GB699180A - Improvements in and relating to the stabilisation of organic compounds - Google Patents

Improvements in and relating to the stabilisation of organic compounds

Info

Publication number
GB699180A
GB699180A GB1315550A GB1315550A GB699180A GB 699180 A GB699180 A GB 699180A GB 1315550 A GB1315550 A GB 1315550A GB 1315550 A GB1315550 A GB 1315550A GB 699180 A GB699180 A GB 699180A
Authority
GB
United Kingdom
Prior art keywords
stilbene
dihydroxy
tetra
butyl
stabilized
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
GB1315550A
Inventor
David Gwyn Jones
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
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1315550A priority Critical patent/GB699180A/en
Publication of GB699180A publication Critical patent/GB699180A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • 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
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
    • 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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Organic compounds liable to deterioration from peroxide formation selected from aldehydes, esters of unsaturated carboxylic acids and ethers are stabilized with from 0.001 to 1 per cent by weight of a tetra-alkylated dihydroxy stilbene of the formula <FORM:0699180/IV (b)/1> wherein R1 and R2 represent alkyl groups, preferably containing not more than eight carbon atoms. The dihydroxy stilbene may be 3,31 - dimethyl - 5,51 - ditertiary butyl - 4,41 - dihydroxy stilbene or 3,31,5,51-tetra-tertiary butyl-4,41-dihydroxy stilbene. In the example nonaldehyde is stabilized with each of the two specific dihydroxy stilbenes referred to above. Tetrahydrofuran is referred to as a suitable ether in the Provisional Specification. Specification 699,079 is referred to. Tetra-alkylated dihydroxy stilbenes of the above general formula are prepared by reducing alkyl stilbene quinones of the general formula <FORM:0699180/IV (b)/2> where R1 and R2 have the above significance. The reduction may be carried out with ferrous or stannous chloride with an agent which will liberate nascent hydrogen, e.g. zinc and acetic acid, or by means of catalytic hydrogenation, e.g. in the presence of platinum, palladium, nickel or ruthenium. The compounds 3,31-dimethyl - 4,41 - dihydroxy - 5,51-ditertiary butyl stilbene and 3,31,5,51-tetra-tertiary butyl-4,41 dihydroxy stilbene are prepared from the corresponding stilbene quinones using zinc and glacial acetic acid as the reducing agent.ALSO:Petrols liable to deterioration from peroxide formation are stabilized with from 0.001 to 1 per cent by weight of a tetraalkylated 4, 41-dihydroxy stilbene of the general formula: <FORM:0699180/III/1> wherein R1 and R2 represent alkyl groups, preferably containing not more than eight carbon atoms. In an example, a thermally cracked petrol is stabilized with 3, 31-dimethyl-5, 51-di-tert. butyl-4, 41-dihydroxy stilbene and with 3, 31, 5, 51- tetra tert.-butyl-4, 41-dihydoxy stilbene.
GB1315550A 1950-05-25 1950-05-25 Improvements in and relating to the stabilisation of organic compounds Expired GB699180A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1315550A GB699180A (en) 1950-05-25 1950-05-25 Improvements in and relating to the stabilisation of organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1315550A GB699180A (en) 1950-05-25 1950-05-25 Improvements in and relating to the stabilisation of organic compounds

Publications (1)

Publication Number Publication Date
GB699180A true GB699180A (en) 1953-11-04

Family

ID=10017884

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1315550A Expired GB699180A (en) 1950-05-25 1950-05-25 Improvements in and relating to the stabilisation of organic compounds

Country Status (1)

Country Link
GB (1) GB699180A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITRM20130597A1 (en) * 2013-10-29 2015-04-30 Bridgestone Corp NEW CLASS OF ANTI-AGING AGENTS FOR RUBBER PRODUCTS
WO2015063703A1 (en) * 2013-10-29 2015-05-07 Bridgestone Corporation New class of rubber product anti -aging agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITRM20130597A1 (en) * 2013-10-29 2015-04-30 Bridgestone Corp NEW CLASS OF ANTI-AGING AGENTS FOR RUBBER PRODUCTS
WO2015063703A1 (en) * 2013-10-29 2015-05-07 Bridgestone Corporation New class of rubber product anti -aging agents
CN105682935A (en) * 2013-10-29 2016-06-15 株式会社普利司通 New class of rubber product anti-aging agents
US9908998B2 (en) 2013-10-29 2018-03-06 Bridgestone Corporation Class of rubber product anti-aging agents

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