JP7618426B2 - Compounds and compositions - Google Patents

Description

The present invention relates to a novel compound and a composition containing the compound.

Ether alcohols obtained by reacting epoxyalkanes with polyhydric alcohols are useful as raw materials for emulsifiers, surfactants, dispersants, etc.

For example, Patent Document 1 discloses an ether alcohol obtained by reacting an epoxyalkane having 8 to 20 carbon atoms with a mono- or polyfunctional alcohol having 1 to 10 carbon atoms and 1 to 4 alcoholic hydroxyl groups.

In addition, Non-Patent Document 1 discloses hydroxyethers (monomers and dimers) obtained by reacting terminal epoxyalkanes having 8 to 16 carbon atoms with glycerol.

Japanese Unexamined Patent Publication No. 55-105632

SYNTHETIC COMMUNICATIONS, 24(21), 3009-3019 (1994)

However, it was found that the ether alcohols of Patent Document 1 and the hydroxyethers of Non-Patent Document 1 have high melting points and are therefore difficult to handle, and that the films formed by these ether alcohols and hydroxyethers have low hydrophobicity.

The present invention has been made in consideration of the above-mentioned circumstances, and provides a compound capable of forming a film having a low melting point and high hydrophobicity, and a composition containing the compound.

As a result of extensive research, the inventors have discovered that the above problems can be solved by using a compound with a specific structure.

That is, the present invention relates to a compound represented by the following chemical formula (1), chemical formula (2), or chemical formula (3).
(In the formula, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ¹¹ and R ¹² is 2 or more and 34 or less, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 2 or more and 34 or less.)
(In the formula, R ²¹ , R ²² , R ²³ and R ²⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ²¹ and R ²² is 2 or more and 34 or less, and the total number of carbon atoms of R ²³ and R ²⁴ is 2 or more and 34 or less.)
(In the formula, R ³¹ , R ³² , R ³³ and R ³⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ³¹ and R ³² is 2 or more and 34 or less, the total number of carbon atoms of R ³³ and R ³⁴ is 2 or more and 34 or less, and A ¹ and A ² are each independently a hydrogen atom, -CH ₂ -CH(OH)-CH ₂ OH, or -CH(-CH ₂ OH) _2. )

The compounds of the present invention represented by chemical formula (1), chemical formula (2) or chemical formula (3) (hereinafter, these compounds or mixtures of these compounds are referred to as ether alcohols) are characterized by a low melting point. This characteristic is believed to be due to the fact that the compounds have hydroxyl groups inside the carbon chain, and the carbon chain to which the hydroxyl groups are bonded has a branched structure, resulting in low molecular cohesion due to intermolecular repulsion caused by steric hindrance and uneven molecular arrangement. In addition, the ether alcohols of the present invention have excellent handling properties due to their low melting point, and also have excellent hydrophobic film forming properties.

The present invention will be described in detail below.

<Ether alcohol>
The ether alcohol of the present invention is a compound represented by the following chemical formula (1), chemical formula (2) or chemical formula (3), or a mixture of these compounds.
(In the formula, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ¹¹ and R ¹² is 2 or more and 34 or less, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 2 or more and 34 or less.)
(In the formula, R ²¹ , R ²² , R ²³ and R ²⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ²¹ and R ²² is 2 or more and 34 or less, and the total number of carbon atoms of R ²³ and R ²⁴ is 2 or more and 34 or less.)
(In the formula, R ³¹ , R ³² , R ³³ and R ³⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ³¹ and R ³² is 2 or more and 34 or less, the total number of carbon atoms of R ³³ and R ³⁴ is 2 or more and 34 or less, and A ¹ and A ² are each independently a hydrogen atom, -CH ₂ -CH(OH)-CH ₂ OH, or -CH(-CH ₂ OH) _2. )

R ¹¹ , R ¹² , R ¹³ and R ¹⁴ in the chemical formula (1), R ²¹ , R ²² , R ²³ and R ²⁴ in the chemical formula (2), and R ³¹ , R ³² , R ³³ and R ³⁴ in the chemical formula (3) are aliphatic hydrocarbon groups, and from the viewpoint of production efficiency and ease of production, are preferably linear or branched alkyl groups, more preferably linear alkyl groups, and even more preferably primary linear alkyl groups. The carbon numbers of the R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ³¹ , R ³² , R ³³ and R ³⁴ are each independently 1 to 33 and may have a distribution. R ¹¹ , R ¹² , R ¹³ and R ¹⁴ in the chemical formula (1) may be the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups. The same applies to R ²¹ , R ²² , R ²³ and R ²⁴ in the chemical formula (2) and R ³¹ , R ³² , R ³³ and R ³⁴ in the chemical formula (3).

The total number of carbon atoms of R ¹¹ and R ¹² , and the total number of carbon atoms of R ¹³ and R ¹⁴ in the chemical formula (1) are each 2 to 34, and from the viewpoint of the formability of a hydrophobic film, they are preferably 8 or more, more preferably 10 or more, and from the viewpoints of a low melting point and handleability, they are preferably 18 or less, more preferably 16 or less.

In the chemical formula (1), R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each independently preferably an aliphatic hydrocarbon group having 2 or more carbon atoms, more preferably an aliphatic hydrocarbon group having 3 or more carbon atoms, even more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms, and even more preferably an aliphatic hydrocarbon group having 5 or more carbon atoms, from the viewpoints of hydrophobic film formability, low melting point and handleability.

When the compound represented by the chemical formula (1) contains two or more compounds in which the carbon numbers of R ¹¹ and R ¹² and/or the carbon numbers of R ¹³ and R ¹⁴ are different, from the viewpoint of hydrophobic film formability, low melting point and handleability, the content ratio of the compound in which R ¹¹ has 5 or more carbon atoms and R ¹² has 5 or more carbon atoms, or the compound in which R ¹³ has 5 or more carbon atoms and R ¹⁴ has 5 or more carbon atoms, relative to the entire compound represented by the chemical formula (1), is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass or less.

The total number of carbon atoms of R ²¹ and R ²² , and the total number of carbon atoms of R ²³ and R ²⁴ in the chemical formula (2) are each 2 to 34, and from the viewpoint of the formability of a hydrophobic film, they are preferably 8 or more, more preferably 10 or more, and from the viewpoints of a low melting point and handleability, they are preferably 18 or less, more preferably 16 or less.

In the chemical formula (2), R ²¹ , R ²² , R ²³ and R ²⁴ are each independently preferably an aliphatic hydrocarbon group having 2 or more carbon atoms, more preferably an aliphatic hydrocarbon group having 3 or more carbon atoms, even more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms, and even more preferably an aliphatic hydrocarbon group having 5 or more carbon atoms, from the viewpoints of hydrophobic film formability, low melting point and handleability.

When the compound represented by the chemical formula (2) contains two or more compounds in which the carbon numbers of R ²¹ and R ²² and/or the carbon numbers of R ²³ and R ²⁴ are different, from the viewpoint of hydrophobic film formability, low melting point and handleability, the content ratio of the compound in which R ²¹ has 5 or more carbon atoms and R ²² has 5 or more carbon atoms, or the compound in which R ²³ has 5 or more carbon atoms and R ²⁴ has 5 or more carbon atoms, relative to the entire compound represented by the chemical formula (2), is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass or less.

The total number of carbon atoms of R ³¹ and R ³² , and the total number of carbon atoms of R ³³ and R ³⁴ in the chemical formula (3) are each 2 to 34, and from the viewpoint of the formability of a hydrophobic film, they are preferably 8 or more, more preferably 10 or more, and from the viewpoints of a low melting point and handleability, they are preferably 18 or less, more preferably 16 or less.

In the chemical formula (3), R ³¹ , R ³² , R ³³ and R ³⁴ are each independently preferably an aliphatic hydrocarbon group having 2 or more carbon atoms, more preferably an aliphatic hydrocarbon group having 3 or more carbon atoms, even more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms, and even more preferably an aliphatic hydrocarbon group having 5 or more carbon atoms, from the viewpoints of hydrophobic film formability, low melting point and handleability.

When the compound represented by the chemical formula (3) contains two or more compounds in which the carbon numbers of R ³¹ and R ³² and/or the carbon numbers of R ³³ and R ³⁴ are different, from the viewpoints of hydrophobic film formability, low melting point and handleability, the content ratio of the compound in which R ³¹ has 5 or more carbon atoms and R ³² has 5 or more carbon atoms, or the compound in which R ³³ has 5 or more carbon atoms and R ³⁴ has 5 or more carbon atoms, relative to the entire compound represented by the chemical formula (3), is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less.

In the chemical formula (3), A ¹ and A ² are each independently a hydrogen atom, -CH ₂ -CH(OH)-CH ₂ OH, or -CH(-CH ₂ OH) ₂ , and from the viewpoint of the formability of a hydrophobic film, -CH ₂ -CH(OH)-CH ₂ OH or -CH(-CH ₂ OH) ₂ is preferable.

From the viewpoint of ease of handling and solubility in organic solvents, the melting point of the ether alcohol is preferably 30°C or lower, more preferably 20°C or lower, even more preferably 10°C or lower, and even more preferably 5°C or lower, and may be -200°C or higher.

The method for producing the ether alcohol is not particularly limited, and for example, the ether alcohol can be produced by synthesizing an internal epoxide by oxidizing a double bond of an internal olefin with a peroxide such as hydrogen peroxide or peracetic acid, reacting the obtained internal epoxide with glycerin, and further reacting the obtained internal epoxide with a glycerin ring-opened product of the internal epoxide, or by dehydrating and condensing the obtained glycerin ring-opened product of the internal epoxide. The ether alcohol obtained by the above production method is usually a mixture containing a compound represented by the chemical formula (1), a compound represented by the chemical formula (2), and a compound represented by the chemical formula (3) (a compound in which ^A1 and ^A2 are each independently _-CH2 -CH(OH) _-CH2OH , or -CH( _-CH2OH ) ₂ ). In the case of the production method, the compound represented by the chemical formula (1) usually includes two or more compounds in which the number of carbon atoms in R ¹¹ and R ¹² and/or the number of carbon atoms in R ¹³ and R ¹⁴ are different, the compound represented by the chemical formula (2) includes two or more compounds in which the number of carbon atoms in R ²¹ and R ²² and/or the number of carbon atoms in R ²³ and R ²⁴ are different, and the compound represented by the chemical formula (3) includes two or more compounds in which the number of carbon atoms in R ³¹ and R ³² and/or the number of carbon atoms in R ³³ and R ³⁴ are different. In the case of the above-mentioned production method, the compound represented by the chemical formula (3) is usually a mixture of a compound in which A ¹ and A ² are -CH ₂ -CH(OH)-CH ₂ ^OH , a compound in which A ¹ and A ² are -CH(-CH ₂ OH) ₂ , and a compound in which one of A ¹ and A 2 is -CH ₂ -CH(OH)-CH ₂ OH and the other is -CH(-CH ₂ OH) _2. In the compound represented by the chemical formula (3), a compound in which A ¹ or A ² is a hydrogen atom can be produced by dehydrating and condensing a glycerin ring-opened product obtained by reacting glycerin with the internal epoxide, and a water ring-opened product obtained by reacting water with the internal epoxide. In the compound represented by the chemical formula (3), a compound in which A ¹ and A ² are hydrogen atoms can be produced by dehydrating and condensing a water ring-opened product obtained by reacting water with the internal epoxide.

The olefin used in the production of the ether alcohol may contain terminal olefins in addition to internal olefins. In such cases, the content of terminal olefins in the olefin is, for example, 0.1% by mass or more, 0.2% by mass or more, and 5% by mass or less, 3% by mass or less, 2% by mass or less, 1% by mass or less, 0.5% by mass or less, etc.

The ether alcohol may be one type of compound represented by the chemical formula (1), one type of compound represented by the chemical formula (2), or one type of compound represented by the chemical formula (3). The ether alcohol may be a mixture of two or more types of compounds represented by the chemical formula (1), a mixture of two or more types of compounds represented by the chemical formula (2), or a mixture of two or more types of compounds represented by the chemical formula (3). The ether alcohol may be a mixture containing one or more types of compounds represented by the chemical formula (1) and one or more types of compounds represented by the chemical formula (2), a mixture containing one or more types of compounds represented by the chemical formula (1) and one or more types of compounds represented by the chemical formula (3), or a mixture containing one or more types of compounds represented by the chemical formula (2) and one or more types of compounds represented by the chemical formula (3). The ether alcohol may be a mixture containing one or more types of compounds represented by the chemical formulas (1) to (3).

The ether alcohol may be a surfactant, an emulsifier, a dispersant, a raw material for polymers and resins, an additive for oils such as lubricating oils, a paint additive, an agricultural chemical additive, a resin additive, a metal surface modifier, a cosmetic base material, a medical auxiliary, a textile oil, a petroleum agent, a processing agent, a lubricant, a plasticizer, an emulsifier, a dispersant, an anti-fogging agent, an antistatic agent, an antifoaming agent, a wetting agent, a penetrating agent, an oil recovery agent, a cleaning agent, or a rust inhibitor. The oil recovery agent is preferably an agent for crude oil recovery, more preferably an agent for Enhanced Oil Recovery (hereinafter the same), and even more preferably an agent for chemical EOR.

<Composition>
The composition of the present invention contains at least the ether alcohol.

The total content of the ether alcohol in the composition is not particularly limited, but from the viewpoint of reducing transportation and storage costs, it is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 100% by mass.

The composition of the present invention may be a surfactant composition, an emulsifier composition, a dispersant composition, a paint additive composition, an agricultural chemical additive composition, a resin additive composition, a metal surface modifier composition, a cosmetic base material composition, a medical auxiliary composition, a textile oil composition, a petroleum chemical composition, a processing chemical composition, a lubricant composition, a plasticizer composition, an antifogging agent composition, an antistatic agent composition, a defoamer composition, a wetting agent composition, a penetrant composition, an oil recovery composition, a detergent composition, an oil agent composition, or a rust inhibitor composition. The oil recovery composition is preferably a crude oil recovery composition, more preferably an EOR composition, and even more preferably a chemical EOR composition.

The composition may contain solvents and additives that are appropriately added depending on the application from the viewpoints of ease of handling, storage stability, etc.

The present invention and preferred embodiments thereof are described below.
＜1＞
A compound represented by the following chemical formula (1), chemical formula (2) or chemical formula (3).
(In the formula, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ¹¹ and R ¹² is 2 or more and 34 or less, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 2 or more and 34 or less.)
(In the formula, R ²¹ , R ²² , R ²³ and R ²⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ²¹ and R ²² is 2 or more and 34 or less, and the total number of carbon atoms of R ²³ and R ²⁴ is 2 or more and 34 or less.)
(In the formula, R ³¹ , R ³² , R ³³ and R ³⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ³¹ and R ³² is 2 or more and 34 or less, the total number of carbon atoms of R ³³ and R ³⁴ is 2 or more and 34 or less, and A ¹ and A ² are each independently a hydrogen atom, -CH ₂ -CH(OH)-CH ₂ OH, or -CH(-CH ₂ OH) _2. )
＜2＞
The compound according to <1>, wherein the aliphatic hydrocarbon group is preferably a linear or branched alkyl group, more preferably a linear alkyl group, and even more preferably a primary linear alkyl group.
＜3＞
The compound according to <1> or <2>, wherein R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ³¹ , R ³² , R ³³ and R ³⁴ each independently have 1 to 33 carbon atoms.
＜4＞
The compound according to any one of <1> to <3>, wherein R ¹¹ , R ¹² , R ¹³ and R ¹⁴ in the chemical formula (1) are the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.
＜5＞
The compound according to any one of <1> to <4>, wherein R ²¹ , R ²² , R ²³ and R ²⁴ in the chemical formula (2) are the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.
＜6＞
The compound according to any one of <1> to <5>, wherein R ³¹ , R ³² , R ³³ and R ³⁴ in the chemical formula (3) are the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.
＜７＞
The compound according to any one of <1> to <6>, wherein the total number of carbon atoms of R ¹¹ and R ¹² and/or the total number of carbon atoms of R ¹³ and R ¹⁴ in the chemical formula (1) is preferably 8 or more, more preferably 10 or more, and is preferably 18 or less, more preferably 16 or less.
＜8＞
The compound according to any one of <1> to <6>, wherein the total number of carbon atoms of R ¹¹ and R ¹² and/or the total number of carbon atoms of R ¹³ and R ¹⁴ in the chemical formula (1) is 8 or more and 18 or less.
＜9＞
The compound according to any one of <1> to <6>, wherein the total number of carbon atoms of R ¹¹ and R ¹² and/or the total number of carbon atoms of R ¹³ and R ¹⁴ in the chemical formula (1) is 10 or more and 16 or less.
＜10＞
The compound according to any one of <1> to <9>, wherein R ¹¹ , R ¹² , R ¹³ and R ¹⁴ in the chemical formula (1) are each independently preferably an aliphatic hydrocarbon group having 2 or more carbon atoms, more preferably an aliphatic hydrocarbon group having 3 or more carbon atoms, even more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms, and even more preferably an aliphatic hydrocarbon group having 5 or more carbon atoms.
<11>
When the compound represented by the chemical formula (1) includes two or more compounds in which R ¹¹ and R ¹² have different carbon numbers and/or R ¹³ and R ¹⁴ have different carbon numbers, the content of the compound in which R ¹¹ has 5 or more carbon atoms and R ¹² has 5 or more carbon atoms, or the content of the compound in which R ¹³ has 5 or more carbon atoms and R ¹⁴ has 5 or more carbon atoms is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less, relative to the entire compound represented by the chemical formula (1). The compound according to any one of <1> to <10>.
＜12＞
The compound according to any one of <1> to <10>, wherein when the compound represented by the chemical formula (1) contains two or more compounds in which R ¹¹ and R ¹² have different carbon numbers and/or R ¹³ and R ¹⁴ have different carbon numbers, the content of the compound in which R ¹¹ has 5 or more carbon atoms and R ¹² has 5 or more carbon atoms, or the content of the compound in which R ¹³ has 5 or more carbon atoms and R ¹⁴ has 5 or more carbon atoms is 10 mass% or more and 90 mass% or less with respect to the entire compound represented by the chemical formula (1).
＜13＞
The compound according to any one of <1> to <10>, wherein when the compound represented by the chemical formula (1) contains two or more compounds in which R ¹¹ and R ¹² have different carbon numbers and/or R ¹³ and R ¹⁴ have different carbon numbers, the content of the compound in which R ¹¹ has 5 or more carbon atoms and R ¹² has 5 or more carbon atoms, or the content of the compound in which R ¹³ has 5 or more carbon atoms and R ¹⁴ has 5 or more carbon atoms is 20 mass% or more and 80 mass% or less with respect to the entire compound represented by the chemical formula (1).
＜14＞
The compound according to any one of <1> to <10>, wherein when the compound represented by the chemical formula (1) contains two or more compounds in which R ¹¹ and R ¹² have different carbon numbers and/or R ¹³ and R ¹⁴ have different carbon numbers, the content of the compound in which R ¹¹ has 5 or more carbon atoms and R ¹² has 5 or more carbon atoms, or the content of the compound in which R ¹³ has 5 or more carbon atoms and R ¹⁴ has 5 or more carbon atoms is 30 mass% or more and 70 mass% or less with respect to the entire compound represented by the chemical formula (1).
＜15＞
The compound according to any one of <1> to <14>, wherein the total number of carbon atoms of R ²¹ and R ²² and/or the total number of carbon atoms of R ²³ and R ²⁴ in the chemical formula (2) is preferably 8 or more, more preferably 10 or more, and is preferably 18 or less, more preferably 16 or less.
＜16＞
The compound according to any one of <1> to <14>, wherein the total number of carbon atoms of R ²¹ and R ²² and/or the total number of carbon atoms of R ²³ and R ²⁴ in the chemical formula (2) is 8 or more and 18 or less.
＜１７＞
The compound according to any one of <1> to <14>, wherein the total number of carbon atoms of R ²¹ and R ²² and/or the total number of carbon atoms of R ²³ and R ²⁴ in the chemical formula (2) is 10 or more and 16 or less.
＜18＞
The compound according to any one of <1> to <17>, wherein R ²¹ , R ²² , R ²³ and R ²⁴ in the chemical formula (2) are each independently preferably an aliphatic hydrocarbon group having 2 or more carbon atoms, more preferably an aliphatic hydrocarbon group having 3 or more carbon atoms, even more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms, and even more preferably an aliphatic hydrocarbon group having 5 or more carbon atoms.
＜19＞
When the compound represented by the chemical formula (2) includes two or more compounds in which R ²¹ and R ²² have different carbon numbers and/or R ²³ and R ²⁴ have different carbon numbers, the content of the compound in which R ²¹ has 5 or more carbon atoms and R ²² has 5 or more carbon atoms, or the content of the compound in which R ²³ has 5 or more carbon atoms and R ²⁴ has 5 or more carbon atoms, relative to the entire compound represented by the chemical formula (2), is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less. The compound according to any one of <1> to <18>.
＜20＞
The compound according to any one of <1> to <18>, wherein, when the compound represented by the chemical formula (2) includes two or more compounds in which R ²¹ and R ²² have different carbon numbers and/or R ²³ and R ²⁴ have different carbon numbers, the content of the compound in which R ²¹ has 5 or more carbon atoms and R ²² has 5 or more carbon atoms, or the content of the compound in which R ²³ has 5 or more carbon atoms and R ²⁴ has 5 or more carbon atoms is 10 mass% or more and 90 mass% or less with respect to the entire compound represented by the chemical formula (2).
＜21＞
The compound according to any one of <1> to <18>, wherein when the compound represented by the chemical formula (2) includes two or more compounds in which R ²¹ and R ²² have different carbon numbers and/or R ²³ and R ²⁴ have different carbon numbers, the content of the compound in which R ²¹ has 5 or more carbon atoms and R ²² has 5 or more carbon atoms, or the content of the compound in which R ²³ has 5 or more carbon atoms and R ²⁴ has 5 or more carbon atoms is 20 mass% or more and 80 mass% or less with respect to the entire compound represented by the chemical formula (2).
＜22＞
The compound according to any one of <1> to <18>, wherein, when the compound represented by the chemical formula (2) includes two or more compounds in which R ²¹ and R ²² have different carbon numbers and/or R ²³ and R ²⁴ have different carbon numbers, the content of the compound in which R ²¹ has 5 or more carbon atoms and R ²² has 5 or more carbon atoms, or the content of the compound in which R ²³ has 5 or more carbon atoms and R ²⁴ has 5 or more carbon atoms is 30 mass% or more and 70 mass% or less with respect to the entire compound represented by the chemical formula (2).
＜23＞
The compound according to any one of <1> to <22>, wherein the total number of carbon atoms of R ³¹ and R ³² and/or the total number of carbon atoms of R ³³ and R ³⁴ in the chemical formula (3) is preferably 8 or more, more preferably 10 or more, and is preferably 18 or less, more preferably 16 or less.
＜24＞
The compound according to any one of <1> to <22>, wherein the total number of carbon atoms of R ³¹ and R ³² and/or the total number of carbon atoms of R ³³ and R ³⁴ in the chemical formula (3) is 8 or more and 18 or less.
＜25＞
The compound according to any one of <1> to <22>, wherein the total number of carbon atoms of R ³¹ and R ³² and/or the total number of carbon atoms of R ³³ and R ³⁴ in the chemical formula (3) is 10 or more and 16 or less.
＜26＞
The compound according to any one of <1> to <25>, wherein R ³¹ , R ³² , R ³³ and R ³⁴ in the chemical formula (3) are each independently preferably an aliphatic hydrocarbon group having 2 or more carbon atoms, more preferably an aliphatic hydrocarbon group having 3 or more carbon atoms, even more preferably an aliphatic hydrocarbon group having 4 or more carbon atoms, and even more preferably an aliphatic hydrocarbon group having 5 or more carbon atoms.
＜27＞
The compound according to any one of <1> to <26>, wherein when the compound represented by the chemical formula (3) includes two or more compounds in which R ³¹ and R ³² have different carbon numbers and/or R ³³ and R ³⁴ have different carbon numbers, the content of the compound in which R ³¹ has 5 or more carbon atoms and R ³² has 5 or more carbon atoms, or the content of the compound in which R ³³ has 5 or more carbon atoms and R ³⁴ has 5 or more carbon atoms, relative to the entire compound represented by the chemical formula (3), is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more, and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less.
＜28＞
The compound according to any one of <1> to <26>, wherein when the compound represented by the chemical formula (3) includes two or more compounds in which R ³¹ and R ³² have different carbon numbers and/or R ³³ and R ³⁴ have different carbon numbers, the content of the compound in which R ³¹ has 5 or more carbon atoms and R ³² has 5 or more carbon atoms, or the content of the compound in which R ³³ has 5 or more carbon atoms and R ³⁴ has 5 or more carbon atoms is 10 mass% or more and 90 mass% or less with respect to the entire compound represented by the chemical formula (3).
＜29＞
The compound according to any one of <1> to <26>, wherein when the compound represented by the chemical formula (3) includes two or more compounds in which R ³¹ and R ³² have different carbon numbers and/or R ³³ and R ³⁴ have different carbon numbers, the content of the compound in which R ³¹ has 5 or more carbon atoms and R ³² has 5 or more carbon atoms, or the content of the compound in which R ³³ has 5 or more carbon atoms and R ³⁴ has 5 or more carbon atoms is 20 mass% or more and 80 mass% or less with respect to the entire compound represented by the chemical formula (3).
＜30＞
The compound according to any one of <1> to <26>, wherein when the compound represented by the chemical formula (3) includes two or more compounds in which R ³¹ and R ³² have different carbon numbers and/or R ³³ and R ³⁴ have different carbon numbers, the content of the compound in which R ³¹ has 5 or more carbon atoms and R ³² has 5 or more carbon atoms, or the content of the compound in which R ³³ has 5 or more carbon atoms and R ³⁴ has 5 or more carbon atoms is 30 mass% or more and 70 mass% or less with respect to the entire compound represented by the chemical formula (3).
＜31＞
The compound according to any one of <1> to <30>, wherein A ¹ and A ² in the chemical formula (3) are each independently —CH ₂ —CH(OH)—CH ₂ OH or —CH(—CH ₂ OH) ₂ .
＜32＞
The compound represented by the chemical formula (1) has a melting point of preferably 30° C. or lower, more preferably 20° C. or lower, even more preferably 10° C. or lower, still more preferably 5° C. or lower, and is −200° C. or higher. The compound according to any one of <1> to <31>.
＜33＞
The compound represented by the chemical formula (2) has a melting point of preferably 30° C. or lower, more preferably 20° C. or lower, even more preferably 10° C. or lower, still more preferably 5° C. or lower, and is −200° C. or higher. The compound according to any one of <1> to <32>.
＜34＞
The compound represented by the chemical formula (3) has a melting point of preferably 30° C. or lower, more preferably 20° C. or lower, even more preferably 10° C. or lower, still more preferably 5° C. or lower, and is −200° C. or higher. The compound according to any one of <1> to <33>.
＜35＞
The compound according to any one of <1> to <34>, wherein the compound is a surfactant, an emulsifier, a wetting agent, a penetrating agent, an agent for oil recovery, a cleaning agent, an oil additive, or a rust inhibitor.
＜36＞
The compound according to <35>, wherein the oil recovery agent is preferably an agent for crude oil recovery, more preferably an agent for EOR (Enhanced Oil Recovery, hereinafter the same), and even more preferably an agent for chemical EOR.
＜３７＞
A composition comprising at least one compound according to any one of <1> to <36>.
＜３８＞
The composition according to <37>, wherein the composition contains two or more compounds represented by the chemical formula (1).
＜３９＞
The composition according to <37>, wherein the composition contains two or more compounds represented by the chemical formula (2).
＜40＞
The composition according to <37>, wherein the composition contains two or more compounds represented by the chemical formula (3).
＜41＞
The composition according to <37>, comprising at least one compound represented by the chemical formula (1) and at least one compound represented by the chemical formula (2).
＜42＞
The composition according to <37>, comprising at least one compound represented by the chemical formula (1) and at least one compound represented by the chemical formula (3).
＜43＞
The composition according to <37>, comprising at least one compound represented by the chemical formula (2) and at least one compound represented by the chemical formula (3).
＜44＞
The composition according to <37>, comprising at least one of the compound represented by the chemical formula (1), the compound represented by the chemical formula (2), and the compound represented by the chemical formula (3).
＜45＞
The composition according to any of <37> to <44>, wherein the total content of the compound in the composition is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, still more preferably 80% by mass or more, and still more preferably 100% by mass.
＜46＞
The composition according to any one of <37> to <45>, which is a surfactant composition, an emulsifier composition, a wetting agent composition, a penetrant composition, an oil recovery composition, a detergent composition, an oil composition, or a rust inhibitor composition.
＜47＞
The composition for oil recovery is preferably a composition for crude oil recovery, more preferably a composition for EOR, and even more preferably a composition for chemical EOR.

The present invention will be specifically described below based on examples. Unless otherwise specified in the table, the content (%) of each component indicates mass % and the ratio (/) indicates mass ratio. The various measurement methods are as follows.

<Method for measuring the double bond distribution of olefin>
The double bond distribution of the olefin was measured by gas chromatography (hereinafter abbreviated as GC). Specifically, the olefin was reacted with dimethyl disulfide to form a dithiolated derivative, and each component was then separated by GC. The double bond distribution of the olefin was determined from each peak area. The apparatus and analytical conditions used for the measurement are as follows:
GC device: Product name HP6890 (manufactured by Hewlett Packard)
Column: Product name: Ultra-Alloy-1HT capillary column 30 m x 250 μm x 0.15 μm (manufactured by Frontier Labs, Inc.)
Detector: Flame ionization detector (FID)
Injection temperature: 300°C
Detector temperature: 350°C
Oven: 60°C (0 min.) → 2°C/min. → 225°C → 20°C/min. → 350°C → 350°C (5.2 min.)

<Method for measuring the content ratio of structural isomers of alkyl glyceryl ether>
The ratio of structural isomers of alkyl glyceryl ether (a primary hydroxyl group adduct of glycerin and a secondary hydroxyl group adduct of glycerin) was measured by ¹ H-NMR. Specifically, 0.05 g of alkyl glyceryl ether, 0.2 g of trifluoroacetic anhydride, and 1 g of deuterated chloroform were mixed and measured by ¹ H-NMR. The measurement conditions were as follows:
Nuclear magnetic resonance apparatus: Agilent 400-MR DD2, manufactured by Agilent Technologies, Inc. Observation range: 6410.3 Hz
Data points: 65536
Measurement mode: Presat
Pulse width: 45°
Pulse delay time: 10 sec
Number of times accumulated: 128

<Method for measuring dialkyl glyceryl ether>
Dialkyl glyceryl ether was measured by high performance liquid chromatography (hereinafter abbreviated as HPLC). Specifically, 0.1 g of dialkyl glyceryl ether was mixed with 1 g of methanol and separated by LC. The purity of the dialkyl glyceryl ether was determined from the peak area. The measurement conditions were as follows.
HPLC device: Product name DIONEX Ultimate 3000
Column: L-column ODS, 5 μm, Cat. No. 622070, Size 4.6 × 150 mm
Mobile phase: 10 mM ammonium acetate in methanol Flow rate: 1 mL/min
Oven temperature: 40°C
Detector: Charged Aerosol Detector (CAD)

<Calculation method for each component in dialkyl glyceryl ether>
The ratio of each component in the dialkyl glyceryl ether was calculated from the ratio of the alkyl glyceryl ether to the diol and the content ratio of the structural isomers of the alkyl glyceryl ether. The reaction selectivity of the primary hydroxyl group and the secondary hydroxyl group was calculated as 75/25. Specifically, the calculation was performed as follows.
Chemical formula (1) = (proportion of alkyl glyceryl ether (%)) x (primary hydroxyl group adduct of glycerin (%)) x 0.6
Chemical formula (2) = ((percentage of alkyl glyceryl ether (%)) x (primary hydroxyl group adduct of glycerin (%)) x 0.2) + ((percentage of alkyl glyceryl ether (%)) x (percentage of secondary hydroxyl group of glycerin (%)) x 0.8)
Chemical formula (3) = ((percentage of alkyl glyceryl ether (%)) x (primary hydroxyl group adduct of glycerin (%)) x 0.2) + ((percentage of alkyl glyceryl ether (%)) x (secondary hydroxyl group adduct of glycerin (%)) x 0.2) + (percentage of diol (%))

<Production of Internal Olefins>
Manufacturing Example A1
(Production of Internal Olefin Having 16 Carbon Atoms (Internal Olefin 1))
7000g (28.9 moles) of 1-hexadecanol (product name: Kalcol 6098, manufactured by Kao Corporation) and 700g (10wt% based on the raw material alcohol) of γ-alumina (STREM Chemicals, Inc.) as a solid acid catalyst were charged into a flask equipped with a stirrer, and the reaction was carried out for 32 hours at 280°C while circulating nitrogen (7000mL/min) through the system under stirring. After completion of the reaction, the alcohol conversion rate was 100% and the C16 olefin purity was 99.6%. The obtained crude C16 internal olefin was transferred to a distiller and distilled at 136-160°C/4.0mmHg to obtain internal olefin 1 with an olefin purity of 100%. The double bond distribution of the obtained internal olefin 1 was 0.2% at C1, 15.8% at C2, 14.5% at C3, 15.7% at C4, 17.3% at C5, 16.5% at C6, and 20.0% in total at C7 and C8.

Manufacturing Example A2
(Production of Internal Olefin Having 18 Carbon Atoms (Internal Olefin 2))
A reactor equipped with a stirrer was charged with 800 kg (3.0 kmol) of 1-octadecanol (product name: Kalcol 8098, manufactured by Kao Corporation) and 80 kg (10 wt % based on the raw material alcohol) of activated alumina GP-20 (Mizusawa Chemical Industry Co., Ltd.) as a solid acid catalyst, and the reaction was carried out for 16 hours at 280°C while circulating nitrogen (15 L/min) through the system under stirring. After completion of the reaction, the alcohol conversion rate was 100%, and the C18 olefin purity was 98.7%. The obtained crude C18 internal olefin was transferred to a distiller and distilled at 163-190°C/4.6 mmHg to obtain internal olefin 2 with an olefin purity of 100%. The double bond distribution of the obtained internal olefin 2 was 0.3% at C1, 13.3% at C2, 12.6% at C3, 13.9% at C4, 14.8% at C5, 13.7% at C6, 12.6% at C7, and 18.8% in total at C8 and C9.

Manufacturing Example A3
(Production of Internal Olefin Having 14 Carbon Atoms (Internal Olefin 3))
Internal olefin 3 was obtained by the same production method as in Production Example A1, except that 28.9 mol of 1-tetradecanol (product name: Kalcol 4098, manufactured by Kao Corporation) was used instead of 28.9 mol of 1-hexadecanol (product name: Kalcol 6098, manufactured by Kao Corporation) in Production Example A1. The double bond distribution of the obtained internal olefin 3 was 0.2% at C1, 22.4% at C2, 19.5% at C3, 20.3% at C4, 16.5% at C5, and 21.1% in total at C6 and C7.

Manufacturing example A4
(Production of Internal Olefin Having 12 Carbon Atoms (Internal Olefin 4))
Internal olefin 4 was obtained by the same production method as in Production Example A1, except that 28.9 mol of 1-dodecanol (product name: Kalcol 2098, manufactured by Kao Corporation) was used instead of 28.9 mol of 1-hexadecanol (product name: Kalcol 6098, manufactured by Kao Corporation) in Production Example A1. The double bond distribution of the obtained internal olefin 4 was 0.1% at C1, 25.0% at C2, 22.5% at C3, 22.9% at C4, and 29.5% in total at C5 and C6.

Preparation of Internal Epoxide
Manufacturing Example B1
(Production of Internal Epoxide Having 16 Carbon Atoms (Internal Epoxide 1))
A flask equipped with a stirrer was charged with the internal olefin 1 (800 g, 3.56 mol) obtained in Production Example A1, 107 g (1.78 mol) of acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.), 15.6 g (0.15 mol) of sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd.), 415.7 g (4.28 mol) of 35% hydrogen peroxide (manufactured by Wako Pure Chemical Industries, Ltd.), and 25.3 g (0.18 mol) of sodium sulfate (manufactured by Wako Pure Chemical Industries, Ltd.), and reacted at 50 ° C. for 4 hours. Then, the temperature was raised to 70 ° C. and the reaction was continued for another 2 hours. After the reaction, the mixture was separated and the aqueous layer was extracted, and the oil layer was washed with ion-exchanged water, a saturated aqueous sodium carbonate solution (manufactured by Wako Pure Chemical Industries, Ltd.), a saturated aqueous sodium sulfite solution (manufactured by Wako Pure Chemical Industries, Ltd.), and 1% saline solution (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated with an evaporator to obtain 820 g of internal epoxide 1.

Manufacturing Example B2
(Production of Internal Epoxide Having 18 Carbon Atoms (Internal Epoxide 2))
In a flask equipped with a stirrer, the internal olefin 2 (595 g, 2.38 mol) obtained in Production Example A2, 71.7 g (1.20 mol) of acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.), 9.8 g (0.10 mol) of sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd.), and 324 g (4.00 mol) of 35% hydrogen peroxide (manufactured by Wako Pure Chemical Industries, Ltd.) were charged and reacted at 50 ° C. for 4 hours. Then, the temperature was raised to 80 ° C. and the reaction was continued for another 5 hours. After the reaction, the mixture was separated and the aqueous layer was extracted, and the oil layer was washed with ion-exchanged water, a saturated aqueous sodium carbonate solution (manufactured by Wako Pure Chemical Industries, Ltd.), a saturated aqueous sodium sulfite solution (manufactured by Wako Pure Chemical Industries, Ltd.), and ion-exchanged water, and concentrated with an evaporator to obtain 629 g of internal epoxide 2.

Manufacturing Example B3
(Production of Internal Epoxide Having 14 Carbon Atoms (Internal Epoxide 3))
An internal epoxide 3 was obtained in the same manner as in Production Example B1, except that the internal olefin 3 (3.56 mol) obtained in Production Example A3 was used instead of the internal olefin 1 (3.56 mol) obtained in Production Example A1.

Manufacturing Example B4
(Production of Internal Epoxide Having 12 Carbon Atoms (Internal Epoxide 4))
Internal epoxide 4 was obtained in the same manner as in Production Example B1, except that the internal olefin 1 (3.56 mol) obtained in Production Example A1 was replaced with the internal olefin 4 (3.56 mol) obtained in Production Example A4.

<Production of reaction product of epoxide and glycerin (alkyl glyceryl ether, AGE)>
Hereinafter, alkyl glyceryl ether will be referred to as AGE. Furthermore, AGE1, AGE2, AGE3, AGE4, AGE5, AGE6, AGE7, etc. respectively represent alkyl glyceryl ether 1, alkyl glyceryl ether 2, alkyl glyceryl ether 3, alkyl glyceryl ether 4, alkyl glyceryl ether 5, alkyl glyceryl ether 6, alkyl glyceryl ether 7, etc.

Manufacturing Example C1
(Preparation of reaction product of internal epoxide 1 and glycerin (AGE1))
In a flask equipped with a stirrer, 2298 g (25.0 mol) of glycerin (manufactured by Wako Pure Chemical Industries, Ltd.) and 0.122 g (1.25 mmol) of 98% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd.) were charged and heated to 130° C. Then, the internal epoxide 1 (300 g, 1.25 mol) obtained in Production Example B1 was added dropwise over 1 hour, and the reaction was carried out at 130° C. for 8 hours. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water, and then concentrated under reduced pressure using an evaporator to obtain 400 g of AGE1. The ratio of alkyl glyceryl ether and diol in the obtained AGE1 was alkyl glyceryl ether/diol=96/4. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE1 was primary hydroxyl group adduct/secondary hydroxyl group adduct=73/27.

Manufacturing Example C2
(Preparation of reaction product of internal epoxide 2 and glycerin (AGE2))
AGE2 was obtained by the same production method as in Production Example C1, except that the internal epoxide 2 (1.25 mol) obtained in Production Example B2 was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. The ratio of alkyl glyceryl ether and diol in the obtained AGE2 was alkyl glyceryl ether/diol=95/5. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE2 was primary hydroxyl group adduct/secondary hydroxyl group adduct=74/26.

Manufacturing Example C3
(Preparation of reaction product of internal epoxide 3 and glycerin (AGE3))
AGE3 was obtained by the same production method as in Production Example C1, except that the internal epoxide 3 (1.25 mol) obtained in Production Example B3 was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. The ratio of alkyl glyceryl ether and diol in the obtained AGE3 was alkyl glyceryl ether/diol=93/7. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE3 was primary hydroxyl group adduct/secondary hydroxyl group adduct=74/26.

Manufacturing Example C4
(Preparation of reaction product of internal epoxide 4 and glycerin (AGE4))
AGE4 was obtained by the same production method as in Production Example C1, except that the internal epoxide 4 (1.25 mol) obtained in Production Example B4 was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. The ratio of alkyl glyceryl ether and diol in the obtained AGE4 was alkyl glyceryl ether/diol=90/10. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE4 was primary hydroxyl group adduct/secondary hydroxyl group adduct=76/24.

Manufacturing Example C5
(Preparation of reaction product of C14 terminal epoxide and glycerin (AGE5))
AGE5 was obtained by the same production method as in Production Example C1, except that 1.25 mol of C14 terminal epoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. The ratio of alkyl glyceryl ether and diol in the obtained AGE5 was alkyl glyceryl ether/diol=92/8. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE5 was primary hydroxyl group adduct/secondary hydroxyl group adduct=74/26.

Manufacturing Example C6
(Preparation of reaction product of C16 terminal epoxide and glycerin (AGE6))
AGE6 was obtained by the same production method as in Production Example C1, except that 1.25 mol of C16 terminal epoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. The ratio of alkyl glyceryl ether and diol in the obtained AGE6 was alkyl glyceryl ether/diol=95/5. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE6 was primary hydroxyl group adduct/secondary hydroxyl group adduct=76/23.

Manufacturing Example C7
(Preparation of reaction product of C18 terminal epoxide and glycerin (AGE7))
AGE7 was obtained by the same method as in Production Example C1, except that 1.25 mol of C18 terminal epoxide (Tokyo Chemical Industry Co., Ltd.) was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. The ratio of alkyl glyceryl ether and diol in the obtained AGE7 was alkyl glyceryl ether/diol=94/6. The ratio of primary hydroxyl group adduct of glycerin and secondary hydroxyl group adduct of glycerin in the obtained AGE7 was primary hydroxyl group adduct/secondary hydroxyl group adduct=73/27.

<Production of reaction product of alkyl glyceryl ether and epoxide (dialkyl glyceryl ether, DAGE)>
Hereinafter, dialkyl glyceryl ether will be referred to as DAGE. Furthermore, DAGE1, DAGE2, DAGE3, DAGE4, DAGE5, DAGE6, DAGE7, etc. respectively represent dialkyl glyceryl ether 1, dialkyl glyceryl ether 2, dialkyl glyceryl ether 3, dialkyl glyceryl ether 4, dialkyl glyceryl ether 5, dialkyl glyceryl ether 6, dialkyl glyceryl ether 7, etc.

Manufacturing Example D1
(Preparation of reaction product (DAGE1) of AGE1 and epoxide)
In a flask equipped with a stirrer, the internal epoxide 1 (300 g, 1.25 mol) obtained in Production Example B1, 0.122 g (1.25 mmol) of 98% sulfuric acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and AGE1 (400 g, 1.25 mol) obtained in Production Example C1 were charged and heated to 150° C. Then, a reaction was carried out at 150° C. for 5 hours. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water, followed by vacuum concentration using an evaporator to obtain 700 g of DAGE1. The obtained DAGE1 has the following chemical formula (1): R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each contain an alkyl group having 1 to 13 carbon atoms, the total number of carbon atoms of R ¹¹ and R ¹² is 14, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 14; R ²¹ , R ²² , R ²³ and R ²⁴ each contain an alkyl group having 1 to 13 carbon atoms, the total number of carbon atoms of R ²¹ and R ²² is 14, and the total number of carbon atoms of R ²³ and R ²⁴ is 14; R ³¹ , R ³² , R ³³ and R ³⁴ each contain an alkyl group having 1 to 13 carbon atoms, the total ^number of carbon atoms of _R ³¹ and R ³² is 14, and the total number of carbon atoms of R ³³ and R ³⁴ is 14 ^; The compound represented by the chemical formula ( ₁ ) was 42.0%, the compound represented by the chemical formula (2 ₎ was 34.8%, and the compound represented by the chemical formula (3) was 23.2% _.

Manufacturing Example D2
(Preparation of reaction product of AGE2 and epoxide (DAGE2))
DAEG2 was obtained by the same production method as in Production Example D1, except that the internal epoxide 2 (1.25 mol) obtained in Production Example B2 and the AGE2 (1.25 mol) obtained in Production Example C2 were used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1 and the AGE1 (1.25 mol) obtained in Production Example C1. The obtained DAGE2 has the following chemical formula (1): R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each contain an alkyl group having 1 to 15 carbon atoms, the total number of carbon atoms of R ¹¹ and R ¹² is 16, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 16; R ²¹ , R ²² , R ²³ and R ²⁴ each contain an alkyl group having 1 to 15 carbon atoms, the total number of carbon atoms of R ²¹ and R ²² is 16, and the total number of carbon atoms of R ²³ and R ²⁴ is 16; R ³¹ , R ³² , R ³³ and R ³⁴ each contain an alkyl group having 1 to 15 carbon atoms, the total number of carbon atoms of _R ³¹ and R ³² is ¹⁶ , and the total number of carbon atoms of R ³³ and R ³⁴ is 16 ^; The compound represented by the chemical formula ( ₁ ) was 42.2%, the compound represented by the chemical formula (2 ₎ was 33.8%, _and the compound represented by the chemical formula (3) was 24.0%.

Manufacturing Example D3
(Preparation of reaction product of AGE3 and epoxide (DAGE3))
DAEG3 was obtained by the same production method as in Production Example D1, except that the internal epoxide 3 (1.25 mol) obtained in Production Example B3 and the AGE3 (1.25 mol) obtained in Production Example C3 were used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1 and the AGE1 (1.25 mol) obtained in Production Example C1. The obtained DAGE3 has the following chemical formula (1): R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each contain an alkyl group having 1 to 11 carbon atoms, the total number of carbon atoms of R ¹¹ and R ¹² is 12, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 12; R ²¹ , R ²² , R ²³ and R ²⁴ each contain an alkyl group having 1 to 11 carbon atoms, the total number of carbon atoms of R ²¹ and R ²² is 12, and the total number of carbon atoms of R ²³ and R ²⁴ is 12; R ³¹ , R ³² , R ³³ and R ³⁴ each contain an alkyl group having 1 to 11 carbon atoms, the total number of carbon atoms of R ³¹ and ^{R 32} is ₁₂ , and the total number of carbon atoms of R ³³ and R ³⁴ is 12 ^; The compound represented by the chemical formula ( ₁ ) was 41.3%, the compound represented by the chemical formula (2 ₎ was 33.1%, and the compound represented by the chemical formula (3) was 25.6% _.

Manufacturing Example D4
(Preparation of reaction product of AGE4 and epoxide (DAGE4))
DAEG4 was obtained by the same production method as in Production Example D1, except that the internal epoxide 1 (1.25 mol) obtained in Production Example B1 and the AGE1 (1.25 mol) obtained in Production Example C1 were replaced with the internal epoxide 4 (1.25 mol) obtained in Production Example B4 and the AGE4 (1.25 mol) obtained in Production Example C4. The obtained DAGE4 has the following chemical formula (1): R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each contain an alkyl group having 1 to 9 carbon atoms, the total number of carbon atoms of R ¹¹ and R ¹² is 10, and the total number of carbon atoms of R ¹³ and R ¹⁴ is 10; R ²¹ , R ²² , R ²³ and R ²⁴ each contain an alkyl group having 1 to 9 carbon atoms, the total number of carbon atoms of R ²¹ and R ²² is 10, and the total number of carbon atoms of R ²³ and R ²⁴ is 10; R ³¹ , R ³² , R ³³ and R ³⁴ each contain an alkyl group having 1 to 9 carbon atoms, the total number of carbon atoms of _R ³¹ and R ³² is ¹⁰ , and the total number of carbon atoms of R ³³ and R ³⁴ is 10 ^; The compound represented by the chemical formula ( ₁ ) was 41.0%, the compound represented by the chemical formula (2 ₎ was 31.0%, _and the compound represented by the chemical formula (3) was 28.0%.

Manufacturing Example D5
(Preparation of reaction product of AGE5 and epoxide (DAGE5))
DAEG5 was obtained by the same method as in Production Example D1, except that 1.25 mol of C14 terminal epoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) and AGE5 (1.25 mol) obtained in Production Example C5 were used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1 and AGE1 (1.25 mol) obtained in Production Example C1. The obtained DAGE5 contained 40.8% of the compound represented by the following chemical formula (4), 32.8% of the compound represented by the following chemical formula (5), and 26.4% of the compound represented by the following chemical formula (6).
(In the formula, one of R ⁴¹ and R ⁴² is a hydrogen atom and the other is a lauryl group, and one of R ⁴³ and R ⁴⁴ is a hydrogen atom and the other is a lauryl group.)
(In the formula, one of R ⁵¹ and R ⁵² is a hydrogen atom and the other is a lauryl group, and one of R ⁵³ and R ⁵⁴ is a hydrogen atom and the other is a lauryl group.)
(In the formula, one of R ⁶¹ and R ⁶² is a hydrogen atom and the other is a lauryl group, one of R ⁶³ and R ⁶⁴ is a hydrogen atom and the other is a lauryl group, and A ¹ and A ² are each independently -CH ₂ -CH(OH)-CH ₂ OH or -CH(-CH ₂ OH) _2. )

Production Example D6
(Preparation of reaction product of AGE6 and epoxide (DAGE6))
DAEG5 was obtained by the same production method as in Production Example D1, except that 2.5 mol of C16 terminal epoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) and AGE6 (1.25 mol) obtained in Production Example C6 were used instead of the internal epoxide 1 (2.5 mol) obtained in Production Example B1 and AGE1 (1.25 mol) obtained in Production Example C1. The obtained DAGE6 contained 43.3% of the compound represented by the following chemical formula (7), 32.7% of the compound represented by the following chemical formula (8), and 24.0% of the compound represented by the following chemical formula (9).
(In the formula, one of R ⁷¹ and R ⁷² is a hydrogen atom and the other is a myristyl group, and one of R ⁷³ and R ⁷⁴ is a hydrogen atom and the other is a myristyl group.)
(In the formula, one of R ⁸¹ and R ⁸² is a hydrogen atom and the other is a myristyl group, and one of R ⁸³ and R ⁸⁴ is a hydrogen atom and the other is a myristyl group.)
(In the formula, one of R ⁹¹ and R ⁹² is a hydrogen atom and the other is a myristyl group, one of R ⁹³ and R ⁹⁴ is a hydrogen atom and the other is a myristyl group, and A ¹ and A ² are each independently -CH ₂ -CH(OH)-CH ₂ OH or -CH(-CH ₂ OH) _2. )

Manufacturing Example D7
(Preparation of reaction product of AGE7 and epoxide (DAGE7))
DAEG7 was obtained by the same method as in Production Example D1, except that 2.5 mol of C18 terminal epoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) and AGE7 (1.25 mol) obtained in Production Example C7 were used instead of the internal epoxide 1 (2.5 mol) obtained in Production Example B1 and AGE1 (1.25 mol) obtained in Production Example C1. The obtained DAGE7 contained 41.2% of the compound represented by the following chemical formula (10), 34.0% of the compound represented by the following chemical formula (11), and 24.8% of the compound represented by the following chemical formula (12).
(In the formula, one of R ¹⁰¹ and R ¹⁰² is a hydrogen atom and the other is a cetyl group, and one of R ¹⁰³ and R ¹⁰⁴ is a hydrogen atom and the other is a cetyl group.)
(In the formula, one of R ¹¹¹ and R ¹¹² is a hydrogen atom, and the other is a cetyl group, and one of R ¹¹³ and R ¹¹⁴ is a hydrogen atom, and the other is a cetyl group.)
(In the formula, one of R ¹²¹ and R ¹²² is a hydrogen atom and the other is a cetyl group, one of R ¹²³ and R ¹²⁴ is a hydrogen atom and the other is a cetyl group, and A ¹ and A ² are each independently -CH ₂ -CH(OH)-CH ₂ OH or -CH(-CH ₂ OH) _2. )

Examples 1 to 4, Comparative Examples 1 to 3
The products prepared in Production Examples D1 to D7 were subjected to the following measurements and evaluations.
<Melt point measurement>
Using a high-sensitivity differential scanning calorimeter (manufactured by Hitachi High-Tech Science Corporation, product name: DSC7000X), each product prepared in Production Examples D1 to D7 was placed in a 70 μL pan and heated from −60° C. to 80° C. at a rate of 2° C./min. The melting point was determined as the maximum peak temperature of the temperature difference detected by a differential thermal electrode against the heating time. The results are shown in Table 1.

<Contact angle measurement>
5.0 g of each product prepared in Production Examples D1 to D7 was added to 100 mL of hexane, and the mixture was thoroughly stirred to prepare a hexane solution. A glass slide (76 mm x 26 mm x 1 mm) was immersed in the hexane solution prepared by the above method for 10 seconds, then immersed in 5 mL of hexane for 10 seconds, and dried with hot air at 120°C for 10 seconds. The glass slide was then placed horizontally on the stage of a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., DM-701), and 2 μL of ion-exchanged water was dropped onto the placed glass slide using a syringe, and the contact angle was measured after 5 seconds. The results are shown in Table 1.

The compounds and compositions of the present invention are useful as surfactants, emulsifiers, dispersants, raw materials for polymers and resins, additives for oils such as lubricating oils, paint additives, agricultural chemical additives, resin additives, metal surface modifiers, cosmetic base materials, medical auxiliaries, textile oils, petroleum chemicals, processing chemicals, lubricants, plasticizers, emulsifiers, dispersants, anti-fogging agents, antistatic agents, defoamers, wetting agents, penetrating agents, agents for oil recovery, cleaning agents, or rust inhibitors.

Claims (4)

A compound represented by the following chemical formula (1), chemical formula (2) or chemical formula (3).
(In the formula, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ¹¹ and R ¹² is 2 or more and 34 or less, the total number of carbon atoms of R ¹³ and R ¹⁴ is 2 or more and 34 or less, and the total number of carbon atoms of R ¹¹ and R ¹² and/or the total number of carbon atoms of R ¹³ and R ¹⁴ is 8 or more and 18 or less .)
(In the formula, R ²¹ , R ²² , R ²³ and R ²⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ²¹ and R ²² is 2 or more and 34 or less, the total number of carbon atoms of R ²³ and R ²⁴ is 2 or more and 34 or less, and the total number of carbon atoms of R ²¹ and R ²² and/or the total number of carbon atoms of R ²³ and R ²⁴ is 8 or more and 18 or less .)
(In the formula, R ³¹ , R ³² , R ³³ and R ³⁴ are aliphatic hydrocarbon groups, the total number of carbon atoms of R ³¹ and R ³² is 2 to 34, the total number of carbon atoms of R ³³ and R ³⁴ is 2 to 34, the total number of carbon atoms of R ³¹ and R ³² and/or the total number of carbon atoms of R ³³ and R ³⁴ is 8 to 18, and A ¹ and A ² are each independently -CH ₂ -CH(OH)-CH ₂ OH, or -CH(-CH ₂ OH) _2. ) 10. The compound of claim 1 , wherein the compound is a surfactant, an emulsifier, a wetting agent, a penetrating agent, an oil recovery agent, a detergent, an oil additive, or a rust inhibitor. A composition comprising at least one compound according to claim 1 . The composition according to claim 3 , wherein the composition is a surfactant composition, an emulsifier composition, a wetting agent composition, a penetrant composition, an oil recovery composition, a detergent composition, an oil composition, or a rust inhibitor composition.