Classifications

• • A—HUMAN NECESSITIES
  • A42—HEADWEAR
  • A42C—MANUFACTURING OR TRIMMING HEAD COVERINGS, e.g. HATS
  • A42C1/00—Manufacturing hats
  • A42C1/02—Making hat-bats; Bat-forming machines; Conical bat machines; Bat-forming tools
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C407/00—Preparation of peroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C409/00—Peroxy compounds
  • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
  • C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
  • C07C409/08—Compounds containing six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C409/00—Peroxy compounds
  • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
  • C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
  • C07C409/08—Compounds containing six-membered aromatic rings
  • C07C409/10—Cumene hydroperoxide
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C409/00—Peroxy compounds
  • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
  • C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
  • C07C409/08—Compounds containing six-membered aromatic rings
  • C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring

Definitions

• This invention is for improvements in or relating to the production of the hydroperoxides of cumene and its homologues. More particularly, this invention is concerned with the conversion of cumene and homologous alkyl-aromatic hydro carbons into the corresponding hydroperoxides by oxidation. According to the literature, this oxidation can be effected with excellent yield by treatment of the hydrocarbon with oxygen at 85 C.
• the oxidation of cumene and other homologous .alkyl-aromatic hydrocarbons such as p-cymene, di-isopropyl benzene, iso'butyl benzene (i. e. a-methyln-propyl benzene) and ethyl benzene by means of oxygen or an oxygen-containing gas such as air, is effected in the presence as catalyst of a member of the class consisting of alkali and alkalineearth metal formates, oxalates and benzoates.
• the proportion of catalyst employed may vary within fairly wide limits depending to some extent upon the operating conditions chosen, the optimum amount being determinable by simple preliminary test. It is usually advantageous to introduce the catalyst in portions during the course of the operation.
• the oxidation of the aforesaid hydrocarbons in the presence of a catalyst in accordance with the present invention is preferably carried out under the conditions generally adopted heretofore in the preparation of the hydroperoxides of hydrocarbons. More especially, and in conformity with a common practice in oxidation of this nature, there may be added at the very commencement of the process a small quantity of a hydroperoxide for the purpose of initiating the reaction.
• This hydroperoxide may be, for example, the hydroperoxide of the hydrocarbon to be oxidised, obtained from a prior operation.
• Example I I The operation of Example I is repeated, but at atmospheric pressure and with an air supply of 180 litres per hour.
• l g. of sodium formate is added at the commencementand a further 9.5 g. per hour is added in at the end 95 each successive heur.
• Example III The operation of Example I is repeated, but with oxygen instead of air.
• 2 g. are added at the start,
• the purity of the hydroperoxide of the 17.2% solution obtained after 8 hours without formate is 90.5%, and the purity of the hydroperoxide of the 20.1% solution obtained after 4 hours with formate (chosen to provide a more accurate comparison) is 93.5%. Therefore, for a comparable proportion of hydroperoxide, 50% more of byproducts were obtained in the absence of formate.
• Example IV the cumene is employed in the form of a suspension in water. 827 parts of cumene, 51.5% parts of a 35.5% solution of cumene hydroperoxide in cumene and 1000 parts of water (all the parts being parts by volume) are introduced into the oxidation vessel. The operation is carried out at 85 C. and eleven parts by volume of oxygen per hour are introduced. The quantity of sodium formate added corresponds to 1.5% of the water added.
• Example V The operation is the same as in Example III but the sodium formate is replaced by the same quantities of calcium formate.
• the purity of the product prepared without 0 formate is 90%.
• the purity of the product of twice the concentration, prepared in the presence of calcium formate, is 93%.
• Example VI 220 litres of air are bubbled under a pressure of 12 kg. into 2700 cc. of cumene heated at 110 (3., to which 68 g. of cumene hydroperoxide have been added in order to eliminate the period of induction.
• Example VII 600 cc. of p-cymene containing g. of 68% pcymene hydroperoxide to eliminate the period of induction are mixed with 3 g. of sodium formate. 20 litres of oxygen per hour are passed at 120 C. into the liquid for seven hours. A solution of pcymene containing 16% of p-cymene hydroperoxide is obtained. The small quantity of isopropylbenzoic acid simultaneously formed during the oxidation is separated by washing with a dilute solution of sodium carbonate. The yield of p-cymene hydroperoxide is from 80% to 85% calculated on the weight of p-cymene consumed. the remaining percentage consisting of isopropylbenzoic acid, dimethyl p-methyl-phenylcarbinol and p-methylacetophenone.
• Example VIII Into 250 cc. of a-methyl-n-propyl benzene containing 5 g. of a-methyl-n-propyl benzene hydroperoxide and 1 g. of sodium formate are passed litres of oxyen per hour at 110 C. for 17 hours. A 14.9% solution of a-methyl-n-propyl benzene hydroperoxide in a-methyl-n-propyl benzene is obtained.
• the yield of hydroperoxide is from 80% to 85% calculated on the quantity of a-methyl-n-propyl benzene consumed.
• Process for the production of alkyl-aromatic hydroperoxides which comprises bringing a member of the class consisting of cumene, pcymene, di-isopropyl benzene and a-methyl-m propyl benzene into contact with oxygen at ele-- vated temperature in the presence of a hydroperoxide and of calcium formate as catalyst.
• Process for the production of alkyl-aromatic hydroperoxides which comprises bringing a member of the class consisting of cumene, pcymene, di-isopropyl benzene and oc-l'XlGiJhYl-ilpropyl benzene into contact with oxygen at elevated temperature in the presence of a hydro peroxide and of sodium oxalate as catalyst.
• Process for the production of alkyl-aromatic hydroperoxides which comprises bringing a member of the class consisting of cumene, pcymene, di-isopropyl benzene and eL-lTlGiihYl-Ilpropyl benzene into contact with oxygen at ele- 7 vated temperature in the presence of a hydroperoxide and of calcium oxalate as catalyst.
• Process for the production of alkyl-aromatic hydroperoxides which comprises bringing a member of the class consisting of cumene, pcymene, di-isopropyl benzene and a-methyl-npropyl benzene into contact with oxygen at elevated temperature in the presence of a. hydroperoxide and of sodium benzoate as catalyst.

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  • US US24036D patent/USRE24036E/en not_active Expired
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  • 1949-11-30 CH CH280451D patent/CH280451A/fr unknown
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