ACRYLIC ACID

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly 
to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons
 are produced annually.

Acrylic acid
Product

Acrylic acid is a colorless liquid above its freezing point of +13°C ( +56°F). It is fully miscible in water at +20°C (+68°F).
Acrylic acid will polymerize to form homopolymers and can be copolymerized with their esters and other vinyl monomers. Its carboxylic acid functionality provides anionic character and reactivity with alcohols and epoxides.

IUPAC name
Acrylic acid
Systematic IUPAC name
Prop-2-enoic acid
Other names
Acrylic acid
Acroleic acid
Ethylenecarboxylic acid
Propenoic acid
Vinylformic acid

Acrylic acid (GAA) is made by the direct oxidation of propylene. It is a raw material for various esters, super absorbent polymers (SAP), dispersants, flocculants, thickening agents, and adhesives.
EINECS: No. 201-177-9

History
The word "acrylic" was coined in 1843, for a chemical derivative of acrolein, an acrid-smelling oil derived from glycerol.

Production
Acrylic acid is produced by oxidation of propylene, which is a byproduct of the production of ethylene and gasoline:

CH2=CHCH3 + ​3⁄2 O2 → CH2=CHCO2H + H2O
Historical methods
Because acrylic acid and its esters have long been valued commercially, many other methods have been developed. Most have been abandoned for economic or environmental reasons. An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):

Acrylic acid synthesis from acethylene.png
This method requires nickel carbonyl, high pressures of carbon monoxide, and acetylene, which is relatively expensive compared to propylene.

Acrylic acid was once manufactured by the hydrolysis of acrylonitrile, a material derived from propene by ammoxidation, but this route was abandoned because it cogenerates ammonium side products, which must be disposed of. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.[6]

Research
Propane is a significantly cheaper raw material than propylene, so one alternative route being explored is the one-step selective oxidation of propane.

Carboxylating ethylene to acrylic acid under supercritical carbon dioxide condition is thermodynamically possible, but efficient catalysts have not been developed. 3-Hydroxypropionic acid (3HP), an acrylic-acid precursor by dehydration, can be produced from sugars, but the process is not competitive.[9][10]

Reactions and uses
Acrylic acid undergoes the typical reactions of a carboxylic acid. When reacted with an alcohol, it forms the corresponding ester. The esters and salts of acrylic acid are collectively known as acrylates (or propenoates). The most common alkyl esters of acrylic acid are methyl, butyl, ethyl, and 2-ethylhexyl acrylate.

Acrylic acid and its esters readily combine with themselves (to form polyacrylic acid) or other monomers (e.g. acrylamides, acrylonitrile, vinyl compounds, styrene, and butadiene) by reacting at their double bond, forming homopolymers or copolymers, which are used in the manufacture of various plastics, coatings, adhesives, elastomers, as well as floor polishes and paints.

Acrylic acid is a compound, which is used in many industries like the diaper industry, the water treatment industry or the textiles industry. On a worldwide scale the consumption rate of acrylic acid is projected to reach more than an estimated 8,000 kilotons, by 2020. This increase is expected to occur as a result of using this product in new applications, including personal care products, detergents and products that are used for adult incontinence.[11]

Substituents
As a substituent acrylic acid can be found as an acyl group or a carboxyalkyl group, depending on the removal of the group from the molecule.

More specifically, these are:

The acryloyl group, with the removal of the −OH from carbon-1.
The 2-carboxyethenyl group, with the removal of a −H from carbon-3. This substituent group is found in chlorophyll.
Safety
Acrylic acid is severely irritating and corrosive to the skin and the respiratory tract. Eye contact can result in severe and irreversible injury. Low exposure will cause minimal 
or no health effects, while high exposure could result in pulmonary edema. The LD50 is 340 mg/kg (rat, oral).

Acrylic acid is a constituent of tobacco smoke.

Acrylic acid, also known as 2-propenoic acid or acrylate, belongs to the class of organic compounds known as acrylic acids. These are organic compounds containing acrylic acid CH2=CHCO2H.
 Acrylic acid exists as a liquid, soluble (in water), and a weakly acidic compound (based on its pKa). Acrylic acid has been primarily detected in saliva. Within the cell, acrylic acid
 is primarily located in the cytoplasm. Acrylic acid participates in a number of enzymatic reactions. In particular, Acrylic acid can be biosynthesized from acrolein; which is catalyzed 
by the enzymes retinal dehydrogenase 1 and aldehyde dehydrogenase, dimeric nadp-preferring. In addition, Acrylic acid can be biosynthesized from acrolein; which is catalyzed by the 
enzymes retinal dehydrogenase 1 and aldehyde dehydrogenase, dimeric nadp-preferring. In humans, acrylic acid is involved in the ifosfamide metabolism pathway, the cyclophosphamide
 metabolism pathway, the cyclophosphamide action pathway, and the ifosfamide action pathway. Outside of the human body, acrylic acid can be found in pineapple. This makes acrylic 
acid a potential biomarker for the consumption of this food product.

Acrylic acid, [waste] appears as a colorless liquid with a distinctive acrid odor. Combustible. Flash point 130°F. Boiling point 286°F. Freezing point 121°F. Corrosive to metals and 
tissue. May polymerize under prolonged exposure to fire or heat. If polymerization occurs in a container violent rupture may occur. Generally shipped with an inhibitor such as 
hydroquinone to prevent polymerization.

CAMEO Chemicals
Acrylic acid is a colorless liquid with a distinctive acrid odor. Flash point 130°F. Boiling point 286°F. Freezing point 53°F. Corrosive to metals and tissue. Prolonged exposure
 to fire or heat can cause polymerization. If polymerization takes place in a closed container, violent rupture may occur. The inhibitor (usually hydroquinone) greatly reduces the
 tendency to polymerize.

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.[5]

Production
Acrylic acid is produced from propylene, which is a byproduct of ethylene and gasoline production:

CH2=CHCH3 + ​3⁄2 O2 → CH2=CHCO2H + H2O
Because propane is a significantly cheaper raw material than propylene, considerable research efforts are being undertaken to develop a process based on the one-step selective oxidation
of propane to acrylic acid.[6][7][8][9] Carboxylating ethylene to acrylic acid under supercritical carbon dioxide condition is thermodynamically possible when an efficient catalyst is 
developed.[10]

Because acrylic acid and its esters have long been valued commercially, many other methods have been developed, but most have been abandoned for economic or environmental reasons. 
An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):

HCCH + CO + H2O → CH2=CHCO2H
This method requires nickel carbonyl and high pressures of carbon monoxide. It[clarification needed] was once manufactured by the hydrolysis of acrylonitrile, which is derived from 
propene by ammoxidation, but was abandoned[clarification needed] because the method[which?] cogenerates ammonium derivatives. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.[5]

Reactions and uses
Acrylic acid undergoes the typical reactions of a carboxylic acid. When reacted with an alcohol, it forms the corresponding ester. The esters and salts of acrylic acid are collectively
 known as acrylates (or propenoates). The most common alkyl esters of acrylic acid are methyl, butyl, ethyl, and 2-ethylhexyl acrylate.

Acrylic acid and its esters readily combine with themselves (to form polyacrylic acid) or other monomers (e.g. acrylamides, acrylonitrile, vinyl compounds, styrene, and butadiene)
 by reacting at their double bond, forming homopolymers or copolymers, which are used in the manufacture of various plastics, coatings, adhesives, elastomers, as well as floor polishes and paints.

Acrylic acid is a compound, which is used of many industries like the diaper industry, the water treatment industry or the textiles industry. On a worldwide scale the consumption 
rate of acrylic acid is projected to reach more than an estimated 8,000 kilo tons, by 2020. This increase is expected to occur as a result of using this product in new applications, 
including personal care products, detergents and products that are used for adult incontinence.

Substituents
As a substituent acrylic acid can be found as an acyl group or a carboxyalkyl group, depending on the removal of the group from the molecule. More specifically, these are:

The acryloyl group, with the removal of the −OH from carbon-1.
The 2-carboxyethenyl group, with the removal of a −H from carbon-3. This substituent group is found in chlorophyll.
Safety
Acrylic acid is severely irritating and corrosive to the skin and the respiratory tract. Eye contact can result in severe and irreversible injury. Low exposure will cause minimal
 or no health effects, while high exposure could result in pulmonary edema. The LD50 is 340 mg/kg (rat, oral).

2-Propenoic acid

Acide acrylique

Acido acrilio

Acroleic acid

Acrylic acid

Acrylic acid, glacial

ACRYLIC ACID, STABILIZED

acrylic acid; prop-2-enoic acid

Ethylenecarboxylic acid

Glacial acrylic acid

Kyselina akrylova

Prop-2-enoic acid

Propene acid

Propenoic acid

Vinylformic acid

Translated names
2-propeno rūgštis (lt)

2-propensyra (sv)

2-propensyre (no)

acid acrilic (ro)

acid prop-2-enoic (ro)

acide acrylique; acide prop-2-énoïque (fr)

acido acrilico (it)

acrylsyre (da)

Acrylsäure (de)

acrylzuur (nl)

akrilna kiselina (hr)
C
akrilna kislina (sl)

akrilo rūgštis (lt)

akrilsav (hu)

akrilskābe (lv)

akrylová kyselina (cs)

akrylsyra (sv)

akrylsyre (no)

Akryylihappo (fi)

Akrüülhape (et)

kwas akrylowy (pl)

kwas etenokarboksylowy (pl)

kwas propenowy (pl)

kyselina akrylová (sk)

kyselina propénová (sk)

Prop-2-eenhape (et)

Prop-2-eenihappo (fi)

prop-2-enojska kislina (sl)
C
prop-2-enonska kiselina (hr)

prop-2-enová kyselina (cs)

prop-2-énsav (hu)

Propensäure (de)

propēn-2 skābe (lv)

ácido 2-propenoico (es)
ácido 2-propenóico (pt)
ácido acrílico (es)
ακρυλικο οξύ (el)
акрилова киселина (bg)
проп-2-енова киселина (bg)

IUPAC names
2-hydroxyethyl methacrylate
AA
Acrylic Acid (stabilized with MEHQ)
Acrylic acid - MQ0028B
acrylic acid, acrylic acid glacial, acrylic acid technical
acrylicacid
prop-2-enoate

Trade names
2-Propenoic acid (9CI)

Acrylic acid (6CI, 7CI, 8CI)

Acrylsaeure

AQUAPEARL E-200

AQUAPEARL HPS

High Purity Acrylic Acid