US2063575A - Dispersing of phenolphthalein in mineral lubricating oils - Google Patents
Dispersing of phenolphthalein in mineral lubricating oils Download PDFInfo
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- US2063575A US2063575A US718529A US71852934A US2063575A US 2063575 A US2063575 A US 2063575A US 718529 A US718529 A US 718529A US 71852934 A US71852934 A US 71852934A US 2063575 A US2063575 A US 2063575A
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- Prior art keywords
- phenolphthalein
- oil
- dispersing
- alcohol
- mineral
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 title description 59
- 239000010688 mineral lubricating oil Substances 0.000 title description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 239000002480 mineral oil Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 238000007664 blowing Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 239000002195 soluble material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- KSCQDDRPFHTIRL-UHFFFAOYSA-N auramine O Chemical compound [H+].[Cl-].C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 KSCQDDRPFHTIRL-UHFFFAOYSA-N 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-M sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-M 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
Classifications
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- 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
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/007—Coloured or dyes-containing lubricant compositions
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- 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
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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- 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
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- 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
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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- 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
- C10M2207/28—Esters
- C10M2207/284—Esters of aromatic monocarboxylic acids
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- 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
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
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- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/044—Acids; Salts or esters thereof
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- 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
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- 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
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- 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
- C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- 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
- C10M2215/30—Heterocyclic compounds
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- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/21—Hydrocarbon
Definitions
- My invention relates to the dispersion of preferentially alcohol soluble materials in mineral oils.' More particularly it relates to the dispersion of preferentially alcohol soluble materials- 10 particularly lubricating oils, by the use of alcohols having molecular weights greater than that of the propanols. My invention also relates to the products resulting from mynew method of dispersion.
- an alcohol preferably a mono-hydroxy alcohol, having a molecular weight greater than that of the propanols, for instance: the butanols, the pentanols, the hexanols, the heptanols or mixtures of any of 55 these with each other and/or with up to about 50% of methanol and/or ethanol.
- the amount of phenolphthalein and the amount of alcohol can be varied within wide limits, thus, for instance, from 0.05 ounce to one pound or even more of phenolphthalein and from five ounces to gallons or even more of alcohol having a molecular weight greater than that of the propanols, preferably normal butanol, can be used per 10,000 gallons of oil.
- This method can be used in dispersing phenolphthalein in other mineral -oils,-for instance: gasoline, kerosene, furnace oil, fuel oil, etc.
- Other preferentially water or alcohol soluble indicators or dye -intermediates can thus be distributed, for instance: phenylenediamine, methyl orange (the sodium salt of helianthine), bromophenol blue (tetrabromophenolsulfonphthalein),
- the same method can be utilized forintro ducing preferentially water or alcohol soluble dyestuffs in mineral oils, for instance: spirit dyes, such as alizarine (dihydroxy anthroquanone (1,2), eosine '(tetrabromofiuoresceinl and its alkaline salts, fluorescein (resorcinphthalein) auramin, malachite green (tetramethyldi-.paminotriphenyl carbohydride' hydrochloride) cyanine, etc. Still other preferentially water or alcohol soluble materials such as antioxidants, antiknock improvers, etc. can thus be introduced.
- spirit dyes such as alizarine (dihydroxy anthroquanone (1,2), eosine '(tetrabromofiuoresceinl and its alkaline salts, fluorescein (resorcinphthalein) auramin, malachite green (tetramethyldi-.paminotripheny
- the amount ofpreferentially alcohol soluble material tobe added will, of course, vary greatly with the potency of the particular material chosen, the result to be accomplished, etc. In genera] the amount will range from, say, 0.01 ounce to five pounds, or preferably .05 ounce to one pound, per 10,000 gallons of mineral oil.
- the amount of higher alcohol necessary to disperse this material in accordance with my invention will also vary greatly but, in general, may range from one ounce to 25 gallons, or preferably from five ounces to one gallon per.10,000 gallons of mineral oil.
- a method of dispersing phenolphthalein in mineral lubricating oil comprising dissolving ap proximately 0.25 ounce of phenolphthalein in approximately one pint of normal butanol, introducing the solution thus formed into approx mately 10,000 gallons of mineral lubricating oil and distributing the said solution throughout the said oil by blowing with air.
- Fluid oils comprising the following materials in approximately the following proportions: mineral oil, 10,000 gallons; preferentially alcohol soluble material selected from the group consisting of the dyestuffs, the dye intermediates, the indicators, the antioxidants and the antiknock improvers, from 0.01 ounce to five pounds; a monohydroxy alcohol having a molecular weight greator than that of propanol, from one ounce to 25 gallons.
- Fluid oils comprising the following materials in approximately the following proportions: mineral lubricating oil, 10,000 gallons; phenolphthalein, 0.25 ounce; normal butanol, one pint.
- a fluid oil composition comprising a solution of mineral lubricating oil, phenolphthalein and normal butyl alcohol.
- a fluid oil composition comprising a solution of mineral lubricating oil, phenolphthalein and a normally liquid aliphatic alcohol having a molecular weight greater than that of the propanols.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Dec. 8, 1936 UNITED STATES DISPERSING OF PHENOLPHTHALEIN IN IVIINERAL LUBRIQATING OILS Elmer Wade Adams, Hammond, Ind., assignor to Standard Oil Company, Chicago, 111., a corporation of Indiana No Drawing. Application March 31, 1934,
Serial No. 718,529
. 8 Claims. My invention relates to the dispersion of preferentially alcohol soluble materials in mineral oils.' More particularly it relates to the dispersion of preferentially alcohol soluble materials- 10 particularly lubricating oils, by the use of alcohols having molecular weights greater than that of the propanols. My invention also relates to the products resulting from mynew method of dispersion.
It has been proposed to provide a means for the identification of mineral oils by incorporating therein asmall portion of an indicator or other relatively colorless material which will form a detectable color on treatment with a'suit- 20 able chemical reagent. Thus, for instance, it
has been proposed to provide a means for identifying lubricating oils by incorporating therein a trace of phenolphthalein (dihydroxyphthalophenone) which will form a brilliant red colora- 25 tion when the oil is-shaken with an aqueous alkaline solution. The idea is simple but it' has not been satisfactorily accomplished in the past due to the difliculty of incorporating the phenolphthalein in the oil. Phenolphthalein, being 80 preferentially soluble in water and the alcohols rather than in mineral oils, cannot readily be incorporated directly in the oil. Neither can it be incorporated satisfactorily in solution in such a material as ethanol. Thus, for example, when 0.25 ounce of phenolphthalein is dissolved in one pint of ethanol, the solution is added to 10,000
gallons of lubricating oil, and the phenolphthalein is distributed in the oil by the normal air blowing method, it .is found that the phenolphthalein concentration in the oil diminishes gradually, due to preciptation, thereby destroying its quantitative value in detecting adulteration. Furthermore, when the solution of phenol- 45 phthalein in oil is filtered, for instance through ordinary filter paper, the phenolphthalein is completely removed. V
I have overcome these difficulties by first dissolving the phenolphthalein in an alcohol, preferably a mono-hydroxy alcohol, having a molecular weight greater than that of the propanols, for instance: the butanols, the pentanols, the hexanols, the heptanols or mixtures of any of 55 these with each other and/or with up to about 50% of methanol and/or ethanol. I prefer, however, to use normal butanol.
Thus, for instance, when 0.25 ounce of phenolphthalein is dissolved in one pint of normal butanol and the solution thus formed is added to 10,000 gallons of lubricating oil it can be distributed uniformly throughout the oil by agitating by the normal air blowing method without precipitation of the phenolphthalein. Furthermore, when the oil solution thus formed by the use of normal butanol is filtered, for instance through ordinary filter paper, the phenolphthalein is not removed as was the case when it was added in ethanol solution. I am not aware just what the reason is for the peculiar action of this relatively minute amount of higher alcohol, but I believe it may be attributed, to the formation of a loose chemical compound or alcoholate between the phenolphthalein and the higher alcohol.
The amount of phenolphthalein and the amount of alcohol can be varied within wide limits, thus, for instance, from 0.05 ounce to one pound or even more of phenolphthalein and from five ounces to gallons or even more of alcohol having a molecular weight greater than that of the propanols, preferably normal butanol, can be used per 10,000 gallons of oil. The
upper limits of both the phenolphthalein and the .7 I
alcohol are determined by economic factors.
This method can be used in dispersing phenolphthalein in other mineral -oils,--for instance: gasoline, kerosene, furnace oil, fuel oil, etc. Other preferentially water or alcohol soluble indicators or dye -intermediates can thus be distributed, for instance: phenylenediamine, methyl orange (the sodium salt of helianthine), bromophenol blue (tetrabromophenolsulfonphthalein),
etc.
The same method can be utilized forintro ducing preferentially water or alcohol soluble dyestuffs in mineral oils, for instance: spirit dyes, such as alizarine (dihydroxy anthroquanone (1,2), eosine '(tetrabromofiuoresceinl and its alkaline salts, fluorescein (resorcinphthalein) auramin, malachite green (tetramethyldi-.paminotriphenyl carbohydride' hydrochloride) cyanine, etc. Still other preferentially water or alcohol soluble materials such as antioxidants, antiknock improvers, etc. can thus be introduced.
The amount ofpreferentially alcohol soluble material tobe added will, of course, vary greatly with the potency of the particular material chosen, the result to be accomplished, etc. In genera] the amount will range from, say, 0.01 ounce to five pounds, or preferably .05 ounce to one pound, per 10,000 gallons of mineral oil. The amount of higher alcohol necessary to disperse this material in accordance with my invention will also vary greatly but, in general, may range from one ounce to 25 gallons, or preferably from five ounces to one gallon per.10,000 gallons of mineral oil.
While I have described my invention in connection with certain specific embodiments and in connection with certain theories of operation it is to be understood that these are by way of illustration rather than by way of limitation and I do not intend to be limited thereby except to the scope of the appended claims.
I claim: I
1. A method of dispersing phenolphthalein in mineral lubricating oil, comprising dissolving ap proximately 0.25 ounce of phenolphthalein in approximately one pint of normal butanol, introducing the solution thus formed into approx mately 10,000 gallons of mineral lubricating oil and distributing the said solution throughout the said oil by blowing with air.
2. Fluid oils, comprising the following materials in approximately the following proportions: mineral oil, 10,000 gallons; preferentially alcohol soluble material selected from the group consisting of the dyestuffs, the dye intermediates, the indicators, the antioxidants and the antiknock improvers, from 0.01 ounce to five pounds; a monohydroxy alcohol having a molecular weight greator than that of propanol, from one ounce to 25 gallons.
3. Fluid oils, comprising the following materials in approximately the following proportions: mineral lubricating oil, 10,000 gallons; phenolphthalein, 0.25 ounce; normal butanol, one pint.
4. The method of dispersing phenolphthalein in mineral lubricating oils comprising dissolving said phenolphthalein in normal butyl alcohol and introducing the solution thus formed into the mineral oil.
5. A fluid oil composition comprising a solution of mineral lubricating oil, phenolphthalein and normal butyl alcohol.
6. The method of dispersing phenolphthalein in a mineral lubricating oil comprising dissolving said phenolphthalein in a normally liquid aliphatic alcohol having a molecular weight greater than that of the propanols and introducing the solution thus formed into the mineral oil.
7. The method of dispersing phenolphthalein in mineral lubricating oils comprising dissolving sail phenolphthalein in a normally liquid aliphatic alcohol having a molecular weight greater than that of the propanols, introducing the solution thus formed into the mineral oil, and agitating the admixture by blowing with air.
- 8. A fluid oil composition comprising a solution of mineral lubricating oil, phenolphthalein and a normally liquid aliphatic alcohol having a molecular weight greater than that of the propanols.
ELMER WADE ADAMS.
CERTIFICATE OF CORRECTION.
atent No. 2,065,575. December 8, 1936.
ELMER WADE ADAMS.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, strike out all of claim 2 and for the claim numbers "3" "4" 5" "6", "'7" and "8" read 2, 3, 4, 5, 6, and 7 respectively; and that the said Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 16th day of February, A. D. 1937.
Henry Van Arsdale Seal) Acting Commissioner of Patents.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US718529A US2063575A (en) | 1934-03-31 | 1934-03-31 | Dispersing of phenolphthalein in mineral lubricating oils |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US718529A US2063575A (en) | 1934-03-31 | 1934-03-31 | Dispersing of phenolphthalein in mineral lubricating oils |
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US2063575A true US2063575A (en) | 1936-12-08 |
Family
ID=24886411
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Application Number | Title | Priority Date | Filing Date |
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US718529A Expired - Lifetime US2063575A (en) | 1934-03-31 | 1934-03-31 | Dispersing of phenolphthalein in mineral lubricating oils |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2451022A (en) * | 1944-02-28 | 1948-10-12 | Frederick C Dohrmann | Color changing antiseptic composition |
FR2501044A1 (en) * | 1981-03-04 | 1982-09-10 | Machugh John | 3,3-BIS- (β-HYDROXYPHENYL) -PHTALID MEDICINAL PRODUCT AND PROCESS FOR PREPARING THE SAME |
EP0311790A1 (en) * | 1987-09-18 | 1989-04-19 | BASF Aktiengesellschaft | Marked mineral oil product, and process to mark mineral oil products |
WO1996000272A1 (en) * | 1994-06-27 | 1996-01-04 | Basf Aktiengesellschaft | Use of leucotriarylmethanes for marking hydrocarbons |
WO1996022345A1 (en) * | 1995-01-20 | 1996-07-25 | United Color Manufacturing, Inc. | Fluorescent petroleum markers |
WO1996032461A1 (en) * | 1995-04-13 | 1996-10-17 | United Color Manufacturing, Inc. | Developer system for base reactable petroleum fuel markers |
WO1996032462A1 (en) * | 1995-04-13 | 1996-10-17 | United Color Manufacturing, Inc. | Colorless petroleum markers |
US6482651B1 (en) | 1999-06-30 | 2002-11-19 | United Color Manufacturing, Inc. | Aromatic esters for marking or tagging petroleum products |
-
1934
- 1934-03-31 US US718529A patent/US2063575A/en not_active Expired - Lifetime
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2451022A (en) * | 1944-02-28 | 1948-10-12 | Frederick C Dohrmann | Color changing antiseptic composition |
FR2501044A1 (en) * | 1981-03-04 | 1982-09-10 | Machugh John | 3,3-BIS- (β-HYDROXYPHENYL) -PHTALID MEDICINAL PRODUCT AND PROCESS FOR PREPARING THE SAME |
EP0073758A1 (en) * | 1981-03-04 | 1983-03-16 | John Edward Mchugh | Treatment of inflammatory viral infections, acne, dermatitis and arthritis conditions. |
EP0073758A4 (en) * | 1981-03-04 | 1983-07-04 | John Edward Mchugh | Treatment of inflammatory viral infections, acne, dermatitis and arthritis conditions. |
EP0311790A1 (en) * | 1987-09-18 | 1989-04-19 | BASF Aktiengesellschaft | Marked mineral oil product, and process to mark mineral oil products |
WO1996000272A1 (en) * | 1994-06-27 | 1996-01-04 | Basf Aktiengesellschaft | Use of leucotriarylmethanes for marking hydrocarbons |
WO1996022345A1 (en) * | 1995-01-20 | 1996-07-25 | United Color Manufacturing, Inc. | Fluorescent petroleum markers |
CN1086729C (en) * | 1995-01-20 | 2002-06-26 | 联合颜料制造公司 | Fluorescent petroleum markers |
WO1996032461A1 (en) * | 1995-04-13 | 1996-10-17 | United Color Manufacturing, Inc. | Developer system for base reactable petroleum fuel markers |
WO1996032462A1 (en) * | 1995-04-13 | 1996-10-17 | United Color Manufacturing, Inc. | Colorless petroleum markers |
US5672182A (en) * | 1995-04-13 | 1997-09-30 | United Color Manufacturing Inc. | Developer system for base reactable petroleum fuel markers |
CN1088743C (en) * | 1995-04-13 | 2002-08-07 | 联合色料制造公司 | Colorless petroleum markers |
US6482651B1 (en) | 1999-06-30 | 2002-11-19 | United Color Manufacturing, Inc. | Aromatic esters for marking or tagging petroleum products |
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