Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides

Definitions

• the present invention comprises a process for the preparation of dialkyl sulfoxides wherein an alkylaluminum compound is dissolved in a hydrocarbon solvent, cooled, and then thionyl chloride also dissolved in a hydrocarbon solvent preferably the same solvent as used for the alkylaluminum compound is added thereto. After all the thionyl chloride has been added, the reaction mixture is heated during which period the system is maintained under an atmosphere of an inert gas. Upon completion of the reaction, the reaction mixture is cooled and the dialkyl sulfoxide recovered. While the procedure described above is generally preferred, equally satisfactory results can be obtained by adding the alkylaluminum solution to the thionyl chlo ride solution.
• Suitable trialkylaluminum compounds include trimethyl, triethyl, tn'propyl, etc., aluminum compounds. I prefer to employ trialkylaluminum compounds wherein the alkyl group contains from 1 to 18 carbon atoms, but compounds can be used wherein the alkyl group contains a larger number of carbon atoms. In addition to trialkyl aluminum compounds, other aluminum organo (alkylaluminum) compounds may be used, such as those identified by the general formulas AlR Cl and R AIOR 2 wherein the Rs represent alkyl radicals containing from 1 to 18 or more carbon atoms. The alkyl groups of these compounds may be the same or different.
• Suitable solvents for dissolving the dialkyl-aluminum compound and the thionyl chloride include aromatic and aliphatic hydrocarbons and others. I prefer to employ a solvent that has a boiling point sufiiciently low so that it can be readily-removed from the other components the reaction mixture by distillation but high enough that losses through evaporation are not excessive. Also, if the solvent has a low boiling point it will form explosive mixtures with air readily and as a consequence the use of such a compound can be hazardous. As a rule, suitable solvents are those l aving boiling points within the range of about 30 to 200 C. I prefer to use solvents having boiling points within the range of about 40 to C. It is not necessary to use a pure hydrocarbon as mixtures are satisfactory.
• the reaction is carried out in the absence of air, land this is accomplished by maintaining the entire reaction under an atmosphere of an inert gas. Suitable gases for this purpose include any gas that will not react with any of the reactants present. This will include the noble gases and nitrogen.
• the initial reaction is carried out at a relatively low temperature. Suitable and preferred temperature ranges for this initial reaction vary from -25 to C. and from 0 to.30 C. respectively. Following the initial reaction,.th-at is after all the thionyl chloride has been added, the temperature is raised. Suitable and preferred temperature ranges for this second reaction vary from 0 to 100 C. and from 30 to 80 C., respectively.
• R represents an alkyl radical
• Example 1 To a reaction vessel in which the air was replaced with nitrogen was added a solution consisting of 87 parts by weight of tri-n-octyl-aluminum in 100 parts by volume of n-hexane. A solution consisting of 35.6 parts by weight of thionyl chloride in 70 parts by. volume of nhexane was then slowly added to the contents in the reaction vessel during which time the temperature was maintained between 0 and 10 C. After the addition of the thionyl chloride solution was completed, the mixture was heated to a temperature of 67 C. and then allowed to stand overnight.
• reaction mixture was then poured over cracked ice (300 parts by weight) and the di-(n-octyl) sulfoxide removed from the reaction mixture by extraction with warm n-hexane.
• the sulfoxide was recovered from the n-hexane by evaporating the latter. A total of 42.8 parts of di-(n-octyl) sulfoxide was obtained.
• Example 2 The procedure of Example 1 was followed with the exception that 25 parts of triethylaluminum was substihired for 'the tri-n-octylaluminum used in Example 1. A good yield of diethyl sulfoxide was obtained.
• the sul-foxides produced in accordance with my inven tion are particularly useful as oxidation inhibitors in lubricating oils and to raise the octane number of diesel fuels.
• a method of preparing a dialkyl sulfoxide which comprises dissolving an alkylaluminum compound in an inert organic solvent maintaining the resulting solution at a temperature varying from '25 to 100 C. under an atmosphere of an inert gas, adding to said solution thionyl chloride dissolved in an inert organic solvent, heating the resulting mixture to a temperature varying from to 100 C., cooling said mixture and then recovering the dialkyl sulfoxide.
• a method of preparing a dialkyl sulfoxide which comprises dissolving an alkylaluminum compound in an inert organic solvent maintaining the resulting solution 'at a temperature varying from 0 to 30 C. and under an atmosphere of an inert gas, adding to said solution thionyl chloride dissolved in an inert organic solvent, heating the resulting mixture to a temperature varying from 30 to C., cooling said mixture and then recovering the dialkyl sulfoxide.
• alkylaluminum compound is trialkylaluminum compound, wherein the alkyl groups of said trialkylaluminum contains from 1 to 18 carbon atoms.
• alkylalum-inum compound is a dialkylaluminum chloride.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (6)

• 1959
  • 1959-08-20 US US834959A patent/US2947787A/en not_active Expired - Lifetime
• 1960
  • 1960-06-15 GB GB21007/60A patent/GB940381A/en not_active Expired
  • 1960-06-28 BE BE592357A patent/BE592357A/fr unknown

Non-Patent Citations (1)

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