MTBE is highly flammable and is widely used as an oxygenate.

MTBE (methyl tertiary-butyl ether) is a chemical compound that is manufactured by the chemical reaction of methanol and isobutylene. MTBE is produced in very large quantities (more than 200,000 barrels per day in the United States in 1999) and is almost exclusively used as a fuel component in motor gasoline. It is one of a group of chemicals commonly known as oxygenates because they raise the oxygen content of gasoline. At room temperature, MTBE is a volatile, flammable and colorless liquid that is relatively soluble in water. MTBE has a typical odor reminiscent of diethyl ether. MTBE is increasingly used in organic chemistry as a cheap solvent with properties comparable to diethyl ether but with a higher boiling point and lower solubility for water. Methyl tertiary butyl ether Produced by myself. ... A chemical substance is any material substance used in or obtained by a process in chemistry: A chemical compound is a substance consisting of two or more chemical elements that are chemically combined in fixed proportions. ... Jump to: navigation, search A chemical reaction is a process involving one, two or more substances (called reactants), characterized by a chemical change and yielding one or more product(s) which are different from the reactants. ... Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid that is used as an antifreeze, solvent, fuel, and as a denaturant for ethyl alcohol. ... 1-butene cis-2-butene trans-2-butene methylpropene There are four alkenes which have four carbon atoms and one double bond in their chemical structure. ... The barrel is the name of several units of measurement. ... Jump to: navigation, search 1999(MCMXCIX) is a common year starting on Friday Anno Domini (or the Current Era), and was designated the International Year of Older Persons by the United Nations. ... Gasoline, as it is known in North America, or petrol, in many Commonwealth countries (sometimes also called motor spirit) is a petroleum-derived liquid mixture consisting primarily of hydrocarbons, used as fuel in internal combustion engines. ... A fuel additive containing Oxygen in its chemical makeup. ... Jump to: navigation, search General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. ... Jump to: navigation, search Organic chemistry is the scientific study of the structure, properties, composition, reactions, and synthesis of organic compounds that by definition contain carbon. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Jump to: navigation, search Allah is who made all of this. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Jump to: navigation, search Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ...

MTBE has been used in U.S. gasoline at low levels since 1979 to replace tetra-ethyl lead as an octane enhancer and to help prevent engine knocking. Since 1992, MTBE has been used at higher concentrations in some gasoline to fulfill the oxygenate requirements set by Congress in Clean Air Act amendments. Jump to: navigation, search This page refers to the year 1979. ... Tetra-ethyl lead (also known as TEL, lead tetraethyl and tetraethyllead) is a toxic organometallic chemical compound, with formula (CH3CH2)4Pb, which was once used as a gasoline (petrol) additive. ... Octane is an alkane hydrocarbon with the chemical formula CH3(CH2)6CH3. ... Jump to: navigation, search Knocking (also called pinking or pinging)—technically detonation—in internal combustion engines occurs when fuel in the cylinder is ignited by the firing of the spark plug and smooth burning proceeds but some of the unburned mixture in the combustion chamber explodes before the flame front... Jump to: navigation, search 1992 (MCMXCII) was a leap year starting on Wednesday. ... Jump to: navigation, search A congress is a gathering of people, especially a gathering for a political purpose. ... A Clean Air Act may be one of a number of pieces of legislation relating to reduction of smog and atmospheric pollution in general. ...

Oxygen helps gasoline burn more completely, reducing harmful tailpipe emissions from motor vehicles. In one respect, the oxygen dilutes or displaces gasoline components such as aromatics (e.g., benzene) and sulfur. In another, oxygen optimizes the oxidation during combustion. Most refiners have chosen to use MTBE over other oxygenates primarily for its blending characteristics and for economic reasons.

In 1995 high levels of MTBE were unexpectedly discovered in the water wells of Santa Monica, California. Subsequent tests found tens of thousands of contaminated sites across the country. This is attributed to the lack of effective regulations for underground storage tanks, as the EU does not predict the same problem in Europe [1]. Jump to: navigation, search 1995 (MCMXCV) was a common year starting on Sunday of the Gregorian calendar. ... Jump to: navigation, search A water well is an arrangement that makes water beneath the earths surface available to serve human purposes. ... Santa Monica Pier Santa Monica is a coastal city located in western Los Angeles County, California, USA, by the Pacific Ocean, south of Pacific Palisades and Brentwood, west of Westwood, Los Angeles, and north of Venice. ...

Potential health risks

Advocates of MTBE contend that it has no harmful effects on humans, although its manufacturers did not test it for its effects on human health before introducing it as an additive. As of today, researchers have limited data about what the health effects may be if a person swallows (ingests) MTBE. The Environmental Protection Agency (EPA) has concluded that available data are not adequate to estimate potential health risks of MTBE at low exposure levels in drinking water but that the data support the conclusion that MTBE is a potential human carcinogen at high doses.[2] Jump to: navigation, search EPA redirects here. ... In pathology, a carcinogen is any substance or agent that promotes cancer. ...

MTBE often ends up in drinking water, e.g. when oil storage tanks leak near populated areas. However, so far there are no reported cases of a person becoming sick from MTBE in drinking water. Aside from the health risks, MTBE negatively affects the taste and odor of the drinking water even at very low levels. Jump to: navigation, search Drinking water Drinking water is water that is intended to be drunk by humans. ...

As an ether, MTBE acts as an emulsifier, increasing the solubility of other, harmful components of gasoline. It thus may increase the risk of contamination by other compounds. MTBE biodegrades very slowly, remaining in water for decades or more. Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... An emulsion is a mixture of two immiscible substances. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Biodegradation is the decomposition of organic material by microorganisms. ...

Alternatives

Other, safer compounds (such as ethanol) are available. Reasons for using MTBE include economical considerations, as some of the production is obtained by adding methanol to isobutylene produced as a by-product of other processes. However, most MTBE facilities have to manufacture the methanol and isobutylene required to produce MTBE. Jump to: navigation, search Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ... Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid that is used as an antifreeze, solvent, fuel, and as a denaturant for ethyl alcohol. ... 1-butene cis-2-butene trans-2-butene methylpropene There are four alkenes which have four carbon atoms and one double bond in their chemical structure. ...

Advocates in the United States sometimes claim that gasoline manufacturers have been forced to add MTBE to gasoline by law. However, this is incorrect, since any oxygenate would fulfill the law. A fuel additive containing Oxygen in its chemical makeup. ...

In 2003, California was the first state to start replacing the MTBE with ethanol. Several other states started switching soon afterward.

Legislation

United States

The clean-up of all MTBE in the U.S. is estimated to cost as much as $140 billion, including breaking down the compound in municipal water supplies and repairing leaky underground oil tanks. Much of the controversy centers around who will have to pay the costs of this clean-up, if such a task is required.

Recent state laws have been passed to ban MTBE in certain areas. As of 2004, more than half of all states still permit its use. However, the states of California and New York, which together accounted for 40% of U.S. MTBE consumption, banned the chemical starting January 1, 2004. (A table of state by state information, as of 2002, is available here at the Department of Energy website. As of September 2005, 25 states in all have signed legislation on banning MTBE.) Jump to: navigation, search 2004 (MMIV) was a leap year starting on Thursday of the Gregorian calendar. ... Jump to: navigation, search State nickname: The Golden State Other U.S. States Capital Sacramento Largest city Los Angeles Governor Arnold Schwarzenegger (R) Senators Dianne Feinstein (D) Barbara Boxer (D) Official languages English Area 410,000 km² (3rd)  - Land 404,298 km²  - Water 20,047 km² (4. ... Jump to: navigation, search State nickname: The Empire State Other U.S. States Capital Albany Largest city New York City Governor George Pataki (R) Senators Charles Schumer (D) Hillary Rodham Clinton (D) Official languages None (English is de facto) Area 141,205 km² or 54,556 square miles (27th)  - Land... Jump to: navigation, search January 1 is the first day of the calendar year in both the Julian and Gregorian calendars. ... Jump to: navigation, search 2004 (MMIV) was a leap year starting on Thursday of the Gregorian calendar. ... The United States Department of Energy (DOE) is a Cabinet-level department of the United States government responsible for energy policy and nuclear safety. ...

In 2000, the EPA drafted plans to phase out the use of MTBE nationwide over four years. Upon taking office, the Bush administration cancelled those plans. Jump to: navigation, search This article is about the year 2000. ... Jump to: navigation, search George Walker Bush (born July 6, 1946) is the 43rd and current President of the United States and a former Governor of the State of Texas. ...

In April of 2002, a California jury found several oil companies guilty of irresponsibly manufacturing and distributing MTBE, stating that the companies acted with malice in failing to warn customers about the dangers of MTBE contamination. There are hundreds of other lawsuits currently active regarding the compound. Jump to: navigation, search 2002(MMII) is a common year starting on Tuesday of the Gregorian calendar. ... Jump to: navigation, search State nickname: The Golden State Other U.S. States Capital Sacramento Largest city Los Angeles Governor Arnold Schwarzenegger (R) Senators Dianne Feinstein (D) Barbara Boxer (D) Official languages English Area 410,000 km² (3rd)  - Land 404,298 km²  - Water 20,047 km² (4. ...

Between 2000 and 2004, the top three MTBE manufacturers have donated over $1 million to the United States Republican Party and key members. An amendment to provide blanket immunity from MTBE-related lawsuits was inserted into the House version of the 2003 Energy Bill. The bill failed to pass when six Republicans voted against it, mostly because of that amendment. MTBE lawsuit immunity is likely to remain a political issue in the years to come. The Republican Party, often called the GOP (for Grand Old Party, although one early citation described it as the Gallant Old Party) [1], is one of the two major political parties in the United States. ... Immunity confers a status on a person or body that makes that person or body free from otherwise legal obligations such as, for example, liability for damages or punishment for criminal acts. ... Jump to: navigation, search Seal of the House of Representatives The United States House of Representatives is one of the two houses of the Congress of the United States, the other being the Senate. ...

The Energy Policy Act of 2005, passed in the House on April 21, 2005, did not include a provision for shielding MTBE manufacturers from water contamination lawsuits. This provision had been a top priority of Tom DeLay and Rep. Joe Barton, chairman of the Energy and Commerce Committee. [3] This bill also includes a provision that gives MTBE makers, including some of the biggest oil companies, $2 billion in transition assistance as MTBE is phased out over the next nine years. [4] The New York Times calls this "A Dirty Little Footnote to the Energy Bill." [5]. Jump to: navigation, search The Energy Policy Act of 2005 (Public Law 109-58) is a statute which was passed by the United States Congress on July 29, 2005 and signed into law on August 8, 2005 at Sandia National Laboratories in Albuquerque, New Mexico. ... Water pollution has many sources and characteristics. ... Jump to: navigation, search Tom DeLay Thomas Dale DeLay (born April 8, 1947 in Laredo, Texas) is an American politician from Sugar Land, Texas and a prominent Republican. ... Congressman Joe Barton (left) Joe Linus Barton (born September 15, 1949), American politician, has been the Republican congressman representing the Texas 6th congressional district (map) in the U.S. House of Representatives since 1985. ... The Oil industry brings to market what is currently considered the lifeblood of nearly all other industry, if not industrialized civilization itself. ...

Due to opposition in the Senate, the conference report dropped all MTBE provisions. The final bill was passed by both houses and signed into law by President Bush. [6] MTBE could be addressed in a future bill, but it is unlikely to sustain support.

It should be noted that important patents in the manufacture of MTBE are not held by American companies; for example, United States patent 5536886, Process for preparing alkyl ethers [7], is owned by the Finnish company Neste. (Incidentally, the same corporation went on to patent the replacement of the MTBE process, an octane production process trademarked NExOCTANE.) Neste is a Finnish chain of service stations. ...

Chemistry

MTBE has a boiling point of 55 - 56 °C and forms azeotropes with water (52.6 °C) and methanol (51.3 °C). Jump to: navigation, search An azeotrope is a liquid mixture of two or more components which has a unique constant boiling point. ...

Being an ether, MTBE is a Lewis base. However, unlike other ethers such as diethyl ether or THF, it is does not coordinate well enough to magnesium to be used for making Grignard reagents. The tert-butyl group is easily cleaved off under strongly acidic conditions (forming a moderately stable carbocation), particularly if heated (isobutylene is lost), something which can limit the use of MTBE as a solvent. However it possesses one distinct advantage over most ethers- it has a much lower tendency to form explosive organic peroxides than most ethers. Opened bottles of diethyl ether or THF can build up dangerous levels of these peroxides in months, whereas samples of MTBE are usually safe for years - however they should still be tested periodically. A Lewis base is any molecule or ion that can form a new covalent bond by donating a pair of electrons. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. ... Tetrahydrofuran, also known as THF, hydrofuran, oxolane, oxacyclopentane, or furanidine, is a heterocyclic organic compound. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... In organic chemistry, butyl is a four-carbon alkyl substituent with chemical formula -C4H9. ... A carbocation is an ion with a positively-charged carbon atom. ... 1-butene cis-2-butene trans-2-butene methylpropene There are four alkenes which have four carbon atoms and one double bond in their chemical structure. ... Organic peroxides are organic molecules containing the peroxide functional group ROOR If the R is hydrogen, the compound is called organic hydroperoxide. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. ... Tetrahydrofuran, also known as THF, hydrofuran, oxolane, oxacyclopentane, or furanidine, is a heterocyclic organic compound. ...

References

• Harper's Magazine, August 2004, pp 73-64

External links

• MTBE webpage from the EPA