US2633425A - Stabilization of organic compounds - Google Patents
Stabilization of organic compounds Download PDFInfo
- Publication number
- US2633425A US2633425A US185336A US18533650A US2633425A US 2633425 A US2633425 A US 2633425A US 185336 A US185336 A US 185336A US 18533650 A US18533650 A US 18533650A US 2633425 A US2633425 A US 2633425A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- tetrahydronaphthalene
- dihydronaphthalene
- amino
- oil
- 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 - Lifetime
Links
- 150000002894 organic compounds Chemical class 0.000 title description 5
- 230000006641 stabilisation Effects 0.000 title description 5
- 238000011105 stabilization Methods 0.000 title description 5
- -1 1,4-DIAMINO-5,8-DIHYDRONAPHTHALENE Chemical compound 0.000 claims description 33
- 239000003112 inhibitor Substances 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 16
- 230000006866 deterioration Effects 0.000 claims description 11
- 239000011368 organic material Substances 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 3
- OKGJUCMRAGHHTB-UHFFFAOYSA-N 4-amino-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1CCCC2=C1C(O)=CC=C2N OKGJUCMRAGHHTB-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- FAJBOTIRBFAKPK-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-1,4-diamine Chemical compound C1CCCC2=C1C(N)=CC=C2N FAJBOTIRBFAKPK-UHFFFAOYSA-N 0.000 claims 1
- 239000003502 gasoline Substances 0.000 description 11
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000006308 propyl amino group Chemical group 0.000 description 3
- FUPIVZHYVSCYLX-UHFFFAOYSA-N 1,4-dihydronaphthalene Chemical compound C1=CC=C2CC=CCC2=C1 FUPIVZHYVSCYLX-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- GVTDRUXHMYZTFF-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-1,4-diol Chemical compound C1CCCC2=C1C(O)=CC=C2O GVTDRUXHMYZTFF-UHFFFAOYSA-N 0.000 description 1
- XISXRVFRLOWUBM-UHFFFAOYSA-N 5,8-dihydronaphthalen-1-amine Chemical compound C1C=CCC2=C1C=CC=C2N XISXRVFRLOWUBM-UHFFFAOYSA-N 0.000 description 1
- LZODMDMDIZUSHT-UHFFFAOYSA-N 5,8-dihydronaphthalene-1,4-diol Chemical compound C1C=CCC2=C1C(O)=CC=C2O LZODMDMDIZUSHT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000010480 babassu oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 235000005473 carotenes Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
- C11B5/005—Amines or imines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and 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
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/402—Castor oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/066—Arylene diamines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- organic compounds are unstable in storage or during treatment and form undesirable gums, undergo discoloration, form sludges or otherwise deteriorate due to oxidation, polymerization or other undesired reactions. Included among the organic compounds which undergo such deterioration are gasoline, diesel oil, mineral oil, lubricating oil, fuel oil, drying oil, greases, edible fats and oils, acetylenes and particularly vinyl acetylene, butadiene, isoprene, styrene and other vinyl aromatics, various unsaturated alcohols, acids, ketones, etc.
- the invention is particularly applicable to the stabilization of unsaturated gasolines and still more particularly cracked and polymer gasolines. In storage or during treatment these unsaturated gasolines tend to form undesirable gums.
- the invention is also applicable to the treatment of aviation gasolines which tend to undergo deterioration due to the addition of tetraethyl lead fluid or due to other components in the gasoline.
- the invention is also particularly applicable to the stabilization of edible fats and oils which generally are of animal or vegetable origin and which tend to become rancid, especially during long periods of storage prior to use.
- Typical representatives of these edible fats and oils include linseed oil, menhaden oil, cod liver oil, castor oil, olive oil, rapeseed oil, coconut oil, palm oil, corn oil, sesame oil, peanut oil, babassu oil, butter, fat, lard, beef tallow, etc. It is understood that other oils and fats may be treated within the scope of the present invention, including oils and fats which have previously been subjected to various treatments, such as blowing with air heat treatment, etc.
- the present invention is particularly applicable to the treatment of crops by dusting or spraying in order to preserve food accessory factors such as carotene, vitamins, various fatty acids, alcohols, etc.
- the present invention relates to an organic material subject to oxidative deterioration containing an inhibitor prepared by reacting an aliphatic amine with a member of the group consisting of 1,4-dihydroxy-5,8-dihydronaphthalene and 1,4-dihydroxy-5,6,7,8-tetrahydronaphthalene.
- the present invention relates to motor fuel normally tending to deteriorate in storage containing from about 0.001% to about 0.5% by weight of N-sec-butyl-N-methyl-lhydroxy-4-amino-5,6,7,8-tetrahydronaphthalene.
- novel inhibitors of the present invention may be represented by the following general structure:
- R, R1, R2, R3, R4, and R5 may comprise hydrogen or alkyl radicals.
- these groups comprise alkyl radicals, they preferably are selected so that the total number of carbon atoms in the inhibitor does not exceed about 25 Still more particularly, these compounds preferably comprise alkyl radicals containing from about 1 to about 4 carbon atoms and include such groups as methyl, ethyl, propyl and butyl.
- R. comprises an alkyl group and comprise such compounds as 1-hydroxy-4-methylamino- 5,8 dihydronaphthalene, 1 hydroxy 4 -ethylamino 5,8 dihydronaphthalene, 1 hydroxy- 4 propylamino 5,8 dihydronaphthalene, 1- hydroxy 4 butylamino 5,8 dihydronaphthalene, 1 hydroxy 4 dimethylamino 5,8 dihydronaphthalene, 1 hydroxy 4 diethylamino 5,8 dihydronaphthalene, 1 hydroxy- 4 dipropylamino 5,8 dihydronaphthalene, 1 hydroxy 4 dibutylamino 5,8 -dihydronaphthalene, N ethyl N methyl 1 hydroxy- 4 amino 5,8 dihydronaphthalene, N propyl- N methyl 1 hydroxy 4 amino 5,8 dihydronaphthalene, N propyl- N methyl 1 hydroxy 4 amino 5,8 dihydronaphthalene, N propyl- N
- Structure II illustrates a 1,4-diamino-5,8-dihydronaphthalene.
- Preferred inhibitors in this class include 1,4 diamino 5,8 dihydronaphthalene, 1,4 dimethylamino 5,8 dihydronaphthalene, 1,4 diethylainino 5,8 dihydronaphthalene, 1,4 dipropylamino 5,8 dihydronaphthalene, 1,4 dibutylamino 5,8 dihydro naphthalene, 1 methyl amino 4 ethylamino 5,8 dihydronaphthalene, 1 methylamino 4 propylamino 5,8 '--dihydronaphthalene, 1 methylamino 4 butylamino 5,8,- dihydronaphthalene, 1-ethylamino 4* propylamino 5,8 dihydronaphthalene, 1 ethylamino 4 1-- butylamino.-.
- Preferred inhibitors ofthis class include l-hydroxy-l-methylamino-5,6,7 ⁇ e tetrahydronapthalene, 1 hydroxy-4 ethylamino-5,6,'7,8 tetrahydronaphthalene, 1-hydroxy-4-propylamino-5 ⁇ 6,7,8-tetrahydronaphthalene, .ij1-hydroxy-4-butylamino-5,6,- 7,8 tetrahydronaphthalene; 1'--- hydroxy4-dimethylamino-5,6;7,8-- tetrahydronaphthalene, 1- hydroxy-l-diethylamino 5,6,'7-,8 tetrahydronaphthalene, 1-hydroxy-4-dipropylamino-5,6,7,8 tetrahydronaphthalene, 1-hydroXy'-.4 dibutylamino-5,6,7,8-tetrahydronaphthalene, N- ether- N methyl
- StructureIV illustrates a l,4-diamino-5,6,7,8- tetrahydronaphthalene.
- inhibitors of this class include 1,4-1diamino-5,6;7,8-tetrahydronaphthalene, 1,4-dimethylamino 5,6,'7,8 tetrahydronaphthalene; "1,4 1- diethylamino 5,637,8- tetrahydronaphthalene, 1,4-dipropylamino-5;6,7- S-tetrahydrpnaphthalene,.
- the 'compoundshereinbefore set forth comprise preferred"inhibitors and that compounds ofthese general structures otherwise substituted by suitable 'groups'are also included within 'the scope'qf; the present invention.
- preferred inhibitors include those in which one or both 0;) ,tliehydrogenatoms attached to each nitrogen atoinare replaced by alkyl groups.
- Specificexam'ples of compounds of 'this class are specified in the list of preferred compounds of'th'e classillu'strated general Structures I and III.
- Similar di-substituted compounds of the diamino compounds illustrated by general Structures II and IV are comprised within the scope of the present invention.
- it is preferred that the total number of carbon atoms in the inhibitors does not exceed about 25. r
- the inhibitors of the present invention may comprise the specific compounds named herein in admixture with various isomers thereof.
- the isom'ers may comprise corresponding compounds in which the double bond in the non-aromaticringhas shifted to a conjugated position and/or those in which the hydroxy and amino groupshave interchanged positions with respect to'an' a'lkyl group positioned on the nonaro'rnatic ring.
- the isomers will be of the latter type.
- Th'e'inhibitors of the present invention may be prepared in any suitable manner.
- these'inhibitors are prepared by the reaction of a 1,4 dihydroxy 5,ii-dihydronaphthalene or IA-dihydroXy- 5,-6;;7 -tetrahydronaphthalene with a suitablealiphatic amine';
- Suitable aliphatic amines include methyl amine; ethyl amine, propyl amine, isopropyl amine, -n-butyl amine, isobutyl amine, -sec-bu'tylamine, etc;
- the reaction is generally effected b'yheat-ing the reactants at an elevated temperature andrecoverin'g'the products by extraction in suitable solvents;
- a specific method'of preparationis hereinafterset-forth are examples of the reactants at an elevated temperature andrecoverin'g'the products by extraction in suitable solvents.
- 1 ,4-dihydr6Xy- 5,8 diliydronaph'thalne maybe heatedin-asealed tubewitHsec-butyl in'e-at an elevated temperature of about-2005C.
- diall'zylaminobb'inpdiind is ifis'iredth'e amount of secuty1amine and tne reaeuon time are in creased'in-- order 'to efit reaction of the amine Withbo'l'il'i'of the hydi 'ify groups;- After 't-he reaction has proceeded tb -th desired extent, the product-ma be" dissolvd in an organic solvent, such as ethe -pet rq1eumetner; and then extracted vvith a dilut'eadueoiis sodium hydroxide solution to remov th iinracted 'startihg material.
- the other alkylaznino substituted' compounds may be' 'pr'epared ina'simil'ar mannenby varying the starting reagents as desired; Similarly the tetrahydro-substituted compounds are made in substantially the same man-- her by "starting with 1,4 di-hydroxy-5,6,'Z,8-tetraliydronaphtha'lehel r F
- a suitablealkylation agent such as dim'ethyl 'suliata' diethyl 1 sulfate, propyl chloride, etci in order'toproduce the dethe inhibitor may be used in conjunction with a synergist, such as phosphoric acid, ascorbic acid, citric acid, etc.
- inhibitors of the present invention increased the induction period from 100 minutes to at least 285 minutes and that the last mentioned compound, which comprised a tertiary amine, increased the induction period to 650 minutes.
- the inhibitor of the present invention therefore preferably contains a tertiary amine grouping.
- EXAMPLE II The inhibitors used in the following run were prepared in a manner similar to that heretofore set forth. These inhibitors were added to lard which had a normal stability period of 9 hours as determined by the Swift test. This test is described in detail in the article by A. E. King, H. L. Roschen and W. H. Irwin, which appeared in the Oil and Soap, vol. X, No. 6, pages 105 to 109 (1933). In general, this test comprises bubbling air through a sample of the lard and reporting the number of hours until the lard develops a peroxide value of 20. 0.02% by weight of the inhibitors were added to this sample of the lard and gave the results as shown in Table II.
- An organic material normally subject to oxidative deterioration containing, as an inhibitor for said deterioration, a small amount of. an inhibiting compound selected from the group consisting of a l-hydroxy-4-amino-5,8-dihydronaphthalene, a 1,4-diamino-5,8-dihydronaphthalene, a 1-hydroxy-4-amino-5,6,7,8-tetrahydronaphthalene, and a 1,4 diamino 5,6,'7,3 tetrahydronaphthalene.
- an inhibiting compound selected from the group consisting of a l-hydroxy-4-amino-5,8-dihydronaphthalene, a 1,4-diamino-5,8-dihydronaphthalene, a 1-hydroxy-4-amino-5,6,7,8-tetrahydronaphthalene, and a 1,4 diamino 5,6,'7,3 tetrahydronaphthalene.
- Unsaturated gasoline normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of a 1-hydroxy-4-amino-5,8-dihydronaphthalene.
- Unsaturated gasoline normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of a l-hydroxy-4-amino-5,6,'7,B-tetrahydronaphthalene.
- Edible fats and oils normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of a l-hydroxy-4-amino-5,8-dihydronaphthalene.
- Edible fats and oils normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of al-hydroxy-4-amino5,6,7,S-tetrahydronaphthalene.
- Lard containing from about 0.001% to about 0.5% by weight of N-sec-butyl-N-methyl- 1 hydroxy 4 amino 5,6,7,8 tetrahydronaphthalene.
- composition as defined in claim 1 further characterized in that said organic material comprises unsaturated gasoline.
- a composition as defined in claim 13 further characterized in that said organic material comprises a fatty substance.
- composition as defined in claim 1 further characterized in that said organic material comprises lard.
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Description
Patented Mar. 31, 1953 STABILIZATION OF ORGANIC COMPOUNDS Ralph E. Thompson, Hinsdale, 111., assignor to Universal Oil Products Company, Chicago, 111., a corporation of Delaware No Drawing. Application September 16, 1950, Serial No. 185,336
14 Claims. 1
This application is a continuation-in-part of my copending application Serial No. 5,209, filed January 29, 1948, now abandoned, and relates to the stabilization of organic compounds which tend to deteriorate in storage or in use due to oxidation reactions.
Various organic compounds are unstable in storage or during treatment and form undesirable gums, undergo discoloration, form sludges or otherwise deteriorate due to oxidation, polymerization or other undesired reactions. Included among the organic compounds which undergo such deterioration are gasoline, diesel oil, mineral oil, lubricating oil, fuel oil, drying oil, greases, edible fats and oils, acetylenes and particularly vinyl acetylene, butadiene, isoprene, styrene and other vinyl aromatics, various unsaturated alcohols, acids, ketones, etc.
The invention is particularly applicable to the stabilization of unsaturated gasolines and still more particularly cracked and polymer gasolines. In storage or during treatment these unsaturated gasolines tend to form undesirable gums. The invention is also applicable to the treatment of aviation gasolines which tend to undergo deterioration due to the addition of tetraethyl lead fluid or due to other components in the gasoline.
The invention is also particularly applicable to the stabilization of edible fats and oils which generally are of animal or vegetable origin and which tend to become rancid, especially during long periods of storage prior to use. Typical representatives of these edible fats and oils include linseed oil, menhaden oil, cod liver oil, castor oil, olive oil, rapeseed oil, coconut oil, palm oil, corn oil, sesame oil, peanut oil, babassu oil, butter, fat, lard, beef tallow, etc. It is understood that other oils and fats may be treated within the scope of the present invention, including oils and fats which have previously been subjected to various treatments, such as blowing with air heat treatment, etc.
In another embodiment the present invention is particularly applicable to the treatment of crops by dusting or spraying in order to preserve food accessory factors such as carotene, vitamins, various fatty acids, alcohols, etc.
In one embodiment the present invention'relates to an organic material subject to oxidative deterioration containing an inhibitor prepared by reacting an aliphatic amine with a member of the group consisting of 1,4-dihydroxy-5,8-dihydronaphthalene and 1,4-dihydroxy-5,6,7,8-tetrahydronaphthalene.
In a specific embodiment the present invention relates to motor fuel normally tending to deteriorate in storage containing from about 0.001% to about 0.5% by weight of N-sec-butyl-N-methyl-lhydroxy-4-amino-5,6,7,8-tetrahydronaphthalene.
The novel inhibitors of the present invention may be represented by the following general structure:
N/R: R4 OH R4 R R1 R R I II R OH R N\ R R1 R /R1 5 a III IV R, R1, R2, R3, R4, and R5 may comprise hydrogen or alkyl radicals. When these groups comprise alkyl radicals, they preferably are selected so that the total number of carbon atoms in the inhibitor does not exceed about 25 Still more particularly, these compounds preferably comprise alkyl radicals containing from about 1 to about 4 carbon atoms and include such groups as methyl, ethyl, propyl and butyl.
General structure I above illustrates a l-hydroxy 4 amino-5,8-dihydronaphthalene. Pre ferred inhibitors of this class include those in which R. comprises an alkyl group and comprise such compounds as 1-hydroxy-4-methylamino- 5,8 dihydronaphthalene, 1 hydroxy 4 -ethylamino 5,8 dihydronaphthalene, 1 hydroxy- 4 propylamino 5,8 dihydronaphthalene, 1- hydroxy 4 butylamino 5,8 dihydronaphthalene, 1 hydroxy 4 dimethylamino 5,8 dihydronaphthalene, 1 hydroxy 4 diethylamino 5,8 dihydronaphthalene, 1 hydroxy- 4 dipropylamino 5,8 dihydronaphthalene, 1 hydroxy 4 dibutylamino 5,8 -dihydronaphthalene, N ethyl N methyl 1 hydroxy- 4 amino 5,8 dihydronaphthalene, N propyl- N methyl 1 hydroxy 4 amino 5,8 dihydronaphthalene, N butyl N methyl 1- hydroxy 4 amino 5,8 dihydronaphthalene, N propyl N ethyl 1 hydroxy 4 amino- 5,8 dihydronaphthalene, N butyl N ethyl- 1 hydroxy 4 amino 5,8 dihydronaphthalenaetc. ,1
Structure II illustrates a 1,4-diamino-5,8-dihydronaphthalene. Preferred inhibitors in this class include 1,4 diamino 5,8 dihydronaphthalene, 1,4 dimethylamino 5,8 dihydronaphthalene, 1,4 diethylainino 5,8 dihydronaphthalene, 1,4 dipropylamino 5,8 dihydronaphthalene, 1,4 dibutylamino 5,8 dihydro naphthalene, 1 methyl amino 4 ethylamino 5,8 dihydronaphthalene, 1 methylamino 4 propylamino 5,8 '--dihydronaphthalene, 1 methylamino 4 butylamino 5,8,- dihydronaphthalene, 1-ethylamino 4* propylamino 5,8 dihydronaphthalene, 1 ethylamino 4 1-- butylamino.-. 5,8 =dihydronaphthalene,- 1 propylamino: 4 -Ibuty1amino 5,8 dihydronaphthalene, etc; .thercase of the di (alkylamino) compounds it is .desirable that at least one of thealkyl groups is a-sec-alkyl group such as isopropyl orsec-butyla We 1 1 Structure III illustrates a l-hydroxy-4-amino- 5,6,7,8 tetrahydronaphthalene. Preferred inhibitors ofthis class include l-hydroxy-l-methylamino-5,6,7} e tetrahydronapthalene, 1 hydroxy-4 ethylamino-5,6,'7,8 tetrahydronaphthalene, 1-hydroxy-4-propylamino-5}6,7,8-tetrahydronaphthalene, .ij1-hydroxy-4-butylamino-5,6,- 7,8 tetrahydronaphthalene; 1'--- hydroxy4-dimethylamino-5,6;7,8-- tetrahydronaphthalene, 1- hydroxy-l-diethylamino 5,6,'7-,8 tetrahydronaphthalene, 1-hydroxy-4-dipropylamino-5,6,7,8 tetrahydronaphthalene, 1-hydroXy'-.4 dibutylamino-5,6,7,8-tetrahydronaphthalene, N- ether- N methyl-1-hydroxy-4-amino-5,6,7 ,8 tetrahydronaphthalene, N-propyl-N-methyl-l-hydroXy-, l -amino-5,6,'7-,8-tetrahydronaphthalene, N-butyl- N-methyl-l-hydroxy-4-amino-5,6,7,8etetrahydro naphthalene, N-propyl-N-ethyl -.1 hydroXy-4- amino-5,6,'7,8 --tetrahydronaphthalene, N-butyl- N-ethyl-l-hydroxy-'- 4,5,6,7,8w tetrahydronaphthalene, etc.
StructureIV illustrates a l,4-diamino-5,6,7,8- tetrahydronaphthalene. Preferred. inhibitors of this class include 1,4-1diamino-5,6;7,8-tetrahydronaphthalene, 1,4-dimethylamino 5,6,'7,8 tetrahydronaphthalene; "1,4 1- diethylamino 5,637,8- tetrahydronaphthalene, 1,4-dipropylamino-5;6,7- S-tetrahydrpnaphthalene,. 1,4'-'dibuty1amino- 5,6- 7,8 tetrahydron'aphthalene, 1 methylamino-4- ethylamino 5,6,7',8" tetrahydronaphthalene, '1- methylamino-4-propylamino-5;6;7;8 tetrahydronaphthalene; 1- methylamino-4-butylamino 5,6 7,8 +1 tetrahydronaphthalene; "1 ethylamino-4- propylamino 5,'6,7,'8 .-i-tetrahydronaphthalene, 1" ethylamino 4- 'butylamino= '5-,6,7,8-tetrahydronaphthalene, 1 -"propylamino I 4 L butylamino-5,637,8 tetrahydronaphthalene; etc.
It is understood that the 'compoundshereinbefore set forth comprise preferred"inhibitors and that compounds ofthese general structures otherwise substituted by suitable 'groups'are also included within 'the scope'qf; the present invention. For example,- other satisfactory and-in fact in many cases preferred inhibitors include those in which one or both 0;) ,tliehydrogenatoms attached to each nitrogen atoinare replaced by alkyl groups. Specificexam'ples of compounds of 'this class are specified in the list of preferred compounds of'th'e classillu'strated general Structures I and III. Similar di-substituted compounds of the diamino compounds illustrated by general Structures II and IV are comprised within the scope of the present invention. However, as hereinbefore set forth, it is preferred that the total number of carbon atoms in the inhibitors does not exceed about 25. r
- -Itis understood that'the inhibitors of the present invention may comprise the specific compounds named herein in admixture with various isomers thereof. For example, in the dihydrocompound the isom'ers may comprise corresponding compounds in which the double bond in the non-aromaticringhas shifted to a conjugated position and/or those in which the hydroxy and amino groupshave interchanged positions with respect to'an' a'lkyl group positioned on the nonaro'rnatic ring. In the tetrahydro compounds, the isomers will be of the latter type.
' Th'e'inhibitors of the present invention may be prepared in any suitable manner. In general, these'inhibitorsare prepared by the reaction of a 1,4 dihydroxy 5,ii-dihydronaphthalene or IA-dihydroXy- 5,-6;;7 -tetrahydronaphthalene with a suitablealiphatic amine'; "Suitable aliphatic amines include methyl amine; ethyl amine, propyl amine, isopropyl amine, -n-butyl amine, isobutyl amine, -sec-bu'tylamine, etc; {The reaction is generally effected b'yheat-ing the reactants at an elevated temperature andrecoverin'g'the products by extraction in suitable solvents; As a typical "example; a specific method'of preparationis hereinafterset-forth. In one m'ethod ofprparing lhydroxy-4-sec butylamino 5,8 dihydronaphthaleneand L4- di-sec-but'ylamino" -=5;a" dillydrohaphtlialene,
1 ,4-dihydr6Xy- 5,8 diliydronaph'thalne maybe heatedin-asealed tubewitHsec-butyl in'e-at an elevated temperature of about-2005C. When the diall'zylaminobb'inpdiind is ifis'iredth'e amount of secuty1amine and tne reaeuon time are in creased'in-- order 'to efit reaction of the amine Withbo'l'il'i'of the hydi 'ify groups;- After 't-he reaction has proceeded tb -th desired extent, the product-ma be" dissolvd in an organic solvent, such as ethe -pet rq1eumetner; and then extracted vvith a dilut'eadueoiis sodium hydroxide solution to remov th iinracted 'startihg material. Th''pibdut su sequent y extracted with Claisen solution to' reinoi th li-hydroxyA-secbutyl-5;8 dihydronapfithalne' and to thereby separate it ream 1,4 di sec -butylamino-5,S dihydronaph'thalene. The other alkylaznino substituted' compounds may be' 'pr'epared ina'simil'ar mannenby varying the starting reagents as desired; Similarly the tetrahydro-substituted compounds are made in substantially the same man-- her by "starting with 1,4 di-hydroxy-5,6,'Z,8-tetraliydronaphtha'lehel r F Whenit is desired to produce compounds contain'i'ng two*alkyl-groups"attached" to-the' same pound may be treatedwith a suitablealkylation agent such" as dim'ethyl 'suliata' diethyl 1 sulfate, propyl chloride, etci in order'toproduce the dethe inhibitor may be used in conjunction with a synergist, such as phosphoric acid, ascorbic acid, citric acid, etc.
The following examples are introduced to further illustrate the novelty and utility of the present invention but not with the intention of unduly limiting the same.
EXAMPLE I The inhibitors used in the following runs were prepared in a manner similar to that heretofore set forth. These inhibitors were tested in a Pennsylvania cracked gasoline which had an induction period of 100 minutes. The inhibitor was added in a concentration of 0.01% by Weight to different samples of the gasoline and gave the results as shown in Table I.
lene l,4-di-sec-butylan1ino5,6,7,8-tetrahydronaphthalene... N-scc-butyl-N-methyl-l-hydroxy-4-amino-5,0,7,8-tetra- 1 hydronaph thalene It will be noted that inhibitors of the present invention increased the induction period from 100 minutes to at least 285 minutes and that the last mentioned compound, which comprised a tertiary amine, increased the induction period to 650 minutes. The inhibitor of the present invention therefore preferably contains a tertiary amine grouping.
EXAMPLE II The inhibitors used in the following run were prepared in a manner similar to that heretofore set forth. These inhibitors were added to lard which had a normal stability period of 9 hours as determined by the Swift test. This test is described in detail in the article by A. E. King, H. L. Roschen and W. H. Irwin, which appeared in the Oil and Soap, vol. X, No. 6, pages 105 to 109 (1933). In general, this test comprises bubbling air through a sample of the lard and reporting the number of hours until the lard develops a peroxide value of 20. 0.02% by weight of the inhibitors were added to this sample of the lard and gave the results as shown in Table II.
Table II Stability Inhibitor Period,
Hours 1-hydroxy-4-sec-butylamino-5,S-dihydronaphthalene 111 N-sec-butyl-N-methyl-l-hydroxy-4'amino-5,6,7,8-tetrahydrcnaphthalene 111 It will be noted that the inhibitors of the present invention increased the stability period of the lard from 9 hours to greater than 111 hours.
I claim as my invention:
1. An organic material normally subject to oxidative deterioration containing, as an inhibitor for said deterioration, a small amount of. an inhibiting compound selected from the group consisting of a l-hydroxy-4-amino-5,8-dihydronaphthalene, a 1,4-diamino-5,8-dihydronaphthalene, a 1-hydroxy-4-amino-5,6,7,8-tetrahydronaphthalene, and a 1,4 diamino 5,6,'7,3 tetrahydronaphthalene.
2. Unsaturated gasoline normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of a 1-hydroxy-4-amino-5,8-dihydronaphthalene.
3. Unsaturated gasoline normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of a l-hydroxy-4-amino-5,6,'7,B-tetrahydronaphthalene.
4. Unsaturated gasoline containing a small amount of a l-hydroxyi-alkylamino-5,8-dihydronaphthalene.
5. Unsaturated gasoline containing a small amount of a l-hydroxy-4-alkylamino-5,6,7,8- tetrahydronaphthalene.
6. Cracked gasoline containing from about 0.001% to about 0.5% by weight or N-sec-butyl N methyl 1 hydroxy 4 amino 5,8 dihydronaphthalene.
'7. Cracked gasoline containing from about 0.001% to about 0.5% by weight of N-sec-butyl- N methyl 1 hydroxy 4 amino 5,6,'7,8 tetrahydronaphthalene.
8. Edible fats and oils normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of a l-hydroxy-4-amino-5,8-dihydronaphthalene.
9. Edible fats and oils normally tending to deteriorate in storage containing, as an inhibitor for said deterioration, a small amount of al-hydroxy-4-amino5,6,7,S-tetrahydronaphthalene.
10. Lard containing from about 0.001% to about 0.5% by Weight of N-sec-butyl-N-methyl- 1-hydroxy-4-amino-5,8-dihydronaphthalene.
11. Lard containing from about 0.001% to about 0.5% by weight of N-sec-butyl-N-methyl- 1 hydroxy 4 amino 5,6,7,8 tetrahydronaphthalene.
12. A composition as defined in claim 1 further characterized in that said organic material comprises unsaturated gasoline.
13. A composition as defined in claim 1 further characterized in that said organic material comprises a fatty substance.
14. A composition as defined in claim 1 further characterized in that said organic material comprises lard.
RALPH B. THOMPSON.
REFERENCES CITED UNITED STATES PATENTS Name Date Missbach Sept. 28, 1937 Number
Claims (1)
1. AN ORGANIC MATERIAL NORMALLY SUBJECT TO OXIDATIVE DETERIORATION CONTAINING, AS AN INHIBITOR FOR SAID DETERIORATION, A SMALL AMOUNT OF AN INHIBITING COMPOUND SELECTED FROM THE GROUP CONSISTING OF A 1-HYDROXY-4-AMINO-5,8-DIHYDRONAPHNAPHTHALENE, A 1,4-DIAMINO-5,8-DIHYDRONAPHTHALENE, A 1-HYDROXY-4-AMINO-5,6,7,8-TETRAHYDRONAPHTHALENE, AND A 1,4 - DIAMINO - 5,6,7,8 TETRAHYDRONAPHTHALENE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| US185336A US2633425A (en) | 1950-09-16 | 1950-09-16 | Stabilization of organic compounds |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US185336A US2633425A (en) | 1950-09-16 | 1950-09-16 | Stabilization of organic compounds |
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| US185336A Expired - Lifetime US2633425A (en) | 1950-09-16 | 1950-09-16 | Stabilization of organic compounds |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2771367A (en) * | 1953-11-20 | 1956-11-20 | Universal Oil Prod Co | Stabilization of organic compounds |
| US2811429A (en) * | 1953-08-31 | 1957-10-29 | Eastman Kodak Co | Stabilization of motor fuels |
| US2865723A (en) * | 1953-08-31 | 1958-12-23 | Eastman Kodak Co | Stabilized motor fuels |
| US2977308A (en) * | 1952-04-23 | 1961-03-28 | Bayer Ag | Tetrahydronaphthylamino compounds |
| US3051591A (en) * | 1958-07-23 | 1962-08-28 | Miehle Goss Dexter Inc | Quick drying vehicle and method |
| US3240609A (en) * | 1961-12-13 | 1966-03-15 | Miles Lab | Hydroxy naphthylmethylamino bis propionic acid derivatives as antioxidants for edible fats and oils |
| US4320021A (en) * | 1975-10-14 | 1982-03-16 | The Lubrizol Corporation | Amino phenols useful as additives for fuels and lubricants |
| US4425138A (en) | 1975-10-14 | 1984-01-10 | The Lubrizol Corporation | Two-cycle fuel compositions containing amino phenols |
| US4773916A (en) * | 1985-12-05 | 1988-09-27 | Union Oil Company Of California | Fuel composition and method for control of octane requirement increase |
| US4986996A (en) * | 1988-07-08 | 1991-01-22 | University Of St. Andrews | Ethoxyquin derivatives as antioxidants in edible oils and fish meal |
| US20040045884A1 (en) * | 2002-09-11 | 2004-03-11 | Roth Robert A. | Heated fuel strainer assembly |
| US20040129626A1 (en) * | 2003-01-06 | 2004-07-08 | Fischer John G. | Fuel strainer assembly |
| US20040140257A1 (en) * | 2003-01-21 | 2004-07-22 | Dockery Randall L. | Fuel strainer assembly |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2094367A (en) * | 1933-10-09 | 1937-09-28 | Stauffer Chemical Co | Stabilized carbon tetrachloride |
-
1950
- 1950-09-16 US US185336A patent/US2633425A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2094367A (en) * | 1933-10-09 | 1937-09-28 | Stauffer Chemical Co | Stabilized carbon tetrachloride |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2977308A (en) * | 1952-04-23 | 1961-03-28 | Bayer Ag | Tetrahydronaphthylamino compounds |
| US2811429A (en) * | 1953-08-31 | 1957-10-29 | Eastman Kodak Co | Stabilization of motor fuels |
| US2865723A (en) * | 1953-08-31 | 1958-12-23 | Eastman Kodak Co | Stabilized motor fuels |
| US2771367A (en) * | 1953-11-20 | 1956-11-20 | Universal Oil Prod Co | Stabilization of organic compounds |
| US3051591A (en) * | 1958-07-23 | 1962-08-28 | Miehle Goss Dexter Inc | Quick drying vehicle and method |
| US3240609A (en) * | 1961-12-13 | 1966-03-15 | Miles Lab | Hydroxy naphthylmethylamino bis propionic acid derivatives as antioxidants for edible fats and oils |
| US4320021A (en) * | 1975-10-14 | 1982-03-16 | The Lubrizol Corporation | Amino phenols useful as additives for fuels and lubricants |
| US4425138A (en) | 1975-10-14 | 1984-01-10 | The Lubrizol Corporation | Two-cycle fuel compositions containing amino phenols |
| US4773916A (en) * | 1985-12-05 | 1988-09-27 | Union Oil Company Of California | Fuel composition and method for control of octane requirement increase |
| US4986996A (en) * | 1988-07-08 | 1991-01-22 | University Of St. Andrews | Ethoxyquin derivatives as antioxidants in edible oils and fish meal |
| US20040045884A1 (en) * | 2002-09-11 | 2004-03-11 | Roth Robert A. | Heated fuel strainer assembly |
| US6743355B2 (en) | 2002-09-11 | 2004-06-01 | Delphi Technologies, Inc. | Heated fuel strainer assembly |
| US20040129626A1 (en) * | 2003-01-06 | 2004-07-08 | Fischer John G. | Fuel strainer assembly |
| US6833070B2 (en) | 2003-01-06 | 2004-12-21 | Delphi Technologies, Inc. | Fuel strainer assembly |
| US20050098489A1 (en) * | 2003-01-06 | 2005-05-12 | Delphi Technologies, Inc. | Fuel strainer assembly |
| US6998043B2 (en) | 2003-01-06 | 2006-02-14 | Delphi Technologies, Inc. | Fuel strainer assembly |
| US20040140257A1 (en) * | 2003-01-21 | 2004-07-22 | Dockery Randall L. | Fuel strainer assembly |
| US6830687B2 (en) | 2003-01-21 | 2004-12-14 | Delphi Technologies, Inc. | Fuel strainer assembly |
| US20050115887A1 (en) * | 2003-01-21 | 2005-06-02 | Delphi Technologies, Inc | Fuel strainer assembly |
| US6936168B2 (en) | 2003-01-21 | 2005-08-30 | Delphi Technologies, Inc. | Fuel strainer assembly |
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