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DE1117577B - Process for the production of organotin hydrides - Google Patents

Process for the production of organotin hydrides

Info

Publication number
DE1117577B
DE1117577B DEK36144A DEK0036144A DE1117577B DE 1117577 B DE1117577 B DE 1117577B DE K36144 A DEK36144 A DE K36144A DE K0036144 A DEK0036144 A DE K0036144A DE 1117577 B DE1117577 B DE 1117577B
Authority
DE
Germany
Prior art keywords
organotin
hydrides
aluminum
production
organotin hydrides
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
Application number
DEK36144A
Other languages
German (de)
Inventor
Dr Herbert Jenkner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kali Chemie AG
Original Assignee
Kali Chemie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kali Chemie AG filed Critical Kali Chemie AG
Priority to DEK36144A priority Critical patent/DE1117577B/en
Priority to FR808562A priority patent/FR1246364A/en
Priority to GB36811/59A priority patent/GB871642A/en
Publication of DE1117577B publication Critical patent/DE1117577B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
    • C10L1/308—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond) organo tin compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B6/00—Hydrides of metals including fully or partially hydrided metals, alloys or intermetallic compounds ; Compounds containing at least one metal-hydrogen bond, e.g. (GeH3)2S, SiH GeH; Monoborane or diborane; Addition complexes thereof
    • 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
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/064—Aluminium compounds with C-aluminium linkage compounds with an Al-Halogen linkage
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)

Description

Es ist bekannt, Organozinnhydride aus Organozinnhalogeniden und komplexen Aluminium- oder Borhydriden herzustellen. Durch Umsetzung von Trimethylzinnchlorid mit Lithiumaluminiumhydrid beispielsweise gelangt man zum Trimethylstannan. Komplexe Aluminium- oder Borhydride sind jedoch zu teure Hydrierungsmittel, als daß sie im großtechnischen Verfahren zur Anwendung kommen könnten.It is known to produce organotin hydrides from organotin halides and to produce complex aluminum or boron hydrides. By reacting trimethyltin chloride with lithium aluminum hydride for example, one arrives at trimethylstannane. However, complex aluminum or boron hydrides are hydrogenating agents that are too expensive to be used in large-scale industrial processes could.

Es wurde nun gefunden, daß Organozinnhydride in hoher Ausbeute und großer Reinheit durch Umsetzung von Organozinnhalogeniden, insbesondere von Organozinnchloriden, und Alkylaluminiumhydriden gewonnen werden können, obwohl bekannt ist, daß Organozinnhalogenide durch Alkylaluminiumverbindungen alkyliert werden. Als Alkylaluminiumhydrid wird ein Aluminiummonohydrid oder ein Aluminiumdihydrid mit zwei oder einem Alkylrest am Aluminium verstanden, wobei es sich um niedere Alkylreste gleicher oder verschiedener Art handelt, wie Methyl, Äthyl, Propyl und Isobutyl. Da Alkylaluminiumhydride leicht aus der Reaktion von Aluminiumtrialkyl mit Aluminium und Wasserstoff erhältlich sind, ist nunmehr auch die Herstellung von Organozinnhydriden preisgünstig zu gestalten.It has now been found that organotin hydrides in high yield and high purity by reaction of organotin halides, especially organotin chlorides, and alkyl aluminum hydrides can be obtained, although organotin halides are known to be obtained by alkyl aluminum compounds be alkylated. As the alkyl aluminum hydride, aluminum monohydride or Aluminum dihydride with two or one alkyl radical on aluminum, which is lower Alkyl residues of the same or different types act, such as methyl, ethyl, propyl and isobutyl. As alkyl aluminum hydrides are easily obtainable from the reaction of aluminum trialkyl with aluminum and hydrogen, the production of To make organotin hydrides inexpensive.

Die Umsetzung verläuft entsprechend der nachfolgenden Gleichung:The implementation proceeds according to the following equation:

Verfahren zur Herstellung
von OrganozinnhydridenMethod of manufacture
of organotin hydrides

-Z +-Z +

R bedeutet darin einen beliebigen organischen Rest, wie gesättigten oder ungesättigten aliphatischen oder aromatischen, gegebenenfalls substituierten Kohlenwasserstoffrest, R' einen niederen Alkylrest, χ = 1,2 oder 3 und y = 1 oder 2 sowie Hai = Halogen, vorzugsweise Chlor.R denotes any organic radical, such as saturated or unsaturated aliphatic or aromatic, optionally substituted hydrocarbon radical, R 'a lower alkyl radical, χ = 1, 2 or 3 and y = 1 or 2 and Hal = halogen, preferably chlorine.

Die Reaktion tritt bereits bei verhältnismäßig tiefen Temperaturen von —20 bis 50°C mit ausreichender Geschwindigkeit ein. Dabei ist die Mit-Verwendung eines indifferenten Lösungsmittels besonders vorteilhaft, wenn auch nicht in allen Fällen erforderlich. Als Hydrierungsmittel wird bevorzugt vom Dialkylaluminiumhydrid ausgegangen, da sich Alkylaluminiumdihydrid leicht zersetzt.The reaction occurs at relatively low temperatures of -20 to 50 ° C with sufficient Speed one. The co-use of an inert solvent is particularly important advantageous, although not required in all cases. The preferred hydrogenating agent is started from dialkyl aluminum hydride, since alkyl aluminum dihydride decomposes easily.

Organozinnhydride können als Stabilisatoren für Kunststoffe, als Katalysatoren, als Treibstoffzusätze oder aber zur Herstellung von funktionellen Organozinnverbindungen verwendet werden.Organotin hydrides can be used as stabilizers for plastics, as catalysts, as fuel additives or they can be used for the production of functional organotin compounds.

Anmelder:Applicant:

Kali-Chemie Aktiengesellschaft,
Hannover, Hans - Böckler -Allee 20Kali-Chemie Aktiengesellschaft,
Hanover, Hans - Böckler - Allee 20

Dr. Herbert Jenkner, Hannover-Wülfel,
ist als Erfinder genannt wordenDr. Herbert Jenkner, Hanover-Wülfel,
has been named as the inventor

Beispielexample

In eine Lösung von 20 Gewichtsteilen Diäthylaluminiumhydrid in 50 Gewichtsteilen Diäthylenglykoldimethyläther wurde eine Lösung von 24 Gewichtsteilen Diäthylzinndichlorid in 40 Gewichtsteilen des gleichen Äthers zugetropft. Bei einer Temperatur zwischen 0 und 300C lief die Reaktion ab. Durch Vakuumdestillation wurden 15,6 Gewichtsteile Diäthylstannan (C2H5)2SnH2 erhalten, was einer Ausbeute von über 90% der Theorie entsprach. A solution of 24 parts by weight of diethyltin dichloride in 40 parts by weight of the same ether was added dropwise to a solution of 20 parts by weight of diethyl aluminum hydride in 50 parts by weight of diethylene glycol dimethyl ether. The reaction took place at a temperature between 0 and 30 ° C. 15.6 parts by weight of diethylstannane (C 2 H 5 ) 2 SnH 2 were obtained by vacuum distillation, which corresponded to a yield of over 90% of theory.

Claims (2)

Patentansprüche:Patent claims: 1. Verfahren zur Herstellung von Organozinnhydriden, dadurch gekennzeichnet, daß Organozinnhalogenide mit niederen Alkylaluminiumhydriden umgesetzt werden.1. A process for the preparation of organotin hydrides, characterized in that organotin halides are reacted with lower alkyl aluminum hydrides. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß als Hydrierungsmittel Dialkylaluminiumhydrid verwendet wird.2. The method according to claim 1, characterized in that dialkylaluminum hydride is used as the hydrogenating agent is used. In Betracht gezogene Druckschriften:
Deutsche Patentschrift Nr. 918 928;
deutsche Auslegeschrift Nr. 1 038 553;
Angewandte Chemie, 1958, S. 305;
Österreichische Chemikerzeitung, 1956, S. 136;
Journal of the American Chemical Society, 1947, S. 2692 bis 2695.Considered publications:
German Patent No. 918 928;
German interpretative document No. 1 038 553;
Angewandte Chemie, 1958, p. 305;
Österreichische Chemikerzeitung, 1956, p. 136;
Journal of the American Chemical Society, 1947, pp. 2692-2695. 109 740/571 11.61109 740/571 11.61
DEK36144A 1958-11-05 1958-11-05 Process for the production of organotin hydrides Pending DE1117577B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEK36144A DE1117577B (en) 1958-11-05 1958-11-05 Process for the production of organotin hydrides
FR808562A FR1246364A (en) 1958-11-05 1959-10-27 Process for the preparation of organohydride of tin hydrides
GB36811/59A GB871642A (en) 1958-11-05 1959-10-29 Method of producing hydrides of tin

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK36144A DE1117577B (en) 1958-11-05 1958-11-05 Process for the production of organotin hydrides

Publications (1)

Publication Number Publication Date
DE1117577B true DE1117577B (en) 1961-11-23

Family

ID=7220592

Family Applications (1)

Application Number Title Priority Date Filing Date
DEK36144A Pending DE1117577B (en) 1958-11-05 1958-11-05 Process for the production of organotin hydrides

Country Status (3)

Country Link
DE (1) DE1117577B (en)
FR (1) FR1246364A (en)
GB (1) GB871642A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1167345B (en) 1960-11-08 1964-04-09 Studiengesellschaft Kohle Mbh Process for stabilizing organotin hydrides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918928C (en) * 1952-04-21 1954-10-07 Dr Karl Ziegler Process for the preparation of alkyl aluminum hydrides
DE1038553B (en) * 1954-11-12 1958-09-11 Kali Chemie Ag Process for the production of silicon compounds which contain at least one hydrogen atom on silicon

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918928C (en) * 1952-04-21 1954-10-07 Dr Karl Ziegler Process for the preparation of alkyl aluminum hydrides
DE1038553B (en) * 1954-11-12 1958-09-11 Kali Chemie Ag Process for the production of silicon compounds which contain at least one hydrogen atom on silicon

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1167345B (en) 1960-11-08 1964-04-09 Studiengesellschaft Kohle Mbh Process for stabilizing organotin hydrides

Also Published As

Publication number Publication date
GB871642A (en) 1961-06-28
FR1246364A (en) 1960-11-18

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