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Vinyl acetate

 

 
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Vinyl acetate
 
 
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Vinyl acetate is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate
Polyvinyl acetate

Polyvinyl acetate is a rubbery synthetic polymer. PVA is a common copolymer.It is prepared by polymerization of vinyl acetate, also referred to as VAM....
 (PVA), an important polymer in industry. Like many industrially significant compounds, vinyl acetate has numerous names and acronymns.

major industrial route involves the reaction of ethylene
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
 and acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
 with oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 in the presence of a palladium
Palladium

Palladium is a rare and lustrous silvery-white metal that was discovered in 1803 by William Hyde Wollaston, who named it palladium after the 2 Pallas, which in turn, was named after the epithet of the Greek mythology goddess Athena, acquired by her when she slew Athena#Pallas_Athena....
 catalyst.

Ethylene + acetic acid + 1/2 O2 ? Vinyl acetate + H2O
But also byproducts are also generated:
Ethylene + 3 O2 ? 2 CO2 + 2 H2O


Vinyl acetate is also prepared by the gas-phase addition of acetic acid to acetylene
Acetylene

Acetylene is the chemical compound with the symbol carbonhydrogen. It is the simplest alkyne.As an alkyne, acetylene is Saturation because its two carbon atoms are Chemical bond together in a triple bond....
.

an be polymerized, either by itself to make polyvinyl acetate or with other monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
s to prepare copolymers such as ethylene-vinyl acetate
Ethylene-vinyl acetate

Ethylene vinyl acetate is the heteropolymer of ethylene and vinyl acetate. The weight percent vinyl acetate usually varies from 10 to 40%, with the remainder being ethylene....
.






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Vinyl acetate is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate
Polyvinyl acetate

Polyvinyl acetate is a rubbery synthetic polymer. PVA is a common copolymer.It is prepared by polymerization of vinyl acetate, also referred to as VAM....
 (PVA), an important polymer in industry. Like many industrially significant compounds, vinyl acetate has numerous names and acronymns.

Preparation

The major industrial route involves the reaction of ethylene
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
 and acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
 with oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 in the presence of a palladium
Palladium

Palladium is a rare and lustrous silvery-white metal that was discovered in 1803 by William Hyde Wollaston, who named it palladium after the 2 Pallas, which in turn, was named after the epithet of the Greek mythology goddess Athena, acquired by her when she slew Athena#Pallas_Athena....
 catalyst.

Ethylene + acetic acid + 1/2 O2 ? Vinyl acetate + H2O
But also byproducts are also generated:
Ethylene + 3 O2 ? 2 CO2 + 2 H2O


Vinyl acetate is also prepared by the gas-phase addition of acetic acid to acetylene
Acetylene

Acetylene is the chemical compound with the symbol carbonhydrogen. It is the simplest alkyne.As an alkyne, acetylene is Saturation because its two carbon atoms are Chemical bond together in a triple bond....
.

Polymerization

It can be polymerized, either by itself to make polyvinyl acetate or with other monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
s to prepare copolymers such as ethylene-vinyl acetate
Ethylene-vinyl acetate

Ethylene vinyl acetate is the heteropolymer of ethylene and vinyl acetate. The weight percent vinyl acetate usually varies from 10 to 40%, with the remainder being ethylene....
. Due to the instability of the radical, attempts to control the polymerization via most 'living/controlled' radical processes have proved problematic. However, RAFT
RAFT (chemistry)

RAFT or Reversible addition–fragmentation chain transfer is a form of Living polymerization.Reversible addition–fragmentation chain transfer polymerization was discovered by the in 1998....
 (or more specifically MADIX) polymerization offers a convenient method of controlling the synthesis of PVA by the addition of a xanthate chain transfer agent.

Other derivatives

Vinyl acetate undergoes many of the reactions anticipated for an alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
 and an ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
. Bromine
Bromine

Bromine , , meaning "stench " ), is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown Volatility liquid at Standard conditions for temperature and pressure that is intermediate in reactivity between chlorine and iodine....
 adds to give the dibromide. Hydrogen halides add to give 1-haloethyl acetates, which cannot be generate by other methods because of the non-availability of the corresponding halo-alcohols. Acetic acid adds in the presence of palladium catalysts to give ethylidene diacetate, CH3CH(OAc)2. It undergoes transesterification with a variety of carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s. The alkene also undergoes Diels-Alder and 2+2 cycloadditions.

Possible label as "toxic" in Canada

Due to research done by the International Agency for Research on Cancer
International Agency for Research on Cancer

The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organisation of the United Nations....
 that the substance could be linked to cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
 in lab rats, a draft report due from the Government of Canada may label it toxic, along with as many as sixteen other substances.

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