DE1178853B - Process for the preparation of organotin mercapto compounds containing boron - Google Patents
Process for the preparation of organotin mercapto compounds containing boronInfo
- Publication number
- DE1178853B DE1178853B DEM19437A DEM0019437A DE1178853B DE 1178853 B DE1178853 B DE 1178853B DE M19437 A DEM19437 A DE M19437A DE M0019437 A DEM0019437 A DE M0019437A DE 1178853 B DE1178853 B DE 1178853B
- Authority
- DE
- Germany
- Prior art keywords
- boric acid
- organotin
- halide
- radical
- patents
- 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
- -1 mercapto compounds Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 3
- 229910052796 boron Inorganic materials 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000004327 boric acid Substances 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 3
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- QNLWRZRUCUXASJ-UHFFFAOYSA-N (4-sulfanylphenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(S)C=C1 QNLWRZRUCUXASJ-UHFFFAOYSA-N 0.000 description 1
- NJHILTVXPBESSS-UHFFFAOYSA-N 2,2-diphenylethyl(oxo)tin Chemical compound C=1C=CC=CC=1C(C[Sn]=O)C1=CC=CC=C1 NJHILTVXPBESSS-UHFFFAOYSA-N 0.000 description 1
- HWFROSPKUYPRBJ-UHFFFAOYSA-N 2,2-diphenylethyltin Chemical compound C=1C=CC=CC=1C(C[Sn])C1=CC=CC=C1 HWFROSPKUYPRBJ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- JXZHQTCIABXDBJ-UHFFFAOYSA-N [2-(sulfanylmethyl)phenoxy]boronic acid Chemical compound B(O)(O)OC1=CC=CC=C1CS JXZHQTCIABXDBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical compound C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- 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
- C07F7/226—Compounds with one or more Sn-S linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/55—Boron-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
- C08K5/58—Organo-tin compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
- C10M2227/083—Sn compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
Description
Verfahren zur Herstellung von borhaltigen Organozinnmercaptoverbindungen Gemäß der Erfindung werden neue Verbindungen hergestellt, die als Organozinnmercaptoderivate bezeichnet werden können und sich durch die folgenden Formeln darstellen lassen: R,Sn(SR" - OBO2R'4n (a) xi (R2Sn)3[(SR'O)3B]2 (b) worin R einen Alkyl-, Aryl- oder Aralkylrest und R" jeweils einen gegebenenfalls substituierten Alkylen-oder Arylenrest, R' einen gegebenenfalls durch Sauerstoffatome ätherartig unterbrochenen aliphatischen oder einen aromatischen Rest bedeutet und x der Wertigkeit des Restes R' entspricht und die Zahlen 1 oder 2 bedeutet.Process for the preparation of boron-containing organotin mercapto compounds According to the invention, new compounds are prepared, which as organotin mercapto derivatives and can be represented by the following formulas: R, Sn (SR "- OBO2R'4n (a) xi (R2Sn) 3 [(SR'O) 3B] 2 (b) where R is an alkyl, aryl or Aralkyl radical and R "each represents an optionally substituted alkylene or arylene radical, R 'is an aliphatic which is optionally interrupted in an ether-like manner by oxygen atoms or denotes an aromatic radical and x corresponds to the valency of the radical R ' and the numbers 1 or 2 means.
Es sei bemerkt, daß bei sämtlichen erfindungsgemäßen Verbindungen der Schwefel in jedem Fall direkt an das Zinnatom gebunden ist und daß die gesamten Valenzen des Zinnatoms, die nicht durch R-Gruppen abgesättigt sind, von schwefelhaltigen Gruppen besetzt sind. It should be noted that in all compounds of the invention the sulfur in each case is bound directly to the tin atom and that the whole Valences of the tin atom that are not saturated by R groups from sulfur-containing ones Groups are occupied.
Die Organozinnmercaptoderivate der vorliegenden Erfindung sind besonders zur Herstellung stabilisierter Polyvinylchloridmassen und auch als Vulkanisationsbeschleuniger, Antioxydationsmittel für Kautschuk, Schmierölzusätze und Polymerisationsbeschleuniger geeignet. The organotin mercapto derivatives of the present invention are particular for the production of stabilized polyvinyl chloride compounds and also as a vulcanization accelerator, Antioxidants for rubber, additives for lubricating oils and polymerization accelerators suitable.
Die neuen Organozinnmercaptoderivate werden dadurch hergestellt, daß man ein Organozinnoxyd, -hydroxyd oder -halogenid, die als organische Reste Alkyl-, Aryl- oder Aralkylgruppen enthalten, mit stöchiometrischen Mengen eines mercaptogruppenhaltigen Borsäureesters der allgemeinen Formel HS R" OBO2R'2 x bzw. ein Di-organozinnoxyd oder -halogenid mit einem mercaptogruppenhaltigen Borsäureester der allgemeinen Formel (HS R" O)3B worin R" jeweils einen gegebenenfalls substituierten Alkylen- oder Arylenrest, R' einen gegebenenfalls durch Sauerstoffatome ätherartig unterbrochenen aliphatischen oder einen aromatischen Rest bedeutet und x der Wertigkeit des Restes R' entspricht und die Zahlen 1 oder 2 bedeutet, vorzugsweise in Gegenwart eines inerten organischen Lösungsmittels umsetzt. The new organotin mercapto derivatives are produced by that one organotin oxide, hydroxide or halide, which as organic residues Containing alkyl, aryl or aralkyl groups, with stoichiometric amounts of one boric acid esters containing mercapto groups of the general formula HS R "OBO2R'2 x or a di-organotin oxide or halide with a boric acid ester containing mercapto groups of the general formula (HS R "O) 3B in which R" each optionally substituted one Alkylene or arylene radical, R 'is ether-like, optionally with oxygen atoms interrupted aliphatic or an aromatic radical and x denotes the valency of the radical R 'and denotes the numbers 1 or 2, preferably in the presence an inert organic solvent.
Werden bei dieser Umsetzung Organozinnhalogenide eingesetzt, so wird es zur Erzielung optimaler Ergebnisse vorgezogen, die Umsetzungen in Gegenwart basischer Substanzen oder von alkalischen Neutralisationsmitteln durchzuführen, die Wasserstoffionen zu binden vermögen, wie Calciumoxyd, Calciumhydroxyd, Natriumhydroxyd, Natriumcarbonat, Natriumbicarbonat, Kaliumcarbonat, Ammoniumhydroxyd, Diäthylamin und Pyridin. Die Produkte können durch Entfernung der Nebenprodukte, wie Wasser oder Chloride, in üblicher Weise isoliert werden. If organotin halides are used in this reaction, then For best results it was preferred to carry out the conversions in the presence more basic Substances or alkaline neutralizing agents that carry hydrogen ions able to bind, such as calcium oxide, calcium hydroxide, sodium hydroxide, sodium carbonate, Sodium bicarbonate, potassium carbonate, ammonium hydroxide, diethylamine and pyridine. the Products can be made by removing the by-products such as water or chlorides in are usually isolated.
Beispiel 1 10 Mol 2-Äthylhexanol, 6 Mol S-Mercaptoäthanol, 5 Mol Borsäure und 200 ccm Toluol wurden in einer 5-1-Flasche erwärmt, die mit einem Rührer für heftiges Rühren, einer Abtrennvorrichtung für Wasser, einem Rückflußkühler und einem Thermometer ausgestattet war. Es wurde so lange unter Rückfluß erhitzt, bis das Reaktionswasser (15 Mol) entfernt worden war. Example 1 10 moles of 2-ethylhexanol, 6 moles of S-mercaptoethanol, 5 moles Boric acid and 200 cc of toluene were heated in a 5-1 bottle fitted with a stirrer for vigorous stirring, a separator for water, a reflux condenser and was equipped with a thermometer. It was refluxed until the water of reaction (15 mol) had been removed.
Es wurden dann 2,5 Mol Dibutylzinnoxyd zugegeben und die Erwärmung unter Rückfluß fortgesetzt, bis 2,5 Mol Wasser entfernt waren. Die Mischung wurde gekühlt, filtriert und unter Vakuum destilliert, um das Toluol zu entfernen. Es wurden 2265 g einer klaren, schwachgelben, viskosen Flüssigkeit, Dibutylzinn-bis-[di-(2-äthylhexyl-p-mercaptoäthyl)-borat], erhalten, welche 12,801, Sn, 6,40/,S und 2,3 0/o B enthielt.2.5 moles of dibutyltin oxide were then added and heating was applied continued under reflux until 2.5 moles of water were removed. The mix was cooled, filtered and vacuum distilled to remove the toluene. It 2265 g of a clear, pale yellow, viscous liquid, dibutyltin bis- [di- (2-ethylhexyl-p-mercaptoethyl) borate], which contained 12.801, Sn, 6.40 /, S and 2.3 0 / o B.
Beispiel 2 2Mol 2-Butyloctanol, 1 Mol Mercaptoäthanol, 1 Mol Borsäure und 100ccm Toluol wurden unter Rückfluß erwärmt und gerührt, bis 3 Mol Wasser aus der Mischung herausdestilliert waren. Es wurde dann 1/2 Mol Dibutylzinnoxyd zugegeben und die Erhitzung unter Rückfluß fortgesetzt, bis 1/2 Mol Wasser entfernt war. Die Mischung wurde gekühlt, filtriert und das Lösungsmittel unter Vakuum abdestilliert, wobei eine schwachgelbe, schwach trübe Flüssigkeit, Dibutylzinn-bis- [di-(2-butyloctyl-mercapto äthyl-borat erhalten wurde, welche 10,3°/O Sn und 5,75 0/o S enthielt. Example 2 2 moles of 2-butyloctanol, 1 mole of mercaptoethanol, 1 mole of boric acid and 100ccm of toluene were heated under reflux and stirred until 3 moles of water the end distilled out of the mixture. 1/2 mole of dibutyltin oxide was then added and refluxing continued until 1/2 mole of water was removed. the Mixture was cooled, filtered and the solvent was distilled off under vacuum, whereby a pale yellow, slightly cloudy liquid, dibutyltin-bis- [di- (2-butyloctyl-mercapto ethyl borate was obtained, which 10.3% Sn and 5.75% S contained.
Beispiel 3 2 Mol Äthylenglykol, 2 Mol Mercaptoäthanol, 2Mol Borsäure und 200 ccm Toluol wurden gerührt und unter Rückfluß erwärmt, bis 6 Mol Wasser herausdestilliert waren. Es wurde 1 Mol Dibutylzinnoxyd zugegeben und weiter erwärmt, bis 1 Mol Reaktionswasser entfernt war. Das Lösungsmittel wurde dann durch Vakuumdestillation entfernt, das Endprodukt war eine stark viskose Flüssigkeit der folgenden Formel: Beispiel 4 62g (1 Mol) Borsäure, 234 g Mercaptoäthanol (3 Mol) und 100 ccm Toluol wurden gerührt und unter Rückfluß erwärmt, bis das gesamte Reaktionswasser mit Hilfe eines Wasserauskreisers entfernt worden war.Example 3 2 moles of ethylene glycol, 2 moles of mercaptoethanol, 2 moles of boric acid and 200 cc of toluene were stirred and refluxed until 6 moles of water had distilled out. 1 mol of dibutyltin oxide was added and heating continued until 1 mol of water of reaction was removed. The solvent was then removed by vacuum distillation, the end product was a highly viscous liquid of the following formula: Example 4 62 g (1 mol) of boric acid, 234 g of mercaptoethanol (3 mol) and 100 cc of toluene were stirred and refluxed until all of the water of reaction had been removed with the aid of a water separator.
Die Mischung wurde anschließend an einer Wasserstrahlpumpe bis zu einer Gefäßtemperatur von 160 0C und einem Druck von 15 Torr destilliert. Der Rückstand, Tri-B-mercaptoäthylborat, (HSC2H5O)3B, ist eine Flüssigkeit von sehr schwacher Färbung.The mixture was then applied to a water pump up to a vessel temperature of 160 0C and a pressure of 15 torr distilled. The residue, Tri-B-mercaptoethyl borate, (HSC2H5O) 3B, is a liquid that is very faintly colored.
186,5 g Dibutylzinnoxyd (0,75 Mol), 120,9 g Trip-mercaptoäthylborat (0,5 Mol) und 200 ccm Toluol wurden gerührt und unter Rückfluß erwärmt, bis das gesamte Reaktionswasser entfernt war. Die Mischung wurde ziemlich viskos, als die letzten Wasserspuren entfernt waren. Sie wurde noch heiß in ein Reaktionsgefäß aus rostfreiem Stahl eingegossen, und die letzten Spuren des Lösungsmittels wurden entfernt, indem das Gefäß in einen Vakuumofen bis zur Gewichtskonstanz eingebracht wurde. Das Endprodukt, ein Dibutylzinnderivat des Tri-ß-mercaptoäthylbo'rats, war eine hochviskose, schwach gefärbte Flüssigkeit mit 16,00/o 5, 29,20/o Sn, 2,20/,B. Es war dennoch Tris-(dibutylZinn)-bis-[S,S',S"-tri-( -mercaptoäthyl)-borat] . 186.5 g of dibutyltin oxide (0.75 mol), 120.9 g of tripmercaptoethyl borate (0.5 mol) and 200 cc of toluene were stirred and heated under reflux until the all water of reaction was removed. The mixture became quite viscous than that last traces of water were removed. She got off in a reaction vessel while still hot stainless steel poured in, and the last traces of solvent were removed, by placing the jar in a vacuum oven to constant weight. The end product, a dibutyltin derivative of tri-ß-mercaptoäthylbo'rats, was one highly viscous, slightly colored liquid with 16.00 / o 5, 29.20 / o Sn, 2.20 /, B. It was nevertheless tris- (dibutyltin) -bis- [S, S ', S "-tri- (mercaptoethyl) borate].
Beispiel 5 3 Mol Dimethylzinnoxyd und 2 Mol p-Mercaptophenylborat wurden in Gegenwart von Toluol unter Rückfluß erwärmt, bis das gesamte Reaktionswasser entfernt worden war. Das Lösungsmittel wurde dann durch Erwärmen unter Vakuum entfernt, wobei eine viskose Flüssigkeit, Tris-dimethylzinn-bis- [5, S,'S"-tri-(4-mercaptophenyl)-borat], erhalten wurde. Example 5 3 moles of dimethyltin oxide and 2 moles of p-mercaptophenyl borate were refluxed in the presence of toluene until all of the water of reaction had been removed. The solvent was then removed by heating under vacuum, being a viscous liquid, tris-dimethyltin-bis- [5, S, 'S "-tri- (4-mercaptophenyl) -borate], was obtained.
Beispiel 6 3 Mol Diphenyläthylzinnoxyd und 2 Mol ß-Phenylß-mercaptoäthylborat wurden in Gegenwart von Toluol unter Rückfluß erwärmt, bis das gesamte Reaktionswasser entfernt war. Das Lösungsmittel wurde dann durch Erwärmen unter Vakuum entfernt und dabei eine viskose Flüssigkeit, Tris-(diphenylãthylzinn)-bis- [S, S', S"-tri-(,-phenyl-ß-mercaptoäthyl)-borat], erhalten. Example 6 3 moles of diphenylethyltin oxide and 2 moles of ß-phenylß-mercaptoethyl borate were refluxed in the presence of toluene until all of the water of reaction was removed. The solvent was then removed by heating under vacuum and a viscous liquid, tris- (diphenylethyltin) -bis- [S, S ', S "-tri - (, - phenyl-ß-mercaptoethyl) borate], obtain.
Beispiel 7 3 Mol Dilaurylzinnoxyd und 2 Mol o-Mercaptomethylphenylborat wurden in Gegenwart von Toluol unter Rückfluß erwärmt, bis das gesamte Reaktionswasser entfernt war. Das Lösungsmittel wurde dann durch Erwärmen unter Vakuum entfernt und dabei als viskose Flüssigkeit Tris-(dilaurylzinn)-bis-[S,S',S"-tri-(o-mercaptoäthylphenyl)-borat] erhalten. Example 7 3 moles of dilauryltin oxide and 2 moles of o-mercaptomethylphenyl borate were refluxed in the presence of toluene until all of the water of reaction was removed. The solvent was then removed by heating under vacuum and as a viscous liquid tris- (dilauryltin) -bis- [S, S ', S "-tri- (o-mercaptoethylphenyl) -borate] obtain.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM19437A DE1178853B (en) | 1953-07-23 | 1953-07-23 | Process for the preparation of organotin mercapto compounds containing boron |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM19437A DE1178853B (en) | 1953-07-23 | 1953-07-23 | Process for the preparation of organotin mercapto compounds containing boron |
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| Publication Number | Publication Date |
|---|---|
| DE1178853B true DE1178853B (en) | 1964-10-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| DEM19437A Pending DE1178853B (en) | 1953-07-23 | 1953-07-23 | Process for the preparation of organotin mercapto compounds containing boron |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4608440A (en) * | 1984-02-07 | 1986-08-26 | Chemie Linz Aktiengesellschaft | 1,3,2-dioxaborinanes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2636891A (en) * | 1950-12-27 | 1953-04-28 | Du Pont | Heterocyclic organo-tin compounds containing oxygen, sulfur, and tin in the ring |
| US2641596A (en) * | 1952-02-07 | 1953-06-09 | Argus Chemical Lab Inc | Organic derivatives of tetravalent tin |
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1953
- 1953-07-23 DE DEM19437A patent/DE1178853B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2636891A (en) * | 1950-12-27 | 1953-04-28 | Du Pont | Heterocyclic organo-tin compounds containing oxygen, sulfur, and tin in the ring |
| US2641596A (en) * | 1952-02-07 | 1953-06-09 | Argus Chemical Lab Inc | Organic derivatives of tetravalent tin |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4608440A (en) * | 1984-02-07 | 1986-08-26 | Chemie Linz Aktiengesellschaft | 1,3,2-dioxaborinanes |
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