Preparation and Properties of the n-Alkyl Acrylates

Rehberg, C. E.; Fisher, C. H.

doi:10.1021/ja01235a040

Cited by 156 publications

(58 citation statements)

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“…An example is the production of PET (polyethylene terephthalate), which involves a step where dimethylterephthalate is transesterified with ethylene glycol in the presence of zinc acetate as catalyst (Scheme 2) 2 . Furthermore, a large number of acrylic acid derivatives is produced by transesterification of methyl acrylate with different alcohols, in the presence of acid catalysts [3][4][5][6] .…”

Section: General Aspects Of Transesterificationmentioning

confidence: 99%

Transesterification of vegetable oils: a review

Schuchardt¹,

Sercheli²,

Vargas³

1998

J. Braz. Chem. Soc.

976

539

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A transesterificação de óleos vegetais com metanol, bem como as principais aplicações de ésteres metílicos de ácidos graxos, são revisadas. São descritos os aspectos gerais desse processo e a aplicabilidade de diferentes tipos de catalisadores (ácidos, hidróxidos, alcóxidos e carbonatos de metais alcalinos, enzimas e bases não-iônicas, como aminas, amidinas, guanidinas e triamino(imino)fosforanos). Enfoque especial é dado às guanidinas, que podem ser facilmente heterogeneizadas em polímeros orgânicos. No entanto, as bases ancoradas lixiviam dos polímeros. Novas estratégias para a obtenção de guanidinas heterogeneizadas mais resistentes à lixiviação são propostas. Finalmente, são descritas várias aplicações para ésteres de ácidos graxos, obtidos por transesterificação de óleos vegetais.The transesterification of vegetable oils with methanol as well as the main uses of the fatty acid methyl esters are reviewed. The general aspects of this process and the applicability of different types of catalysts (acids, alkaline metal hydroxides, alkoxides and carbonates, enzymes and non-ionic bases, such as amines, amidines, guanidines and triamino(imino)phosphoranes) are described. Special attention is given to guanidines, which can be easily heterogenized on organic polymers. However, the anchored catalysts show leaching problems. New strategies to obtain non-leaching guanidine-containing catalysts are proposed. Finally, several applications of fatty acid esters, obtained by transesterification of vegetable oils, are described.

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Section: General Aspects Of Transesterificationmentioning

confidence: 99%

Transesterification of vegetable oils: a review

Schuchardt¹,

Sercheli²,

Vargas³

1998

J. Braz. Chem. Soc.

976

539

View full text Add to dashboard Cite

show abstract

“…Transesterification (Scheme 2), reactions producing esters by catalytical alcoholysis of other esters, also play an important role in the industry, for instance in the manufacture of glycerol esters in fat chemistry (e.g., biodiesel), the transesterification of dimethyl carbonate to diethyl carbonate, or the production of polyethylene terephthalate from dimethyl terephthalate. For these reactions, the usual catalysts are Brønsted mineral acids (H 3 PO 4 , H 2 SO 4 , HCl) [24][25][26], and organic acids such as MeSO 3 H and p-toluenesulfonic acid (TsOH) [27], alkoxides such as NaOR, KOR, ROMgBr [28][29][30][31][32], Lewis bases such as 4-dimethylaminopyridine (DMAP) [33,34], 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) [35], Lewis acids such as BX 3 [36], or AlCl 3 [37], amphoteric Catalysts 2016, 6, 128 5 of 65 compounds (compounds able to react either as acids or bases) such as Bu 3 SnOR [38][39][40][41], perfluorotin oxides [42], Al(OR) 3 [43,44], titanium oxides chlorides [45][46][47][48] or palladium oxides [49,50]. More recently, diaminocarbenes have been introduced as catalysts as well [51][52][53][54].…”

Section: Acyl Group Transfersmentioning

confidence: 99%

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

et al. 2016

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Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organic chemistry. After reviewing the conceptual underpinnings of catalysis, we discuss the applications of different catalysts according to the mechanism of the reactions that they catalyze, including acyl group transfers, nucleophilic additions and substitutions, and C-C bond forming reactions that employ umpolung by nucleophilic additions to C=O and C=C double bonds. We highlight the utility of a broad range of organocatalysts other than compounds based on proline, the cinchona alkaloids and binaphthyls, which have been abundantly reviewed elsewhere. The focus is on organocatalysts, although a few examples employing metal complexes and enzymes are also included due to their significance. Classical Brønsted acids have evolved into electrophilic hands, the fingers of which are hydrogen donors (like enzymes) or other electrophilic moieties. Classical Lewis base catalysts have evolved into tridimensional, chiral nucleophiles that are N-(e.g., tertiary amines), P-(e.g., tertiary phosphines) and C-nucleophiles (e.g., N-heterocyclic carbenes). Many efficient organocatalysts bear electrophilic and nucleophilic moieties that interact simultaneously or not with both the electrophilic and nucleophilic reactants. A detailed understanding of the reaction mechanisms permits the design of better catalysts. Their construction represents a molecular science in itself, suggesting that sooner or later chemists will not only imitate Nature but be able to catalyze a much wider range of reactions with high chemo-, regio-, stereo-and enantioselectivity. Man-made organocatalysts are much smaller, cheaper and more stable than enzymes.

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“…Many linear polymers with alkyl side chains were synthesized, and their orientational orders were examined [5,[63][64][65][66]. The phase transitions of these polymers strongly depend on the side-chain length.…”

Section: Influence Of Alkyl Side Chain On Phase Transitions and Orienmentioning

confidence: 99%

Design and Synthesis of Side‐Chain Liquid Crystal Polymers

Ujiie

Kato

2014

Handbook of Liquid Crystals

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Various types of side‐chain liquid crystal polymers with ferroelectric, photoactive, thermochromic, hydrogen‐bonded, and ionized properties have been synthesized by many research groups, and their physicochemical properties and orientational behavior have been studied. These studies have established the relationship between the structure and the physicochemical properties. This chapter describes the design and synthesis of a conventional side‐chain liquid crystal polymer in which mesogenic side groups are attached to the polymer chains.

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Preparation and Properties of the n-Alkyl Acrylates

Cited by 156 publications

References 0 publications

Transesterification of vegetable oils: a review

Transesterification of vegetable oils: a review

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Design and Synthesis of Side‐Chain Liquid Crystal Polymers

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