CN101284822A - Preparation method of dihydric alcohol epoxidized fatty acid - Google Patents
Preparation method of dihydric alcohol epoxidized fatty acid Download PDFInfo
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- CN101284822A CN101284822A CNA2008100711830A CN200810071183A CN101284822A CN 101284822 A CN101284822 A CN 101284822A CN A2008100711830 A CNA2008100711830 A CN A2008100711830A CN 200810071183 A CN200810071183 A CN 200810071183A CN 101284822 A CN101284822 A CN 101284822A
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- fatty acid
- dihydric alcohol
- epoxidized fatty
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Abstract
The invention relates to a method for synthesizing dihydric alcohol epoxy fatty acid and is characterized in that: AlCl3 ionic liquid is used as catalyst, 100 weight portions of epoxy fatty acid methyl ester, 15 to 50 weight portions of dihydric alcohol and 1 to 10 weight portions of ionic liquid catalyst are mixed according to the proportion, N2 is aerated, the mixture is stirred to increase the temperature to between 140 and 150 DEG C; a reaction under constant temperature is performed until no liquid is evaporated, the heating is stopped, and the catalyst is removed to obtain dihydric alcohol epoxy fatty acid. In the synthetic process, ion liquid is used as the catalyst to react, has good catalytic activity, is easy to separate from the product after the reaction, can be repeatedly used, and have low corrosiveness and good industrial application prospect. The dihydric alcohol epoxy fatty acid synthesized by the method improves extraction resistant and volatility resistant performances of epoxy fatty acid plasticizer in PVC products, and has good market popularization prospect.
Description
Technical field
The present invention relates to a kind of field of plastics additives, be specifically related to a kind of method of utilizing ionic-liquid catalyst catalytic preparation dihydric alcohol epoxidized fatty acid.
Background technology
Phthalate is the softening agent that purposes is the widest, consumption is maximum, but adjacent benzoic acid ester plasticizer product is volatile in the course of processing, has exudative and transport property with behind the PVC finished product, and heavy dose enters human body carinogenicity constantly.Seek adjacent benzoic ether class substitute nontoxic, environmental protection and become extremely urgent task.Plant oil based softening agent is to utilize crude vegetal, by functional group reactions glyceryl ester is carried out structural transformation, to improve the consistency of crude vegetal and PVC.The achievement in research of this respect mainly is the epoxidation grease at present.The epoxidized fatty acid methyl esters is owing to exist epoxide group, anti-extraction performance and the volatility resistance fatty acid methyl ester that compares is good, but its anti-extraction performance and volatility resistance can be compared with DOP and differ too many, therefore the epoxidized fatty acid methyl esters softening agent of releasing in the market can only substitute DOP on a small quantity, and can only be applied to the lower plasticized PVC goods of class, also can't apply in enormous quantities.
Ionic liquid is as a kind of novel environmentally friendly solvent and liquid acid alkaline catalysts, has the advantage that other organic and inorganic solvents and traditional catalyst do not possess, carry out transesterification reaction with ionic liquid as catalyzer, catalytic activity is good, separate with product easily after the reaction, reusable, corrodibility is low.Foundation is catalyzer with the ionic liquid, the epoxidized fatty acid methyl esters obtains dihydric alcohol epoxidized fatty acid with diol reaction, can effectively increase the molecular weight of epoxidized fatty acid softening agent, improve anti-extraction, the volatility resistance energy of epoxidized fatty acid softening agent in the PVC goods.
Summary of the invention
The object of the present invention is to provide a kind of method of utilizing ionic-liquid catalyst catalytic preparation dihydric alcohol epoxidized fatty acid, utilize the dihydric alcohol epoxidized fatty acid of this method preparation, can improve anti-extraction, the volatility resistance energy of epoxidized fatty acid softening agent in the PVC goods greatly.
For realizing that the technical scheme that purpose of the present invention adopts is:
(1) epoxy aliphatic acid methyl ester, dibasic alcohol and ionic-liquid catalyst weight part proportioning are as follows:
Epoxy aliphatic acid methyl ester 100
Dibasic alcohol 15～50
Ionic-liquid catalyst 1～10
(2) epoxidized fatty acid methyl esters, dibasic alcohol and ionic-liquid catalyst are mixed in proportion, feed N
2, to stir and be warming up to 140～150 ℃, isothermal reaction stops heating to there not being liquid to steam, and removes catalyzer, obtains dihydric alcohol epoxidized fatty acid.
In present method epoxy aliphatic acid methyl ester can be synthetic by following grease: one or more mixture of rapeseed oil, Oleum Gossypii semen, soybean oil, Oleum Cocois, leprosy fruit oil, sunflower seed oil, lard or fish oil or their recovery waste oil.
Dibasic alcohol in present method is ethylene glycol, propylene glycol, butyleneglycol, pentanediol, hexylene glycol, glycol ether, triglycol, polyoxyethylene glycol or polypropylene glycol.
Used ionic-liquid catalyst is AlCl in present method
3The type ionic liquid is made of aluminum chloride and nitrogen-containing organic compound, and this nitrogen-containing organic compound is alkyl quaternary ammonium salts, alkyl quaternary phosphonium salt, alkyl substituted pyridines salt, alkyl substituted imidazole salt.
Advantage of the present invention is:
(1) carry out transesterification reaction with ionic liquid as catalyzer, catalytic activity is good, separates with product easily after the reaction, and reusable, corrodibility is low, meets the requirement of green chemical industry, has the favorable industrial application prospect.
(2) this technology has improved anti-extraction, the volatility resistance energy of epoxidized fatty acid softening agent in the PVC goods.
Embodiment
In order to make the professional and technical personnel better understand the present invention, following is illustrated in conjunction with specific embodiments, but embodiment is not as the restriction of right of the present invention.
Embodiment 1
1-butyl-3-Methylimidazole the chloroaluminate ionic liquid catalysts that in reactor, adds 100g epoxy aliphatic acid methyl ester, 20g ethylene glycol, 3g, stirring is warming up to 145 ℃, and isothermal reaction stops heating to there not being liquid to steam, remove catalyzer, obtain epoxyfatty acid second binary alcohol esters.
Embodiment 2
The positively charged ion that adds 100g epoxy aliphatic acid methyl ester, 25g ethylene glycol, 1g in reactor is [Ph
3PMe]
+Chlorine aluminic acid alkyl quaternary phosphonium ionic liquid catalyzer, stir and to be warming up to 142 ℃, isothermal reaction stops heating to there not being liquid to steam, and removes catalyzer, obtains epoxyfatty acid second binary alcohol esters.
Embodiment 3
The 1-ethylpyridine chloroaluminate ionic liquid catalysts that in reactor, adds 100g epoxy aliphatic acid methyl ester, 30g propylene glycol, 10g, stirring is warming up to 148 ℃, and isothermal reaction stops heating to there not being liquid to steam, remove catalyzer, obtain epoxyfatty acid third binary alcohol esters.
Embodiment 4
The positively charged ion that adds 100g epoxy aliphatic acid methyl ester, 35g propylene glycol, 7g in reactor is [(CH
3)
3NH]
+Chlorine aluminic acid alkyl quaternary ammonium salts ionic-liquid catalyst, stir and to be warming up to 145 ℃, isothermal reaction stops heating to there not being liquid to steam, and removes catalyzer, obtains epoxyfatty acid third binary alcohol esters.
Claims (5)
1, a kind of preparation dihydric alcohol epoxidized fatty acid synthetic method is characterized in that using AlCl
3The type ionic liquid is a catalyzer, by weight 100 parts epoxidized fatty acid methyl esters, 15～50 parts dibasic alcohol and 1～10 part ionic-liquid catalyst is mixed, and feeds N
2, to stir and be warming up to 140～150 ℃, catalyzer is removed in distillation, obtains dihydric alcohol epoxidized fatty acid.
2, preparation dihydric alcohol epoxidized fatty acid synthetic method according to claim 1 is characterized in that described dibasic alcohol is ethylene glycol, propylene glycol, butyleneglycol, pentanediol, hexylene glycol, glycol ether, triglycol, polyoxyethylene glycol or polypropylene glycol.
3, preparation dihydric alcohol epoxidized fatty acid synthetic method according to claim 1 is characterized in that described catalyzer is AlCl
3The type ionic liquid is made of aluminum chloride and nitrogen-containing organic compound.
4, preparation dihydric alcohol epoxidized fatty acid synthetic method according to claim 3 is characterized in that described nitrogen-containing organic compound is alkyl quaternary ammonium salts, alkyl quaternary phosphonium salt, alkyl substituted pyridines salt, alkyl substituted imidazole salt.
5, preparation method according to claim 1 is characterized in that described epoxy aliphatic acid methyl ester is synthetic by following grease: one or more mixture of rapeseed oil, Oleum Gossypii semen, soybean oil, Oleum Cocois, leprosy fruit oil, sunflower seed oil, lard or fish oil or their recovery waste oil.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CNA2008100711830A CN101284822A (en) | 2008-06-06 | 2008-06-06 | Preparation method of dihydric alcohol epoxidized fatty acid |
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|---|---|---|---|
| CNA2008100711830A CN101284822A (en) | 2008-06-06 | 2008-06-06 | Preparation method of dihydric alcohol epoxidized fatty acid |
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| CN101284822A true CN101284822A (en) | 2008-10-15 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101823966A (en) * | 2010-05-25 | 2010-09-08 | 江南大学 | Method for synthesizing cyclohexane 1, 2-dibutyl carboxylic acid by using ionic liquid catalysis |
| CN102993133A (en) * | 2013-01-08 | 2013-03-27 | 南京工业大学 | Method for preparing epoxy fatty acid methyl ester by one-step method through microreactor |
| CN103224837A (en) * | 2013-04-24 | 2013-07-31 | 华南理工大学 | Rapid and green preparation method of epoxidation soybean oil |
| CN105219479A (en) * | 2015-10-09 | 2016-01-06 | 常州市长润石油有限公司 | A kind of immobilized ionic liquid-catalyzed epoxy methyl esters prepares the method for Green Lubricants |
| JP2016512496A (en) * | 2012-12-13 | 2016-04-28 | サイテク・インダストリーズ・インコーポレーテツド | Asymmetric phosphonium haloaluminate ionic liquid composition |
| CN107011963A (en) * | 2017-03-30 | 2017-08-04 | 四川森迪科技发展股份有限公司 | A kind of method that idesia polycarpa oil prepares lube base oil |
| CN114989489A (en) * | 2021-07-28 | 2022-09-02 | 深圳飞扬兴业科技有限公司 | Epoxy plasticizer and preparation method and application thereof |
-
2008
- 2008-06-06 CN CNA2008100711830A patent/CN101284822A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101823966A (en) * | 2010-05-25 | 2010-09-08 | 江南大学 | Method for synthesizing cyclohexane 1, 2-dibutyl carboxylic acid by using ionic liquid catalysis |
| JP2016512496A (en) * | 2012-12-13 | 2016-04-28 | サイテク・インダストリーズ・インコーポレーテツド | Asymmetric phosphonium haloaluminate ionic liquid composition |
| CN102993133A (en) * | 2013-01-08 | 2013-03-27 | 南京工业大学 | Method for preparing epoxy fatty acid methyl ester by one-step method through microreactor |
| CN102993133B (en) * | 2013-01-08 | 2015-09-02 | 南京工业大学 | Method for preparing epoxy fatty acid methyl ester by one-step method through microreactor |
| CN103224837A (en) * | 2013-04-24 | 2013-07-31 | 华南理工大学 | Rapid and green preparation method of epoxidation soybean oil |
| CN105219479A (en) * | 2015-10-09 | 2016-01-06 | 常州市长润石油有限公司 | A kind of immobilized ionic liquid-catalyzed epoxy methyl esters prepares the method for Green Lubricants |
| CN105219479B (en) * | 2015-10-09 | 2018-04-10 | 常州市长润石油有限公司 | A kind of method that immobilized ionic liquid-catalyzed epoxy methyl esters prepares Green Lubricants |
| CN107011963A (en) * | 2017-03-30 | 2017-08-04 | 四川森迪科技发展股份有限公司 | A kind of method that idesia polycarpa oil prepares lube base oil |
| CN114989489A (en) * | 2021-07-28 | 2022-09-02 | 深圳飞扬兴业科技有限公司 | Epoxy plasticizer and preparation method and application thereof |
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Open date: 20081015 |