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Method for preparing low-acid-value trimethylolpropane trioleate

A technology of methylolpropane oleate and trimethylolpropane, which is applied in the field of preparing trimethylolpropane oleate with low acid value, can solve the problem of shortening the service life of machinery, methods that have not been reported in literature, and mechanical lubrication systems Faster loss and other issues, to achieve the effect of easy implementation, stable performance, and simple operation

Pending Publication Date: 2018-10-26
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In Chinese patent ZL02111552.4, solid oxides are used to catalyze the esterification reaction of oleic acid and trimethylolpropane, and then high temperature and high vacuum (20-100Pa) are used to remove residual oleic acid with a yield of 92%. No product is reported acid value
Due to corrosion of metals, the loss of the mechanical lubrication system is accelerated and the service life of the machine is shortened
[0007] The prior art shows that the synthesis and deacidification methods of trimethylolpropane trioleate have been reported in the literature, but the method for obtaining products with an acid value of less than 0.1mgKOH / g through the reaction has not been reported in the literature

Method used

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  • Method for preparing low-acid-value trimethylolpropane trioleate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 67.1g (0.5mol) of trimethylolpropane and 409.6g (1.45mol) of oleic acid to the reactor successively, add the catalyst p-toluenesulfonic acid, petroleum ether with water agent, and control the heating temperature of the oil bath to 130-135°C , under the protection of nitrogen, stir and reflux, divide the water for 3.0~4.0 hours, cool, add 5.1g acetic anhydride (0.05mol), heat the oil bath to 55~60°C, and stir for 1 hour. After the reaction was complete, cool to room temperature, wash with water, and vacuum remove the water-carrying agent from the organic layer to obtain a light yellow oily transparent liquid with an acid value of 0.06 mgKOH / g and a yield of 99%.

Embodiment 2

[0025] Add 67.1g (0.5mol) of trimethylolpropane and 409.6g (1.45mol) of oleic acid to the reactor successively, add the catalyst p-toluenesulfonic acid, petroleum ether with water agent, and control the heating temperature of the oil bath to 130-135°C , under the protection of nitrogen, stir and reflux, divide the water for 3.0~4.0 hours, cool, add 6.5g propionic anhydride (0.05mol), heat the oil bath to 55~60°C, and stir for 1 hour. After the reaction was complete, cool to room temperature, wash with water, and remove the water-carrying agent from the organic layer in vacuum to obtain a light yellow oily transparent liquid with an acid value of 0.07 mgKOH / g and a yield of 99%.

Embodiment 3

[0027] Add 67.1g (0.5mol) of trimethylolpropane and 416.6g (1.475mol) of oleic acid to the reactor successively, add the catalyst p-toluenesulfonic acid, petroleum ether with water agent, and control the heating temperature of the oil bath to 130-135°C , under the protection of nitrogen, stir and reflux, divide the water for 3.0~4.0 hours, cool, add 4.0g acetic anhydride (0.025mol), heat the oil bath to 55~60°C, and stir for 1 hour. After the reaction was complete, cool to room temperature, wash with water, and vacuum remove the water-carrying agent from the organic layer to obtain a light yellow oily transparent liquid with an acid value of 0.08 mgKOH / g and a yield of 99%.

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Abstract

The invention discloses a method for preparing low-acid-value trimethylolpropane trioleate. The method is characterized by comprising the following steps: step I, adding oleic acid and trimethylolpropane in a molar ratio less than 3, and performing the reaction in the presence of a catalyst and a water-carrying agent; step II, adding small-molecular-weight acid anhydride, completely closing the unreacted hydroxyl, and obtaining a mixture of trihydroxymethylpropyl trioleate and trimethylolpropane dioleate small-molecular carboxylic ester; step III, after the reaction is completed, cooling to the room temperature, washing, vacuum removing the water-carrying agent from an organic layer, and obtaining the light-yellow oily transparent liquid trimethylolpropane trioleate. According to the method, the esterification is divided into two steps, in the final esterification step, the small-molecular-weight carboxylic acid is adopted and can be directly removed in a washing manner, the obtained product only contains little trimethylolpropane dioleic acid small-molecular-weight acid ester, the acid value is less than 0.1 mgKOH / g, and the quality is far higher than that of the same variety in the market.

Description

technical field [0001] The invention relates to the field of fine organic chemical industry, in particular to a method for preparing trimethylolpropane oleate with low acid value. Background technique [0002] Trimethylolpropane oleate has a high biodegradation rate and is a green ester lubricant with excellent lubricating properties, high viscosity index, high flash point, good hydrolytic stability, low volatility, and good low temperature fluidity. Trimethylolpropane oleate with low acid value and high quality can be used to blend ester-type fire-resistant hydraulic oil, environmentally friendly hydraulic oil and engine oil for water yachts. [0003] The synthesis of trimethylolpropane trioleate has two kinds of methods, and the first kind is the transesterification (Xing Fenglan etc. of methyl oleate and trimethylolpropane TMP, fine and specialty chemicals, 2007,15 (18) : 16-18 pages), the second is obtained through esterification of TMP and oleic acid. The second metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/58
CPCC07C67/08C07C69/58
Inventor 廖德仲廖嘉树
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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