CA2193886A1 - Use of carbonyl compounds for marking hydrocarbons - Google Patents
Use of carbonyl compounds for marking hydrocarbonsInfo
- Publication number
- CA2193886A1 CA2193886A1 CA002193886A CA2193886A CA2193886A1 CA 2193886 A1 CA2193886 A1 CA 2193886A1 CA 002193886 A CA002193886 A CA 002193886A CA 2193886 A CA2193886 A CA 2193886A CA 2193886 A1 CA2193886 A1 CA 2193886A1
- Authority
- CA
- Canada
- Prior art keywords
- carbonyl compounds
- alkyl
- hydrocarbons
- formula
- markers
- 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
Links
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- C—CHEMISTRY; METALLURGY
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
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- C10L1/14—Organic compounds
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- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
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- 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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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; viscous liquids; paints; inks
- G01N33/28—Oils, i.e. hydrocarbon liquids
- G01N33/2835—Oils, i.e. hydrocarbon liquids specific substances contained in the oil or fuel
- G01N33/2882—Markers
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- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
- C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
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- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
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- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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Abstract
The invention concerns the use of .beta.-dicarbonyl or aromatic orthohydroxycarbonyl compounds to mark hydrocarbons, as well as hydrocarbons containing .beta.-dicarbonyl or aromatic ortho-hydroxycarbonyl compounds as markers and a method of assaying .beta.-dicarbonyl or aromatic orthohydroxycarbonyl compounds in hydrocarbons.
Description
O.Z. 1800/01002 , The use of carbonyl compounds as markers for hydrocarbons The present invention relates to the use of carbonyl compounds as 5 markers for hydrocarbons, to hydrocarbons contA;ning carbonyl compounds as markers, and to a method for detecting carbonyl compounds in hydrocarbons.
Markers are added to the hydrocarbons, eg. petroleum refinery 10 products, as a rule for tax reasons because the tax on a particular product may vary depending on the purpose for which it is used. For example, as a rule, heating oil contains a marker because it is taxed at a considerably lower rate than diesel oil which has an identical composition.
Markers suitable for hydrocarbons ought in particular - to have adequate stability under the usual conditions of use, 20 - to cause no change in the physico-chemical properties of the fuel or solvent, - to have sufficient stability so that they can also be used in the form of highly concentrated solutions, - to be removable by simple chemical or physical methods from the medium contA; n ing them, - to be usable even in small amounts, - to be detectable by simple, fast and sensitive detection methods and - to be toxicologically acceptable.
It is an object of the present invention to provide novel markers for hydrocarbons which are liquids or can be liquified by compression. Markers of this type should be readily available and have the abovementioned profile of properties.
We have found that this object is achieved by carbonyl compounds of the formula R1-C0-CH2-C0-R2 (I) or ~ '~ ~ 2 21 93~6 OH
(II), Ll L2 where 10 Rl is hydrogen, Cl-C4-alkyl, Cl-C4-alkoxy or a radical of the formula ~zl z2 where X is a direct linkage, oxygen or imino, and Zl and Z2 are each, independently of one another, hydrogen, Cl-C4-alkyl, Cl-C4-alkoxy or halogen, R2 is hydrogen, C1-C4-alkyl or a radical of the formula ~zl z2 where X, Z1 and Z2 each have the abovementioned meanings, R3 is hydrogen, hydroxyl, C1-C4-alkyl or C1-C4-alkoxy and L1 and L2 are each, independently of one another hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy or halogen, and ring A can be benzo-fused, which are suitable and advantageous as 35 markers for hydrocarbons.
All the alkyl groups in the abovementioned formulae can be either straight-chain or branched.
40 Examples of radicals R1, R2, R3, L1, L2, Z1 and Z2 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
Further examples of radicals R1, R3, L1, L2, zl and Z2 are methoxy, 45 ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy.
3 21 93~86 Further examples of radicals L1, L2, zl and Z2 are fluorine, ~ chlorine or bromine.
A marker means for the purpose of the invention a compound, such 5 as the carbonyl compounds of the formula I and/or II, which on addition to hydrocarbons causes no change in the hydrocarbons which is visible to the human eye, but the carbonyl compounds of the formula I and~or II can be easily and clearly visibly detected by the detection methods described in detail herein.
Hydrocarbons mean for the purpose of the invention in general those products resulting from petroleum refining. Examples of these are propane, butane, pentane, hexane, heptane, octane, isooctane, benzene, toluene, xylene, ethylbenzene, tetralin, 15 decAl; n or dimethylnaphthalene. They are, in particular, mineral oils, for example motor fuels such as gasoline, kerosine or diesel oil, or oils such as heating oil or engine oil.
They furthermore include products resulting from the processing 20 of certain types of plants, eg. rape or sunflower. Products of this type are also known under the name biodiesel.
At standard temperature and pressure, the hydrocarbons are generally in the liquid state of aggregation, or they are in the 25 gaseous state of aggregation and can be liquified for example by compression, eg. liquified gas such as propane or butane.
It is self-evident that the carbonyl co...~ounds of the formulae I
and II can be used not only as markers for hydrocarbons. They can 30 also be used with similar success as markers for other organic solvents.
The carbonyl c~...pounds of the formula I which are preferably used as markers are those where Rl is Cl-C4-alkyl, Cl-C4-alkoxy or a 35 radical of the formula NH ~ z2 where Z1 and ZZ each have the abovementioned meanings, and R2 is Cl-C4-alkyl .
.
1800iO1002 2 1 ~3~6 Furthermore preferably used as markers are carbonyl compounds of - the formula II where R3 is hydrogen, hydroxyl or Cl-C4-alkoxy, especially hydrogen or hydroxyl, and Ll and L2 are each hydrogen, and ring A is not benzo-fused.
Carbonyl compounds of the formula I where Rl is Cl-C4-alkyl or Cl-C4-alkoxy and R2 is Cl-C4-alkyl are particularly preferably used as markers.
10 The use of carbonyl compounds of the formula I where Rl and R2 are each, independently of one another, Cl-C4-alkyl, especially methyl, as markers is particularly important.
The carbonyl co.,.pounds of the formula I and/or II are used either 15 undiluted or in the form of solutions as markers for hydrocarbons. Suitable solvents are organic solvents. Preferably used are aromatic hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatic compounds which is commercially available under the name 20 Shellsol~ AB (from Shell). The concentration of carbonyl compound chosen is generally from 20 to 80% of the weight of the solution.
It is also possible to use other cosolvents, eg. alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, 25 pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol, glycols, such as butylethylene glycol or methylpropylene glycol, amines such as triethylamine, diisooctylamine, dicyclohexylamine, An;l;ne~ N-methylAn;l;ne~
N,N-dimethylAn;l;ne, toluidine or xylidine, alkanolamines such as 30 3-(2-methoxyethoxy)propylamine, o-cresol, m-cresol, p-cresol, ketones such as diethyl ketone or cyclohexanone, lactones such as ~-butyrolactone, carbonates such as ethylene carbonate or propylene carbonate, phenols such as t-butylphenol or nonylphenol, esters such as methyl phthalate, ethyl phthalate, 35 2-ethylhexyl phthalate, ethyl acetate, butyl acetate or cyclohexyl acetate, amides such as N,N-dimethylformamide, N,N-diethylacetamide or N-methylpyrrolidinone, or mixtures thereof.
40 The present invention further relates to hydrocarbons contA;n;ng one or more carbonyl cv.,.pounds of the formula I and/or II a markers.
The hydrocarbons preferably have a content of from 5 to 1000 ppm, - in particular 10 to 1000 ppm, of marker. A content of from 10 to 500 ppm, in particular 50 to 100 ppm, should be particularly emphasized in this context.
It is expedient in practice to tend to use larger amounts of marker so that testing of the marker-cont~;n;ng hydrocarbon gives a positive reaction in every case, especially in view of the possibility of the hydrocarbon being diluted in the case of 10 fraud.
Besides the carbonyl compounds of the formula I and/or II it is possible for the hydrocarbons also to contain other conventional markers or denaturing agents such as furfurol or C.I. Solvent 15 Red 198.
We have furthermore found that the carbonyl compounds of the abovementioned formulae I and/or II can advantageously be detected in hydrocarbons when the hydrocarbons are treated with a 20 solution of an iron(III) salt in aqueous alcohol or aqueous acetone.
Examples of suitable iron(III) salts are iron(III) halides such as iron(III) chloride or iron(III) bromide, iron(III) sulfate, 25 iron(III) nitrate or iron(III) acetate. The use of iron(III) chloride is preferred.
The iron(III) salts are used in solution in aqueous alcohol or aqueous acetone. The use of a solution in aqueous alcohol is 30 preferred.
Examples of suitable alcohols for preparing the solution in aqueous alcohol are methanol, ethanol, propanol or isopropanol.
The use of methanol or ethanol is preferred, and the use of 35 methanol should be particularly emphasized.
Suitable reagent solution~ generally have a content of from 0.05 to 0.5% by weight, preferably 0.1 to 0.3% by weight, of iron(III) salts, 10 to 90% by weight, preferably 40 to 70% by weight, of an 40 alcohol or acetone and 10 to 90~ by weight, preferably 30 to 60%
by weight, of water, in each case based on the weight of the reagent solution, the overall total of the ingredients being, of course, 100% by weight.
45 In the investigation of hydrocarbons which are in the liquid state of aggregation at standard temperature and pressure, the test is usually carried out by vigorously shaking about 20 ml of marker-cont~in;ng hydrocarbon with about 2 ml of regent solution for about 15 to 20 seconds.
The phases are then allowed to separate. In the presence of the 5 carbonyl compounds of the formula I and/or II the lower aqueous phase has a red or violet-brown color. The color depends on the nature of the marker.
The content of marker can moreover be determined by conventional lO methods, eg. spectroscopic methods.
In the investigation of hydrocarbons which are in the gaseous state of aggregation at standard temperature and pressure but have been liquified by compression, the test is usually carried 15 out by introducing from 1 to 2 ml of reagent solution into a suitable container, eg. a test tube, and then discharging the liquified hydrocarbon, and collecting it in the container, from a gas cylinder which contains the liquified hydrocarbon for about 15 to 30 seconds. It is advantageous in this case to allow the 20 hydrocarbon to escape from the horizontal cylinder because it is usually still in the liquid state of aggregation when it escapes.
The liquified hydrocarbon is then allowed to evaporate. In the presence of the carbonyl compounds of the formula I and/or II the reagent solution then has a red or violet-brown color.
The carbonyl compounds of the formula I or II to be used according to the invention have the advantageous profile of properties defined at the outset. They are easily available and very compatible with other additives which may be present in the 30 hydrocarbons requiring markers, eg. with auxiliaries or other markers or denaturing agents.
The following examples are intended to illustrate the invention in detail.
Example 1 Liquified gas (butane) in cylinders comprising acetylacetone in a concentration of 50 ppm as marker Butane was allowed to escape from the tap of the horizontal cylinder so that it escaped in liquid form. Then 20 ml of the hydrocarbon were mixed in a test tube with 2 ml of the following reagent:
2 1 ~38~6 0.1 g of iron(III) chloride dissolved in 20 ml of water and 80 ml of methanol 5 The liquified gas had completely evaporated after 20 sec, and the reagent had a red color.
Marker-contA;n;ng propane behaves in a similar way.
10 Example 2 (Comparative) Example 1 was carried out with liquified gas cont~;ning no markers. The reagent had a yellow color.
15 Example 3 Liquified propane in cylinders comprising salicylic acid in a concentration of 50 ppm as marker 20 The test described in Example 1 was repeated. The reagent had a distinct violet color.
Marker-cont~; n; ng butane behaves in a similar way.
25 Example 4 20 ml of diesel oil comprising 50 ppm of acetylacetone as marker were placed in a separating funnel. Then 2 ml of the reagent described in Example 1 were added and the mixture was vigorously 30 shaken for 20 sec. It was then allowed to settle. After 5 min, the phases separated. The lower aqueous phase had a distinct red color.
Example 5 1 ml of the marker-cont~;n;ng diesel oil from ~mpl e 4 was diluted with 9 ml of diesel oil cont~;n;ng no marker. The method described in Example 4 was repeated with this mixture. The lower aqueous phase had a pale red color.
Example 6 (Comparative) The method described in Example 4 was carried out with 20 ml of diesel oil cont~;n;ng no marker. The lower aqueous phase remained 45 yellow.
Example 7 20 ml of diesel oil comprising 50 ppm salicylic acid as marker were introduced into a separating funnel. Then 2 ml of the 5 reagent described in Example 1 were added and the mixture was vigorously shaken for 20 sec. It was then allowed to settle.
After 5 min, the phases separated. The lower aqueous phase had a distinct violet color.
10 The examples listed in the following table were carried out in a similar way.
Example Marker Hydrocarbon Concentration Reaction No. [ppm~ color 15 8 Acetylacetone Liquified gas 50 Red (butane) 9 Acetylacetone Liquified gas~) 30 Red (butane) Acetylacetone Lead-free 50 Red gasoline 11 Acetylacetone Super 50 Red gasoline~) 12 Acetylacetone Diesel oil 50 Red Acetylacetone Diesel oil 5 Pink 14 Methyl Liquified gas 50 Red acetoacetate Methyl Diesel oil 500 Red acetoacetate 16 Methyl Lead-free 500 Red acetoacetate gasoline 17 Ethyl Lead-free 500 Red -- acetoacetate gasoline 18 Ethyl Diesel oil 500 Red acetoacetate 35 19 Butyl - Lead-free 500 Red acetoacetate gasoline Butyl Diesel oil 500 Red acetoacetate 21 N-(3-methyl- Lead-free 100 Brown phenyl)aceto- gasoline acetamide 22 N-(3-methyl- Diesel oil 100 Brown phenyl)aceto-acetamide 45 23 Salicylic Liquified gas 50 Violet acid (butane) 2~ ~3886 . g Example Marker Hydrocarbon Concentration Reaction No. [ppm] color 24 Salicylic Super 50 Violet acid gasoline~) 5 25 Salicylic Diesel oil 50 Violet acid 26 Salicylic Lead-free 500 Violet acid gasoline 27 Salicyl- Diesel oil 100 Violet aldehyde ~) additionally contains 10 ppm furfurol ~) additionally contains 20 ppm C.I. Solvent Red 198,
Markers are added to the hydrocarbons, eg. petroleum refinery 10 products, as a rule for tax reasons because the tax on a particular product may vary depending on the purpose for which it is used. For example, as a rule, heating oil contains a marker because it is taxed at a considerably lower rate than diesel oil which has an identical composition.
Markers suitable for hydrocarbons ought in particular - to have adequate stability under the usual conditions of use, 20 - to cause no change in the physico-chemical properties of the fuel or solvent, - to have sufficient stability so that they can also be used in the form of highly concentrated solutions, - to be removable by simple chemical or physical methods from the medium contA; n ing them, - to be usable even in small amounts, - to be detectable by simple, fast and sensitive detection methods and - to be toxicologically acceptable.
It is an object of the present invention to provide novel markers for hydrocarbons which are liquids or can be liquified by compression. Markers of this type should be readily available and have the abovementioned profile of properties.
We have found that this object is achieved by carbonyl compounds of the formula R1-C0-CH2-C0-R2 (I) or ~ '~ ~ 2 21 93~6 OH
(II), Ll L2 where 10 Rl is hydrogen, Cl-C4-alkyl, Cl-C4-alkoxy or a radical of the formula ~zl z2 where X is a direct linkage, oxygen or imino, and Zl and Z2 are each, independently of one another, hydrogen, Cl-C4-alkyl, Cl-C4-alkoxy or halogen, R2 is hydrogen, C1-C4-alkyl or a radical of the formula ~zl z2 where X, Z1 and Z2 each have the abovementioned meanings, R3 is hydrogen, hydroxyl, C1-C4-alkyl or C1-C4-alkoxy and L1 and L2 are each, independently of one another hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy or halogen, and ring A can be benzo-fused, which are suitable and advantageous as 35 markers for hydrocarbons.
All the alkyl groups in the abovementioned formulae can be either straight-chain or branched.
40 Examples of radicals R1, R2, R3, L1, L2, Z1 and Z2 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
Further examples of radicals R1, R3, L1, L2, zl and Z2 are methoxy, 45 ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy.
3 21 93~86 Further examples of radicals L1, L2, zl and Z2 are fluorine, ~ chlorine or bromine.
A marker means for the purpose of the invention a compound, such 5 as the carbonyl compounds of the formula I and/or II, which on addition to hydrocarbons causes no change in the hydrocarbons which is visible to the human eye, but the carbonyl compounds of the formula I and~or II can be easily and clearly visibly detected by the detection methods described in detail herein.
Hydrocarbons mean for the purpose of the invention in general those products resulting from petroleum refining. Examples of these are propane, butane, pentane, hexane, heptane, octane, isooctane, benzene, toluene, xylene, ethylbenzene, tetralin, 15 decAl; n or dimethylnaphthalene. They are, in particular, mineral oils, for example motor fuels such as gasoline, kerosine or diesel oil, or oils such as heating oil or engine oil.
They furthermore include products resulting from the processing 20 of certain types of plants, eg. rape or sunflower. Products of this type are also known under the name biodiesel.
At standard temperature and pressure, the hydrocarbons are generally in the liquid state of aggregation, or they are in the 25 gaseous state of aggregation and can be liquified for example by compression, eg. liquified gas such as propane or butane.
It is self-evident that the carbonyl co...~ounds of the formulae I
and II can be used not only as markers for hydrocarbons. They can 30 also be used with similar success as markers for other organic solvents.
The carbonyl c~...pounds of the formula I which are preferably used as markers are those where Rl is Cl-C4-alkyl, Cl-C4-alkoxy or a 35 radical of the formula NH ~ z2 where Z1 and ZZ each have the abovementioned meanings, and R2 is Cl-C4-alkyl .
.
1800iO1002 2 1 ~3~6 Furthermore preferably used as markers are carbonyl compounds of - the formula II where R3 is hydrogen, hydroxyl or Cl-C4-alkoxy, especially hydrogen or hydroxyl, and Ll and L2 are each hydrogen, and ring A is not benzo-fused.
Carbonyl compounds of the formula I where Rl is Cl-C4-alkyl or Cl-C4-alkoxy and R2 is Cl-C4-alkyl are particularly preferably used as markers.
10 The use of carbonyl compounds of the formula I where Rl and R2 are each, independently of one another, Cl-C4-alkyl, especially methyl, as markers is particularly important.
The carbonyl co.,.pounds of the formula I and/or II are used either 15 undiluted or in the form of solutions as markers for hydrocarbons. Suitable solvents are organic solvents. Preferably used are aromatic hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatic compounds which is commercially available under the name 20 Shellsol~ AB (from Shell). The concentration of carbonyl compound chosen is generally from 20 to 80% of the weight of the solution.
It is also possible to use other cosolvents, eg. alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, 25 pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol, glycols, such as butylethylene glycol or methylpropylene glycol, amines such as triethylamine, diisooctylamine, dicyclohexylamine, An;l;ne~ N-methylAn;l;ne~
N,N-dimethylAn;l;ne, toluidine or xylidine, alkanolamines such as 30 3-(2-methoxyethoxy)propylamine, o-cresol, m-cresol, p-cresol, ketones such as diethyl ketone or cyclohexanone, lactones such as ~-butyrolactone, carbonates such as ethylene carbonate or propylene carbonate, phenols such as t-butylphenol or nonylphenol, esters such as methyl phthalate, ethyl phthalate, 35 2-ethylhexyl phthalate, ethyl acetate, butyl acetate or cyclohexyl acetate, amides such as N,N-dimethylformamide, N,N-diethylacetamide or N-methylpyrrolidinone, or mixtures thereof.
40 The present invention further relates to hydrocarbons contA;n;ng one or more carbonyl cv.,.pounds of the formula I and/or II a markers.
The hydrocarbons preferably have a content of from 5 to 1000 ppm, - in particular 10 to 1000 ppm, of marker. A content of from 10 to 500 ppm, in particular 50 to 100 ppm, should be particularly emphasized in this context.
It is expedient in practice to tend to use larger amounts of marker so that testing of the marker-cont~;n;ng hydrocarbon gives a positive reaction in every case, especially in view of the possibility of the hydrocarbon being diluted in the case of 10 fraud.
Besides the carbonyl compounds of the formula I and/or II it is possible for the hydrocarbons also to contain other conventional markers or denaturing agents such as furfurol or C.I. Solvent 15 Red 198.
We have furthermore found that the carbonyl compounds of the abovementioned formulae I and/or II can advantageously be detected in hydrocarbons when the hydrocarbons are treated with a 20 solution of an iron(III) salt in aqueous alcohol or aqueous acetone.
Examples of suitable iron(III) salts are iron(III) halides such as iron(III) chloride or iron(III) bromide, iron(III) sulfate, 25 iron(III) nitrate or iron(III) acetate. The use of iron(III) chloride is preferred.
The iron(III) salts are used in solution in aqueous alcohol or aqueous acetone. The use of a solution in aqueous alcohol is 30 preferred.
Examples of suitable alcohols for preparing the solution in aqueous alcohol are methanol, ethanol, propanol or isopropanol.
The use of methanol or ethanol is preferred, and the use of 35 methanol should be particularly emphasized.
Suitable reagent solution~ generally have a content of from 0.05 to 0.5% by weight, preferably 0.1 to 0.3% by weight, of iron(III) salts, 10 to 90% by weight, preferably 40 to 70% by weight, of an 40 alcohol or acetone and 10 to 90~ by weight, preferably 30 to 60%
by weight, of water, in each case based on the weight of the reagent solution, the overall total of the ingredients being, of course, 100% by weight.
45 In the investigation of hydrocarbons which are in the liquid state of aggregation at standard temperature and pressure, the test is usually carried out by vigorously shaking about 20 ml of marker-cont~in;ng hydrocarbon with about 2 ml of regent solution for about 15 to 20 seconds.
The phases are then allowed to separate. In the presence of the 5 carbonyl compounds of the formula I and/or II the lower aqueous phase has a red or violet-brown color. The color depends on the nature of the marker.
The content of marker can moreover be determined by conventional lO methods, eg. spectroscopic methods.
In the investigation of hydrocarbons which are in the gaseous state of aggregation at standard temperature and pressure but have been liquified by compression, the test is usually carried 15 out by introducing from 1 to 2 ml of reagent solution into a suitable container, eg. a test tube, and then discharging the liquified hydrocarbon, and collecting it in the container, from a gas cylinder which contains the liquified hydrocarbon for about 15 to 30 seconds. It is advantageous in this case to allow the 20 hydrocarbon to escape from the horizontal cylinder because it is usually still in the liquid state of aggregation when it escapes.
The liquified hydrocarbon is then allowed to evaporate. In the presence of the carbonyl compounds of the formula I and/or II the reagent solution then has a red or violet-brown color.
The carbonyl compounds of the formula I or II to be used according to the invention have the advantageous profile of properties defined at the outset. They are easily available and very compatible with other additives which may be present in the 30 hydrocarbons requiring markers, eg. with auxiliaries or other markers or denaturing agents.
The following examples are intended to illustrate the invention in detail.
Example 1 Liquified gas (butane) in cylinders comprising acetylacetone in a concentration of 50 ppm as marker Butane was allowed to escape from the tap of the horizontal cylinder so that it escaped in liquid form. Then 20 ml of the hydrocarbon were mixed in a test tube with 2 ml of the following reagent:
2 1 ~38~6 0.1 g of iron(III) chloride dissolved in 20 ml of water and 80 ml of methanol 5 The liquified gas had completely evaporated after 20 sec, and the reagent had a red color.
Marker-contA;n;ng propane behaves in a similar way.
10 Example 2 (Comparative) Example 1 was carried out with liquified gas cont~;ning no markers. The reagent had a yellow color.
15 Example 3 Liquified propane in cylinders comprising salicylic acid in a concentration of 50 ppm as marker 20 The test described in Example 1 was repeated. The reagent had a distinct violet color.
Marker-cont~; n; ng butane behaves in a similar way.
25 Example 4 20 ml of diesel oil comprising 50 ppm of acetylacetone as marker were placed in a separating funnel. Then 2 ml of the reagent described in Example 1 were added and the mixture was vigorously 30 shaken for 20 sec. It was then allowed to settle. After 5 min, the phases separated. The lower aqueous phase had a distinct red color.
Example 5 1 ml of the marker-cont~;n;ng diesel oil from ~mpl e 4 was diluted with 9 ml of diesel oil cont~;n;ng no marker. The method described in Example 4 was repeated with this mixture. The lower aqueous phase had a pale red color.
Example 6 (Comparative) The method described in Example 4 was carried out with 20 ml of diesel oil cont~;n;ng no marker. The lower aqueous phase remained 45 yellow.
Example 7 20 ml of diesel oil comprising 50 ppm salicylic acid as marker were introduced into a separating funnel. Then 2 ml of the 5 reagent described in Example 1 were added and the mixture was vigorously shaken for 20 sec. It was then allowed to settle.
After 5 min, the phases separated. The lower aqueous phase had a distinct violet color.
10 The examples listed in the following table were carried out in a similar way.
Example Marker Hydrocarbon Concentration Reaction No. [ppm~ color 15 8 Acetylacetone Liquified gas 50 Red (butane) 9 Acetylacetone Liquified gas~) 30 Red (butane) Acetylacetone Lead-free 50 Red gasoline 11 Acetylacetone Super 50 Red gasoline~) 12 Acetylacetone Diesel oil 50 Red Acetylacetone Diesel oil 5 Pink 14 Methyl Liquified gas 50 Red acetoacetate Methyl Diesel oil 500 Red acetoacetate 16 Methyl Lead-free 500 Red acetoacetate gasoline 17 Ethyl Lead-free 500 Red -- acetoacetate gasoline 18 Ethyl Diesel oil 500 Red acetoacetate 35 19 Butyl - Lead-free 500 Red acetoacetate gasoline Butyl Diesel oil 500 Red acetoacetate 21 N-(3-methyl- Lead-free 100 Brown phenyl)aceto- gasoline acetamide 22 N-(3-methyl- Diesel oil 100 Brown phenyl)aceto-acetamide 45 23 Salicylic Liquified gas 50 Violet acid (butane) 2~ ~3886 . g Example Marker Hydrocarbon Concentration Reaction No. [ppm] color 24 Salicylic Super 50 Violet acid gasoline~) 5 25 Salicylic Diesel oil 50 Violet acid 26 Salicylic Lead-free 500 Violet acid gasoline 27 Salicyl- Diesel oil 100 Violet aldehyde ~) additionally contains 10 ppm furfurol ~) additionally contains 20 ppm C.I. Solvent Red 198,
Claims (8)
1. The use of carbonyl compounds of the formula R1-CO-CH2-CO-R2 (I) or , where R1 is hydrogen, C1-C4-alkyl, C1-C4-alkoxy or a radical of the formula , where X is a direct linkage, oxygen or imino, and Z1 and Z2 are each, independently of one another, hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen, R2 is hydrogen, C1-C4-alkyl or a radical of the formula , where X, Z1 and Z2 each have the abovementioned meanings, R3 is hydrogen, hydroxyl, C1-C4-alkyl or C1-C4-alkoxy and L1 and L2 are each, independently of one another hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy or halogen, and ring A can be benzo-fused, as markers for hydrocarbons.
2. The use of carbonyl compounds of the formula I as claimed in claim 1, wherein R1 is C1-C4-alkyl, C1-C4-alkoxy or a radical of the formula , where Z1 and Z2 each have the meanings stated in claim 1, and R2 is C1-C4-alkyl.
3. The use of carbonyl compounds of the formula II as claimed in claim 1, wherein R3 is hydrogen, hydroxyl or C1-4-alkoxy, and L1 and L2 are each hydrogen, and ring A is not benzo-fused.
4. The use of carbonyl compounds of the formula I as claimed in claim 1, wherein R1 is C1-C4-alkyl or C1-C4-alkoxy and R2 is C1-C4-alkyl.
5. The use of carbonyl compounds of the formula I as claimed in claim 1, wherein R1 and R2 are each, independently of one another, C1-C4-alkyl.
6. A hydrocarbon comprising one or more carbonyl compounds as claimed in claim 1 as markers.
7. A hydrocarbon comprising from 5 to 1000 ppm of one or more carbonyl compounds as claimed in claim 1 as markers.
8. A method for detecting carbonyl compounds of the formulae I
and/or II as claimed in claim 1 in hydrocarbons, which comprises treating the hydrocarbons with a solution of an iron(III) salt in aqueous alcohol or aqueous acetone.
and/or II as claimed in claim 1 in hydrocarbons, which comprises treating the hydrocarbons with a solution of an iron(III) salt in aqueous alcohol or aqueous acetone.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI941320A IT1269947B (en) | 1994-06-24 | 1994-06-24 | BRAND-DENATURING COMPOSITION PARTICULARLY SUITABLE FOR MARKING AND DENATURING FUELS |
ITMI94A001320 | 1994-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2193886A1 true CA2193886A1 (en) | 1996-01-04 |
Family
ID=11369163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA002193886A Abandoned CA2193886A1 (en) | 1994-06-24 | 1995-06-16 | Use of carbonyl compounds for marking hydrocarbons |
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EP (1) | EP0766724A1 (en) |
JP (1) | JPH10502111A (en) |
AU (1) | AU2792895A (en) |
BR (1) | BR9508104A (en) |
CA (1) | CA2193886A1 (en) |
CO (1) | CO4410389A1 (en) |
CZ (1) | CZ379296A3 (en) |
HU (1) | HUT76753A (en) |
IL (1) | IL114195A0 (en) |
IT (1) | IT1269947B (en) |
MX (1) | MX9700119A (en) |
NO (1) | NO965554L (en) |
PL (1) | PL317941A1 (en) |
WO (1) | WO1996000271A1 (en) |
Cited By (1)
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EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
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FR2787577B1 (en) | 1998-12-16 | 2001-03-02 | Total Raffinage Distrib | COLORED INDICATOR FOR MEASURING THE DISTRIBUTION OF HYDROCARBON FAMILIES CONTAINED IN A MIXTURE, METHOD FOR OBTAINING SAME AND USES THEREOF |
FR2971254B1 (en) * | 2011-02-08 | 2014-05-30 | Total Raffinage Marketing | LIQUID COMPOSITIONS FOR MARKING LIQUID HYDROCARBON FUELS AND FUELS, FUELS AND FUELS CONTAINING THEM, AND METHOD OF DETECTING MARKERS |
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GB287192A (en) * | 1926-10-25 | 1928-03-22 | British Dyestuffs Corp Ltd | Improvements in and relating to fuels for internal combustion engines |
GB473653A (en) * | 1936-04-15 | 1937-10-15 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of carbon compounds of high molecularweight |
US2205408A (en) * | 1938-08-09 | 1940-06-25 | Gen Aniline & Film Corp | Fluorescent hydrocarbon oil |
US3508875A (en) * | 1967-10-03 | 1970-04-28 | Union Oil Co | Method for tracing the flow of water in subterranean formations |
NL7103060A (en) * | 1970-03-11 | 1971-09-14 | ||
IT1222752B (en) * | 1987-09-28 | 1990-09-12 | Acna Chimica Organica | METHOD OF MARKING PETROLEUM PRODUCTS AND ORGANIC SOLVENTS |
GB8802237D0 (en) * | 1988-02-02 | 1988-03-02 | Shell Int Research | Detection of chemicals by immunoassay |
FR2650606B1 (en) * | 1989-08-07 | 1992-04-30 | Aussedat Rey | INFALSIFIABLE SECURITY PAPER AND AQUEOUS OR ORGANIC COMPOSITION USEFUL, IN PARTICULAR FOR MAKING PAPER INFALSIFIABLE |
JPH048798A (en) * | 1990-04-26 | 1992-01-13 | Yoshibi:Kk | Liquefied gas fuel for generating high-luminance colored flame |
IT1254456B (en) * | 1992-02-14 | 1995-09-25 | Basf Italia | BRAND-DENATURING COMPOSITION PARTICULARLY SUITABLE FOR MARKING AND ENENATURING COMBUSTIBLE BITUMES OR RELATED PRODUCTS. |
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1994
- 1994-06-24 IT ITMI941320A patent/IT1269947B/en active IP Right Grant
-
1995
- 1995-06-16 PL PL95317941A patent/PL317941A1/en unknown
- 1995-06-16 CA CA002193886A patent/CA2193886A1/en not_active Abandoned
- 1995-06-16 AU AU27928/95A patent/AU2792895A/en not_active Abandoned
- 1995-06-16 BR BR9508104A patent/BR9508104A/en not_active Application Discontinuation
- 1995-06-16 EP EP95923333A patent/EP0766724A1/en not_active Withdrawn
- 1995-06-16 WO PCT/EP1995/002330 patent/WO1996000271A1/en not_active Application Discontinuation
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2738154A1 (en) * | 2012-11-30 | 2014-06-04 | Inter-Euro Technology Limited | Improved fuel markers |
WO2014083186A2 (en) * | 2012-11-30 | 2014-06-05 | Inter-Euro Technology Limited | Improved fuel markers |
WO2014083186A3 (en) * | 2012-11-30 | 2014-09-12 | Inter-Euro Technology Limited | Improved fuel markers |
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IL114195A0 (en) | 1995-10-31 |
CO4410389A1 (en) | 1997-01-09 |
AU2792895A (en) | 1996-01-19 |
CZ379296A3 (en) | 1997-06-11 |
ITMI941320A1 (en) | 1995-12-24 |
WO1996000271A1 (en) | 1996-01-04 |
NO965554D0 (en) | 1996-12-23 |
BR9508104A (en) | 1997-08-12 |
NO965554L (en) | 1997-02-18 |
MX9700119A (en) | 1997-04-30 |
EP0766724A1 (en) | 1997-04-09 |
JPH10502111A (en) | 1998-02-24 |
HU9603550D0 (en) | 1997-02-28 |
PL317941A1 (en) | 1997-05-12 |
ITMI941320A0 (en) | 1994-06-24 |
HUT76753A (en) | 1997-11-28 |
IT1269947B (en) | 1997-04-16 |
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