page_title: Butadiene
section_title: From ethanol
hierarchical_section_title: Butadiene / Production / From ethanol
caption_attribution_description: English: A reaction from ethanol to butadiene. Made with ChemSketch and the GIMP.
context_page_description: 1,3-Butadiene is the organic compound with the formula (CH₂=CH)₂. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a monomer in the production of synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene.
  Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles.
  The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H₂C=C=CH−CH₃. This allene has no industrial significance.
context_section_description: In other parts of the world, including South America, Eastern Europe, China, and India, butadiene is also produced from ethanol. While not competitive with steam cracking for producing large volumes of butadiene, lower capital costs make production from ethanol a viable option for smaller-capacity plants. Two processes were in use.
  In the single-step process developed by Sergei Lebedev, ethanol is converted to butadiene, hydrogen, and water at 400–450 °C over any of a variety of metal oxide catalysts:
  This process was the basis for the Soviet Union's synthetic rubber industry during and after World War II, and it remained in limited use in Russia and other parts of eastern Europe until the end of the 1970s. At the same time this type of manufacture was canceled in Brazil. As of 2017, no butadiene was produced industrially from ethanol.
  In the other, two-step process, developed by the Russian emigree chemist Ivan Ostromislensky, ethanol is oxidized to acetaldehyde, which reacts with additional ethanol over a tantalum-promoted porous silica catalyst at 325–350 °C to yield butadiene:
  This process was one of the three used in the United States to produce "government rubber" during World War II, although it is less economical than the butane or butene routes for the large volumes. Still, three plants with a total capacity of 200 KMTA were constructed in the U.S. (Institute, West Virginia, Louisville, Kentucky and Kobuta, Pennsylvania) with start-ups completed in 1943, the Louisville plant initially created butadiene from acetylene generated by an associated Calcium Carbide plant. The process remains in use today in China and India.
caption: CH3CH2OH + CH3CHO → CH2=CH−CH=CH2 + 2 H2O
exif: {}