Compounds and Compositions

Abstract

To provide a compound that can form a film having a low melting point and high hydrophobicity, and a composition containing the compound.SOLUTION: The present invention discloses a compound represented by formula (1) or the like (where R11-R14 each denote an aliphatic hydrocarbon group; the total carbon number of R11 and R12 is 2 or more and 34 or less; the total carbon number of R13 and R14 is 2 or more and 34 or less).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to novel compounds and compositions containing said compounds. [Background technology]

[0002] Ether alcohols obtained by reacting epoxyalkanes with polyhydric alcohols are useful as raw materials for emulsifiers, surfactants, dispersants, and the like.

[0003] 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.

[0004] Furthermore, Non-Patent Document 1 discloses hydroxyethers (monomers and dimers) obtained by reacting a terminal epoxyalkane having 8 to 16 carbon atoms with glycerol. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 55-105632 [Non-patent literature]

[0006] [Non-Patent Document 1] SYNTHETIC COMMUNICATIONS, 24(21),3009-3019(1994) Summary of the Invention [Problem to be solved by the invention]

[0007] However, it has been found that the ether alcohol of Patent Document 1 and the hydroxy ether of Non-Patent Document 1 have high melting points, making them difficult to handle, and that the films formed by these ether alcohols and hydroxy ethers have low hydrophobicity.

[0008] 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. [Means for solving the problem]

[0009] As a result of extensive investigations, the present inventors have found that the above problems can be solved by a compound having a specific structure.

[0010] That is, the present invention relates to a compound represented by the following chemical formula (1), chemical formula (2), or chemical formula (3). [ka] (In the formula, R 11 , R 12 , R 13 and R 14 is an aliphatic hydrocarbon group, and R 11 and R 12 The total number of carbon atoms in R is 2 to 34. 13 and R 14 The total number of carbon atoms is 2 to 34.) [ka] (In the formula, R 21 , R 22 , R 23 and R 24 is an aliphatic hydrocarbon group, and R 21 and R 22 The total number of carbon atoms in R is 2 to 34. 23 and R 24 The total number of carbon atoms is 2 to 34.) [ka] (In the formula, R 31, R 32 , R 33 and R 34 is an aliphatic hydrocarbon group, and R 31 and R 32 The total number of carbon atoms in R is 2 to 34. 33 and R 34 The total number of carbon atoms in A is 2 to 34. 1 and A 2 are each independently a hydrogen atom, -CH-CH(OH)-CHOH, or -CH(-CHOH). Effect of the Invention

[0011] The compounds of the present invention represented by the above 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 manifested by 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 cohesive force due to intermolecular repulsion caused by steric hindrance and uneven molecular arrangement. In addition, the ether alcohols of the present invention have excellent handleability due to their low melting point, and are also excellent in forming hydrophobic films. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will be described in detail below.

[0013] <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. [ka] (In the formula, R 11 , R 12 , R 13 and R 14 is an aliphatic hydrocarbon group, and R 11 and R 12 The total number of carbon atoms in R is 2 to 34. 13 and R 14The total number of carbon atoms is 2 to 34.) [ka] (In the formula, R 21 , R 22 , R 23 and R 24 is an aliphatic hydrocarbon group, and R 21 and R 22 The total number of carbon atoms in R is 2 to 34. 23 and R 24 The total number of carbon atoms is 2 to 34.) [ka] (In the formula, R 31 , R 32 , R 33 and R 34 is an aliphatic hydrocarbon group, and R 31 and R 32 The total number of carbon atoms in R is 2 to 34. 33 and R 34 The total number of carbon atoms in A is 2 to 34. 1 and A 2 are each independently a hydrogen atom, -CH-CH(OH)-CHOH, or -CH(-CHOH).

[0014] R in the above chemical formula (1) 11 , R 12 , R 13 and R 14 R in the above chemical formula (2) 21 , R 22 , R 23 and R 24 and R in the above chemical formula (3) 31 , R 32 , R 33 and R 34 is an aliphatic hydrocarbon group, and from the viewpoints of production efficiency and ease of production, is preferably a linear or branched alkyl group, more preferably a linear alkyl group, and even more preferably a primary linear alkyl group. 11 , R 12 , R 13 , R 14 , R 21 , R22 , R 23 , R 24 , R 31 , R 32 , R 33 and R 34 The carbon numbers of R in the above chemical formula (1) are each independently 1 to 33, and may have a distribution. 11 , R 12 , R 13 and R 14 may be the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups. 21 , R 22 , R 23 and R 24 and R in the above chemical formula (3) 31 , R 32 , R 33 and R 34 The same applies to the above.

[0015] R in the above chemical formula (1) 11 and R 12 The total number of carbon atoms in R 13 and R 14 The total number of carbon atoms is 2 or more and 34 or less, and from the viewpoint of the formability of a hydrophobic film, it is preferably 8 or more, more preferably 10 or more, and from the viewpoint of a low melting point and handleability, it is preferably 18 or less, more preferably 16 or less.

[0016] R in the above chemical formula (1) 11 , R 12 , R 13 and R 14 From the viewpoints of hydrophobic film-forming ability, low melting point, and handleability, each of them independently is 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.

[0017] The compound represented by the chemical formula (1) is R 11 and R 12 and / or R 13 and R 14In the case where the compound contains two or more compounds each having a different number of carbon atoms, from the viewpoints of hydrophobic film formation, low melting point and handling properties, R 11 has 5 or more carbon atoms and R 12 Compounds with 5 or more carbon atoms, or R 13 has 5 or more carbon atoms and R 14 The content of the compound having 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, relative to the total amount of the compounds represented by the chemical formula (1), and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less.

[0018] R in the above chemical formula (2) 21 and R 22 The total number of carbon atoms in R 23 and R 24 The total number of carbon atoms is 2 or more and 34 or less, and from the viewpoint of the formability of a hydrophobic film, it is preferably 8 or more, more preferably 10 or more, and from the viewpoint of a low melting point and handleability, it is preferably 18 or less, more preferably 16 or less.

[0019] R in the above chemical formula (2) 21 , R 22 , R 23 and R 24 From the viewpoints of hydrophobic film-forming ability, low melting point, and handleability, each of them independently is 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.

[0020] The compound represented by the chemical formula (2) is R 21 and R 22 and / or R 23 and R 24 In the case where the compound contains two or more compounds each having a different number of carbon atoms, from the viewpoints of hydrophobic film formation, low melting point and handling properties, R 21 has 5 or more carbon atoms and R 22 Compounds with 5 or more carbon atoms, or R 23has 5 or more carbon atoms and R 24 The content of the compound having 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, relative to the total amount of the compounds represented by the chemical formula (2), and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less.

[0021] R in the above chemical formula (3) 31 and R 32 The total number of carbon atoms in R 33 and R 34 The total number of carbon atoms is 2 or more and 34 or less, and from the viewpoint of the formability of a hydrophobic film, it is preferably 8 or more, more preferably 10 or more, and from the viewpoint of a low melting point and handleability, it is preferably 18 or less, more preferably 16 or less.

[0022] R in the above chemical formula (3) 31 , R 32 , R 33 and R 34 From the viewpoints of hydrophobic film-forming ability, low melting point, and handleability, each of them independently is 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.

[0023] The compound represented by the chemical formula (3) is R 31 and R 32 and / or R 33 and R 34 In the case where the compound contains two or more compounds each having a different number of carbon atoms, from the viewpoints of hydrophobic film formation, low melting point and handling properties, R 31 has 5 or more carbon atoms and R 32 Compounds with 5 or more carbon atoms, or R 33 has 5 or more carbon atoms and R 34The content of the compound having 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, relative to the total amount of the compounds represented by the chemical formula (3), and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less.

[0024] A in the above chemical formula (3) 1 and A 2 are each independently a hydrogen atom, -CH2-CH(OH)-CH2OH, or -CH(-CH2OH)2, and from the viewpoint of the formability of a hydrophobic film, are preferably -CH2-CH(OH)-CH2OH or -CH(-CH2OH)2.

[0025] From the viewpoints 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.

[0026] 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 production method is usually a compound represented by the chemical formula (1), a compound represented by the chemical formula (2), and a compound (A) represented by the chemical formula (3). 1 and A 2 are each independently -CH2-CH(OH)-CH2OH, or -CH(-CH2OH)2. In the production method, the compound represented by the chemical formula (1) is usually a mixture containing R 11 and R 12 and / or R 13 and R 14The compound represented by the chemical formula (2) includes two or more compounds each having a different number of carbon atoms, 21 and R 22 and / or R 23 and R 24 The compound represented by the chemical formula (3) includes two or more compounds each having a different number of carbon atoms, 31 and R 32 and / or R 33 and R 34 In the above-mentioned production method, the compound represented by the above-mentioned chemical formula (3) usually includes two or more compounds each having a different number of carbon atoms. 1 and A 2 A compound in which A is -CH2-CH(OH)-CH2OH; 1 and A 2 A compound in which A is -CH(-CH2OH)2 1 and A 2 In the compound represented by the above chemical formula (3), A is a mixture of a compound in which one of the two is -CH2-CH(OH)-CH2OH and the other is -CH(-CH2OH). 1 Or A 2 The compound in which A is a hydrogen atom can be produced by dehydration condensation of a glycerin ring-opening product obtained by reacting the internal epoxide with glycerin, and a water ring-opening product obtained by reacting the internal epoxide with water. 1 and A 2 The compound in which is a hydrogen atom can be produced by reacting the internal epoxide with water to form a water-ring-opened product, which is then subjected to dehydration condensation.

[0027] The olefin used in the production of the ether alcohol may contain terminal olefins in addition to internal olefins. In this case, the content of the terminal olefins in the olefins 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.

[0028] 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).

[0029] 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 assistant, an oil for textiles, 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, an agent for oil recovery, a cleaning agent, or a rust inhibitor. The agent for oil recovery is preferably an agent for crude oil recovery, more preferably an agent for EOR (Enhanced Oil Recovery, the same applies below), and even more preferably an agent for chemical EOR.

[0030] <Composition> The composition of the present invention contains at least the ether alcohol.

[0031] 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, still more preferably 80% by mass or more, and even more preferably 100% by mass.

[0032] 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.

[0033] From the viewpoints of ease of handling and storage stability, the composition may contain solvents and additives that are appropriately added depending on the application.

[0034] 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). [ka] (In the formula, R 11 , R 12 , R 13 and R 14 is an aliphatic hydrocarbon group, and R 11 and R 12 The total number of carbon atoms in R is 2 to 34. 13 and R 14 The total number of carbon atoms is 2 to 34.) [ka] (In the formula, R 21 , R 22 , R 23 and R 24 is an aliphatic hydrocarbon group, and R 21 and R 22 The total number of carbon atoms in R is 2 to 34. 23 and R 24 The total number of carbon atoms is 2 to 34.) [ka] (In the formula, R 31 , R 32 , R 33 and R 34 is an aliphatic hydrocarbon group, and R 31 and R 32 The total number of carbon atoms in R is 2 to 34. 33 and R 34 The total number of carbon atoms in A is 2 to 34. 1 and A 2 are each independently a hydrogen atom, -CH-CH(OH)-CHOH, or -CH(-CHOH). <2> 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. <1> The compound according to claim 1, <3> 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 has 1 or more and 33 or less carbon atoms; <1> or <2> The compound according to claim 1, <4> R in the above chemical formula (1) 11 , R 12 , R 13 and R 14 are the same or different aliphatic hydrocarbon groups; <1> ~ <3> 2. The compound according to claim 1 , <5> R in the above chemical formula (2) 21 , R 22 , R 23 and R 24 are the same or different aliphatic hydrocarbon groups; <1> ~ <4> 2. The compound according to claim 1 , <6> R in the above chemical formula (3) 31 , R32 , R 33 and R 34 are the same or different aliphatic hydrocarbon groups; <1> ~ <5> 2. The compound according to claim 1 , <7> R in the above chemical formula (1) 11 and R 12 The total number of carbon atoms in R 13 and R 14 The total number of carbon atoms is preferably 8 or more, more preferably 10 or more, and is preferably 18 or less, more preferably 16 or less. <1> ~ <6> 2. The compound according to claim 1 , <8> R in the above chemical formula (1) 11 and R 12 The total number of carbon atoms in R 13 and R 14 The total number of carbon atoms is 8 to 18. <1> ~ <6> 2. The compound according to claim 1 , <9> R in the above chemical formula (1) 11 and R 12 The total number of carbon atoms in R 13 and R 14 The total number of carbon atoms is 10 or more and 16 or less. <1> ~ <6> 2. The compound according to claim 1 , <10> R in the above chemical formula (1) 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. <1> ~ <9> 2. The compound according to claim 1 , <11> The compound represented by the chemical formula (1) is R 11 and R 12 and / or R 13 and R 14 When the compound contains two or more compounds with different carbon numbers, R 11 has 5 or more carbon atoms and R 12Compounds with 5 or more carbon atoms, or R 13 has 5 or more carbon atoms and R 14 The content of the compound having 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, based on the total amount of the compound represented by the chemical formula (1), and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less. <1> ~ <10> 2. The compound according to claim 1 , <12> The compound represented by the chemical formula (1) is R 11 and R 12 and / or R 13 and R 14 When the compound contains two or more compounds with different carbon numbers, R 11 has 5 or more carbon atoms and R 12 Compounds with 5 or more carbon atoms, or R 13 has 5 or more carbon atoms and R 14 The content of the compound having 5 or more carbon atoms is 10% by mass or more and 90% by mass or less with respect to the total amount of the compound represented by the chemical formula (1). <1> ~ <10> 2. The compound according to claim 1 , <13> The compound represented by the chemical formula (1) is R 11 and R 12 and / or R 13 and R 14 When the compound contains two or more compounds with different carbon numbers, R 11 has 5 or more carbon atoms and R 12 Compounds with 5 or more carbon atoms, or R 13 has 5 or more carbon atoms and R 14 The content of the compound having 5 or more carbon atoms is 20% by mass or more and 80% by mass or less with respect to the total amount of the compound represented by the chemical formula (1). <1> ~ <10> 2. The compound according to claim 1 , <14> The compound represented by the chemical formula (1) is R 11 and R 12 and / or R 13 and R 14 When the compound contains two or more compounds with different carbon numbers, R11 has 5 or more carbon atoms and R 12 Compounds with 5 or more carbon atoms, or R 13 has 5 or more carbon atoms and R 14 The content of the compound having 5 or more carbon atoms is 30% by mass or more and 70% by mass or less with respect to the total amount of the compound represented by the chemical formula (1). <1> ~ <10> 2. The compound according to claim 1 , <15> R in the above chemical formula (2) 21 and R 22 The total number of carbon atoms in R 23 and R 24 The total number of carbon atoms is preferably 8 or more, more preferably 10 or more, and is preferably 18 or less, more preferably 16 or less. <1> ~ <14> 2. The compound according to claim 1 , <16> R in the above chemical formula (2) 21 and R 22 The total number of carbon atoms in R 23 and R 24 The total number of carbon atoms is 8 to 18. <1> ~ <14> 2. The compound according to claim 1 , <17> R in the above chemical formula (2) 21 and R 22 The total number of carbon atoms in R 23 and R 24 The total number of carbon atoms is 10 or more and 16 or less. <1> ~ <14> 2. The compound according to claim 1 , <18> R in the above chemical formula (2) 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. <1> ~ <17> 2. The compound according to claim 1 , <19> The compound represented by the chemical formula (2) is R 21 and R 22 and / or R 23 and R24 When the compound contains two or more compounds with different carbon numbers, R 21 has 5 or more carbon atoms and R 22 Compounds with 5 or more carbon atoms, or R 23 has 5 or more carbon atoms and R 24 The content of the compound having 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, based on the total amount of the compound represented by the chemical formula (2). <1> ~ <18> 2. The compound according to claim 1 , <20> The compound represented by the chemical formula (2) is R 21 and R 22 and / or R 23 and R 24 When the compound contains two or more compounds with different carbon numbers, R 21 has 5 or more carbon atoms and R 22 Compounds with 5 or more carbon atoms, or R 23 has 5 or more carbon atoms and R 24 The content of the compound having 5 or more carbon atoms is 10% by mass or more and 90% by mass or less with respect to the total amount of the compound represented by the chemical formula (2). <1> ~ <18> 2. The compound according to claim 1 , <21> The compound represented by the chemical formula (2) is R 21 and R 22 and / or R 23 and R 24 When the compound contains two or more compounds with different carbon numbers, R 21 has 5 or more carbon atoms and R 22 Compounds with 5 or more carbon atoms, or R 23 has 5 or more carbon atoms and R 24 The content of the compound having 5 or more carbon atoms is 20% by mass or more and 80% by mass or less with respect to the total amount of the compound represented by the chemical formula (2). <1> ~ <18> 2. The compound according to claim 1 , <22> The compound represented by the chemical formula (2) is R 21 and R 22and / or R 23 and R 24 When the compound contains two or more compounds with different carbon numbers, R 21 has 5 or more carbon atoms and R 22 Compounds with 5 or more carbon atoms, or R 23 has 5 or more carbon atoms and R 24 The content of the compound having 5 or more carbon atoms is 30% by mass or more and 70% by mass or less with respect to the total amount of the compound represented by the chemical formula (2). <1> ~ <18> 2. The compound according to claim 1 , <23> R in the above chemical formula (3) 31 and R 32 The total number of carbon atoms in R 33 and R 34 The total number of carbon atoms is preferably 8 or more, more preferably 10 or more, and is preferably 18 or less, more preferably 16 or less. <1> ~ <22> 2. The compound according to claim 1 , <24> R in the above chemical formula (3) 31 and R 32 The total number of carbon atoms in R 33 and R 34 The total number of carbon atoms is 8 to 18. <1> ~ <22> 2. The compound according to claim 1 , <25> R in the above chemical formula (3) 31 and R 32 The total number of carbon atoms in R 33 and R 34 The total number of carbon atoms is 10 or more and 16 or less. <1> ~ <22> 2. The compound according to claim 1 , <26> R in the above chemical formula (3) 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. <1> ~ <25> 2. The compound according to claim 1 , <27> The compound represented by the chemical formula (3) is R 31 and R 32 and / or R 33 and R 34 When the compound contains two or more compounds with different carbon numbers, R 31 has 5 or more carbon atoms and R 32 Compounds with 5 or more carbon atoms, or R 33 has 5 or more carbon atoms and R 34 The content of the compound having 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, based on the total amount of the compound represented by the chemical formula (3), and is preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less. <1> ~ <26> 2. The compound according to claim 1 , <28> The compound represented by the chemical formula (3) is R 31 and R 32 and / or R 33 and R 34 When the compound contains two or more compounds with different carbon numbers, R 31 has 5 or more carbon atoms and R 32 Compounds with 5 or more carbon atoms, or R 33 has 5 or more carbon atoms and R 34 The content of the compound having 5 or more carbon atoms is 10% by mass or more and 90% by mass or less with respect to the total amount of the compound represented by the chemical formula (3). <1> ~ <26> 2. The compound according to claim 1 , <29> The compound represented by the chemical formula (3) is R 31 and R 32 and / or R 33 and R 34 When the compound contains two or more compounds with different carbon numbers, R 31 has 5 or more carbon atoms and R 32 Compounds with 5 or more carbon atoms, or R 33 has 5 or more carbon atoms and R 34 The content of the compound having 5 or more carbon atoms is 20% by mass or more and 80% by mass or less with respect to the total amount of the compound represented by the chemical formula (3). <1> ~ <26> 2. The compound according to claim 1 , <30> The compound represented by the chemical formula (3) is R 31 and R 32 and / or R 33 and R 34 When the compound contains two or more compounds with different carbon numbers, R 31 has 5 or more carbon atoms and R 32 Compounds with 5 or more carbon atoms, or R 33 has 5 or more carbon atoms and R 34 The content of the compound having 5 or more carbon atoms is 30% by mass or more and 70% by mass or less with respect to the total amount of the compound represented by the chemical formula (3). <1> ~ <26> 2. The compound according to claim 1 , <31> A in the above chemical formula (3) 1 and A 2 are each independently -CH-CH(OH)-CHOH, or -CH(-CHOH); <1> ~ <30> 2. The compound according to claim 1 , <32> The melting point of the compound represented by the chemical formula (1) 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 is −200° C. or higher. <1> ~ <31> 2. The compound according to claim 1 , <33> The melting point of the compound represented by the chemical formula (2) 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 is −200° C. or higher. <1> ~ <32> 2. The compound according to claim 1 , <34> The melting point of the compound represented by the chemical formula (3) is preferably 30° C. or lower, more preferably 20° C. or lower, even more preferably 10° C. or lower, even more preferably 5° C. or lower, and is −200° C. or higher. <1> ~ <33> 2. The compound according to claim 1 , <35> The compound is a surfactant, an emulsifier, a wetting agent, a penetrant, an oil recovery agent, a detergent, an oil additive, or a rust inhibitor; <1> ~ <34> 2. The compound according to claim 1 , <36> 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; <35> The compound according to claim 1, <37> <1> ~ <36> A composition comprising at least one compound according to any one of the above items. <38> The composition contains two or more compounds represented by the chemical formula (1). <37> The composition described in <39> The composition contains two or more compounds represented by the chemical formula (2). <37> The composition described in <40> The composition contains two or more compounds represented by the chemical formula (3). <37> The composition described in <41> The composition contains one or more compounds represented by the chemical formula (1) and one or more compounds represented by the chemical formula (2). <37> The composition described in <42> The composition contains one or more compounds represented by the chemical formula (1) and one or more compounds represented by the chemical formula (3). <37> The composition described in <43> The composition contains one or more compounds represented by the chemical formula (2) and one or more compounds represented by the chemical formula (3). <37> The composition described in <44> The composition contains one or more 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). <37> The composition described in <45> The total content of the compounds 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 even more preferably 100% by mass. <37> ~ <44> 2. The composition according to claim 1 . <46> The composition is a surfactant composition, an emulsifier composition, a wetting agent composition, a penetrant composition, an oil recovery composition, a cleaning agent composition, an oil agent composition, or a rust inhibitor composition. <37> ~ <45> 2. The composition according to claim 1 . <47> The oil recovery composition is preferably a crude oil recovery composition, more preferably an EOR composition, and even more preferably a chemical EOR composition; <46> The composition described in EXAMPLES

[0035] The present invention will be specifically described below based on examples. In addition, unless otherwise specified in the table, the content (%) of each component indicates mass %, and the ratio ( / ) indicates mass ratio. In addition, various measurement methods are as follows.

[0036] <Method for measuring the double bond distribution of olefins> The double bond distribution of olefins was measured by gas chromatography (hereinafter abbreviated as GC). Specifically, olefins were reacted with dimethyl disulfide to produce dithiolated derivatives, and each component was then separated by GC. The double bond distribution of olefins was determined from each peak area. The equipment 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 30m x 250μm x 0.15μm (manufactured by Frontier Labs, Inc.) Detector: Flame ionization detector (FID) Injection temperature: 300℃ Detector temperature: 350℃ Oven: 60℃(0min.)→2℃ / min.→225℃→20℃ / min.→350℃→350℃(5.2min.)

[0037] <Method for measuring the content ratio of structural isomers of alkyl glyceryl ether> The ratio of structural isomers of alkyl glyceryl ether (glycerin with a primary hydroxyl group and glycerin with a secondary hydroxyl group) is:1 Specifically, 0.05 g of alkyl glyceryl ether, 0.2 g of trifluoroacetic anhydride, and 1 g of deuterated chloroform were mixed, 1 Measurement was performed by H-NMR under the following conditions: Nuclear magnetic resonance spectrometer: Agilent 400-MR DD2, manufactured by Agilent Technologies, Inc. Observation range: 6410.3Hz Data points: 65536 Measurement mode: Presat Pulse width: 45° Pulse delay time: 10sec Number of times accumulated: 128 times

[0038] <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 calculated from the peak area. The measurement conditions were as follows. HPLC equipment: Product name DIONEX Ultimаte 3000 Column: L-column ODS, 5μm, Cat.No.622070, Size4.6×150mm Mobile phase: 10 mM ammonium acetate in methanol Flow rate: 1mL / min Oven temperature: 40℃ Detector: Charged Aerosol Detector (CAD)

[0039] <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) = (percentage 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 (%))

[0040] <Production of internal olefins> Manufacturing example A1 (Production of Internal Olefin with Carbon Number of 16 (Internal Olefin 1)) A flask equipped with a stirrer was charged with 7000g (28.9 mol) 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, and the reaction was carried out for 32 hours at 280°C while circulating nitrogen (7000mL / min) through the system under stirring. After the reaction was completed, 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.

[0041] Manufacturing example A2 (Production of Internal Olefin with Carbon Number of 18 (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 the reaction was completed, 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.

[0042] Manufacturing example A3 (Production of Internal Olefin with Carbon Number 14 (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.

[0043] Manufacturing example A4 (Production of Internal Olefin with Carbon Number 12 (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.

[0044] <Production of Internal Epoxide> Manufacturing example B1 (Production of Internal Epoxide with 16 Carbons (Internal Epoxide 1)) In a flask equipped with a stirrer, 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.) were charged 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.

[0045] Manufacturing example B2 (Production of Internal Epoxide with 18 Carbons (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.

[0046] Manufacturing example B3 (Production of Internal Epoxide with 14 Carbons (Internal Epoxide 3)) Internal epoxide 3 was obtained in the same manner as in Production Example B1, except that internal olefin 3 (3.56 mol) obtained in Production Example A3 was used instead of internal olefin 1 (3.56 mol) obtained in Production Example A1.

[0047] Manufacturing example B4 (Production of Internal Epoxide with 12 Carbons (Internal Epoxide 4)) Internal epoxide 4 was obtained in the same manner as in Production Example B1, except that internal olefin 4 (3.56 mol) obtained in Production Example A4 was used instead of internal olefin 1 (3.56 mol) obtained in Production Example A1.

[0048] <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. 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., respectively.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] Manufacturing example C5 (Preparation of reaction product of C14 terminal epoxide and glycerin (AGE5)) AGE5 was obtained by the same method as in Production Example C1, except that 1.25 mol of C14 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 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.

[0054] Manufacturing example C6 (Production of reaction product of C16 terminal epoxide and glycerin (AGE6)) AGE6 was obtained by the same method as in Production Example C1, except that 1.25 mol of C16 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 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.

[0055] 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.

[0056] <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.

[0057] Manufacturing example D1 (Preparation of reaction product of AGE1 and epoxide (DAGE1)) 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. The reaction was then carried out at 150°C for 5 hours. Hexane was added to the liquid obtained by this reaction, which was then washed with ion-exchanged water, and then concentrated under reduced pressure using an evaporator to obtain 700 g of DAGE1. The obtained DAGE1 is represented by the above chemical formula (1), 11 , R 12 , R 13 and R 14 Each of R contains an alkyl group having 1 to 13 carbon atoms. 11 and R 12 The total number of carbon atoms is 14, and R 13 and R 14 The total number of carbon atoms in the formula (2) is 14. 21 , R 22 , R 23 and R 24 Each of R contains an alkyl group having 1 to 13 carbon atoms. 21 and R 22 The total number of carbon atoms is 14, and R 23 and R 24 The total number of carbon atoms in the formula (3) is 14. 31 , R 32 , R 33 and R 34 Each of R contains an alkyl group having 1 to 13 carbon atoms. 31 and R32 The total number of carbon atoms is 14, and R 33 and R 34 The total number of carbon atoms is 14, and A 1 and A 2 were -CH2-CH(OH)-CH2OH or -CH(-CH2OH)2, respectively, and contained 42.0% of the compound represented by the chemical formula (1), 34.8% of the compound represented by the chemical formula (2), and 23.2% of the compound represented by the chemical formula (3).

[0058] Manufacturing example D2 (Production of reaction product of AGE2 and epoxide (DAGE2)) DAEG2 was obtained by the same 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 is represented by the above chemical formula (1), 11 , R 12 , R 13 and R 14 Each of R contains an alkyl group having 1 to 15 carbon atoms. 11 and R 12 The total number of carbon atoms is 16, and R 13 and R 14 The total number of carbon atoms in the formula (2) is 16. 21 , R 22 , R 23 and R 24 Each of R contains an alkyl group having 1 to 15 carbon atoms. 21 and R 22 The total number of carbon atoms is 16, and R 23 and R 24 The total number of carbon atoms in the formula (3) is 16. 31 , R 32 , R 33 and R 34 Each of R contains an alkyl group having 1 to 15 carbon atoms. 31 and R 32 The total number of carbon atoms is 16, and R 33 and R 34 The total number of carbon atoms is 16, and A 1and A 2 were -CH2-CH(OH)-CH2OH or -CH(-CH2OH)2, respectively, and contained 42.2% of the compound represented by the chemical formula (1), 33.8% of the compound represented by the chemical formula (2), and 24.0% of the compound represented by the chemical formula (3).

[0059] Manufacturing example D3 (Production of reaction product of AGE3 and epoxide (DAGE3)) DAEG3 was obtained by the same 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 is represented by the above chemical formula (1), 11 , R 12 , R 13 and R 14 Each of R contains an alkyl group having 1 to 11 carbon atoms. 11 and R 12 The total number of carbon atoms is 12, and R 13 and R 14 The total number of carbon atoms in the formula (2) is 12. 21 , R 22 , R 23 and R 24 Each of R contains an alkyl group having 1 to 11 carbon atoms. 21 and R 22 The total number of carbon atoms is 12, and R 23 and R 24 The total number of carbon atoms in the formula (3) is 12. 31 , R 32 , R 33 and R 34 Each of R contains an alkyl group having 1 to 11 carbon atoms. 31 and R 32 The total number of carbon atoms is 12, and R 33 and R 34 The total number of carbon atoms is 12, and A 1 and A 2were -CH2-CH(OH)-CH2OH or -CH(-CH2OH)2, respectively, and contained 41.3% of the compound represented by the chemical formula (1), 33.1% of the compound represented by the chemical formula (2), and 25.6% of the compound represented by the chemical formula (3).

[0060] Manufacturing example D4 (Production of reaction product of AGE4 and epoxide (DAGE4)) DAEG4 was obtained by the same method as in Production Example D1, except that the internal epoxide 4 (1.25 mol) obtained in Production Example B4 and the AGE4 (1.25 mol) obtained in Production Example C4 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 DAGE4 is represented by the above chemical formula (1), 11 , R 12 , R 13 and R 14 Each of R contains an alkyl group having 1 to 9 carbon atoms. 11 and R 12 The total number of carbon atoms is 10, and R 13 and R 14 The total number of carbon atoms in the formula (2) is 10. 21 , R 22 , R 23 and R 24 Each of R contains an alkyl group having 1 to 9 carbon atoms. 21 and R 22 The total number of carbon atoms is 10, and R 23 and R 24 The total number of carbon atoms in the formula (3) is 10. 31 , R 32 , R 33 and R 34 Each of R contains an alkyl group having 1 to 9 carbon atoms. 31 and R 32 The total number of carbon atoms is 10, and R 33 and R 34 The total number of carbon atoms is 10, and A 1 and A 2were -CH2-CH(OH)-CH2OH or -CH(-CH2OH)2, respectively, and contained 41.0% of the compound represented by the chemical formula (1), 31.0% of the compound represented by the chemical formula (2), and 28.0% of the compound represented by the chemical formula (3).

[0061] Manufacturing example D5 (Production 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). [ka] (In the formula, R 41 and R 42 One of the groups is a hydrogen atom and the other is a lauryl group. 43 and R 44 One of the groups is a hydrogen atom and the other is a lauryl group. [ka] (In the formula, R 51 and R 52 One of the groups is a hydrogen atom and the other is a lauryl group. 53 and R 54 One of the groups is a hydrogen atom and the other is a lauryl group. [ka] (In the formula, R 61 and R 62 One of the groups is a hydrogen atom and the other is a lauryl group. 63 and R 64 One of the groups is a hydrogen atom and the other is a lauryl group. 1 and A 2are each independently -CH-CH(OH)-CHOH, or -CH(-CHOH).

[0062] Manufacturing example D6 (Production of reaction product of AGE6 and epoxide (DAGE6)) DAEG5 was obtained by the same method as in Production Example D1, except that 2.5 mol of C16 terminal epoxide (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). [ka] (In the formula, R 71 and R 72 One of the groups is a hydrogen atom and the other is a myristyl group. 73 and R 74 One of the groups is a hydrogen atom and the other is a myristyl group. [ka] (In the formula, R 81 and R 82 One of the groups is a hydrogen atom and the other is a myristyl group. 83 and R 84 One of the groups is a hydrogen atom and the other is a myristyl group. [ka] (In the formula, R 91 and R 92 One of the groups is a hydrogen atom and the other is a myristyl group. 93 and R 94 One of the groups is a hydrogen atom and the other is a myristyl group. 1 and A 2 are each independently -CH-CH(OH)-CHOH, or -CH(-CHOH).

[0063] 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 moles of C18 terminal epoxide (Tokyo Chemical Industry Co., Ltd.) and AGE7 (1.25 moles) obtained in Production Example C7 were used instead of the internal epoxide 1 (2.5 moles) obtained in Production Example B1 and AGE1 (1.25 moles) 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). [ka] (In the formula, R 101 and R 102 One of the groups is a hydrogen atom and the other is a cetyl group. 103 and R 104 One of them is a hydrogen atom and the other is a cetyl group.) [ka] (In the formula, R 111 and R 112 One of the groups is a hydrogen atom and the other is a cetyl group. 113 and R 114 One of them is a hydrogen atom and the other is a cetyl group.) [ka] (In the formula, R 121 and R 122 One of the groups is a hydrogen atom and the other is a cetyl group. 123 and R 124 One of them is a hydrogen atom and the other is a cetyl group, and A 1 and A 2 are each independently -CH-CH(OH)-CHOH, or -CH(-CHOH).

[0064] 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 (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 the temperature was raised from -60 ° C to 80 ° C at 2 ° C / min, and the temperature at the maximum peak of the temperature difference detected by the differential thermal electrode against the temperature rise time was taken as the melting point. The results are shown in Table 1.

[0065] <Contact angle measurement> 5.0 g of each product prepared in Production Examples D1 to D7 was added to 100 mL of hexane and 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 (Kyowa Interface Science Co., Ltd., DM-701), 2 μL of ion-exchanged water was dropped onto the glass slide using a syringe, and the contact angle was measured after 5 seconds. The results are shown in Table 1.

[0066] [Table 1] [Industrial Applicability]

[0067] 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, oils for fibers, petroleum agents, processing agents, lubricants, plasticizers, emulsifiers, dispersants, antifogging agents, antistatic agents, defoamers, wetting agents, penetrating agents, agents for oil recovery, detergents, or rust inhibitors.

Claims

1. A compound represented by the following chemical formula (1), chemical formula (2) or chemical formula (3). 【Chemistry 1】 (In the formula, R １１ , R １２ , R １３ and R １４ is an aliphatic hydrocarbon group, R １１ and R １２ The total number of carbon atoms in R is 2 to 34. １３ and R １４ 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. 【Chemistry 2】 (In the formula, R ２１ , R ２２ , R ２３ and R ２４ is an aliphatic hydrocarbon group, R ２１ and R ２２ The total number of carbon atoms in R is 2 to 34. ２３ and R ２４ 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. 【Chemistry 3】 (In the formula, R ３１ , R ３２ , R ３３ and R ３４ is an aliphatic hydrocarbon group, R ３１ and R ３２ The total number of carbon atoms in R is 2 to 34. ３３ and R 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 or more and 18 or less; １ and A ２ Each independently represents -CH ２ -CH(OH)-CH ２ OH, or -CH(-CH ２ O.H. ２ It is.)

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.

3. A composition comprising at least one compound according to claim 1.

4. 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.

Images