science

Methyl acrylate

Methyl acrylate is a science topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Methyl acrylate rather than just read about it. In short: Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor.

Key takeaways

Methyl acrylate belongs to science; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Methyl acrylate to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Methyl acrylate from memory before moving on to harder problems.

Reference excerpt

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain a polymerisation inhibitor such as hydroquinone.

Production The standard industrial reaction for producing methyl acrylate is esterification of acrylic acid with methanol under acid catalysis (sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers.). The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (boiling point 62–63 °C). The patent literature describes a one-pot route involving vapor-phase oxidation of propene or 2-propenal with oxygen in the presence of methanol.

Other methods Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc. Methyl acrylate is formed in good yield on pyrolysis of methyl lactate in the presence of ethenone (ketene). Methyl lactate is a renewable "green chemical". Another patent describes the dehydration of methyl lactate over zeolites. The nickel tetracarbonyl-catalyzed hydrocarboxylation of acetylene with carbon monoxide in the presence of methanol also yields methyl acrylate. The reaction of methyl formate with acetylene in the presence of transition metal catalysts also leads to methyl acrylate. Both, the alcoholysis of propiolactone with methanol as well as the methanolysis of acrylonitrile via intermediately formed acrylamide sulfate are also proven but obsolete processes.

Use Methyl acrylate is after butyl acrylate and ethyl acrylate the third most important acrylic ester with a worldwide annual production of about 200,000 tons in 2007. Poly(methyl acrylate) is a tacky material near room temperature, and as such it is not particularly useful as a structural material. Commonly, methyl acrylate (and other acrylate esters) are copolymerized with other alkenes to give useful engineering plastics. A variety of vinyl monomers are used, including styrene and other acrylates. The resulting copolymers give acrylic paints that are harder and more brittle than those with the homologous acrylates. Copolymerizing methyl acrylate with acrylonitrile improves their melt processability to fibers, which could be used as precursors for carbon fibers. Methyl acrylate is the precursor to fibers that are woven to make carpets.

Amino derivatives Methyl acrylate reacts catalysed by Lewis bases in a Michael addition with amines in high yields to β-alanine derivatives which provide amphoteric surfactants when long-chain amines are used and the ester function is hydrolysed subsequently. Acrylates are also used in the preparation of poly(amidoamine) (PAMAM) dendrimers typically by Michael addition with a primary amine.

Methyl acrylate is used for the preparation of 2-dimethylaminoethyl acrylate by transesterification with dimethylaminoethanol in significant quantities of over 50,000 tons / year.

Reactions Methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example, in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether:

2 CH2CHCO2CH3 + H2S → S(CH2CH2CO2CH3)2 It is also a good dienophile.

Safety It is an acute toxin with an LD50 (rats, oral) of 300 mg/kg and a TLV of 10 ppm.

References

Illustrations

Worked examples

Example 1 — a first encounter with Methyl acrylate

Start with the simplest possible case. Write down what Methyl acrylate claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Methyl acrylate before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Methyl acrylate ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Methyl acrylate

In research: Methyl acrylate appears in science research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Methyl acrylate in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Methyl acrylate is common in secondary-school and first-year university syllabi. It links to neighbouring topics Acrylate esters, Methyl esters, Monomers, so understanding it makes those chapters shorter.
In everyday life: Look for Methyl acrylate outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Methyl acrylate in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Methyl acrylate means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Methyl acrylate out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Methyl acrylate in simple terms?

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor.

Why does Methyl acrylate matter?

Because it connects several science ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Methyl acrylate?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Methyl acrylate.