Process for producing sulphur-containing organosilicon compounds

专利摘要:
1518560 Preparing bis(silylalkyl) polysulphides DEUTSCHE GOLD-UND SILBERSCHEIDEANSTALT 23 Sept 1976 [24 Sept 1975] 39481/76 Heading C3S Bis(organo - oxysilylorgano) polysulphides Z-Alk-Sx-Alk-Z, wherein each Z is -SiR2OR<1>, -SiR(OR<1>)2, -Si(OR<1>)3 or -Si(OC2H4)3N, each R being a C1-8 alkyl, a C5-8 cycloalkyl, a benzyl, or an optionally methyl-, ethyl-, or chloro-substituted phenyl group, and each R<1> being a C1-8 alkyl, a methoxyethyl, a C5-8 cycloalkyl, a phenyl or a benzyl group, Alk is a C1-10 alkylene group, optionally interrupted by one or two -O-, -S- or -NH-, and x is 2-6, are prepared by reaction of a silane Y-Alk-Hal, wherein each Y is -SiR2Hal, -SiRHal2, or -SiHal3, Hal being halogen, with at least one compound R<1>OH is at least the stoichiometric amount, and in the case of the product (R<1>O)3Si-Alk- Hal, optionally reacting it further with triethanolamine to form the silatrane, then reacting the product with a hydrogen sulphide MSH, where M is NH4, an alkali metal atom, or half an alkaline earth metal atom, and elemental sulphur, preferably in an inert organic solvent. In the Examples 10 moles of ClCH2CH2CH2SiCl3 or ClCH2CH2SiCl3 are treated with a 5% excess of MeOH, EtOH or i-PrOH, the HCl produced is driven off, then more alcohol is added, as solvent, with 5, 10 or 15 moles of sulphur and 10 moles of NaSH; the products are bis(trialkoxysilyl-ethyl or -propyl) di-, tri- or tetra-sulphides. Uses: Adhesion promoters; intermediates.
公开号:SU900814A3
申请号:SU762402959
申请日:1976-09-24
公开日:1982-01-23
发明作者:Плетка Ханс-Дитер；Михель Рудольф
申请人:Дегусса, Аг., Формальс Ресслер (Фирма)；
IPC主号:

专利说明:

(5) METHOD FOR GETTING SERO-CONTAINING ORGANOMETRIC COMPOUNDS The invention relates to organosilicon chemistry, to an improved method. to obtain sulfur-containing silicon compounds of general formula Z-Alk-Sx-A1k-Z, / R where 2 is Si-R 4 VR. .OSHN CaHs; R CH, -Si-GCiH -N; OSG Nc alkoxy with C-Ce straight or branched hydrocarbon chain, cycloalkoxy phenoxy group; alkylene With -Cg; an integer from 2 to 5 which are used as additives to polymeric materials. A known method for producing these compounds by reacting mercaptoalkylsilane with elemental sulfur t13. The disadvantage of this method is the need to work with mercaptosil, which is relatively expensive and is obtained with a poor yield. The closest in technical essence to the present invention is a method for producing sulfur-containing organosilicon compounds of formula I by reacting an organosilane of the general formula Z-Aik-ha1, where Z, Alk as above, hal is a halogen with a sulfiding agent, namely alkali metal polysulfide, in a medium organic solvent at a temperature of from room temperature to boiling of the reaction mixture 2. The disadvantage of this method is the need to work with alkali metal polysulfides, taken in the form of solutions, the concentration of which should be strictly controlled by analytical methods in order to obtain the target product uniform and uniform in composition, i.e. in the specified method is difficult to maintain the desired ratio of reagents.
The aim of the invention is to simplify the process of obtaining soybean / gallantum of formula I.
This goal is achieved by using a mixture of hydrosulfide of the general formula MeSH, where Me is an alkali metal atom or ammonium ion, and elementary 1; (oh sulfur, taken in a molar ratio of 1: 0,, 0.
The elemental sulfur is preferably used in finely divided form, for example in the form of powdered sulfur. The hydrosulfide, to accelerate the reaction, is preferably used in the form of a powder. The reaction starts already at room temperature, after the components of the reaction have been brought into contact, and can then proceed as an exothermic reaction itself. It is more expedient, in order to reduce the overall reaction time, to operate at an elevated or increased temperature, which can rise up to the boiling point of the solvent or solvent mixture used. It is preferable to use an inert organic solvent with a not too high boiling point, in which the components of the reaction used can dissolve. Such solvents are, for example, dioxane, dimethylformadiide, tetrahydrofuran and, in particular, acetone as well as alcohols, primarily singing. lower aliphatic or cycloaliphatic alcohols and mixtures thereof.
Next, the reaction is carried out in the absence of air, water (moisture) in order to reduce or avoid the formation of by-products. You can, for example, work in a dry inert gas atmosphere, like nitrogen, or in a noble gas atmosphere. It is advisable to use hydrogen sulfide, which is formed by reaction with MeSH and elemental sulfur, as an inert gas. The excretion of hydrogen sulfide can be controlled by changing the temperature. The hydrosulfide can be added to the mixture through a simple gas-tight tank, CroMb addition, it is possible to carry out the reaction under reduced pressure (slightly elevated pressure is not equally excluded).
By the end of the reaction, the release of sulfur prenatal decreases. A known holding time after the reaction may be advantageous. At the end of the reaction, the reaction mixture is cooled under known conditions, filtered from the precipitated salt, and then the organic solvent is removed, preferably by distillation.
preferably under reduced pressure. The organosilicon compounds formed as final products under normal conditions cannot be distilled without decomposition. therefore
they are collected in a distillation tank and in most cases used without further purification. They can be used, for example, as valuable fittings (lrilipatel) or
reinforcing additives in rubber mixtures containing fillers. However, they also have valuable intermediates.
Example 1. In a three-necked flask with a capacity of 10 liters, equipped with a stirrer, an internal thermometer, a reflux condenser, and a device for feeding solids, are placed
2410-Zchloropropyltriethoxysilane in 400 g of ethanol and then 480 g of powdered sulfur and 5 HO g of sodium hydrosulfide are added to the prepared mixture. Slowly starting hydrogen sulfide release is accelerated by heating the reaction mixture to its boiling point. After completion of the reaction, the sodium chloride precipitated out is filtered off and excess alcohol is distilled off. The result is practically with a quantitative yield of bis- (3 triethoxysylpropyl) -tetrasulfide. Compound
characterized by NMR and IR spectrum and according to the elementary
analysis. one
Calculated, weight: 1 With 40,11; H, 84;
Si 10.42; S 23.65.
Found, weight: C 39.9b; H7.70;
Si 10.58; S23.65. Examples 2-44. Analogously to example 1, other organosilanes are obtained, the starting materials for the preparation of which and the analysis data are presented in the table. In this case, the reaction components are used in the indicated stoichiometric amounts, and the yield is almost quantitative.
Example 45. By analogy with example 1, first dissolve 3f62 to chloropropyltriethoxysilane in 6 kg
ethanol, and then 0.77 kg (obtained by passing dry NHj and alternately HjS to anhydrous di: ethyl ether at) and 0.72 kg of powdered sulfur are added in portions. When this happens, HjS is gradually released, and the reaction mixture is heated to boiling. After the reaction is complete, the precipitated ammonium chloride is filtered off from the reaction mixture and the solvent is removed. Bis- (3-triethoxysilylpropyl) -tetrasulfide, obtained practically with a quantitative yield, according to the elemental analysis contains,%: sulfur 23.31;
carbon 38.90; hydrogen 7g silicon 10.31;
Example C (, Carried out the synthesis in the example, but using 0, kg of powdered sulfur, a similar silane trisulfide is obtained in approximately equal yield with analytically determined sulfur content
B, 73% (18.9U), carbon kZ, (3.85%), hydrogen 8.05% (8.13%) and Femni 10.58% (10.8P).
The advantage of the proposed method in comparison with the known is the uniformly attained value of sulfur in the product of the method, when it comes from chlorine-free ethoxy-silane (Example 1), since the stoichiometry of the reaction is better controlled and observed.
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权利要求:
Claims (2)
[1]
2G 0) Z s a. 21 The claims of the method for preparing organosulfur-containing organium compounds of the general formula I Z-Alk-Sx-Alk-Z, where R R. OS, Nb -glts, -51 0СгНц-М; R € N3; Cj, Hj; Cj, H OCjH / R is an alkoxy with a straight or branched hydrocarbon chain, cycloalkoxy Cj-C or phenoxide; Alk - alkylene C s X - an integer from 2 to by reacting an organosilane of the general formula Z-Alk-hal, where Z and Alk as above, hal is a halogen, with a sulfiding agent in an organic solvent at a temperature from room temperature to boiling of the reaction mixture wherein, in order to simplify the process, a mixture of hydrosulfide of the general formula MeSH, where Me is an alkali metal atom or ammonium ion, and elemental sulfur, taken in a molar ratio of 1: 0, is used as the sulfiding agent. Sources of information taken into account in the examination 1.Patent of France NT 2260585 Cl. From 07 F 7/08, published 1975.
[2]
2. US Patent ff, class 2, published. 197 (prototype).

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同族专利:

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公开号 | 公开日

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US4072701A|1978-02-07|

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AR217631A1|1980-04-15|

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BE846519A|1977-03-23|

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CH621353A5|1981-01-30|

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ATA705976A|1977-12-15|

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JPS5253819A|1977-04-30|

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DD127161A5|1977-09-07|

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CA1080736A|1980-07-01|

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CS617076A2|1985-08-15|

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IT1121673B|1986-04-10|

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DK424476A|1977-03-25|

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GB1518560A|1978-07-19|

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AT344733B|1978-08-10|

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IL50544A|1980-03-31|

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DK143706C|1982-03-15|

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DK143706B|1981-09-28|

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ES451745A1|1977-08-16|

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ZA765745B|1977-08-31|

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NL186241C|1990-10-16|

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FR2325651B1|1979-06-08|

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DE2542534A1|1977-03-31|

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NL186241B|1990-05-16|

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DE2542534C3|1979-08-02|

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NL7610482A|1977-03-28|

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IL50544D0|1976-11-30|

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JPS5726599B2|1982-06-05|

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PL105436B1|1979-10-31|

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CS244652B2|1986-08-14|

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DE2542534B2|1978-11-30|

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FR2325651A1|1977-04-22|

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BR112019003052A2|2016-08-31|2019-05-21|Dynasol Elastómeros, S.A. De C.V.|processes for preparing main batches of rubber and silica|

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法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE2542534A|DE2542534C3|1975-09-24|1975-09-24|Process for the preparation of sulfur-containing organosilicon compounds|

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