Name: soap formation from triglycerides
Uploaded: 2020-03-26T07:22:28.000Z
Duration: 4 min 10 s
Channel: JoVE

Óleos vegetais e gorduras animais são lipídios naturais em plantas ou animais. Óleos e gorduras geralmente estão na forma de triglicerídeos, que são formados a partir de uma molécula de glicerol e três ácidos graxos. Um ácido graxo é um ácido carboxílico fraco com uma cadeia de hidrocarbonetos como grupo funcional. No triglicerídeo, os três ácidos graxos estão ligados à molécula de glicerol por ligações éster. Um triglicerídeo, portanto, tem três grupos éster, tornando a molécula um triéster.
Um éster é um tipo de molécula orgânica que é como um ácido carboxílico, com o hidrogênio da hidroxila substituído por um grupo alquil ou arila. Este grupo é rotulado como R-prime para mostrar que pode ser diferente do grupo R do outro lado. Em um triglicerídeo, o R-prime é a espinha dorsal do glicerol e cada grupo R é a cadeia de um ácido graxo.
Os ácidos graxos com ligações duplas em suas cadeias de carbono são conhecidos como ácidos graxos insaturados. Essas ligações duplas tendem a estar na conformação cis, o que coloca uma curva na cadeia. Os triglicerídeos com essas cadeias dobradas não podem se encaixar perfeitamente, então as forças atrativas entre elas são tipicamente de longo alcance e fracas.
Os ácidos graxos com apenas ligações simples entre os átomos de carbono são saturados. Essas cadeias não dobradas permitem que os triglicerídeos se agrupem, permitindo interações intermoleculares mais fortes e de curto alcance. Isso dá aos triglicerídeos saturados um ponto de fusão mais alto do que os triglicerídeos insaturados, que geralmente são líquidos à temperatura ambiente.
Os triglicerídeos podem ser convertidos de volta em ácidos graxos e glicerol pela hidrólise dos três ésteres. A hidrólise de éster é uma reação que quebra uma ligação éster com uma molécula de água ou um íon hidróxido para formar um ácido carboxílico e um álcool. Um uso comum da hidrólise de ésteres é criar sabonetes, que são os sais de ácidos graxos dos triglicerídeos. Esse processo é chamado de saponificação.
Nesta reação, os íons hidróxido atacam cada uma das três carbonilas de éster no triglicerídeo, produzindo três moléculas de ácidos graxos e uma molécula de glicerol. Os carboxilatos de ácidos graxos se associam ao contra-íon da base, que geralmente é sódio ou potássio.
Mas como funciona o sabão? A longa cadeia de carbono é lipofílica e hidrofóbica, o que significa que é atraída por gorduras, mas não por água. O grupo carboxilato é hidrofílico, o que significa que é atraído pela água. Quando você mistura água e sabão, as longas cadeias de carbono tendem a interagir umas com as outras e evitam a interação com as moléculas de água, enquanto os grupos carboxilato preferem interagir com a água. Em última análise, as moléculas de sabão formam aglomerados chamados micelas, com os carboxilatos hidrofílicos voltados para fora.
Agora, vamos supor que haja graxa hidrofóbica em suas mãos. Simplesmente enxaguar as mãos com água não removeria a graxa. Quando você lava com sabão, a graxa interage com as cadeias de carbono do sabão. À medida que as moléculas de sabão formam micelas, elas trazem a graxa para o núcleo hidrofóbico, envolvendo-a em uma casca hidrofílica que pode ser enxaguada com água.
Neste laboratório, você atuará como uma reação de saponificação para criar sabão a partir de óleo de coco e hidróxido de sódio. Em seguida, você testará a tolerância do seu sabão para água dura, comparando a capacidade de formação de espuma em água deionizada, água da torneira e uma solução de cloreto de cálcio, que imita água extremamente dura.

hidrólise de um éster

<h4>Triglicerídeos</h4>
Os triglicerídeos são moléculas de triéster compostas por uma estrutura de glicerol que se liga a 3 ácidos graxos. Estes formam a base de muitos lipídios biológicos encontrados em óleos e gorduras vegetais. Os lipídios isolados do material vegetal são a base dos óleos vegetais, enquanto os lipídios extraídos de animais são usados como banha ou fontes gerais de gorduras.
Uma molécula de ácido graxo tem uma longa cadeia de carbono - entre 12 e 20 carbonos - com um ácido orgânico fraco em uma extremidade. Alguns ácidos graxos têm ligações duplas na cadeia de carbono. Estas são gorduras "insaturadas". Por causa da ligação dupla na cadeia de carbono, esses ácidos graxos normalmente têm uma forma de cadeia dobrada, pois a ligação tende a adotar a conformação cis em vez da conformação trans.
As moléculas de triglicerídeos em um ácido graxo insaturado são incapazes de se empilhar uniformemente, levando a forças menos atrativas entre as moléculas. Assim, as gorduras insaturadas são geralmente líquidas à temperatura ambiente. Em contraste, as gorduras saturadas, ou seja, aquelas com apenas ligações simples em sua cadeia de carbono, são capazes de se empilhar porque sua cadeia tem uma forma mais regular. As gorduras saturadas, portanto, têm forças atrativas mais fortes entre as moléculas e, como resultado, pontos de fusão mais altos. Assim, as gorduras saturadas tendem a ser sólidas à temperatura ambiente.
<h4>Reação de hidrólise</h4>
Os triglicerídeos, como outras moléculas que possuem grupos éster, são capazes de sofrer hidrólise. A hidrólise é um tipo de reação química em que uma molécula de água quebra uma ligação. No caso de uma hidrólise de éster, o nucleófilo - água ou um íon hidróxido - ataca o carbono carbonílico do grupo éster para quebrar a ligação éster. Um fragmento da molécula original ganha o íon hidrogênio da água para formar um álcool, enquanto o outro fragmento ganha o grupo hidróxido para formar um sal do ácido carboxílico.
Em condições normais, apenas algumas reações de hidrólise ocorrem sem a adição de um ácido ou base forte. O ácido ou base forte atua como um catalisador para acelerar a reação e é recuperado no final. A reação de hidrólise é reversível. É chamada de reação de condensação porque produz água como produto secundário.
A hidrólise de um triglicerídeo é um dos exemplos mais antigos de reação de hidrólise, pois tem sido usada há séculos para fazer sabão. A reação é chamada de saponificação.
<h4>saponificação </h4>
Durante a saponificação, os íons hidróxido atacam os grupos carbonila nos três ésteres do triglicerídeo. Portanto, a adição estequiométrica de três moles de hidróxido de sódio a um mol de triglicerídeos resultará na hidrólise dos três grupos ésteres. Essa reação produz três moles de moléculas de sabão e um mol de glicerol. Freqüentemente, a reação será realizada com hidróxido de sódio como reagente limitante para minimizar a quantidade de triglicerídeo não reagido, o que pode reduzir o efeito de secagem do sabão.
Uma molécula de sabão tem uma longa cadeia de carbono hidrofóbica com um ânion carboxilato hidrofílico polar na outra extremidade. A diferença de solubilidade ao longo da molécula permite sua capacidade de limpeza. Na água, as longas cadeias de carbono das moléculas de sabão serão atraídas umas pelas outras e se reorganizarão para evitar as moléculas polares de água. Isso orienta as cabeças polares de carboxilato em direção às moléculas de água, formando uma estrutura esférica conhecida como micela. O centro é hidrofóbico e o exterior é hidrofílico, permitindo que as micelas sejam solúveis em soluções aquosas.
As propriedades micelas do sabão são essenciais para sua capacidade de limpeza. Simplesmente enxaguar a graxa ou o óleo de uma superfície não pode removê-lo. Isso ocorre porque a graxa é hidrofóbica e não é solúvel em água. No entanto, quando o sabão é usado, a graxa entra no interior da micela. O exterior da micela é hidrofílico, por isso pode ser enxaguado com água.
Uma desvantagem significativa do sabão é sua intolerância à água dura. A água dura é uma solução aquosa contendo íons de magnésio, ferro e cálcio na forma de minerais. A "dureza" da água depende da concentração desses íons. Na presença de cátions metálicos, as moléculas de sabão interagem com as moléculas e fazem com que elas caiam da solução, formando um precipitado de sal mais comumente chamado de espuma de sabão.
<h4>Referências</h4>
<ol>
	<li style="font-size:17px">Kotz, J.C., Treichel Jr, P.M., Townsend, J.R. (2012). Química e Reatividade Química. Belmont, CA: Brooks / Cole, Cengage Learning.</li>
	<li style="font-size:17px">Silberg, M.S. (2015). Química: A Natureza Molecular da Matéria e da Mudança. Boston, MA: Colina McGraw.</li>
	<li style="font-size:17px">Streiwiester, A., Heathcock, C.H., Kosower, E.M. (1998). Introdução à Química Orgânica. Rio Saddle Superior, NJ: Prentice Hall.</li>
</ol>

Hidrólise de um éster

Triglicerídeos
Os triglicerídeos são moléculas de triéster compostas por uma estrutura de glicerol que se liga a 3 ácidos graxos. Estes formam a base de muitos ...

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soap formation from triglycerides

Triglycerides are lipids made of a glycerol backbone linked to three fatty acids. They are common in vegetable oils and animal fats. Plant lipids are the basis of vegetable oils, while animal lipids are used as lard or general sources of fats.

A fatty acid has a long carbon chain, usually between 12 and 20 carbons, with a weak organic acid at one end. Some fatty acids contain double bonds. These are unsaturated fats. The double bond usually gives the chain a bent, cis shape. As a result, unsaturated triglycerides do not stack evenly and have weaker attractions between molecules. They are usually liquid at room temperature. Saturated fats have only single bonds. Their chains are more regular, so they stack more easily. This gives them stronger attractions and higher melting points, which is why they are often solid at room temperature.

Triglycerides can also undergo hydrolysis because they contain ester groups. Hydrolysis is a reaction in which water breaks a bond. In ester hydrolysis, a nucleophile such as water or a hydroxide ion attacks the carbonyl carbon of the ester. One part of the molecule becomes an alcohol after gaining a hydrogen ion from water. The other part becomes a salt of a carboxylic acid after gaining the hydroxide group. Under normal conditions, only a few hydrolysis reactions occur without a strong acid or base. The acid or base acts as a catalyst and is recovered at the end. This reaction is reversible. It is also called a condensation reaction because water is formed as a side product.

The hydrolysis of triglycerides is one of the oldest examples of this chemistry and has been used for centuries to make soap. This reaction is called saponification. During saponification, hydroxide ions attack the carbonyl groups in the three ester bonds of the triglyceride. With three moles of sodium hydroxide for one mole of triglyceride, all three ester groups can be hydrolyzed. The products are three moles of soap molecules and one mole of glycerol. In practice, sodium hydroxide is often the limiting reagent so less triglyceride is left over. That helps reduce the drying effect of the soap.

Soap Formation from Triglycerides

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Soap Formation from Triglycerides

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