CN102826999A - Method for synthesizing neopentyl glycol oleate - Google Patents
Method for synthesizing neopentyl glycol oleate Download PDFInfo
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- CN102826999A CN102826999A CN2011101590708A CN201110159070A CN102826999A CN 102826999 A CN102826999 A CN 102826999A CN 2011101590708 A CN2011101590708 A CN 2011101590708A CN 201110159070 A CN201110159070 A CN 201110159070A CN 102826999 A CN102826999 A CN 102826999A
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- oleic acid
- acid ester
- neopentyl glycol
- compound method
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Abstract
A method for synthesizing neopentyl glycol oleate belongs to the technical field of synthesis of ester compounds in organic chemistry. The method uses the neopentyl glycol and the oleate as raw materials, and is characterized by performing an esterification reaction under effect of a solid acid catalyst, washing with alkali, washing with water and drying to prepare the neopentyl glycol oleate, wherein a weight ratio of the neopentyl glycol and the oleate is 1 : 5.4 to 6.8; the solid acid catalyst is S2O8-8/TiO2-La2O3 or ZnO/SiO2 and has an adding amount of 1.0 to 5.0 % by weight of the total amount of the neopentyl glycol and the oleate; and toluene is used as a water-carrying agent and has an adding amount of 10 to 30 % by weight of the total amount of the neopentyl glycol and the oleate. According to the invention, the neopentyl glycol oleate is prepard from the esterification reaction under the effect of the solid acid catalyst which does not corrode equipment, and the method and the product are high in selectivity, mild in reaction condition, reusable, easy to regenerate, simple to process after reaction and environmentally friendly.
Description
Technical field
The present invention relates to a kind of compound method of NSC 6366 oleic acid ester, belong to technical field of synthesis of ester compounds in the organic chemistry.
Background technology
The NSC 6366 oleic acid ester has excellent viscosity-temperature characteristics ability, good cold property, high-temperature stability and low volatility, thereby can satisfy higher lubricating requirement, and readily biodegradable, is " green " lubricant of a kind of excellent property.Can be used as the base oil of alternative ore lubricating oil, also can be used for modifying environmental-protection type hydraulicefficiency oil and metal cutting, base oil is used in processing such as wire drawing, and its Application Areas is very extensive.The prior synthesizing method of NSC 6366 oleic acid ester is with H
2SO
4, H
3PO
4Deng the inorganic liquid acid as catalyst, by directly the dewater esterification preparation of NSC 6366 and oleic acid.Inorganic liquid acid corrosive equipment, side reaction is many, and product color is dark; Mainly do Preparation of Catalyst NSC 6366 fatty ester with organic acids such as tosic acid, thionamic acids at present, this can cause the catalyst separating difficulty, and aftertreatment is complicated, and " three wastes " discharging is many.With the synthetic rarely seen report of NSC 6366 oleic acid ester of solid acid catalysis, solid acid catalyst is reusable, is prone to regeneration, and can avoid inorganic liquid acid and drawback that organic acid catalyst caused.
Summary of the invention
The purpose of this invention is to provide a kind of reaction temperature with, simple to operate, process environments is friendly, has the compound method of the NSC 6366 oleic acid ester of better practicality.
The present invention is the compound method of NSC 6366 oleic acid ester, is raw material with NSC 6366 and oleic acid, it is characterized in that with toluene being the band aqua, at solid acid S
2O
2- 8/ TiO
2-La
2O
3Or ZnO/SiO
2Katalysis under carry out esterification, then through alkali cleaning, the washing and drying process make the NSC 6366 oleic acid ester.
Said NSC 6366 and oleic weight ratio are 1: 5.4 ~ 6.8.
Said solid acid catalyst is S
2O
2- 8/ TiO
2-La
2O
3(A) or ZnO/SiO
2(B), its add-on is 1.0 ~ 5.0% of NSC 6366 and an oleic acid total weight percent.
The preparation method of said catalyst A is La
2O
3Be dissolved in 10 ~ 50% Ti (SO
4)
2The aqueous solution, La
2O
3With Ti (SO
4)
2Weight ratio be 1: 4.5, evaporation drying, 350 ℃ ~ 750 ℃ temperature roasting 4h, calcining matter is through (the NH of concentration 1.0 ~ 3.0 mol/ L
4)
2S
2O
8Dipping 3 ~ 8h is behind the filtration drying, through 350 ℃ ~ 650 ℃ temperature roasting 4h.
The preparation method of said catalyst B is the temperature roasting 4h of 350 ℃ ~ 650 ℃ on silica gel for chromatography warp, the Zn (CH of warp 10 ~ 50% again
3COO)
2Aqueous solution dipping 3 ~ 8h is behind the filtration drying, through 350 ℃ ~ 650 ℃ temperature roasting 4h.
Said esterification is the band aqua with toluene, and its consumption is 10 ~ 30% of NSC 6366 and an oleic acid total weight percent.
The alkali that said alkaline cleaning procedure uses is NaHCO
3Saturated solution, its consumption are 10 ~ 50% of NSC 6366 and oleic acid total mass per-cent.
Said drying process is that vacuum hydro-extraction is dry, and temperature is 60 ℃ ~ 100 ℃, and vacuum tightness is ﹣ 0.096 MPa ~ ﹣ 0.090 MPa, and the time of dehydrating is 2 ~ 8h.
The present invention compared with prior art has following outstanding advantage and positively effect:
1, the esterification under the effect of employing solid acid catalysis, selectivity is high, and catalyzer is etching apparatus not, and is reusable, and catalyzer is prone to regeneration, thereby can reduce production costs;
2, the solid acid catalysis esterification belongs to heterogeneous catalytic reaction, and catalyzer very easily separates with product, and aftertreatment is simple, and three waste discharge is few;
3, the product color and luster is good, and readily biodegradable belongs to environmentally friendly lubricant, can be used as the substitute products of mineral lubricating oils, and is of many uses.Oleic acid can be the by product of oil prodution industry, and raw material is cheap and easy to get, and belongs to natural product, and is renewable.
Embodiment
Embodiment 1:
In reaction kettle, add 100 parts of NSC 6366s, 570 parts of oleic acid, 90 parts of toluene stir 27 parts of solid acid catalyst S of adding down as the band aqua
2O
2- 8/ TiO
2-La
2O
3, temperature rise to 80 gradually ~ 130 ℃, reflux dewatering 2 ~ 6h, filtered while hot catalyzer then, and be cooled to 40 ~ 60 ℃, with 110 parts of saturated NaHCO
3Solution washing is once used 120 parts 40 ~ 60 ℃ distillation washings twice again, is 60 ~ 100 ℃ in temperature, and underpressure distillation 1h under vacuum tightness ﹣ 0.095 MPa ~ ﹣ 0.09 MPa removes toluene and water, gets the NSC 6366 oleic acid ester, and yield is 92%.
Embodiment 2:
In reaction kettle, add 100 parts of NSC 6366s, 570 parts of oleic acid, 90 parts of toluene stir 20 parts of solid acid catalyst ZnO/SiO of adding down as the band aqua
2, temperature rise to 80 gradually ~ 130 ℃, reflux dewatering 3 ~ 8h, filtered while hot catalyzer then, and be cooled to 40-60 ℃, with 120 parts of saturated NaHCO
3Solution washing with 130 parts 40-60 ℃ distillation washing twice, is 60 ~ 100 ℃ in temperature more once, and underpressure distillation 1h under vacuum tightness ﹣ 0.095 MPa ~ ﹣ 0.09 MPa removes toluene and water, gets the NSC 6366 oleic acid ester, and yield is 87%.
NSC 6366 and oleic reaction equation are in the above-mentioned enforcement:
Claims (8)
1. the compound method of a NSC 6366 oleic acid ester is a raw material with NSC 6366 and oleic acid, it is characterized in that carrying out esterification under the solid acid catalyst effect, makes the NSC 6366 oleic acid ester through alkali cleaning, washing and drying process then.
2. by the compound method of the described NSC 6366 oleic acid ester of claim 1, it is characterized in that said NSC 6366 and oleic weight ratio are 1: 5.4 ~ 6.8.
3. by the compound method of the described NSC 6366 oleic acid ester of claim 1, it is characterized in that said solid acid catalyst is S
2O
2- 8/ TiO
2-La
2O
3(A) or ZnO/SiO
2(B), its add-on is 1.0 ~ 5.0% of NSC 6366 and an oleic acid total weight percent.
4. by the compound method of the described NSC 6366 oleic acid ester of claim 1, it is characterized in that the preparation method of said catalyst A is La
2O
3Be dissolved in 10 ~ 50% Ti (SO
4)
2The aqueous solution, La
2O
3With Ti (SO
4)
2Weight ratio be 1: 4.5, evaporation drying, 350 ℃ ~ 750 ℃ temperature roasting 4h, calcining matter are the (NH of 1.0 ~ 3.0 mol/ L through concentration
4)
2S
2O
8Dipping 3 ~ 8h, behind the filtration drying, 350 ℃ ~ 650 ℃ temperature roasting 4h.
5. by the compound method of the described NSC 6366 oleic acid ester of claim 1, it is characterized in that the preparation method of said catalyst B is the temperature roasting 4h of silica gel for chromatography through 350 ℃ ~ 650 ℃, the Zn (CH of warp 10 ~ 50% again
3COO)
2Aqueous solution dipping 3 ~ 8 h, behind the filtration drying, 350 ℃ ~ 650 ℃ temperature roasting 4h.
6. by the compound method of the described NSC 6366 oleic acid ester of claim 1, it is characterized in that said esterification is the band aqua with toluene, its consumption is 10 ~ 30% of NSC 6366 and an oleic acid total weight percent.
7. by the compound method of the described NSC 6366 oleic acid ester of claim 1, the alkali that it is characterized in that said alkaline cleaning procedure is NaHCO
3Saturated solution, its consumption are 10 ~ 40% of NSC 6366 and oleic acid gross weight.
8. by the compound method of the described NSC 6366 oleic acid ester of claim 1, it is characterized in that said drying process is that vacuum hydro-extraction is dry, temperature is 60 ℃ ~ 90 ℃, and vacuum tightness is ﹣ 0.095 MPa ~ ﹣ 0.09 MPa, and dewatering time is 2 ~ 8 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110159070.8A CN102826999B (en) | 2011-06-15 | 2011-06-15 | Method for synthesizing neopentyl glycol oleate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110159070.8A CN102826999B (en) | 2011-06-15 | 2011-06-15 | Method for synthesizing neopentyl glycol oleate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102826999A true CN102826999A (en) | 2012-12-19 |
| CN102826999B CN102826999B (en) | 2015-03-11 |
Family
ID=47330342
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110159070.8A Expired - Fee Related CN102826999B (en) | 2011-06-15 | 2011-06-15 | Method for synthesizing neopentyl glycol oleate |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566104A (en) * | 2015-12-25 | 2016-05-11 | 江西西林科股份有限公司 | Preparation method of solid superacid catalyst used for esterification of acid type anti-wear agent |
| CN112898235A (en) * | 2019-11-19 | 2021-06-04 | 南通海珥玛科技股份有限公司 | Epoxy neopentyl glycol oleate and synthesis method and application thereof |
| CN113088363A (en) * | 2021-04-14 | 2021-07-09 | 海南热带海洋学院 | Preparation method of coconut oil fatty acid composite ester |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999699A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Synthesis method of neopentyl glycol cocoate |
| CN102010332A (en) * | 2010-10-19 | 2011-04-13 | 沈阳工业大学 | Method for catalytic production of trimethylolpropane oleate by using solid superacid and application of method |
-
2011
- 2011-06-15 CN CN201110159070.8A patent/CN102826999B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999699A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Synthesis method of neopentyl glycol cocoate |
| CN102010332A (en) * | 2010-10-19 | 2011-04-13 | 沈阳工业大学 | Method for catalytic production of trimethylolpropane oleate by using solid superacid and application of method |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566104A (en) * | 2015-12-25 | 2016-05-11 | 江西西林科股份有限公司 | Preparation method of solid superacid catalyst used for esterification of acid type anti-wear agent |
| CN112898235A (en) * | 2019-11-19 | 2021-06-04 | 南通海珥玛科技股份有限公司 | Epoxy neopentyl glycol oleate and synthesis method and application thereof |
| CN113088363A (en) * | 2021-04-14 | 2021-07-09 | 海南热带海洋学院 | Preparation method of coconut oil fatty acid composite ester |
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| Publication number | Publication date |
|---|---|
| CN102826999B (en) | 2015-03-11 |
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