Isobutanol

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Isobutanol
Skeletal formula of isobutanol
Ball-and-stick model of isobutanol
Identifiers
CAS number 78-83-1 YesY
PubChem 6560
ChemSpider 6312 YesY
UNII 56F9Z98TEM YesY
EC-number 201-148-0
KEGG C14710 YesY
ChEBI CHEBI:46645 YesY
ChEMBL CHEMBL269630 YesY
RTECS number NP9625000
Jmol-3D images Image 1
Properties[2]
Molecular formula C4H10O
Molar mass 74.122 g/mol
Appearance Colorless liquid
Density 0.802 g/cm3, liquid
Melting point −101.9 °C (−151.4 °F; 171.2 K)
Boiling point 107.89 °C (226.20 °F; 381.04 K)
Solubility in water 8.7 mL/100 mL[1]
log P 0.8
Refractive index (nD) 1.3959
Viscosity 3.95 cP at 20 °C
Hazards[2]
MSDS ICSC 0113
EU Index 603-108-00-1
EU classification Irritant (Xi)
R-phrases R10 R37/38 R41, R67
S-phrases (S2) S7/9 S13 S26 S37/39 S46
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 28 °C (82 °F; 301 K)
Explosive limits 1.7–10.9%
Related compounds
Related butanols n-Butanol
sec-Butanol
tert-Butanol
Related compounds Isobutyraldehyde
Isobutyric acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH. This colorless, flammable liquid with a characteristic smell is mainly used as a solvent. Its isomers include n-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

Production[edit]

Isobutanol is produced by the carbonylation of propylene. Two methods are practiced industrially, hydroformylation is more common and generates a mixture of isobutyraldehydes, which are hydrogenated to the alcohols and then separated. Reppe carbonylation is also practiced.[3]

Biosynthesis of Isobutanol[edit]

Isobutanol is also produced naturally during the fermentation of carbohydrates and may also be a byproduct of the decay process of organic matter.[4] The biosynthetic pathway used to produce isobutanol was first discovered in species of bacteria from the genus Clostridium. This pathway has been genetically engineered into several species of microorganisms which are more easily manipulated by current scientific methods than microorganisms of the genus Clostridium.[5] Although these engineered organisms are capable of producing isobutanol, they have not yet achieved the ability to produce isobutanol in quantities large enough for commercial use.[5] These organisms are being moved toward commercialization through genetic modifications which allow higher yields of isobutanol.[5] The organisms being pursued as commercial isobutanol producers are listed below:

Cyanobacteria[edit]

Cyanobacteria, are a phylum of photosynthetic bacteria.[6] Cyanobacteria are suited for isobutanol biosynthesis when genetically engineered to produce isobutanol. Isobutanol producing species of cyanobacteria offer several advantages as biofuel synthesizers:

  • Cyanobacteria grow faster than plants[7] and also absorb sunlight more efficiently than plants.[8] This means they can be replenished at a faster rate than the plant matter used for other biofuel biosynthesizers.
  • Cyanobacteria can be grown on non-arable land (land not used for farming).[7] This prevents competition between food sources and fuel sources.[7]
  • The supplements necessary for the growth of Cyanobacteria are CO2, H2O, and sunlight.[8] This presents two advantages:
    • Because CO2 is derived from the atmosphere, Cyanobacteria do not need plant matter to synthesize isobutanol (in other organisms which synthesize isobutanol, plant matter is the source of the carbon necessary to synthetically assemble isobutanol).[8] Since plant matter is not used by this method of isobutanol production, the necessity to source plant matter from food sources and create a food-fuel price relationship is avoided.[7]
    • Because CO2 is absorbed from the atmosphere by Cyanobacteria, the possibility of bioremediation (in the form of Cyanobacteria removing excess CO2 from the atmosphere) exists.[8]

The primary drawbacks of Cyanobacteria are:

  • Cyanobacteria are sensitive to environmental conditions when being grown. Cyanobacteria suffer greatly from sunlight of inappropriate wavelength and intensity, CO2 of inappropriate concentration, or H2O of inappropriate salinity. These factors are generally hard to control, and present a major obstacle in cyanbacterial production of isobutanol.[9]
  • Cyanobacteria bioreactors require high energy to operate. Cultures require constant mixing, and the harvesting of biosynthetic products is energy intensive. This reduces the efficiency of isobutanol production via Cyanobacteria.[9]

Escherichia coli[edit]

Escherichia coli, or E. coli, is a Gram-negative, rod-shaped bacteria. E. coli is the microorganism most likely to move on to commercial production of isobutanol.[5] In its engineered form E. coli produces the highest yields of isobutanol of any microorganism.[5] Methods such as elementary mode analysis have been used to improve the metabolic efficiency of E. coli so that larger quantities of isobutanol may be produced.[10] E. coli is an ideal isobutanol bio-synthesizer for several reasons:

  • E. coli is an organism for which several tools of genetic manipulation exist, and it is an organism for which an extensive body of scientific literature exists.[5] This wealth of knowledge allows E. coli to be easily modified by scientists.
  • E. coli has the capacity to use lignocellulose (waste plant matter leftover from agriculture) in the synthesis of isobutanol. The use of lignocellulose prevents E. coli from using plant matter meant for human consumption, and prevents any food-fuel price relationship which would occur from the biosynthesis of isobutanol by E. coli.[5]
  • Genetic modification has been used to broaden the scope of lignocellulose which can be used by E. coli. This has made E. coli a useful and diverse isobutanol bio-synthesizer.[11]

The primary drawback of E. coli is that it is susceptible to bacteriophages when being grown. This susceptibility could potentially shut down entire bioreactors.[5]

Bacillus subtilis[edit]

Bacillus subtilis is a gram-positive rod-shaped bacteria. Bacillus subtilis offers many of the same advantages and disadvantages of E. coli, but it is less prominently used and does not produce isobutanol in quantities as large as E. coli.[5] Similar to E. coli, Bacillus subtilis is capable of producing isobutanol from lignocellulose, and is easily manipulated by common genetic techniques.[5] Elementary mode analysis has also been used to improve the isobutanol-synthesis metabolic pathway used by Bacillus subtilis, leading to higher yields of isobutanol being produced.[12]

Saccharomyces cerevisiae[edit]

Saccharomyces cerevisiae, or S. cerevisiae is a species of yeast. S. cerevisiae naturally produces isobutanol in small quantities via its valine biosynthetic pathway.[13] S. cerevisiae is an ideal candidate for isobutanol biofuel production for several reasons:

  • S. cerevisiae can be grown at low pH levels, helping prevent contamination during growth in industrial bioreactors.[5]
  • S. cerevisiae cannot be affected by bacteriophages because it is a eukaryote.[5]
  • Extensive scientific knowledge about S. cerevisiae and its biology already exists.[5]

Overexpression of the enzymes in the valine biosynthetic pathway of S. cerevisiae has been used to improve isobutanol yields.[13][14][15] S. cerevisiae, however, has proved difficult to work with because of its inherent biology:

  • As a eukaryote, S. cerevisiaeis genetically more complex than E. coli or B. subtilis, and is harder to genetically manipulate as a result.[5]
  • S. cerevisiae has the natural ability to produce ethanol. This natural ability can "overpower" and consequently inhibit isobutanol production by S. cerevisiae.[5]
  • S. cerevisiae cannot use five carbon sugars to produce isobutanol. The inability to use five-carbon sugars restricts S. cerevisiae from using lignocellulose, and means S. cerevisiae must use plant matter intended for human consumption to produce isobutanol. This results in an unfavorable food/fuel price relationship when isobutanol is produced by S. cerevisiae.[5]

Ralstonia eutropha[edit]

Ralstonia eutropha is a gram-negative soil bacterium of the betaproteobacteria class. Ralstonia eutropha is capable of converting electrical energy into isobutanol. This conversion is completed in several steps:

  • Anodes are placed in a mixture of H2O and CO2.
  • An electrical current is run through the anodes, and through an electrochemical process H2O and CO2 are combined to synthesize formic acid.
  • A culture of Ralstonia eutropha (composed of a strain tolerant to electricity) is kept within the H2O and CO2 mixture.
  • The culture of Ralstonia eutropha then converts formic acid from the mixture into isobutanol.
  • The biosynthesized isobutanol is then separated from the mixture, and can be used as a biofuel.

This method of isobutanol production offers a way to chemically store energy produced from sustainable sources.[16]

Applications[edit]

Isobutanol has a variety of technical and industrial applications:

  • feedstock in the manufacture of isobutyl acetate, which is used in the production of lacquer and similar coatings, and in the food industry as a flavoring agent
  • precursor of derivative esters - isobutyl esters such as diisobutyl phthalate (DIBP) are used as plasticizers in plastics, rubbers, and other dispersions
  • precursor of p-xylene, a building block for plastic bottles, textiles and clothing.
  • paint solvent
  • varnish remover
  • ink ingredient
  • paint additive, to reduce viscosity, improve brush flow, and retard formation of oil residues (blush) on painted surfaces
  • gasoline additive, to reduce carburetor icing
  • automotive polish additive
  • automotive paint cleaner additive
  • chemical extractant in production of organic compounds
  • mobile phase in thin layer chromatography.
  • potential gasoline alternative

Second Generation Biofuel[edit]

Isobutanol can be used as a biofuel substitute for gasoline in the current petroleum infrastructure. Isobutanol has not yet been put into mainstream use as a biofuel and would serve as a replacement for ethanol. Ethanol is a first generation biofuel, and is used primarily as a gasoline additive in the petroleum infrastructure. Isobutanol is a second generation biofuel with several qualities that resolve issues presented by ethanol.[5]

Isobutanol's properties make it an attractive biofuel:[5]

  • does not readily absorb water from air, preventing the corrosion of engines and pipelines.[5]
  • can be mixed at any proportion with gasoline,[18] meaning the fuel can "drop into" the existing petroleum infrastructure as a replacement fuel or major additive.[5]
  • can be produced from plant matter not connected to food supplies, preventing a fuel-price/food-price relationship.[5][10][11][12]

Safety and regulation[edit]

Isobutanol is one of the least toxic of the butanols with an LD50 of 2460 mg/kg (rat, oral).

In March 2009, the Canadian government announced a ban on isobutanol use in cosmetics.[19]

See also[edit]

References[edit]

  1. ^ "Iso-butanol". ChemicalLand21. 
  2. ^ a b Isobutanol, International Chemical Safety Card 0113, Geneva: International Programme on Chemical Safety, April 2005 .
  3. ^ Hahn, Heinz-Dieter; Dämbkes, Georg; Rupprich, Norbert (2005), "Butanols", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a04_463 .
  4. ^ Atsumi, Shota; Hanai, Taizo; Liao, James C. (3). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature 451 (7174): 86–89. doi:10.1038/nature06450. PMID 18172501. 
  5. ^ a b c d e f g h i j k l m n o p q r s t u Peralta-Yahya, Pamela P.; Zhang, Fuzhong; del Cardayre, Stephen B.; Keasling, Jay D. (15 August 2012). "Microbial engineering for the production of advanced biofuels". Nature 488 (7411): 320–328. doi:10.1038/nature11478. 
  6. ^ "Cyanobacteria". Retrieved 16 March 2013. 
  7. ^ a b c d Machado, Iara M.P.; Atsumi, Shota (1 November 2012). "Cyanobacterial biofuel production". Journal of Biotechnology 162 (1): 50–56. doi:10.1016/j.jbiotec.2012.03.005. 
  8. ^ a b c d Varman, A. M.; Xiao, Y.; Pakrasi, H. B.; Tang, Y. J. (26 November 2012). "Metabolic Engineering of Synechocystis sp. Strain PCC 6803 for Isobutanol Production". Applied and Environmental Microbiology 79 (3): 908–914. doi:10.1128/AEM.02827-12. 
  9. ^ a b Singh, Nirbhay Kumar; Dhar, Dolly Wattal (11 March 2011). "Microalgae as second generation biofuel. A review". Agronomy for Sustainable Development 31 (4): 605–629. doi:10.1007/s13593-011-0018-0. 
  10. ^ a b Trinh, Cong T. (9 June 2012). "Elucidating and reprogramming Escherichia coli metabolisms for obligate anaerobic n-butanol and isobutanol production". Applied Microbiology and Biotechnology 95 (4): 1083–1094. doi:10.1007/s00253-012-4197-7. 
  11. ^ a b Nakashima, Nobutaka; Tamura, Tomohiro (1 July 2012). "A new carbon catabolite repression mutation of Escherichia coli, mlc∗, and its use for producing isobutanol". Journal of Bioscience and Bioengineering 114 (1): 38–44. doi:10.1016/j.jbiosc.2012.02.029. 
  12. ^ a b Li, Shanshan; Huang, Di; Li, Yong; Wen, Jianping; Jia, Xiaoqiang (1 January 2012). "Rational improvement of the engineered isobutanol-producing Bacillus subtilis by elementary mode analysis". Microbial Cell Factories 11 (1): 101. doi:10.1186/1475-2859-11-101. 
  13. ^ a b Kondo, Takashi; Tezuka, Hironori; Ishii, Jun; Matsuda, Fumio; Ogino, Chiaki; Kondo, Akihiko (1 May 2012). "Genetic engineering to enhance the Ehrlich pathway and alter carbon flux for increased isobutanol production from glucose by Saccharomyces cerevisiae". Journal of Biotechnology 159 (1-2): 32–37. doi:10.1016/j.jbiotec.2012.01.022. 
  14. ^ MATSUDA, Fumio; KONDO, Takashi; IDA, Kengo; TEZUKA, Hironori; ISHII, Jun; KONDO, Akihiko (1 January 2012). "Construction of an Artificial Pathway for Isobutanol Biosynthesis in the Cytosol of Saccharomyces cerevisiae". Bioscience, Biotechnology, and Biochemistry 76 (11): 2139–2141. doi:10.1271/bbb.120420. 
  15. ^ Lee, Won-Heong; Seo, Seung-Oh; Bae, Yi-Hyun; Nan, Hong; Jin, Yong-Su; Seo, Jin-Ho (28 April 2012). "Isobutanol production in engineered Saccharomyces cerevisiae by overexpression of 2-ketoisovalerate decarboxylase and valine biosynthetic enzymes". Bioprocess and Biosystems Engineering 35 (9): 1467–1475. doi:10.1007/s00449-012-0736-y. 
  16. ^ Li, H.; Opgenorth, P. H.; Wernick, D. G.; Rogers, S.; Wu, T.-Y.; Higashide, W.; Malati, P.; Huo, Y.-X.; Cho, K. M.; Liao, J. C. (29 March 2012). "Integrated Electromicrobial Conversion of CO2 to Higher Alcohols". Science 335 (6076): 1596–1596. doi:10.1126/science.1217643. 
  17. ^ Lu, Jingnan; Brigham, Christopher J.; Gai, Claudia S.; Sinskey, Anthony J. (4 August 2012). "Studies on the production of branched-chain alcohols in engineered Ralstonia eutropha". Applied Microbiology and Biotechnology 96 (1): 283–297. doi:10.1007/s00253-012-4320-9. 
  18. ^ Ting, Cindy Ng Wei; Wu, Jinchuan; Takahashi, Katsuyuki; Endo, Ayako; Zhao, Hua (8 September 2012). "Screened Butanol-Tolerant Enterococcus faecium Capable of Butanol Production". Applied Biochemistry and Biotechnology 168 (6): 1672–1680. doi:10.1007/s12010-012-9888-0. 
  19. ^ "Cosmetic Chemicals Banned in Canada", Chem. Eng. News 87 (11), 2009-03-16: 38 .

External links[edit]