CN103864725A - Eleostearic acid glycidyl ester and preparation method thereof - Google Patents
Eleostearic acid glycidyl ester and preparation method thereof Download PDFInfo
- Publication number
- CN103864725A CN103864725A CN201410121315.1A CN201410121315A CN103864725A CN 103864725 A CN103864725 A CN 103864725A CN 201410121315 A CN201410121315 A CN 201410121315A CN 103864725 A CN103864725 A CN 103864725A
- Authority
- CN
- China
- Prior art keywords
- eleostearic acid
- glycidyl ester
- acid potassium
- acid glycidyl
- reaction
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention discloses eleostearic acid glycidyl ester. Eleostearic acid potassium reacts with epoxy chloropropane to prepare tung oil derivatives. The preparation method specifically comprises the steps of performing reaction in a KOH methanol aqueous solution by using tung oil as a raw material to prepare eleostearic acid potassium; after removing methanol and water from eleostearic acid potassium, using absolute ethanol to dissolve with eleostearic acid potassium, and finally reacting with epoxy chloropropane to prepare the eleostearic acid glycidyl ester. The eleostearic acid glycidyl ester disclosed by the invention is a multipurpose chemical intermediate; the preparation method of the eleostearic acid glycidyl ester is low in production cost, simple and convenient in operation, short in production cycle, low in environment pollution, good in product quality and easy in realization of industrial production; moreover, the eleostearic acid glycidyl ester can be used for preparing a variety of paints and can be used as a diluent, a modifier, a surfactant and the like of a variety of paints, and has good market application prospects.
Description
Technical field
The present invention relates to chemical intermediate grease technical field, relate in particular to a kind of eleostearic acid glycidyl ester and preparation method thereof.
background technology
Tung oil is best siccative oil in vegetables oil in the world, there is the good characteristics such as fast drying, strong adhesion, rich gloss, heat-resisting, cold-resistant, waterproof, anticorrosion, acid and alkali-resistance, non-conductive, radioprotective, can be used as protective system, easer, insulating varnish etc.In recent years along with the continuous expansion of market to high grade paint demands such as natural environmental-protective coating, anticorrosion, antirust, insulation, tung oil, as preparing one of natural matter of high grade paint, becomes the object that people competitively study day by day.Therefore, how to prepare eleostearic acid glycidyl ester and become those skilled in the art's major issue urgently to be resolved hurrily.
Summary of the invention
Technical problem solved by the invention is to provide a kind of eleostearic acid glycidyl ester and preparation method thereof, to solve the shortcoming in above-mentioned background technology.
Technical problem solved by the invention realizes by the following technical solutions:
A kind of eleostearic acid glycidyl ester, it makes tung oil derivative by eleostearic acid potassium and epichlorohydrin reaction, and structural formula is:
Eleostearic acid glycidyl ester preparation method, taking tung oil as raw material, in KOH methanol aqueous solution, reaction makes eleostearic acid potassium; After the methyl alcohol and water removed in eleostearic acid potassium, use dehydrated alcohol and eleostearic acid potassium to dissolve, last and epichlorohydrin reaction makes eleostearic acid glycidyl ester; Its reaction formula is:
Concrete steps are as follows:
(1) eleostearic acid potassium preparation
In reaction vessel, add tung oil, KOH and methanol aqueous solution to obtain mixed solution, wherein, the consumption (quality) of KOH is 20%～25% of tung oil quality, and the concentration of methanol aqueous solution is 70%～90%, and methanol aqueous solution adds 3～8 times for tung oil quality (g) number of volume (mL) number; Residual reaction liquid will be obtained after Distillation recovery part methyl alcohol after mixed solution heating reflux reaction, residual reaction liquid filters to get filtrate after using activated decoloration, after filtrate is cooling, eleostearic acid potassium crystallization eleostearic acid potassium crystal, finally obtains eleostearic acid potassium by eleostearic acid potassium crystal decompress filter, vacuum-drying;
(2) eleostearic acid glycidyl ester preparation
The eleostearic acid potassium, the dehydrated alcohol that in reaction vessel, add step (1) to prepare obtain lysate, and volume (mL) number that adds of dehydrated alcohol is 3～6 times that eleostearic acid potassium quality (g) is counted; Stir also slow heating for dissolving liquid to reflux state, after dissolving in lysate, eleostearic acid potassium add again epoxy chloropropane to obtain intermediate liquid, then the ethanol in reclaim under reduced pressure intermediate liquid and excessive epoxy chloropropane must generate liquid, finally adopt water washing to generate the organic layer of liquid, after organic layer vacuum hydro-extraction, obtain eleostearic acid glycidyl ester.
In the present invention, in described step (1), the mixed solution heating reflux reaction time is 1 h～3 h.
In the present invention, in described step (1), the yield of methyl alcohol is 50%～80% of methanol aqueous solution add-on.
In the present invention, in described step (1), eleostearic acid potassium crystal is dry 3 h～5 h under 45 DEG C～55 DEG C vacuum conditions.
In the present invention, in described step (2), the mole dosage of epoxy chloropropane is 2～5 times of eleostearic acid potassium mole dosage.
In the present invention, in described step (2), lysate reflux time is 4 h～6 h.
Beneficial effect: the present invention is multiduty chemical intermediate, its preparation method production cost is low, easy and simple to handle, with short production cycle, environmental pollution is little, good product quality, easily realizes suitability for industrialized production; And can be used for preparing multiple coating and as the thinner of multiple coating and properties-correcting agent, tensio-active agent etc., market application foreground is good.
Embodiment
Describe the present invention below by following specific embodiment.
Case study on implementation 1
A kind of eleostearic acid glycidyl ester, it makes by eleostearic acid potassium and epichlorohydrin reaction, and concrete steps are as follows:
(1) eleostearic acid potassium preparation
In the there-necked flask of 500 mL, add the KOH of 40 g tung oil, 8.8 g and the methanol aqueous solution of 160 mL 75% to obtain mixed solution, by mixed solution heating reflux reaction 2 h, reclaim 80 mL methyl alcohol and obtain residual reaction liquid, and filter to get filtrate after obtaining residual reaction liquid employing activated decoloration, after filtrate is cooling, eleostearic acid potassium crystallization eleostearic acid potassium crystal, finally by eleostearic acid potassium crystal decompress filter, and under 50 DEG C of vacuum conditions dry 3 h, obtain eleostearic acid potassium 39.4 g, productive rate is 90.6%.
(2) eleostearic acid glycidyl ester preparation
In the 500 mL there-necked flasks with reflux, add eleostearic acid potassium 40.0 g, 160 mL dehydrated alcohols prepared by step (1) to obtain lysate; Stir also slow heating for dissolving liquid to reflux state, after eleostearic acid potassium dissolves in lysate, add again 53 mL epoxy chloropropane to obtain intermediate liquid, keep back flow reaction 5 h; Then the ethanol in reclaim under reduced pressure intermediate liquid and excessive epoxy chloropropane must generate liquid, finally adopt water washing to generate the organic layer 3 times of liquid, obtain eleostearic acid glycidyl ester 39.4 g, productive rate 93.2% after organic layer vacuum hydro-extraction.
Case study on implementation 2
A kind of eleostearic acid glycidyl ester, it makes by eleostearic acid potassium and epichlorohydrin reaction, and concrete steps are as follows:
(1) eleostearic acid potassium preparation
In the there-necked flask of 500 mL, add the KOH of 40 g tung oil, 8.8 g and the methanol aqueous solution of 160 mL 85% to obtain mixed solution, by mixed solution heating reflux reaction 2 h, reclaim 90 mL methyl alcohol and obtain residual reaction liquid, and filter to get filtrate after obtaining residual reaction liquid employing activated decoloration, after filtrate is cooling, eleostearic acid potassium crystallization eleostearic acid potassium crystal, finally by eleostearic acid potassium crystal decompress filter, and under 50 DEG C of vacuum conditions dry 3 h, obtain eleostearic acid potassium 41.3 g, productive rate is 95.0%.
(2) eleostearic acid glycidyl ester preparation
In the 500 mL there-necked flasks with reflux, add eleostearic acid potassium 40.0 g, 175 mL dehydrated alcohols prepared by step (1) to obtain lysate; Stir also slow heating for dissolving liquid to reflux state, after eleostearic acid potassium dissolves in lysate, add again 43 mL epoxy chloropropane to obtain intermediate liquid, keep back flow reaction 5 h; Then the ethanol in reclaim under reduced pressure intermediate liquid and excessive epoxy chloropropane must generate liquid, finally adopt water washing to generate the organic layer 3 times of liquid, obtain eleostearic acid glycidyl ester 38.9g, productive rate 92% after organic layer vacuum hydro-extraction.
Case study on implementation 3
A kind of eleostearic acid glycidyl ester, it makes by eleostearic acid potassium and epichlorohydrin reaction, and concrete steps are as follows:
(1) eleostearic acid potassium preparation
In the there-necked flask of 500 mL, add the KOH of 40 g tung oil, 8.8 g and the methanol aqueous solution of 160 mL 90% to obtain mixed solution, by mixed solution heating reflux reaction 2 h, reclaim 100 mL methyl alcohol and obtain residual reaction liquid, and filter to get filtrate after obtaining residual reaction liquid employing activated decoloration, after filtrate is cooling, eleostearic acid potassium crystallization eleostearic acid potassium crystal, finally by eleostearic acid potassium crystal decompress filter, and under 50 DEG C of vacuum conditions dry 3 h, obtain eleostearic acid potassium 40.4 g, productive rate is 92.9%.
(2) eleostearic acid glycidyl ester preparation
In the 500 mL there-necked flasks with reflux, add eleostearic acid potassium 40.0 g, 150 mL dehydrated alcohols prepared by step (1) to obtain lysate; Stir also slow heating for dissolving liquid to reflux state, after eleostearic acid potassium dissolves in lysate, add again 53 mL epoxy chloropropane to obtain intermediate liquid, keep back flow reaction 6 h; Then the ethanol in reclaim under reduced pressure intermediate liquid and excessive epoxy chloropropane must generate liquid, finally adopt water washing to generate the organic layer 3 times of liquid, obtain eleostearic acid glycidyl ester 39.1 g, productive rate 92.5% after organic layer vacuum hydro-extraction.
Case study on implementation 4
A kind of eleostearic acid glycidyl ester, it makes by eleostearic acid potassium and epichlorohydrin reaction, and concrete steps are as follows:
(1) eleostearic acid potassium preparation
In the there-necked flask of 500 mL, add the KOH of 40 g tung oil, 8.8 g and the methanol aqueous solution of 160 mL 90% to obtain mixed solution, by mixed solution heating reflux reaction 2 h, reclaim 100 mL methyl alcohol and obtain residual reaction liquid, and filter to get filtrate after obtaining residual reaction liquid employing activated decoloration, after filtrate is cooling, eleostearic acid potassium crystallization eleostearic acid potassium crystal, finally by eleostearic acid potassium crystal decompress filter, and under 50 DEG C of vacuum conditions dry 3 h, obtain eleostearic acid potassium 40.4 g, productive rate is 92.9%.
(2) eleostearic acid glycidyl ester preparation
In the 500 mL there-necked flasks with reflux, add eleostearic acid potassium 40.0 g, 130 mL dehydrated alcohols prepared by step (1) to obtain lysate; Stir also slow heating for dissolving liquid to reflux state, after eleostearic acid potassium dissolves in lysate, add again 53 mL epoxy chloropropane to obtain intermediate liquid, keep back flow reaction 7 h; Then the ethanol in reclaim under reduced pressure intermediate liquid and excessive epoxy chloropropane must generate liquid, finally adopt water washing to generate the organic layer 3 times of liquid, obtain eleostearic acid glycidyl ester 39.2 g, productive rate 92.7% after organic layer vacuum hydro-extraction.
The eleostearic acid glycidyl ester of preparing by above-mentioned preparation method had both retained three conjugated double bonds in tung oil structure, newly add again highly active epoxide group simultaneously, be introduced in coating resin molecular chain, three oxidable polymerizations of conjugated double bond, epoxide group can provide cross-linking reaction point, can make like this coating resin there is better film forming properties, give the performances such as good water-fast, the acid and alkali-resistance of film, high tenacity simultaneously.
More than show and described ultimate principle of the present invention and principal character and advantage of the present invention.The technician of the industry should understand; the present invention is not restricted to the described embodiments; that in above-described embodiment and specification sheets, describes just illustrates principle of the present invention; without departing from the spirit and scope of the present invention; the present invention also has various changes and modifications, and these changes and improvements all fall in the claimed scope of the invention.The claimed scope of the present invention is defined by appending claims and equivalent thereof.
Claims (9)
1. an eleostearic acid glycidyl ester, is characterized in that, makes tung oil derivative by eleostearic acid potassium and epichlorohydrin reaction, and structural formula is:
2. an eleostearic acid glycidyl ester preparation method as claimed in claim 1, is characterized in that, taking tung oil as raw material, in KOH methanol aqueous solution, reaction makes eleostearic acid potassium; After the methyl alcohol and water removed in eleostearic acid potassium, use dehydrated alcohol and eleostearic acid potassium to dissolve, last and epichlorohydrin reaction makes eleostearic acid glycidyl ester; Its reaction formula is:
Concrete steps are as follows:
(1) eleostearic acid potassium preparation
In reaction vessel, add tung oil, KOH and methanol aqueous solution to obtain mixed solution, residual reaction liquid will be obtained after Distillation recovery part methyl alcohol after mixed solution heating reflux reaction, residual reaction liquid filters to get filtrate after using activated decoloration, after filtrate is cooling, eleostearic acid potassium crystallization eleostearic acid potassium crystal, finally obtains eleostearic acid potassium by eleostearic acid potassium crystal decompress filter, vacuum-drying;
(2) eleostearic acid glycidyl ester preparation
The eleostearic acid potassium, the dehydrated alcohol that in reaction vessel, add step (1) to prepare obtain lysate, stir also slow heating for dissolving liquid to reflux state, after dissolving in lysate, eleostearic acid potassium add again epoxy chloropropane to obtain intermediate liquid, then the ethanol in reclaim under reduced pressure intermediate liquid and excessive epoxy chloropropane must generate liquid, finally adopt water washing to generate the organic layer of liquid, after organic layer vacuum hydro-extraction, obtain eleostearic acid glycidyl ester.
3. eleostearic acid glycidyl ester preparation method according to claim 2, it is characterized in that, in described step (1), the quality of KOH is 20%～25% of tung oil quality, the concentration of methanol aqueous solution is 70%～90%, and methanol aqueous solution to add volume number be 3～8 times of tung oil total mass number.
4. eleostearic acid glycidyl ester preparation method according to claim 2, is characterized in that, in described step (1), the mixed solution heating reflux reaction time is 1 h～3 h.
5. eleostearic acid glycidyl ester preparation method according to claim 2, is characterized in that, in described step (1), the yield of methyl alcohol is 50%～80% of methanol aqueous solution add-on.
6. eleostearic acid glycidyl ester preparation method according to claim 2, is characterized in that, in described step (1), eleostearic acid potassium crystal is dry 3 h～5 h under 45 DEG C～55 DEG C vacuum conditions.
7. eleostearic acid glycidyl ester preparation method according to claim 2, is characterized in that, in described step (2), the volume number that adds of dehydrated alcohol is 3～6 times of eleostearic acid potassium total mass number.
8. eleostearic acid glycidyl ester preparation method according to claim 2, is characterized in that, the mole dosage of epoxy chloropropane is 2～5 times of eleostearic acid potassium mole dosage.
9. eleostearic acid glycidyl ester preparation method according to claim 2, is characterized in that, in described step (2), lysate reflux time is 4 h～6 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410121315.1A CN103864725A (en) | 2014-03-28 | 2014-03-28 | Eleostearic acid glycidyl ester and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410121315.1A CN103864725A (en) | 2014-03-28 | 2014-03-28 | Eleostearic acid glycidyl ester and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103864725A true CN103864725A (en) | 2014-06-18 |
Family
ID=50903795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410121315.1A Pending CN103864725A (en) | 2014-03-28 | 2014-03-28 | Eleostearic acid glycidyl ester and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103864725A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749882A (en) * | 2016-12-15 | 2017-05-31 | 吴定财 | A kind of metal adhesive Nian Jie with silicon rubber and preparation method thereof |
| WO2018018444A1 (en) * | 2016-07-27 | 2018-02-01 | Dow Global Technologies Llc | Crosslinkable surfactants |
| CN109504285A (en) * | 2018-10-31 | 2019-03-22 | 中南林业科技大学 | A kind of preparation method of quick-drying tung oil woodenware lacquer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001079190A1 (en) * | 2000-04-17 | 2001-10-25 | Guy Thomas Topping | Method of synthesizing glyceryl mono-esters |
| CN103360246A (en) * | 2013-07-11 | 2013-10-23 | 中南林业科技大学 | Method for preparing eleostearic acid monoglycerides from tung oil |
-
2014
- 2014-03-28 CN CN201410121315.1A patent/CN103864725A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001079190A1 (en) * | 2000-04-17 | 2001-10-25 | Guy Thomas Topping | Method of synthesizing glyceryl mono-esters |
| CN103360246A (en) * | 2013-07-11 | 2013-10-23 | 中南林业科技大学 | Method for preparing eleostearic acid monoglycerides from tung oil |
Non-Patent Citations (2)
| Title |
|---|
| KUN HUANG ET AL.: "Epoxy Monomers Derived from Tung Oil Fatty Acids and Its Regulable Thermosets Cured in Two Synergistic Ways", 《BIOMACROMOLECULES》, vol. 15, 2 February 2014 (2014-02-02), pages 837 - 843 * |
| 麻文杰 等.: "两步法合成桐油酸缩水甘油酯", 《中国油脂》, vol. 39, no. 12, 20 December 2014 (2014-12-20), pages 46 - 48 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018018444A1 (en) * | 2016-07-27 | 2018-02-01 | Dow Global Technologies Llc | Crosslinkable surfactants |
| US11066500B2 (en) | 2016-07-27 | 2021-07-20 | Dow Global Technologies Llc | Crosslinkable surfactants |
| CN106749882A (en) * | 2016-12-15 | 2017-05-31 | 吴定财 | A kind of metal adhesive Nian Jie with silicon rubber and preparation method thereof |
| CN109504285A (en) * | 2018-10-31 | 2019-03-22 | 中南林业科技大学 | A kind of preparation method of quick-drying tung oil woodenware lacquer |
| CN109504285B (en) * | 2018-10-31 | 2020-07-10 | 中南林业科技大学 | Preparation method of quick-drying tung oil wood varnish |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107089914B (en) | Cardanol-based acrylate reactive diluent and preparation method and application thereof | |
| CN104128102B (en) | A kind of cyclo-dextrin-modified compounded organic solvent NF membrane and preparation method thereof | |
| CN102558572B (en) | Method for preparing xylogen acetylated derivative in ionic liquid solvent | |
| CN103864725A (en) | Eleostearic acid glycidyl ester and preparation method thereof | |
| CN109679678B (en) | Eutectic solvent and method for extracting alkaline/non-alkaline nitrogen from simulated gasoline | |
| CN103449979A (en) | Bisphenol epoxy resin and preparation method thereof | |
| CN101775108A (en) | Synthesis of modified aqueous epoxy resin and method for preparing antiseptic rusty paint | |
| CN102633644A (en) | Synthesis process of trifluoroacetyl ethyl acetate | |
| CN106268497A (en) | One class contains abietyl Gemini surface active agent and the performance thereof of polyoxyethylene ether coupling link | |
| CN104262127B (en) | Brush-type two fluorine monomer and synthetic method thereof | |
| CN105924465A (en) | POSS-base high-temperature-resisting room temperature ionic liquid and preparation method thereof | |
| CN103819308A (en) | Solidifiable poly-meta-phenylene as well as preparation method and application thereof | |
| CN101985496B (en) | Method of synthesizing methoxypolyethylene glycol allyl methyl ether of water reducer macromonomer | |
| CN107674030A (en) | A kind of preparation technology of the imidazoline sulfate quaternary ammonium salt corrosion inhibitor based on gutter oil | |
| CN103865055B (en) | A kind of macromole hydrophobic monomer polytetrahydrofuran diacrylate and preparation method thereof | |
| CN103122041A (en) | Novel self-hydrogen-supplying diphenyl ketone macromolecular photoinitiator and preparation method thereof | |
| CN110092734A (en) | A kind of 2-(phenylmethylene) malononitrile or derivatives thereof series connection synthetic method | |
| CN105753821A (en) | Preparation method of 2,5-furandicarboxylic acid | |
| CN101864072B (en) | Synthetizing method of water reducer macromer methoxyl-polyethyleneglycol allylether | |
| CN103980077B (en) | A kind of synthetic polyfluoro of suzuki reaction of catalysis of ligand-free palladium is for the method for para-terpheny derivative | |
| CN104151258A (en) | Method and apparatus for recycling tetrahydrofuran solvent during reduction reaction of L-phenylglycinol | |
| CN103570936A (en) | Synthetic method of concrete water reducing agent macromonomer methoxy polyethylene glycol isopentenyl ether | |
| CN104016859A (en) | 2, 3-butanediol monoether acetate and preparation method thereof | |
| CN105130732A (en) | Preparation method of cyclic di-p-xylyene | |
| CN103819334B (en) | Glycerinum ternary aldehyde and synthesis method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20140618 |