EP0000747A1 - 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
EP0000747A1
EP0000747A1 EP7878100533A EP78100533A EP0000747A1 EP 0000747 A1 EP0000747 A1 EP 0000747A1 EP 7878100533 A EP7878100533 A EP 7878100533A EP 78100533 A EP78100533 A EP 78100533A EP 0000747 A1 EP0000747 A1 EP 0000747A1
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EP
European Patent Office
Prior art keywords
alkyl
radicals
radical
mixture
organotin halides
Prior art date
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EP7878100533A
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German (de)
English (en)
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EP0000747B1 (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 radical A, but optionally also 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 radical A, but optionally also 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 when 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, during the further processing of the organotin halides on organotin stabilize
  • organotin halides can be prepared in the form of mixtures of di- and trihalides.
  • R 1 examples are -OH, -NH 2 , -Cl, -Br. -J, alkyl and arylamino radicals such as -NH (CH 3 ), O-alkyl radicals such as - OCH3 , -OC 2 H 5 , -OC 8 H 17 , -O-CH 2 -CH 2 -OH, -O-CH 2 -CH 2 -Cl, -O-CH 2 -CH 2 -O-CH 3 , -O-CH 2 -CH 2 -S-CH 2 -CH 2 -OH, and o-aryl residues such as.
  • alkyl and arylamino radicals such as -NH (CH 3 ), O-alkyl radicals such as - OCH3 , -OC 2 H 5 , -OC 8 H 17 , -O-CH 2 -CH 2 -OH, -O-CH 2 -CH 2 -Cl, -O-CH 2
  • R 1 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 above and X represents chlorine.
  • Preferred olefins are the esters of itaconic acid.
  • 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 e
  • 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 Carry out 150 ° C, expediently you work between about 0 and 100, preferably at 20 to 80 ° C.
  • the oraganotin halides obtainable in the reaction are mixtures of di- and monoorganotin halides of the general formula (R) 2 SnHal 2 and (R) SnHal 3 , where the radical R is 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 calculated from the chlorine content of the reaction products, it varies widely and depends on the starting products and the process conditions (e.g. the solvent used and the rate of introduction of the hydrogen halide).
  • the proportion of monoorganotin trichloride (R) 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 trihalides 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 can be used, for example, for the synthesis of crop protection and pesticides and as starting products for the production of heat stabilizers suitable for plastics processing.
  • a 500 ml three-necked flask equipped with a stirring device, internal thermometer and a gas inlet tube was charged with 79 g (0.5 mol) dimethyl itaconate, 29.6 g (0.25 mol) tin powder and 150 ml diethyl ether.
  • a total of 36.5 g (1 mol) of dry, gaseous hydrogen chloride were introduced uniformly over the course of 2.5 hours with vigorous stirring and cooling at a temperature of 20 to 25 ° C.
  • the mixture was stirred at 20 to 25 ° C for a further 10 hours. After that there was no more tin.
  • the ether and the excess hydrogen chloride were then removed under a water jet vacuum.
  • 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)
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
DE2735757 1977-08-09
DE19772735757 DE2735757A1 (de) 1977-08-09 1977-08-09 Neue organozinnhalogenide und verfahren zu deren herstellung

Publications (2)

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

Family

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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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011280A1 (fr) * 1978-11-18 1980-05-28 Hoechst Aktiengesellschaft Procédé de préparation de trihalogénures d'organoétain et leur application
FR2458554A1 (fr) * 1979-05-23 1981-01-02 Elf Aquitaine Procede de preparation de trihalogenures organostanniques

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4285856A (en) * 1979-02-14 1981-08-25 Ciba-Geigy Corporation Organo-tin compounds, process for their preparation and their use
EP0077296B1 (fr) * 1981-10-08 1985-08-28 Ciba-Geigy Ag Composés d'organoétain
EP1743898A1 (fr) 2005-07-12 2007-01-17 Arkema Vlissingen B.V. Procédé de préparation des composés haloétain mono- et dialkylés

Citations (2)

* 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
FR2306208A1 (fr) * 1975-03-17 1976-10-29 Akzo Nv Procede pour preparer des dihalogenures organostanniques utiles comme intermediaires dans la preparation des stabilisants pour polymeres

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7412230A (nl) * 1974-09-16 1976-03-18 Akzo Nv Werkwijze voor de bereiding van organotintri- halogeniden.
US4105684A (en) * 1974-09-16 1978-08-08 Akzo N.V. Process for the preparation of organotin trihalides
US4080363A (en) * 1975-03-17 1978-03-21 Akzo N.V. Process for making organotin dihalides and trihalides and stabilizers prepared therefrom

Patent Citations (2)

* 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
FR2306208A1 (fr) * 1975-03-17 1976-10-29 Akzo Nv Procede pour preparer des dihalogenures organostanniques utiles comme intermediaires dans la preparation des stabilisants pour polymeres

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011280A1 (fr) * 1978-11-18 1980-05-28 Hoechst Aktiengesellschaft Procédé de préparation de trihalogénures d'organoétain et leur application
FR2458554A1 (fr) * 1979-05-23 1981-01-02 Elf Aquitaine Procede de preparation de trihalogenures organostanniques
EP0021032A1 (fr) * 1979-05-23 1981-01-07 Societe Nationale Elf Aquitaine Procédé de préparation de trihalogénures organostanniques

Also Published As

Publication number Publication date
EP0000747B1 (fr) 1980-06-25
CA1120940A (fr) 1982-03-30
DE2860030D1 (en) 1980-10-30
JPS5430118A (en) 1979-03-06
US4202830A (en) 1980-05-13
IT7826561A0 (it) 1978-08-07
IT1098004B (it) 1985-08-31
DE2735757A1 (de) 1979-02-15

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