GB1001351A - Halogenated bisphenols and applications thereof - Google Patents

Halogenated bisphenols and applications thereof

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Publication number
GB1001351A
GB1001351A GB13606/63A GB1360663A GB1001351A GB 1001351 A GB1001351 A GB 1001351A GB 13606/63 A GB13606/63 A GB 13606/63A GB 1360663 A GB1360663 A GB 1360663A GB 1001351 A GB1001351 A GB 1001351A
Authority
GB
United Kingdom
Prior art keywords
specified
lead
materials
adipate
examples
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
GB13606/63A
Inventor
Harold David Orloff
John Peter Napolitano
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
Priority to GB13606/63A priority Critical patent/GB1001351A/en
Publication of GB1001351A publication Critical patent/GB1001351A/en
Expired legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • 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
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
    • 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
    • C10L1/103—Liquid carbonaceous fuels containing additives stabilisation of anti-knock agents
    • 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
    • C10L1/20—Organic compounds containing halogen
    • C10L1/203—Organic compounds containing halogen hydroxyl compounds; ethers, acetals, ketals
    • 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
    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/10—Alcohols; Ethers; Aldehydes; Ketones
    • 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
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2223/04—Phosphate esters
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
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Abstract

As stabilizing agents for organic materials which tend to deteriorate in the presence of air, oxygen or ozone, use is made of the formula <FORM:1001351/C4-C5/1> in which X is chlorine, bromine or iodine (see Division C2). Materials which may be so stabilized include the following:- Animal, vegetable and fish oils and fats.-A number of products which may be stabilized are specified. A synergistic effect is produced by using the stabilizers in association with citric acid, phosphoric acid, ascorbic acid, ethyl acid phosphate, gluconolactone, phytic acid, tartaric acid or aconitic acid. Specific compositions are described in Examples 33-37. Silicone lubricants.-These may be polyalkyl, polyaryl, polyalkoxy or polyaryloxy siloxanes or silanes, a number being specified. Examples 15-19 describe specific compositions. Lubricant greases.-Examples 11, 13 and 14 describe specific compositions. Other materials which may be stabilized are: (1) petroleum products, including gasolenes, mineral lubricating oils, di-ester oils, tricresyl phosphate, hydraulic fluids and hydrocarbon waxes, (2) polyalkylene glycol lubricants prepared from an aliphatic alcohol and an alkylene oxide; (3) chlorinated lubricants, specified compounds being chlorodiphenyls, chloronaphthalenes, chloro-diphenyl oxides and chlorinated paraffin waxes, (4) polymeric fluorocarbon lubricants containing recurring groups -CF2-CF-Cl-, (5) anti-knock compositions containing a lead tetra-alkyl compound and a scavenger, a number of which are specified, and (6) soaps used in the preparation of lubricating greases. The lubricant compositions may contain known additives, a number of which are specified.ALSO:As stabilizing agents for organic materials which tend to deteriorate in the presence of air, oxygen or ozone, use is made of bisphenols of the formula <FORM:1001351/C3/1> in which X is chlorine, bromine or iodine (see Division C2). Materials which may be so stabilized include (1) elastomers, which may be natural or synthetic rubber, a number of types of synthetic rubbers being specified; Examples 38-46 describe natural or synthetic rubber compositions; (2) silicones, which may be polyalkyl, polyaryl, polyalkoxy or polyaryloxy siloxanes or silanes, a number being specified; Examples 15-19 describe specific compositions; (3) polyester resins, (4) polymers of monoolefines, such as polyethylene and polypropylene; (5) epoxide resins, and (6) polystyrene, polyvinyl chloride and polyvinyl acetate.ALSO:The invention comprises bisphenols of the formula <FORM:1001351/C2/1> in which X is chlorine, bromine or iodine. The compounds are obtainable by reacting a 4-halogen-6-tert-butylphenol with formaldehyde in the presence of an alkali-metal hydroxide and a non-aqueous solvent. Details are given in examples 49-51. The products are useful as stabilizing agents for organic materials which tend to deteriorate in the presence of air, oxygen or ozone. Materials which may be so stabilized include the following. Esters having lubricating properties.-A number of acids and alcohols from which such esters can be prepared are specified, and reference is made to the stabilization of diisooctyl azelate, di-(2-ethylhexyl) sebacate, di-sec.-amyl sebacate, diisooctyl adipate, di-(2-ethylhexyl) adipate, di-(2-ethylhexyl) azelate, di - (1 - methyl - 4 - ethyloctyl) glutarate, di-isoamyl adipate, di-(2-ethylhexyl) glutarate, di-(2-ethylbutyl) adipate, di-tetradecyl sebacate, di-(2-ethylhexyl) pinate, diethyl oxalate, di-sec.-butyl malonate, di-(2-hexyl) succinate, diisoheptyl pimelate, di-(3-decyl) suberate, di-sec.-amyl glutarate, diisobutyl glutarate, di - (2 - ethylbutyl) glutarate, di - (3 - methylbutyl) adipate, diethyl adipate, di-sec.-amyl azelate, diisobutyl azelate and di-sec-butyl sebacate. Organic phosphoric acid esters of the general formula OP(OR)(OR1)(OR11), in which R, R1 and R11 are hydrogen or organic radicals, at least one being an organic radical. Example 25 describes the stabilization of tricresyl phosphate. Other phosphoric esters which may be treated are also specified. Organic lead compounds for use in anti-knock compositions. Specified compounds are tetramethyl lead, tetraethyl lead, tetrapropyl lead, dimethyldiethyl lead, trimethylethyl lead and triethyl lead bromide. Other materials which may be stabilized include chlorinated lubricants, specified compounds being chlorodiphenyls, chloronaphthalenes, chlorodiphenyl oxides and chlorinated paraffin waxes.
GB13606/63A 1963-04-05 1963-04-05 Halogenated bisphenols and applications thereof Expired GB1001351A (en)

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GB13606/63A GB1001351A (en) 1963-04-05 1963-04-05 Halogenated bisphenols and applications thereof

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991009096A2 (en) * 1989-12-09 1991-06-27 Henkel Kommanditgesellschaft Auf Aktien Non-volatile solvent for aroma-containing active ingredients
WO2004018402A1 (en) * 2002-08-20 2004-03-04 The University Of Sheffield Aldehyde phenol condensates
EP1651741A2 (en) * 2003-06-26 2006-05-03 Oryxe Energy International, Inc. Novel hydrocarbon fuel additives and fuel formulations exhibiting improved combustion properties
WO2015171292A1 (en) * 2014-05-08 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
US9944877B2 (en) 2014-09-17 2018-04-17 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991009096A2 (en) * 1989-12-09 1991-06-27 Henkel Kommanditgesellschaft Auf Aktien Non-volatile solvent for aroma-containing active ingredients
WO1991009096A3 (en) * 1989-12-09 1991-07-25 Henkel Kgaa Non-volatile solvent for aroma-containing active ingredients
WO2004018402A1 (en) * 2002-08-20 2004-03-04 The University Of Sheffield Aldehyde phenol condensates
EP1651741A2 (en) * 2003-06-26 2006-05-03 Oryxe Energy International, Inc. Novel hydrocarbon fuel additives and fuel formulations exhibiting improved combustion properties
EP1651741A4 (en) * 2003-06-26 2011-05-25 Oryxe energy int inc Novel hydrocarbon fuel additives and fuel formulations exhibiting improved combustion properties
WO2015171292A1 (en) * 2014-05-08 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
US9896634B2 (en) 2014-05-08 2018-02-20 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
US9944877B2 (en) 2014-09-17 2018-04-17 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines

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