ICI first produced MMA in the mid-1930s using a technology that is the basis for the acetone cyanohydrin route used in many plants today. Acetone and hydrogen cyanide are first reacted to produce acetone cyanohydrin. Sulphuric acid converts the cyanohydrin to methacrylamide sulphate which is then treated with a methanol/water mixture and heated to form MMA and ammonium bisulphate.
With problems in disposing the bisulphate waste, there has been much effort in finding solutions. For example, Mitsubishi Gas Chemical has commercialised an acetone cyanohydrin process that does not produce ammonium sulphate byproduct. The process generates a hydrocyanic acid byproduct which can be recycled as a raw material.
Evonik has also further developed the acetone cyanohydrin process avoiding the production of the ammonium bisulphate by-product. By using a new catalyst, it removes the need for sulphuric acid in the process along with the associated acid recovery unit. Evonik claims this leads to significant capital and operating cost savings.
Lucite International has developed an MMA process which uses readily available feedstocks ethylene, methanol and carbon monoxide and is said to produce only benign waste products. Called Alpha, the process is claimed to reduce the total cost of production by 40% and operates at mild conditions involving no toxic or corrosive chemicals. The first commercial application of the process will be in a 120,000 tonnes/year plant in Singapore, due on-stream in 2008.
The Alpha process consists, in essence, of three steps: two separate catalytic reactions and a complex series of distillations in the final product separation stage. Development of the two catalysts and the separation stage has all been central to realising the process, and each is covered by a number of key patents.
In the first stage, ethylene, carbon monoxide and methanol are reacted in the liquid phase at very mild conditions (10 bar and 100oC) over a homogeneous palladium-based phosphine ligand catalyst, to produce methylpropionate (MeP), with essentially no by-products. The MeP is then used in the second step, to react with formaldehyde in the gaseous phase over a fixed bed heterogeneous catalyst in the presence of methanol, to produce MMA and water. The MMA is then separated from the other constituents using six distillation steps, ultimately producing a product stream, recycle stream and waste stream.
In Japan, some production is based on isobutylene or tert-butyl alcohol feedstocks. With air and steam, the tert-butyl alcohol is fed to a reactor containing a metal oxide catalyst system to make methacrolein, which is further reacted in the presence of a phosphorus-molybdenum catalyst to make methacrylic acid. Esterification with methanol produces crude MMA which is purified by distillation.
Evonik is using a new C4 technology based on isobutylene in its planned 100,000 tonnes/year plant in Shanghai, China, due to start up in 2009. Evonik has obtained a technology licence from an unspecified Japanese chemical company and has combined the technology with its knowledge in catalytic oxidation.
Eastman Chemical, Research Triangle Institute and Bechtel have developed a three-step syngas process. The first step of the new process is the production of propionic acid from ethylene and syngas - the source of carbon monoxide in the reaction - using a homogeneous iodine-promoted molybdenum-based hydrocarbonylation catalyst. The reaction is described as low temperature (150-200oC) and low pressure (30-70 atmospheres) In the second step, propionic acid is reacted with formaldehyde to produce methacrylic acid (MAA) using a heterogeneous (silica supported) acid-base niobium-based bifunctional catalyst. Finally, esterification with methanol takes place to produce methyl methacrylate.
Methyl methacrylate
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Methyl methacrylate
Uses and Outlook
Nearly all methyl methacrylate (MMA) is polymerised to make homopolymers and copolymers with the largest application being the casting, moulding or extrusion of polymethyl methacrylate (PMMA) or modified polymers. This acrylic sheeting has clarity, weather-resistance and light weight properties making it a suitable substitute for glass in safety glazing, panels and illuminated light displays.
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