- Efficient and regioselective ring-opening of epoxides with carboxylic acid catalyzed by graphite oxide
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An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleo-phile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.
- Mirza-Aghayan, Maryam,Tavana, Mahdieh Molaee,Niazi, Elaheh Golam Alipour,Boukherroub, Rabah
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p. 532 - 538
(2020/07/17)
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- Production method for tributyrin
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The invention provides a production method for tributyrin. The method comprises the following steps: the tributyrin with a high content is produced by taking butyric acid and glycerol as raw materialsand excessive butyric acid as a water carrying agent, wherein the molar ratio of the butyric acid to the glycerol is (4-6):1. The method also comprises performing staged reactive distillation on thereaction mixture, and further comprises washing or filtering the reaction product and recycling the excessive butyric acid. According to the invention, the yield of the tributyrin produced by adoptingthe method is up to 95%, the purity is up to 90% or more, the process operation is simple and convenient, the cost is low, and no other toxic or unsafe raw materials or solvents are introduced.
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Paragraph 0015-0017
(2018/03/28)
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- Method for synthesizing butyrin
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The invention provides a method for synthesizing butyrin. According to the method, butyric acid, glycerinum, a catalyst and a solid dehydrating agent are subjected to an esterification reaction under the heating condition, after the reaction is finished, filtration is conducted, a sodium hydroxide solution is dropwise added to the filtrate until the filtrate is neutral, then still standing and layering are conducted, the supernatant oil phase is taken to pass through an anhydrous sodium sulfate dry column, and the butyrin product is obtained. According to the method, it is avoided that an organic solvent serves as a water-carrying agent, the evaporation cost is decreased, the potential production safety hazard is reduced, pollution to the environment is avoided, and the synthesis technology is environmentally friendlier and safer; meanwhile, it is avoided that the organic solvent possibly remains in the product to cause potential safety hazard when the product is applied to feed-products; in addition, the esterification reaction is more efficient by the addition of the solid dehydrating agent, the reaction time is shortened and the reaction conversion ratio is increased.
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Paragraph 0017-0019
(2017/09/08)
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- Method for preparing single glycerlol of the butyric acid
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The invention discloses a preparation method for glyceryl tributyrate. The preparation method comprises: taking glycerin and n-butyric acid as raw materials, adding a catalyst and heating to 100-110 DEG C with stirring, performing heating reflux as well as dropwise adding butyric anhydride, stopping reaction until no water is generated in the reaction solution during dropwise adding, cooling to room temperature, and filtering, so as to obtain glyceryl tributyrate. The catalyst is a mixture of sulfonic-acid mesoporous molecular sieve and ZSM-5 acidic zeolite, and the usage amount of the catalyst is 2-10% by weight of the sum of glycerin and n-butyric acid. By taking sulfonic-acid mesoporous molecular sieve and ZSM-5 acidic zeolite as the catalyst, the selectivity is high, the reaction time is shortened, the generation of by-products is reduced and the catalyst is reusable. By employing the method, the reaction system does not need a water-carrying agent, so that the reaction cost and safe hidden trouble are reduced, the purification step of the product is simplified, the post-processing process is simple, environment is protected and energy is saved. The obtained glyceryl tributyrate is high in purity and high in yield, the reaction speed is fast, and industrial production is easy to realize.
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Paragraph 0015; 0018; 0019; 0022
(2019/01/28)
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- A method for preparing butyrin
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The invention provides a method for preparing tributyrin. The method comprises the following steps: reacting glycerinum with butyryl chloride by taking organic alkali as a acid-binding agent, thereby obtaining a mixture containing tributyrin, wherein the mole ratio of the three materials, namely, glycerinum, butyryl chloride and organic alkali, is 1:(3-3.3):3.3. The method further comprises the following steps: extracting a mixture containing tributyrin by using water, collecting an organic phase, and performing reduction vaporization to remove a solvent in the organic phase, thereby obtaining tributyrin. In the method, the mole ratio of butyryl chloride to glycerinum is kept at (3-3.3):1 during reaction, and massive over amount is not needed. In addition, after the reaction is completed, residual trace butyryl chloride can be hydrated into butyric acid and hydrochloric acid in the following water washing process and can be carried away by a water phase together with residual glycerinum, thus a purpose that butyryl chloride is separated from a target object is achieved.
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Paragraph 0025-0026
(2017/03/17)
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- Biobased catalyst in biorefinery processes: Sulphonated hydrothermal carbon for glycerol esterification
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Sulphonated hydrothermal carbon (SHTC), obtained from d-glucose by mild hydrothermal carbonisation and subsequent sulphonation with sulphuric acid, is able to catalyse the esterification of glycerol with different carboxylic acids, namely, acetic, butyric and caprylic acids. Product selectivity can be tuned by simply controlling the reaction conditions. On the one hand, SHTC provides one of the best selectivity towards monoacetins described up to now without the need for an excess of glycerol. On the other hand, excellent selectivity towards triacylglycerides (TAG) can be obtained, beyond those described with other solid catalysts, including well-known sulphonic resins. Recovery of the catalyst showed partial deactivation of the solid. The formation of sulphonate esters on the surface, confirmed by solid state NMR, was the cause of this behaviour. Acid treatment of the used catalyst, with subsequent hydrolysis of the surface sulphonate esters, allows SHTC to recover its activity. The higher selectivity towards mono- and triesters and its renewable origin makes SHTC an attractive catalyst in biorefinery processes.
- De La Calle, Carlos,Fraile, José M.,García-Bordejé, Enrique,Pires, Elísabet,Roldán, Laura
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p. 2897 - 2903
(2015/05/13)
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- Agonists for Antimicrobial Peptide Systems
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Short chain fatty acids (SCFAs) and glycerol esters of SCFAs not previously used for that purpose are provided for use as a medicament for treating, preventing or counteracting microbial infections in animals, including humans, by stimulating the innate antimicrobial peptide defense system. Preferred compounds include phenyl substituted short chain fatty acids (SCFAs) derivatives and. Also provided are methods and compositions for treating, preventing or counteracting microbial infections, including bacterial, viral, fungal, and parasitic infections, by administration of medicaments comprising a secretagogue-effective amount of the compounds of the invention.
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- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
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The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0-6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2-Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
- Lie Ken Jie, Marcel S.F.,Lam
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p. 155 - 171
(2007/10/03)
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- Novel Anticancer Prodrugs of Butyric Acid. 2
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The antitumor activity of novel prodrugs butyric acid was examined.The in vitro effect of the compounds on induction of cytodifferentiation and on inhibition of proliferation and clonogenicity showed that (pivaloyloxy)methyl butyrate (1a) (labeled AN-9) was the most active agent.SAR's suggested that its activity stemmed from hydrolytically released butyric acid.In vivo, 1a displayed antitumor activity in B16FO melanoma primary cancer model, manifested by a significant increase in the life span of the treated animals.Murine lung tumor burden, induced by injection of the highly metastatic melanoma cells (B16F10.9), was decreased by 1a.It also displayed a significant therapeutic activity against spontaneous metastases which were induced by 3LL Lewis lung carcinoma cells.Moreover, 1a has the advantage of low toxicity, with an acute LD50 = 1.36 +/- 0.1 g/kg (n = 5).These results suggest that 1a is a potential antineoplastic agent.
- Nudelman, Abraham,Ruse, Margaretta,Aviram, Adina,Rabizadeh, Ester,Shaklai, Matityahu,et al.
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p. 687 - 694
(2007/10/02)
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- Preparation of Carboxylate Esters of Polyhydric Alcohols by Using a Sulfonated Charcoal Catalyst
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Ethane-1,2-diol, propane-1,2-diol, butane-1,4-diol and propane-1,2,3-triol are readily esterified by carboxylic acids in near quantitative yields in the presence of a sulfonated charcoal catalyst.
- Prager, Rolf H.,Yurui, Zhang
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p. 1003 - 1005
(2007/10/02)
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