Enzymatic preparation of monoglycerides in microemulsion

Holmberg, Krister; Österberg, E.

doi:10.1007/bf02898325

Cited by 133 publications

(56 citation statements)

References 17 publications

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“…he addressed During the last decade, enzymatic synthesis of MG by various lipase catalysts has received a lot of attention due to lower energy requirements and selectivity of the catalyst (7)(8)(9)(10). Although enzyrnatic synthesis of MG offers perhaps the greatest potential for future production of MG, cursent industrial processes are based on the physicochemical glycerolysis of fats and oils.…”

Section: *To Whom Correspondence S H O~~l Dmentioning

confidence: 99%

Glycerolysis of fats and methyl esters

Noureddini

Medikonduru

1997

J Americ Oil Chem Soc

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The glycerolysis of methyl esters and triglycerides with crude glycerol, a coproduct from the transesterification of triglycerides, was studied. Three procedures were followed for this conversion. The first procedure was a one‐step glycerolysis with methyl esters. The second procedure was a two‐step process. This procedure involved an initial partial glycerolysis with methyl esters, followed by fat glycerolysis. The third procedure was a simultaneous glycerolysis with methyl esters and triglycerides. In the glycerolysis with methyl esters, the removal of methanol is vital to the production of mono‐ and diglycerides. Methanol was removed either by drawing vacuum on the reactor or by stripping methanol out by means of an inert carrier gas (nitrogen). Different molar ratios of methyl esters to glycerol were tested in the first two processes. At low concentration of methyl esters, total conversion of methyl esters to mono‐ and diglycerides was achieved. As the concentration of methyl esters was increased, the conversion of methyl esters to mono‐ and diglycerides was decreased. Furthermore, the ratio of mono‐ to diglycerides was also higher at lower concentrations of methyl esters. The conversion of triglycerides in the two‐step process with crude glycerol was similar to a one‐step fat glycerolysis with pure glycerol. The composition of different components and the ratio of mono‐ to diglycerides were also comparable.

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Section: *To Whom Correspondence S H O~~l Dmentioning

confidence: 99%

Glycerolysis of fats and methyl esters

Noureddini

Medikonduru

1997

J Americ Oil Chem Soc

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“…Highly stable lipases in organic solvent offers the possibility of employing various approaches to the enzyme catalyzed synthesis, such as selective hydrolysis or alcoholysis using 1,3-regiospecific lipases [22], esterification of glycerol with fatty acids [23] and glycerolysis of fats or oils [24]. When the production of a high degree pure monoglyceride is desired, lipase-catalyzed esterification is the appropriate route.…”

Section: Enzymatic Glycerolysis and Liquid Catalyzationmentioning

confidence: 99%

“…In the next step the diglyceride undergoes the same process and 2-monoglyceride is produced. Both hydrolysis [22] and alcoholysis [35,36] have been described for preparation of 2-monoglycerides.…”

Section: Alcoholysismentioning

confidence: 99%

Progress in Synthesis of Monoglycerides for Use in Food and Pharmaceuticals

et al. 2017

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Glycerides are lipid esters of the glycerol molecule and fatty acids. Their primary function is the storage of energy. Due to its structure and properties, glycerol participates in the formulation or synthesis of many compounds such as food products, cosmetics, pharmaceuticals, liquid detergents. Monoglycerides (MGs) can be formed by both industrial chemical glycerolysis and biological or enzymatic processes. Chemical glycerolysis bring issues of low MGs yield, high operating temperature, formation of undesirable by-products and high energy consumption. On the other hand enzymatic processes have advantages of mild reaction conditions and high purity of MGs. But, several purification steps are required to obtain food or pharmaceutical grade MG, such as neutralization of the reaction media and discoloration followed by expensive molecular distillation. The purpose of this article is to review the main challenges in the synthesis of MGs from triglycerides (TGs) contained in the various fixed oils and application thereof in the food and pharmaceuticals.

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“…20 A reação de alcoólise pode ser realizada na presença de solventes apolares, reduzindo a velocidade de migração do grupo acila. Por esta razão, a alcoólise de triacilgliceróis fornece rendimentos mais elevados (75-97%) que a hidrólise.…”

Section: Método 1: Hidrólise Ou Alcoólise De Triglicerídeosunclassified

“…Na prática, usualmente as reações promovem a migração do grupo acila de tal forma que se estabelece um equilíbrio da concentração dos produtos formados na razão de 9:1 (1(3) MAG e 2-MAG). 20 Como a glicerólise de triglicerídeos apresenta baixo rendimento, 30-50% em monoglicerídeos, devido ao equilíbrio desfavorável da reação, diversas estratégias são adotadas para deslocar o equilíbrio no sentido desejável da reação, entre as quais são destacadas: presença ou ausência de solventes orgânicos, sistemas em estado sólido e micelas reversas. 26,28 Problemas envolvendo a hidro-filicidade do substrato glicerol em solventes orgânicos e problemas analíticos para a determinação quantitativa dos glicerídeos parciais foram descritos por Ferreira Dias e Fonseca.…”

Section: Método 2: Glicerólise De Triglicerídeosunclassified

Monoglicerídeos: produção por via enzimática e algumas aplicações

Freitas¹,

Bueno²,

Pérez³

et al. 2008

Quím. Nova

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Recebido em 27/3/07; aceito em 26/10/07; publicado na web em 13/8/08 MONOGLYCERIDES: PRODUCTION BY ENZYMATIC ROUTE AND APPLICATIONS: Monoglycerides (MAG) are non-ionic surfactants, widely used in the pharmaceutical, food and cosmetic industries. Although MAGs are manufactured on an industrial scale by chemical glycerolysis of oils and fats, new developments in lipase catalyzed synthesis have been studied as an alternative to the classical method seeking to use clean technology and green chemistry. In this work, different methods such as glycerolysis, selective hydrolysis of fats and oils, and esterification of fatty acids or transesterification of esters with glycerol are presented. The properties and applications of the monoglycerides are also included in this review.Keywords: monoglycerides; lipase; glycerolysis. INTRODUÇÃOMonoglicerídeos são surfatantes não iônicos, que possuem o status GRAS (Generally Recognized as Safe) pela FDA (Food and Drugs Administration-USA), sendo amplamente utilizados nas indústrias farmacêuticas, de alimentos e de cosméticos, 1 por não apresentarem efeitos colaterais quando ingeridos ou irritações na pele, ao contrário dos tensoativos iônicos.2 São basicamente monoésteres formados por ácidos graxos e glicerol, dependendo da orientação das moléculas duas formas isoméricas podem existir, conforme apresentado na Figura 1. Na indústria farmacêutica, os monoglicerídeos (MAG) são utilizados como emolientes para emplastos, liberando lentamente a medicação. Na indústria alimentícia são mais comumente utilizados como emulsificantes em uma ampla gama de produtos como margarinas, derivados do leite, doces e molhos, enquanto que na indústria de cosméticos, são empregados como agentes texturizantes e para melhorar a consistência de cremes e loções.3 Na Tabela 1 são sumarizados diferentes tipos de monoglicerídeos e algumas de suas principais aplicações.A produção mundial de monoglicerídeos é estimada em cerca de 180 mil t por ano, 13 das quais aproximadamente 85 mil são consumidas nos EUA, correspondendo a 70% do total de emulsificantes usados em produtos alimentícios. 14 Normalmente, os MAG são sintetizados quimicamente via gliceró-lise de triglicerídeos empregando catalisadores inorgânicos (Ca (OH) 2 , NaOH) a 220-250 °C.15 A utilização de temperaturas elevadas, além de acarretar um alto consumo energético, é responsável pela parcial degradação dos produtos, com formação de subprodutos escuros e sabor de queimado. 16 Desta forma, quando esta rota é usada, se obtém um produto constituído por uma mistura que contém cerca de 35-60% de monoglicerídeos, 35-50% de diglicerídeos, 1-20% de triglicerídeos, 1-10% de ácidos graxos livres, e o sal de metal alcalino resultante.Tanto fatores técnicos como regulatórios da FDA e da União Européia, entre outras, têm incentivado o desenvolvimento de processos menos poluentes para a síntese de emulsificantes, especialmente para aqueles usados em aplicações farmacêuticas ou relacionados à área de alimentos. 17Recentemente a síntese de MAG catalisada por lipases t...

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Enzymatic preparation of monoglycerides in microemulsion

Cited by 133 publications

References 17 publications

Glycerolysis of fats and methyl esters

Glycerolysis of fats and methyl esters

Progress in Synthesis of Monoglycerides for Use in Food and Pharmaceuticals

Monoglicerídeos: produção por via enzimática e algumas aplicações

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