctional polar silanes for polymer modification
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New trifunctional carbosilanes containing hydroxy, alkenyl, chloro and cyano groups have been synthesized in good yields. A useful synthesis of these polymer precursors from dichlorosilanes was developed after it was found that hydrosilation of functionalized alkenes by a dihydrosilane, 2-cyanoethylmethyldihydrosilane, failed to give the expected dialkylsilanes.
- Hewitt, David G.,Jing, Lin
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p. 267 - 272
(2007/10/03)
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- Reaction of bis(trifluoromethyl)amino-oxyl with alkylchlorosilanes and allyldichloro(methyl)silane and of perfluoro-2,5-diazahexane 2,5-dioxyl with vinylsilanes and hydrolysis of the products
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Treatment of the silanes MeSiHCl2, Me2SiHCl and EtSiMeCl2 with the oxyl (CF3)2NO(.) (1) gives the substitution products (CF3)2NOSiMeCl2 (4) and (CF3)2NOSiMe2Cl (5), and a mixture of (CF3)2NOCHMeSiMeCl2 (8) and (CF3)2NOCH2CH2SiMeCl2 (9) (ratio 20:37), respectively, while the silane EtSiMe2Cl affords mainly the ester (CF3)2NO2CMe (7).Attack of oxyl 1 on the silane CH2=CHCH2SiMeCl2 results in both allylic substitution and addition to give the compounds CH2=CHCH(SiMeCl2)ON(CF3)2 (14) and (CF3)2NOCH2CH(CH2SiMeCl2)ON(CF3)2 (15) (ratio 56:40).Reaction of the dioxyl (.)ON(CF3)CF2CF2N(CF3)O(.) (2) with the vinylsilanes CH2=CHSiX3 (X3 = Me3, Cl3, MeCl2) gives mainly 1:1 copolymers n (17), although the cyclic 1:1 adduct (18) is also formed in low yield.Hydrolysis of the silanes 15, (CF3)2NOCH2CH(SiMeCl2)ON(CF3)2 (19a) and (CF3)2NOCH2CH(SiCl3)ON(CF3)2 (19b) affords the corresponding polysiloxanes 24 and 25, and the polysilsesquioxane 26, respectively; the polymers 25 and 26 undergo rearrangement of the type -CH(Si)ON(CF3)2 --> -CH(OSi)N(CF3)2 on storage.The 1:1 copolymers 17b (X3 = MeCl2) and 17c (X3 = Cl3) are also hydrolysed to the corresponding siloxane and silsesquioxane polymers.In contrast, hydrolysis of the compounds 4,5 and (CF3)2NOCH2CH(OSiX3)N(CF3)2 (20a; X3 = MeCl2) and (20b; X3 = Cl3) results in Si-O bond cleavage.
- Tipping, Anthony E.,Yadav, Rajendraprasad B.
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- Packing for use in resolution
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The packing for use in resolution proposed for the liquid chromatography for particularly the opti-cal resolution of racemic compounds is prepared by reacting a silica gel carrier with a so-called silane treating agent to introduce a spacer part therein and chemically bonding it with a copper salt of a carboxylic or thiocarboxylic acid selected from the group consisting of optically active D- and L-2--acetizinecaroxylic acid, proline, hydroxyproline and allohydroxyproline. The steric bulkiness, the distance between the silica gel and the optically active group and the degree of hydrophobicity are specified so as to obtain an excellent resolving power.
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- SILAETHENE I. DARSTELLUNG UND CHARAKTERISIERUNG VON MONOSILACYCLOBUTANEN
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Monosilacyclobutanes of the type RR' are prepared by ring closure reactions of 3-halopropylhalosilanes and by substitution of SiCl containing silacyclobutane rings with organometallic reagents (RMgX, LiR, NaCp).Under optimal experimental conditions yields between 50 and 95percent can be obtained by both procedures.Characterization of the compounds is accomplished by analytical (C, H, N) and NMR, IR and mass spectroscopic investigations.
- Auner, N.,Grobe, J.
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