JPH07316095A - New liquid fatty acid derivative - Google Patents

Abstract

PURPOSE:To obtain the subject fatty acid derivative having a specified structure, excellent in oxidation stability and thermal stability, free from a smell and useful as a raw material for cosmetics, a lubricant, etc. CONSTITUTION:A liquid fatty acid derivative of formula I [R<1> is a 1 to 10C alkyl or a 3 to 10C cycloalkyl; (a) and (c) are each 0 to 19, (a)+(c) is 13 to 19; (b) is l to 31. In addition, a monoalkoxy fatty acid of formula II [R<2> is the same as R<1>; (d) and (J) are each 0 to 19 and (d)+(e) is 15 to 19], e.g. 9- methoxystearic acid or a trialkoxyfatty acid of formula III (R<3> and R<4> are each the same as R<1>; (f), (g) and (h) are each 0 to 18, (f)+(g)+(h) is 14 to 18], e.g. 9,12-dimethoxystearic acid are preferable.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel liquid fatty acid derivative. More specifically, a novel alkoxy fatty acid,
It relates to dialkoxy fatty acids and trialkoxy fatty acids.

[0002]

2. Description of the Related Art Conventionally, unsaturated fatty acids, branched fatty acids, lower fatty acids and the like have been known as liquid fatty acids, and representative examples thereof include oleic acid, linoleic acid, linolenic acid,
Examples include isostearic acid.

[0003]

However, these liquid fatty acids alone are still insufficient to meet a variety of industrial needs. Widening the range of choices according to various new applications is expected to have a great industrial advantage.

[0004]

Means for Solving the Problems The inventors of the present invention have conducted extensive studies to achieve the above-mentioned object and found that an alkoxy fatty acid derivative having a specific structure is a novel and useful liquid compound which has not been described in the literature. The present invention has been completed based on such findings.

That is, the liquid fatty acid derivative according to the present invention is
It is characterized by being represented by the general formula (1).

CH ₃ (CH ₂ ) a- [CH (-OR ¹ )-
_{(CH 2) c] b-} COOH (1) [ wherein, R ¹ represents a cycloalkyl group alkyl or 3-10 carbon atoms having 1 to 10 carbon atoms. a and c are the same or different and are 0 to 19
, And a + c = 13 to 19. b is 1
Represents an integer of 3; ]

As the liquid fatty acid derivative represented by the general formula (1), more specifically, monoalkoxy fatty acid represented by the general formula (2), dialkoxy fatty acid represented by the general formula (3) and general An example is a trialkoxy fatty acid represented by the formula (4).

CH ₃ (CH ₂ ) d-CH (-OR ² )-(CH ₂ ) e-COOH (2) [In the formula, R ² is an alkyl group having 1 to 10 carbon atoms or 3 to 10 carbon atoms. Represents a cycloalkyl group. d and e are the same or different and represent an integer of 0 to 19, and d + e = 15 to
It is 19. ]

CH ₃ (CH ₂ ) f-CH (-OR ³ )-(CH ₂ ) g-CH (-OR ⁴ ) * *-(CH ₂ ) h-COOH (3) [wherein R ³ , R ⁴ is the same or different and has 1 to 10 carbon atoms.
Represents an alkyl group or a cycloalkyl group having 3 to 10 carbon atoms. f, g, and h are the same or different and represent an integer of 0 to 18, and f + g + h = 14 to 18. ]

CH ₃ (CH ₂ ) i-CH (-OR ⁵ )-(CH ₂ ) j-CH (-OR ⁶ ) * *-(CH ₂ ) k-CH (-OR ⁷ )-(CH ₂ ). l-COOH (4) [wherein R ⁵ , R ⁶ and R ⁷ are the same or different and have 1 carbon atom]
Represents an alkyl group having 10 to 10 or a cycloalkyl group having 3 to 10 carbon atoms. i, j, k and l are the same or different and are 0 to
It represents an integer of 17, and i + j + k + l = 13 to 17. ]

In the general formulas (1) to (4), the position of the alkoxy group may be any position.

The alkoxy residues (R ^{1 to} R ⁷ ) include linear or branched alkyl groups such as methyl group, ethyl group, propyl group and butyl group and cycloalkyl groups such as cyclopentyl group and cyclohexyl group. Is exemplified.

The monoalkoxy fatty acid represented by the general formula (2) includes 9-methoxystearic acid, 9-ethoxystearic acid, 9-n-propyloxystearic acid, 9-n-butoxystearic acid, 9-tert. -Butoxystearic acid, 9-cyclohexyloxystearic acid, 10-methoxystearic acid, 10-ethoxystearic acid, 10-n-propyloxystearic acid, 1
Examples thereof include 0-n-butoxystearic acid, 10-tert-butoxystearic acid, 10-cyclohexyloxystearic acid, 13-methoxybehenic acid and 14-methoxybehenic acid.

The dialkoxy fatty acid represented by the general formula (3) includes 9,12-dimethoxystearic acid and 1
Examples are 0,13-dimethoxystearic acid and the like.

Examples of the trialkoxy fatty acid represented by the general formula (4) include 9,12,15-trimethoxystearic acid and 10,13,16-trimethoxystearic acid.

The fatty acid derivative according to the present invention can be produced, for example, by an oxymercuration-demercuration reaction. That is, a predetermined unsaturated fatty acid alkyl and alcohol are added in the presence of Hg (II) at 0 to 100 ° C., preferably 2
The reaction is carried out at 0 to 50 ° C for 0.5 to 8 hours, preferably 1 to 30 hours, followed by 0-1 with sodium borohydride.
A predetermined alkoxy fatty acid is produced by reduction at 00 ° C, preferably 20 to 50 ° C for 0.5 to 8 hours, preferably 1 to 3 hours.

The amount of alcohol used in this reaction is 1 to 1000 equivalents, preferably 10 to 100 equivalents, per mole of unsaturated fatty acid alkyl.

Examples of Hg (II) include mercury acetate and mercury trifluoroacetate, and the amount thereof is 1 to 20 equivalents, preferably 1 to 5 equivalents, relative to 1 mol of the unsaturated fatty acid alkyl.
It is equivalent.

The various alkoxy fatty acids thus obtained serve as novel liquid fatty acid derivatives and serve as raw materials for cosmetics, lubricating oils, and various ester raw materials.

[0020]

EXAMPLES The present invention will be specifically described below with reference to examples.

Example 1 In a 200 ml four-necked flask equipped with a thermometer, a gas inlet and a stirrer, 5.0 g (17 mmol) of methyl oleate, 5.4 g (17 mmol) of mercury (II) acetate and Add 40 ml of methanol, and under nitrogen atmosphere, at room temperature 1.5.
Stir for hours. 20 ml of 3N-sodium hydroxide aqueous solution and then 20 ml of 0.5M-sodium borohydride 3N-sodium hydroxide aqueous solution were added, and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the mixture was filtered, and the obtained filtrate was neutralized with a dilute hydrochloric acid aqueous solution, extracted with ether, and washed twice with a saturated sodium chloride aqueous solution. After distilling off the solvent, methanol 80m
0.01 g of 1, -p-toluenesulfonic acid was added and refluxed for 2 hours to return to methyl ester.

Methyl 9-methoxystearate was isolated by means of preparative high performance liquid chromatography, to which 1.5 g of sodium hydroxide and 15 m of tetrahydrofuran were added.
l, 30 ml of methanol and 1 ml of water were added, and the mixture was refluxed for 1.5 hours for hydrolysis to obtain 9-methoxystearic acid. The yield was 42.0%.

The characteristic values are as follows, and the structure of R ² = CH ₃ in the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2928 (CH), 2856 (CH),
1711 (C = O), 1465, 1377, 1197,
1098 (C-O-C), 938

¹ NMR (CDCl ₃ , δppm) 11.1 (1H, brs, OH ), 3.22 (3H,
s, O CH ₃ ), 3.13 (1H, m, O CH ),
2.35 (2H, t, CH ₂ CO ₂ H), 1.64 (2
_{H, m, CH 2),} 1.38~1.51 (4H, br
m, CH ₂ × 2) 1.22 to 1.38 (22H, br
m, CH ₂ × 11), 0.89 (3H, t, CH ₃ ).

Melting point: 1.6 ° C., cloud point: −43 ° C.

Example 2 The same operation as in Example 1 was carried out except that methanol was ethanol and the reaction temperature of methyl oleate and alcohol was 30 ° C. The yield of 9-ethoxystearic acid was 39.2%.

The characteristic values are as follows, and the structure of R ² ═CH ₃ CH ₂ in the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2927 (CH), 2856 (CH),
1713 (C = O), 1466, 1413, 1373,
1343, 1285, 1111 (C-O-C), 939

¹ NMR (CDCl ₃ , δppm) 11.1 (1H, brs, OH ), 3.48 (2H,
q, O CH ₂ ), 3.20 (1H, m, O CH ),
2.35 (2H, t, CH ₂ CO ₂ H), 1.64 (2
_{H, m, CH 2),} 1.38~1.51 (4H, br
m, CH ₂ × 2), 1.22 to 1.38 (22H, br
m, CH ₂ × 11), 1.19 (3H, t, OCH ₂ C
_{H 3), 0.89 (3H,} t, CH 3)

Melting point: -0.7 ° C, cloud point: -50 ° C

Example 3 Example 2 was repeated except that ethanol was n-propanol and the reaction between methyl oleate and alcohol was 4 hours.
The same operation was performed. The yield of 10-n-propyloxystearic acid was 37.6%.

The characteristic values are as follows, and the structure of R ² ═CH ₃ (CH ₂ ) _{2 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2927 (CH), 2856 (CH),
1713 (C = O), 1465, 1377, 1284,
1090 (C-O-C), 938

¹ NMR (CDCl ₃ , δppm) 10.6 (1H, brs, OH ), 3.37 (2H,
t, O CH ₂ ), 3.19 (1H, m, O CH ),
2.35 (2H, t, CH ₂ CO ₂ H), 1.63 (2
H, m, CH ₂ ), 1.57 (2H, m, OCH ₂ C
H ₂ ), 1.38 to 1.51 (4H, brm, CH ₂ ×
2), 1.22 to 1.38 (22H, brm, CH ₂ ×
11), 0.93 (3H, t, CH ₃ ), 0.89 (3
H, t, CH ₃ )

Melting point: -49.0 ° C, cloud point: -53 ° C

Example 4 The same operation as in Example 3 was carried out except that n-butanol was used as the n-propanol. The yield of 10-n-butoxystearic acid was 35.6%.

The characteristic values are as follows, and the structure of R ² = CH ₃ (CH ₂ ) _{3 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2928 (CH), 2856 (CH),
1712 (C = O), 1466, 1378, 1285,
1096 (C-O-C), 937

¹ NMR (CDCl ₃ , δppm) 10.8 (1H, brs, OH ), 3.41 (2H,
t, O CH ₂ ), 3.18 (1H, m, O CH ),
2.35 (2H, m, CH ₂ CO ₂ H), 1.64 (2
H, m, CH ₂ ), 1.54 (2H, m, OCH ₂ C
H ₂ ), 1.22 to 1.51 (28H, brm, CH ₂ ×
14), 0.92 (3H, t, CH ₃ ), 0.89 (3
H, t, CH ₃ )

Melting point: −23.1 ° C., cloud point: −60 ° C.

Example 5 Using n-butanol as tert-butanol, mercury acetate (I
The same operation as in Example 3 was performed except that I) was changed to 6.3 g (17 mmol) of mercury (II) trifluoroacetate. The yield of 10-tert-butoxystearic acid is 35.
It was 4%.

The characteristic values are as follows, and the structure of R ² = C (CH ₃ ) _{3 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2928 (CH), 2856 (CH),
1712 (C = O), 1464, 1392, 1367,
1285, 1096 (C-O-C), 937

¹ NMR (CDCl ₃ , δppm) 10.8 (1H, brs, OH ), 3.15 (1H,
m, O CH ), 2.35 (2 H, m, CH ₂ CO ₂ H),
_{1.64 (2H, m, CH 2} ), 1.38~1.51
(4H, brm, CH ₂ × 2), 1.22 to 1.38
(22H, br m, CH ₂ × 11), 1.20 (9
H, s, CH ₃ × 3), 0.89 (3H, t, CH ₃ ).

Melting point: −25.3 ° C., cloud point: −58 ° C.

Example 6 The same operation as in Example 1 was carried out except that methyl oleate was changed to 6.0 g (17 mmol) of methyl erucate.
The yield of 13-methoxybehenic acid was 40.1%.

The characteristic values are as follows, and the structure of R ² = CH ₃ in the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2928 (CH), 2856 (CH),
1712 (C = O), 1464, 1375, 1197,
1099 (C-O-C), 938

¹ NMR (CDCl ₃ , δppm): 11.1
(1H, brs, OH ), 3.22 (3H, s, O CH
₃ ), 3.15 (1H, m, O CH ), 2.35 (2
H, t, CH ₂ CO ₂ H), 1.64 (2H, m, C
H ₂ ), 1.38 to 1.51 (4H, brm, CH ₂ ×
2) 1.22 to 1.38 (30H, brm, CH ₂ × 1
5), 0.89 (3H, t , CH 3)

Melting point: 12.3 ° C.

Example 7 Methyl oleate was changed to methyl linoleate, and 10.8 g (34 mmol) of mercury (II) acetate and 70% of methanol were used.
The same operation as in Example 1 was performed except that the amount was changed to ml. 9,
The yield of 12-dimethoxystearic acid was 39.0%.

The characteristic values are as follows, and the structure of R ³ = R ⁴ = CH ₃ in the general formula (3) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2929 (CH), 2856 (CH),
1711 (C = O), 1466, 1376, 1199,
1098 (C-O-C), 939

¹ NMR (CDCl ₃ , δppm): 11.1
(1H, brs, OH ), 3.22 (6H, s, OCH
₃ x 2), 3.13 (2H, m, OCH x 2), 2.3
5 (2H, t, CH ₂ CO ₂ H), 1.64 (2H, m,
CH ₂ ), 1.38 to 1.52 (8H, brm, CH ₂ ×
4), 1.22 to 1.38 (16H, brm, CH ₂ ×
8), 0.89 (3H, t , CH 3)

Melting point: -32.8 ° C

Example 8 Methyl oleate was changed to methyl linolenate, and 16.2 g (51 mmol) of mercury (II) acetate and 10 parts of methanol were used.
The same operation as in Example 1 was performed except that the amount was 0 ml.
The yield of 9,12,15-trimethoxystearic acid is 3
It was 6.1%.

The characteristic values are as follows, and the structure of R ⁵ = R ⁶ = R ⁷ = CH _{3 in} the general formula (4) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2927 (CH), 2856 (CH),
1710 (C = O), 1465, 1378, 1200,
1099 (C-O-C), 938

¹ NMR (CDCl ₃ , δppm): 11.1
(1H, brs, OH), 3.22 (9H, s, O CH
₃ x 3), 3.13 (3H, m, OCH x 3), 2.3
5 (2H, t, CH ₂ CO ₂ H), 1.64 (2H, m,
CH ₂ ), 1.36 to 1.52 (12H, brm, CH ₂
× 6), 1.22 to 1.36 (10H, brm, CH ₂
× 5), 0.89 (3H, t, CH 3)

Melting point: 41.5 ° C.

Example 9 except that cyclohexanol was used as the tert-butanol,
The same operation as in Example 5 was performed. The yield of 9-cyclohexyloxystearic acid was 37.1%.

The characteristic values are as follows, and the structure of R ² = cyclohexyl in the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2927 (CH), 2855 (CH),
1714 (C = O), 1465, 1374, 1285,
1095 (C-O-C), 939

¹ NMR (CDCl ₃ , δppm) 11.1 (1H, brs, OH ), 3.25 (1H,
m, O CH ), 3.19 (1H, m, O CH ), 2.3
5 (2H, t, CH ₂ CO ₂ H), 1.63 (2H, m,
CH ₂ ), 1.38 to 1.51 (4H, brm, CH ₂ ×
2), 1.22 to 1.38 (32 H, brm, CH ₃
× 16), 0.89 (3H, t, CH 3)

Melting point: −24.7 ° C., cloud point: −62 ° C.

Example 10 5 g of methyl 12-hydroxystearate was placed in a 100 ml four-necked flask equipped with a thermometer, a gas inlet and a stirrer.
(16 mmol), 0.6 g (16 mmol) of 60% sodium hydride washed with n-hexane, and 20 ml of dimethylformamide dried and distilled over calcium hydride were added, and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hours. Then, 5 ml of ethyl iodide was added and the mixture was further stirred for 6 hours. After completion of the reaction, the mixture was neutralized with a dilute aqueous hydrochloric acid solution, extracted with ether, and washed twice with a saturated aqueous sodium chloride solution. After distilling off the solvent, silica gel column chromatography (2.7φ ×
43 cm, developing solvent (volume ratio): n-hexane / ethyl acetate = 20/1) was used to isolate methyl 12-ethoxystearate, to which 1.5 g of sodium hydroxide, 15 ml of tetrahydrofuran, 30 ml of methanol, 1 ml of water were added. By refluxing for 1.5 hours to hydrolyze 12-
Ethoxystearic acid was obtained. The yield was 76.2%.

The characteristic values are as follows, and the structure of R ² ═CH ₃ CH ₂ in the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2927 (CH), 1713 (C =
O), 1466, 1373, 1284, 1111 (C-
OC), 939

¹ NMR (CDCl ₃ , δppm): 11.0
(1H, brs, OH ), 3.48 (2H, q, O CH
₂ ), 3.21 (1H, quint, CH ), 2.35.
(2H, t, CH ₂ CO ₂ H), 1.64 (2H, qui
nt, CH ₂ CH ₂ CO ₂ H), 1.5 to 1.2 (26
H, brm, CH x 13), 1.20 (3H, t, OC
_{H 2 CH 3), 0.90 (} 3H, t, CH 3)

Melting point: 13.5 ° C.

Example 11 The same operation as in Example 10 was carried out except that ethyl iodide was changed to n-propyl iodide. The yield of the obtained 12-n-propoxystearic acid was 71.8%.

The characteristic values are as follows, and the structure of R = CH ₃ (CH ₂ ) _{2 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2928 (CH), 2856 (CH),
1713 (C = O), 1465, 1377, 1283
1091 (C-O-C), 939

¹ NMR (CDCl ₃ , δppm): 10.9
(1H, brs, OH ), 3.37 (2H, t, O CH
₂ ), 3.20 (1H, quint, CH ), 2.35.
(2H, t, CH ₂ CO ₂ H), 1.64 (2H, qui
nt, CH ₂ CH ₂ CO ₂ H), 1.57 (2H, m, O
CH ₂ CH ₂ ), 1.5 to 1.2 (26H, brm, CH
× 13), 0.93 (3H, t, O (CH ₂ ) ₂ C
_{H 3), 0.89 (3H,} t, CH 3)

Melting point: -11.9 ° C

Example 12 Example 1 was repeated except that ethyl iodide was changed to n-butyl iodide.
The same operation as 0 was performed. The yield of the obtained 12-n-butoxystearic acid was 70.1%.

The characteristic values are as follows, and the structure of R = CH ₃ (CH ₂ ) _{3 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2927 (CH), 2856 (CH),
1713 (C = O), 1466, 1378, 1284,
1097 (C-O-C), 940

[0080]¹NMR (CDCl₃, Δppm): 11.1
(1H, brs,OH), 3.41 (2H, t, OCH
₂ ), 3.19 (1H, quint,CH) 2.35
(2H, t,CH ₂ CO₂H), 1.64 (2H, qui
nt,CH ₂ CH₂CO2H), 1.54 (2H, qui
nt, OCH₂ CH ₂ ), 1.5 to 1.2 (28H, br
m,CH× 14), 0.92 (3H, t, O (CH₂)₃
CH ₃ ), 0.89 (3H, t,CH ₃ )

Melting point: -6.9 ° C

Example 13 The reaction was performed in the same manner as in Example 3 except that methyl oleate was changed to methyl 2-octadecenoate, and after the reaction was completed, the mixture was filtered, and the obtained filtrate was neutralized with a dilute aqueous hydrochloric acid solution and extracted with ether. After that, it was washed twice with a saturated sodium chloride aqueous solution.
After the solvent was distilled off, 80 ml of methanol and 0.01 g of p-toluenesulfonic acid were added, and the mixture was refluxed for 2 hours to restore the methyl ester. Silica gel column chromatography (2.7φ × 43 cm, developing solvent (volume ratio): n-hexane / ethyl acetate = 20/1) was used to isolate methyl 3-n-propoxystearate, and 1.5 g of sodium hydroxide was added thereto. , Tetrahydrofuran 15 ml, methanol 30
ml and water (1 ml) were added, and the mixture was refluxed for 1.5 hours for hydrolysis to obtain 3-n-propoxystearic acid. The yield was 72.7%.

The characteristic values are as follows, and the structure of R = CH ₃ (CH ₂ ) _{2 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2926 (CH), 2854 (CH),
1713 (C = O), 1466, 1378, 1298,
1095 (C-O-C), 938

¹ NMR (CDCl ₃ , δppm): 11.0
(1H, brs, OH ), 3.70 (0.5H, qui)
nt, CH), 3.5~3.4 (2H , m, O C
H ₂ ), 3.36 (0.5H, m, CH ), 2.6-
2.4 (2H, m, CH ₂ O ₂ H), 1.6 to 1.5 (2
_{H, m, OCH 2 CH 2} ), 1.3~1.2 (28H, b
rm, CH ₂ × 14), 0.94 (3H, t, OCH ₂ C
_{H 2 CH 3), 0.89 (} 3H, t, CH 3)

Melting point: 5.6 ° C.

Example 14 The same operation as in Example 13 was carried out except that n-butanol was used as the n-propanol. The yield of the obtained 3-n-butoxystearic acid was 68.5%.

The characteristic values are as follows, and the structure of R = CH ₃ (CH ₂ ) _{3 in} the general formula (2) is supported.

IR (NaCl, cm ^-1 ): 3300-25
00 (OH), 2925 (CH), 2855 (CH),
1713 (C = O), 1466, 1378, 1295,
1099 (C-O-C), 937

¹ NMR (CDCl ₃ , δppm): 11.1
(1H, brs, OH ), 3.69 (0.5H, m, C
H ), 3.6-3.5 (0.5H, m, CH 2; 2H,
m, O CH ₂ ), 2.6 to 2.4 (2H, m, CH ₂ CO
₂ H), 1.6 to 1.5 (2 H, m, OCH ₂ CH ₂ ),
1.3 to 1.2 (28H, brm, CH ₂ × 14),
0.93 (3H, t, O ( CH 2) 3 CH 3), 0,89
(3H, t, CH ₃ )

Melting point: -1.3 ° C

[0092]

The alkoxy fatty acid derivative according to the present invention is a novel and useful liquid fatty acid, and its major characteristics are
It has excellent oxidative and thermal stability and is free from odor.

Claims (4)

[Claims] 1. A liquid fatty acid derivative represented by the general formula (1). _{CH 3 (CH 2) a- [} CH (-OR 1) - (CH 2) c] b
-COOH (1) [wherein, R ¹ represents a cycloalkyl group alkyl or 3-10 carbon atoms having 1 to 10 carbon atoms. a and c are the same or different and represent an integer of 0 to 19, and a + c = 13 to 19. b represents an integer of 1 to 3. ] 2. The liquid fatty acid derivative according to claim 1, which is represented by the general formula (2). _{CH 3 (CH 2) d-} CH (-OR 2) - (CH 2) e-CO
OH (2) [In the formula, R ² represents an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms. d and e are the same or different and represent an integer of 0 to 19, and d + e = 15 to 19. ] 3. The liquid fatty acid derivative according to claim 1, which is represented by the general formula (3). _{CH 3 (CH 2) f-} CH (-OR 3) - (CH 2) g-CH
(-OR ⁴ ) * *-(CH ₂ ) h-COOH
(3) [In the formula, R ³ and R ⁴ are the same or different and are an alkyl group having 1 to 10 carbon atoms or 3 to 10 carbon atoms.
Represents a cycloalkyl group. f, g, and h are the same or different and represent an integer of 0 to 18, and f + g + h = 14 to
Eighteen. ] 4. The liquid fatty acid derivative according to claim 1, which is represented by the general formula (4). _{CH 3 (CH 2) i-} CH (-OR 5) - (CH 2) j-CH
^{(-OR 6) ** - (CH} 2) k-CH (-OR 7) - (C
_{H 2) l-COOH (4} ) [ wherein, R ^5, R ^6,
R ⁷ is the same or different and represents an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms. i,
j, k, and l are the same or different and represent an integer of 0 to 17, and i + j + k + l = 13 to 17. ]