EP0000747B1 - Halogénures d'organoétain et procédé pour leur préparation - Google Patents

Halogénures d'organoétain et procédé pour leur préparation Download PDF

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Publication number
EP0000747B1
EP0000747B1 EP78100533A EP78100533A EP0000747B1 EP 0000747 B1 EP0000747 B1 EP 0000747B1 EP 78100533 A EP78100533 A EP 78100533A EP 78100533 A EP78100533 A EP 78100533A EP 0000747 B1 EP0000747 B1 EP 0000747B1
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EP
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Prior art keywords
alkyl
mixture
radicals
tin
organotin halides
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EP78100533A
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German (de)
English (en)
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EP0000747A1 (fr
Inventor
Helmut Dr. Korbanka
Franz Dr. Scheidl
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Hoechst AG
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Hoechst AG
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    • 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
    • C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen

Definitions

  • the invention relates to new organotin halides and a process for their preparation.
  • organotin halides such as dibutyltin dichloride, monobutyltin trichloride or dioctyltin dichloride, are very complex and, for. T. dangerous and therefore expensive because they are based on the Grignard, aluminum alkyl or Wurtz synthesis.
  • tetraalkyl or tetraaryl compounds are prepared from alkyl or aryl chlorides and tin tetrachloride (Grignard, Wurtz) or from aluminum alkyls and tin tetrachloride, which are then converted into the desired tri-, di- and monoorganotin chlorides by comproportionation processes with tin tetrachloride.
  • organotin halides Another possibility for the production of organotin halides is to react metallic tin and hydrogen halide with activated olefins. These are olefins of the general formula in which B, C and D represent hydrogen or a hydrocarbon radical and the radical A, but optionally also the radical B, contains a carbonyl group adjacent to the olefinic double bond (DT-OS 2 607 178).
  • B, C and D represent hydrogen or a hydrocarbon radical and the radical A, but optionally also the radical B, contains a carbonyl group adjacent to the olefinic double bond (DT-OS 2 607 178).
  • the mixtures of organotin di- and trihalides which can be prepared in high yields by this process are contaminated in some cases, in particular if the reaction is carried out at higher temperatures, by polymers of the starting olefins formed in side reactions, and these side products cannot be separated off practically. If they reach organotin stabilizers with them in plastic masses during
  • R 1 are -OH, -NH 2 , ⁇ Cl, -Br. -J, alkyl and
  • R 2 to R 4 are at least one radical of the structure in addition hydrogen, methyl, ethyl, propyl, hexyl, dodecyl, octadecyl.
  • Preferred compounds are those in which R 'is an O-alkyl radical having 1 to 40, preferably 1 to 30 and in particular 1 to 20 carbon atoms and R 3 and R 4 are hydrogen, R 2 is the radical with the preferred range given for R 1 and X represents chlorine.
  • the reaction can be carried out without solvent or in e.g. Ethers, such as diethyl ether, tetrahydrofuran, dioxane or 1,2-dimethoxyethane, in esters such as ethyl acetate, in ketones such as acetone or ethyl methyl ketone, in alcohols such as methanol, ethanol and butanol, in aromatic hydrocarbons such as toluene, xylene, chlorobenzene, etc. ., in aliphatic hydrocarbons, such as petrol, chlorine-containing aliphatics such as chloroform and carbon tetrachloride, in water (as concentrated hydrochloric acid) or in an excess of olefin.
  • Ethers such as diethyl ether, tetrahydrofuran, dioxane or 1,2-dimethoxyethane
  • esters such as ethyl acetate
  • ketones such as acetone or
  • the hydrogen halide can be introduced into the reaction in gaseous form or as an aqueous solution, especially as a concentrated aqueous solution. Hydrogen chloride is preferred.
  • the metallic tin is suitable for implementation in any form, but is preferred because of its large, i.e. reactive surface is the powdered tin, but granulated tin can also be used.
  • the reaction can either be designed in such a way that the olefin, solvent and tin are introduced and hydrogen halide is introduced, or the olefin / solvent mixture is saturated with hydrogen halide and only then tin is added.
  • the reaction can be carried out at temperatures between 0 and 150 ° C., expediently one works between about 0 and 100, preferably at 20 to 80 ° C.
  • the oraganotin halides obtainable during the reaction are mixtures of di- and monoorganotin halides of the general formula (R) 2 SnHaI 2 and (R) SnHal 3 , the rest R having the general structure is attributable. Based on the analytical and spectroscopic data, the course of the reaction and the chemistry of these olefins, this structure is very likely.
  • the approximate ratio of the di to the mono compound can be determined mathematically from the chlorine contents of the reaction products, it varies widely and depends on the starting products and the process conditions (for example on the solvent used and the rate at which hydrogen halide is introduced).
  • the proportion of monoorganotin trichloride (B) SnCl 3 in the reaction mixture is generally between 0.01 and 80% by weight, ie the ratio of diorganotin chloride to monoorganotin chloride is approximately 1: 0 to 1: 4.
  • the di- and trihalogenides can be separated by known methods, e.g. by fractional crystallization, possible, but in particular not necessary if the process products are further processed on tin stabilizers.
  • the new organotin halides are valuable intermediates that e.g. suitable for the synthesis of crop protection and pesticides and as starting materials for the production of heat stabilizers for plastics processing.
  • the chlorine analyzes also show that practically no hydrogen chloride has been added to the double bond of the dimethyl itaconate.
  • the iodine number found proves that practically no itaconic acid ester is present.
  • reaction product is heated in sufficient toluene, a clear solution is formed, from which, on cooling, the connection of the structure in the form of white crystals of mp 144 to 146 ° C. fails.
  • Example 2 The procedure was as in Example 2; however at a temperature of 120 to 125 ° C.
  • the product of the process corresponded in all analysis values to that obtained in Example 2. It also contained no trace of polymethyl itaconate.
  • Example 2 the method described in Example 1 was used. 29.6 g (0.25 mol) of tin and 36.5 g (1 mol) of hydrogen chloride gas were always used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Claims (4)

1. Mélange d'halogénures organo-stanniques caractérisés par les formules générales
Figure imgb0030
dans lesquelles
R1 désigne un groupe OH, un atome d'halogène, un groupe amino, un radical alkylamino ou arylamino, un radical O-alkyle ou un radical O-aryle, les deux derniers radicaux pouvant également être substitués par un groupe aryle ou alkyle et pouvant porter, tels quels ou substitués par un groupe aryle ou alkyle, le cas échéant comme substituants additionnels, un atome d'halogène ou un groupe hydroxyle, un groupe thio-éther, un groupe d'éther et/ou un groupe carboxyle,
R2 à R4 peuvent être identiques ou différents et désignent de 0 à 2 atomes d'hydrogène ainsi que des radicaux alkyles ayant de 1 à 20 atomes de carbone, cependant, d'au moins un de ces radicaux représentant un groupe
Figure imgb0031
dans lequel n est un nombre de 1 à 15,
X désigne un atome de chlore, de brome ou d'iode, et les radicaux R1 à R4 et X correspondant l'un à l'autre dans les deux composantes 1 et Il du mélange sont toujours identiques.
2. Mélange d'halogénures organo-stanniques selon la revendication 1, caractérisé en ce que dans les deux composants le radical R1 est un groupe O-alkyle ayant de 1 à 40 atomes de carbone, le radical R2 désigne le radical
Figure imgb0032
avec R1 ayant la signification indiquée ci-dessus, X est un atome de chlore, et les radicaux R3 et R4 désignent chacun un atome d'hydrogène.
3. Mélange d'halogénures organo-stanniques selon l'une des revendications 1 et 2, caractérisé en ce que le rapport en poids de la composante l à la composante Il est de 1 : 0,01 à 1 : 4.
4. Procédé de préparation des mélanges d'halogénures organo-stanniques spécifiés dans les revendications 1 et 2, caractérisé en ce qu'on fait réagir une oléfine répondant à la formule générale
Figure imgb0033
dans laquelle les radicaux R1 à R4 ont les significations données aux revendications 1 et 2, avec de l'étain métallique et un halogénure d'hydrogène aqueux ou gazeux, le cas échéant en présence d'un solvant inerte à des températures comprises entre environ 0 et 150°C.
EP78100533A 1977-08-09 1978-07-28 Halogénures d'organoétain et procédé pour leur préparation Expired EP0000747B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772735757 DE2735757A1 (de) 1977-08-09 1977-08-09 Neue organozinnhalogenide und verfahren zu deren herstellung
DE2735757 1977-08-09

Publications (2)

Publication Number Publication Date
EP0000747A1 EP0000747A1 (fr) 1979-02-21
EP0000747B1 true EP0000747B1 (fr) 1980-06-25

Family

ID=6015925

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100533A Expired EP0000747B1 (fr) 1977-08-09 1978-07-28 Halogénures d'organoétain et procédé pour leur préparation

Country Status (6)

Country Link
US (1) US4202830A (fr)
EP (1) EP0000747B1 (fr)
JP (1) JPS5430118A (fr)
CA (1) CA1120940A (fr)
DE (2) DE2735757A1 (fr)
IT (1) IT1098004B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2850150A1 (de) * 1978-11-18 1980-05-29 Hoechst Ag Verfahren zur herstellung von organozinntrihalogeniden und ihre verwendung
US4285856A (en) * 1979-02-14 1981-08-25 Ciba-Geigy Corporation Organo-tin compounds, process for their preparation and their use
FR2458554A1 (fr) * 1979-05-23 1981-01-02 Elf Aquitaine Procede de preparation de trihalogenures organostanniques
DE3265868D1 (en) * 1981-10-08 1985-10-03 Ciba Geigy Ag Organotin compounds
EP1743898A1 (fr) 2005-07-12 2007-01-17 Arkema Vlissingen B.V. Procédé de préparation des composés haloétain mono- et dialkylés

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3440255A (en) * 1967-09-28 1969-04-22 Sumio Matsuda Process for preparing organotin halides
US4105684A (en) * 1974-09-16 1978-08-08 Akzo N.V. Process for the preparation of organotin trihalides
NL7412230A (nl) * 1974-09-16 1976-03-18 Akzo Nv Werkwijze voor de bereiding van organotintri- halogeniden.
US4080363A (en) * 1975-03-17 1978-03-21 Akzo N.V. Process for making organotin dihalides and trihalides and stabilizers prepared therefrom
NL7503116A (nl) * 1975-03-17 1976-09-21 Akzo Nv Werkwijze voor het bereiden van organotindihaloge- niden, alsmede daarvan afgeleide organotinstabi- lisatoren.

Also Published As

Publication number Publication date
IT7826561A0 (it) 1978-08-07
CA1120940A (fr) 1982-03-30
DE2735757A1 (de) 1979-02-15
EP0000747A1 (fr) 1979-02-21
IT1098004B (it) 1985-08-31
DE2860030D1 (en) 1980-10-30
JPS5430118A (en) 1979-03-06
US4202830A (en) 1980-05-13

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