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Cumene
Overview
Cumene (KYOO-meen) is a colorless, flammable liquid with a penetrating gasoline-like odor. Chemically, it is classified as an aromatic hydrocarbon. Aromatic hydrocarbons are compounds of carbon and hydrogen with a
molecular structure based on that of benzene. Although cumene is probably not well known to the average person, it is a very important industrial chemical. In 2004, some 3.74 million metric tons(4.12 million short tons) of cumene were produced in the United States, making it the twentieth most important chemical made in that year by weight. Cumene is used primarily as a raw material in the synthesis of other organic compounds, such as phenol, acetone, acetophenone, and methyl styrene, and as a thinner for paints and lacquers.
Key Facts
Other Names:
Isopropylbenzene;1-(methylethyl) benzene
Formula:
C6H5CH(CH3)2
Elements:
Carbon, hydrogen
Compound Type:
Liquid
Molecular Weight:
120.19 g/mol
Melting Point:
96.02C ( 140.8F)
Boiling Point:
152.41C (306.34F)
Solubility:
Insoluble in water; miscible with ethyl alcohol, benzene, ether, acetone, and most organic solvents
How It Is Made
Cumene is made in a straight-forward chemical reaction between benzene (C6H6) and propene (propylene; CH3CH=CH2). It can also be extracted from petroleum or from coal tar, the thick black material left after soft coal is converted to coke.
Interesting Facts
Traditionally, the synthesis of cumene has involved the use of phosphoric acid (H3PO4) as a catalyst. That process results in the release of harmful by-products into the environment, and a new process that uses zeolites as a catalyst has now become more popular. Zeolites are a naturally occurring, earthy material that can be as effective as phosphoric acid in promoting the synthesis of cumene
Badger Licensing to Provide Technology for New Cumene Plant in Shanghai, China
CAMBRIDGE, Mass.--(BUSINESS WIRE)--Badger Licensing LLC (Badger) today announced that Shanghai Sinopec Mitsui Chemicals, Co., Ltd. (SSMC), a joint venture of China Petroleum & Chemical Corporation (Sinopec) and Mitsui Chemicals, Inc., has selected Badger to provide its proprietary technology for a 332,500 metric ton per annum grassroots cumene plant to be built in Shanghai, Peoples Republic of China. The contract includes technology license, process design, and start-up services.
Both Sinopec and Mitsui are key players in the phenolics industry
The new cumene plant is scheduled for mechanical completion and startup in 2013 and will be integrated with SSMCs phenol plant currently being constructed at the same site. Another cumene/phenol plant is operated by Sinopec in Shanghai, which also uses Badgers proprietary cumene technology.
Both Sinopec and Mitsui are key players in the phenolics industry, said Mark Healey, president of Badger. These two industry leaders together with their SSMC joint venture have now licensed Badgers cumene technology a total of four times, which clearly demonstrates the high level of customer satisfaction enjoyed by our licensees. We look forward to continuing our excellent relationship with SSMC, Sinopec, and Mitsui on this project and into the future. More than nine million metric tons of cumene capacity has been licensed by Badger and its predecessor companies since the technology was introduced in 1995. Badger Licensing LLC, headquartered in Cambridge, MA, USA, is a venture of affiliates of The Shaw Group (NYSE: SHAW) and ExxonMobil Chemical Company. Badger Licensing is principally engaged in marketing, licensing, and developing technologies for ethylbenzene, styrene monomer, cumene, and bisphenol A. The venture also supplies basic engineering packages for the licensed processes through Shaw. Catalysts for ethylbenzene and cumene processes are supplied to Badgers licensees by ExxonMobil Catalyst Technologies LLC. Editor's Notes: 1. Badger Licensing LLC is a joint venture between Badger Technology Holdings LLC (affiliate of The Shaw Group Inc.) and Alkylation Licensing LLC (affiliate of ExxonMobil Chemical Company).
Contacts
Badger Licensing LLC Mary Kelleher, 1.617.494.7217 mary.kelleher@badgerlicensing.com
http://www.businesswire.com/news/home/20120314005049/en/Badger-Licensing-Provide-TechnologyCumene-Plant-Shanghai
http://www.gtforum.com/gtf/release/2136854/uop-wins-south-korea-contract-cumene-phenoltechnology
South KoreaUOPPhenolCumenePetrochemicals
in Share New units to start up in 20132014, with 900,000tpa of cumene capacity and 300,000tpa of phenol.
UOP LLC, a Honeywell company, announced today that it has been selected by South Koreas Kumho P&B Chemicals, Inc. to provide technology to produce key petrochemicals for the manufacture of plastics. Honeywells UOP Q-Max and UOP Phenol process technologies will be integrated at Kumhos Yeosu, South Korea facility to produce high-quality phenol. According to industry consultants, the demand for materials produced using these petrochemicals is forecasted to grow in Asia by as much as 9% annually over the next five years, driven by demand for automobiles, appliances and electronics. The new units, expected to start up in 20132014, will produce 900,000 metric tons per annum (tpa) of cumene and 300,000tpa of phenol. UOP will provide engineering design, technology licensing, catalysts, adsorbents and technical service for the project. The UOP Q-Max process produces high-quality cumene through the alkylation of benzene with propylene. The cumene is subsequently converted to high-quality phenol, with low feedstock and utility requirements, using the UOP Phenol process. The UOP Q-Max process uses a robust and efficient catalyst system, which maximises on-stream time, and minimises raw material and energy consumption. To date, the total licensed UOP Q-Max production capacity exceeds 5.8 million tpa. UOPs total
licensed phenol production capacity exceeds 3.4 million tpa. Founded in 1976, Kumho P&B Chemicals, Inc. specialises in the production of phenol and its derivatives, and leads the Asian phenol industry. The company is based in Yeosu, South Korea, and is a subsidiary of Koreas Kumho Petrochemical Company.
http://www.icis.com/Articles/2007/11/01/9075199/cumene-uses-and-market-data.html
The largest phenol derivative is bisphenol-A (BPA) which supplies the growing polycarbonate (PC) sector. PC resins are consumed in automotive applications in place of traditional materials such as glass and metals. Glazing and sheet uses, such as architectural, security and glazing outlets, are also important PC applications. The third largest use for PC is optical media such as compact discs (CDs) and digital versatile discs (DVDs).
PC resins consumption has slowed with the softening of the automotive sector. The strong growth in optical media has driven the PC market but growth in this market has been slowing and expected to go into decline as it becomes replaced by MP3 players, high internet bandwidth and USB drives.
PC plastic bottles containing hot liquids have attracted the attention of environmentalists in that BPA can be released from the bottles leading to health concerns. As a result, some PC bottles for baby foods have been removed from supermarkets although this is a small market for polycarbonate.
BPAs other main derivative is epoxy resins which are used in high performance coatings, electricalelectronic laminates, adhesives, flooring and paving applications, and composites. Growth in these markets is close to GDP levels.
Phenols other derivatives include phenolic resins which are largely used as durable binders and adhesives in structural wood panels and as binders in mineral wool insulation. Demand here is tied closely to the home construction market.
Another phenol derivative is caprolactam which is used mainly to make nylon 6. It is mainly the engineering resin sector of the nylon market that is seeing growth.
The key drivers in the acetone market are methyl methacrylate (MMA) and BPA. Nearly all MMA is used to make homopolymers and copolymers with electronic applications such as flat screen TVs and liquid crystal displays providing growth opportunities. However, a significant outlet for acetone is the solvent sector where market growth is stagnant.
According to US-based consultants DeWitt & Co, the consumption of cumene fell in relation to other benzene derivatives in 2009. Phenol demand in 2009 was 8% below the peak in 2007 with the fall concentrated in Europe and the US.
However, Asia operates close to capacity and will be short of product in the next three years if growth is sustained. Europe could profit from the tightness in Asia to increase operating rates.
The US will also increase phenol exports but without a significant pick-up in domestic demand, it may see rationalization, adds DeWitt. The US propylene advantage is declining with lower refinery operating rates and US benzene is likely to remain expensive.
Cumene is linked closely to the phenol and acetone markets. Please see phenol uses and outlook and acetone uses and outlook.
http://enggyd.blogspot.in/2010/07/cumene-production-material-balance.html
http://pubs.rsc.org/en/content/articlehtml/2004/gc/b403277m