WO2024039329A2 - Use of anthrapyridone dyes for marking liquid products - Google Patents
Use of anthrapyridone dyes for marking liquid products Download PDFInfo
- Publication number
- WO2024039329A2 WO2024039329A2 PCT/TR2023/050565 TR2023050565W WO2024039329A2 WO 2024039329 A2 WO2024039329 A2 WO 2024039329A2 TR 2023050565 W TR2023050565 W TR 2023050565W WO 2024039329 A2 WO2024039329 A2 WO 2024039329A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fuel
- hydrocarbon
- compound
- label
- following formula
- Prior art date
Links
- 239000000975 dye Substances 0.000 title abstract description 51
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical compound C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 title abstract description 22
- 239000012263 liquid product Substances 0.000 title description 2
- 239000000446 fuel Substances 0.000 claims abstract description 76
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 60
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 60
- 239000007788 liquid Substances 0.000 claims abstract description 47
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 45
- -1 crude oil Chemical class 0.000 claims abstract description 23
- 239000010779 crude oil Substances 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000011550 stock solution Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002105 nanoparticle Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 10
- 239000000047 product Substances 0.000 description 23
- 230000003287 optical effect Effects 0.000 description 13
- JZGUXCXDBKBCDN-UHFFFAOYSA-N 21295-57-8 Chemical compound C12=C3C(=O)C4=CC=CC=C4C1=CC(=O)N(C)C2=CC=C3NC1CCCCC1 JZGUXCXDBKBCDN-UHFFFAOYSA-N 0.000 description 9
- 239000003550 marker Substances 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 5
- VJUKWPOWHJITTP-UHFFFAOYSA-N 81-39-0 Chemical compound C1=CC(C)=CC=C1NC1=CC=C2C3=C1C(=O)C1=CC=CC=C1C3=CC(=O)N2C VJUKWPOWHJITTP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- VKWNTWQXVLKCSG-UHFFFAOYSA-N n-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- BATVZJPOLFSGTD-WCWDXBQESA-N solvent yellow 124 Chemical compound C1=CC(N(CCOC(C)OCC(C)C)CC)=CC=C1\N=N\C1=CC=CC=C1 BATVZJPOLFSGTD-WCWDXBQESA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- 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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
-
- 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
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/16—Tracers which serve to track or identify the fuel component or fuel composition
Definitions
- the present invention relates to dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- the marker in the fuel is determined qualitatively and quantitatively by using the absorbent property of the molecule; however, the fluorescent-based fuel labels utilize the fluorescent property of the molecule for the same purpose.
- the molecules used as optical markers can also be called dyes due to the content of chromophore. For this reason, some dyes can be used as fuel labels in the state of the art.
- US2007/0266895A1 discloses molecular structure and use of an absorbance-based fuel label, highly soluble in aliphatic hydrocarbons.
- US2015/9222043 B2 discloses fluorescent dyes and their use as fuel labels.
- GB2535179A1 discloses use of azo dyes as hydrocarbon fuel labels.
- Solvent Yellow 124, Solvent Red19 and Solvent Orange 2 are preferred as azo dyes.
- the present invention discloses a compound of general formula (I):
- RT represents hydrogen, or a substituted or unsubstituted alkyl, aryl, benzoyl, hetaryl, alkoxy or phenoxy group;
- R 2 represents hydrogen, or a substituted or unsubstituted alkyl, alicyclic, aryl or hetaryl group
- R 3 represents hydrogen, carboxyl, or a substituted or unsubstituted alkyl, alicyclic, aryl, hetaryl, alkoxy or phenoxy group; for use as a hydrocarbon and/or fuel and/or brand label.
- the present invention further provides a label containing the at least one compound, which is suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- the present invention provides a production method comprising the steps of: dissolving the at least one compound in at least one organic solvent for the production of said label; and obtaining a master stock solution for use as a label for hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- the present invention provides dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. According to the present invention, low-cost fuel/product labels without a risk of copying are provided, which ensure safe supply and sale of fuels/products.
- An object of the present invention is to provide dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- Another object of the present invention is to provide dyes containing anthrapyridone dye structure for use as fuel/product labels to ensure the safe supply and sale of fuels/products.
- a further object of the present invention is to provide a label suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- Still another object of the present invention is to provide a production method for a label suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- Figure 1 is a view of the Ultraviolet-Vis (UV-Vis) spectrum graph of Solvent Red 149 dye containing anthrapyridone dye structure.
- Figure 2 is a view of the Fluorescent spectrum graph of Solvent Red 149 dye containing anthrapyridone dye structure.
- Fuel manufacturers and distributors provide a fuel label on the fuel to be sold in order to ensure safety in the fuel industry and to prevent introduction of illegal fuels into the market.
- fuel labels called “optical markers” and “molecular markers” are added to fuel products.
- Said “optical marker” fuel labels provide quick analysis and results.
- the fuel labels called optical markers are classified as absorbance-based fuel labels and fluorescent-based fuel labels.
- the marker in the fuel is determined qualitatively and quantitatively by using the absorbent property of the molecule; however, the fluorescentbased fuel labels utilize the fluorescent property of the molecule for the same purpose.
- the molecules used as optical markers can also be called dyes due to the content of chromophore.
- the present invention provides use of dyes containing anthrapyridone dye structure as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- the present invention discloses a compound of general formula (I):
- RT represents hydrogen, or a substituted or unsubstituted alkyl, aryl, benzoyl, hetaryl, alkoxy or phenoxy group;
- R 2 represents hydrogen, or a substituted or unsubstituted alkyl, alicyclic, aryl or hetaryl group
- R 3 represents hydrogen, carboxyl, or a substituted or unsubstituted alkyl, alicyclic, aryl, hetaryl, alkoxy or phenoxy group; for use as a hydrocarbon and/or fuel and/or brand label.
- the compound of general formula (I) provided in the present invention represents the anthrapyridone dye structure.
- the present invention provides specific use of Solvent Red 52, Solvent Red 149 and Solvent Red 150 dyes with the following molecular structures, preferably containing anthrapyridone dye structure, as hydrocarbon and/or fuel and/or brand labels:
- the present invention provides a label suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- Said label comprises at least one compound of said general formula (I) (here, said general formula (I) represents at least one compound having anthrapyridone dye structure).
- the present invention provides a production method for said label used in hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- said production method there is obtained the at least one compound of the general formula (I), and a master stock solution dissolved in at least one organic solvent and used as a label for hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
- Said compound of general formula (I) represents an anthrapyridone dye structure.
- dyes containing said anthrapyridone dye structure are supplied in powder form in high purity or in high concentration in liquid.
- the supplied dye containing the anthrapyridone dye structure is dissolved in a stable and high solubility organic solvent (specifically, preferably alcoholic solvents, aromatic solvents, aliphatic solvents, fuels and refinery products; more specifically, preferably benzyl alcohol, ethyl alcohol, methyl alcohol, xylene, toluene, ethyl benzene, gasoline, diesel, biodiesel, naphtha and reformate) to obtain the master stock solution.
- a stable and high solubility organic solvent specifically, preferably alcoholic solvents, aromatic solvents, aliphatic solvents, fuels and refinery products; more specifically, preferably benzyl alcohol, ethyl alcohol, methyl alcohol, xylene, toluene, ethyl benzene, gasoline, diesel, biodiesel, naphtha and reformate
- Said master stock solution is prepared to have a dye/solvent ratio in the range of 0.1-80% by weight.
- Said master stock solution should be able to store the dye in a stable state for a certain period of time (for example, preferably for 12 months) when not in use. Therefore, preferably, co- solvents/chemicals (specifically, preferably, oleic acid and ethylene glycol) can be added to improve the stability and solubility performance of the master stock solution.
- a hybrid mixture can be obtained by adding a plurality of dyes and/or materials with similar optical properties to the master stock solution.
- Dyes with similar optical properties UV, fluorescent
- materials with similar optical properties specifically, preferably, organic/inorganic based quantum particles
- CdSe nanoparticles may be exemplified as the inorganic particles
- carbon quantum dots may be exemplified as the organic particles.
- the master stock solution in a stable state is added into liquid hydrocarbon products and/or fuel (tank, fuel tank or storage) in quite small amounts (0.01-10 ppm). Said addition process can be performed manually or automatically with the injection system.
- the dye containing anthrapyridone dye structure contained in the master stock solution injected into the fuel can be determined qualitatively and quantitatively by means of a spectroscopic method (UV-Vis and/or fluorescent spectroscopy).
- the UV-Vis and Fluorescent spectra of Solvent Red 149 dye which is exemplified as a dye containing anthrapyridone dye structure, are illustrated in Figure 1 and Figure 2.
- the label in the fuel can be detected qualitatively and quantitatively by using HPLC or GC system.
- an HPLC system with UV-Vis and/or fluorescence detector is capable of detecting Solvent Red 149 dye in fuel with high sensitivity and reliability.
- the present invention provides dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. According to the present invention, low-cost fuel/product labels without a risk of copying are provided, which ensure safe supply and sale of fuels/products.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Electrochemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
The present invention discloses dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. In addition, the present invention discloses a label comprising said dye structure, and a production method thereof.
Description
USE OF ANTHRAPYRIDONE DYES FOR MARKING LIQUID PRODUCTS
Technical Field
The present invention relates to dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
Background of the Invention
National or international markets require to establish a secure supply chain for the regular follow-up of the products produced. For example, many countries and/or fuel manufacturers and distributors add fuel labels to the fuels to be sold, in order to ensure safety in the fuel industry and to prevent introduction of illegal fuels into the market. According to the prior art, a fuel label mixture containing two different marker molecules/materials is added to fuel products. One of the mentioned marker molecules is a fuel label called "optical marker", which can be analyzed quickly with faster results. If fuel labels with optical markers does not produce reliable results, fuel labels called “molecular markers” are preferred, which can be determined by a more detailed analysis. The fuel labels known as optical markers are classified as absorbance-based fuel labels and fluorescent-based fuel labels. According to said absorbance-based fuel labels, the marker in the fuel is determined qualitatively and quantitatively by using the absorbent property of the molecule; however, the fluorescent-based fuel labels utilize the fluorescent property of the molecule for the same purpose. The molecules used as optical markers can also be called dyes due to the content of chromophore. For this reason, some dyes can be used as fuel labels in the state of the art.
US2007/0266895A1 discloses molecular structure and use of an absorbance-based fuel label, highly soluble in aliphatic hydrocarbons.
US2015/9222043 B2 discloses fluorescent dyes and their use as fuel labels.
GB2535179A1 discloses use of azo dyes as hydrocarbon fuel labels. Solvent Yellow 124, Solvent Red19 and Solvent Orange 2 are preferred as azo dyes.
Although some studies have been conducted on dyes with optical properties for use as fuel labels in the prior art, further studies are required to use dyes with different structures as fuel labels.
Brief Description of the Invention
The present invention discloses a compound of general formula (I):
(I), wherein
RT represents hydrogen, or a substituted or unsubstituted alkyl, aryl, benzoyl, hetaryl, alkoxy or phenoxy group;
R2 represents hydrogen, or a substituted or unsubstituted alkyl, alicyclic, aryl or hetaryl group;
R3 represents hydrogen, carboxyl, or a substituted or unsubstituted alkyl, alicyclic, aryl, hetaryl, alkoxy or phenoxy group; for use as a hydrocarbon and/or fuel and/or brand label.
The present invention further provides a label containing the at least one compound, which is suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
In addition, the present invention provides a production method comprising the steps of: dissolving the at least one compound in at least one organic solvent for the production of said label; and obtaining a master stock solution for use as a label for hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
The present invention provides dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. According to the present invention, low-cost fuel/product labels without a risk of copying are provided, which ensure safe supply and sale of fuels/products.
Object of the Invention
An object of the present invention is to provide dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
Another object of the present invention is to provide dyes containing anthrapyridone dye structure for use as fuel/product labels to ensure the safe supply and sale of fuels/products.
A further object of the present invention is to provide a label suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
Still another object of the present invention is to provide a production method for a label suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
Description of the Drawings
Test results of dyes containing anthrapyridone dye structure according to the present invention, which are used as a hydrocarbon and/or fuel and/or brand label, are illustrated in the attached drawings, in which:
Figure 1 is a view of the Ultraviolet-Vis (UV-Vis) spectrum graph of Solvent Red 149 dye containing anthrapyridone dye structure.
Figure 2 is a view of the Fluorescent spectrum graph of Solvent Red 149 dye containing anthrapyridone dye structure.
All the parts illustrated in figures are individually assigned a reference numeral and the corresponding terms of these numbers are listed below:
The curve illustrating the excitation wavelength of 551 nm in the fluorescence spectrum graph of Solvent Red 149 dye containing anthrapyridone dye structure (2a)
The curve illustrating the excitation wavelength of 518 nm in the fluorescence spectrum graph of Solvent Red 149 dye containing anthrapyridone dye structure (2b)
Description of the Invention
Fuel manufacturers and distributors provide a fuel label on the fuel to be sold in order to ensure safety in the fuel industry and to prevent introduction of illegal fuels into the market. According to the known-state of the art, fuel labels called "optical markers" and "molecular markers" are added to fuel products. Said “optical marker” fuel labels provide quick analysis and results. The fuel labels called optical markers are classified as absorbance-based fuel labels and fluorescent-based fuel labels. According to said absorbance-based fuel labels, the marker in the fuel is determined qualitatively and quantitatively by using the absorbent property of the molecule; however, the fluorescentbased fuel labels utilize the fluorescent property of the molecule for the same purpose. The molecules used as optical markers can also be called dyes due to the content of chromophore. The present invention provides use of dyes containing anthrapyridone dye structure as labels/seals/markers for organic solvents, hydrocarbon liquid fuels,
combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
The present invention discloses a compound of general formula (I):
(I), wherein
RT represents hydrogen, or a substituted or unsubstituted alkyl, aryl, benzoyl, hetaryl, alkoxy or phenoxy group;
R2 represents hydrogen, or a substituted or unsubstituted alkyl, alicyclic, aryl or hetaryl group;
R3 represents hydrogen, carboxyl, or a substituted or unsubstituted alkyl, alicyclic, aryl, hetaryl, alkoxy or phenoxy group; for use as a hydrocarbon and/or fuel and/or brand label.
The compound of general formula (I) provided in the present invention represents the anthrapyridone dye structure. The present invention provides specific use of Solvent Red 52, Solvent Red 149 and Solvent Red 150 dyes with the following molecular structures, preferably containing anthrapyridone dye structure, as hydrocarbon and/or fuel and/or brand labels:
Solvent Red 52 Solvent Red 149 Solvent Red 150
The present invention provides a label suitable for use with hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. Said label comprises at least one compound of said general formula (I) (here, said general formula (I) represents at least one compound having anthrapyridone dye structure).
The present invention provides a production method for said label used in hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. In said production method, there is obtained the at least one compound of the general formula (I), and a master stock solution dissolved in at least one organic solvent and used as a label for hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. Said compound of general formula (I) represents an anthrapyridone dye structure.
In an embodiment of the invention, dyes containing said anthrapyridone dye structure (specifically, preferably Solvent Red 52, Solvent Red 149 and Solvent Red 150) are supplied in powder form in high purity or in high concentration in liquid. The supplied dye containing the anthrapyridone dye structure is dissolved in a stable and high solubility organic solvent (specifically, preferably alcoholic solvents, aromatic solvents, aliphatic solvents, fuels and refinery products; more specifically, preferably benzyl alcohol, ethyl alcohol, methyl alcohol, xylene, toluene, ethyl benzene, gasoline, diesel, biodiesel, naphtha and reformate) to obtain the master stock solution. Said master stock solution is prepared to have a dye/solvent ratio in the range of 0.1-80% by weight. Said master stock
solution should be able to store the dye in a stable state for a certain period of time (for example, preferably for 12 months) when not in use. Therefore, preferably, co- solvents/chemicals (specifically, preferably, oleic acid and ethylene glycol) can be added to improve the stability and solubility performance of the master stock solution.
A hybrid mixture can be obtained by adding a plurality of dyes and/or materials with similar optical properties to the master stock solution. Dyes with similar optical properties (UV, fluorescent) and/or materials with similar optical properties (specifically, preferably, organic/inorganic based quantum particles) can also be added to said master stock solution. CdSe nanoparticles may be exemplified as the inorganic particles, and carbon quantum dots may be exemplified as the organic particles.
The master stock solution in a stable state is added into liquid hydrocarbon products and/or fuel (tank, fuel tank or storage) in quite small amounts (0.01-10 ppm). Said addition process can be performed manually or automatically with the injection system. The dye containing anthrapyridone dye structure contained in the master stock solution injected into the fuel can be determined qualitatively and quantitatively by means of a spectroscopic method (UV-Vis and/or fluorescent spectroscopy). The UV-Vis and Fluorescent spectra of Solvent Red 149 dye, which is exemplified as a dye containing anthrapyridone dye structure, are illustrated in Figure 1 and Figure 2. In addition to optical detection methods, the label in the fuel can be detected qualitatively and quantitatively by using HPLC or GC system. For example, an HPLC system with UV-Vis and/or fluorescence detector is capable of detecting Solvent Red 149 dye in fuel with high sensitivity and reliability.
The present invention provides dyes containing anthrapyridone dye structure for use as labels/seals/markers for organic solvents, hydrocarbon liquid fuels, combustible materials, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products. According to the present invention, low-cost fuel/product labels without a risk of copying are provided, which ensure safe supply and sale of fuels/products.
Claims
1. A compound of general formula (I):
wherein
RT represents hydrogen, or a substituted or unsubstituted alkyl, aryl, benzoyl, hetaryl, alkoxy or phenoxy group;
R2 represents hydrogen, or a substituted or unsubstituted alkyl, alicyclic, aryl or hetaryl group;
R3 represents hydrogen, carboxyl, or a substituted or unsubstituted alkyl, alicyclic, aryl, hetaryl, alkoxy or phenoxy group; for use as a hydrocarbon and/or fuel and/or brand label.
2. A compound of the following formula according to claim 1 :
for use as a hydrocarbon and/or fuel and/or brand label.
3. A compound of the following formula according to claim 1 :
RT represents hydrogen, or a substituted or unsubstituted alkyl, aryl, benzoyl, hetaryl, alkoxy or phenoxy group;
R2 represents hydrogen, or a substituted or unsubstituted alkyl, alicyclic, aryl or hetaryl group;
R3 represents hydrogen, carboxyl, or a substituted or unsubstituted alkyl, alicyclic, aryl, hetaryl, alkoxy or phenoxy group. A production method for a label according to claim 10, characterized by comprising the steps of dissolving the at least one compound of the general formula (I) in at least one organic solvent and obtaining a master stock solution for use as a label for hydrocarbon liquid fuels, combustibles, liquid hydrocarbons such as crude oil, and liquid hydrocarbon products.
12. A production method according to claim 11 , characterized in that said organic solvent comprises alcoholic solvents, aromatic solvents, aliphatic solvents, fuels and/or refinery products.
13. A production method according to claim 11 , characterized in that ratio of said compound to said organic solvent is in the range of 0.1-80% by weight.
14. A production method according to claim 11, characterized in that it comprises the step of adding at least one solvent and/or chemical to the master stock solution.
15. A production method according to claim 14, characterized in that said solvent and/or chemical is oleic acid and/or ethylene glycol. 16. A production method according to claim 11, characterized in that it comprises the step of adding CdSe nanoparticles and/or carbon quantum dots into said master stock solution.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2022013065 | 2022-08-18 | ||
| TR2022/013065 TR2022013065A2 (en) | 2022-08-18 | Use of antrapyridone dyes to label liquid products. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2024039329A2 true WO2024039329A2 (en) | 2024-02-22 |
| WO2024039329A3 WO2024039329A3 (en) | 2024-08-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/TR2023/050565 WO2024039329A2 (en) | 2022-08-18 | 2023-06-13 | Use of anthrapyridone dyes for marking liquid products |
Country Status (1)
| Country | Link |
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| WO (1) | WO2024039329A2 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104725315A (en) * | 2013-12-21 | 2015-06-24 | 江苏道博化工有限公司 | Method used for preparing solvent red 149 |
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- 2023-06-13 WO PCT/TR2023/050565 patent/WO2024039329A2/en unknown
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| Publication number | Publication date |
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| WO2024039329A3 (en) | 2024-08-22 |
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