GB806961A - Alkylated bis-phenols and hydroxy benzylamines and their method of manufacture - Google Patents

Alkylated bis-phenols and hydroxy benzylamines and their method of manufacture

Info

Publication number
GB806961A
GB806961A GB28488/56A GB2848856A GB806961A GB 806961 A GB806961 A GB 806961A GB 28488/56 A GB28488/56 A GB 28488/56A GB 2848856 A GB2848856 A GB 2848856A GB 806961 A GB806961 A GB 806961A
Authority
GB
United Kingdom
Prior art keywords
butyl
bis
tert
amine
methane
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
GB28488/56A
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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 Ethyl Corp filed Critical Ethyl Corp
Publication of GB806961A publication Critical patent/GB806961A/en
Expired legal-status Critical Current

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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
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • 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
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
    • C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises the use as antioxidants of compounds of general formula <FORM:0806961/III/1> where X is <FORM:0806961/III/2> or <FORM:0806961/III/3> R1 and R2 are C3-C8 alkyl, branched on the alpha atom, R3 is C1-C4 alkyl or <FORM:0806961/III/4> and R4 is hydrogen or C1-C4 alkyl. Compounds specified are 1,1-bis-(3,5-di-tert.-butyl-4-hydroxyphenyl) - methane; 1,1 - bis - (3,5 - diisopropyl - 4 - hydroxyphenyl) - methane; 1,1 - bis - (3 - isopropyl - 5 - tert - butyl - 4 - hydroxyphenyl) - methane; 1,1 - bis - (3,5 - di - (1,1,3,3-tetramethyl-butyl) - 4 - hydroxyphenyl) - methane; 1,1 - bis - (3 - sec. - butyl - 5 - tert. - butyl - 4-hydroxyphenyl methane; N,N - dimethyl - N - (3,5 - diisopropyl - 4 - hydroxybenzyl)-amine; N,N - dimethyl - N - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine; N1-methyl-N,N1 - bis - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine; N,N - di - butyl - N - (3,5 - di-tert - butyl - 4 - hydroxybenzyl) - amine and N - tert. - butyl - N - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine. The compounds may be incorporated in hydrocarbon lubricating oils, steam turbine oils, grease, paraffin wax, linseed oil, cod liver oil, coconut oil, corn oil, lard; gasolines containing lead alkyl anti-knock agents, such as tetraethyl lead; diesel fuels, domestic heating oils, and bunker and residual fuel oils. Suitable amounts of the antioxidant are from about 0.001 to about 3 per cent by weight of the material to be protected.ALSO:The invention comprises the use as antioxidants of compounds of general formula <FORM:0806961/IV (a)/1> where X is <FORM:0806961/IV (a)/2> or <FORM:0806961/IV (a)/3> R1 and R2 are C3-C8 alkyl, branched on the alpha atom, R3 is C1-C4 alkyl or <FORM:0806961/IV (a)/4> and R4 is hydrogen or C1-C4 alkyl. Compounds specified are 1,1-bis-(3,5-di-tert.-butyl-4-hydroxyphenyl) methane; 1,1-bis-(3,5-diisopropyl - 4 - hydroxyphenyl) - methane; 1,1 - bis - (3 - isopropyl - 5 - tert. - butyl - 4 - hydroxyphenyl) - methane; 1,1 - bis - (3,5 - di - (1,1,3,3-tetramethylbutyl) - 4 - hydroxyphenyl) - methane; 1,1 - bis - (3 - sec. - butyl - 5 - tert. - butyl - 4 - hydroxyphenyl) - methane; N,N - dimethyl-N - (3,5 - diisopropyl - 4 - hydroxybenzyl) - amine; N,N - dimethyl - N - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine; N - methyl - N,N - bis - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine; N,N - di - butyl - N - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine and N - tert. - butyl - N - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl)-amine. The compounds may be incorporated in, e.g., natural rubber, polyethylene, polystyrene, and isobutylene-styrene copolymers. Suitable amounts are from about 0.001 to about 3 per cent by weight of the material to be protected.ALSO:The invention comprises compounds of the general formula <FORM:0806961/IV (b)/1> where X is (1) <FORM:0806961/IV (b)/2> or (2) <FORM:0806961/IV (b)/3> R1 and R2 are C3-C8 alkyl groups and are branched on their alpha carbon atoms, R3 is C1-C4 alkyl or <FORM:0806961/IV (b)/4> and R4 is hydrogen or C1-C4 alkyl. The 1,1-bis - (3,5 - dialkyl - 4 - hydroxy phenyl) methanes are prepared by reacting preferably one mol. of formaldehyde with approximately two mols. of a 2,6-dialkyl phenol, in which both alkyl groups contain 3 to 8 carbon atoms, both of said alkyl groups being branched on their alpha carbon atoms, using an alkali metal hydroxide, such as sodium hydroxide as a catalyst. The condensation may be conducted in a solvent consisting of a monohydric alcohol containing 1-8 carbon atoms, preferably isopropyl alcohol, at temperatures between about 20 DEG to about 100 DEG C. The catalyst is present in about 0.5 to about 3 per cent by weight of the dialkyl phenol used. The 3,5-dialkyl - 4 - hydroxybenzyl amines are prepared by reacting a 2,6-dialkyl phenol as defined, formaldehyde, and a primary or secondary amine in which each alkyl group contains from 1 to 4 carbon atoms, in a solvent, preferably a monohydric alcohol containing 1-6 carbon atoms, at a temperature 20-100 DEG C. When preparing the N,N-dialkyl-N - (3,5 - dialkyl - 4 - hydroxy benzyl) - amines, one mol. of formaldehyde and one mol. of a secondary amine are employed per mol. of appropriate 2,6-dialkyl phenol. In the case of N - alkyl - N,N - bis - (3,5 - dialkyl - 4 - hydroxybenzyl)-amines, one mol. of formaldehyde and one half of a mol. of primary amine are used per mol. of dialkyl phenol. When preparing compounds which contain one hydrogen atom and one alkyl group on the nitrogen atom, one mol. of formaldehyde and a large excess of primary amine (about 8 to 10 mols. per mol. of dialkyl phenol) are used in the presence of an excess of a monohydric alcohol solvent. Examples are given of the preparation of 1,1-bis-(3,5-ditert.-butyl-4-hydroxyphenyl)-methane, 1,1-bis-(3,5-di - isopropyl - 4 - hydroxyphenyl) - methane, N,N - dimethyl - N - (3,5 - diisopropyl - 4 - hydroxybenzyl) - amine, N,N - dimethyl - N - (3,5 - di - tert. - butyl - 4 - hydroxy - benzyl) - amine, N - methyl - N,N - bis - (3,5 - di - tert. - butyl - 4 - hydroxybenzyl) - amine. Other compounds mentioned are 1,1-bis-(3-isopropyl-5-tert. - butyl - 4 - hydroxyphenyl) - methane, 1,1 - bis - (3,5 - di - (1,1,3,3 - tetramethylbutyl) - 4 - hydroxyphenyl) - methane, and 1,1 - bis - (3 - sec. - buty. - 5 - tert. - butyl - 4 - hydroxyphenyl)-methane.ALSO:Oxidation of edible oils and fats, e.g. linseed, cod liver, coconut and corn oils, butter and lard, is retarded by incorporation of compounds of the general formula <FORM:0806961/VI/1> where X is <FORM:0806961/VI/2> R1 and R2 are C3-C8 alkyl branched on the alpha atom, R3 is C1-C4 alkyl or <FORM:0806961/VI/3> and R4 is hydrogen or C1-C4 alkyl. Compounds specified are 1,1-bis-(3,5-di-tert-butyl-4-hydroxy-phenyl) methane; 1,1 - bis - (3,5 - di - isopropyl-4 - hydroxyphenyl) methane; 1,1 - bis - (3 - isopropyl - 5 - tert - butyl - 4 - hydroxyphenyl) methane; 1,1 - bis - (3,5 - di - (1,1,3,3 - tetramethylbutyl) - 4 - hydroxyphenyl) methane; 1,1 - bis - (3 - sec. - butyl - 5 - tert - butyl - 4 - hyphoxyphenyl) methane; N1,N1 - dimethyl-N - (3,5 - diisopropyl - 4 - hydroxybenzyl) amine; N,N - dimethyl - N - (3,5 - di - tertbutyl - 4 - hydroxybenzyl) amine; N1 - methylN1,N1 - bis - (3,5 - di - tert - butyl - 4 - hydroxybenzyl) amine; N1,N1-dibutyl-N-(3,5-di-tertbutyl-4-hydroxybenzyl) amine and N-tert-butylN - (3,5 - di - tert - butyl - 4 - hydroxybenzyl) amine. Suitable amounts are from 0.001 to 3 per cent by weight of the material to be protected.
GB28488/56A 1955-09-23 1956-09-18 Alkylated bis-phenols and hydroxy benzylamines and their method of manufacture Expired GB806961A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US806961XA 1955-09-23 1955-09-23

Publications (1)

Publication Number Publication Date
GB806961A true GB806961A (en) 1959-01-07

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB28488/56A Expired GB806961A (en) 1955-09-23 1956-09-18 Alkylated bis-phenols and hydroxy benzylamines and their method of manufacture

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3173952A (en) * 1959-12-24 1965-03-16 Monsanto Co Tris-(3, 5-dialkyl-4-hydroxybenzyl) amines
US5190723A (en) * 1988-02-25 1993-03-02 Ciba-Geigy Corporation Process for inhibiting corrosion
EP1481043A2 (en) * 2000-12-22 2004-12-01 Infineum International Ltd. Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3173952A (en) * 1959-12-24 1965-03-16 Monsanto Co Tris-(3, 5-dialkyl-4-hydroxybenzyl) amines
US5190723A (en) * 1988-02-25 1993-03-02 Ciba-Geigy Corporation Process for inhibiting corrosion
EP1481043A2 (en) * 2000-12-22 2004-12-01 Infineum International Ltd. Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions

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