DE1000817B - Process for the preparation of silyl mercaptans and silyl thioethers - Google Patents
Process for the preparation of silyl mercaptans and silyl thioethersInfo
- Publication number
- DE1000817B DE1000817B DEF16378A DEF0016378A DE1000817B DE 1000817 B DE1000817 B DE 1000817B DE F16378 A DEF16378 A DE F16378A DE F0016378 A DEF0016378 A DE F0016378A DE 1000817 B DE1000817 B DE 1000817B
- Authority
- DE
- Germany
- Prior art keywords
- silyl
- mercaptans
- thioethers
- preparation
- silanes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- FGEJJBGRIFKJTB-UHFFFAOYSA-N silylsulfanylsilane Chemical class [SiH3]S[SiH3] FGEJJBGRIFKJTB-UHFFFAOYSA-N 0.000 title claims description 5
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 7
- 150000004756 silanes Chemical class 0.000 claims description 4
- -1 vinylsilyl compounds Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical group Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von Silylmercaptanen und Silylthioäthern Silylmercaptane und Silylthioäther lassen sich bekanntermaßen herstellen durch Umsetzen von Sulfiden, Hydrosulfiden oder Mercaptiden der Alkalien oder Erdalkalien mit Alkylsilanen, die im Kohlenwasserstoffrest halogeniert sind. Dieses Herstellungsverfahren muß also den Umweg über die Halogenierung von Organosiliciumverbindungen gehen; es ist zweistufig und ergibt nur geringe Ausbeuten an silylsubstituierten Thioalkoholen und Thioäthern.Process for the preparation of silyl mercaptans and silyl thioethers As is known, silyl mercaptans and silyl thioethers can be prepared by reaction of sulfides, hydrosulfides or mercaptides of alkalis or alkaline earths with alkylsilanes, which are halogenated in the hydrocarbon radical. This manufacturing process must So take the detour via the halogenation of organosilicon compounds; it is two-stage and gives only low yields of silyl-substituted thioalcohols and thioethers.
Die unmittelbare Umsetzung von gesättigten aliphatischen oder von aromatischen Organohalogensilanen mit Schwefelwasserstoff gelingt zwar mit Hilfe von Halogenwasserstoffbindern, führt dann aber nicht zu Thioalkoholen, sondern zu cyclischen Polysilthianen, Verbindungen also, die den Schwefel an Silicium gebunden enthalten und die daher auch hydrolytisch leicht zersetzlich sind.The immediate implementation of saturated aliphatic or of aromatic organohalosilanes with hydrogen sulfide succeed with the help of hydrogen halide binders, but then does not lead to thioalcohols, but to cyclic polysilthianes, compounds that bind sulfur to silicon and which are therefore easily hydrolytically decomposable.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Silylmercaptanen und Silylthioäthern, das dadurch gekennzeichnet ist, daß Silane der allgemeinen Formel R Si X3, worin R einen organischen Rest, der eine Kohlenstoffdoppelbindung enthält, und X eine organische oder anorganische, hydrolysierbare oder nicht hydrolysierbare Gruppe bedeutet, mit Schwefelwasserstoff umgesetzt werden.The invention relates to a process for the preparation of silyl mercaptans and silyl thioethers, which is characterized in that silanes of the general Formula R Si X3, where R is an organic radical that has a carbon double bond contains, and X an organic or inorganic, hydrolyzable or non-hydrolyzable Group means to be reacted with hydrogen sulfide.
Diese Synthese verläuft mit guter Ausbeute unter Anlagerung eines H2 S-Moleküls an ein oder zwei Kohlenstoffdoppelbindungen und kann je nach Art des angewendeten Silanderivates unter atmosphärischem oder erhöhtem Druck durchgeführt werden. Die Reaktion. tritt langsam schon bei Raumtemperatur und ohne Katalysator ein, schneller bei höherer Temperatur. Es wurde gefunden, daß sie sich weiter beschleunigen läßt durch Bestrahlung mit ultraviolettem Licht und durch Anwendung sowohl von üblichen Friedel-Crafts-Katalysatoren als auch von Platin und anderen Metallen der VIII. Nebengruppe -des Periodischen Systems als Katalysator.This synthesis proceeds in good yield with the addition of one H2 S molecule to one or two carbon double bonds and can depending on the type of applied silane derivative carried out under atmospheric or elevated pressure will. The reaction. occurs slowly at room temperature and without a catalyst one, faster at higher temperature. It has been found that they continue to accelerate lets by irradiation with ultraviolet light and by applying both usual Friedel-Crafts catalysts as well as platinum and other metals of the VIII. Subgroup of the periodic system as a catalyst.
Die Produkte dieser Reaktion sind als Zusatzstoffe zur Verbesserung von Schmiermitteln verwendbar. Beispiel 1 In einem mit 160g Vinyltrichlorsilan gefüllten Autoklav werden 17g Schwefelwasserstoff gepreßt, entsprechend einem molaren Verhältnis 2:1, und dieser Reaktionsansatz wird 12 Stunden lang auf 220° C erhitzt. Der Druck braucht dabei nicht auf bestimmter Höhe gehalten zu werden; er steigt anfänglich auf etwa 100 at und fällt dann im Laufe der Reaktion auf ungefähr 20 at. Der Umsatz beträgt etwa 50%,. Neben einem unbedeutenden Anteil höhersiedender Verbindungen bildet sich Di-[ß-(trichlorsilyl)-äthyl]-sulfid, CisSi-CH2«CH2-S-CH2-CH2-S'C13, mit einem Siedepunkt zwischen 114 und 116° C bei 2 Torr.The products of this reaction are used as additives for improvement usable by lubricants. Example 1 In a filled with 160g vinyltrichlorosilane 17 g of hydrogen sulfide are pressed into the autoclave, corresponding to a molar ratio 2: 1, and this reaction mixture is heated to 220 ° C. for 12 hours. The pressure does not need to be kept at a certain height; it rises initially to about 100 at and then falls in the course of the reaction to about 20 at. The conversion is about 50%. In addition to an insignificant proportion of higher-boiling compounds forms di- [ß- (trichlorosilyl) ethyl] sulfide, CisSi-CH2 «CH2-S-CH2-CH2-S'C13, with a boiling point between 114 and 116 ° C at 2 torr.
Beispiel 2 Ein zusätzlich Platinasbest enthaltender, sonst dem Beispiel 1 analoger Ansatz erreicht schon nach 8 Stunden einen Umsatz von 70% des angewandten Silans. Das Produkt besteht zu 90 Gewichtsprozent aus denn im Beispiel 1 bezeichneten Thioäther neben 10 Gewichtsprozent höhersiedendem Anteil.Example 2 An additional platin asbestos containing, otherwise the example 1 analog approach achieves a conversion of 70% of that used after just 8 hours Silane. The product consists of 90 percent by weight of what is specified in Example 1 Thioether in addition to 10 percent by weight higher-boiling portion.
Beispiel 3 Einem unter Rückflußkühlung auf 130° C erhitzten und mit ultraviolettem Licht bestrahlten Ansatz von 200 g Vinyltriäthoxysilan werden im Laufe von 24 Stunden 30 g Schwefelwasserstoff zugeleitet, worauf ohne Gaszufuhr die Behandlung weitere 4 Stunden lang fortgesetzt wird. Danach ist etwa die Hälfte des vorgelegten Silans umgesetzt; das Produkt besteht zu 50 Gewichtsprozent aus Di-[ß-(triäthoxysilyl)-äthyl ] -sulfid, (C.H50)3Si-CH2-CH2-S-CH2-CH2-Si (O C2 H5) 3, mit Siedepunkt 156 bis 157° C bei 1 Torr, zu 5 Gewichtsprozent aus ,B-(Triäthoxysilyl)-äbhylmcrcaptan, (C,H50)3Si. CH2 - CH2 - SH, mit Siedepunkt 85 bis 86° C bei 3 Torr und im übrigen aus höhersiedenden Nebenprodukten.Example 3 A heated under reflux to 130 ° C and with Ultraviolet light irradiated batch of 200 g Vinyltriäthoxysilan are im In the course of 24 hours, 30 g of hydrogen sulfide were fed in, whereupon without gas supply treatment is continued for another 4 hours. After that is about half of the presented silane implemented; the product consists of 50 percent by weight Di- [ß- (triethoxysilyl) ethyl] sulfide, (C.H50) 3Si-CH2-CH2-S-CH2-CH2-Si (O C2 H5) 3, with boiling point 156 to 157 ° C at 1 Torr, to 5 percent by weight of, B- (triethoxysilyl) -äbhylmcrcaptan, (C, H50) 3Si. CH2 - CH2 - SH, with boiling point 85 to 86 ° C at 3 Torr and the rest from higher boiling by-products.
Ein analoger Vergleichsansatz ohne Ultraviolettaktivierung ergibt nach 8 Stunden nur einen sehr geringen Umsatz, und zwar hauptsächlich zu dem genannten Mercaptan.An analogous comparison approach without ultraviolet activation results after 8 hours only a very low conversion, mainly to that mentioned Mercaptan.
Beispiel 4 Einem unter Rückflußkühlung auf 60° C erhitzten und mit ultraviolettem Licht bestrahlten Ansatz von 20 g Vinyltrimethylsilan werden im Laufe von 24 Stunden 10g Schwefelwasserstoff zugeleitet. Erhalten werden annähernd 26g Reaktionsprodukte, davon destillierbar 16 g Di-[ß-(trimethylsilyl)-äthyl]-sulfid, (CH3)eSi-CH2-CH2-S-CH2-CH2-Si(CH3)3, mit Siedepunkt 65° C bei 1 Torr und ungefähr 2 g ß-(Trimethyls,ilyl)-äthylmercaptan, (CH.), S.i - CH2 -C H2 ' SH. Example 4 A batch of 20 g of vinyltrimethylsilane heated to 60 ° C. under reflux and irradiated with ultraviolet light is fed 10 g of hydrogen sulfide over the course of 24 hours. Approximately 26 g of reaction products are obtained, 16 g of which are distillable di- [ß- (trimethylsilyl) ethyl] sulfide, (CH3) eSi-CH2-CH2-S-CH2-CH2-Si (CH3) 3, with a boiling point of 65 ° C at 1 Torr and about 2 g of β- (trimethyls, ilyl) ethyl mercaptan, (CH.), Si - CH2 -C H2 ' SH.
Beispiel 5 Einem unter Rückflußkühlung bei 88° C siedenden und mit ultraviolettem Licht bestrahlten Ansatz von 84 g Allyltrimethylsilan werden im Laufe von 48 Stunden allmählich ungefähr 25 g Schwefelwasserstoff zugeleitet, wobei 401/9 des vorgelegten Silans umgesetzt werden. Erhalten werden 50 g Reaktionsprodukte, davon 25 g Di-[-(trimethylsilyl)-propyl]-sulfid, (CH3)3Si-CH2-CH2#'CH2.S-CH2.CH2-CH2-Si (CH3)31 mit Siedepunkt 117° C bei 4 Törr.Example 5 A boiling under reflux at 88 ° C and with Ultraviolet light irradiated approach of 84 g of allyltrimethylsilane are in the course of 48 hours gradually supplied about 25 g of hydrogen sulfide, with 401/9 of the presented silane are implemented. 50 g of reaction products are obtained, of which 25 g di - [- (trimethylsilyl) propyl] sulfide, (CH3) 3Si-CH2-CH2 # 'CH2.S-CH2.CH2-CH2-Si (CH3) 31 with boiling point 117 ° C at 4 Törr.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF16378A DE1000817B (en) | 1954-12-15 | 1954-12-15 | Process for the preparation of silyl mercaptans and silyl thioethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF16378A DE1000817B (en) | 1954-12-15 | 1954-12-15 | Process for the preparation of silyl mercaptans and silyl thioethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1000817B true DE1000817B (en) | 1957-01-17 |
Family
ID=7088199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF16378A Pending DE1000817B (en) | 1954-12-15 | 1954-12-15 | Process for the preparation of silyl mercaptans and silyl thioethers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1000817B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206488A (en) * | 1962-02-26 | 1965-09-14 | Stauffer Chemical Co | Organotin compounds containing a mercapto group and a method of preparing them |
| US3314982A (en) * | 1962-05-05 | 1967-04-18 | Th Goldsmidt A G | Organosilicon compounds |
| DE2212239A1 (en) * | 1972-03-14 | 1973-10-04 | Degussa | Continuous organosilicon cpds prepn - from organosilicon halide and alkali metal polysulphide |
| DE2648241A1 (en) * | 1975-12-29 | 1977-06-30 | Dow Corning | PROCESS FOR THE PRODUCTION OF ALKYL POLYSULFIDES |
| DE2834691A1 (en) * | 1978-08-08 | 1980-02-14 | Degussa | MONOMERS, POLYMERS AND CARRIER-FIXED RHODIUM COMPLEX COMPOUNDS, METHOD FOR THEIR PRODUCTION AND USE AS CATALYSTS |
| DE2856229A1 (en) * | 1978-12-27 | 1980-07-03 | Degussa | BIS- (SILYLAETHYL) -OLIGOSULFIDES AND METHOD FOR THE PRODUCTION THEREOF |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567724A (en) * | 1950-11-29 | 1951-09-11 | Gen Electric | Polysilthianes |
-
1954
- 1954-12-15 DE DEF16378A patent/DE1000817B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567724A (en) * | 1950-11-29 | 1951-09-11 | Gen Electric | Polysilthianes |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206488A (en) * | 1962-02-26 | 1965-09-14 | Stauffer Chemical Co | Organotin compounds containing a mercapto group and a method of preparing them |
| US3314982A (en) * | 1962-05-05 | 1967-04-18 | Th Goldsmidt A G | Organosilicon compounds |
| DE2212239A1 (en) * | 1972-03-14 | 1973-10-04 | Degussa | Continuous organosilicon cpds prepn - from organosilicon halide and alkali metal polysulphide |
| DE2648241A1 (en) * | 1975-12-29 | 1977-06-30 | Dow Corning | PROCESS FOR THE PRODUCTION OF ALKYL POLYSULFIDES |
| DE2834691A1 (en) * | 1978-08-08 | 1980-02-14 | Degussa | MONOMERS, POLYMERS AND CARRIER-FIXED RHODIUM COMPLEX COMPOUNDS, METHOD FOR THEIR PRODUCTION AND USE AS CATALYSTS |
| DE2858038C2 (en) * | 1978-08-08 | 1983-11-10 | Degussa Ag, 6000 Frankfurt | MONOMERS, POLYMERS AND CARRIER-FIXED RHODIUM COMPLEX COMPOUNDS, METHOD FOR THEIR PRODUCTION AND USE AS CATALYSTS |
| JPS5856532B2 (en) * | 1978-08-08 | 1983-12-15 | デグッサ アクチェン ゲゼルシャフト | Rhodium complex compound*its manufacture* rhodium polymer complex compound*its manufacture* rhodium compound adhered to carrier*its manufacture and method of carrying out chemical reaction |
| DE2856229A1 (en) * | 1978-12-27 | 1980-07-03 | Degussa | BIS- (SILYLAETHYL) -OLIGOSULFIDES AND METHOD FOR THE PRODUCTION THEREOF |
| FR2445336A1 (en) * | 1978-12-27 | 1980-07-25 | Degussa | BIS- (SILYLETHYL) -OLIGOSULFIDES, PROCESS FOR THEIR PREPARATION AND APPLICATION OF PRODUCTS OBTAINED |
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