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GB815857A - Improvements in and relating to the production of aromatic alcohols - Google Patents

Improvements in and relating to the production of aromatic alcohols

Info

Publication number
GB815857A
GB815857A GB5206/57A GB520657A GB815857A GB 815857 A GB815857 A GB 815857A GB 5206/57 A GB5206/57 A GB 5206/57A GB 520657 A GB520657 A GB 520657A GB 815857 A GB815857 A GB 815857A
Authority
GB
United Kingdom
Prior art keywords
isopropyl benzene
hydroperoxide
sodium
benzene
oxidized
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.)
Expired
Application number
GB5206/57A
Inventor
Derek George Bew
Gordon Howard Whitfield
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of GB815857A publication Critical patent/GB815857A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/04—Phenol
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/10—Methyl-ethyl ketone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

An aromatic hydrocarbon containing one or two nuclear substituents having a structure <FORM:0815857/IV (b)/1> where R1 and R11 are alkyl groups, is partially oxidized to the corresponding hydroperoxide and the hydroperoxide reduced to the corresponding tertiary alcohol without being separated from the unreacted hydrocarbon. It is found that working in this manner it is possible to obtain constant yields of alcohol when the unreacted mixture is subjected to further oxidation and reduction after the oxidized material has been replaced by fresh hydrocarbon and that this treatment may be repeated several times. Compounds such as isopropyl benzene, m- or p-di-isopropyl benzene or m- or p-di-sec.-butyl benzene may be oxidized with air and the hydroperoxide reduced with an alkali metal sulphite, or hydrosulphite or catalytically, e.g. with hydrogen over Raney nickel. The hydroperoxide is preferably reduced using a hot aqueous solution of sodium sulphite containing 10 per cent over the theoretical quantity. In the examples: (1) a feedstock containing p-di-isopropyl benzene with sodium stearate, sodium carbonate and p-di-isopropyl benzene hydroperoxide is heated to 95-98 DEG and air passed through for 8 hours, the product is poured into a hot solution of sodium sulphite and refluxed for 5 hours, p-di-isopropyl benzene a : a 1-diol separates out on cooling, the residue is washed with water and sodium hydroxide and dried and subjected to further oxidation after the original volume is made up with fresh p-di-isopropyl benzene, the cycle is repeated a further six times; (2) a similar experiment is carried out, using three runs, on the meta isomer.
GB5206/57A 1957-02-15 Improvements in and relating to the production of aromatic alcohols Expired GB815857A (en)

Publications (1)

Publication Number Publication Date
GB815857A true GB815857A (en) 1959-07-01

Family

ID=1628238

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5206/57A Expired GB815857A (en) 1957-02-15 Improvements in and relating to the production of aromatic alcohols

Country Status (1)

Country Link
GB (1) GB815857A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420893A (en) * 1963-05-04 1969-01-07 Scholven Chemie Ag Process for the recovery of araliphatic dicarbinols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420893A (en) * 1963-05-04 1969-01-07 Scholven Chemie Ag Process for the recovery of araliphatic dicarbinols

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