123-51-3 Usage
Chemical properties
Colorless to pale yellow clear oily liquid. Apple brandy aroma and spicy flavor. Melting point:-117.2 °C. Boiling point: 130 °C. Relative density (d2525): 0.813. Refractive index (nD20): 1.4075. Vapors are toxic. Miscible in ethanol and ether. Slightly soluble in water.
Natural products present in the form of esters in strawberries, peppermint, lemongrass, eucalyptus oil and rum and so on.
content analysis
determined through non-polar column method of gas chromatography(GT-10-4).
Toxicity? GRAS (FEMA).
Use limits
FEMA (mg/kg): soft drinks 17; cold drinks 7.6; candy 52; baked goods 24; pudding 46; gum 300; alcohol 100. Modest limit (FDA § 172.515, 2000).
Uses
Different sources of media describe the Uses of 123-51-3 differently. You can refer to the following data:
1. (1) Used as food flavors according to GB 2760-96. Mainly used for the preparation of apple and banana flavor.
(2) Used as chromatographic reagent and extractant, and also used in the pharmaceutical industry
(3) Used in the manufacture of spices, pharmaceuticals and mineral processing agents, and also used as solvents
(4) This goods have apple brandy aroma and spicy flavor. China's GB 2760-86 provides for its allowable use as food spices, mainly for the preparation of apple and banana flavor. Isoamyl alcohol and sodium nitrite can perform esterification to form isoamyl nitrite, which is the fastest nitrous esters short-acting vasodilator. Isoamyl alcohol can be used to synthesize sedatives and hypnotics, such as bromural and amytal. Isoamyl alcohol can also be used as solvents and the reagents for chemical analysis. It is also used as the raw materials to produce plasticizers and photographic pharmaceutical. In addition, it is one component of the fuel oil.
(5) Used for the manufacture of spices, pharmaceuticals and photographic drugs, and also used as solvents.
(6) Used as the solvents of fat, resin and alkaloid. Used for the determination of fat in milk and the determination of iron, silicon, thorium and fusel oil. Also used for the complexation extraction of iron, cobalt, copper salt and diphenylcarbazide. Used for the separation of lithium Chloride from other alkali metal chlorides.
2. 3-Methyl-1-butanol and 2-methyl-1-butanol are normally used as apple or banana flavoring agents for wine. They can also be used as chemical intermediates and solvents in pharmaceutical products.
3. Isoamylol is one of the several isomers of amyl alcohol and the main ingredient in the production of banana oil.
4. Solvent for fats, resins, alkaloids, etc.; manufacture of isoamyl (amyl) Compounds, isovaleric acid, mercury fulminate, pyroxylin, artificial silk, lacquers, smokeless powders; in microscopy; for dehydrating celloidin solutions; for determining fat in milk.
Production methods
(1) This product naturally presents in the form of esters in strawberries, peppermint, lemongrass, eucalyptus oil and rum and so on. It can be synthesized by acid method or the hydroformylation of C4 alkenes. 3-methyl-1-butanol (85% in the fusel oil) can be obtained by chemical treatment and distillation separation of the fusel oil that is the side products form the alcohol fermentation of starch and sugar.
(2) Derived from fusel oil fractionation.
Pentane performs chlorination and hydrolysis reaction to form mixed alcohol, and then isoamyl alcohol can be derived from the mixed alcohol.
Hazards & Safety Information
Category???? Flammable liquids
Toxic classification?? moderate toxic
Acute Toxicity?? Oral-rat LD50: 1300 mg/kg; celiac-mouse LD50: 233 mg/kg
Stimulation Data?? Skin-Rabbit 20mg/24hours Moderate; Eye-Rabbit 20mg/24hours Moderate
Explosives hazardous characteristics?? Mix with air to be explosive
Flammability hazard characteristics?? In case of fire, high temperature and oxidant flammable; combustion to release excitive smoke
Storage and transportation characteristics?? Ventilation; Low temperature; dry; Separate storage with oxidizing agent
Extinguishing agent? dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent
Occupational Standard? TLV-TWA 100 PPM (360 mg /m3); STEL 125 PPM (450 mg/m3)
Description
Isoamyl alcohol has a characteristic pungent odor and repulsive
taste. Industrially prepared by rectification of fusel oil.
Chemical Properties
Different sources of media describe the Chemical Properties of 123-51-3 differently. You can refer to the following data:
1. Isoamyl alcohol has a fusel oil, whiskey-characteristic, pungent odor and repulsive taste.
2. Amyl alcohols (pentanols) have eight isomers.
All are flammable, colorless liquids, except the isomer 2,2-
dimethyl-1-propanol, which is a crystalline solid.
3. colourless liquid
4. The air odor threshold for 3-methyl-1-butanol was reported
as 0.042 ppm , which provides some acute warning
for exposure to this chemical.
Physical properties
Clear, colorless liquid with a pungent odor. An odor threshold concentration of 1.7 ppbv was
reported by Nagata and Takeuchi (1990).
Occurrence
Constitutes the major portion of fusel oil; also known as fermentation of amyl alcohol; it has been identified
as an ester among the constituents of Roman chamomile oil; French peppermint, Java citronella, Réunion geranium, tea, Teucrium
chamaedrys, Eucalyptus amigdalina, Achillea ageratum and Artemisia camphorata. It is reported present in the aromas of strawberry and raspberry. It is also reported found in over 230 natural sources including apple, apricot, banana, sweet and sour cherry,
citrus peel oils and juices, berries, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, asparagus, cabbage, kohlrabi,
celery stalk and seed, leek, peas, potato, sauerkraut, tomato, ginger, mint oils, vinegar, mustard, bread, cheeses, butter, milk, fish，meats, cognac, rum, whiskies, cider, sherry, grape wines, tea, filberts, pecans, walnuts, oats, honey, soybean, avocado, Arctic
bramble, olive, passion fruit, rose and Malay apple, mushroom, mango, tamarind, pear brandy, port, cardamom, gin, quince,
radish, sukiyaki, sake, buckwheat, corn oil, sweet corn, laurel, malt, wort, cherimoya, loquat, Bourbon vanilla, shrimp, oysters,
crayfish, mussels and scallops
Definition
ChEBI: An alkyl alcohol that is butan-1-ol substituted by a methyl group at position 3.
Production Methods
3-Methyl-1-butanol is used as solvents
for oils, fats, resins, and waxes; in the plastics industry in
spinning polyacrylonitrile; and in manufacturing lacquers,
chemicals, and pharmaceuticals. It is also used as
flavoring agents and in fragrances. Industrial exposure
is principally by the dermal contact and inhalation.
Preparation
Different sources of media describe the Preparation of 123-51-3 differently. You can refer to the following data:
1. Industrially prepared by rectification of fusel oil.
2. 3-Methyl-1-butanol and 2-methyl-1-butanol were first isolated from fusel oils, by-products of ethanol fermentation by yeast. These compounds can also be derived from the chlorination of pentane followed by hydrolysis. Another alternative process is the oxo process, a general strategy for the manufacture of C4 and higher alcohols. Both the chlorination process and the oxo process are current commercial processes for the production of 3-methyl-1-butanol and 2-methyl-1-butanol, but the oxo process via the hydroformylation reaction is the more popular. Two main technologies are used for the process. The first was brought on stream by Ruhrchemie in Germany and Exxon in USA in the 1940s and is generally referred to as "high-pressure cobalt catalyst technology." The active catalyst species is cobalt hydrocarbonyl, and a pressure of 200–300 atm is required to maintain the stability of the catalyst. In the early 1960s, Shell commercialized a modern version of the cobalt catalyst process. This technology uses organophosphine ligands, which allows a lower operating pressure of 30–100 atm but at the expense of the catalyst activity. The Shell technology is employed primarily in the production of linear primary alcohols, whereas the high-pressure cobalt technology is frequently used in the production of branched alcohols.
Aroma threshold values
Detection: 250 ppb to 4.1 ppm
Taste threshold values
Taste characteristics at 50 ppm: fusel, fermented, fruity, banana, ethereal and cognac
General Description
Colorless liquid with a mild, choking alcohol odor. Less dense than water, soluble in water. Hence floats on water. Produces an irritating vapor.
Air & Water Reactions
Highly flammable. Water soluble.
Reactivity Profile
3-Methyl-1-butanol attacks plastics [Handling Chemicals Safely, 1980. p. 236]. Mixtures with concentrated sulfuric acid and strong hydrogen peroxide may cause explosions. Mixing with hypochlorous acid in water or water/carbon tetrachloride solution can generate isoamyl hypochlorites, which may explode, particularly on exposure to sunlight or heat. Mixing with chlorine would also yield isoamyl hypochlorites [NFPA 491 M, 1991]. Base-catalysed reactions with isocyanates can occur with explosive violence [Wischmeyer,1969].
Hazard
Moderate fire risk. Vapor is toxic and irritant. Explosive limits in air 1.2–9%.
Health Hazard
Very high vapor concentrations irritate eyes and upper respiratory tract. Continued contact with skin may cause irritation.
Flammability and Explosibility
Flammable
Biochem/physiol Actions
3-Methyl-1-butanol is a pentanol isomer useful in biofuels. It is used as a starting material for the production of isoamyl acetate, a flavoring agent applicable in the food industry. 3-Methyl-1-butanol shows anti-fungal action by inhibiting the hyphal formation and reducing biofilm formation in Candida albicans. It is also used in DNA extraction protocols.
Potential Exposure
(n-isomer); Suspected reprotoxic hazard,
Primary irritant (w/o allergic reaction), (iso-, primary):
Possible risk of forming tumors, Primary irritant (w/o allergic
reaction), (sec-, active primary-, and other isomers)
Primary irritant (w/o allergic reaction). Used as a solvent in
organic synthesis and synthetic flavoring, pharmaceuticals,
corrosion inhibitors; making plastics and other chemicals;
as a flotation agent. The (n-isomer) is used in preparation
of oil additives, plasticizers, synthetic lubricants, and as a
solvent.
Environmental fate
Biological. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM
BOD/mM isoamyl alcohol) and ThOD were 4.46 and 59.5%, respectively (Vaishnav et al., 1987).
Chemical/Physical. Isoamyl alcohol will not hydrolyze because it has no hydrolyzable
functional group (Kollig, 1993).
Shipping
UN2811 Pentanols, Hazard Class: 3; Labels: 3-
Flammable liquid. UN1987 Alcohols, n.o.s., Hazard Class:
3; Labels: 3-Flammable liquid.
Purification Methods
Dry the alcohol by heating with CaO and fractionally distilling, then heating with BaO and redistilling. Alternatively, boil it with concentrated KOH solution, wash it with dilute H3PO4, and dry it with K2CO3, then anhydrous CuSO4, before fractionally distilling it. If very dry alcohol is required, the distillate is refluxed with the appropriate alkyl phthalate or succinate as described for ethanol. It is separated from 2-methyl-1-butanol by fractional distillation, fractional crystallisation and preparative gas chromatography. [Beilstein 1 IV 1677.]
Incompatibilities
Forms an explosive mixture with air.
Contact with strong oxidizers and hydrogen trisulfide may
cause fire and explosions. Incompatible with strong acids.
Violent reaction with alkaline earth metals forming hydrogen,
a flammable gas.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator
equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed.
Check Digit Verification of cas no
The CAS Registry Mumber 123-51-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 123-51:
(5*1)+(4*2)+(3*3)+(2*5)+(1*1)=33
33 % 10 = 3
So 123-51-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
123-51-3Relevant articles and documents
Influence of Alkali Promoters in the Selective Hydrogenation of 3-Methyl-2-butenal over Ru/SiO2 Catalysts
Waghray, Akshay,Wang, Jian,Oukaci, Rachid,Blackmond, Donna G.
, p. 5954 - 5959 (1992)
The addition of potassium as a promoter to a Ru/SiO2 catalyst resulted in a striking shift in product selectivity in the hydrogenation of 3-methyl-2-butenal.The rate of hydrogenation at the C=O bond to produce the unsaturated alcohol increased concomitant with a decrease in the rate of C=C hydrogenation.IR spectroscopy showed a strong perturbation of the C=O bond for the alkali-promoted catalyst, and volumetric chemisorption and TPD results suggested that the alkali species blocked adsorption at low-coordination Ru sites.These adsorption and reaction studies suggest that polarization of the adsorbed substrate at the C=O bond is responsible for the significant shift in product selectivity upon alkali promotion.This work combines spectroscopic tools with the use of the catalytic reaction itself as a probe of catalyst surface chemistry.
Efficient and selective solvent-free homogeneous hydrogenation of aldehydes under mild reaction conditions using [RuCl2(dppb)(ampy)]
Angelini, Tommaso,Roseblade, Stephen,Zanotti-Gerosa, Antonio
, (2020)
The efficient, solvent-free homogeneous hydrogenation of aldehydes has been accomplished using the catalysts [RuCl2(dppb)(ampy)] and [RuCl2(dppf)(ampy)], providing high conversion to the corresponding alcohols at molar catalyst loadings of 10,000/1–50,000/1. A solvent-free protocol has been developed, allowing aldehydes to be efficiently reduced avoiding by-product formation and with minimal waste generation.[Formula presented]
Reactivity of 3-Methyl-Crotonaldehyde on Pt(111)
Birchem, T.,Pradier, C. M.,Berthier, Y.,Cordier, G.
, p. 503 - 510 (1994)
The reactivities of an α,β-unsaturated aldehyde, 3-methyl-crotonaldehyde, and of its two monohydrogenated products, 3-methyl-crotyl alcohol and 3-methyl-butyraldehyde have been investigated on a well-defined Pt(111) surface by low-pressure adsorption, thermal desorption, and high-pressure gas-phase hydrogenation experiments.Two kinetic regimes have been found when varying the 3-methyl-crotonaldehyde partial pressure and, in both cases, a rate-determining step has been proposed.At the origin of the reaction the high selectivity for 3-methyl-crotyl alcohol can be accounted for by the nature of the most abundant C5H9O isomer adsorbed species, the latter being determined by geometric effects.The influence of the 3-methyl-crotonaldehyde partial pressure on selectivities can be easily explained by a competitive hydrogenation between this molecule and the 3-methyl-crotyl alcohol.A similar previous study on Pt(111) has shown a quite different behaviour, and this work underlines the importance of the crystalline orientation of the platinum surface on the observed selectivities.
Microwave-Induced Esterification Using Heterogeneous Acid Catalyst in a Low Dielectric Constant Medium
Kabza, Konrad G.,Chapados, Brian R.,Gestwicki, Jason E.,McGrath, Jessica L.
, p. 1210 - 1214 (2000)
-
-
Pedler
, p. 74 (1868)
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Photocatalytic Regeneration of Nicotinamide Cofactors by Quantum Dot-Enzyme Biohybrid Complexes
Brown, Katherine A.,Wilker, Molly B.,Boehm, Marko,Hamby, Hayden,Dukovic, Gordana,King, Paul W.
, p. 2201 - 2204 (2016)
We report the characterization of biohybrid complexes of CdSe quantum dots and ferredoxin NADP+-reductase for photocatalytic regeneration of NADPH. Illumination with visible light led to reduction of NADP+ to NADPH, with an apparent kcat of 1400 h-1. Regeneration of NADPH was coupled to reduction of aldehydes to alcohols catalyzed by a NADPH-dependent alcohol dehydrogenase, with each NADPH molecule recycled an average of 7.5 times. The quantum yield both of NADPH and alcohol production were 5-6% for both products. Light-driven NADPH regeneration was also demonstrated in a multienzyme system, showing the capacity of QD-FNR complexes to drive continuous NADPH-dependent transformations.
Thosar, B. V.,Bapat, R. N.
, p. 472 - 476 (1938)
Superior performance of a nanostructured platinum catalyst in water: Hydrogenations of alkenes, aldehydes and nitroaromatics
Maity, Prasenjit,Basu, Susmit,Bhaduri, Sumit,Lahiri, Goutam Kumar
, p. 1955 - 1962 (2007)
The hydrogenations of >C=CC=O and nitro groups in ArNO 2, with a water-soluble, polymer [poly(diallyldimethylammonium chloride)] supported, platinum carbonyl cluster {[Pt30(CO) 60]2-} derived catalyst 1, have been studied. The performance of 1 has been compared with that of two other platinum catalysts: catalyst 2 prepared by the hydrogen reduction of [PtCl6]2- supported on the same water-soluble polymer, and 3, a commercial platinum catalyst (5 % Pt on alumina). Our catalyst 1 has been found to be more active than 2 and 3, and by TEM it has been shown that the nanoparticles in 1 are much smaller than those in 2. In the hydrogenation of o-chloronitrobenzene both 1 and 2 were found to be more selective (no hydrodehalogenation) than 3. To evaluate the advantages of water as a solvent, comparative studies have been carried out in three different solvent systems: water, methanol and a 1:1 mixture of water and toluene. Hydrogenations in methanol have been found to be accompanied by induction times while no such induction time is observed in water. Both liquid (methyl pyruvate, benzaldehyde, safflower oil and styrene) and waterinsoluble solid nitroaromatics (o- and m-chloronitrobenzene and p-aminonitrobenzene) have been tested as substrates, and for all the substrates the activity in water was found to be higher.
-
Josephson,v.Euler
, p. 54 (1924)
-
Structural insights into the cofactor-assisted substrate recognition of yeast methylglyoxal/isovaleraldehyde reductase Gre2
Guo, Peng-Chao,Bao, Zhang-Zhi,Ma, Xiao-Xiao,Xia, Qingyou,Li, Wei-Fang
, p. 1486 - 1492 (2014)
Saccharomyces cerevisiae Gre2 (EC1.1.1.283) serves as a versatile enzyme that catalyzes the stereoselective reduction of a broad range of substrates including aliphatic and aromatic ketones, diketones, as well as aldehydes, using NADPH as the cofactor. Here we present the crystal structures of Gre2 from S. cerevisiae in an apo-form at 2.00 ? and NADPH-complexed form at 2.40 ? resolution. Gre2 forms a homodimer, each subunit of which contains an N-terminal Rossmann-fold domain and a variable C-terminal domain, which participates in substrate recognition. The induced fit upon binding to the cofactor NADPH makes the two domains shift toward each other, producing an interdomain cleft that better fits the substrate. Computational simulation combined with site-directed mutagenesis and enzymatic activity analysis enabled us to define a potential substrate-binding pocket that determines the stringent substrate stereoselectivity for catalysis.
METHOD FOR PRODUCING BIO ALCOHOL FROM INTERMEDIATE PRODUCTS OF ANAEROBIC DIGESTION TANK
-
Paragraph 0043-0048, (2021/05/25)
The present invention relates to a method for producing a bio-alcohol by reacting a mixture of volatile fatty acid with methanol in 2 through 11 in a reactor in the presence of a 280 °C-membered alkaline earth metal catalyst or 400 °C transition metal catalyst formed based on a support.
Method for recycling byproducts in synthesis of diphenyl sulfide compound
-
Paragraph 0115; 0121-0123, (2021/03/30)
The invention provides a method for recycling byproducts in synthesis of a diphenyl sulfide compound. The byproducts comprise alkyl alcohol and dimethyl disulfide. The method comprises the steps of (1) mixing the byproducts in synthesis of the diphenyl sulfide compound with a sodium nitrite aqueous solution, adding concentrated hydrochloric acid for reaction, and obtaining alkyl nitrite and dimethyl disulfide; and (2) mixing the products obtained in the step (1) with copper powder, adding an aniline compound for reaction, carrying out desolvation treatment on the obtained reaction solution toobtain a diphenyl sulfide compound and byproducts, and returning the byproducts to the step (1). According to the recycling method, the byproducts do not need to be separated, the byproducts serve asraw materials to be directly applied to synthesis of the diphenyl sulfide compound, the process steps are simple and safe, cyclic utilization of the materials is achieved, and the raw material cost ofindustrial production of the diphenyl sulfide compound and the treatment cost of industrial three wastes are remarkably reduced.
