US20020038064A1 - Colorless petroleum marker dyes - Google Patents
Colorless petroleum marker dyes Download PDFInfo
- Publication number
- US20020038064A1 US20020038064A1 US09/954,373 US95437301A US2002038064A1 US 20020038064 A1 US20020038064 A1 US 20020038064A1 US 95437301 A US95437301 A US 95437301A US 2002038064 A1 US2002038064 A1 US 2002038064A1
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- US
- United States
- Prior art keywords
- alkyl
- compound
- hydrogen
- ppm
- composition
- 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.)
- Abandoned
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- 239000003550 marker Substances 0.000 title claims abstract description 13
- 239000000975 dye Substances 0.000 title description 3
- 239000003208 petroleum Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000003209 petroleum derivative Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000003350 kerosene Substances 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- 239000002283 diesel fuel Substances 0.000 claims description 3
- 239000000446 fuel Substances 0.000 claims description 3
- 239000000295 fuel oil Substances 0.000 claims description 3
- 239000003502 gasoline Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 150000003738 xylenes Chemical class 0.000 description 4
- CPBJMKMKNCRKQB-UHFFFAOYSA-N 3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 CPBJMKMKNCRKQB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 0 [1*]C(=O)OC1=C([2*])C=C(C2(C3=C([4*])C([3*])=C(OC([1*])=O)C([2*])=C3)OC(=O)C3=C2C([5*])=C([5*])C([5*])=C3[5*])C([4*])=C1[3*] Chemical compound [1*]C(=O)OC1=C([2*])C=C(C2(C3=C([4*])C([3*])=C(OC([1*])=O)C([2*])=C3)OC(=O)C3=C2C([5*])=C([5*])C([5*])=C3[5*])C([4*])=C1[3*] 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- SCIJGBBERLVKGV-UHFFFAOYSA-N C.CCCC(=O)OC1=C(C)C=C(C2(C3=CC(C)=C(OC(=O)CCC)C=C3)OC(=O)C3=C2C=CC=C3)C=C1 Chemical compound C.CCCC(=O)OC1=C(C)C=C(C2(C3=CC(C)=C(OC(=O)CCC)C=C3)OC(=O)C3=C2C=CC=C3)C=C1 SCIJGBBERLVKGV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LDKDGDIWEUUXSH-UHFFFAOYSA-N Thymophthalein Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C LDKDGDIWEUUXSH-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
- C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
-
- 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
- C10L1/202—Organic compounds containing halogen aromatic bond
-
- 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
- C10L1/205—Organic compounds containing halogen carboxylic radical containing compounds or derivatives, e.g. salts, esters
Definitions
- This invention relates generally to a composition comprising a colorless marker dye and a liquid petroleum product, and to a method for marking petroleum products.
- phthalein derivatives are known and used as markers in petroleum applications and other industrial applications such as paints and plastics.
- U.S. Pat. No. 6,002,056 describes the use of thymolphthalein, cresolphthalein and related compounds as markers for petroleum products.
- this reference discloses only compounds having two phenolic hydroxyl groups, and does not suggest the use of phthalein esters as markers.
- phthalein derivatives stem from their typically low solubility in petroleum products.
- phthalein markers can be removed from a marked petroleum product by extraction with water, either deliberately by one seeking to circumvent the marking, or as a result of contact of the marked petroleum product with water bottoms in storage tanks.
- alkyl is a hydrocarbyl group having from one to eighteen carbon atoms in a linear, branched or cyclic arrangement. Substitution on alkyl groups of one or more halo, alkoxy, alkanoyl or amido groups is permitted; alkoxy, alkanoyl and amido groups may in turn be substituted by one or more halo substituents. Preferably, alkyl groups are unsubstituted.
- alkenyl is an “alkyl” group in which at least one single bond has been replaced with a double bond.
- An “aryl” group is a substituent derived from an aromatic compound, including heterocyclic aromatic compounds having heteroatoms chosen from among nitrogen, oxygen and sulfur.
- the liquid petroleum product is gasoline, diesel fuel, jet fuel, fuel oil, kerosene or lamp oil. It is preferred that the compound of formula I is present in an amount from 0.5 ppm to 100 ppm, and further preferred that it is present in an amount from 0.5 ppm to 10 ppm. It is preferred that the compound of formula I is prepared as a mixture with a high-boiling hydrocarbon-soluble solvent.
- Preferred solvents include 1-octyl-2-pyrrolidone, mixed methylnaphthalenes (sold as AROMATIC 200 by Exxon Corporation) or aromatic hydrocarbon solvents. The preferred concentration of the marker in the solvent is from 20% to 30%.
- the developing reagent is a strongly basic reagent, e.g., a hydroxide of an alkali metal or of a quaternary ammonium ion.
- the reagent is a quaternary ammonium hydroxide.
- This invention is further directed to the compound of formula I in which R 1 is propyl, R 2 is methyl, and R 3 , R 4 , and R 5 are hydrogen. Preparation of this compound is described in Example 1.
- a marker solution was prepared by dissolving a 100 mg portion of the residue in xylenes (100 mL), and diluting 1 mL of the resulting solution to 100 mL with kerosene to make a 10 ppm solution.
- a developer was made by dissolving 1 g of a 40% solution of benzyltrimethylammonium hydroxide in methanol in 99 g of 2-ethyl-1-hexanol. To a 10 mL portion of the 10 ppm marker solution prepared above was added 2.5 mL of the developer. After the mixture was shaken for a few seconds, it acquired a blue-purple color. If necessary, quantitative determination of the marker concentration can be accomplished by measuring the absorbance of the solution at a wavelength of 581 nm.
Abstract
A composition comprising a liquid petroleum product and a colorless marker compound in an amount that is not detectable visually, and a method for marking a liquid petroleum product with a colorless marker compound.
Description
- This invention relates generally to a composition comprising a colorless marker dye and a liquid petroleum product, and to a method for marking petroleum products.
- Certain phthalein derivatives are known and used as markers in petroleum applications and other industrial applications such as paints and plastics. For example, U.S. Pat. No. 6,002,056 describes the use of thymolphthalein, cresolphthalein and related compounds as markers for petroleum products. However, this reference discloses only compounds having two phenolic hydroxyl groups, and does not suggest the use of phthalein esters as markers.
- The disadvantages of phthalein derivatives stem from their typically low solubility in petroleum products. As a result of this characteristic, phthalein markers can be removed from a marked petroleum product by extraction with water, either deliberately by one seeking to circumvent the marking, or as a result of contact of the marked petroleum product with water bottoms in storage tanks.
- The problem addressed by this invention is to find colorless marker dyes with improved solubility in petroleum products.
- The present invention is directed to a composition comprising a liquid petroleum product and a compound of formula I in an amount that is not detectable visually.
- In formula I, R 1 is C1-C18 alkyl, C1-C18 alkenyl, aryl or aralkyl; R2, R3 and R4 are independently hydrogen, C1-C12 alkyl, chloro or bromo; and R5 is hydrogen, chloro or bromo.
- The present invention is further directed to a method of marking a liquid petroluem product comprising adding to the petroleum product as a marker an amount of a compound of formula I that is not detectable visually, and wherein the marker develops a color on contact with a developing reagent.
- An “alkyl” group is a hydrocarbyl group having from one to eighteen carbon atoms in a linear, branched or cyclic arrangement. Substitution on alkyl groups of one or more halo, alkoxy, alkanoyl or amido groups is permitted; alkoxy, alkanoyl and amido groups may in turn be substituted by one or more halo substituents. Preferably, alkyl groups are unsubstituted. An “alkenyl” group is an “alkyl” group in which at least one single bond has been replaced with a double bond. An “aryl” group is a substituent derived from an aromatic compound, including heterocyclic aromatic compounds having heteroatoms chosen from among nitrogen, oxygen and sulfur. An aryl group has a total of from five to twenty ring atoms, and has one or more rings which are separate or fused. Substitution on aryl groups of one or more halo, alkyl, alkenyl, alkoxy, alkanoyl or amido groups is permitted, with substitution by one or more halo groups being possible on alkyl, alkenyl, alkoxy, alkanoyl or amido groups. Preferably, aryl groups are unsubstituted or are substituted only by halo or alkyl groups. An “aralkyl” group is an “alkyl” group substituted by an “aryl” group.
- It is preferred that R 2, R3 and R4 are hydrogen or alkyl having from one to four carbon atoms. It is also preferred that R1 is alkyl having from one to four carbon atoms. It is preferred that R5 is hydrogen.
- It is preferred that the liquid petroleum product is gasoline, diesel fuel, jet fuel, fuel oil, kerosene or lamp oil. It is preferred that the compound of formula I is present in an amount from 0.5 ppm to 100 ppm, and further preferred that it is present in an amount from 0.5 ppm to 10 ppm. It is preferred that the compound of formula I is prepared as a mixture with a high-boiling hydrocarbon-soluble solvent. Preferred solvents include 1-octyl-2-pyrrolidone, mixed methylnaphthalenes (sold as AROMATIC 200 by Exxon Corporation) or aromatic hydrocarbon solvents. The preferred concentration of the marker in the solvent is from 20% to 30%.
- The developing reagent is a strongly basic reagent, e.g., a hydroxide of an alkali metal or of a quaternary ammonium ion. Preferably, the reagent is a quaternary ammonium hydroxide.
- This invention is further directed to the compound of formula I in which R 1 is propyl, R2 is methyl, and R3, R4, and R5 are hydrogen. Preparation of this compound is described in Example 1.
- To a 100 mL, three-neck round-bottom flask fitted with a stirrer, thermocouple and a condenser, the following raw materials were added: (1) o-cresolphthalein, 1.73 g (0.005 moles); (2) water, 30 mL; (3) 50% NaOH, 0.8 g; (4) Na 2CO3, 0.6 g; and (5) xylenes, 8 g. The mixture was stirred at 20-25° C. for one hour, during which butyric anhydride, 2 g, was added. The mixture was then heated to 50-55° C. until TLC revealed that the esterification reaction was complete. The upper xylenes layer was separated and 1-octyl-2-pyrrolidone, 2.5 g was added to it. Xylenes and water were removed azeotropically under vacuum. A residue of 6.6 g was obtained.
- A marker solution was prepared by dissolving a 100 mg portion of the residue in xylenes (100 mL), and diluting 1 mL of the resulting solution to 100 mL with kerosene to make a 10 ppm solution.
- A developer was made by dissolving 1 g of a 40% solution of benzyltrimethylammonium hydroxide in methanol in 99 g of 2-ethyl-1-hexanol. To a 10 mL portion of the 10 ppm marker solution prepared above was added 2.5 mL of the developer. After the mixture was shaken for a few seconds, it acquired a blue-purple color. If necessary, quantitative determination of the marker concentration can be accomplished by measuring the absorbance of the solution at a wavelength of 581 nm.
- A 10 mL portion of the 10 ppm solution prepared above was stirred with 10 mL of water for ½ hour and the layers were separated. To the organic layer was added 2 mL of the developer solution, resulting in development of a blue-purple color. Addition of 2 mL of developer solution to the water layer gave no color. This indicated that the marker was not extracted into the water layer.
Claims (10)
1. A composition comprising a liquid petroleum product and a compound having the formula
wherein R1 is C1-C18 alkyl, C1-C18 alkenyl, aryl or aralkyl; R2, R3 and R4 are independently hydrogen, C1-C12 alkyl, chloro or bromo; and R5 is hydrogen, chloro or bromo; and wherein said compound is present in an amount that is not detectable visually.
2. The composition of claim 1 in which said compound is present in an amount from 0.5 ppm to 100 ppm.
3. The composition of claim 2 in which said liquid petroleum product is gasoline, diesel fuel, jet fuel, fuel oil, kerosene or lamp oil.
4. The composition of claim 3 in which R2, R3 and R4 are hydrogen or alkyl having from one to four carbon atoms.
5. The composition of claim 4 which R1 is alkyl having from one to four carbon atoms and R5 is hydrogen.
6. A compound having the formula
7. A method of marking a liquid petroluem product comprising adding to the petroleum product as a marker a compound of formula
wherein R1 is C1-C18 alkyl, C1-C18 alkenyl, aryl or aralkyl; R2, R3 and R4 are independently hydrogen, C1-C12 alkyl, chloro or bromo; and R5 is hydrogen, chloro or bromo; wherein the compound is not detectable visually, and wherein the compound develops a color on contact with a developing reagent.
8. The method of claim 7 in which said compound is present in an amount from 0.05 ppm to 100 ppm.
9. The method of claim 8 in which said liquid petroleum product is gasoline, diesel fuel, jet fuel, fuel oil, kerosene or lamp oil.
10. The method of claim 9 in which R2, R3 and R4 are hydrogen or alkyl having from one to four carbon atoms, R1 is alkyl having from one to four carbon atoms and R5 is hydrogen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/954,373 US20020038064A1 (en) | 2000-09-26 | 2001-09-17 | Colorless petroleum marker dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23550000P | 2000-09-26 | 2000-09-26 | |
| US09/954,373 US20020038064A1 (en) | 2000-09-26 | 2001-09-17 | Colorless petroleum marker dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20020038064A1 true US20020038064A1 (en) | 2002-03-28 |
Family
ID=22885760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/954,373 Abandoned US20020038064A1 (en) | 2000-09-26 | 2001-09-17 | Colorless petroleum marker dyes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20020038064A1 (en) |
| EP (1) | EP1191084A2 (en) |
| JP (1) | JP2002146371A (en) |
| KR (1) | KR20020024783A (en) |
| BR (1) | BR0104274A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030129758A1 (en) * | 1999-06-30 | 2003-07-10 | Smith Michael J. | Aromatic esters for marking or tagging organic products |
| KR100398506B1 (en) * | 2001-06-13 | 2003-09-19 | 오리엔트화학 (주) | Marker for idetification curable silicone composition having slip property |
| US20060004110A1 (en) * | 2004-06-17 | 2006-01-05 | Sabnis Ram W | Composition and method for producing colored bubbles |
| US20060222675A1 (en) * | 2005-03-29 | 2006-10-05 | Sabnis Ram W | Personal care compositions with color changing indicator |
| US20060222601A1 (en) * | 2005-03-29 | 2006-10-05 | Sabnis Ram W | Oral care compositions with color changing indicator |
| US20060236470A1 (en) * | 2005-03-29 | 2006-10-26 | Sabnis Ram W | Novelty compositions with color changing indicator |
| US20060257439A1 (en) * | 2005-03-29 | 2006-11-16 | Sabnis Ram W | Cleansing compositions with color changing indicator |
| US20070010400A1 (en) * | 2005-07-06 | 2007-01-11 | Sabnis Ram W | Use of color changing indicators in consumer products |
| KR20150025864A (en) * | 2013-08-30 | 2015-03-11 | 에스케이이노베이션 주식회사 | Petroleum Markers and identifying method of petroleum using it |
| CN109923412A (en) * | 2016-08-24 | 2019-06-21 | 联合色彩制造股份有限公司 | Mark compositions and production and preparation method thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100645357B1 (en) * | 2005-08-22 | 2006-11-14 | 심현호 | Fluorescent marker comprising double bond ester group and method for markng and detecting the same |
| KR20060018801A (en) * | 2005-09-02 | 2006-03-02 | 심현호 | Lactone marker comprising double bond ester group and method for markng and detecting the same |
| KR100846568B1 (en) * | 2005-09-02 | 2008-07-15 | 심현호 | Lactone marker comprising double bond ester group and method for marking and detecting the same |
| TWI516468B (en) * | 2012-07-06 | 2016-01-11 | 羅門哈斯公司 | Tritylated alkyl aryl ethers |
-
2001
- 2001-09-13 EP EP01307809A patent/EP1191084A2/en not_active Withdrawn
- 2001-09-14 KR KR1020010056668A patent/KR20020024783A/en not_active Application Discontinuation
- 2001-09-17 US US09/954,373 patent/US20020038064A1/en not_active Abandoned
- 2001-09-19 JP JP2001284464A patent/JP2002146371A/en not_active Withdrawn
- 2001-09-25 BR BR0104274-2A patent/BR0104274A/en not_active IP Right Cessation
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7163827B2 (en) * | 1999-06-30 | 2007-01-16 | United Color Manufacturing, Inc. | Aromatic esters for marking or tagging organic products |
| US20030129758A1 (en) * | 1999-06-30 | 2003-07-10 | Smith Michael J. | Aromatic esters for marking or tagging organic products |
| KR100398506B1 (en) * | 2001-06-13 | 2003-09-19 | 오리엔트화학 (주) | Marker for idetification curable silicone composition having slip property |
| US20060004110A1 (en) * | 2004-06-17 | 2006-01-05 | Sabnis Ram W | Composition and method for producing colored bubbles |
| US7910531B2 (en) | 2004-06-17 | 2011-03-22 | C2C Technologies Llc | Composition and method for producing colored bubbles |
| US20060222675A1 (en) * | 2005-03-29 | 2006-10-05 | Sabnis Ram W | Personal care compositions with color changing indicator |
| US20060257439A1 (en) * | 2005-03-29 | 2006-11-16 | Sabnis Ram W | Cleansing compositions with color changing indicator |
| US20060236470A1 (en) * | 2005-03-29 | 2006-10-26 | Sabnis Ram W | Novelty compositions with color changing indicator |
| US20060222601A1 (en) * | 2005-03-29 | 2006-10-05 | Sabnis Ram W | Oral care compositions with color changing indicator |
| US20070010400A1 (en) * | 2005-07-06 | 2007-01-11 | Sabnis Ram W | Use of color changing indicators in consumer products |
| KR20150025864A (en) * | 2013-08-30 | 2015-03-11 | 에스케이이노베이션 주식회사 | Petroleum Markers and identifying method of petroleum using it |
| KR102027114B1 (en) | 2013-08-30 | 2019-10-11 | 에스케이이노베이션 주식회사 | Petroleum Markers and identifying method of petroleum using it |
| CN109923412A (en) * | 2016-08-24 | 2019-06-21 | 联合色彩制造股份有限公司 | Mark compositions and production and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020024783A (en) | 2002-04-01 |
| BR0104274A (en) | 2002-06-04 |
| EP1191084A2 (en) | 2002-03-27 |
| JP2002146371A (en) | 2002-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |