n-Butanol

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n-Butanol

Systematic name[hide] Butan-1-ol[1] Other names[hide] Butalcohol Butanol 1-Butanol Butyl alcohol Butyl hydrate Butylic alcohol Butyralcohol Butyric alcohol Butyryl alcohol Hydroxybutane Propylcarbinol Identifiers 71-36-3 263 258 8PJ61P6TS3 200-751-6 1120 DB02145 D03200 1-Butanol CHEBI:28885 CHEMBL14245 EO1400000 969148 25753 B00907 Image 1 SMILES

CAS number PubChem ChemSpider UNII EC number UN number DrugBank KEGG MeSH ChEBI ChEMBL RTECS number Beilstein Reference Gmelin Reference 3DMet Jmol-3D images

[show] InChI [show]

Properties Molecular formula C4H10O Molar mass 74.12 g mol1 Exact mass 74.073164942 g mol-1 Appearance Colourless liquid Density 0.81 g cm-3 Melting point 90 C, 183 K, -130 F Boiling point 118 C, 391 K, 244 F Solubility in water 63.2 g L-1 log P 0.839 Refractive index (nD) 1.399 (20 C) Viscosity 3 cP Dipole moment 1.66 D Thermochemistry Std enthalpy of 328(4) kJ mol-1 formation fHo298 Std enthalpy of 2670(20) kJ mol-1 combustion cHo298 Standard molar 225.7 JK1mol1 entropy So298 Hazards MSDS ICSC 0111 EU Index 603-004-00-6 EU classification
Xn

R-phrases S-phrases

R10, R22, R37/38, R41, R67 (S2), S7/9, S13, S26, S37/39, S46

NFPA 704

3 1 0
35 C 343 C 1.411.2% Related compounds Butanethiol n-Butylamine Pentane

Flash point Autoignition temperature Explosive limits

Related compounds

(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

n-Butanol or n-butyl alcohol or normal butanol is a primary alcohol with a 4-carbon structure and the molecular formula C4H9OH. Its isomers include isobutanol, 2-butanol, and tert-butanol. Butanol is one of the group of "fusel alcohols" (from the German for "bad liquor"), which have more than two carbon atoms and have significant solubility in water.

n-Butanol occurs naturally as a minor product of the fermentation of sugars and other carbohydrates,[2] and is present in many foods and beverages.[3][4] It is also a permitted artificial flavorant in the United States,[5] used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods and cordials.[6] It is also used in a wide range of consumer products.[3] The largest use of n-butanol is as an industrial intermediate, particularly for the manufacture of butyl acetate (itself an artificial flavorant and industrial solvent). It is a petrochemical, manufactured from propylene and usually used close to the point of manufacture. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 tonnes.[4]

[edit] Production
n-Butanol is produced industrially from the petrochemical feedstock propylene. Propylene is hydroformylated to butyraldehyde (oxo process) in the presence of a rhodium-based homogeneous catalyst similar to Wilkinson's catalyst. The butyraldehyde is then hydrogenated to produce n-butanol.[4]

[edit] Industrial use

n-butanol is an intermediate in the production of butyl acrylate, butyl acetate, dibutyl phthalate, dibutyl sebacate, and other butyl esters,[7][8] butyl ethers such as ethylene glycol monobutyl ether, di- and triethylene glycol monobutyl ether, and the corresponding butyl ether acetates. Other industrial uses include the manufacture of pharmaceuticals, polymers, pyroxylin plastics, herbicide esters (e.g., 2,4-D, 2,4,5-T)[9] and butyl xanthate. It is also used as a diluent/reactant in the manufacture of ureaformaldehyde and melamine formaldehyde resins.[4]

[edit] Other uses

n-Butanol is used as an ingredient in perfumes and as a solvent for the extraction of essential oils.[7] n-Butanol is also used as an extractant in the manufacture of antibiotics, hormones, and vitamins;[7][8] a solvent for paints, coatings, natural resins, gums, synthetic resins, dyes, alkaloids, and camphor.[7][8] Other miscellaneous applications of n-butanol are as a swelling agent in textiles, as a component of brake fluids, cleaning formulations, degreasers, and repellents;[3] and as a component of ore floation agents,[9] and of wood-treating systems.[10] n-Butanol has been proposed as a substitute for diesel fuel and gasoline. It is produced in small quantities in nearly all fermentations (see fusel oil), but species of Clostridium produce much higher yields of butanol, and research is currently underway to increase the ultimate yield of biobutanol from biomass. The production or, in some cases, use of the following substances may result in exposure to n-butanol: artificial leather, butyl esters, rubber cement, dyes, fruit essences, lacquers, motion picture, and photographic films, raincoats, perfumes, pyroxylin plastics, rayon, safety glass, shellac varnish, and waterproofed cloth.[3]

[edit] Occurrence in Nature

Alarm pheromones emitted by the Koschevnikov gland of honey bees contain n-butanol.

[edit] Occurrence in food

n-Butanol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer,[11] grape brandies,[12] wine,[13] and whisky.[14] It has been detected in the volatiles of hops,[15] jack fruit,[16] heat-treated milks,[17] musk melon,[18] cheese,[19] southern pea seed,[20] and cooked rice.[21] n-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.[22]

n-Butanol is used as an ingredient in processed and artificial flavourings,[7] and for the extraction lipid-free protein from egg yolk,[23] natural flavouring materials and vegetable oils, the manufacture of hop extract for beermaking, and as a solvent in removing pigments from moist curd leaf protein concentrate.[24]

[edit] Metabolism and toxicity

n-Butanol is readily absorbed through the intestinal tract and lungs, and also to some extent through the skin. [25] It is metabolized completely in vertebrates in a manner similar to ethanol: alcohol dehydrogenase coverts nbutanol to butyraldehyde; this is then converted to butyric acid by aldehyde dehydrogenase. Butyric acid can be fully metabolized to carbon dioxide and water by the -oxidation pathway, of which it is naturally the penultimate step. In the rat, only 0.03% of an oral dose of 2000 mg/kg was excreted in the urine.[26] The acute toxicity of n-butanol is relatively low, with oral LD50 values of 22904360 mg/kg (rat; comparable values for ethanol are 700015000 mg/kg).[4][27] No deaths were reported at an inhaled concentration of 8000 ppm (4-hour exposure, rats). At sub-lethal doses, n-butanol acts as a depressant of the central nervous system, similar to ethanol: one study in rats indicated that the intoxicating potency of n-butanol is some six times higher than that of ethanol, possibly because of its slower transformation by alcohol dehydrogenase.[28] n-Butanol is a natural component of many alcoholic beverages, albeit in low (but variable) concentrations.[29][30] It (along with similar fusel alcohols) is reputed to be responsible for severe "hangovers", although experiments in animal models show no evidence for this.[31] n-Butanol has occasionally been abused by alcoholics, leading to a range of adverse health effects.[32][33]

[edit] Other hazards

Liquid n-butanol, as is common with most organic solvents, is extremely irritating to the eyes; repeated contact with the skin can also cause irritation.[4] This is believed to be a generic effect of "defatting". No skin sensitization has been observed. Irritation of the respiratory pathways occurs only at very high concentrations (>2400 ppm).[34] With a flash point of 29 C (84 F), n-butanol presents a moderate fire hazard: it is slightly more flammable than kerosene or diesel fuel but less flammable than many other common organic solvents. The depressant effect on the central nervous system (similar to ethanol intoxication) is a potential hazard when working with n-butanol in enclosed spaces, although the odour threshold (0.230 ppm) is far below the concentration which would have any neurological effect.[34][35] n-Butanol is of low toxicity to aquatic vertebrates and invertebrates. It is rapidly biodegraded in water, although an estimated 83% partitions to air where it is degraded by hydroxyl radicals with a half-life of 1.2 2.3 days. It has low potential to bioaccumulate.[4] A potential hazard of significant discharges to watercourses is the rise in chemical oxygen demand (C.O.D.) associated with its biodegradation.

http://chemicalland21.com/petrochemical/n-butanol.htm

PRODUCT IDENTIFICATION CAS NO. 71-36-3 EINECS NO. 200-751-6 FORMULA CH3(CH2)3OH MOL WT. 74.12 H.S. CODE 2905.13 TOXICITY Oral rat LD50: 2460 mg/kg SYNONYMS n-butyl alcohol; 1-Butyl alcohol; Butanolen; Butanol; Butan-1-ol; 1-Butan-1-ol; Butyl hydroxide; 1-Hydroxybutane; Methylolpropane; Propylcarbinol; Propylmethanol; Butylowy alkohol; Butyric alcohol; Propylmethanol; Nomal Butanol; DERIVATION CLASSIFICATION PHYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE clear liquid MELTING POINT -89 C BOILING POINT 117 - 118 C SPECIFIC GRAVITY 0.810 - 0.812 SOLUBILITY IN WATER 9ml/100ml pH VAPOR DENSITY 2.6 AUTOIGNITION 343 C NFPA RATINGS Health: 1; Flammability: 3; Reactivity: 0 REFRACTIVE INDEX FLASH POINT 26 - 29 C STABILITY Stable under ordinary conditions GENERAL DESCRIPTION & APPLICATIONS 1-Butanol, a four carbon straight chain alcohol, is a volatile, clear liquid with a strong alcoholic odor; boils at 118 C, miscible with water. It is a highly refractive compound which corrodes some plastics, and rubbers. It is miscible with many organic solvents, and incompatible with strong oxidizers. It is flammable strongly with a luminous flame. It is used as a direct solvent and as an intermediate in the manufacture of other organic chemicals (e.g. Butyl acrylate and methacrylate, glycol ethers, butyl acetate, direct solvent use, plasticizers, amino resins, miscellaneous, including butylamines). Butanol and its derivatives continue to benefit from the long-term growth of water-based coatings formulations of all kinds. Analysts estimate that nearly 70 percent of all exterior architectural paints and as much as 85 percent of interior paints are now water-based. For butanol, butyl acrylate and butyl acetate, become increasingly important. Uses include :

Solvent for paints, coatings, varnishes, resins, gums, dyes, camphor, vegetable oils, dyes, fats, waxes, resins, shellac, rubbers, and alkaloids. Solvent in the purification of polyolefins, Alkyd resin coatings Intermediate in manufacturing other chemicals, esters of herbicides pharmaceuticals, veterinary medicine Swelling agent in textiles Manufacturing safety glass, hydraulic fluids, and detergent formulations. Formulating brake fluids. Extractant in manufacturing antibiotics, vitamins, and hormones Manufacturing garments from polyvinyl butyral-coated fabric, Cement additive to increase the fineness Ore floatation agents.

Melamine formaldehyde resins. SALES SPECIFICATION APPEARANCE clear liquid PURITY 99.5% min COLOR 10 max, APHA WATER 0.05% max SPECIFIC GRAVITY 0.810 - 0.812 ACIDITY 0.002 max ( KOH mg/kg) ALDEHYDES 0.05% max SULFURIC COLOR 15 max, APHA PRECAUTION IN HANDLING Protect against physical damage. Store in a cool, dry well-ventilated location, away from any area where the fire hazard may be acute. Outside or detached storage is preferred. Separate from incompatibles. Containers should be bonded and grounded for transfers to avoid static sparks. Storage and use areas should be No Smoking areas. Use non-sparking type tools and equipment, including explosion proof ventilation. Containers of this material may be hazardous when empty since they retain product residues (vapors, liquid); observe all warnings and precautions listed for the product. TRANSPORTATION PACKING 160kgs in drum, in bulk HAZARD CLASS 3 (Packing Group: III) UN NO. 1120 OTHER INFORMATION Hazard Symbols: XN F, Risk Phrases: 10-20, Safety Phrases: 7/9-9-13-16-26-33-37/39-46 PHYSICAL PROPERTIES OF SOLVENTS

Polarity Polar Non-polar Solvent Acetic Acid Acetic Anhydride Acetone Acetonitrile Ammonia solution Benzene Benzonitrile 1-Butanol 2-Butanol Butyl Acetate tert-Butyl Alcohol tert-Butyl Methyl Ether Carbon Disulfide Carbon Tetrachloride Chlorobenzene 1-Chlorobutane Chloroform Cyclohexane

Group

Formula

Water H-OH Carboxylic Acids R-COOH Amides R-CONH2 Alcohols R-OH Amines R-NH2 Ketones (Aldehydes) R-CO-R' Esters R-COOR' Alkyl Halides R-X Ethers R-O-R' Aromatics Ar-H Alkanes R-H Boiling Melting CAS RN Formula M.W. Point Point Density (C) (C) 64-19-7 C2H4O2 60.05 118 16.6 1.049 102.0 138108-24-7 C4H6O3 -73.1 1.08 9 140 67-64-1 C3H6O 58.08 56.2 -94.3 0.786 75-05-8 C2H3N 41.05 81.6 -46 0.786 7664-41-7 H3N 17.03 71-43-2 C6H6 78.11 80.1 5.5 0.879 103.1 100-47-0 C7H5N 191 -13 1.01 2 71-36-3 C4H10O 74.12 117.6 -89.5 0.81 78-92-2 C4H10O 74.12 98 -115 0.808 116.1 124123-86-4 C6H12O2 -106 0.882 6 126 75-65-0 C4H10O 74.12 82.2 25.5 0.786 1634-04-4 C5H12O 88.15 55.2 -109 0.741 75-15-0 CS2 76.13 46 -110 1.2632 153.8 56-23-5 CCl4 76.7 -22.4 1.594 2 112.5 108-90-7 C6H5Cl 131.7 -45.6 1.1066 6 109-69-3 C4H9Cl 92.57 77-78 -123.1 0.886 119.3 67-66-3 CHCl3 61.7 -63.7 1.498 8 110-82-7 C6H12 84.16 80.7 6.6 0.779

Solubility in Flash Dielectric water Point Constant (g/100g) (C) Miscible 6.15 39 12 Miscible Miscible 0.18 Insoluble 6.3 15 0.68 Miscible 5.1 0.1185 0.08 0.05 0.07 0.795 <0.1 20.7(25) 37.5 22.4 2.28 54 -18 6 -11 71

17.8 35 15.8(25) 26 12.5 2.24 2.71 4.81 2.02 22 11 -28 -30 29 -6 -20

Deuterium oxide 1,2-Dichlorobenzene 1,2-Dichloroethane Diethyl Amine Diethyl Ether Diethyl Ketone Diethylene Glycol Dimethyl Ether Diethylene Glycol Dimethyl Sulfoxide N,N-Dimethylacetamide Dimethylether N,N-Dimethylformamide 1,4-Dioxane Ethanol 2-Ethoxyethyl Ether Ethyl Acetate Ethylene Glycol Dimethyl Ether Ethylene Glycol Formic Acid Glycerin

7789-20-0 D2O 95-50-1 107-06-2 109-89-7 60-29-7 96-22-0 111-96-6 111-46-6 67-68-5 127-19-5 115-10-6 68-12-2 123-91-1 64-17-5 112-36-7 141-78-6 110-71-4 107-21-1 64-18-6 56-81-5 C6H4Cl2 C2H4Cl2 C4H11N C4H10O C5H10O C6H14O3 C4H10O3 C2H6OS C4H9NO C2H6O C3H7NO C4H8O2 C2H6O C8H18O3 C4H8O2 C4H10O2 C2H6O2 CH2O2 C3H8O3

20.03 147.0 0 98.96 73.14 74.12 86.13 134.1 7 106.1 2 78.13 87.12 46.07 73.09 88.11 46.07 162.2 3 88.11

101.3 4 180 83.5 55.5 34.6 102 162 245 189 166 -22 153 101.1 78.5 180190 77 -15 -35.3 -50 -116.3 -39 -68 -10 18.4 -20 -138.5 -61 11.8 -114.1 -44 -83.6 -58 -13 8.3 17.8 -90.6

1.107 1.306 1.245 0.7074 0.713 0.814 0.943 1.118 1.092 0.937 0.944 1.033 0.789 0.909 0.895 0.868 1.115 1.21 1.261 0.684 1.03 0.898 0.659 0.809 0.802 0.785 0.791 0.965 1.009

Miscible Insoluble 0.861 Miscible 7.5 4.70 Miscible 10 25.3 Miscible Miscible Miscible Miscible 10 8.7 Miscible Miscible Miscible Miscible 0.01 Miscible Miscible 0.014 54 9.5 Miscible Miscible Miscible Miscible

9.93(25) 67 10.42 3.6 4.34 7.23 31.7 47 37.80 36.7 2.21(25) 24.6 6(25) 7.2 37.7 58.5 42.5 1.92 31.3 1.89 15.8(25) 18.3(25) 32.6(25) 16.90 13 -39 -45 13 67 143 95 66 -41 58 12 13 82 -4 -6 111 160 -4 105 26 -22 43 28 12 12 38 44

90.12 85 195 100 290 98

62.07 46.03 92.09 100.2 heptane 142-82-5 C7H16 0 179.2 Hexamethylphosphor amide 680-31-9 C6H18N3OP 0 Hexamethylphosphorous 163.2 1608-26-0 C6H18N3P triamide 0 Hexane 110-54-3 C6H14 86.18 Isoamyl alcohol 123-51-3 C5H12O 88.15 Isobutyl alcohol 78-83-1 78-83-1 74.12 Isopropanol 67-63-0 C3H8O 88.15 Methanol 67-56-1 CH4O 32.04 2-Methoxyethanol 2-Methoxyethyl Acetate 109-86-4 110-49-6 C3H8O2 C5H10O3

232.5 7.2 150 -44 -95 -117 -108 -88.5 -98 -85.1 -65

69 130 108 82.4 64.6 12476.10 125 118.1 145

Methyl Ethyl Ketone Methyl Isobutyl Ketone 1-Methyl-2-pyrrolidinone Methylene Chloride Nitromethane 1-Octanol Pentane Petroleum ether Propanoic acid 1-Propanol Propylene carbonate Pyridine Tetrachloroethylene Tetrahydrofuran Toluene 1,1,2Trichlorotrifluoroethane Triethyl amine 2,2,2-Trifluoroethanol Water m-Xylene o-Xylene p-Xylene

78-93-3 108-10-1 872-50-4 75-09-2 75-52-5 111-87-5

C4H8O C6H12O CH5H9NO CH2Cl2 CH3NO2 C8H18O

109-66-0 C5H12 8032-32-4 79-09-4 C3H6O2 71-23-8 C3H8O 108-32-7 110-86-1 127-18-4 109-99-9 108-88-3 76-13-1 121-44-8 75-89-8 C4H6O3 C5H5N C2Cl4 C4H8O C7H8 C2Cl3F3 C6H15N C2H3F3O

3 72.11 100.1 6 99.13 84.93 61.04 130.2 3 72.15 74.08 88.15 102.0 9 79.10 165.8 3 72.11 92.14 187.3 8 101.1 9 100.0 4 18.02

79.6 117118 202 39.8 101.2 196 36.1 30-60 141 97 240

-86.3 -80 -24 -96.7 -29 -15 -129.7 -40 -21.5 -126 -55

0.805 0.7978 1.033 1.326 1.382 0.826 0.626 0.656 0.993 0.803 1.21 0.982 1.623

25.6 1.9 10 1.32 9.50 Insoluble 0.04 -

18.5 32 9.08 35.9 1.84 3.4 20.1(25)

-7 14 91 1.6 35 81 -49 -30 51 15

115.2 -41.6 121 -22

37 Miscible Moderately 132 Soluble Miscible 12.3(25) 17 0.015 30 0.05 0.02 0.02 Insoluble Insoluble Insoluble 2.4 26.5 78.54 2.37 2.57 2.27 -

66 -108.4 0.886 110.6 -93 0.867 47-48 -36 88.9 74.1 1.575

7.6 -21 2.38(25) 4 -11 29 27 32 27

-114.7 0.728 -45 1.393 0.998 0.868 0.897 0.861

7732-18-5 H2O 108-38-3 95-47-6 106-42-3 C8H10 C8H10 C8H10

100.0 0.00 0

106.1 139.1 -47.8 7 106.1 144 -25.2 7 106.1 138.4 13.3 7

http://www.dow.com/productsafety/finder/nbut.htm

Product Safety Assessment (PSA): n-Butanol

Printer-friendly version of this PSA (61KB PDF)

Select a Topic:
Names Product Overview Manufacture of Product Product Description Product Uses Exposure Potential Health Information Environmental Information Physical Hazard Information Regulatory Information Additional Information References Names

CAS No. 71-36-3 n-Butanol Normal butanol Butyl hydroxide 1-Hydroxybutane

Butanol n-Butyl alcohol Propyl carbinol Propylmethanol 1-Butanol

Butyl alcohol Butyric alcohol Propylcarbinol Methylolpropane

back to top Product Overview

n-Butanol (normal butanol) is a clear, colorless liquid that is flammable. It has a characteristic bananalike odor1and is used to produce other chemicals, as an ingredient in formulated products such as cosmetics, and as a solvent.2 See Product Uses and Physical Hazard Information. n-Butanol demonstrates an overall low order of toxicity.3 Acute (24 hours or less in duration) overexposures may cause irritation to the eyes and skin or can be harmful if inhaled. Prolonged (greater than 24 hours), excessive exposure to vapors may cause serious adverse effects, and even death. Birth defects have been observed in animals exposed to high concentrations of n-butanol which also caused serious adverse effects to the exposed mothers.4 See Health Information. Occupational and consumer exposure is dependent upon the conditions under which n-butanol or the end-product is used. See Exposure Potential. n-Butanol is practically non-toxic to aquatic organisms and birds on an acute basis. The material is readily biodegradable.5 See Environmental Information.

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Manufacture of Product6

Capacity Dow7 produces only the isomer n-butanol at two plants in the U.S. and purchases n-butanol from one of its joint ventures in Malaysia. Dow produces 9% of the worlds capacity of plasticizer alcohols, such as n-butanol. Global consumption of n-butanol in 2002 was 10 billion pounds (5.1 million metric tons). Process Dow first generates n-butyraldehyde using propylene, carbon monoxide (CO) and hydrogen gas (H2). By using low-pressure technology and a triphenylphosphine rhodium hydrocarbonyl catalyst, approximately eight to ten times more n-butyraldehyde is produced than isobutyraldehyde. The nbutyraldehyde is then reacted with H2 to form n-butanol. Isobutanol is a byproduct of n-butanol production in Dows process.

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Product Description
n-Butanol is a colorless, neutral liquid of medium volatility with a characteristic banana-like odor. It has restricted miscibility (about 7-8%) in water, but is freely miscible with all common solvents such as glycols, ketones, alcohol, aldehydes, ethers, and aromatic and aliphatic hydrocarbons.8 back to top

Product Uses

Market literature classifies n-butanol as both an oxo-chemical derivative and a plasticizer alcohol for market purposes. The uses of n-butanol vary by geographic area, but in general it is used to make other chemicals, or used as a solvent or an ingredient in formulated products such as cosmetics. A partial list of chemicals in which it is used includes:9

Acrylate/methacrylate esters Glycol ethers n-Butyl acetate Amino resins

n-Butylamines

Applications, chemicals and products that use n-butanol include: 10,11

Solvents for paints, coatings, varnishes, resins, gums, dyes, camphor, vegetable oils, fats, waxes, resins, shellac, rubbers and alkaloids Plasticizers to improve how a plastic material processes Coatings as a solvent for a variety of applications, such as curable lacquers and cross-linked baking finishes Chemical intermediate or raw material for producing many other chemicals and plastics, including safety glass, hydraulic fluids and detergent formulations Textiles as a swelling agent and manufacturing garments from coated fabric Flotation agents Cleaners Floor polishes Cosmetics including eye makeup, foundations, lipsticks, nail care products, personal hygiene products and shaving products Drugs and antibiotics, hormones, and vitamins Gasoline (as an additive) and brake fluid (formulation component)

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Exposure Potential
n-Butanol is used in the production of consumer products such as cosmetic nail products, but is not sold directly for consumer use. Based on the uses for n-butanol, the public could be exposed through:

Workplace exposure Exposure can occur either in an n-butanol manufacturing facility or in the various industrial and consumer services facilities that use n-butanol. n-Butanol should be handled in a well-ventilated area or in completely closed systems. Each manufacturing, industrial and service facility should have appropriate work process and safety equipment policies in place to limit n-butanol exposure. Good industrial hygiene practices minimize the risk of exposure. Consumer exposure to products containing n-butanol Although Dow does not sell n-butanol for consumer use, it is used as a component in some formulated consumer products such as cosmetics. n-Butanol is considered safe as a cosmetic ingredient by the Cosmetic Ingredient Review Expert Panel.12,13 n-Butanol demonstrates an overall low order of human toxicity.14 See Health Information. Environmental releases In the event of a spill, the focus is on containing the spill to prevent contamination of soil, surface or ground water. If n-butanol does reach soil and water nearby, it can pose a flammability concern. All ignition sources should be removed from the area, proper grounding and bonding techniques used, and proper protective equipment worn. n-Butanol is readily biodegradable in water and readily decomposed in the air by photodegradation. It has a low order of toxicity to environmental organisms at all levels of the food chain.15 See Environmental, Health and Physical Hazard Information. Large release Industrial spills or releases are infrequent and are generally contained. If a large spill does occur, the material should be captured, collected and re-processed, or disposed of according to applicable governmental requirements. Emergency personnel should wear proper protective equipment and follow emergency procedures carefully. Flammability is the primary concern. All ignition sources should be removed from the area, proper grounding and bonding techniques used and flammability concerns communicated to the community, when appropriate. See Environmental, Health and Physical Hazard Information.

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Health Information

n-Butanol shows a low order of toxicity in single-dose exposures to laboratory animals.16 For safety, however, avoid contact with eyes, skin and clothing. Avoid breathing vapor. Do not swallow. Use only with adequate ventilation, keep containers closed and wash thoroughly after using.17 Prolonged excessive exposure may cause serious adverse effects, and even death. To identify acceptable exposure limits and proper protective equipment, please consult the Safety Data Sheet (SDS). Exposure may cause severe eye irritation and moderate skin irritation. Repeated skin contact may aggravate preexisting dermatitis and result in absorption of harmful amounts through the skin.18 In most cases, n-butanol is quickly metabolized to carbon dioxide (CO2).19 Short-term exposure (acute) or repeated overexposure to n-butanol can result in depression of the central nervous system, as is often observed with other short-chain aliphatic alcohols. This effect is usually transient (goes away after the exposure is removed and the body recovers/metabolizes the material).20 According to the European Centre for Ecotoxicology and Toxicology of Chemicals (ECETOC), there is no evidence that n-butanol exhibits genotoxicity (causes damage to the DNA or cancer). There is a report of fetotoxicity (birth defects or malformations) in rats when the exposures are great enough to cause significant toxicity to the mother. 21,22 In a rat study without detailed information, n-butanol has caused birth defects at doses reported to be nontoxic to the mother.23 The dose levels producing these effects in both studies were many times higher than any dose levels expected from exposure due to use of n-butanol. In fact, a newer study utilizing current protocols has shown no evidence of fetotoxicity at high levels that are toxic to the mother.24 For more information on the health hazards of n-butanol and recommended protective equipment, view the SDS. back to top

Environmental Information
n-Butanol is considered a volatile organic compound (VOC) and is emitted by natural sources such as plants (rape, rye and grass), trees (beech, birch and hornbeam), animal waste, microbes and insects. n-Butanol enters the environment from either natural sources or, to a small extent, during its production, transport, storage and use as a chemical intermediate and a solvent. The primary route for entering the environment is the release to the atmosphere when used as a solvent. n-Butanol is readily degradable in water and readily decomposed in the air by photodegradation. It does adsorb on soil, and favors partitioning to water versus air (80% to 15-20%). Because the degradation and decomposition is rapid, bioaccumulation or bioconcentration is unlikely.25 n-Butanol is practically non-toxic to aquatic organisms and birds on an acute basis.26 back to top

Physical Hazard Information27

n-Butanol has a flash point of 35C (95F) and as such is considered a flammable liquid. When mixed with air at room temperature, n-butanol can form a flammable mixture. Every precaution should be taken to prevent exposure to ignition sources, including:

Keep containers closed. Proper grounding and bonding procedures should be followed to minimize the risk of ignition through static build up, heat, sparks or flame. Never use air pressure for transferring the product.

Vapors are heavier than air and may travel a long distance and accumulate in low lying areas. Ignition and/or flash back may occur. Ventilation can control airborne levels to minimize exposure and flammability risks. Violent steam generation or eruption may occur when applying a direct water stream to hot liquids. Containers, even those that are empty, can contain vapors. Do not cut, drill, grind, weld, or perform similar operations on or near empty containers.

n-Butanol is thermally stable at typical use temperatures, but elevated temperatures can lead to decomposition. Avoid contact with halogens, strong acids and strong oxidizers. Additional physical property information for n-butanol is available on the Safety Data Sheet. back to top

Regulatory Information
Regulations may exist that govern the manufacture, sale, transportation, use and/or disposal of n-Butanol. These regulations may vary by city, state, country or geographic region. Information may be found by consulting the relevant Safety Data Sheet or Contact Us. back to top Additional Information

Safety Data Sheet Dows Oxygenated Solvents web site Product Information Sheet

For more business information about n-butanol, visit Dows Oxygenated Solvents web site, listed above. Last Updated: May 2, 2006

http://en.wikipedia.org/wiki/Butanol_fuel

Butanol fuel
From Wikipedia, the free encyclopedia Jump to: navigation, search This article is about Butanol from biomass used as a fuel. For other alcohols used as fuels, see Alcohol fuel. Butanol may be used as a fuel in an internal combustion engine. Because its longer hydrocarbon chain causes it to be fairly non-polar, it is more similar to gasoline than it is to ethanol. Butanol has been demonstrated to work in vehicles designed for use with gasoline without modification.[1] It can be produced from biomass (as "biobutanol")[2] as well as fossil fuels (as "petrobutanol"); but biobutanol and petrobutanol have the same chemical properties.

Contents
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1 Production of biobutanol o 1.1 Technologies 1.1.1 Algae butanol o 1.2 Producers 2 Distribution 3 Properties of common fuels o 3.1 Energy content and effects on fuel economy o 3.2 Octane rating o 3.3 Air-fuel ratio o 3.4 Specific energy o 3.5 Viscosity o 3.6 Heat of vaporization 4 Potential problems with the use of butanol fuel 5 Possible butanol fuel mixtures 6 Current use of butanol in vehicles 7 Research 8 See also 9 References 10 External links

[edit] Production of biobutanol

Main article: Energy crop Butanol from biomass is called biobutanol.[3] It can be used in unmodified gasoline engines.[4]

[edit] Technologies
Biobutanol can be produced by fermentation of biomass by the A.B.E. process. The process uses the bacterium Clostridium acetobutylicum, also known as the Weizmann organism. It was Chaim Weizmann who first used

this bacterium for the production of acetone from starch (with the main use of acetone being the making of Cordite) in 1916. The butanol was a by-product of this fermentation (twice as much butanol was produced). The process also creates a recoverable amount of H2 and a number of other by-products: acetic, lactic and propionic acids, isopropanol and ethanol. The difference from ethanol production is primarily in the fermentation of the feedstock and minor changes in distillation. The feedstocks are the same as for ethanol: energy crops such as sugar beets, sugar cane, corn grain, wheat and cassava, prospective non-food energy crops such as switchgrass and even guayule in North America, as well as agricultural byproducts such as straw and corn stalks.[5] According to DuPont, existing bioethanol plants can cost-effectively be retrofitted to biobutanol production.[6] Additionally, butanol production from biomass and agricultural byproducts could be more efficient (i.e. unit engine motive power delivered per unit solar energy consumed) than ethanol or methanol production.[7]

[edit] Algae butanol

Main articles: Algae fuel and Diatom Biobutanol can be made entirely with solar energy, from algae (called Solalgal Fuel) or diatoms.[8]

[edit] Producers
DuPont and BP plan to make biobutanol the first product of their joint effort to develop, produce, and market next-generation biofuels[9]. In Europe the Swiss company Butalco[10] is developing genetically modified yeasts for the production of biobutanol from cellulosic materials. The number of biobutanol producers with commercial plants coming on line continues to grow monthly.[citation needed] At present, there are number of bioethanol plants, which are being converted to biobutanol plants, which should increase the number of butanol producers as they come on-line.[citation needed]

[edit] Distribution
Butanol better tolerates water contamination and is less corrosive than ethanol and more suitable for distribution through existing pipelines for gasoline.[6] In blends with diesel or gasoline, butanol is less likely to separate from this fuel than ethanol if the fuel is contaminated with water.[6] There is also a vapor pressure coblend synergy with butanol and gasoline containing ethanol, which facilitates ethanol blending. This facilitates storage and distribution of blended fuels.[6][11][12]

[edit] Properties of common fuels

[citation needed]

Energy density Gasoline and biogasoline 32 MJ/L Butanol fuel 29.2 MJ/L Ethanol fuel 19.6 MJ/L Methanol fuel 16 MJ/L Fuel

Air-fuel Specific ratio energy 14.6 2.9 MJ/kg air 11.1 3.2 MJ/kg air 9.0 3.0 MJ/kg air 6.4 3.1 MJ/kg air

Heat of RON MON vaporization 0.36 MJ/kg 9199 8189 0.43 MJ/kg 96 78 0.92 MJ/kg 107 89 1.2 MJ/kg 106 92

[edit] Energy content and effects on fuel economy

Switching a gasoline engine over to butanol would in theory result in a fuel consumption penalty of about 10%[14] but butanol's effect on mileage is yet to be determined by a scientific study. While the energy

density for any mixture of gasoline and butanol can be calculated, tests with other alcohol fuels have demonstrated that the effect on fuel economy is not proportional to the change in energy density.[15]

[edit] Octane rating

The octane rating of n-butanol is similar to that of gasoline but lower than that of ethanol and methanol. nButanol has a RON (Research Octane number) of 96 and a MON (Motor octane number) of 78 (with a resulting "(R+M)/2 pump octane number" of 87, as used in North America) while t-butanol has octane ratings of 105 RON and 89 MON.[16] t-Butanol is used as an additive in gasoline but cannot be used as a fuel in its pure form because its relatively high melting point of 25.5 C causes it to gel and freeze near room temperature. A fuel with a higher octane rating is less prone to knocking (extremely rapid and spontaneous combustion by compression) and the control system of any modern car engine can take advantage of this by adjusting the ignition timing. This will improve energy efficiency, leading to a better fuel economy than the comparisons of energy content different fuels indicate. By increasing the compression ratio, further gains in fuel economy, power and torque can be achieved. Conversely, a fuel with lower octane rating is more prone to knocking and will lower efficiency. Knocking can also cause engine damage.[17]

[edit] Air-fuel ratio

Alcohol fuels, including butanol and ethanol, are partially oxidized and therefore need to run at richer mixtures than gasoline. Standard gasoline engines in cars can adjust the air-fuel ratio to accommodate variations in the fuel, but only within certain limits depending on model. If the limit is exceeded by running the engine on pure butanol or a gasoline blend with a high percentage of butanol, the engine will run lean, something which can critically damage components. Compared to ethanol, butanol can be mixed in higher ratios with gasoline for use in existing cars without the need for retrofit as the air-fuel ratio and energy content are closer to that of gasoline.[11][12]

[edit] Specific energy

Alcohol fuels have less energy per unit weight and unit volume than gasoline. To make it possible to compare the net energy released per cycle a measure called the fuels specific energy is sometimes used. It is defined as the energy released per air fuel ratio. The net energy released per cycle is higher for butanol than ethanol or methanol and about 10% higher than for gasoline.[18] Kinematic Substance viscosity [edit] Viscosity at 20C 3.64 cSt The viscosity of alcohols increase with longer carbon chains. For this reason, butanol Butanol Ethanol 1.52 cSt is used as an alternative to shorter alcohols when a more viscous solvent is desired. The kinematic viscosity of butanol is several times higher than that of gasoline and Methanol 0.64 cSt about as viscous as high quality diesel fuel.[19] Gasoline 0.40.8 cSt Diesel >3 cSt [edit] Heat of vaporization Water 1.0 cSt The fuel in an engine has to be vaporized before it will burn. Insufficient vaporization is a known problem with alcohol fuels during cold starts in cold weather. As the heat of vaporization of butanol is less than half of that of ethanol, an engine running on butanol should be easier to start in cold weather than one running on ethanol or methanol.[11]

[edit] Potential problems with the use of butanol fuel

The potential problems with the use of butanol are similar to those of ethanol:

To match the combustion characteristics of gasoline, the utilization of butanol fuel as a substitute for gasoline requires fuel-flow increases (though butanol has only slightly less energy than gasoline, so the fuel-flow increase required is only minimal, maybe 10%, compared to 40% for ethanol.) Alcohol-based fuels are not compatible with some fuel system components. Alcohol fuels may cause erroneous gas gauge readings in vehicles with capacitance fuel level gauging. While ethanol and methanol have lower energy densities than butanol, their higher octane number allows for greater compression ratio and efficiency. Higher combustion engine efficiency allows for lesser greenhouse gas emissions per unit motive energy extracted. Butanol is toxic at a rate of 20g per liter and may need to undergo Tier 1 and Tier 2 health effects testing before being permitted as a primary fuel by the EPA.[20]

[edit] Possible butanol fuel mixtures

Standards for the blending of ethanol and methanol in gasoline exist in many countries, including the EU, the US and Brazil. Approximate equivalent butanol blends can be calculated from the relations between the stochiometric fuel-air ratio of butanol, ethanol and gasoline. Common ethanol fuel mixtures for fuel sold as gasoline currently range from 5% to 10%. The share of butanol can be 60% greater than the equivalent ethanol share, which gives a range from 8% to 16%. "Equivalent" in this case refers only to the vehicle's ability to adjust to the fuel. Other properties such as energy density, viscosity and heat of vaporization will vary and may further limit the percentage of butanol that can be blended with gasoline.[citation needed] Consumer acceptance may be limited due to the offensive smell of butanol.[citation needed] Plans are underway to market a fuel that is 85% Ethanol and 15% Butanol (E85B), so existing E85 internal combustion engines can run on a 100% renewable fuel that could be made without using any fossil fuels. Because its longer hydrocarbon chain causes it to be fairly non-polar, it is more similar to gasoline than it is to ethanol. Butanol has been demonstrated to work in vehicles designed for use with gasoline without modification.

[edit] Current use of butanol in vehicles

Currently no production vehicle is known to be approved by the manufacturer for use with 100% butanol. As of early 2009, only few vehicles are approved for even using E85 fuel (i.e. 85% ethanol + 15% gasoline)in the USA. However, in Brazil all vehicle manufacturers (Fiat, Ford, VW, GM, Toyota, Honda, Peugeot, Citroen and others) produce flex fuel vehicles that can run on 100% ethanol or any mix of ethanol and gasoline. These flex fuel cars represent 90% of the sales of personal vehicles in Brazil, in 2009. BP and Dupont, engaged in a joint venture to produce and promote butanol fuel, claim[21] that "biobutanol can be blended up to 10%v/v in European gasoline and 11.5%v/v in US gasoline". [22] David Ramey drove from Blacklick, Ohio to San Diego, California using 100% butanol in an unmodified 1992 Buick Park Avenue.[1][23] In the 2009 Petit Le Mans race, the No. 16 Lola B09/86 - Mazda MZR-R of Dyson Racing ran on a mixture of biobutanol and ethanol developed by team technology partner BP.

[edit] Research
The Swiss company Butalco GmbH uses a special technology to modify yeasts in order to produce butanol instead of ethanol. Yeasts as production organisms for butanol have decisive advantages compared to bacteria. [24] The company Gevo, Inc, in Englewood, Colorado, is developing a biotechnology process to mass-produce isobutanol from renewable resources.[25] Scientists at Tulane University have "found a way to convert newspaper and other plant based materials into car fuel[.]"[26] This study found a way to produce butanol directly from cellulose.