CN101100426A - Method for synthesizing isotridecanol adipate - Google Patents
Method for synthesizing isotridecanol adipate Download PDFInfo
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- CN101100426A CN101100426A CNA2007100701586A CN200710070158A CN101100426A CN 101100426 A CN101100426 A CN 101100426A CN A2007100701586 A CNA2007100701586 A CN A2007100701586A CN 200710070158 A CN200710070158 A CN 200710070158A CN 101100426 A CN101100426 A CN 101100426A
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- isotridecanol
- synthetic method
- hexylene glycol
- dehydration condensation
- adipate
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Abstract
Synthesis of isotridecyl alcohol ester adipate is carried out by taking adipic acid and isotridecyl alcohol as raw materials, dewatering condensation reacting under action of metal oxide catalyst, and filtering to obtain isotridecyl alcohol ester adipate in proportion of adipic acid: isotridecyl alcohol =1:2.1-2.6 mol. Metal oxide is stannous oxide or ferric oxide and magnesium oxide etc.; the addition is total 0.02-0.15%. It costs low and the apparatus is simple, it has stable quality, higher selectivity, rational adjustment and optimizing selection of reactive temperature and time.
Description
Technical field
The present invention relates to a kind of synthetic method of isotridecanol adipate, belong to technical field of synthesis of ester compounds in the organic chemistry.
Background technology
Isotridecanol adipate has good lubricity, high thermal resistance and excellent viscosity-temperature characteristics because of it, and biodegradable performance has broad application prospects in fields such as fibre finishing, aircraft engine lubricating oil, metalworking fluids.At present the synthetic method of adipic acid ester series products mainly is the direct esterification method, is to be raw material with hexanodioic acid and Fatty Alcohol(C12-C14 and C12-C18), under the effect of an acidic catalyst such as tosic acid, tetrabutyl titanate etc., and the esterification of directly dewatering, general used Fatty Alcohol(C12-C14 and C12-C18) is an isooctyl alcohol.Make catalyzer with tosic acid and tetrabutyl titanate, catalyst separating is difficulty, needs operations such as neutralization, washing, and the part catalyst residue easily changes product in product in storage process, influences the stability of product.The then rarely seen report of the synthetic method of hexylene glycol isotridecanol.
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 isotridecanol adipate of better use properties.
The present invention is the synthetic method of hexylene glycol isotridecanol, is raw material with hexanodioic acid and different tridecanol, it is characterized in that carrying out dehydration condensation under metal oxide is the effect of catalyzer, makes isotridecanol adipate after the filtration.
The mass ratio of described hexanodioic acid and different tridecanol can be 1: 2.1～and 2.6.
Described metal oxide can be tin protoxide or ferric oxide, magnesium oxide etc., and its add-on is 0.02～0.15% of hexanodioic acid and a different tridecanol gross weight.
The temperature of reaction of described dehydration condensation can be 170 ℃～250 ℃.
The reaction times of described dehydration condensation can be 4～10 hours.
Described dehydration condensation can carry out under nitrogen atmosphere.
Also can carry out dealcoholation treatment behind the described dehydration condensation, the dealcoholysis temperature is 180～230 ℃, and the dealcoholysis time is 1～2 hour, and dealcoholysis vacuum tightness is≤80Pa.
The present invention compared with prior art has following outstanding advantage and positively effect:
1, rationally select for use metal oxide to make catalyzer, such catalyzer has higher selectivity, generates by product hardly; And metal oxide is etching apparatus not, and production technique is simple, can remove by filtering, and makes constant product quality.
2, by the optimized choice to reasonable adjustment, temperature of reaction and the time of the add-on of hexanodioic acid and different tridecanol and proportioning, make technology of the present invention advanced reasonable, the equipment that is adopted is simple, thereby facility investment is more saved.
3, by synthetic isotridecanol adipate of the present invention, has good lubricity, good low-temperature performance, excellent high-temperature stability, low volatility, biological degradability is good, the additive that can be widely used in senior lubricant, the basic wet goods of processing such as metal cutting, wire drawing.
Embodiment
Embodiment 1: use the 1000ml four-hole boiling flask to make reactor, stirring arm, N are housed
2Ingress pipe, thermometer, prolong add hexanodioic acid 207g (1.40mol), different tridecanol 672g (3.36mol), magnesium oxide 0.440g successively, are warming up to 100 ℃ under stirring, material fusion in the reactor, logical N
2, continue to be warming up to 200 ℃, and under this temperature, react, distillate the water that reaction generates, behind the reaction 6h, anhydrous distillating changes the depickling still over to, is 50Pa in vacuum tightness, 200 ℃ of dealcoholysis 1.5h of temperature, be cooled to 70 ℃ filter isotridecanol adipate 765g.
Embodiment 2: use the 1000ml four-hole boiling flask to make reactor, stirring arm, N are housed
2Ingress pipe, thermometer, prolong add hexanodioic acid 207g (1.40mol), different tridecanol 630g (3.15mol), tin protoxide 0.711g successively, are warming up to 100 ℃ under stirring, material fusion in the reactor, logical N
2, continue to be warming up to 200 ℃, and under this temperature, react, distillate the water that reaction generates, behind the reaction 8h, anhydrous distillating changes the depickling still over to, is 50Pa in vacuum tightness, 210 ℃ of dealcoholysis 1h of temperature, be cooled to 70 ℃ filter isotridecanol adipate 760g.
Claims (7)
1, a kind of synthetic method of hexylene glycol isotridecanol is a raw material with hexanodioic acid and different tridecanol, it is characterized in that carrying out dehydration condensation under metal oxide is the effect of catalyzer, makes isotridecanol adipate after the filtration.
2, by the synthetic method of the described hexylene glycol isotridecanol of claim 1, the mass ratio that it is characterized in that described hexanodioic acid and different tridecanol is 1: 2.1～2.6.
3, by the synthetic method of the described hexylene glycol isotridecanol of claim 1, it is characterized in that described metal oxide is tin protoxide or ferric oxide, magnesium oxide, its add-on is 0.02～0.15% of hexanodioic acid and a different tridecanol gross weight.
4, by the synthetic method of the described hexylene glycol isotridecanol of claim 1, the temperature of reaction that it is characterized in that described dehydration condensation is 170 ℃～250 ℃.
5, by the synthetic method of claim 1 or 4 described hexylene glycol isotridecanols, the reaction times that it is characterized in that described dehydration condensation is 4～10 hours.
6, by the synthetic method of the described hexylene glycol isotridecanol of claim 1, it is characterized in that described dehydration condensation carries out under nitrogen atmosphere.
7, by the synthetic method of the described hexylene glycol isotridecanol of claim 1, it is characterized in that also carrying out dealcoholation treatment behind the described dehydration condensation, the dealcoholysis temperature is 180～230 ℃, and the dealcoholysis time is 1～2 hour, and dealcoholysis vacuum tightness is≤80Pa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100701586A CN101100426A (en) | 2007-07-24 | 2007-07-24 | Method for synthesizing isotridecanol adipate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100701586A CN101100426A (en) | 2007-07-24 | 2007-07-24 | Method for synthesizing isotridecanol adipate |
Publications (1)
| Publication Number | Publication Date |
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| CN101100426A true CN101100426A (en) | 2008-01-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNA2007100701586A Pending CN101100426A (en) | 2007-07-24 | 2007-07-24 | Method for synthesizing isotridecanol adipate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101857672A (en) * | 2010-06-13 | 2010-10-13 | 苏州博纳化学科技有限公司 | Synthetic method of polyether-isotridecanol monoester |
| CN104961924A (en) * | 2015-06-18 | 2015-10-07 | 张家港市大能塑料制品有限公司 | Cold-resistant plasticizer |
| CN109534991A (en) * | 2018-11-02 | 2019-03-29 | 浙江皇马科技股份有限公司 | A kind of preparation method of two isotridecanol of decanedioic acid |
| CN112724016A (en) * | 2020-12-31 | 2021-04-30 | 潍坊加易加生物科技有限公司 | Method for recycling esterification catalyst stannous oxide |
-
2007
- 2007-07-24 CN CNA2007100701586A patent/CN101100426A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101857672A (en) * | 2010-06-13 | 2010-10-13 | 苏州博纳化学科技有限公司 | Synthetic method of polyether-isotridecanol monoester |
| CN101857672B (en) * | 2010-06-13 | 2011-12-28 | 苏州博纳化学科技有限公司 | Synthetic method of polyether-isotridecanol monoester |
| CN104961924A (en) * | 2015-06-18 | 2015-10-07 | 张家港市大能塑料制品有限公司 | Cold-resistant plasticizer |
| CN109534991A (en) * | 2018-11-02 | 2019-03-29 | 浙江皇马科技股份有限公司 | A kind of preparation method of two isotridecanol of decanedioic acid |
| CN109534991B (en) * | 2018-11-02 | 2021-07-23 | 浙江皇马科技股份有限公司 | Preparation method of diisotridecyl sebacate |
| CN112724016A (en) * | 2020-12-31 | 2021-04-30 | 潍坊加易加生物科技有限公司 | Method for recycling esterification catalyst stannous oxide |
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