78-92-2 Usage
Uses
Used in Chemical Industry:
2-Butanol is used as a solvent and an extraction solvent for various applications, including the production of intermediates of methyl ethyl ketone and the preparation of butyl acetate and sec-butyl. It is also used as a processing agent, herbicide, and in organic synthesis.
Used in Paint and Coatings Industry:
2-Butanol is used as a solvent in lacquers and alkyd enamels, as well as in paint removers and industrial cleaners.
Used in Perfumery and Flavor Industry:
2-Butanol is used in the production of fruit essences, perfumes, and as a solvent for spices.
Used in Polishing and Cleaning Materials Industry:
2-Butanol is used in the formulation of polishes, cleaning materials, and as a component in hydraulic brake fluids.
Used in Dyestuffs Industry:
2-Butanol is used in the production of dyes and dyestuffs.
Used in Mining Industry:
The xanthate derivatives of 2-butanol are used in ore flotation processes.
Used in Laboratory Applications:
2-Butanol is used as a solvent and chromatography reagent in various laboratory applications.
Physical and Chemical Properties
2-butanol is also known as methyl ethyl alcohol, chemical formula is CH3CH2CHOHCH3. Molecular weight is 74.12. It is colorless liquid with a strong aroma of mint, flammable, volatile, with optical activity. The molecule has a chiral carbon atom, can be present in three forms of right-handed body, left-handed body and racemic body, dl-body: the relative density is 0.8063. Melting point is-114.7 ℃. Boiling point is 99.5 ℃, 45.5 ℃ (7.999 × 103Pa). The flash point is 34 ℃. The refractive index is 1.3978. d-body: the relative density is 0.8080. Boiling point is 99.5 ℃. The flash point is 24 ℃. The refractive index is 1.3954. Specific rotation is + 13.9 °. l-body: the relative density is 0.8070. Boiling point is 99.5 ℃. The flash point is 28 ℃. The refractive index is 1.3955. Specific rotation is-13.51 ° (25 ℃). 2-butanol oxidation can generate methyl ethyl ketone and acetic acid. Slightly soluble in water (25 ℃ when 12.5ml/100ml), dissolved in acetone, benzene, miscible with ethanol and ether. This product interacts with water to form an azeotropic mixture, the product content is 68%, the total boiling point is 88.5 ℃. Rat oral is LD506480mg/kg. 2-butanol is the main raw material for producing methyl ethyl ketone, butyl acetate, sec-butyl acetate, and also used as a solvent and extraction agent, the raw materials of plasticizers, processing agents, herbicides, but also for synthesis of spices, flavors, coloring agents, wetting agent, cleaning agents and solvents of many natural resin, linseed oil and castor oil.
Butanol isomers
Butanol is an important industrial raw material, also known as hydroxy butane, a monohydric alcohol, the lowest level alcohol for the same family which can have two or more isomers, butanol has four kinds of isomers, namely n-butanol, 2-butanol, tert-butanol and isobutanol. Relative molecular mass is 74.12. Butanol has the common property of alcohols, such as water-like, reacts with metal to produce alkoxide, reacts with halogen acid to produce halogenated hydrocarbons, dehydrates into alkenes, oxidation (or dehydrogenation) reaction to produce aldehydes and acids, and reacts with organic acids or oxygen-containing inorganic acid to generate ester and so on. In the four isomers, the toxicity of n-butanol is minimal, the toxicity of the other three is not large, but their irritation is great, with irritation to the skin and mucous membrane. Inhalation of large vapors can cause coma. The maximum allowable concentration at workplace is 100 × 10-6. Butanol can be directly used as a solvent, extraction agent, dehydrating agent, plasticizer, mineral processing agent, anti-aging agent, herbicide and so on.
Physical and chemical properties and toxicity of butanol are different due to isomers. The solubility in water depends on their structure, chemical properties depend on hydroxy location in alcohol: n-butanol and iso-butanol are primary alcohols, can be oxidized into the corresponding aldehyde or acid, sec-butyl alcohol is oxidized into the corresponding ketone, t-butanol is unsusceptible to oxidation.
Physicochemical properties comparison chart of 4 isomers of butanol
Under dehydrating catalyst, butanol can produce butene, n-butanol and 2-butene can give 1-butene, 2-butene, 2-butanol can generate 2-butene, isobutanol and tert-butanol generate isobutylene. Under the catalyst of copper and silver, the dehydrogenation generates carbonyl compounds, n-butanol generates butyraldehyde, butanol generates methyl ethyl ketone, isobutanol generate isobutyraldehyde. Under the catalyst, air oxidation can generate acid. Catalyzed by a mineral acid, it reacts with organic acid to generate ester. Reaction with benzene, can generate butyl benzene. Butanol reacts with chlorine to generate butyraldehyde chloride. Under the action of the aluminum catalyst at 300~350 ℃, reacts with ammonia, n-butanol, iso-butanol and 2-butanol react with ammonia to generate butylamine, dibutylamine, tributylamine, t-butanol does not have this character. N-butanol and tert-butanol at 180 ℃ react with hydrogen sulfide to generate butyl mercaptan.
The above information were collated and edited by Xiaonan of lookchem.
Laboratory method for preparing 2-butanol
1, As raw materials 2-butene reacts with sulfuric acid in concentrated sulfuric acid to produce sulfuric acid butyl ester, sulfuric acid ester is then hydrolyzed to produce 2-butanol, and then distillation purification.
2, 2-butanone is used as raw material, under the action of a Grignard reagent, to prepare 2-butanol.
3, cis-2-butene is used as raw material, under the action of boron hydrides, to prepare d-or l-body.
Production method
After adsorption by butane of the cracking petroleum or natural gas in sulfuric acid, then hydrolyze with steam.
Dangerous situations
Prolonged inhalation is toxic, it irritates eye and skin. Flammable, flash point is 406 ℃, there is a greater risk of combustion. The allowable concentration in air of US is 100ppm (305mg/m3).
Incompatibility
Sec-butyl alcohol is incompatible with strong oxidizing agents.
Storage
It is Stored in metal drums, to prevent mechanical damage, best stored in a cool, dry and ventilated, non-flammable place, away from all possible sources of ignition, separated from strong oxidants.
Transport requirements
During transportation, "flammable liquid" shall be marked logo on the container. Others should be the same with "n-butanol".
Extinguish measures
When firing, dry powder fire extinguishing agent, fire-resistant foam or CO2 can be used. Water fighting is invalid, but spray with water in the fire container to keep it cool. If spills, and spills are not lighted, water mist can wash spray spills from the fire, and dilute to non-flammable mixtures. If necessary, water mist can be used to protect the operator to stop the leakage. Other items see the "n-butanol."
Hazards & Safety Information
Category: Flammable liquid
Toxicity grading: Poisoning
Acute toxicity
Oral-rat LD50: 6480 mg/kg, Intravenous-Mouse LD50: 764 mg/kg
Stimulus data
Eyes-rabbit 100 mg/24 hours??? moderate, Skin-rabbit 500 mg/24 hr? mild
Hazardous characteristics
It is explosive when mixed with air, self-oxidized to form explosive peroxides.
Flammability hazard characteristics
in case of fire, high temperature, oxidant, it is flammable, burning to generate irritation smoke, spontaneous combustion in contact with chromium trioxide.
Storage characteristics
Treasury ventilation low-temperature drying, and it is stored from oxidants.
Extinguishing agent
Dry powder, water spray, carbon dioxide, foam
Professional standards
TWA 100 PPM (310 mg/m3)
Production Methods
There are two ways to produce 2-Butanol in industry. The first is the butene hydration method. After pretreatment, n-butene is hydrated with sulfuric acid to obtain 2-Butanol, which is purified to obtain 2-Butanol. The second is the ion exchange resin hydration method, which uses n-butene as raw material, acidic cation exchange resin as catalyst, carries out liquid-phase esterification reaction with organic acid, and then undergoes hydrolysis and rectification to obtain the product.
Production Methods
2-Butanol is produced commercially by the indirect hydration
of n-butenes.
Air & Water Reactions
Highly flammable. Soluble in water.
Reactivity Profile
Attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water (Merck 11th ed. 1989). Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].
Hazard
Toxic, mutagenic, upper respiratory tract
irritant, central nervous system impairment.
Health Hazard
Exposure to 2-butanol may cause irritationof the eyes and skin. The latter effect isproduced by its defatting action on skin. Thistoxic property is mild and similar to thatof other butanol isomers. High concentrationmay produce narcosis. The narcotic effect isstronger than that of n-butanol, probably dueto the higher vapor pressure of the secondaryalcohol.The toxicity is lower than that of itsprimary alcohol analogue.LD50 value, oral (rats): 6480 mg/kg.
Flammability and Explosibility
Flammable
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Poison by intravenous
and intraperitoneal routes. Mildly toxic by
ingestion. Experimental reproductive
effects. A skin and eye irritant. See also nBUTYL ALCOHOL and ALCOHOLS.
Dangerous fire hazard when exposed to heat
or flame. Auto-oxidizes to an explosive
peroxide. Ignites on contact with chromium
trioxide. To fight fire, use water spray,
alcohol foam, CO2, dry chemical.
Incompatible with oxidizing materials.
When heated to decomposition it emits
acrid smoke and fumes.
Environmental fate
Biological. Bridié et al. (1979) reported BOD and COD values of 2.15 and 2.49 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. The ThOD for sec-butyl alcohol is
2.59 g/g. In activated sludge inoculum, following a 20-d adaptation period, 98.5% COD removal
was achieved. The average rate of biodegradation was 55.0 mg COD/g?h (Pitter, 1976).
Photolytic. The estimated half-life of sec-butyl alcohol for the reaction of OH radicals in air
ranges from 129 d to 23 yr (Anbar and Neta, 1967).
Chemical/Physical. sec-Butyl alcohol will not hydrolyze in water because it does not contain a
hydrolyzable group (Kollig, 1993).
Check Digit Verification of cas no
The CAS Registry Mumber 78-92-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 78-92:
(4*7)+(3*8)+(2*9)+(1*2)=72
72 % 10 = 2
So 78-92-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
78-92-2Relevant articles and documents
METHOD FOR PRODUCING ALCOHOL
-
Paragraph 0104; 0106, (2022/02/05)
The present invention provides a method for selectively producing an alcohol by efficiently hydrogenating a lactone. The present invention is a method for producing an alcohol, the method including hydrogenating a substrate lactone represented by Formula (1), in the presence of a catalyst described below, to produce an alcohol that is represented by Formula (2). In the formulae, R represents a divalent hydrocarbon group which may have a hydroxyl group. The catalyst comprises: metal species including M1 and M2; and a support supporting the metal species, and wherein M1 is rhodium, platinum, ruthenium, iridium, or palladium; M2 is tin, vanadium, molybdenum, tungsten, or rhenium; and the support is hydroxyapatite, fluorapatite, hydrotalcite, or ZrO2.
Selective palladium nanoparticles-catalyzed hydrogenolysis of industrially targeted epoxides in water
Duval, Marion,Deboos, Victor,Hallonet, Agnès,Sagorin, Gilles,Denicourt-Nowicki, Audrey,Roucoux, Alain
, p. 261 - 268 (2021/03/22)
Palladium nanoparticles, with core sizes of ca. 2.5 nm, were easily synthesized by chemical reduction of Na2PdCl4 in the presence of hydroxyethylammonium salts and proved to be efficient for the selective hydrogenolysis of various aromatic, alkylphenyl, aliphatic epoxides in water as green solvent. Capping agents of the metal species were screened to define the most suitable micellar nanoreactors on two target substrates of industrial interest, epoxystyrene and 7,8-epoxy-2-methoxy-2,6-dimethyloctane. In our conditions, the hydrogenolysis of epoxystyrene proved to be pH-dependent, producing either the diol under acidic conditions, or the sweet-smelling 2-phenylethanol in the presence of a base. Promisingly, 7,8-epoxy-2-methoxy-2,6-dimethyloctane was completely and selectively hydrogenated into Florsantol, a sandalwood odorant at a multigram scale (40 g and up to 175g). A general mechanism for the palladium nanoparticles-catalyzed hydrogenolysis of terminal epoxides was proposed according to steric and electronic properties and finely corroborated with deuterium labelling experiments.
Hydrogen-Catalyzed Acid Transformation for the Hydration of Alkenes and Epoxy Alkanes over Co-N Frustrated Lewis Pair Surfaces
Deng, Qiang,Deng, Shuguang,Gao, Ruijie,Li, Xiang,Tsang, Shik Chi Edman,Wang, Jun,Zeng, Zheling,Zou, Ji-Jun
, p. 21294 - 21301 (2021/12/17)
Hydrogen (H2) is widely used as a reductant for many hydrogenation reactions; however, it has not been recognized as a catalyst for the acid transformation of active sites on solid surface. Here, we report the H2-promoted hydration of alkenes (such as styrenes and cyclic alkenes) and epoxy alkanes over single-atom Co-dispersed nitrogen-doped carbon (Co-NC) via a transformation mechanism of acid-base sites. Specifically, the specific catalytic activity and selectivity of Co-NC are superior to those of classical solid acids (acidic zeolites and resins) per micromole of acid, whereas the hydration catalysis does not take place under a nitrogen atmosphere. Detailed investigations indicate that H2 can be heterolyzed on the Co-N bond to form Hδ-Co-N-Hδ+ and then be converted into OHδ-Co-N-Hδ+ accompanied by H2 generation via a H2O-mediated path, which significantly reduces the activation energy for hydration reactions. This work not only provides a novel catalytic method for hydration reactions but also removes the conceptual barriers between hydrogenation and acid catalysis.
Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor
Morimoto, Mariko,Cao, Wendy,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean
supporting information, p. 2108 - 2114 (2021/02/06)
Supramolecular catalysts emulate the mechanism of enzymes to achieve large rate accelerations and precise selectivity under mild and aqueous conditions. While significant strides have been made in the supramolecular host-promoted synthesis of small molecules, applications of this reactivity to chemoselective and site-selective modification of complex biomolecules remain virtually unexplored. We report here a supramolecular system where coencapsulation of pyridine-borane with a variety of molecules including enones, ketones, aldehydes, oximes, hydrazones, and imines effects efficient reductions under basic aqueous conditions. Upon subjecting unprotected lysine to the host-mediated reductive amination conditions, we observed excellent ?-selectivity, indicating that differential guest binding within the same molecule is possible without sacrificing reactivity. Inspired by the post-translational modification of complex biomolecules by enzymatic systems, we then applied this supramolecular reaction to the site-selective labeling of a single lysine residue in an 11-amino acid peptide chain and human insulin.
Ruthenium-p-cymene Complex Side-Wall Covalently Bonded to Carbon Nanotubes as Efficient Hybrid Transfer Hydrogenation Catalyst
Blanco, Matías,Cembellín, Sara,Agnoli, Stefano,Alemán, José
, p. 5156 - 5165 (2021/11/05)
A half-sandwich ruthenium-p-cymene organometallic complex has been immobilized at Single Walled Carbon Nanotubes (SWNT) sidewalls through a stepwise covalent chemistry protocol. The introduction of amino groups by means of diazonium-chemistry protocols leads the grafting at the outer walls of the nanotubes. This hybrid material is active in the transfer hydrogenation of ketones to yield alcohols, using as hydrogen source 2-propanol. SWNT?NH2?Ru presents a broad scope, performing the reaction under aerobic conditions and can be recycled over 9 consecutive reaction runs without losing activity or leaching ruthenium out. Comparison of the activity with related homogeneous catalysts reveals an improved performance due to the covalent bond between the metal and the material, achieving turnover frequencies as high as 192774 h?1.
Synthesis of new rhodium(III) complex by benzylic C[sbnd]S bond cleavage of thioether containing NNS donor Schiff base ligand: Investigation of catalytic activity towards transfer hydrogenation of ketones
Biswas, Sujan,Das, Akash,Kumar Manna, Chandan,Kumar Mondal, Tapan,Naskar, Rahul
, (2020/11/04)
A new rhodium(III)-triphenylphosphine mixed ligand complex, [Rh(PPh3)(L)Cl2] (1) is synthesized by benzylic C[sbnd]S bond cleavage of L-CH2Ph ligand (where, L-CH2Ph = 2-(benzylthio)-N-(pyridin-2-ylmethylene)aniline). The complex is thoroughly characterized by several spectroscopic techniques. Geometry of the complex is confirmed by single crystal X-ray crystallography. Electronic structure, redox properties, absorption and emission properties of the complex were studied. DFT and TDDFT calculations were carried out to interpret the electronic structure and absorption properties of the complex respectively. The synthesized Rh(III) complex was tested as catalyst towards transfer hydrogenation reaction of ketones in iPrOH and an excellent catalytic conversion was observed under mild conditions.
METHOD FOR PRODUCING BIO ALCOHOL FROM INTERMEDIATE PRODUCTS OF ANAEROBIC DIGESTION TANK
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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.
Hydrodeoxygenation of C4-C6 sugar alcohols to diols or mono-alcohols with the retention of the carbon chain over a silica-supported tungsten oxide-modified platinum catalyst
Betchaku, Mii,Cao, Ji,Liu, Lujie,Nakagawa, Yoshinao,Tamura, Masazumi,Tomishige, Keiichi,Yabushita, Mizuho
supporting information, p. 5665 - 5679 (2021/08/16)
The hydrodeoxygenation of erythritol, xylitol, and sorbitol was investigated over a Pt-WOx/SiO2 (4 wt% Pt, W/Pt = 0.25, molar ratio) catalyst. 1,4-Butanediol can be selectively produced with 51% yield (carbon based) by erythritol hydrodeoxygenation at 413 K, based on the selectivity over this catalyst toward the regioselective removal of the C-O bond in the -O-C-CH2OH structure. Because the catalyst is also active in the hydrodeoxygenation of other polyols to some extent but much less active in that of mono-alcohols, at higher temperature (453 K), mono-alcohols can be produced from sugar alcohols. A good total yield (59%) of pentanols can be obtained from xylitol, which is mainly converted to C2 + C3 products in the literature hydrogenolysis systems. It can be applied to the hydrodeoxygenation of other sugar alcohols to mono-alcohols with high yields as well, such as erythritol to butanols (74%) and sorbitol to hexanols (59%) with very small amounts of C-C bond cleavage products. The active site is suggested to be the Pt-WOx interfacial site, which is supported by the reaction and characterization results (TEM and XAFS). WOx/SiO2 selectively catalyzed the dehydration of xylitol to 1,4-anhydroxylitol, whereas Pt-WOx/SiO2 promoted the transformation of xylitol to pentanols with 1,3,5-pentanetriol as the main intermediate. Pre-calcination of the reused catalyst at 573 K is important to prevent coke formation and to improve the reusability.
Enzymatic Oxidation of Butane to 2-Butanol in a Bubble Column
Perz, Frederic,Bormann, Sebastian,Ulber, Roland,Alcalde, Miguel,Bubenheim, Paul,Hollmann, Frank,Holtmann, Dirk,Liese, Andreas
, p. 3666 - 3669 (2020/06/17)
Unspecific peroxygenases have recently gained significant interest due to their ability to catalyse the hydroxylation of non-activated C?H bonds using only hydrogen peroxide as a co-substrate. However, the development of preparative processes has so far mostly concentrated on benzylic hydroxylations using liquid substrates. Herein, we demonstrate the application of a peroxygenase for the hydroxylation of the inert, gaseous substrate butane to 2-butanol in a bubble column reactor. The influence of hydrogen peroxide feed rate and enzyme loading on product formation, overoxidation to butanone and catalytic efficiency is investigated at 200 mL scale. The process is scaled up to 2 L and coupled with continuous extraction. This setup allowed the production of 115 mmol 2-butanol and 70 mmol butanone with an overall total turnover number (TTN) of over 15.000, thereby demonstrating the applicability of peroxygenases for preparative hydroxylation of such inert, gaseous substrates at mild reaction conditions.
Synthesis and characterization of silica-coated magnetite nanoparticles modified with bis(pyrazolyl) triazine ruthenium(II) complex and the application of these nanoparticles as a highly efficient catalyst for the hydrogen transfer reduction of ketones
Mobinikhaledi, Akbar,Moghanian, Hassan,Ajerloo, Bahram,Dousti, Fatemeh
, (2019/12/24)
We present a facile and efficient method for modifying the surface of silica-coated Fe3O4 magnetic nanoparticles (MNPs) with bis(pyrazolyl) triazine ruthenium(II) complex [MNPs@BPT–Ru (II)]. Field emission-scanning electron microscopy, thermogravimetric/derivative thermogravimetry analysis, X-ray powder diffraction, Fourier-transform infrared spectroscopy, vibrating sample magnetometry, and energy-dispersive X-ray spectrometry analyses were employed for characterizing the structure of these nanoparticles. MNPs@BPT–Ru(II) nanoparticles proved to be a magnetic, reusable, and heterogeneous catalyst for the hydrogen transfer reduction of ketone derivatives. In addition, highly pure products were obtained with excellent yields in relatively short times in the presence of this catalyst. A comparison of this catalyst with those previously used for the hydrogen transfer reactions proved the uniqueness of MNPs@BPT–Ru(II) nanoparticle which is due to its inherent magnetic properties and large surface area. The presented method also had other advantages such as simple reaction conditions, eco-friendliness, high recovery ability, easy work-up, and low cost.
