Commodity chemicals from renewable raw materials
The problem Many organic chemicals are being synthesized from nonrenewable petroleum and natural gas After use they end up as CO2 or remain in the environment Making future more sustainable = Finding ways to produce these chemicals from renewable sources Need to revisit old methods based on fermentation – with new advances they might be cheaper and more efficient, and greener What should be avoided: -carcinogens and toxic chemicals -energy-intensive processes (if alternatives are possible)
Commodities vs fine chemicals http://upload.wikimedia.org/wikipedia/commons/7/78/Fine_Chemicals,_Commodities_and_Specialties.jpg
Top largest-volume chemicals produced in the US from fossil fuels Ethylene Methanol Butadiene Ammonia Carbon dioxide Carbon black Propylene Xylene Isobutylene Methyl tert-butyl ether Formaldehyde Acrylonitrile Terephtalic acid Vinyl acetate Ethylene dichloride Ethylene oxyde Acetone Nitric acid Toluene Butyraldehyde Ammonium nitrate P-xylene Adipic acid Benzene Cumene Nitrobenzene Urea Ethylene glycol BPA Vinyl chloride Acetyc acid Ethylbenzene Phenol Styrene Propylene oxide
Olefins and chemicals derived from them: Dehydration of ethanol Reaction temperature ~450˚ Catalysts: SynDolTM (MgO-Al2O3/SiO2) Silicotungsten acid in MCM-411 zeolite Na2O-doped Mn2O3/Al2O3 and others.. (99% conversion) 1960 – first plant build by Solvay Group of Brazil – 20MT/day (6700MT/year) http://www.chematur.se/sok/download/Ethylene_rev_0904.pdf
Production of Ethylene From renewable sources Low density polyethylene Ni Cr /phosphine W/Mo catalyst Propylene Also from: Isopropyl alcohol Carbohydrate hydrolysis Ethylene+CO Propionic acid Cu/zeolite Styrene (vinyl benzene)
Other compounds prepared from ethylene and propylene
Alcohols and carboxylic acids 1,3 – propanediol from glucose/glycerol (biocatalysis) Poly(trimethylene terephthalate), Sorona ™ by DuPont
Alcohols and carboxylic acids 2. Ethylene, propylene, and butadiene glycols from sorbitol Other catalyst Ru/Sn with NaOH (94% conversion)
Alcohols and carboxylic acids 3. Ethyl acetate by dehydrogenation of ethanol Less cost effective compare to esterification Conditions: high temperature (but below 250˚C) and Cu catalyst Use: Solvent and diluent low cost low toxicity agreeable odor - circuit boards cleaners - some nail varnish removers - decaffeination of coffee beans and tea leaves - an activator or hardener in paints Present in confectionery, perfumes, and fruits Chemistry laboratory: extractions and separations ZSM-5
Alcohols and carboxylic acids Succinic Acid, Succinic Anhydride, and Maleic Anhydride from anaerobic fermentation of carbohydrates - Precursor to some specialized polyesters A component of some alkyd resins Acidity regulator in food and beverage, and pharmaceutical industry Food additive and dietary supplement (biological metabolite, Krebs cycle) Phthalic Anhydrade synthesis
Alcohols and carboxylic acids 5. Adipic acid from glucose http://3.bp.blogspot.com/-2toYsqzEGS4/UDL4Xkol-hI/AAAAAAAAAAA/83K2zcwtDYY/s1600/Screen%2Bshot%2B2010-09-16%2Bat%2B10.27.10%2BPM.png
Short report topics for Wednesday Polymers from renewable raw materials (Please, choose one of the following): Products from polyols Furfural Polyesters Polyamides