626-82-4Relevant articles and documents
Synthesis of lutein esters by using a reusable lipase-pluronic conjugate as the catalyst
Hou, Miao,Wang, Rui,Wu, Xiaoling,Zhang, Yifei,Ge, Jun,Liu, Zheng
, p. 1825 - 1829 (2015)
An enzymatic route to synthesize lutein esters was investigated using a lipase-Pluronic conjugate as the catalyst. For the synthesis of lutein palmitate, the enzymatic process gave a conversion of 85 % for lutein and a product purity of 96 % at 50 °C within 12 h, whereas the free lipase catalyzed process achieved a conversion below 10 %. To demonstrate the generality of this enzymatic process, lutein laurate, lutein myristate and lutein stearate were also synthesized achieving conversions of 73.8, 88.5, 84.4 % respectively. Moreover, the lipase-Pluronic conjugate can be reused for batches in the synthesis of lutein esters. As demonstrated by this study, the enzyme-Pluronic conjugate holds great promise for practical applications in industrial biocatalysis. Graphical Abstract An enzymatic approach to synthesize lutein esters was investigated using a lipase-Pluronic conjugate as the catalyst.
Zr-MOF-808 as Catalyst for Amide Esterification
Villoria-del-álamo, Beatriz,Rojas-Buzo, Sergio,García-García, Pilar,Corma, Avelino
supporting information, p. 4588 - 4598 (2020/12/25)
In this work, zirconium-based metal–organic framework Zr-MOF-808-P has been found to be an efficient and versatile catalyst for amide esterification. Comparing with previously reported homogeneous and heterogeneous catalysts, Zr-MOF-808-P can promote the reaction for a wide range of primary, secondary and tertiary amides with n-butanol as nucleophilic agent. Different alcohols have been employed in amide esterification with quantitative yields. Moreover, the catalyst acts as a heterogeneous catalyst and could be reused for at least five consecutive cycles. The amide esterification mechanism has been studied on the Zr-MOF-808 at molecular level by in situ FTIR spectroscopic technique and kinetic study.
MOFs based on 1D structural sub-domains with Br?nsted acid and redox active sites as effective bi-functional catalysts
Díaz, Urbano,Moreno, José María,Velty, Alexandra
, p. 3572 - 3585 (2020/06/25)
A novel family of lamellar MOF-type materials, which contain Br?nsted acid sites together with redox active centers, based on assembled 1D organic-inorganic nanoribbons were obtained through direct solvothermal synthesis routes, using specific monotopic benzylcarboxylate spacers with thiol substituents in thepara-position like structural modulator compounds and effective post-synthesis oxidized treatments to generate accessible sulfonic groups. Low-dimensional aluminum metal-organic materials, containing free sulfonic pendant groups (Al-ITQ-SO3H), were successfully tested in several acid reactions, such as acetalization, esterification and ring opening of epoxides with a significant impact on fine chemistry processes. The direct introduction of stabilized Pd nanoparticles, cohabitating with pendant sulfonic groups, allowed the preparation of active bi-functional MOF-type hybrid materials (Al-ITQ-SO3H/Pd) capable of carrying out one-pot two-step oxidation-acetalization reactions, exhibiting high yield and high activity during consecutive catalytic cycles.
Aldehyde effect and ligand discovery in Ru-catalyzed dehydrogenative cross-coupling of alcohols to esters
Jiang, Xiaolin,Zhang, Jiahui,Zhao, Dongmei,Li, Yuehui
, p. 2797 - 2800 (2019/03/27)
The presence of different aldehydes is found to have a significant influence on the catalytic performance when using PN(H)P type ligands for dehydrogenation of alcohols. Accordingly, hybrid multi-dentate ligands were discovered based on an oxygen-transfer alkylation of PNP ligands by aldehydes. The relevant Ru-PNN(PO) system provided the desired unsymmetrical esters in good yields via acceptorless dehydrogenation of alcohols. Hydrogen bonding interactions between the phosphine oxide moieties and alcohol substrates likely assisted the observed high chemoselectivity.
Development and Validation of a Novel Free Fatty Acid Butyl Ester Gas Chromatography Method for the Determination of Free Fatty Acids in Dairy Products
Mannion, David T.,Furey, Ambrose,Kilcawley, Kieran N.
, p. 499 - 506 (2019/01/08)
Accurate quantification of free fatty acids in dairy products is important for both product quality control and legislative purposes. In this study, a novel fatty acid butyl ester method was developed, where extracted free fatty acids are converted to butyl esters prior to gas chromatography with flame ionization detection. The method was comprehensively validated to establish linearity (20-700 mg/L; R2 > 0.9964), limits of detection (5-8 mg/L), limits of quantification (15-20 mg/L), accuracy (1.6-5.4% relative error), interday precision (4.4-5.3% relative standard deviation), and intraday precision (0.9-5.6% relative standard deviation) for each individual free fatty acid. A total of 17 dairy samples were analyzed, covering diverse sample matrices, fat content, and degrees of lipolysis. The method was compared to direct on-column injection and fatty acid methyl ester methods and overcomes limitations associated with these methods, such as either column-phase absorption or deterioration, accurate quantification of short-chain free fatty acids, and underestimation of polyunsaturated free fatty acid.
Preparation method of long-chain ester
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Paragraph 0094; 0095; 0096; 0097; 0098-0111, (2019/03/23)
The invention relates to the field of organic synthesis and provides a preparation method of long-chain ester, which comprises the following steps: carrying out esterification reaction of the carboxylic acid and the alcohol through a catalyst and obtaining a long-chain ester phase and a water phase post the standing and layering of the reaction liquid; the catalyst comprises ionic liquid or eutectic solvent; purifying and separating the long-chain ester phase to obtain high-purity long-chain ester; introducing the residual substance again into the esterification reaction system for reaction after the water in the water phase is removed. The yield and the purity of the long-chain ester prepared by the invented method are as high as 99.8% and 99% respectively as indicated by the embodiment of the preparation method.
Three step auto-tandem catalysed hydroesterification: Access to linear fruity esters from piperylene
Neubert, Peter,Steffen, Matthias,Behr, Arno
, p. 122 - 127 (2015/07/15)
A convenient and selective access to saturated hexanoic esters via hydroesterification of piperylene with synthesis gas and methanol is presented. This is the first three step auto-tandem hydroesterification, which is 100% atom economic proceeding under mild conditions. Our optimisations revealed Pd2(dba)3/1,2-dtbpmb as the best catalytic system. Besides, the reaction also tolerates several alcohols, which offers a broad range of fruity esters. In addition, we present insights into the reaction sequence, investigating whether the reaction proceeds via two- or three-step reaction cascade.
Synthesis of carboxylic acid esters in the presence of micro- and mesoporous aluminosilicates
Grigor'Eva,Suleimanova,Agliullin,Kutepov
, p. 773 - 779 (2015/01/30)
The catalytic properties of zeolites HY, HBeta, and HZSM-12 and of mesoporous amorphous aluminosilicate in liquid-phase esterification of aliphatic (monobasic C1-C18, dibasic C6, C10) and aromatic (benzoic, trimellitic, phthalic) carboxylic acids with butanol were studied. Zeolite HBeta appeared to be the most active catalyst. Procedures were developed for preparing esters in the presence of zeolitic catalyst HBeta, ensuring 100% selectivity of ester formation at 90-98% conversion of the acid.
Lipase-catalyzed synthesis of ethyl hexanoate in microemulsion system
Tan, Zhongqin,Han, Xiaoxiang,Hu, Xiaoli,Du, Huan,Bao, Xiuxiu
, p. 9675 - 9678 (2014/01/06)
This paper studied lipase-catalyzed synthesis of ethyl hexanoate in dodecylbenzenesulfonic acid/isooctane/water microemulsion system. The effect of several parameters, such as w0 ([H2O]/[surfactant]) value, reaction time, reaction temperature, oil phase solvent, buffer solution pH value of microemulsion system on the esterification have been investigated. The results showed that the best experimental conditions for catalytic synthesis ethyl hexanoate were as follows: w0 = 4, reaction time 4 h, reaction temperature 40 °C, buffer solution pH 7. Under these conditions, the conversion of ethyl hexanoate can reach 98.5 %. Lipase-catalyzed synthesis of ethyl hexanoate in dodecylbenzenesulfonic acid inverse microemulsion system has triple mechanism, namely acid catalyzes, microemulsion catalyzes and enzyme catalyzes.
Rape seedling lipase catalyzed synthesis of flavor esters through transesterification in hexane
Liaquat, Muhammad,Khan, Saeed,Aslam, Sher,Khan, Ayub,Khan, Hakim,Khan, Shah Masaud,Ali, Sardar,Wahab, Said,Bhatti, Haq Nawaz
scheme or table, p. 144 - 150 (2012/05/19)
Butyl butyrate, a short-chain ester with fruity pineapple odor, is a significant flavor compound that is widely used in the food industry. Enzymatic synthesis of butyl butyrate by crude rape seedlings lipase has been investigated in n-hexane using 50 g/L of enzyme at 40 °C through alcoholysis of ethyl butyrate with butanol. The influence of reaction parameters such aswater content, water activity, substrate concentrations and reaction time were also studied. Ester yield of 60% after 96 h has been obtained with 0.5% (v/v) of added water using reversible reaction or activated ester. A concentration of 0.1M of butanol while 0.6 M of ethyl butyrate was found optimal for butyl butyrate synthesis. The esterification catalyzed by lipase was inhibited by increasing the butanol concentration beyond 0.10 M while no inhibition of enzyme was observed with ethyl butyrate. (Z)-3-hexen-1-ol (cis-3-hexen-1-ol) esters posses the odour of freshly cut grass and are used to obtain natural green top notes in food flavours. Two different approaches for rapeseed lipase catalyzed synthesis of these flavour esters were also studied. Acylation of (Z)-3-hexen-1-ol with vinyl acetate (irreversible acyl donor) and butyl caproate (reversible acyl donor) was evaluated. Ester yield of 99 % after 24 h was obtained for (Z)-3-hexen-1-yl acetate with vinyl acetate as acyl donor. Crude rape seedlings lipase has proved to be an efficient catalyst to obtain (Z)-3-hexen-1-ol esters using irreversible acyl donor such as vinyl ester in hexane. Crude lipase also works well at ambient temperature without need of immobilization.
