CN101445452A - Method for synthesizing trimethylolpropane oleic acid dimer acid ester - Google Patents
Method for synthesizing trimethylolpropane oleic acid dimer acid ester Download PDFInfo
- Publication number
- CN101445452A CN101445452A CNA2008101642452A CN200810164245A CN101445452A CN 101445452 A CN101445452 A CN 101445452A CN A2008101642452 A CNA2008101642452 A CN A2008101642452A CN 200810164245 A CN200810164245 A CN 200810164245A CN 101445452 A CN101445452 A CN 101445452A
- Authority
- CN
- China
- Prior art keywords
- oleic acid
- trimethylolpropane
- dimer acid
- acid ester
- hydroxymethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000002253 acid Substances 0.000 title claims abstract description 30
- 150000002148 esters Chemical class 0.000 title claims abstract description 19
- FMNZBNCPTJEVDS-KVVVOXFISA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;(z)-octadec-9-enoic acid Chemical class CCC(CO)(CO)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FMNZBNCPTJEVDS-KVVVOXFISA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 17
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 16
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000005642 Oleic acid Substances 0.000 claims abstract description 16
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 16
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000010189 synthetic method Methods 0.000 claims abstract description 11
- 230000018044 dehydration Effects 0.000 claims abstract description 9
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000011949 solid catalyst Substances 0.000 claims abstract description 8
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 229910052681 coesite Inorganic materials 0.000 claims abstract description 3
- 229910052906 cristobalite Inorganic materials 0.000 claims abstract description 3
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052682 stishovite Inorganic materials 0.000 claims abstract description 3
- 229910052905 tridymite Inorganic materials 0.000 claims abstract description 3
- 239000001294 propane Substances 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 abstract description 8
- 238000005516 engineering process Methods 0.000 abstract description 7
- 239000000539 dimer Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- -1 ester compounds Chemical class 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract 2
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 5
- 230000006837 decompression Effects 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 210000000582 semen Anatomy 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000269319 Squalius cephalus Species 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A synthetic method of trimethylolpropane oleic acid dimer acid ester belongs to the synthetic technology of ester compounds in organic chemistry, takes trimethylolpropane, oleic acid and dimer acid as raw materials, and is characterized in that after dehydration condensation reaction is carried out under the action of a solid catalyst, trimethylolpropane oleic acid dimer acid ester is prepared by filtration; the weight ratio of the trimethylolpropane to the oleic acid to the dimer acid can be 1: 0.1-6.0; the solid catalyst may be Fe2O3－ZrO2－SiO2Or stannous oxide or stannous oxalate and the like, wherein the addition amount of the stannous oxide or stannous oxalate is 0.02-1.0% of the total weight of the trimethylolpropane and the dimer acid and the oleic acid. Through test comparison, the solid catalyst is reasonably selected, and the addition amount and the proportion of the trimethylolpropane, the oleic acid and the dimer acid are reasonably adjusted, and the dehydration condensation reaction temperature and time are optimally selected, so that the process is advanced and reasonable, and the reaction conditions in the production process are mild.
Description
Technical field
The present invention relates to a kind of synthetic method of three-hydroxymethyl-propane oleic acid dimer acid ester, belong to the synthetic technology of ester compound in the organic chemistry.
Background technology
Fast development along with mechanical industry, lubricating oil is also constantly proposed new demand, the synthetic method of existing tricarboxymethyl propane oleate mainly is to make under the effect of Catalyzed by p-Toluenesulfonic Acid agent with TriMethylolPropane(TMP) and oleic acid, and its viscosity is all lower, can not meet the demands.
Dimeracid is with siccative oil or semi-drying wet goods vegetables oil, as Semen Maydis oil, Oleum Gossypii semen, soybean wet goods be raw material through saponification acidifying or direct hydrolysis refining after lipid acid isolates linolic acid again, polymerization makes under the effect of catalyzer.There are abundant soybean oil, Oleum Gossypii semen, Rice pollard oil, Semen Maydis oil and rapeseed oil in China, and the source of dimeracid is out of question.Chinese patent 200710191146.9 provides a kind of dimer acid polyester polyhydric alcohols and preparation method thereof, this series products is used in the polyurethane foam, the catalyzer that adopts is difficult to dispose, may not influence for polyurethane foam, but the quality for high-quality lubricating oil has very big influence, and its technology is cumbersome repeatedly.
Summary of the invention
It is reasonable to the purpose of this invention is to provide a kind of technology, simple to operate, has the synthetic method of the three-hydroxymethyl-propane oleic acid dimer acid ester of better use properties.
The present invention is the synthetic method of three-hydroxymethyl-propane oleic acid dimer acid ester, with TriMethylolPropane(TMP), and oleic acid, dimeracid is a raw material, it is characterized in that after carrying out dehydration condensation under the effect of solid catalyst, filters and makes three-hydroxymethyl-propane oleic acid dimer acid ester.
Described TriMethylolPropane(TMP) and oleic acid, the weight ratio of dimeracid can be 1:0.1～6.0:0.1～6.0.
Described solid catalyst can be Fe2O3-ZrO2-SiO2 or tin protoxide or stannous oxalate etc., and its add-on is TriMethylolPropane(TMP) and dimeracid, 0.02～1.0% of oleic acid gross weight.
The reaction times of described dehydration condensation can be 6～10 hours.
The temperature of reaction of described dehydration condensation can be 160～220 ℃.
The present invention compared with prior art has following outstanding advantage and positively effect:
1, relatively through test, rationally select solid catalyst for use, and pass through the reasonable adjustment of TriMethylolPropane(TMP), oleic acid, dimeracid raw material add-on and proportioning, the optimized choice of dehydration condensation temperature and time, make technology of the present invention more become rationally advanced, its production process reaction conditions gentleness, aftertreatment technology and institute's employing equipment are simple, thereby facility investment and energy consumption are more saved.
2, the viscosity of the three-hydroxymethyl-propane oleic acid dimer acid ester that makes by the present invention, can adjust according to the add-on of dimeracid, thereby satisfy the lubricating oil of various viscosity grades, other character does not change, have characteristics such as high thermal resistance is good, lubricity is good, glue the warm nature excellence, low-temperature fluidity is good, use in the fields such as thick oil, metallic high temperature treated oil, gear oil, aviation kerosene that are applicable to, play and reduce the system friction coefficient, increase oil film strength and the effect that improves the oil product lubricity.Use as the novel lubricating oil product, can improve the production level of lubricating oil.
Embodiment
Embodiment 1: add 50 parts of TriMethylolPropane(TMP)s by weight in reactor, 20 parts of dimeracids, 280 parts of oleic acid, stir and add 3.5 parts of Catalyzed by Stannous Oxide agent down, open stirring after the temperature increasing for melting materials, decompression, pressure is-0.098MPa, heat up gradually, under the reaction conditions of 170 ℃ of temperature the insulation 10 hours, after be cooled to 80 ℃, after filtration three-hydroxymethyl-propane oleic acid dimer acid ester, acid number≤3.0mgKOH/g, viscosity is 70mm2/s.
Embodiment 2: add 50 parts of TriMethylolPropane(TMP)s by weight in reactor, 100 parts of dimeracids, 200 parts of oleic acid, stir and add 3.0 parts of stannous oxalate catalyzer down, open stirring after the temperature increasing for melting materials, decompression, pressure is-0.098MPa, heat up gradually, under the reaction conditions of 210 ℃ of temperature the insulation 10 hours, after be cooled to 80 ℃, filter three-hydroxymethyl-propane oleic acid dimer acid ester, acid number≤3.0mgKOH/g, viscosity is 180mm2/s.
Embodiment 3: add 50 parts of TriMethylolPropane(TMP)s by weight in reactor, 250 parts of dimeracids, 50 parts of oleic acid, stir and add 3.5 parts of stannous oxalate catalyzer down, open stirring after the temperature increasing for melting materials, decompression, pressure is-0.098MPa, heat up gradually, under the reaction conditions of 230 ℃ of temperature the insulation 6 hours, after be cooled to 80 ℃, filter three-hydroxymethyl-propane oleic acid dimer acid ester, acid number≤3.0mgKOH/g, viscosity is 300mm2/s.
Embodiment 4: add 50 parts of TriMethylolPropane(TMP)s by weight in reactor, 200 parts of dimeracids, 50 parts of oleic acid, stir 3.0 parts of Catalyzed by Stannous Oxide agent of adding down, open stirring after the temperature increasing for melting materials, decompression, pressure is-0.098MPa, heat up gradually, insulation is 10 hours under the reaction conditions of 170 ℃ of temperature, after be cooled to 80 ℃, filter three-hydroxymethyl-propane oleic acid dimer acid ester, the transformation efficiency of acid is 98%, acid number≤3.0mgKOH/g, and viscosity is 160mm2/s.
Claims (5)
1, a kind of synthetic method of three-hydroxymethyl-propane oleic acid dimer acid ester, with TriMethylolPropane(TMP), oleic acid, dimeracid is a raw material, it is characterized in that after carrying out dehydration condensation under the effect of solid catalyst, filters and makes three-hydroxymethyl-propane oleic acid dimer acid ester.
2, by the synthetic method of the described three-hydroxymethyl-propane oleic acid dimer acid ester of claim 1, it is characterized in that described TriMethylolPropane(TMP) and oleic acid, the weight ratio of dimeracid is 1:0.1～6.0:0.1～6.0.
3, press the synthetic method of the described three-hydroxymethyl-propane oleic acid dimer acid ester of claim 1, it is characterized in that described solid catalyst is Fe2O3-ZrO2-SiO2 or tin protoxide or stannous oxalate etc., its add-on is TriMethylolPropane(TMP) and dimeracid, 0.02～1.0% of oleic acid gross weight.
4, by the synthetic method of the described three-hydroxymethyl-propane oleic acid dimer acid ester of claim 1, the reaction times that it is characterized in that described dehydration condensation is 6～10 hours.
5, by the synthetic method of the described three-hydroxymethyl-propane oleic acid dimer acid ester of claim 1, the temperature of reaction that it is characterized in that described dehydration condensation is 160～220 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101642452A CN101445452A (en) | 2008-12-30 | 2008-12-30 | Method for synthesizing trimethylolpropane oleic acid dimer acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101642452A CN101445452A (en) | 2008-12-30 | 2008-12-30 | Method for synthesizing trimethylolpropane oleic acid dimer acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101445452A true CN101445452A (en) | 2009-06-03 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008101642452A Pending CN101445452A (en) | 2008-12-30 | 2008-12-30 | Method for synthesizing trimethylolpropane oleic acid dimer acid ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101445452A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106975475A (en) * | 2017-04-26 | 2017-07-25 | 中国石油化工股份有限公司 | It is a kind of for catalyst of synthesizing trimethylol propane ester and preparation method thereof and application |
| CN111205442A (en) * | 2020-02-28 | 2020-05-29 | 上海壹萨化学科技有限公司 | Preparation method of clean type metal working fluid modified ricinoleate additive |
-
2008
- 2008-12-30 CN CNA2008101642452A patent/CN101445452A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106975475A (en) * | 2017-04-26 | 2017-07-25 | 中国石油化工股份有限公司 | It is a kind of for catalyst of synthesizing trimethylol propane ester and preparation method thereof and application |
| CN106975475B (en) * | 2017-04-26 | 2019-12-20 | 中国石油化工股份有限公司 | Catalyst for synthesizing trimethylolpropane ester and preparation method and application thereof |
| CN111205442A (en) * | 2020-02-28 | 2020-05-29 | 上海壹萨化学科技有限公司 | Preparation method of clean type metal working fluid modified ricinoleate additive |
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Application publication date: 20090603 |