WO1993016085A1 - Procede de fabrication de tetraalcoxysilanes de couleur claire - Google Patents
Procede de fabrication de tetraalcoxysilanes de couleur claire Download PDFInfo
- Publication number
- WO1993016085A1 WO1993016085A1 PCT/EP1993/000208 EP9300208W WO9316085A1 WO 1993016085 A1 WO1993016085 A1 WO 1993016085A1 EP 9300208 W EP9300208 W EP 9300208W WO 9316085 A1 WO9316085 A1 WO 9316085A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acidic
- bleaching
- tetraalkoxysilanes
- tetramethoxy
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000004061 bleaching Methods 0.000 claims abstract description 36
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 230000002378 acidificating effect Effects 0.000 claims description 33
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
- 150000001768 cations Chemical class 0.000 claims description 16
- 210000002741 palatine tonsil Anatomy 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 238000005809 transesterification reaction Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical group CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salts Chemical class 0.000 claims 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical class CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000005341 cation exchange Methods 0.000 abstract 1
- 239000011973 solid acid Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000005049 silicon tetrachloride Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Natural products CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- DEMBLPGWNXUBIQ-UHFFFAOYSA-N 2-dodecylhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCC(CO)CCCCCCCCCCCC DEMBLPGWNXUBIQ-UHFFFAOYSA-N 0.000 description 1
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N n-octadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/04—Esters of silicic acids
Definitions
- the invention is in the field of tetraalkoxysilanes and relates to a process for the preparation of light-colored tetraalkoxysilanes by transesterification of tetramethoxy- or ethoxysilanes with primary higher alcohols in the presence of basic catalysts and subsequent neutralization and bleaching using solid acidic bleaching earth and cation exchangers.
- Tetraalkoxysilanes which are also called orthosilicic acid esters and correspond to the general formula Si (0R) 4, are known from the prior art.
- US Pat. No. 2643263 describes silanes of branched alcohols having 8 to 14 carbon atoms, which are accessible either by reacting silicon tetrachloride or by transesterifying tetraethoxysilane with the corresponding higher alcohols.
- the production via silicon tetrachloride has the disadvantage that the higher acidity of the reaction mixture leads to the undesired hydrolysis of the product.
- the transesterification for the preparation of the tetraalkoxysilanes is preferred in principle. Since the transesterification is a sequence of VOB 4 equilibrium reactions, the use of catalysts is absolutely necessary. An overview of catalysts that can be used is given by H. Steinmann, G. Tschernko and H. Hamann, Z. Chem. Vol. 17, pages 89-92, 1977. Accordingly, both acids, such as hydrochloric acid, sulfuric acid and p-toluenesulfonic acid, and bases, such as alkali metal hydroxides or alcohols, can be used.
- acids such as hydrochloric acid, sulfuric acid and p-toluenesulfonic acid
- bases such as alkali metal hydroxides or alcohols
- the object of the present invention was to develop a process which delivers light-colored tetraalkoxysilanes in as few process steps as possible.
- the base-catalyzed transesterification known per se and the dark-colored tetraalkoxysilanes resulting therefrom should be assumed.
- the processing of the tetraalkoxysilanes should deliver products that are as pure as possible in a short time.
- the present invention relates to a process for the preparation of light-colored tetraalkoxysilanes by transesterification of tetramethoxy or tetraethoxysilanes with primary alcohols in the presence of basic catalysts, characterized in that a) tetramethoxy or tetraethoxysilanes with primary alcohols having 3 to 38 carbon atoms in molar amounts of 1: 4 to 1: 6 in the presence of 0.01 to 0.1 mol% of alcoholate - based on tetramethoxy or tetraethoxysilane - transesterified with constant removal of the methanol or ethanol formed and then the reaction mixture with b) solid acidic bleaching earth or solid acidic cation exchangers and acidic bleaching earth are added, mixed and filtered off.
- Tetraethoxy and tetra ethoxysilane are commercially available products that are accessible from tetrachlorosilane and methanol or ethanol.
- Suitable alcohols are aliphatic saturated and / or unsaturated alcohols, as can be obtained from natural oils and fats or after oxo synthesis, as are the Guerbet alcohols branched in the ⁇ -position, obtainable by the Guerbet process.
- Suitable Guerbet alcohols are those with 12 to 38 carbon atoms, such as 2-n-butyl-n-octanol, 2-n-hepty-n-undecanol, 2-n-octyl-n-dodecanol and 2-n-dodecyl- n-hexadecanol.
- the transesterification is preferably carried out in a molar ratio of tetra methoxy or tetraethoxysilane to the primary alcohols of 1: 4.2 to 1: 4.8.
- Alkali salts of lower alcohols having 1 to 4 carbon atoms, preferably sodium methoxide, are preferably present as basic catalysts.
- the catalysts and the amounts used correspond to the known prior art.
- the tetramethoxy or ethoxysilanes, primary alcohols and the basic catalyst are heated together, the methanol and / or ethanol formed being removed continuously.
- the transesterification is preferably carried out at temperatures in the range from 80 to 250 ° C., with slow heating at a constant temperature heating rate, in particular from 0.1 to 5 ° C. per minute, being recommended.
- the reaction is preferably carried out until - in relation to the amount of methanol or affiliated abdesti Eth 'anol - an environmental of esterification of 50 to 100%, preferably 85 to 95% is achieved.
- the degree of esterification is a percentage which results from the quotient of the actual amount of alcohol distilled off and the theoretically achievable amount of alcohol.
- the tetraalkoxysilanes resulting from the transesterification are dark brown products that have to be worked up.
- the workup includes both the neutralization of the bakery alcoholate catalyst present in the reaction mixture and the bleaching.
- Solid acidic bleaching earths or solid acidic cation exchangers can be used for neutralization.
- the term acidic bleaching earth in the sense of the invention encompasses both the activation of the bleaching earth with acids and the fact that the aqueous suspensions of the bleaching earth have a pH below 6.
- Acidic bleaching earths are particularly preferred which, as an aqueous suspension, have a pH between 1 and 4, since they have a higher exchange capacity for neutralization.
- Suitable solid acidic bleaching earths are, for example, specially prepared bleaching earths of the montmorillonite type, such as those from Süd-Chemie AG, Kunststoff under the name K catalysts, for example KP 10, KSF, KSF / 0, KA / 0 or under the name Tonsil, for example Tonsil COG, Tonsil Optimum FF, Tonsil Standard, Tonsil Supreme or Tonsil ACC.
- K catalysts for example KP 10, KSF, KSF / 0, KA / 0
- Tonsil for example Tonsil COG, Tonsil Optimum FF, Tonsil Standard, Tonsil Supreme or Tonsil ACC.
- Acidic cation exchangers based on synthetic resin ion exchangers are also very suitable. These products represent highly polymeric spatial networks made of carbon chains in a gel structure, which contain -S03 "groups or SO3 ⁇ and --0" groups as charge-carrying groups.
- these are cation exchangers based on polystyrene sulfonic acid resins or phenolsulfonic acid resins, which are known, for example, under the following trade names: Lewatit S10 ⁇ ( R ), Lewatit SC 102 ( R ), Lewatit SC 108 ( R ), Lewatit SPC 118 ( R ), Lewatit SP 108 ⁇ ( R ), Lewatit SP 12 ⁇ ( R ), Lewatit S 115 ( R ), Amberlite IR 12 ⁇ ( R ), Amberlite IR 20 ⁇ ( R ), A berlyst l ⁇ ( R ) ( Permutit RS 12 ⁇ ( R ), Per utit RSP 12 ⁇ ( R ), Dowex 5 ⁇ ( R ), Wofatit F ( R ), Wofatit F ( R ), Wofatit D ( R ), Wofatit KPS 20 ⁇ ( R ), Duolite C-3 ( R ), Duolite C-l ⁇ ( R ), Duolite C-
- the acidic bleaching earths and cation exchangers are preferably used free of water or with the smallest possible amount of water. This is not a problem for acidic bleaching earths, since they are commercially available as a solid with only a small amount of water. In contrast, the acidic cation exchangers of the type described must be swollen with water in order to activate the exchange capacity. The water not required for hydration can now be minimized by drying after swelling.
- the amount of acidic bleaching earth or cation exchanger required depends strongly on their (proton) capacity for the exchange and the amount of alcoholate used. Random checks of the pH value quickly reveal the quantities required.
- the amount is preferably for neutralization per mole of alcoholate in the range of 2 to 3 kg of the acid bleaching earth Tonsil or 0.8 to 3 kg of acidic cation exchanger.
- the acidic bleaching earths described must also be added for bleaching, preferably in amounts of 1 to 10% by weight, based on the reaction mixture.
- treatment with activated carbon can be carried out in a known manner.
- the treatment with the solid bleaching earth or the cation exchangers is carried out by adding them alone or in a mixture or in succession to the reaction mixture and mixing them together for at least 30 minutes, preferably 1 to 2 hours, and then filtering them off.
- the dark brown reaction mixture cooled to 50 ° C., is mixed with 20 g of acidic bleaching earth (Tonsil R COG 15/30 esh from Südchemie) and with 1 g of activated carbon and stirred for 2 hours at 70 ° C. in a water jet vacuum.
- Example 2 Analogously to Example 2, 22.8 g (0.15 mol) of tetramethoxysilane and 0.135 g of sodium methoxide (as a methanol solution) were added to 164 g of the technical 2-hexyl decanol. The reaction mixture was treated with 9 g of the acid bleaching clay Tonsil COG 15/30 mesh; Südchemie, offset and worked up analogously to Example 1.
- Table 1 shows whether neutralization was achieved under the specified conditions and the color of the product. % By weight relate to crude product. Table 1 Neutralization and color
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
L'invention a trait au domaine des tétraalcoxysilanes et concerne un procédé de fabrication de tétraalcoxysilanes par transestérification de tétraméthoxy- ou éthoxysilanes avec des alcools primaires supérieurs en présence de catalyseurs basiques, puis par neutralisation et décoloration au moyen de terres décolorantes acides compactes et d'échangeurs de cations.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4203352.7 | 1992-02-06 | ||
| DE4203352A DE4203352A1 (de) | 1992-02-06 | 1992-02-06 | Verfahren zur herstellung von hellfarbigen tetraalkoxysilanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993016085A1 true WO1993016085A1 (fr) | 1993-08-19 |
Family
ID=6451051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1993/000208 WO1993016085A1 (fr) | 1992-02-06 | 1993-01-29 | Procede de fabrication de tetraalcoxysilanes de couleur claire |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE4203352A1 (fr) |
| WO (1) | WO1993016085A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998003514A1 (fr) * | 1996-07-23 | 1998-01-29 | Wacker-Chemie Gmbh | Procede de preparation d'alcoxysilanes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2643263A (en) * | 1950-09-22 | 1953-06-23 | California Research Corp | Higher secondary-alkyl orthosilicates |
| US2814634A (en) * | 1952-10-16 | 1957-11-26 | Pierce John B Foundation | Process of making silicates |
| EP0223210A2 (fr) * | 1985-11-14 | 1987-05-27 | Toray Silicone Co., Ltd. | Méthode de purification d'alcoxysilanes |
-
1992
- 1992-02-06 DE DE4203352A patent/DE4203352A1/de not_active Withdrawn
-
1993
- 1993-01-29 WO PCT/EP1993/000208 patent/WO1993016085A1/fr active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2643263A (en) * | 1950-09-22 | 1953-06-23 | California Research Corp | Higher secondary-alkyl orthosilicates |
| US2814634A (en) * | 1952-10-16 | 1957-11-26 | Pierce John B Foundation | Process of making silicates |
| EP0223210A2 (fr) * | 1985-11-14 | 1987-05-27 | Toray Silicone Co., Ltd. | Méthode de purification d'alcoxysilanes |
Non-Patent Citations (1)
| Title |
|---|
| BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN Bd. 61, Nr. 11, 1988, Seiten 4087 - 4092 HASEGAWA, I. ET AL. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998003514A1 (fr) * | 1996-07-23 | 1998-01-29 | Wacker-Chemie Gmbh | Procede de preparation d'alcoxysilanes |
| US6005132A (en) * | 1996-07-23 | 1999-12-21 | Wacker-Chemie Gmbh | Method of preparing alkoxy silanes |
| JP3204987B2 (ja) | 1996-07-23 | 2001-09-04 | ワツカー―ケミー ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | アルコキシシランの製法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4203352A1 (de) | 1993-08-12 |
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