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Dibasic acid diester

A dibasic acid diester and alkyl technology, applied in organic chemistry, lubricating compositions, base materials, etc., can solve the problems that the hydrolysis resistance cannot meet the practical requirements, and achieve the effect of excellent hydrolysis resistance

Inactive Publication Date: 2005-01-12
KYOWA HAKKO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, any of the above-mentioned lubricating oils using polycarboxylic acid diesters as base oils cannot meet practical requirements in terms of hydrolysis resistance.

Method used

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Examples

Experimental program
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Effect test

reference example 1

[0038] 160.3 g of 2,4-diethyl-1,5-pentanediol (trade name: Kyowa Diol (キヨ-ヮジォ-ル) PD-9, manufactured by Kyowa Oil & Chemical Co., Ltd., purity 93.9%), hydrogenated 156.6 g of potassium (purity 86%), 102.2 g of a paraffin wax mixture with 12 carbon atoms (trade name: Kyowa Sol (キヨ-ヮゾ-ル) C1200-H, manufactured by Kyowa Oil Chemical Co., Ltd.) Heating and stirring were performed at 1 MPa in a 1 L nickel autoclave with a pressure control valve and an electric furnace capable of controlling the temperature. The hydrogen gas produced was measured with a gas meter to track the progress of the reaction. Gas generation was confirmed at around 230°C, and the reaction was continued at 250 to 270°C. From reaching 250°C until 3.5 hours, 89.4L of hydrogen gas was generated, and the reaction was continued for 30 minutes, during which 0.8L of hydrogen gas was generated. The amount of hydrogen gas generated was consistent with the theoretical value, and the reaction rate was 100%. After the re...

Embodiment 1

[0039] Embodiment 1: the synthesis of 2,4-diethylglutaric acid bis(2-ethylhexyl) (compound 1)

[0040]Put 2,4-diethylglutaric acid (92.50g), 2-ethylhexanol (66.00g) and toluene (157.3g) into the reaction flask, after stirring thoroughly, add p-toluenesulfonic acid monohydrate (2.67g), refluxed for 5 hours. Cool to room temperature, neutralize with 0.1% by weight aqueous sodium hydroxide solution, and distill off the solvent at 135° C. under vacuum from the water-washed reaction solution to obtain 146 g of compound 1 (yield: 98.4%). The physical properties of this compound are as follows:

[0041] 1 H-NMR (CDCl 3 , δppm): 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)

[0042] IR (cm -1 ): 2972, 2942, 2887(C-H), 1745(C=O), 1465, 1388, 1261, 1163(C-O)

[0043] MS (m / z): 414 (M + )

[0044] Density (kg / m 3 ): 929 (25°C)

[0045] Dynamic viscosity (cSt): 9.47 (40°C), 2.53 (100°C)

Embodiment 2

[0046] Example 2: Synthesis of 2,4-diethylglutaric acid bis[5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)octyl] (compound 2)

[0047] 2,4-diethylglutaric acid (92.06g), 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl) octanol (28.32g) and toluene ( 30.23 g) into the reaction flask, and after fully stirring, p-toluenesulfonic acid monohydrate (1.13 g) was added and refluxed for 4 hours. Cool to room temperature, neutralize with 0.2% by weight aqueous sodium hydroxide solution, and remove 5,7,7-trimethyl-2-(1,3,3 - Trimethylbutyl) octanol to obtain 82.9 g of compound 2 (yield: 79.0%).

[0048] The physical properties of compound 2 are as follows:

[0049] 1 H-NMR (CDCl 3 , δppm): 4.01 (m, 4H), 2.32 (m, 2H), 1.96-1.04 (m, 28H), 0.88 (m, 54H)

[0050] IR (cm -1 ): 2962, 2916, 2887(C-H), 1743(C=O), 1471, 1384, 1233, 1197, 1164(C-O)

[0051] Density (kg / m 3 ): 879 (26°C)

[0052] Dynamic viscosity (cSt): 270 (40°C), 14.3 (100°C)

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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 R<2> and R<3>, which may be the same or different, each represent lower alkyl; and R<1> and R<4>, 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. Background technique [0002] In lubricating oils and greases, it is desirable to use base oils with high stability and long service life. [0003] As base oils of lubricating oils and greases, for example, dibasic acid diester-containing base oils and the like are known. As a lubricating oil comprising a dibasic acid diester as a base oil, there is known a lubricating oil comprising an alicyclic polycarboxylic acid ester as a base oil disclosed in WO97 / 21792. In addition, JP-A-2001-89776 discloses a lubricating oil for refrigerators that uses 1,2-cyclohexanedicarboxylic acid diester as a base oil. However, none of the above-mentioned lubricating oils using polycarboxylic acid diesters as base oils cannot meet practical requirements in terms of hydrolysis resistance. Contents of the invention [0004] An object of the present invention is to provide a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/34C10M105/36
CPCC10M2207/2825C10N2230/66C10M2207/345C07C69/34C10N2220/10C10M105/36C10N2230/64C10M2207/2855C10N2020/081C10N2030/64C10N2030/66
Inventor 福田行俊清水几夫伊东克浩长田和耕
Owner KYOWA HAKKO CHEM CO LTD