JP2018127503A - A high-octane-number gasoline composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a high-octane-number gasoline composition that can be prepared at low cost and is environmentally friendly.SOLUTION: The gasoline composition according to the present invention comprises: at least one selected from a group consisting of ketone having 3 to 10 carbon atoms and aldehyde having 3 to 10 carbon atoms, and a gasoline base material, wherein a content of the ketone having 3 to 10 carbon atoms is 0.1 wt.% or more based on a total amount of the composition, or the content of the aldehyde having 3 to 10 carbon atoms is 0.5 wt.% or more based on the total amount of the composition.SELECTED DRAWING: None

Description

  The present invention relates to high octane gasoline compositions.

  Due to the recent increase in energy problems and environmental problems, there has been a demand for the creation of fuels having good fuel consumption characteristics and less exhaust gas. For example, for the purpose of improving fuel economy characteristics of regular gasoline and the like, a method of adding a specific additive to form a gasoline composition is known. Examples of the additive include aromatic hydrocarbons, oxygenated compounds, amines , Branched paraffins and olefins are widely known. For example, a high-octane fuel having a research octane number (hereinafter sometimes referred to as RON) of about 100 can be prepared by adding these additives to regular gasoline.

  As specific examples of additives, ethyl tertiary butyl ether (see Patent Document 1), ethanol (see Patent Document 2), amine compounds and carboxylic acids (see Patent Document 3) are known.

JP 2004-285205 A JP 2004-238575 A JP 2005-132973 A

  However, conventional additives are expensive, and depending on the type of additive used, exhaust gases (for example, carbon monoxide, SOx, NOx, etc.) that adversely affect the environment may be generated. Further, since it is difficult to say that the fuel efficiency characteristics of a gasoline composition containing the additive are sufficient, creation of a more useful gasoline composition is required.

  This invention is made | formed in view of the said prior art, The objective is to obtain the high octane number gasoline composition which can be prepared at low cost and is environmentally friendly.

  The present inventor has found that a gasoline composition having a low octane number and a high octane number can be obtained by containing a specific component in a gasoline base material. Moreover, it discovered that the gasoline composition of a high octane number could be easily prepared at low cost by oxidizing a gasoline base material on specific conditions.

That is, the present invention relates to the following.
[1] A gasoline composition containing at least one selected from the group consisting of a ketone having 3 to 10 carbon atoms and an aldehyde having 3 to 10 carbon atoms, and a gasoline base material,
The content of the ketone having 3 to 10 carbon atoms is 0.1% by weight or more based on the total amount of the composition, or the content of the aldehyde having 3 to 10 carbon atoms is 0.1% relative to the total amount of the composition. A gasoline composition that is 5% by weight or more.
[2] The ketone having 3 to 10 carbon atoms is acetone, 2-heptanone, 3-heptanone, 4-heptanone, or 2,3-heptanedione,
The gasoline composition according to [1], wherein the aldehyde having 3 to 10 carbon atoms is heptanal, 2,2-dimethyl-1-propanal, or benzaldehyde.
[3] The gasoline composition according to [1] or [2], further comprising an alcohol having 3 to 10 carbon atoms.
[4] The alcohol having 3 to 10 carbon atoms is 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 1,2-heptanediol, 1,7-heptanediol, 2,2-dimethyl-1- The gasoline composition according to [3], which is propanol, 2,4,4-trimethyl-2-pentanol, or benzyl alcohol.
[5] The gasoline composition according to any one of [1] to [4], further containing a carboxylic acid having 3 to 10 carbon atoms.
[6] The gasoline composition according to [5], wherein the carboxylic acid having 3 to 10 carbon atoms is 2,2-dimethyl-1-propanoic acid, heptanoic acid, heptanedioic acid or benzoic acid.
[7] The gasoline composition according to any one of [1] to [6], wherein the research octane number in the spray ignition test is 89 or more.

  The gasoline composition of the present invention can be prepared at a low cost, and a gasoline composition having high fuel efficiency (high octane number) can be obtained. Further, when the obtained gasoline composition is used as fuel, it is environmentally friendly because it does not emit SOx and NOx, and the CO content in the exhaust gas is small. Furthermore, the gasoline composition of the present invention can also be obtained by oxidizing a gasoline base material under specific conditions. In this case, the gasoline composition can be prepared easily and at low cost. Furthermore, since the gasoline composition of the present invention can be prepared in the vehicle by providing the oxidation reaction device in the vehicle, a tank for storing the additive in the engine room is not required.

In Examples 1-5, it is a correlation diagram of the research octane number of the reaction liquid, and the conversion rate of a raw material. It is a correlation diagram of the research octane number of the reaction liquid in Examples 1-5, and the content rate of the alcohol component in a gasoline composition. It is a correlation diagram of the research octane number of the reaction liquid in Examples 1-5, and the content rate of the ketone component in a gasoline composition. It is a correlation diagram of the research octane number of the reaction liquid in Examples 1-5, and the oxygen content rate in a gasoline composition.

<Gasoline composition>
The gasoline composition of the present invention contains at least one selected from the group consisting of a specific amount of a ketone having 3 to 10 carbon atoms and an aldehyde having 3 to 10 carbon atoms and a gasoline base material as essential components. Features. Moreover, as a component other than the above, an alcohol having 3 to 10 carbon atoms or a carboxylic acid having 3 to 10 carbon atoms may be further included.

  In addition, especially the gasoline composition of this invention will contain at least 1 chosen from the group which consists of a C3-C10 ketone and a C3-C10 aldehyde as components other than a gasoline base material. Although it does not restrict | limit, it is preferable that a C3-C10 ketone and a C3-C10 aldehyde are included from a viewpoint of the fuel consumption characteristic of the gasoline composition obtained. Furthermore, it is more preferable that a C3-C10 ketone, a C3-C10 aldehyde, and a C3-C10 alcohol are included, a C3-C10 ketone, a C3-C10 aldehyde, carbon Most preferably, it contains an alcohol having 3 to 10 carbon atoms and a carboxylic acid having 3 to 10 carbon atoms.

[Gasoline substrate]
The gasoline base used in the present invention is usually a petroleum fraction obtained by subjecting crude oil to various refining treatments. For example, light naphtha or heavy naphtha obtained by atmospheric distillation of crude oil, the light naphtha Desulfurized light naphtha and desulfurized heavy naphtha obtained by desulfurizing and heavy naphtha, cracked gasoline obtained by catalytic cracking and hydrocracking, light cracked gasoline obtained by distilling the cracked gasoline and heavy By adding lower olefins to hydrocarbons such as cracked gasoline, fractions obtained by removing benzene in reformed gasoline obtained by catalytic reforming (debenzene reformed gasoline), polymerized gasoline obtained by olefin polymerization, and isobutane Obtained alkylate, isomerate (isomerized gasoline) obtained by isomerization of linear lower paraffinic hydrocarbon, de-N-paraffin oil, Beauty like fractions and aromatic hydrocarbons of these specific ranges and the like. As the gasoline base material in the gasoline composition of the present invention, these various gasoline base materials may be used alone. However, in order to satisfy various performances, a gasoline base material obtained by combining a plurality of gasoline base materials is usually used.

  Although the component of a gasoline base material is not specifically limited, For example, a C3-C10 hydrocarbon is mentioned. More specifically, as a component contained in the gasoline base, for example, a linear or branched aliphatic hydrocarbon having 3 to 10 carbon atoms, an alicyclic hydrocarbon having 3 to 10 carbon atoms, and a carbon number 6-10 aromatic hydrocarbons etc. are mentioned.

  Examples of the linear or branched aliphatic hydrocarbon having 3 to 10 carbon atoms include linear alkanes having 3 to 10 carbon atoms such as propane, butane, pentane, hexane, heptane, octane, nonane and decane; 2-methylpropane, 2-methylbutane, 2,2-dimethylpropane, 2-methylpentane, 3-methylpentane, 2,3-dimethylbutane, 2-methylhexane, 3-methylhexane, 3,4-dimethylhexane, C3-C10 branched alkane such as 3-methyloctane and 2,2,4-trimethylpentane; propylene, isobutylene, 1-pentene, 1-hexene, 2-hexene, 1-heptene, 1-octene, C3-C10 linear or branched alkenes such as 1-decene, 1-dodecene, 1-tetradecene, 1,4-hexadiene Clause and the like alkadiene.

  Examples of the alicyclic hydrocarbon having 3 to 10 carbon atoms include cycloalkanes having 3 to 10 carbon atoms such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, and cyclodecane; cyclopropene, cyclobutene , Cycloalkene having 3 to 10 carbon atoms such as cyclopentene, cyclooctene, cyclohexene, cycloheptene and cyclododecaene; cyclohexane having 3 to 10 carbon atoms such as cyclopentadiene, 1,3-cyclohexadiene and 1,5-cyclooctadiene Examples include alkadienes.

  Examples of the aromatic hydrocarbon having 6 to 10 carbon atoms include benzene, toluene, o-xylene, m-xylene, p-xylene, naphthalene and the like.

[C3-C10 ketone]
The ketone in the gasoline composition of the present invention is not particularly limited as long as it has 3 to 10 carbon atoms, but preferably has 1 to 6 carbonyl groups in the ketone molecule, more preferably 1 to 3 carbon atoms. It is.

  Examples of the ketone include a linear ketone having 3 to 10 carbon atoms, a branched ketone having 3 to 10 carbon atoms, an alicyclic ketone having 3 to 10 carbon atoms, and an aromatic ketone having 7 to 10 carbon atoms. It is done. The gasoline composition of the present invention may contain one of these ketones alone or two or more.

  The linear ketone having 3 to 10 carbon atoms is not particularly limited as long as at least one carbon atom of the linear hydrocarbon is substituted with a carbonyl group. For example, acetone, methyl ethyl ketone, 2-pentanone, C3-C10 linear having one carbonyl group such as 2-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, nonan-2-one and positional isomers of the carbonyl group Ketone; C3-C10 linear ketones having two carbonyl groups such as 2,3-heptanedione and acetylacetone. The branched chain ketone having 3 to 10 carbon atoms is not particularly limited as long as it is a ketone in which at least one carbon atom of the branched chain hydrocarbon is substituted with a carbonyl group, but 2,2-dimethyl-1-propanone, Examples include 2,5-hexanedione, 2,3-heptanedione, and positional isomers of the carbonyl group (for example, 3-heptanone). The alicyclic ketone having 3 to 10 carbon atoms is not particularly limited as long as it is a ketone in which at least one carbon atom of the alicyclic hydrocarbon is substituted with a carbonyl group. For example, cyclobutanone, cyclopentanone, cyclohexanone, Examples include cycloheptanone, cyclooctanone, and positional isomers of the carbonyl group.

  In addition, as a C3-C10 ketone contained in the gasoline composition of this invention, it is acetone, 2-heptanone, 3-heptanone, 4-heptanone, or 2,3-heptanedione from a viewpoint of the improvement of a fuel consumption. Is more preferable, acetone or 2-heptanone is more preferable, and 2-heptanone is still more preferable. That is, as a C3-C10 ketone, from a viewpoint of the improvement of a fuel consumption, a C3-C10 linear ketone or a C3-C10 branched chain ketone is preferable, More preferably, it is C3-C3. -10 linear ketones.

[Aldehyde having 3 to 10 carbon atoms]
The aldehyde in the gasoline composition of the present invention is not particularly limited as long as it is an aldehyde having 3 to 10 carbon atoms. For example, a linear aldehyde having 3 to 10 carbon atoms, a branched aldehyde having 3 to 10 carbon atoms, and a carbon number. 7-10 aromatic aldehydes are mentioned. The gasoline composition of the present invention may contain one of these aldehydes alone or may contain two or more.

  The straight-chain aldehyde having 3 to 10 carbon atoms is not particularly limited as long as the carbon atom at the terminal of the straight-chain hydrocarbon is substituted with a carbonyl group. For example, butanal, pentanal, hexanal, heptanal, octanal And nonanal. The branched aldehyde having 3 to 10 carbon atoms is not particularly limited as long as the terminal carbon atom of the branched hydrocarbon is substituted with a carbonyl group. For example, 2,2-dimethyl-1-propanal (Pivalaldehyde), 2,4,4-trimethyl-2-pentanal and the like. The aromatic aldehyde is not particularly limited as long as it is an aldehyde in which the carbon atom at the terminal of the hydrocarbon having an aromatic hydrocarbon group is substituted with a carbonyl group, and examples thereof include benzaldehyde.

  The aldehyde having 3 to 10 carbon atoms in the gasoline composition of the present invention is preferably heptanal, 2,2-dimethyl-1-propanal, or benzaldehyde, more preferably benzaldehyde, from the viewpoint of improving fuel consumption. That is, as an aldehyde having 3 to 10 carbon atoms, from the viewpoint of improving fuel efficiency, a linear aldehyde having 3 to 10 carbon atoms, a branched aldehyde having 3 to 10 carbon atoms, or an aromatic group having 7 to 10 carbon atoms. Aldehydes are preferable, and aromatic aldehydes having 7 to 10 carbon atoms are more preferable.

[C3-C10 alcohol]
The alcohol in the gasoline composition of the present invention is not particularly limited as long as it is an alcohol having 3 to 10 carbon atoms, but the number of hydroxyl groups in the alcohol molecule is preferably 1 to 6, and more preferably 1 to 3 It is a piece.

  Examples of the alcohol having 3 to 10 carbon atoms include linear or branched alcohol having 3 to 10 carbon atoms, alicyclic alcohol having 3 to 10 carbon atoms, and aromatic alcohol having 6 to 10 carbon atoms. . The gasoline composition of the present invention may contain one of these alcohols alone or two or more.

  The linear alcohol having 3 to 10 carbon atoms is not particularly limited as long as it is an alcohol in which at least one hydrogen atom of the linear hydrocarbon is substituted with a hydroxyl group. For example, 1-propanol, 1-butanol, 1 -Pentanol, 1-hexanol, 1-heptanol, 1-octanol and positional isomers of hydroxyl groups thereof (for example, 2-propanol, 2-butanol, 2-pentanol, 3-pentanol, 2-hexanol, 3-hexanol) , 2-heptanol, 3-heptanol, 4-heptanol, 2-octanol, 3-octanol), etc., a straight-chain alcohol having 3 to 10 carbon atoms; 1,2-propanediol, 1,3- Propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-pentanediol, 1 5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, 1,2-heptanediol, 1,7-heptanediol, 1,2-octanediol, 1,8-octanediol and its hydroxyl group C3-C10 linear alcohol etc. which have two hydroxyl groups, such as a positional isomer, are mentioned. The branched chain alcohol having 3 to 10 carbon atoms is not particularly limited as long as it is an alcohol in which at least one hydrogen atom of the branched chain hydrocarbon is substituted with a hydroxyl group. For example, isobutyl alcohol, 2,2-dimethyl-1 -Propanol, 2,4,4-trimethyl-2-pentanol and positional isomers of the hydroxyl group (for example, tertiary butyl alcohol, 2-ethylhexanol) and the like. The alicyclic alcohol having 3 to 10 carbon atoms is not particularly limited as long as it is an alcohol in which at least one hydrogen atom of the alicyclic hydrocarbon is substituted with a hydroxyl group. For example, cyclopropanol, cyclobutanol, cyclopentanol , Cyclohexanol, cycloheptanol, cyclooctanol and the positional isomers of the hydroxyl group thereof. The aromatic alcohol having 6 to 10 carbon atoms is not particularly limited as long as it is an alcohol in which at least one hydrogen atom of an aromatic hydrocarbon is substituted with a hydroxyl group. For example, it relates to phenol, benzyl alcohol, salicyl alcohol and the hydroxyl group thereof. And positional isomers.

  In addition, as a C3-C10 alcohol in the gasoline composition of this invention, from a viewpoint of the improvement of a fuel consumption, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 1,2-heptanediol, 1 , 7-heptanediol, 2,2-dimethyl-1-propanol, 2,4,4-trimethyl-2-pentanol, or benzyl alcohol, more preferably 1-heptanol, 2-heptanol, 2 , 2-dimethyl-1-propanol, 2,4,4-trimethyl-2-pentanol, or benzyl alcohol, more preferably 2,2-dimethyl-1-propanol, 2,4,4-trimethyl- 2-pentanol or benzyl alcohol, most preferably benzyl alcohol. That is, as an alcohol having 3 to 10 carbon atoms, from the viewpoint of improving fuel efficiency, a linear alcohol having 3 to 10 carbon atoms, a branched alcohol having 3 to 10 carbon atoms, or an aromatic having 6 to 10 carbon atoms. Alcohol is preferable, more preferably a branched chain alcohol having 3 to 10 carbon atoms, or an aromatic alcohol having 6 to 10 carbon atoms, and further preferably an aromatic alcohol having 6 to 10 carbon atoms.

[Carboxylic acid having 3 to 10 carbon atoms]
The carboxylic acid in the gasoline composition of the present invention is not particularly limited as long as it is a carboxylic acid having 3 to 10 carbon atoms. For example, a linear carboxylic acid having 3 to 10 carbon atoms or a branched chain carboxylic acid having 3 to 10 carbon atoms. Examples thereof include acids and aromatic carboxylic acids having 7 to 10 carbon atoms. The gasoline composition of the present invention may contain one of these carboxylic acids alone or may contain two or more.

  The linear carboxylic acid having 3 to 10 carbon atoms is not particularly limited as long as it is a carboxylic acid in which the terminal carbon atom of the linear hydrocarbon is substituted with a carboxyl group. For example, butanoic acid, pentanoic acid, hexane Examples thereof include linear monocarboxylic acids having 3 to 10 carbon atoms such as acid, heptanoic acid and octanoic acid, and linear dicarboxylic acids having 3 to 10 carbon atoms such as heptanedioic acid. The branched chain carboxylic acid having 3 to 10 carbon atoms is not particularly limited as long as the terminal carbon atom of the branched hydrocarbon is substituted with a carboxyl group. For example, 2,2-dimethyl-1- Examples include propanoic acid (pivalic acid) and isooctanoic acid. The aromatic carboxylic acid is not particularly limited as long as it is a carboxylic acid in which the carbon atom at the terminal of the hydrocarbon having an aromatic hydrocarbon group is substituted with a carboxyl group, and examples thereof include benzoic acid and phthalic acid.

  The carboxylic acid having 3 to 10 carbon atoms in the gasoline composition of the present invention is 2,2-dimethyl-1-propanoic acid, heptanoic acid, heptanedioic acid or benzoic acid from the viewpoint of improving fuel efficiency. Is preferred, and benzoic acid is more preferred. That is, the carboxylic acid having 3 to 10 carbon atoms is preferably a branched carboxylic acid having 3 to 10 carbon atoms or an aromatic carboxylic acid having 7 to 10 carbon atoms, more preferably carbon number from the viewpoint of improving fuel efficiency. 7-10 aromatic carboxylic acids.

[Other oxygen-containing hydrocarbons]
In the gasoline composition of the present invention, an oxygen-containing hydrocarbon other than an alcohol having 3 to 10 carbon atoms, a ketone having 3 to 10 carbon atoms, an aldehyde having 3 to 10 carbon atoms, and a carboxylic acid having 3 to 10 carbon atoms (hereinafter, (Referred to as “other oxygenated hydrocarbons”). In the present invention, “oxygen-containing hydrocarbon” refers to a compound obtained by oxidizing a hydrocarbon (for example, alcohol, ketone, aldehyde, carboxylic acid, etc.). Examples of other oxygen-containing hydrocarbons include alcohols having 11 or more carbon atoms, aldehydes having 11 or more carbon atoms, carboxylic acids having 11 or more carbon atoms, and ethers.

  In the gasoline composition of the present invention, an alcohol having 3 to 10 carbon atoms, a ketone having 3 to 10 carbon atoms, an aldehyde having 3 to 10 carbon atoms, a carboxylic acid having 3 to 10 carbon atoms, and other oxygen-containing hydrocarbons (hereinafter, (Referred to as “alcohols having 3 to 10 carbon atoms”) may be obtained by oxidizing hydrocarbons in the gasoline base material. In this case, it is preferable that the hydrocarbon is obtained by reacting hydrocarbons in the gasoline base material under specific oxidation conditions described later. Since the alcohol having 3 to 10 carbon atoms is obtained by oxidizing a gasoline base material, when a gasoline composition is used as a fuel, it does not emit SOx or NOx, and contains CO in exhaust gas. Since the amount is small, it does not adversely affect the environment, and the fuel consumption characteristics of the gasoline composition are further improved. Further, when the alcohol having 3 to 10 carbon atoms is obtained by reacting hydrocarbons in a gasoline base material under specific oxidation conditions, the fuel efficiency characteristics of the gasoline composition are further improved.

[Additive]
Various additives can be appropriately blended in the gasoline composition of the present invention as necessary. Such additives include metal deactivators such as Schiff compounds and thioamide compounds, lubricity improvers such as fatty acids and fatty acid esters, surface ignition inhibitors such as organophosphorus compounds, succinimides, polyalkylamines , Detergents such as polyetheramines, anti-icing agents, alkali metals and alkaline earth metal salts of organic acids, sulfuric acid esters of higher alcohols, anionic surfactants, cationic surfactants, double-sided surfactants, etc. Known anti-static agents, rust inhibitors such as alkenyl succinic acid esters, identification agents such as kilyzanine and coumarin, odorants such as natural essential oils and synthetic fragrances, and coloring agents such as azo dyes. These additives can be added singly or in combination of two or more.

  In the gasoline composition of the present invention, the content (total amount) of an alcohol having 3 to 10 carbon atoms, a ketone having 3 to 10 carbon atoms, and an aldehyde having 3 to 10 carbon atoms is not particularly limited. It is preferable that it is 1 weight% or more (for example, 1-80 weight%) with respect to it, More preferably, it is 5-60 weight%, Most preferably, it is 10-50 weight%. By setting it as the said structure, the research octane number of a gasoline composition improves.

  Moreover, although content of C3-C10 alcohol is not specifically limited, For example, it is preferable that it is 1 weight% or more (for example, 1-80 weight%) with respect to the composition whole quantity, More preferably, it is 1-50. % By weight, most preferably 1-30% by weight. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves.

  Further, the content of the ketone having 3 to 10 carbon atoms is not particularly limited, but for example, it is preferably 0.1% by weight or more (for example, 0.1 to 50% by weight), more preferably based on the total amount of the composition. Is 0.1 to 20% by weight, most preferably 0.5 to 15% by weight. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves.

  Further, the content of the aldehyde having 3 to 10 carbon atoms is not particularly limited, but is preferably 0.5% by weight or more (for example, 0.5 to 30% by weight), more preferably, based on the total amount of the composition. Is 1 to 20% by weight, most preferably 1 to 10% by weight. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves.

  When the gasoline composition of the present invention contains a carboxylic acid having 3 to 10 carbon atoms, the content thereof is not particularly limited. %), More preferably 1 to 25% by weight, and most preferably 2 to 20% by weight. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves.

  In the gasoline composition of the present invention, the gasoline base content is preferably 20 to 99% by weight, more preferably 40 to 95% by weight, and most preferably 50 to 90% by weight, based on the total amount of the composition. It is. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves.

  In the gasoline composition of the present invention, when “other oxygenated hydrocarbons” are contained, the content is not particularly limited, but for example, 20% by weight or less (for example, 0.01 to 20% by weight) based on the total amount of the composition It is preferably 10% by weight or less (0.1 to 10% by weight), and most preferably 5% by weight or less (1 to 5% by weight). By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves.

  The research octane number of the gasoline composition of the present invention is preferably 89 or more, more preferably 94 or more, still more preferably 98 or more, and most preferably 104 or more. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves. In the present invention, the research octane number is calculated by a spray ignition test.

  The oxygen-containing hydrocarbon content (content) of the gasoline composition of the present invention is not particularly limited, but is preferably, for example, 1% by weight or more (for example, 1 to 80% by weight) based on the total amount of the composition, Preferably it is 5-60 weight%, Most preferably, it is 10-50 weight%. By setting it as the said structure, RON of a gasoline composition improves.

  Although the oxygen content rate of the gasoline composition of the present invention is not particularly limited, for example, it is preferably 0.1% by weight or more (0.1 to 20% by weight) with respect to the total amount of the composition, more preferably 0.00. 05 to 10% by weight, more preferably 1 to 10% by weight. By setting it as the said structure, the fuel consumption characteristic of a gasoline composition improves. The “oxygen content” of the gasoline composition means the weight ratio of oxygen atoms (total amount) of components (for example, oxygen-containing hydrocarbons) contained in the gasoline composition to the gasoline composition (total amount).

<Method for producing gasoline composition>
The gasoline composition of the present invention comprises at least one selected from the group consisting of a gasoline base, a specific amount of a ketone having 3 to 10 carbon atoms, and an aldehyde having 3 to 10 carbon atoms, and optionally 3 carbon atoms. -10 alcohol, carboxylic acid having 3 to 10 carbon atoms, other oxygen-containing hydrocarbons, and the like. Moreover, it is good also as a gasoline composition by oxidizing the hydrocarbon in a gasoline base material. In addition, when preparing the gasoline composition of this invention by oxidizing the hydrocarbon in a gasoline base material, it is good also as a gasoline composition of this invention by oxidizing a gasoline base material in coexistence of oxygen and ozone. Furthermore, it is good also as a gasoline base material of this invention by mix | blending the gasoline base material oxidized on said conditions with the gasoline base material.

  Below, the method of preparing (manufacturing) the gasoline composition of this invention by oxidizing the hydrocarbon in a gasoline base material is demonstrated. In addition, as a method of preparing (manufacturing) the gasoline composition of the present invention, a method of oxidizing a gasoline base material in the presence of oxygen and ozone can be mentioned.

[Oxygen and ozone]
When preparing a gasoline composition by oxidizing a gasoline base material, it is preferable to carry out an oxidation reaction in the presence of oxygen and ozone. That is, the gasoline composition of the present invention may be obtained by oxidizing hydrocarbons in a gasoline base material in the presence of oxygen and ozone or in the circulation of oxygen gas and ozone gas. By using oxygen as an oxidizing agent together with ozone, it is possible to promote the extraction of hydrogen from the hydrocarbons in the gasoline base material, and to activate the radical reaction. Therefore, even under mild conditions (reaction pressure: normal pressure, reaction temperature: about room temperature to 200 ° C., preferably 50 to 150 ° C., particularly preferably 60 to 120 ° C.), the oxidation reaction can be promoted. When the reaction is performed under the flow of oxygen gas and ozone gas, the amount of ozone gas in the ozone gas-containing oxygen gas is, for example, about 0.1 to 10% by volume of oxygen gas from the viewpoint of reactivity and economy.

  As oxygen, it is preferable to use molecular oxygen. As molecular oxygen, pure oxygen may be used, and oxygen diluted with an inert gas such as nitrogen, helium, argon, carbon dioxide, or air at normal pressure or pressure (1 to 100 atm) is used. May be.

  The ozone has a function as a radical generator. It is preferable to use ozone gas as ozone. Further, the ozone gas may be supplied intermittently or continuously as long as the reaction proceeds smoothly.

  The radical generator is a compound that generates radicals under mild reaction conditions (for example, heating, light irradiation, etc.). In the present invention, as a radical generator other than ozone, an imide compound having the following cyclic imide skeleton and other radical generators may be used.

[Imide compound having a cyclic imide skeleton]
In the present invention, when a gasoline composition is prepared by oxidizing a gasoline base material, an imide compound having a cyclic imide skeleton may be used as a radical generator in order to further accelerate the oxidation reaction.

  As the imide compound having a cyclic imide skeleton, imide compounds having various known cyclic imide skeletons can be used as an oxidation catalyst. Examples of the imide compound having a cyclic imide skeleton include a cyclic imide skeleton represented by the following formula (I).

  In the formula (I), the bond between the nitrogen atom and X is a single bond or a double bond. The imide compound may have a plurality of cyclic imide skeletons represented by the formula (I) in the molecule. In the imide compound, when X is an —OR group and R is a protecting group for a hydroxyl group, a portion of the cyclic imide skeleton excluding R (N-oxy cyclic imide skeleton) It may be bonded via.

Examples of the protecting group for the hydroxyl group represented by R include an alkyl group (for example, C _1-4 alkyl group such as methyl and t-butyl group), an alkenyl group (for example, allyl group), a cycloalkyl group, and the like. (For example, cyclohexyl group, etc.), aryl group (for example, 2,4-dinitrophenyl group, etc.), aralkyl group (for example, benzyl, 2,6-dichlorobenzyl, 3-bromobenzyl, 2-nitrobenzyl, triphenylmethyl) A substituted methyl group (for example, methoxymethyl, methylthiomethyl, benzyloxymethyl, t-butoxymethyl, 2-methoxyethoxymethyl, 2,2,2-trichloroethoxymethyl, bis (2-chloroethoxy) methyl, 2- (trimethylsilyl) ethoxymethyl group, etc.), substituted ethyl groups (for example, 1-ethoxyethyl, 1-methyl-1-methoxyethyl, 1-isopropoxyethyl, 2,2,2-trichloroethyl, 2-methoxyethyl group, etc.), tetrahydropyranyl group, tetrahydrofuranyl group, 1-hydroxyalkyl group etc. (for example, A group capable of forming an acetal or hemiacetal with a hydroxyl group of 1-hydroxyethyl, 1-hydroxyhexyl, 1-hydroxydecyl, 1-hydroxyhexadecyl, 1-hydroxy-1-phenylmethyl group, etc .; an acyl group (for example, Aliphatic saturated or not such as C _1-20 aliphatic acyl group such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, pivaloyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl group, etc. Saturated reed Group: acetoacetyl group; alicyclic acyl group such as cycloalkanecarbonyl group such as cyclopentanecarbonyl, cyclohexanecarbonyl group; aromatic acyl group such as benzoyl, naphthoyl group, etc .; sulfonyl group (methanesulfonyl, ethanesulfonyl, trifluoro) Lomethanesulfonyl, benzenesulfonyl, p-toluenesulfonyl, naphthalenesulfonyl groups, etc.), alkoxycarbonyl groups (eg, C _1-4 alkoxy-carbonyl groups such as methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl groups, etc.), aralkyloxycarbonyl Group (for example, benzyloxycarbonyl group, p-methoxybenzyloxycarbonyl group, etc.), substituted or unsubstituted carbamoyl group (for example, carbamoyl, methylcarbamoyl, phenylcarbamoyl group, etc.) A group obtained by removing an OH group from an inorganic acid (for example, sulfuric acid, nitric acid, phosphoric acid, boric acid, etc.), a dialkylphosphinothioyl group (for example, a dimethylphosphinothioyl group), a diarylphosphinothioyl group ( For example, diphenylphosphinothioyl group etc.), substituted silyl groups (for example, trimethylsilyl, t-butyldimethylsilyl, tribenzylsilyl, triphenylsilyl group etc.) are mentioned.

  In the case where X is an —OR group, R in the case where a plurality of portions (N-oxycyclic imide skeleton) excluding R are bonded via R in the cyclic imide skeleton includes, for example, oxalyl, malonyl Polycarboxylic acid acyl groups such as succinyl, glutaryl, adipoyl, phthaloyl, isophthaloyl, terephthaloyl groups; carbonyl groups; polyvalent hydrocarbon groups such as methylene, ethylidene, isopropylidene, cyclopentylidene, cyclohexylidene, benzylidene groups ( In particular, a group that forms an acetal with two hydroxyl groups).

  Preferred R includes, for example, a hydrogen atom; a group capable of forming an acetal or hemiacetal with a hydroxyl group; an OH group removed from an acid such as carboxylic acid, sulfonic acid, carbonic acid, carbamic acid, sulfuric acid, phosphoric acid, boric acid, etc. Hydrolyzable protecting groups that can be removed by hydrolysis of groups (acyl group, sulfonyl group, alkoxycarbonyl group, carbamoyl group, etc.) and the like are included.

  In the formula (I), n represents 0 or 1. That is, Formula (I) represents a 5-membered cyclic imide skeleton when n is 0, and represents a 6-membered cyclic imide skeleton when n is 1.

A typical example of the imide compound is an imide compound represented by the following formula (1). In the formula (1), n represents 0 or 1. X represents an oxygen atom or an —OR group (R represents a hydrogen atom or a hydroxyl-protecting group). R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, A substituted oxycarbonyl group, an acyl group or an acyloxy group is shown. At least two of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ may be bonded to each other to form a double bond, and form a ring with the carbon atoms constituting the cyclic imide skeleton. May be. R ¹ , R ² , R ³ , R ⁴ , R ⁵ , or R ⁶ , or at least two of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are bonded together. In addition, one or two or more cyclic imide groups represented by the following formula (1) may be bonded to the ring formed together with the carbon atoms constituting the double bond or the cyclic imide skeleton.

The halogen atoms in the substituents R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ of the imide compound represented by the formula (1) include iodine, bromine, chlorine, and fluorine atoms. Examples of the alkyl group include about 1 to 30 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, hexyl, decyl, dodecyl, tetradecyl, and hexadecyl groups (particularly, carbon number). 1-20) linear or branched alkyl groups are included.

  Examples of the aryl group include phenyl and naphthyl groups, and examples of the cycloalkyl group include cyclopentyl and cyclohexyl groups. The alkoxy group includes, for example, about 1 to 30 carbon atoms such as methoxy, ethoxy, isopropoxy, butoxy, t-butoxy, hexyloxy, octyloxy, decyloxy, dodecyloxy, tetradecyloxy, octadecyloxy groups (particularly carbon The alkoxy group of Formula 1-20 is included.

Examples of the substituted oxycarbonyl group include C _1-30 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, t-butoxycarbonyl, hexyloxycarbonyl, decyloxycarbonyl, hexadecyloxycarbonyl groups ( In particular, C _1-20 alkoxy-carbonyl groups); cycloalkyloxycarbonyl groups such as cyclopentyloxycarbonyl and cyclohexyloxycarbonyl groups (particularly 3 to 20-membered cycloalkyloxycarbonyl groups); phenyloxycarbonyl, naphthyloxycarbonyl groups and the like aryloxycarbonyl group (especially, C _6-20 aryloxy - carbonyl group); aralkyloxycarbonyl group such as benzyloxycarbonyl group (particularly, C _7-21 aralkyloxy - carbonyl group).

Acyl groups include, for example, C _1-30 aliphatic acyl groups such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, pivaloyl, hexanoyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl groups (especially C ₁ Aliphatic saturated or unsaturated acyl groups such as _-20 aliphatic acyl groups; acetoacetyl groups; alicyclic acyl groups such as cycloalkanecarbonyl groups such as cyclopentanecarbonyl and cyclohexanecarbonyl groups; aromatics such as benzoyl and naphthoyl groups Group acyl group and the like.

Acyloxy groups include, for example, formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, pivaloyloxy, hexanoyloxy, octanoyloxy, decanoyloxy, lauroyloxy, myristoyloxy, palmitoyloxy, stearoyloxy An aliphatic saturated or unsaturated acyloxy group such as a C _1-30 aliphatic acyloxy group (particularly a C _1-20 aliphatic acyloxy group); an acetoacetyloxy group; a cyclopentanecarbonyloxy group, a cyclohexanecarbonyloxy group, etc. Examples include alicyclic acyloxy groups such as cycloalkanecarbonyloxy group; aromatic acyloxy groups such as benzoyloxy and naphthoyloxy groups.

Examples of the ring that may be formed together with the carbon atoms constituting the cyclic imide skeleton by bonding at least two of the substituents R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ to each other, for example, A 5- to 12-membered ring (particularly preferably a 6- to 10-membered ring). The ring includes a hydrocarbon ring, a heterocyclic ring, and a condensed heterocyclic ring. Specific examples of such a ring include a non-aromatic alicyclic ring (a cycloalkane ring which may have a substituent such as a cyclohexane ring, a cyclohexane which may have a substituent such as a cyclohexene ring). Alkene ring, etc.), non-aromatic bridged ring (bridged hydrocarbon ring optionally having substituent such as 5-norbornene ring), aromatic ring optionally having substituent ( (Including a condensed ring) (benzene ring, naphthalene ring, etc.). Examples of the substituent that the ring may have include, for example, an alkyl group, a haloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, a substituted oxycarbonyl group, an acyl group, an acyloxy group, a nitro group, a cyano group, and an amino group. And halogen atoms.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , or R ⁶ , or at least two of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are bonded together. In addition, one or two or more cyclic imide groups represented by the above formula (1) may be bonded to the ring formed together with the carbon atoms constituting the double bond or the cyclic imide skeleton, for example, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , or R ⁶ is an alkyl group having 2 or more carbon atoms, the two adjacent carbon atoms constituting the alkyl group are included to form the cyclic imide group. It may be. When at least two of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are bonded to each other to form a double bond, the cyclic imide group is formed including the double bond. You may do it. Furthermore, at least two of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be bonded to each other to form the cyclic imide group together with the carbon atoms constituting the cyclic imide skeleton. .

Preferred imide compounds include compounds represented by the following formula. In the formula, R ^{11 to} R ¹⁶ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, a substituted oxycarbonyl group, an acyl group, or an acyloxy group. Indicates a group. R ^{17 to} R ²⁶ are the same or different and each represents a hydrogen atom, an alkyl group, a haloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, a substituted oxycarbonyl group, an acyl group, an acyloxy group, a nitro group, a cyano group, an amino group, Or a halogen atom is shown. R ^{17 to} R ²⁶ are groups in which adjacent groups are bonded to each other to form a 5-membered or 6-membered member represented by the formula (1c), (1d), (1e), (1f), (1h), or (1i) The cyclic imide skeleton may be formed. A represents a methylene group or an oxygen atom. X is the same as above.

Halogen atom in the substituents R ¹¹ to R ^16, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, substituted oxycarbonyl group, an acyl group, the acyloxy group, in the R ¹ to R ⁶ Examples corresponding to the corresponding groups are exemplified.

As the alkyl group in the substituents R ^{17 to} R ^26, the same alkyl group as the above exemplified alkyl group (preferably an alkyl group having about 1 to 6 carbon atoms, particularly preferably a lower alkyl group having 1 to 4 carbon atoms). Examples of the haloalkyl group include a haloalkyl group having about 1 to 4 carbon atoms such as a trifluoromethyl group, and the alkoxy group is the same alkoxy group as described above (particularly a lower alkoxy group having about 1 to 4 carbon atoms). Examples of the oxycarbonyl group include the same substituted oxycarbonyl groups as described above (alkoxycarbonyl group, cycloalkyloxycarbonyl group, aryloxycarbonyl group, aralkyloxycarbonyl group, etc.). Examples of the acyl group include the same acyl groups as described above (aliphatic saturated or unsaturated acyl group, acetoacetyl group, alicyclic acyl group, aromatic acyl group, etc.), and the acyloxy group is the same as described above. Examples include acyloxy groups (aliphatic saturated or unsaturated acyloxy groups, acetoacetyloxy groups, alicyclic acyloxy groups, aromatic acyloxy groups, etc.). Examples of the halogen atom include fluorine, chlorine and bromine atoms. As the substituents R ^{17 to} R ²⁶ , a hydrogen atom, a lower alkyl group having about 1 to 4 carbon atoms, a carboxyl group, a substituted oxycarbonyl group, a nitro group, and a halogen atom are particularly preferable.

Moreover, since oxygen as an oxidizing agent is used in the presence of ozone, the gasoline base material as a reaction substrate can be oxidized with a very excellent oxidizing power. Therefore, the solubility parameter [SP value; the temperature at which the evaporation energy of oxygen atoms (—O—) constituting the ester bond is 3350 J / mol and the molar volume is 3.8 cm ³ / mol by the Fedors method of the imide compound (25 ° C. )] Exceeds, for example, 26 [(MPa) ^1/2 ] (preferably exceeds 26 [(MPa) ^1/2 ] and 40 [(MPa) ^1/2 ] or less). Even if it exists, reaction can be advanced rapidly in the absence of a solvent, and an oxide can be obtained efficiently. In addition, SP value is a method described in the literature [RFFedors, Polym. Eng. Sci., 14 (2), 147 (1974); EAGrulke, Polymer Handbook, VII / 675; Yuji Harasaki, Coating Technology, 3, 129 (1987) Reference].

  Typical examples of compounds having a 5-membered cyclic imide skeleton among preferred imide compounds include N-hydroxysuccinimide, N-hydroxy-α-methylsuccinimide, N-hydroxy-α, α-dimethylsuccinimide. N-hydroxy-α, β-dimethylsuccinimide, N-hydroxy-α, α, β, β-tetramethylsuccinimide, N-hydroxymaleimide, N-hydroxyhexahydrophthalimide, N, N ′ -Dihydroxycyclohexanetetracarboxylic acid diimide, N-hydroxyphthalimide, N-hydroxytetrabromophthalimide, N-hydroxytetrachlorophthalimide, N-hydroxyhetic acid imide, N-hydroxyheimic acid imide, N-hydroxytrimellitic acid imide, N, N'-dihydroxy Romellitic acid diimide, N, N′-dihydroxynaphthalenetetracarboxylic acid diimide, α, β-diacetoxy-N-hydroxysuccinimide, N-hydroxy-α, β-bis (propionyloxy) succinimide, N-hydroxy- α, β-bis (valeryloxy) succinimide, N-hydroxy-α, β-bis (lauroyloxy) succinimide, α, β-bis (benzoyloxy) -N-hydroxysuccinimide, N-hydroxy- 4-methoxycarbonylphthalimide, 4-ethoxycarbonyl-N-hydroxyphthalimide, N-hydroxy-4-pentyloxycarbonylphthalimide, 4-dodecyloxy-N-hydroxycarbonylphthalimide, N-hydroxy-4-phenoxycarbonylphthalimide, N- Hydro Xy-4,5-bis (methoxycarbonyl) phthalimide, 4,5-bis (ethoxycarbonyl) -N-hydroxyphthalimide, N-hydroxy-4,5-bis (pentyloxycarbonyl) phthalimide, 4,5-bis ( Dodecyloxycarbonyl) -N-hydroxyphthalimide, N-hydroxy-4,5-bis (phenoxycarbonyl) phthalimide and the like, wherein X is an —OR group and R is a hydrogen atom; Corresponding compounds wherein R is an acyl group such as an acetyl group, propionyl group, benzoyl group; formulas such as N-methoxymethyloxyphthalimide, N- (2-methoxyethoxymethyloxy) phthalimide, N-tetrahydropyranyloxyphthalimide X in (1) is an —OR group and R is a hydroxy group. A compound capable of forming an acetal or hemiacetal with an alkyl group; X in formula (1) such as N-methanesulfonyloxyphthalimide, N- (p-toluenesulfonyloxy) phthalimide, etc., and R is sulfonyl A compound which is a group; X in formula (1) such as sulfate, nitrate, phosphate or borate of N-hydroxyphthalimide is an —OR group and R is a group obtained by removing an OH group from an inorganic acid. Compounds and the like.

  Typical examples of compounds having a 6-membered cyclic imide skeleton among preferred imide compounds include N-hydroxyglutarimide, N-hydroxy-α, α-dimethylglutarimide, N-hydroxy-β, β-dimethylglutarimide. N-hydroxy-1,8-decalin dicarboxylic acid imide, N, N′-dihydroxy-1,8; 4,5-decalin tetracarboxylic acid diimide, N-hydroxy-1,8-naphthalenedicarboxylic acid imide (N— Hydroxy naphthalimide), N, N′-dihydroxy-1,8; compounds such as 4,5-naphthalenetetracarboxylic acid diimide wherein X is an —OR group and R is a hydrogen atom; Wherein R is an acyl group such as an acetyl group, a propionyl group, or a benzoyl group; N-methoxymethyl X in the formula (1) such as oxy-1,8-naphthalenedicarboxylic acid imide, N, N′-bis (methoxymethyloxy) -1,8; 4,5-naphthalenetetracarboxylic acid diimide is an —OR group; Compound in which R is a group capable of forming an acetal or hemiacetal with a hydroxyl group; N-methanesulfonyloxy-1,8-naphthalenedicarboxylic imide, N, N′-bis (methanesulfonyloxy) -1,8; 4 N-hydroxy-1,8-naphthalenedicarboxylic acid imide or N, N′-dihydroxy-, a compound in which X is an —OR group and R is a sulfonyl group in formula (1), such as 1,5-naphthalenetetracarboxylic acid diimide; 1,8; 4,5-naphthalene tetracarboxylic acid diimide sulfate, nitrate, phosphate or borate ester And the like, in which X in the formula (1) is an —OR group and R is a group obtained by removing an OH group from an inorganic acid.

  Among the imide compounds, a compound in which X is an —OR group and R is a hydrogen atom (N-hydroxyimide compound) is a conventional imidization reaction, for example, reacting a corresponding acid anhydride with hydroxylamine, It can be produced by a method of imidizing via ring opening and ring closing of an acid anhydride group. Of the imide compounds, a compound in which X is an —OR group and R is a hydroxyl protecting group is introduced into a compound (N-hydroxyimide compound) in which the corresponding R is a hydrogen atom (N-hydroxyimide compound). It can manufacture by introduce | transducing a desired protecting group using reaction. For example, N-acetoxyphthalimide can be produced by reacting N-hydroxyphthalimide with acetic anhydride or reacting acetyl halide in the presence of a base.

A particularly preferred imide compound is an N-hydroxyimide compound derived from an aliphatic polyvalent carboxylic anhydride or an aromatic polycarboxylic anhydride (for example, N-hydroxysuccinimide (SP value: 33.5 [( MPa) ^1/2 ]), N-hydroxyphthalimide (SP value: 33.4 [(MPa) ^1/2 ]), N, N′-dihydroxypyromellitic diimide, N-hydroxyglutarimide, N-hydroxy- 1,8-naphthalenedicarboxylic acid imide, N, N′-dihydroxy-1,8; 4,5-naphthalenetetracarboxylic acid diimide, etc.), and by introducing a protecting group into the hydroxyl group of the N-hydroxyimide compound The resulting compound is included.

  The imide compounds having a cyclic imide skeleton can be used alone or in combination of two or more. The imide compound may be produced in the reaction system. In the present invention, for example, trade name “N-hydroxyphthalimide” (manufactured by Wako Pure Chemical Industries, Ltd.), trade name “N-hydroxysuccinimide” ”(Manufactured by Wako Pure Chemical Industries, Ltd.) and the like can be suitably used.

  The amount of the imide compound having a cyclic imide skeleton is, for example, 0.0001 to 20 parts by weight, preferably 0.001 to 10 parts by weight, particularly preferably 0.001 to 100 parts by weight of the gasoline base material as a reaction substrate. 01 to 5 parts by weight. By using an imide compound having a cyclic imide skeleton within the above range, the oxidation reaction can proceed at an excellent reaction rate.

  In addition, when the oxidation reaction proceeds without using ozone in the presence of an imide compound having a cyclic imide skeleton, there is a period in which the oxidation reaction does not proceed (induction period), whereas the reaction occurs in the presence of oxygen and ozone. Then, the induction period disappears, and the oxidation reaction proceeds immediately after the start of the reaction. In other words, by making the oxidation reaction proceed in the coexistence of oxygen and ozone, it becomes possible to obtain gasoline with a high research octane number at an early stage.

[Other radical generators]
In the present invention, when a gasoline composition is prepared by oxidizing a gasoline base material, as a radical generator other than imide compounds having ozone and a cyclic imide skeleton (referred to as other radical generators), known and commonly used radical generation An agent may be used, for example, a nitroxy radical generator or an azo radical generator may be used.

  Examples of the nitroxy-based radical generator include 2,2,6,6-tetramethylpiperidine-1-oxyl, 9-azabicyclo [3.3.1] nonane-N-oxyl, 2-azaadamantane-N—. Examples thereof include oxyl, 1-methyl-2-azaadamantane-N-oxyl, 1,3-dimethyl-2-azaadamantane-N-oxyl and the like.

  Examples of the azo radical generator include dimethyl 2,2′-azobis (2-methylpropionate), 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile, 2,2 ′. -Azobis (isobutyronitrile), 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), 4,4'-azobis (4-cyano Valeric acid), 2,2′-azobis (2-amidinopropane) dihydrochloride, 2,2′-azobis [2- (2-imidazolin-2-yl) propane] dihydrochloride, 1,1′-azobis (Cyclohexane-1-carbonitrile), 4,4′-azobis (4-cyanopentanoic acid), 2,2′-azobis (methyl isobutyrate), 2,2′-azobis (ethyl isobutyrate), etc. Mention may be made of the zone compound.

[Cocatalyst]
In the present invention, when preparing a gasoline composition by oxidizing a gasoline base material, a metal compound may be used as a promoter.

  The metal compound includes a metal compound containing at least one metal element selected from cobalt, manganese, zirconium, and molybdenum, that is, at least one selected from a cobalt compound, a manganese compound, a zirconium compound, and a molybdenum compound. It is preferable to use it.

  Examples of the metal compound include the metal element simple substance, a hydroxide of the metal element, an oxide (including a complex oxide), a halide (fluoride, chloride, bromide, iodide), an oxo acid salt (for example, Inorganic compounds such as nitrates, sulfates, phosphates, borates, carbonates, etc., salts of isopolyacids, salts of heteropolyacids; organic acid salts (eg acetates, propionates, cyanates, naphthenic acids) Salts, stearates, etc.), complexes and the like.

Examples of the ligand constituting the complex include OH (hydroxo), alkoxy (methoxy, ethoxy, propoxy, butoxy, etc.), acyl (acetyl, propionyl, etc.), alkoxycarbonyl (methoxycarbonyl, ethoxycarbonyl, etc.), acetylacetonato , Cyclopentadienyl, halogen atoms (chlorine, bromine, etc.), CO, CN, oxygen atoms, H ₂ O (aquo), phosphines (triarylphosphine such as triphenylphosphine), phosphorus compounds, NH ₃ (ammine) , NO, NO ₂ (nitro), NO ₃ (nitrato), nitrogen-containing compounds such as ethylenediamine, diethylenetriamine, pyridine, phenanthroline, and the like.

  Taking a cobalt compound as an example of a metal compound, inorganic compounds such as cobalt hydroxide, cobalt oxide, cobalt chloride, cobalt bromide, cobalt nitrate, cobalt sulfate, and cobalt phosphate; cobalt acetate, cobalt naphthenate, cobalt stearate, etc. Organic acid salts of: divalent or trivalent cobalt compounds such as complexes of cobalt acetylacetonate and the like. Examples of other metal element compounds include compounds corresponding to the cobalt compounds. In addition, it is preferable to use at least a cobalt compound from the point which is especially excellent in the reaction promotion effect, and it is preferable to use it combining a cobalt compound and a manganese compound especially. The metal compound may be added all at the time of preparation, or may be added continuously or intermittently in the reaction system.

  In the present invention, when a gasoline composition is prepared by oxidizing a gasoline base material, the oxidation reaction can be performed by a conventional method such as a batch system, a semi-batch system, or a continuous system. From the viewpoint of improving the rate, it is preferably a continuous type.

  Hereinafter, specific examples of the present invention will be described with reference to examples and comparative examples. However, the present invention is not limited to these.

(Spray ignition test)
When the hydrocarbon component contained in regular gasoline is oxidized and oxygenated hydrocarbons such as alcohol and ketone are produced, the boiling point of the oxidation reaction liquid becomes significantly higher than the boiling point of regular gasoline. For this reason, the research octane number of the oxidation reaction liquid was estimated by a spray ignition test capable of measuring high boiling point fuel.
After the combustion chamber is heated to 500 ° C. by a heater attached to the outer wall, 20 g of a measurement sample is charged into a fuel reservoir and compressed 400 times with an air cylinder. A measurement sample is injected from the combustion reservoir through a nozzle inserted into the combustion chamber into the combustion chamber at a high pressure for 10 milliseconds. The research octane number was studied by evaluating the ignition delay time and the heat generation behavior.

Example 1
A 100 mL SUS316 pressure-resistant reactor (TVS-1 type, manufactured by Pressure Glass Industrial Co., Ltd.) equipped with a gas ventilation line and an insertion rod, 20% by weight of toluene, 63% equivalent to regular gasoline with a research octane number of 90 % Of 2,4,4-trimethylpentane and 17% by weight of n-heptane (hereinafter referred to as raw material) were added. After immersing the reactor in an oil bath to a liquid temperature of 95 ° C., air containing ozone gas generated using an ozone generator (Wintech Co., Ltd.) (oxygen concentration: 20.7% by volume, ozone gas) The raw material was oxidized by bubbling and supplying (content: 0.3% by volume). This reaction solution was subjected to component analysis by gas chromatography (column: 007-FFAP). When the raw material conversion reached 10%, the supply of ozone gas was stopped and the reactor was cooled to room temperature. The results of component analysis are listed in Table 1. Thereafter, the research octane number was measured by subjecting the obtained reaction liquid (gasoline composition) to a spray ignition test. The results are shown in Table 1. The “conversion rate of the raw material” was calculated by [the disappearance amount of the raw material in the reaction liquid (mole)] / [the raw material before the reaction (mole)].

  Furthermore, from the results of component analysis, the oxygen-containing hydrocarbon content, alcohol component content, ketone component content, and oxygen content rate with respect to the gasoline composition (reaction liquid) were calculated and listed in Table 1. Here, “oxygen-containing hydrocarbon” refers to an oxide (compound) derived from a raw material. In addition, the content ratio of each component by component analysis, the content rate of oxygen-containing hydrocarbons, the content rate of alcohol components, the content rate of ketone components, and the oxygen content rate are values rounded to one decimal place.

(Examples 2 to 5)
The same operation as in Example 1 was performed to prepare gasoline compositions having a raw material conversion of 20%, 30%, 40%, and 50%. Table 1 shows the content ratio of components contained in the gasoline composition, the measured value of the research octane number, the content rate of oxygen-containing hydrocarbons, the content rate of alcohol components, the content rate of ketone components, and the oxygen content rate.

(Comparative Example 1)
The research octane number was measured by subjecting the raw material to a spray ignition test. Table 1 shows the content ratio of components contained in the raw material, the oxygen-containing hydrocarbon content rate, the alcohol component content rate, the ketone component content rate, and the oxygen content rate together with the results.

  Moreover, the correlation diagram of the conversion rate of a raw material and the research octane number of a gasoline composition is shown in FIG. Furthermore, the correlation diagram of the content rate of the alcohol component of a gasoline composition, the content rate of a ketone component, and oxygen content rate, and the research octane number of a gasoline composition is shown to FIGS.

  From Table 1, it became clear that the research octane number of the gasoline composition was improved as the oxygen-containing hydrocarbon content increased. Further, FIG. 1 shows that when the oxygen-containing hydrocarbon content reaches 27%, a gasoline composition equivalent to high octane fuel (RON = 100) is obtained. Furthermore, it can be understood from FIGS. 2 to 4 that the Lisa thiooctane number increases as the oxygen content of the gasoline composition increases. Moreover, when the content of the ketone component was increased in the range of about 0 to 1.5% by weight, it was found that the research octane number of the gasoline composition was efficiently increased.

(Comparative example 2, Examples 6-11)
Gasoline compositions 1 to 7 containing the components shown in Table 2 were prepared. Furthermore, the research octane number of the gasoline compositions 1-7 was measured based on the spray ignition test method.

  As is clear from Comparative Example 2 and Examples 6 to 11 (research octane numbers of gasoline compositions 1 to 7), the carbon number of 3 to 10 such as heptanol, 2-heptanol, 2,2-dimethyl-1-propanol, etc. A gasoline composition by adding a C 3-10 ketone such as alcohol, acetone or 2-heptanone, a C 3-10 aldehyde such as benzaldehyde, or a C 3-10 carboxylic acid such as benzoic acid. It became clear that the research octane number improved.

Claims (7)

A gasoline composition comprising at least one selected from the group consisting of a ketone having 3 to 10 carbon atoms and an aldehyde having 3 to 10 carbon atoms, and a gasoline base material,
The content of the ketone having 3 to 10 carbon atoms is 0.1% by weight or more based on the total amount of the composition, or the content of the aldehyde having 3 to 10 carbon atoms is 0.1% relative to the total amount of the composition. A gasoline composition characterized by being 5% by weight or more. The ketone having 3 to 10 carbon atoms is acetone, 2-heptanone, 3-heptanone, 4-heptanone, or 2,3-heptanedione;
The gasoline composition according to claim 1, wherein the aldehyde having 3 to 10 carbon atoms is heptanal, 2,2-dimethyl-1-propanal, or benzaldehyde.   Furthermore, the gasoline composition of Claim 1 or 2 containing a C3-C10 alcohol.   C3-C10 alcohol is 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 1,2-heptanediol, 1,7-heptanediol, 2,2-dimethyl-1-propanol, 2 The gasoline composition according to claim 3, 4,4-trimethyl-2-pentanol or benzyl alcohol.   Furthermore, the gasoline composition of any one of Claims 1-4 containing C3-C10 carboxylic acid.   The gasoline composition according to claim 5, wherein the carboxylic acid having 3 to 10 carbon atoms is 2,2-dimethyl-1-propanoic acid, heptanoic acid, heptanedioic acid, or benzoic acid.   The gasoline composition according to any one of claims 1 to 6, which has a research octane number of 89 or more in a spray ignition test.

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