CN114423830B - Cycloparaffin solvent - Google Patents
Cycloparaffin solvent Download PDFInfo
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- CN114423830B CN114423830B CN202080065288.4A CN202080065288A CN114423830B CN 114423830 B CN114423830 B CN 114423830B CN 202080065288 A CN202080065288 A CN 202080065288A CN 114423830 B CN114423830 B CN 114423830B
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/44—Hydrogenation of the aromatic hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/18—Solvents
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
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- Detergent Compositions (AREA)
Abstract
A cycloalkane solvent characterized in that the hydrocarbon component content at a boiling point of 190-310 ℃ is 90.0% by volume or more, the aromatic hydrocarbon component content is 1.0% by volume or less, the cycloalkane component content at a 2-ring or more is 70.0% by volume or more, the flash point is 70.0 ℃ or more, and the aniline point is 48.0-75.0 ℃, and the petroleum fraction raw material is a petroleum fraction having a hydrocarbon component content of 90.0% by volume or more, an aromatic hydrocarbon component content of 11-18 carbon atoms of 90.0% by mass or more, an aromatic hydrocarbon component content of 70.0% by mass or more, and a hydrocarbon component content of 14-18 carbon atoms of 68.0% by mass or more, and a hydrocarbon component content of 50.0% by volume or more at a boiling point of 250 ℃ or more. According to the present invention, a cycloalkane solvent having a low aromatic hydrocarbon content and a high flash point and having an aniline point not too low can be provided.
Description
Technical Field
The present invention relates to a low aromatic cycloalkane solvent having a limited aromatic hydrocarbon content.
Background
Conventionally, aromatic hydrocarbon solvents produced by petroleum refining have been widely used as solvents for washing, paints, printing inks, etc., solvents for dispersion media, adhesives, etc., because of their high solubility. However, aromatic compounds have a limited use because they have an environmental load in addition to a strong odor. For example, toluene, xylene, and methyl isobutyl ketone (MIBK), which are aromatic solvents, are used in limited applications from the viewpoint of environmental load. In order to meet the organic solvent poisoning prevention regulations, it is necessary to measure the working environment at the time of use, and the user is required to be diagnosed for periodic health diagnosis, and to store the solvents for use, and the like, and the load is high even in terms of management.
Therefore, in recent years, in fields such as solvents for paint applications for automobiles, buildings, and the like, low aromatic solvents having a low aromatic hydrocarbon content are used. Examples of the low aromatic solvent include a cycloalkane solvent, an alcohol solvent, a alkane solvent, and an aqueous solvent.
Among them, a cycloalkane solvent is not high in solubility as compared with an aromatic solvent in the field of petroleum solvents, but is high in solubility as compared with a alkane solvent, and therefore, a cycloalkane solvent is widely used in printing ink solvents for food packaging, stationery solvents, reaction solvents for producing medical and agricultural chemicals, metal detergents, adhesives, sintering paint solvents, and the like.
As a cycloalkane solvent, for example, patent document 1 discloses a cycloalkane solvent having an aromatic component content of 1% by volume or less, which is obtained by hydrogenating a petroleum fraction having a boiling point of 175 to 280 ℃ and containing 80% by volume or more of an aromatic component having 9 to 14 carbon atoms and 10% by volume or more of a cyclic hydrocarbon having 2 or more rings.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2006-96786
Disclosure of Invention
Problems to be solved by the invention
However, the cycloalkane-based solvent in the nuclear hydrogenation test 1 or 2 of the example of patent document 1 has a flash point too low and is 40℃or 51 ℃. When these are used in a washing solvent, a reaction solvent, a baking paint solvent, or the like, there are problems that the flash point is too low, that is, the ignition property is high, and therefore, equipment is required in terms of use environment, and the like, and that the treatment must be sufficiently carried out, and that the limitation on the treatment in terms of the amount used, the amount of storage, and the like becomes strict from the viewpoint of fire protection law.
On the other hand, the naphthene-based solvent of the example of patent document 1 in the nuclear hydrogenation test 3 had a flash point of 68℃to some extent, but had a low aniline point of 39 ℃. On the other hand, if the aniline point is too low, the solubility is too high, and therefore, when the solvent is used for a paint or the like, if the material on the coating side is a plastic or a polymer resin, the solvent may dissolve the coating surface depending on the material, and there is a problem that the coating cannot be smoothly performed.
Accordingly, an object of the present invention is to provide a cycloalkane-based solvent having a low aromatic hydrocarbon content and a high flash point, and having an aniline point not too low.
Solution for solving the problem
The above problems are solved by the present invention as follows.
Specifically, the present invention (1) provides a cycloalkane-based solvent which is a hydrogenated product of a petroleum fraction raw material or a distilled fraction of a light component or a heavy component of the hydrogenated product,
the content of hydrocarbon components having a boiling point of 190 to 310 ℃ is 90.0% by volume or more, the content of aromatic hydrocarbons is 1.0% by volume or less, the content of naphthenes having a 2-ring or more is 70.0% by volume or more, the flash point is 70.0 ℃ or more, and the aniline point is 48.0 to 75.0 ℃,
the petroleum fraction raw material is a petroleum fraction having a hydrocarbon component content of 90.0% by volume or more at a boiling point of 230 to 330 ℃, an aromatic hydrocarbon component content of 90.0% by mass or more at a carbon number of 11 to 18, an aromatic hydrocarbon component content of 70.0% by mass or more at a 2-ring or more, a hydrocarbon component content of 68.0% by mass or more at a carbon number of 14 to 18, and a hydrocarbon component content of 50.0% by volume or more at a boiling point of 250 ℃ or more.
The present invention (2) provides the cycloalkane-based solvent of (1), which satisfies the following formula (1):
145≤X+2Y≤160 (1)
(wherein X represents an aniline point (. Degree. C.) and Y represents kauri-butanol value).
The present invention (3) provides the cycloalkane-based solvent of (1) or (2), wherein the hansen sphere radius R of hansen solubility parameter is 7.5 or more.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a cycloalkane solvent having a low aromatic hydrocarbon content and a high flash point and having an aniline point not too low can be provided.
Drawings
Fig. 1 is a schematic diagram for explaining the hansen ball method.
Detailed Description
The cycloalkane solvent of the present invention is characterized in that it is a hydrogenated product of a petroleum fraction raw material or a distilled fraction of a light component or a heavy component of the hydrogenated product,
the content of hydrocarbon components having a boiling point of 190 to 310 ℃ is 90.0% by volume or more, the content of aromatic hydrocarbons is 1.0% by volume or less, the content of naphthenes having a 2-ring or more is 70.0% by volume or more, the flash point is 70.0 ℃ or more, and the aniline point is 48.0 to 75.0 ℃,
the petroleum fraction raw material is a petroleum fraction having a hydrocarbon component content of 90.0% by volume or more at a boiling point of 230 to 330 ℃, an aromatic hydrocarbon component content of 90.0% by mass or more at a carbon number of 11 to 18, an aromatic hydrocarbon component content of 70.0% by mass or more at a 2-ring or more, a hydrocarbon component content of 68.0% by mass or more at a carbon number of 14 to 18, and a hydrocarbon component content of 50.0% by volume or more at a boiling point of 250 ℃ or more.
The cycloalkane solvent of the present invention is a hydrogenated product of a petroleum fraction raw material obtained by a petroleum refining process, or a distilled fraction of a light component or a heavy component of a hydrogenated product of the petroleum fraction raw material, and is a hydrogenated product obtained by subjecting a fraction containing an aromatic hydrocarbon component having 11 to 18 carbon atoms produced by the petroleum refining process to nuclear hydrogenation, or a distilled fraction obtained by subjecting a light component or a heavy component of a hydrogenated product obtained by subjecting a petroleum fraction raw material to nuclear hydrogenation to distillation and cutting.
In the present invention, in the petroleum fraction raw material which is a hydrogenated raw material, the hydrocarbon component having a boiling point of 230 to 330 ℃ is 90.0% by volume or more, preferably the hydrocarbon component having a boiling point of 230 to 320 ℃ is 90.0% by volume or more, more preferably the hydrocarbon component having a boiling point of 230 to 320 ℃ is 95.0% by volume or more, and particularly preferably the hydrocarbon component having a boiling point of 230 to 320 ℃ is 98.0% by volume or more. When the content of the hydrocarbon component in the boiling point range of the petroleum fraction raw material falls within the above range, a cycloalkane solvent having a high flash point and an aniline point not too low can be obtained. In the present invention, the distillation property was determined according to JIS K2254, JIS K2435-1, and JIS K0066.
In the petroleum fraction raw material of the present invention, the content of the aromatic hydrocarbon component having 11 to 18 carbon atoms is 90.0 mass% or more, preferably 94.0 mass% or more, and particularly preferably 98.0 mass% or more. When the content of the aromatic hydrocarbon component having 11 to 18 carbon atoms in the petroleum fraction raw material falls within the above range, a cycloalkane solvent having a high flash point can be obtained. On the other hand, if the content of the aromatic hydrocarbon component having 11 to 18 carbon atoms in the petroleum fraction raw material is smaller than the above range, the aniline point of the cycloalkane solvent is too high.
Examples of the aromatic hydrocarbon having 11 to 18 carbon atoms include pentamethylbenzene, diethylmethylbenzene, methylbutylbenzene, methylnaphthalene, dimethylnaphthalene, ethylnaphthalene, hexamethylbenzene, triethylbenzene, ethylmethylnaphthalene, tetramethylnaphthalene, diethylnaphthalene, triethylnaphthalene, phenanthrene, anthracene, pyrene, 1, 2-benzophenanthrene, and tetracene.
In the petroleum fraction raw material of the present invention, the content of the 2-ring or more aromatic hydrocarbon component is 70.0% by mass or more, preferably 75.0% by mass or more, and particularly preferably 78.0% by mass or more. If the content of the cyclic hydrocarbon component having 2 or more rings in the petroleum fraction raw material is less than the above range, the flash point is less than 70 ℃, and thus the limitation of the treatment increases.
In the petroleum fraction raw material of the present invention, the content of the aromatic hydrocarbon component having 14 to 18 carbon atoms is 68.0 mass% or more, preferably 70.0 mass% or more, and particularly preferably 73.0 mass% or more. When the content of the aromatic hydrocarbon component having 14 to 18 carbon atoms in the petroleum fraction raw material falls within the above range, a cycloalkane solvent having a high flash point and an aniline point not too low can be obtained. On the other hand, if the content of the aromatic hydrocarbon component having 14 to 18 carbon atoms in the petroleum fraction raw material is smaller than the above range, the aniline point of the cycloalkane solvent is too high.
In the petroleum fraction raw material of the present invention, the content of the hydrocarbon component having a boiling point of 250 ℃ or higher is 50.0% by volume or higher, preferably 55.0% by volume or higher, and particularly preferably 60.0% by volume or higher. When the content of the hydrocarbon component having a boiling point of 250 ℃ or higher in the petroleum fraction raw material falls within the above range, a cycloalkane solvent having a high flash point and an aniline point not too low can be obtained. On the other hand, if the content of hydrocarbon components having a boiling point of 250 ℃ or higher in the petroleum fraction raw material is smaller than the above range, the flash point of the cycloalkane-based solvent is too low.
In the present invention, the content of the aromatic hydrocarbon component having 11 to 18 carbon atoms, the content of the aromatic hydrocarbon component having 2 or more rings, and the content of the hydrocarbon component having 14 to 18 carbon atoms in the petroleum fraction raw material were determined by IP548 (DETERMINATION OF AROMATICHYDROCARBON TYPES IN MIDDLE DISTILLATES-HIGH PERFORMANCE LIQUID CHROMATOGRAPHY METHOD WITH REFRACTIVE INDEX DETECTION) and ASTM D2887 (Standard Test Method for Boiling Range Distribution of Petroleum Fractions by Gas Chromatography (C5-C44)).
The catalyst used for the nuclear hydrogenation of the petroleum fraction raw material of the present invention is not particularly limited, and examples thereof include catalysts used for the nuclear hydrogenation of aromatic hydrocarbons in fractions containing aromatic hydrocarbons in petroleum refining processes. Examples of the catalyst include nickel, nickel oxide, nickel/diatomaceous earth, raney nickel, nickel/copper, platinum oxide, platinum/activated carbon, platinum/rhodium, platinum/alumina, palladium/alumina, ruthenium/alumina, and the like. The conditions for subjecting the petroleum fraction raw material to nuclear hydrogenation are not particularly limited, and the conditions used in the petroleum refining process are appropriately selected. The nuclear hydrogenation conditions may be, for example, those selected appropriately from the reaction temperature of 80 to 280℃and the hydrogen pressure of 1 to 8 MPa.
In the present invention, a hydrogenated product of the petroleum fraction feedstock obtained by subjecting the petroleum fraction feedstock to nuclear hydrogenation may be used as the cycloalkane-based solvent of the present invention. In the present invention, a distillate obtained by distilling and cutting a part of the light component and/or a part of the heavy component from a hydrogenated product of the petroleum fraction raw material obtained by subjecting the petroleum fraction raw material to nuclear hydrogenation may be used as the cycloalkane-based solvent of the present invention. The degree to which the light component or the heavy component is cut is appropriately selected according to the requirements of the cycloalkane-based solvent.
The naphthene-based solvent of the present invention, that is, the naphthene-based solvent obtained by hydrogenating the petroleum fraction raw material of the present invention has a hydrocarbon component content of 90.0% by volume or more at a boiling point of 190 to 310 ℃, preferably a hydrocarbon component content of 90.0% by volume or more at a temperature of 190 to 305 ℃, and particularly preferably a hydrocarbon component content of 95.0% by volume or more at a temperature of 190 to 305 ℃. The content of the hydrocarbon component whose boiling point is within the above range by the cycloalkane-based solvent is within the above range, the flash point of the cycloalkane-based solvent is raised and the aniline point is not excessively low.
In the cycloalkane-based solvent of the present invention, the content of aromatic hydrocarbons is 1.0% by volume or less, preferably 0.5% by volume or less. In the present invention, the content of aromatic hydrocarbons was determined by the naphthalene component test method (ultraviolet absorption spectrophotometry) according to JIS K2276 petroleum product-aviation fuel oil test method.
In the cycloalkane-based solvent of the present invention, the content of cycloalkanes having 2 or more rings is 70.0% by volume or more, preferably 75.0% by volume or more, and particularly preferably 78.0% by volume or more. When the content of 2 or more rings in the cycloalkane solvent falls within the above range, the flash point of the cycloalkane solvent is raised and the aniline point is not excessively low. On the other hand, if the content of 2-ring or more cycloalkanes in the cycloalkane solvent is smaller than the above range, the flash point of the cycloalkane solvent is lowered and the aniline point is too low.
In the present invention, the content of each of 1-ring cycloalkanes, 2-ring cycloalkanes, 3-ring cycloalkanes, 4-ring cycloalkanes, 5-ring cycloalkanes, and 6-ring cycloalkanes in the cycloalkane solvent was determined by ASTM D2786 (Standard Test Method for Hydrocarbon Types Analysis of Gas-Oil Saturates Fractions by High Ionizing Voltage Mass Spectrometry) and ASTM D3239 (Standard Test Method for Aromatic Types Analysis of Gas-Oil Aromatic Fractions by High Ionizing Voltage Mass Spectrometry).
The flash point of the cycloalkane-based solvent of the present invention is 70.0℃or higher, preferably 72.0℃or higher, and particularly preferably 75.0℃or higher. When the flash point of the cycloalkane-based solvent falls within the above range, the classification of dangerous materials by the fire control law is classified into group 4 and group 3 petroleum, and the limitation in handling is relaxed, so that more solvents can be handled, and the ignitability is lowered even when used, and therefore, the solvent is not easy to use because of occurrence of accidents such as fire. On the other hand, if the flash point of the cycloalkane-based solvent is smaller than the above range, the classification of dangerous materials by the fire control law is classified into group 4, group 2, or group 1 petroleum, and the treatment is limited to increase, and the ignition property is increased, so that the danger at the time of use is increased. In the present invention, the flash point was determined according to JIS K2265.
The aniline point of the cycloalkane-based solvent of the present invention is 48.0 to 75.0 ℃, preferably 50.0 to 70.0 ℃, and particularly preferably 50.0 to 60.0 ℃. The aniline point of the cycloalkane solvent falls within the above range, and the solvent has suitable solubility and has little influence on the material on the coating side. On the other hand, if the aniline point of the cycloalkane solvent is smaller than the above range, the solubility is too high, and therefore, when the solvent is used for a paint or the like, if the material on the coating side is plastic, polymer resin or the like, the solvent may dissolve the coating surface depending on the material, and there is a problem that the coating cannot be smoothly performed. If the amount exceeds the above range, the solubility is lowered, and the oil or fat in the paint is not uniformly dissolved, and the use as a paint solvent is limited. In the present invention, the aniline point was obtained according to JIS K2256.
The cycloalkane-based solvent of the present invention preferably satisfies the following formula (1):
145≤X+2Y≤160 (1)
(wherein X represents an aniline point (. Degree. C.) and Y represents kauri-butanol value)
Particularly preferably, the following formula (2) is satisfied:
150≤X+2Y≤155 (2)
(wherein X represents an aniline point (. Degree. C.) and Y represents kauri-butanol value).
When the value of "x+2y" of the cycloalkane-based solvent falls within the above range, the kauri-butanol value can be raised by having an appropriate aniline point, and thus the solvent is a solvent which can properly maintain the solubility of the oil and has a high oil saturation capacity of a sample such as a paint. In the present invention, kauri-butanol value was determined according to ASTM D1133 (Standard Test Method for Kauri-Butanol Value of Hydrocarbon Solvents).
In the cycloalkane-based solvent of the present invention, the energy (δd) of the hansen solubility parameter due to intermolecular dispersion force is preferably 16.6 to 17.5, and particularly preferably 16.8 to 17.3. In the cycloalkane-based solvent of the present invention, the energy (δp) derived from intermolecular dipole interaction is preferably 5.5 to 6.5, and particularly preferably 5.7 to 6.3. In the cycloalkane-based solvent of the present invention, the energy (δh) derived from the intermolecular hydrogen bond is preferably 2.2 to 3.2, and particularly preferably 2.4 to 3.0. The hansen solubility parameter of the cycloalkane-based solvent of the present invention falls within the above range, and thus the solvent is excellent in compatibility with materials such as resins used in usual paints.
In the cycloalkane-based solvent of the present invention, the hansen sphere radius R of hansen solubility parameter is preferably 7.5 or more, and particularly preferably 7.5 to 9.0. The hansen sphere radius R of the hansen solubility parameter of the cycloalkane solvent of the present invention falls within the above range, and is a solvent which maintains the target range of the dissolvable substance and suppresses excessive dissolution of the material on the coating side and the like.
In the present invention, hansen solubility parameters and hansen sphere radius R were measured by the following methods.
Hansen solubility parameters (Hansen solubility parameter (hereinafter also simply referred to as "HSP")) are based on the idea that 2 substances having similar intermolecular interactions are easily dissolved in each other. HSP is composed of energy (δd) derived from intermolecular dispersion force, energy (δp) derived from intermolecular dipole interaction, and energy (δh) derived from intermolecular hydrogen bond. These 3 parameters can be regarded as coordinates in three-dimensional space (hansen space).
Thus, hansen solubility parameter (δt) was calculated using the following equation.
δt＝(δd 2 +δp 2 +δh 2 ) 0.5
The HSP value of the evaluation sample whose HSP value is unknown can be calculated by the following method.
In a hansen solubility parameter space specified by plotting HSP values (δdm, δpm, δhm) in a three-dimensional space, a plurality of pure substances (substances formed of 1 compound) having known HPS values are plotted, and the central value of hansen balls is obtained by evaluating the presence or absence of the solubility of a sample in the pure substances, thereby calculating the HSP value of the evaluation sample (hansen ball method).
The HSP value of the evaluation sample may be calculated from information on the average molecular structure by the atomic group contribution method.
In the case of hansen ball method and in the case of atomic group contribution method, the HSP value of the evaluation sample can be calculated by using computer software Hansen Solubility Parameters in Practice (hsppi), for example.
In the case of hansen ball method, the evaluation sample may be a pure substance or a mixture.
The method for obtaining the center values of hansen balls, that is, HSP values (δdm, δpm, δhm) will be described with reference to fig. 1.
First, the HSP values of about 15 to 30 pure substances having known HSP values are plotted in a three-dimensional space in which the dispersion force term δd, the dipole-dipole force term δp, and the hydrogen bond force term δh are taken as coordinate axes, as illustrated in fig. 1.
In this case, as shown in fig. 1, for example, a pure substance exhibiting solubility in an evaluation sample is represented by an o symbol, and a pure substance not exhibiting solubility in an evaluation sample is represented by an x symbol. Next, based on the solubility of the drawn evaluation sample, among the imaginary spheres containing the pure substance exhibiting solubility (indicated by the ∈ symbol in fig. 1) and not containing the pure substance not exhibiting solubility (indicated by the × symbol in fig. 1), the imaginary sphere having the smallest radius (indicated by the spherical shape in fig. 1) was obtained as hansen sphere S.
The radius (minimum radius) of the hansen ball S was the pure substance indicated by the symbol o in the dissolution chart, and the interaction radius R showing compatibility, i.e., hansen ball radius R, and the center values (δdm, δpm, δhm) of the obtained hansen balls S were HSP values of the evaluation samples.
As the HSP value of the pure substance used for obtaining Hansen balls, for example, the dispersion force term δd is 10 to 25MPa 1/2 The force term delta p between left and right dipoles is 0-20 MPa 1/2 The left and right hydrogen bond force term delta h is 0-20 MPa 1/2 Left and right.
In addition, since solubility depends on temperature, it is preferable to perform the solubility test at a temperature at which dissolution is actually performed when the hansen balls are obtained.
The density of the cycloalkane-based solvent of the present invention is preferably 0.85 to 0.90g/cm 3 Particularly preferably 0.87 to 0.89g/cm 3 . In the present invention, the density was obtained in accordance with JIS K2249.
The sulfur content of the cycloalkane-based solvent of the present invention is preferably 5 mass ppm or less, and particularly preferably 1 mass ppm or less. In the present invention, the sulfur content was determined in accordance with JIS K2541-6.
The nitrogen content of the cycloalkane-based solvent of the present invention is preferably 5 mass ppm or less, and particularly preferably 1 mass ppm or less. In the present invention, the nitrogen content was determined according to JIS K2609.
The cycloalkane-based organic solvent of the present invention is suitably used for a solvent for printing ink for food packaging, a solvent for stationery, a reaction solvent for pharmaceutical or agricultural chemical production, a detergent such as a metal detergent, a solvent for an adhesive, a solvent for a baking paint, and the like.
The present inventors have found that, as a hydrogenation raw material, a petroleum fraction having a boiling point of 230 to 330 ℃, preferably 230 to 320 ℃, and a content of an aromatic hydrocarbon component having 11 to 18 carbon atoms of 90.0 mass% or more, preferably 94.0 mass% or more, particularly preferably 98.0 mass% or more, and a content of an aromatic hydrocarbon component having 2 or more rings, a hydrocarbon component having 14 to 18 carbon atoms, and a hydrocarbon component having a boiling point of 250 ℃ or more, which are within the above-mentioned ranges, is selected, the petroleum fraction is hydrogenated, thus, a cycloalkane-based solvent having a flash point of at least 70.0 ℃, preferably at least 72.0 ℃, particularly preferably at least 75.0 ℃, and an aniline point which maintains good solubility and is not excessively low, at least 48.0 to 75.0 ℃, preferably at least 50.0 to 70.0 ℃, particularly preferably at least 50.0 to 60.0 ℃, is obtained, wherein the content of the hydrocarbon component having a boiling point of 190 to 310 ℃ is at least 90.0% by volume, preferably at least 90.0% by volume, particularly preferably at least 190 to 305 ℃, and the content of the hydrocarbon component having a boiling point of 190 to 305 ℃ is at least 95.0% by volume, particularly preferably at least 2 ring and at least 70.0% by volume, preferably at least 75.0% by volume, particularly preferably at least 78.0% by volume.
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
Examples
Example 1
The continuous flow reaction apparatus was filled with 50ml of a catalyst (Ni 5256E, manufactured by N.E. CHEMCAT CORPORATION). Then, in the catalyst layer of the continuous flow reaction apparatus, the reaction temperature was 180℃and the hydrogen pressure was 2.8MPa, and the space velocity (LHSV) was 3.5 hours -1 The petroleum fraction having the properties shown in Table 1 was mixed with methylcyclohexane at 10% by volume, hydrogenated, and the resulting oil was distilled and fractionated with methylcyclohexane to obtain a cycloalkane solvent. The analysis results of the obtained cycloalkane-based solvent are shown in Table 2. Further, hansen solubility parameters and hansen sphere radius R of the obtained cycloalkane solvent were obtained. The results are shown in Table 3.
Comparative example 1
Hydrogenation was performed in the same manner as in example 1 except that the petroleum fractions shown in Table 1 were used to obtain a cycloalkane-based solvent. The analysis results of the obtained cycloalkane-based solvent are shown in Table 2. Further, hansen solubility parameters and hansen sphere radius R of the obtained cycloalkane solvent were obtained. The results are shown in Table 3.
Comparative example 2
Analysis was performed on AF Solvent No. 7 (manufactured by JXTG NIPPON OIL & ENERGY CORPORATION). The results are shown in Table 2. In addition, hansen solubility parameters and hansen sphere radius R of AF Solvent No. 7 were obtained. The results are shown in Table 3.
Comparative example 3
Analysis of Teclean N22 (JXTG NIPPON OIL & ENERGY CORPORATION). The results are shown in Table 2. In addition, the method comprises the following steps. The hansen solubility parameter and hansen sphere radius R of Teclean N22 were determined. The results are shown in Table 3.
Example 2
The continuous flow reaction apparatus was filled with 50ml of a catalyst (Ni 5256E, manufactured by N.E. CHEMCAT CORPORATION). Then, in the catalyst layer of the continuous flow reaction apparatus, the reaction temperature was 190℃and the hydrogen pressure was 2.8MPa, and the space velocity (LHSV) was 3.5 hours -1 The petroleum fraction having the properties shown in Table 1 was mixed with methylcyclohexane at 10% by volume, hydrogenated, and the resulting oil was distilled and fractionated with methylcyclohexane to obtain a cycloalkane solvent. The analysis results of the obtained cycloalkane-based solvent are shown in Table 2.
Example 3
The continuous flow reaction apparatus was filled with 50ml of a catalyst (Ni 5256E, manufactured by N.E. CHEMCAT CORPORATION). Then, in the catalyst layer of the continuous flow reaction apparatus, the reaction temperature was 190℃and the hydrogen pressure was 2.8MPa, and the space velocity (LHSV) was 3.5 hours -1 The petroleum fraction having the properties shown in Table 1 was hydrogenated by mixing 10% by volume of the petroleum fraction with methylcyclohexane under the conditions of (a) and (b). After the initial consumption of the mixed raw oil, the obtained hydrogenated oil was mixed with petroleum fractions having the properties shown in table 1 as a diluent oil, and the mixture was fed to the hydrogenation apparatus in a recycle manner. Distilling the resulting oil with methylCyclohexane was fractionated to obtain a cycloalkane-based solvent. The analysis results of the obtained cycloalkane-based solvent are shown in Table 2.
Example 4
The continuous flow reaction apparatus was filled with 50ml of a catalyst (Ni 5256E, manufactured by N.E. CHEMCAT CORPORATION). Then, in the catalyst layer of the continuous flow reaction apparatus, the reaction temperature was 190℃and the hydrogen pressure was 2.8MPa, and the space velocity (LHSV) was 3.5 hours -1 The mixture of 10 vol% of the petroleum fraction having the properties shown in Table 1 and the cycloalkane solvent obtained in example 3 was passed through the reaction vessel and hydrogenated to obtain a cycloalkane solvent. The analysis results of the obtained cycloalkane-based solvent are shown in Table 2.
Method for measuring hansen solubility parameter and hansen sphere radius R
1ml of a solvent having a known HSP value was added to 1ml of a cycloalkane solvent, and the mixture was allowed to stand for 5 minutes. The affinity was then assessed visually. For the results of the affinity evaluation, hansen balls were determined using hansen ball method, and hansen solubility parameters and hansen ball radius R were calculated. The determination of the solubility in obtaining hansen balls was performed based on 25 ℃.
TABLE 1
TABLE 2
TABLE 3
| Example 1 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Hansen solubility parameter | ||||
| δd | 17.0 | 15.9 | 16.5 | 16.5 |
| δp | 5.9 | 5.3 | 3.7 | 5.0 |
| δh | 2.7 | 3.3 | 5.2 | 3.4 |
| δt | 18.2 | 17.1 | 17.7 | 17.6 |
| Hansen ball radius | 7.7 | 6.4 | 7.2 | 6.9 |
Claims (3)
1. A cycloalkane solvent which is a hydrogenated product of a petroleum fraction raw material or a distilled fraction of a light component or a heavy component of the hydrogenated product,
the content of hydrocarbon components having a boiling point of 190 to 310 ℃ is 90.0% by volume or more, the content of aromatic hydrocarbons is 1.0% by volume or less, the content of naphthenes having a 2-ring or more is 70.0% by volume or more, the flash point is 70.0 ℃ or more, and the aniline point is 48.0 to 75.0 ℃,
the petroleum fraction raw material is a petroleum fraction having a hydrocarbon component content of 90.0% by volume or more at a boiling point of 230 to 330 ℃, an aromatic hydrocarbon component content of 90.0% by mass or more at a carbon number of 11 to 18, an aromatic hydrocarbon component content of 70.0% by mass or more at a 2-ring or more, a hydrocarbon component content of 68.0% by mass or more at a carbon number of 14 to 18, and a hydrocarbon component content of 50.0% by volume or more at a boiling point of 250 ℃ or more.
2. The cycloalkane-based solvent according to claim 1, which satisfies the following formula (1):
145≤X+2Y≤160 (1)
in the formula (1), X represents an aniline point (. Degree. C.) and Y represents kauri-butanol value.
3. The cycloalkane-based solvent according to claim 1 or 2, wherein the hansen sphere radius R of hansen solubility parameter is 7.5 or more.
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