DE1079329B - Process for the production of new organotin compounds - Google Patents
Process for the production of new organotin compoundsInfo
- Publication number
- DE1079329B DE1079329B DEF25240A DEF0025240A DE1079329B DE 1079329 B DE1079329 B DE 1079329B DE F25240 A DEF25240 A DE F25240A DE F0025240 A DEF0025240 A DE F0025240A DE 1079329 B DE1079329 B DE 1079329B
- Authority
- DE
- Germany
- Prior art keywords
- tin
- production
- organotin compounds
- ethylene oxide
- compounds
- 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
- 150000001875 compounds Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 description 19
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- 241000223602 Alternaria alternata Species 0.000 description 4
- 241000123650 Botrytis cinerea Species 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- -1 hydrogen inorganic Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 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
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von neuen Organo-Zinnverbindungen Gegenstand der Erfindung ist ein Verfahren zur Herstellung neuer Organo-Zinnverbindungen mit verhältnismäßig niedrigem Zinngehalt. Process for the production of new organotin compounds of the invention is a process for the preparation of new organotin compounds with relatively low tin content.
Es sind organische Verbindungen des Zinns bekannt, in denen an ein neutrales vierwertiges Zinn atom bis zu vier gleiche oder verschiedene organische Reste gebunden sind. Sie werden für verschiedene technische Anwendungen benutzt, beispielsweise als baktericide und fungicide Wirkstoffe. Ihrer Anwendung sind aber dadurch gewisse Grenzen gesetzt, daß sie infolge ihres hohen Zinngehaltes der meistens 20 Gewichtsprozent übersteigt, ziemlich teuer sind. There are known organic compounds of tin in which an neutral tetravalent tin atom up to four identical or different organic atoms Remnants are bound. They are used for various technical applications, for example as bactericidal and fungicidal active ingredients. Your application are, however certain limits are set by the fact that, due to their high tin content, they are mostly 20 percent by weight are quite expensive.
Es wurde nun gefunden, daß man neue ziunarme Organo-Zinnverbindungen in der Weise herstellen kann, daß man organische Verbindungen des vierwertigen Zinns, in denen mindestens ein organischer Rest über Kohlenstoff direkt an Zinn gebunden ist, während bis zu drei Valenzen des Zinnatoms mit von aktivem Wasserstoff freien anorganischen oder organischen Säureresten, wie Halogen, Phosphat oder Acetat, besetzt sind, mit Äthylen, Propylenoxyd oder noch höheren Olefinoxyden zur Reaktion bringt. Dabei lagert sich das Alkylenoxyd an denjenigen Stellen der Ausgangsverbindung ein, an denen das zentrale Zinnatom nicht unmittelbar über Kohlenstoff mit organischen Resten verknüpft ist. So entsteht beispielsweise nach der Erfindung durch Oxäthylierung von Triphenylzinnchlorid ein Großmolekül der Formel (C6H5)2Sn - (OCH2 - CH2)nCl wobei it eine ganze Zahl von 1 bis 50 bedeuten kann. It has now been found that new low-gun organotin compounds can be obtained can be produced in such a way that organic compounds of tetravalent tin, in which at least one organic residue is bonded directly to tin via carbon is, while up to three valences of the tin atom with free of active hydrogen inorganic or organic acid residues, such as halogen, phosphate or acetate, occupied reacts with ethylene, propylene oxide or even higher olefin oxides. The alkylene oxide is deposited at those points of the starting compound where the central tin atom is not directly above carbon with organic Remnants is linked. For example, according to the invention, by oxyethylation of triphenyltin chloride a large molecule of the formula (C6H5) 2Sn - (OCH2 - CH2) nCl where it can be an integer from 1 to 50.
Bei dieser Umsetzung mit Alkylenoxyden entstehen Gemische von hochmolekularen Verbindungen mit verschiedenen Längen der Polyglykolketten, wobei die Anzahl der die Kette bildenden Einzelglieder - OCH2 - CH2 - etwa zwischen 1 und 50 schwankt. This reaction with alkylene oxides results in mixtures of high molecular weight Compounds with different lengths of polyglycol chains, the number of the individual links forming the chain - OCH2 - CH2 - fluctuates between 1 and 50.
Es läßt sich keine Aussage darüber machen, wie lang jeweils die einzelnen Ketten sind; jedoch ist stets der Gesamtgehalt an Alkylenoxyd im jeweiligen Verfahrensprodukt feststellbar, da er sich aus der Gewichtszunahme des Polyoxallvlierungsproduktes gegenüber der Ausgangs-Zinnverbindung ergibt.No statement can be made about how long each one Chains are; however, it is always the total content of alkylene oxide in the respective process product ascertainable, since it results from the increase in weight of the polyoxal-lamination product compared to the starting tin compound.
Als geeignete Ausgangsverbindungen werden beispielsweise genannt: Monobutylzinntrichlorid, Dibutylzinndichlorid, Tributylzinnmonochlorid, Triphenylzinnmonochlorid, Triphenylzinnmonoacetat, Dibutylzinndiacetat, Dibutylzinn-bis-(O,O-diäthylphosphat), Tributyl-(p-toluolsulfamido) -Zinn. Examples of suitable starting compounds are: Monobutyltin trichloride, dibutyltin dichloride, tributyltin monochloride, triphenyltin monochloride, Triphenyltin monoacetate, dibutyltin diacetate, dibutyltin-bis- (O, O-diethyl phosphate), Tributyl (p-toluenesulfamido) tin.
Die Reaktion dieser Körper mit Alkylenoxyden wird durch geeignete Katalysatoren gefördert, z. B. mittels Zinntetrachlorid, Kaliumhydroxyd, Natriumhydroxyd, Kaliumalkoholat, Natriumalkoholat. Alkylenoxyd, vorzugsweise Äthylenoxyd, wird bei erhöhter Temperatur eingeleitet. Durch Anwendung von Druck wird die Reaktion erleichtert und beschleunigt. The reaction of these bodies with alkylene oxides is by appropriate Promoted catalysts, z. B. using tin tetrachloride, potassium hydroxide, sodium hydroxide, Potassium alcoholate, sodium alcoholate. Alkylene oxide, preferably ethylene oxide, is used in elevated temperature initiated. The application of pressure will facilitate the reaction and accelerated.
Beispiele 1. 40g Dibutylzinndichlorid (39,1 01o Sn) werden mit einigen Tropfen Sn C14 versetzt. Dann wird in das Gemisch bei 160 bis 180"C so lange Äthylenoxyd eingeleitet, bis eine Gewichtszunahme von 70 g erreicht ist.Das Reaktionsprodukt ist ein dickflüssiges Ö1 mit 14,2 01o Zinn und kann durch die allgemeine Formel gekennzeichnet werden.Examples 1. 40 g of dibutyltin dichloride (39.110 Sn) are mixed with a few drops of Sn C14. Ethylene oxide is then introduced into the mixture at 160 to 180 "C until a weight increase of 70 g is reached. The reaction product is a viscous oil with 14.2 01o tin and can be given by the general formula be marked.
2. Man versetzt 30 g Triphenylzinnchlorid (Zinngehalt 30,8 0in) mit einigen Tropfen Zinntetrachlorid und leitet hierauf bei 170 bis 180"C Äthylenoxyd ein, bis ein hellbraunes weiches Wachs entsteht, das einen Zinngehalt von 14,4°/o aufweist. Es ist durch die allgemeine Formel (C6H5)3Sn (OCH2CH2)nCl gekennzeichnet. Das Produkt eignet sich gut zur Bekämpfung von Alternaria tenuis und Botrytis cinerea. 2. 30 g of triphenyltin chloride (tin content 30.8 0in) are added a few drops of tin tetrachloride and then conducts ethylene oxide at 170 to 180 "C until a light brown, soft wax is obtained which has a tin content of 14.4 per cent having. It is characterized by the general formula (C6H5) 3Sn (OCH2CH2) nCl. The product is well suited for combating Alternaria tenuis and Botrytis cinerea.
3. Man versetzt 24 g Dibutylzinndiacetat (37,20/, Sn) mit 0,12 g gepulvertem Ätzkali und leitet bei einer von 170 bis 200"C ansteigenden Temperatur so lange Äthylenoxyd ein, bis 52 g desselben aufgenommen sind. 3. 24 g of dibutyltin diacetate (37.20 /, Sn) are mixed with 0.12 g powdered caustic potash and conducts at a temperature rising from 170 to 200 "C ethylene oxide until 52 g of it are absorbed.
Man erhält ein dunkles Ö1, das 10,5 01o Sn enthält und der a emeinen Formel entspricht. Das Produkt hat eine gute fungicide Wirkung gegenüber Alternaria tenuis und Botrytis cinerea.A dark oil is obtained which contains 10.5% Sn and has the general formula is equivalent to. The product has a good fungicidal effect against Alternaria tenuis and Botrytis cinerea.
4. Man vermischt 50 g Tributylzinnchlorid (36,5 01o Sn) mit einigen Tropfen SnCl und leitet unter Rühren bei 1700C Äthylenoxyd ein, bis 27 g Äthylenoxyd aufgenommen sind. Es entsteht ein dickes Öl mit einem Zinngehalt von 23,7 01o Sn. Das Produkt hat die allgemeine Formel (C4H9)3 - Sn - (OCH2 - CH2)n - Cl und besitzt sehr gute Wirksamkeit gegenüber Alternaria tenuis und Botrytis cinerea. 4. Mix 50 g of tributyltin chloride (36.5 01o Sn) with some Drops of SnCl and introduces ethylene oxide with stirring at 1700C, up to 27 g of ethylene oxide are included. The result is a thick oil with a tin content of 23.7 01o Sn. The product has the general formula (C4H9) 3 - Sn - (OCH2 - CH2) n - Cl and has very effective against Alternaria tenuis and Botrytis cinerea.
5. 50 g Tributylzinn-O,O-Diäthylzinnphosphat der Formel (Zinngehalt 26,8 0/o) werden mit 0,5 g gepulvertem Ätzkali vermischt und hierauf bei 1800C Äthylenoxyd ein- geleitet, bis eine Gewichtszunahme von 50 g erreicht ist.5. 50 g of tributyltin O, O-diethyltin phosphate of the formula (Tin content 26.8%) are mixed with 0.5 g of powdered caustic potash and then ethylene oxide is introduced at 1800C until a weight increase of 50 g is reached.
Das Reaktionsprodukt ist ein dunkles Ö1, welches noch 13,3 0/o Zinn enthält. Trotz des herabgesetzten Zinngehaltes hat das Produkt noch eine gute fungicide Wirkung gegen Botrytis cinerea und Alternaria tenuis Es kann durch die allgemeine Formel gekennzeichnet werden.The reaction product is a dark oil which still contains 13.3% tin. Despite the reduced tin content, the product still has a good fungicidal effect against Botrytis cinerea and Alternaria tenuis. It can be achieved through the general formula be marked.
PATENTANSPRCHE: t. Verfahren zur Herstellung von Organozinnverbindungen, dadurch gekennzeichnet, daß man eine Organozinnverbindung, in der mindestens ein organischer Rest über Kohlenstoff unmittelbar an das zentrale Zinnatom gebunden ist, während bis zu drei Valenzen des Zinns mit anorganischen oder organischen, jedoch keine aktiven Wasserstoffatome tragenden Säureresten besetzt sind, mit Alkylenoxyd bei erhöhter Temperatur mit oder ohne Anwendung von Druck zur Reaktion bringt. PATENT CLAIMS: t. Process for the production of organotin compounds, characterized in that one organotin compound in which at least one organic residue bound directly to the central tin atom via carbon is, while up to three valences of tin with inorganic or organic, but no acid residues bearing active hydrogen atoms are occupied by alkylene oxide reacts at elevated temperature with or without the application of pressure.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25240A DE1079329B (en) | 1956-05-15 | 1956-05-15 | Process for the production of new organotin compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25240A DE1079329B (en) | 1956-05-15 | 1956-05-15 | Process for the production of new organotin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1079329B true DE1079329B (en) | 1960-04-07 |
Family
ID=7091543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF25240A Pending DE1079329B (en) | 1956-05-15 | 1956-05-15 | Process for the production of new organotin compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1079329B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242201A (en) * | 1959-04-06 | 1966-03-22 | Cramer Charles Robert | Emulsifiable organotin compounds and process for making same |
-
1956
- 1956-05-15 DE DEF25240A patent/DE1079329B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242201A (en) * | 1959-04-06 | 1966-03-22 | Cramer Charles Robert | Emulsifiable organotin compounds and process for making same |
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