CN104672085A - Synthesis of trimethylolpropane organic acid ester and application in special oil - Google Patents
Synthesis of trimethylolpropane organic acid ester and application in special oil Download PDFInfo
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Abstract
The invention discloses a synthesis method of trimethylolpropane organic acid ester, which is characterized by comprising the following steps of: taking organic acid and organic alcohol as raw material, further adding proper amount of catalyst, reacting for 3-5 hours under normal pressure at 110-130 DEG C, thereby obtaining the trimethylolpropane organic acid ester; the organic acid is selected from any one of Oleic acid, lauric acid, octanoic acid, stearic acid and palmitic acid, the organic alcohol is trimethylolpropane, and molar ratio of organic acid to organic alcohol is 1:3; the catalyst is N-alkyl pyrrolidone group methyl phosphate ion liquid catalyst. In the synthesis method, the N-alkyl pyrrolidone group methyl phosphate ion liquid catalyst is selected for synthesizing the trimethylolpropane organic acid ester, the synthesis method has the characteristics of low reaction temperature, small dosage of catalyst, short reaction time, high esterification rate, and so on, and products produced by the synthesis method has small acid value.
Description
Technical field
The present invention relates to chemical field, specifically a kind of synthesis of TriMethylolPropane(TMP) organic acid acetic and the application in extraordinary oil.
Background technology
TriMethylolPropane(TMP) organic acid acetic (Trimethylolpropane trioleate) is referred to as TMPTO, it has the excellent abrasion resistance of synthesizing ester. there are excellent viscosity-temperature characteristics, good cold property, high-temperature stability, low volatility, thus can meet higher lubricating requirement, be particluarly suitable for the application in extraordinary oily industry.
TriMethylolPropane(TMP) organic acid acetic has that lubricity is excellent, viscosity index is high, non-flame properties is good, the characteristics such as biological degradation rate is high, toxicity is low, it is a kind of Green Lubricants, it widely uses in cold rolling sheet rolling oil, steel pipe drawing oil, machining oil and other metal working fluid as oiliness improver, and TriMethylolPropane(TMP) organic acid acetic also can be used as intermediate and the textile finish oil of leather auxiliary agent.
The synthetic method of existing TriMethylolPropane(TMP) organic acid acetic mainly contains direct esterification and ester-interchange method, these method many uses protonic acid, metal oxide, inorganic salt catalysts etc., synthesis method is not that temperature of reaction is high, it is exactly long reaction time, and low conversion rate, poor product quality, equipment corrosion are serious, post-reaction treatment is difficult, spent acid is seriously polluted.
Summary of the invention
The weak point that the present invention exists in order to avoid prior art, provides a kind of synthesis of hydroxymethyl-propane oleic acid ester and the application in extraordinary oil.
Technical solution problem of the present invention adopts following technical scheme:
The synthetic method of TriMethylolPropane(TMP) organic acid acetic, its feature is, with organic acid and Organic Alcohol for raw material, and add proper catalyst, synthesis under normal pressure 3-5 hour under 110 DEG C of-130 DEG C of conditions, obtains TriMethylolPropane(TMP) organic acid acetic; Described organic acid is selected from oleic acid, and lauric acid is sad, stearic acid, any one in palmitinic acid, and described Organic Alcohol is TriMethylolPropane(TMP), and the mol ratio of described organic acid and Organic Alcohol is 1:3; Described catalyzer is N-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst.
As preferably, the addition of described agent is the 0.25%-0.75% of raw materials quality.
As preferably, described organic acid is oleic acid or stearic acid, and described catalyst loading is 0.5%, and temperature of reaction is 130 DEG C, and the reaction times is 4 hours.
Another object of the present invention is to provide the application of a kind of TriMethylolPropane(TMP) organic acid acetic in extraordinary oil.
Compared with the prior art, beneficial effect of the present invention is embodied in:
1, the present invention is by selecting N-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst synthesizing trimethylol propane organic acid acetic, and have temperature of reaction low, catalyst loading is few, and the reaction times is short, esterification yield high, and the product acid number of production is little.
2, the TriMethylolPropane(TMP) organic acid acetic synthesized by the present invention has biological degradability, has the low and lubricating function of toxicity simultaneously.
3, the present invention replaces partial lubrication agent with TriMethylolPropane(TMP) organic acid acetic in extraordinary oil, can improve the work-ing life of extraordinary oil.
Embodiment
Oleic acid selected by organic acid of the present invention, lauric acid, sad, stearic acid, palmitinic acid etc., Organic Alcohol selects TriMethylolPropane(TMP), catalyst choice N-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, by orthogonalization experimental study Organic Alcohol and organic acid differential responses mol ratio, catalyst loading, reaction times, temperature of reaction are on the impact of degree of esterification, as following table (acid number is lower, and gamma value is higher):
The orthogonalization test of table 1, oleic acid and TriMethylolPropane(TMP)
As shown in Table 1, when Organic Alcohol and organic acid reaction mol ratio are 1:3, catalyst loading is 0.75%, temperature of reaction 130 DEG C, and react 3 hours at ambient pressure, acid number is 0.8mgKOH/g, and gamma value is the highest; When Organic Alcohol and organic acid reaction mol ratio are 1:3, catalyst loading is 0.50%, and temperature of reaction is 130 DEG C, and react 4 hours at ambient pressure, acid number is 1.2mgKOH/g, and gamma value takes second place; When Organic Alcohol and organic acid reaction mol ratio are 1:3, catalyst loading is 0.750%, and temperature of reaction is 110 DEG C, and react 5 hours at ambient pressure, acid number is 2.6mgKOH/g; Considered by overall economic efficiency, finally we select Organic Alcohol and organic acid reaction mol ratio to be 1:3, and catalyst loading is 0.50%--0.75%, and temperature of reaction is 130 DEG C, reacts 3-4 hour under normal pressure.
According to the orthogonal experiments of oleic acid and TriMethylolPropane(TMP), that we utilize again is sad, stearic acid, lauric acid and palmitinic acid react, and result is as following table:
The reaction of table 2, sad and TriMethylolPropane(TMP)
The reaction of table 3, lauric acid and TriMethylolPropane(TMP)
The reaction of table 4, stearic acid and TriMethylolPropane(TMP)
The reaction of table 5, palmitinic acid and TriMethylolPropane(TMP)
By table 1-5, can find out: under equal conditions, stearic acid and trihydroxymethylpropanyl ester degree the highest, but five kinds of organic acids can carry out esterification with TriMethylolPropane(TMP).
Embodiment 1
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 2.45gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 110 DEG C, reacts 3 hours, obtain the finished product, acid number is 11.2mgKOH/g.
Embodiment 2
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 2.45gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 120 DEG C, reacts 4 hours, obtain the finished product, acid number is 10.9mgKOH/g.
Embodiment 3
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 2.45gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 130 DEG C, reacts 5 hours, obtain the finished product, acid number is 6.0mgKOH/g.
Embodiment 4
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 4.9gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 120 DEG C, reacts 3 hours, obtain the finished product, acid number is 9.2mgKOH/g.
Embodiment 5
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 4.9gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 130 DEG C, reacts 4 hours, obtain the finished product, acid number is 1.2mgKOH/g.
Embodiment 6
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 4.9gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 110 DEG C, reacts 5 hours, obtain the finished product, acid number is 6.2mgKOH/g.。
Embodiment 7
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 7.35gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 130 DEG C, reacts 3 hours, obtain the finished product, acid number is 0.8mgKOH/g.
Embodiment 8
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 7.35gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 120 DEG C, reacts 4 hours, obtain the finished product, acid number is 3.1mgKOH/g.。
Embodiment 9
Take 134g TriMethylolPropane(TMP) and 846g oleic acid adds in Florence flask, after stirring, add 7.35gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 110 DEG C, reacts 5 hours, obtain the finished product, acid number is 2.6mgKOH/g.。
Embodiment 10
Take 134g TriMethylolPropane(TMP) and 432g is sad adds in Florence flask, add 2.83gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst after stirring, stir, heating, control temperature is 130 DEG C, reacts 4 hours, obtain the finished product, acid number is 2.2mgKOH/g.
Embodiment 11
Take 134g TriMethylolPropane(TMP) and 600g lauric acid adds in Florence flask, after stirring, add 3.67gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 130 DEG C, reacts 4 hours, obtain the finished product, acid number is 2.3mgKOH/g.
Embodiment 12
Take 134g TriMethylolPropane(TMP) and 582g stearic acid adds in Florence flask, after stirring, add 4.93gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 130 DEG C, reacts 4 hours, obtain the finished product, acid number is 1.3mgKOH/g.
Embodiment 13
Take 134g TriMethylolPropane(TMP) and 768g palmitinic acid adds in Florence flask, after stirring, add 4.51gN-alkyl pyrrolidone group methyl acid phosphate ionic-liquid catalyst, stir, heating, control temperature is 130 DEG C, reacts 4 hours, obtain the finished product, acid number is 2.3mgKOH/g.
Embodiment 14
Taking 3g Yatall MA adds in beaker, add the diethanolamine of 6g, the super acid amides of 3g and 5g TriMethylolPropane(TMP) organic acid acetic again, heat while stirring, be warming up to 50 degree, after stirring, add 15g petroleum sodium sulfonate, 5g boric acid ester, 1g sorbitan mono-oleic acid ester S-80,40g 22# spindle oil, stir, finally add 22g water while stirring, finally obtain the cutting fluid of yellow transparent, gained cutting fluid PB value is 650N, 5% cast iron filing/filter paper method rust-preventing characteristic 0 grade, 5%pH value 9.2.
Embodiment 15
Taking 2g Yatall MA adds in beaker, add the diethanolamine of 6g, the super acid amides of 8g and 4g TriMethylolPropane(TMP) organic acid acetic again, heat while stirring, be warming up to 50 degree, 12g heavy benzol base petroleum sodium sulfonate, 2g ethylene glycol monobutyl ether, 2g boric acid ester, 1g sorbitan mono-oleic acid ester S-80,20g 22# spindle oil is added after stirring, stir, finally add 43g water while stirring, finally obtain the cutting fluid of yellow transparent, gained cutting fluid PB value is 646N, 5% cast iron filing/filter paper method rust-preventing characteristic 0 grade, 5%pH value 9.5.
Claims (4)
1. the synthetic method of TriMethylolPropane(TMP) organic acid acetic, is characterized in that, with organic acid and Organic Alcohol for raw material, and add proper catalyst, synthesis under normal pressure 3-5 hour under 110 DEG C of-130 DEG C of conditions, obtains TriMethylolPropane(TMP) organic acid acetic; Described organic acid is selected from oleic acid, and lauric acid is sad, stearic acid, any one in palmitinic acid, and described Organic Alcohol is TriMethylolPropane(TMP), and the mol ratio of described organic acid and Organic Alcohol is 1:3; Described catalyzer is N-alkyl pyrrolidone group methyl-phosphorous acid ionic-liquid catalyst.
2. the synthetic method of TriMethylolPropane(TMP) organic acid acetic according to claim 1, is characterized in that, the addition of described agent is the 0.25%-0.75% of raw materials quality.
3. the synthetic method of TriMethylolPropane(TMP) organic acid acetic according to claim 2, is characterized in that, described organic acid is oleic acid or stearic acid, and described catalyst loading is 0.5%, and temperature of reaction is 130 DEG C, and the reaction times is 4 hours.
4. the application of TriMethylolPropane(TMP) organic acid acetic in extraordinary oil in claim 1-3 described in any one.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037146A (en) * | 2015-06-30 | 2015-11-11 | 百川化工(如皋)有限公司 | Di-trimethylolpropane laurate and preparation method thereof |
| CN105218364A (en) * | 2015-10-27 | 2016-01-06 | 诺泰生物科技(合肥)有限公司 | A kind of synthetic method of isopropyl fatty acid ester and the application in extraordinary oil thereof |
| CN105481692A (en) * | 2015-11-30 | 2016-04-13 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
| CN105669449A (en) * | 2016-02-29 | 2016-06-15 | 诺泰生物科技(合肥)有限公司 | Chlorine hydroxyl ester synthesis method and application of chlorine hydroxyl ester in special oil |
| CN106106485A (en) * | 2016-06-22 | 2016-11-16 | 赵思璐 | A kind of compositions preventing and treating spider and preparation method thereof |
| CN109401814A (en) * | 2018-12-26 | 2019-03-01 | 诺泰生物科技(合肥)有限公司 | P t butylbenzoic acid alkanolamide class corrosion inhibitor and its synthetic method and the application in extraordinary oil |
| CN109652213A (en) * | 2019-01-18 | 2019-04-19 | 重庆大学 | A kind of esters insulating oil and preparation method thereof |
| CN115403472A (en) * | 2022-08-31 | 2022-11-29 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037146A (en) * | 2015-06-30 | 2015-11-11 | 百川化工(如皋)有限公司 | Di-trimethylolpropane laurate and preparation method thereof |
| CN105218364A (en) * | 2015-10-27 | 2016-01-06 | 诺泰生物科技(合肥)有限公司 | A kind of synthetic method of isopropyl fatty acid ester and the application in extraordinary oil thereof |
| CN105481692A (en) * | 2015-11-30 | 2016-04-13 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
| CN105481692B (en) * | 2015-11-30 | 2017-05-10 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
| CN105669449A (en) * | 2016-02-29 | 2016-06-15 | 诺泰生物科技(合肥)有限公司 | Chlorine hydroxyl ester synthesis method and application of chlorine hydroxyl ester in special oil |
| CN105669449B (en) * | 2016-02-29 | 2018-04-06 | 诺泰生物科技(合肥)有限公司 | A kind of synthetic method of chlorine hydroxyl ester and its application in extraordinary oil |
| CN106106485A (en) * | 2016-06-22 | 2016-11-16 | 赵思璐 | A kind of compositions preventing and treating spider and preparation method thereof |
| CN109401814A (en) * | 2018-12-26 | 2019-03-01 | 诺泰生物科技(合肥)有限公司 | P t butylbenzoic acid alkanolamide class corrosion inhibitor and its synthetic method and the application in extraordinary oil |
| CN109652213A (en) * | 2019-01-18 | 2019-04-19 | 重庆大学 | A kind of esters insulating oil and preparation method thereof |
| CN115403472A (en) * | 2022-08-31 | 2022-11-29 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
| CN115403472B (en) * | 2022-08-31 | 2024-04-05 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
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