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Dibasic acid diesters

Inactive Publication Date: 2005-06-16
KYOWA HAKKO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0004] An object of the present invention is to provide dibasic acid diesters, which are suitable for use in lubricating base oils, etc. and excellent in hydrolysis resistance, etc.
[0022] The lubricating base oil and the lubricating oil of the present invention are excellent in hydrolysis resistance, lubrication, heat resistance, low temperature fluidity, flame resistance, biodegradability, or the like.

Problems solved by technology

However, neither of the above lubricating oils whose base oil is a polycarboxylic acid diester is practically satisfactory in respect of hydrolysis resistance.

Method used

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Examples

Experimental program
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Effect test

reference example 1

[0032] 2,4-Diethyl-1,5-pentanediol (160.3 g) (trade name: Kyowadiol PD-9, Kyowa Yuka Co., Ltd., purity: 93.9%), 156.6 g of potassium hydroxide (purity: 86%) and 102.2 g of carbon number 12 paraffin mixture (trade name: Kyowasol C1200-H, Kyowa Yuka Co., Ltd.) were placed in a 1L nickel autoclave equipped with a reflux condenser, a pressure control valve and an electric furnace capable of temperature control, and heated with stirring under 1 MPa. The generated hydrogen gas was measured with a gas meter, and the progress of reaction was monitored. The generation of the gas was confirmed at around 230° C., and the reaction was continued at a temperature maintained in the range of 250 to 270° C. After the temperature reached 250° C., 89.4 l of hydrogen was generated in 3.5 hours. The reaction was continued for further 30 minutes, during which 0.8 l of hydrogen gas was generated. The amount of the generated hydrogen agreed with the theoretical value and the rate of reaction was 100%. Afte...

example 1

Synthesis of bis(2-ethylhexyl) 2,4-diethylglutarate (Compound 1)

[0033] In a reaction flask were placed 2,4-diethylglutaric acid (92.50 g), 2-ethylhexanol (66.00 g) and toluene (157.3 g), and the mixture was stirred well and p-toluenesulfonic acid monohydrate (2.67 g) was added thereto, followed by reflux for 5 hours. After cooling to room temperature, the reaction mixture was neutralized with a 0.1 wt % aqueous solution of sodium hydroxide and then washed with water. The solvent was distilled away from the reaction mixture at 135° C. in vacuo, whereby 146 g of Compound 1 (yield: 98.4%) was obtained. The physical properties of Compound 1 were as follows. [0034]1H-NMR (CDCl3, δ ppm): 3.98 (m, 4H), 2.32 (m, 2H), 1.94 (m, 1H), 1.75 (m, 1H), 1.59 (m, 4H), 1.28 (m, 18H), 0.95 (m, 18H) [0035] IR (cm−1): 2972, 2942, 2887 (C—H), 1745 (C═O), 1465, 1388, 1261, 1163 (C—O) [0036] MS (m / z): 414 (M+) [0037] Density (kg / m3): 929 (25° C.) [0038] Kinematic viscosity (cSt): 9.47 (40° C.), 2.53 (100° ...

example 2

Synthesis of bis[5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)octyl]2,4-diethylglutarate (Compound 2)

[0039] In a reaction flask were placed 2,4-diethylglutaric acid (92.06 g), 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)octyl alcohol (28.32 g) and toluene (30.23 g), and the mixture was stirred well and p-toluenesulfonic acid monohydrate (1.13 g) was added thereto, followed by reflux for 4 hours. After cooling to room temperature, the reaction mixture was neutralized with a 0.2 wt % aqueous solution of sodium hydroxide and then washed with water. 5,7,7-Trimethyl-2-(1,3,3-trimethylbutyl)octyl alcohol was removed from the reaction mixture by extraction with methanol (three times), whereby 82.9 g of Compound 2 (yield: 79.0%) was obtained. The physical properties of Compound 2 were as follows. [0040]1H-NMR (CDCl3, δ ppm): 4.01 (m, 4H), 2.32 (m, 2H), 1.96-1.04 (m, 28H), 0.88 (m, 54H) [0041] IR (cm−1): 2962, 2916, 2887 (C—H), 1743 (C═O), 1471, 1384, 1233, 1197, 1164 (C—O) [0042] Density (kg / m3): 8...

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Abstract

The present invention provides dibasic acid diesters, which are suitable for use in lubricating base oils, etc. and excellent in hydrolysis resistance, etc., represented by general formula (I): (wherein R2 and R3, which may be the same or different, each represent lower alkyl; and R1 and R4, which may be the same or different, each represent alkyl having 7 or more carbon atoms).

Description

TECHNICAL FIELD [0001] The present invention relates to dibasic acid diesters suitable for use in lubricating base oils, etc. BACKGROUND ART [0002] As base oils for lubricating oils and grease, those having a high stability and a long life are desirable. [0003] Known examples of the base oils for lubricating oils or grease include those comprising dibasic acid diesters. As the lubricating oil whose base oil is a dibasic acid diester, WO97 / 21792 discloses a lubricating oil whose base oil is an alicyclic polycarboxylic acid ester, and Japanese Published Unexamined Patent Application No. 2001-89776 discloses a lubricating oil for a freezer whose base oil is 1,2-cyclohexanedicarboxylic acid diester. However, neither of the above lubricating oils whose base oil is a polycarboxylic acid diester is practically satisfactory in respect of hydrolysis resistance. DISCLOSURE OF THE INVENTION [0004] An object of the present invention is to provide dibasic acid diesters, which are suitable for us...

Claims

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Application Information

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IPC IPC(8): C07C69/34C10M105/36
CPCC07C69/34C10M105/36C10M2207/2825C10N2230/66C10M2207/345C10N2220/10C10N2230/64C10M2207/2855C10N2020/081C10N2030/64C10N2030/66
Inventor FUKUDA, YUKITOSHISHIMIZU, IKUOITO, KATSUHIROOSADA, KAZUYASU
Owner KYOWA HAKKO CHEM CO LTD
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