110-19-0 Usage
description
Isobutyl acetate, also known as n-propyl acetate, is the esterfication product between acetic acid and 2-butanol. It is a water-white liquid with flavor of soft fruit ester. It is slightly soluble in water, miscible with ethanol, ethyl ether as well as many other kinds of organic solvent including alcohol, ether and hydrocarbon. It can be mainly used as the diluent of nitro-lacquer and perchlorethylene paint and the solvents of nitrocellulose and lacquer as well as the substitution solvent of butyl acetate and methyl isobutyl ketone. It can also be used as a component of the flavoring agent. It can also be used as the diluent of plastic printing paste and the extraction agent in the pharmaceutical industry.
Sec-butyl acetate has excellent capability of dissolving many substances. It can be industrially applied as the solvent for manufacturing of nitrocellulose paint, acrylic paint, polyurethane paint, etc., these paints can also be used as an aircraft wing paint, artificial leather coatings and automotive coatings. Its dissolving capability is similar as n-butyl acetate and isobutyl acetate. In the coating formulation, it can be widely adopted for substitution of n-butyl acetate and isobutyl acetate. In metallic paints, people can apply butyl acetate to dissolve the cellulose acetate butyrate to obtain 15% to 20% solution.
The above information is edited by the lookchem of Dai Xiongfeng.
Chemical Properties
Different sources of media describe the Chemical Properties of 110-19-0 differently. You can refer to the following data:
1. It is a water-white liquid with soft fruit ester flavor. It is miscible with a variety of organic solvents such as alcohols, ethers and hydrocarbons.
2. Isobutyl acetate is a colorless liquid with a fruit flavor. Isobutyl acetate is moisture sensitive, incompatible with ignition sources, moisture, excess heat, strong oxidizing agents, and strong bases; on decomposition, it releases carbon monoxide and carbon dioxide. It is used for nitrification fiber and paint solvents, chemical reagents, and modulation spices
3. Isobutyl acetate, also known as 2-methylpropyl ethanoate (IUPAC name) or β-methylpropyl
acetate, is a common solvent. It is produced from the esterifi cation of isobutanol with acetic
acid. It is used as a solvent for lacquer and nitrocellulose. Like many esters, it has a fruity
or fl oral smell at low concentrations and occurs naturally in raspberries, pears, and other
plants. At higher concentrations, the odor can be unpleasant and may cause symptoms of
CNS depression, such as nausea, dizziness, and headache
Uses
Different sources of media describe the Uses of 110-19-0 differently. You can refer to the following data:
1. Isobutyl Acetate can be used as organic solvent, the solvent of nitrocellulose and lacquer, extraction agent, dehydrating agents. It can also be applied to collodion, nitrocellulose, varnishes, leather, pharmaceuticals, plastics and perfume industry.
2. Solvent; flavoring
3. Isobutyl acetate is used as a solvent and as aflavoring agent.
4. Isobutyl Acetate is a flavoring agent that is a clear colorless liquid
with a fruity odor resembling banana when diluted. it is soluble in
alcohol, propylene glycol, most fixed oils, and mineral oil, and
slightly soluble in water. it is obtained by synthesis.
Content Analysis
It can be determined according to the method 1 in ester assay (OT-18). The amount of the sample for taking is 1g. The equivalency factor (e) for the calculation can be taken as 58.08. Alternatively, people can apply non-polar column method via gas chromatography (GT-10-4) for the determination.
The above information is edited by the lookchem of Dai Xiongfeng.
Toxicity
LD50: 13400 mg/kg (rat, oral).
GRAS (FEMA).
Limited use
FEMA (mg/kg): soft drinks: 11; cold drink: 16; Confectionery: 36; Bakery: 35; pudding class: 170; gum: 860; coating: 5.5.
Take appropriate amount as limit (FDA§172.515,2000).
Production method
It can be obtained via the esterfication between iso-butanol and acetic anhydride in the presence of sulfuric acid. Mix the acetic anhydride and iso-butanol solution followed by adding drop wise of sulfuric acid. Heat for reflux of 5-6 h after a bit cooling, wash the refluxed liquid with water for 2-3 times. Use sodium carbonate for neutralizing with sodium carbonate, wash with water until neutralized, dry over calcium chloride with vacuum distillation in oil bath to derive the finished products.
Description
Isobutyl acetate has a fruity (currant-pear), floral (hyacinth-rose)
odor and a characteristic ether-like, slightly bitter flavor. May be
prepared by direct esterification of isobutyl alcohol with acetic
acid.
Physical properties
Colorless liquid with a fruity odor. Experimentally determined detection and recognition odor
threshold concentrations were 1.7 mg/m3 (360 ppbv) and 2.4 mg/m3 (510 ppbv), respectively
(Hellman and Small, 1974).
Occurrence
Reported found in, apple, apricot, banana, currants, guava, grapes, melon, pear, blackcurrant, papaya, pineapple, strawberry, vinegar, wheat bread, Parmesan and Gruyere cheese, beef fat, beer, cognac, rum, cider, whiskies, sherry, grape
wines, port, olive, cocoa, passion fruit, plum, starfruit, bantu beer, plum and grape brandy, mango, tamarind, apple brandy, figs, plum
wine, litchi, sake, nectarine, naranjilla fruit, Cape gooseberry and Roman chamomile oil.
Definition
ChEBI: The acetate ester of isobutanol.
Preparation
By direct esterification of isobutyl alcohol with acetic acid.
Production Methods
Isobutyl acetate may be made from methyl isobutyl
ketone. It may also be made by treating isobutanol
with acetic acid in the presence of catalysts. The
Tischenko reaction of acetaldehyde with isobutyraldehyde
yields a mixture of isobutyl acetate with ethyl acetate and
isobutyl isobutyrate.
Aroma threshold values
Detection: 65 to 880 ppb
Taste threshold values
Taste characteristics at 30 ppm: sweet fruity with a banana tutti-frutti note.
General Description
A clear colorless liquid with a fruity odor. Flash point 64°F. Less dense than water (6.2 lb / gal) and insoluble in water. Vapors are heavier than air .
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Isobutyl acetate reacts exothermically with acids to give alcohols and other acids. May react sufficiently exothermically with strong oxidizing acids to ignite the reaction products. Reactions with bases also generate heat. Combination with strong reducing agents (alkali metals and hydrides) generates flammable hydrogen.
Hazard
Flammable, dangerous fire risk.
Health Hazard
Different sources of media describe the Health Hazard of 110-19-0 differently. You can refer to the following data:
1. Vapors may irritate upper respiratory tract and cause nausea, vomiting, dizziness and loss of consciousness. Liquid irritates eyes and may irritate skin.
2. Isobutyl acetate is more toxic but less of anirritant than n-butyl acetate. The toxic symp toms include headache, drowsiness, irritationof upper respiratory tract, and anesthesia.A 4-hour exposure to 8000 ppm was lethalto rats. It produced mild to moderate irri tation on rabbits’ skin. The irritation ineyes was also mild to moderate. The LD50oral value in rabbit is within the range4800 mg/kg.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Notclassified
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: Softens and dissolves many types of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Biochem/physiol Actions
Taste at 10 ppm
Potential Exposure
n-Butyl acetate is an important solvent
in the production of lacquers, leather and airplane dopes,
and perfumes. It is used as a solvent and gasoline additive.
sec-Butyl acetate is used as a widely used solvent for
nitrocellulose, nail enamels and many different purposes.
tert-Butyl acetate is common industrial solvent used in the
making of lacquers, artificial leather, airplane dope, perfume; and as a food additive. Isobutyl acetate is used as a
solvent and in perfumes and artificial flavoring materials
Source
A product of whiskey fermentation (quoted, Verschueren, 1983). Isobutyl acetate was
identified as a volatile constituent released by fresh coffee beans (Coffea canephora variety
Robusta) at different stages of ripeness (Mathieu et al., 1998).
Environmental fate
Chemical/Physical. Slowly hydrolyzes in water forming 2-methylpropanol and acetic acid.
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent
concentration of 180 mg/L. The adsorbability of the carbon used was 164 mg/g carbon (Guisti et
al., 1974).
Shipping
UN1123 Butyl acetates, Hazard Class: 3; Labels:
3—Flammable liquid.
Incompatibilities
All butyl acetates are incompatible with
nitrates, strong oxidizers; strong alkalies; strong acids.
Butyl acetates may form explosive mixture with air; reacts
with water, on standing, to form acetic acid and n-butyl
alcohol. Violent reaction with strong oxidizers and
potassium-tert-butoxide. Dissolves rubber, many plastics,
resins and some coatings. May accumulate static electrical
charges, and may cause ignition of its vapors
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 110-19-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 110-19:
(5*1)+(4*1)+(3*0)+(2*1)+(1*9)=20
20 % 10 = 0
So 110-19-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3
110-19-0Relevant articles and documents
Synthesis of a novel multi-SO3H functionalized ionic liquid and its catalytic activities
Xudong, Sun,Huiquan, Xiao,Yijun, Du,Jingjing, Zhang,Xuezheng, Liang,Chenze, Qi
, p. 301 - 305 (2012)
A novel multi-SO3H functionalized ionic liquid is synthesized and a detailed account of its cata- lytic activities in acetalization and acetylation is given. The results showed that the ionic liquid is very efficient in the conventional acid-catalyzed reactions with good to excellent yields within a short reaction time. Oper- ational simplicity, small amounts required, low cost of the catalyst, high yields, scalability and reusability are the key features of this methodology, which indicates the high potentialities of the novel ionic liquid to be used in environmentally friendly processes. Pleiades Publishing, Ltd., 2012.
The Phase-Transfer Catalysed Synthesis of Esters of Carboxylic Acids
Szeja, Wieslaw
, p. 402 - 403 (1980)
-
Green, efficient and economical coal fly ash based phosphomolybdic acid catalysts: preparation, characterization and application
Malpani, Sakshi Kabra,Goyal, Deepti,Katara, Stuti,Rani, Ashu
, p. 3017 - 3034 (2021/02/26)
Abstract: Cost-effective, efficient and green solid acid catalysts have been synthesized by incipient wetness impregnation of various weight fractions of phosphomolybdic acid (5, 10, 15 and 25 wt. %) on mechanically and thermally activated coal fly ash. N2 adsorption–desorption, XRD, FT-IR, SEM, SEM–EDX, TEM, TGA, UV–Vis DRS, solid state 31P MAS NMR were used for characterization of as synthesized catalysts. Catalytic active sites were developed on inert surface of coal fly ash by using various activation techniques whose performance was assessed over a series of acylation of various aliphatic alcohols. For rapid and higher catalytic activity, reactions were conducted in microwave heating mode. Impregnation of phosphomolybdic acid generates Lewis acidic sites on coal fly ash surface as inferred by pyridine adsorbed FT-IR studies which were then utilized in acylation reactions. Various reaction parameters like weight fraction of catalysts, molar ratio of reactants, time, temperature, etc. were optimized for attaining highest conversion %. The catalyst with 15 wt. % of phosphomolybdic acid was found to be more efficient and could be recycled up to five reaction cycles with analogous conversion %. Negligible leaching of catalyst was confirmed by hot filtration test. This work suggests an alternative approach for valorisation of industrial solid waste, coal fly ash in development of innovative, economical solid catalysts. Graphic abstract: [Figure not available: see fulltext.].
Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols
Koszelewski, Dominik,Brodzka, Anna,Madej, Arleta,Trzepizur, Damian,Ostaszewski, Ryszard
, p. 6331 - 6342 (2021/05/06)
Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.
Enzyme-Catalyzed Synthesis of Esters in Water
Mestrom, Luuk,Claessen, Jord G. R.,Hanefeld, Ulf
, p. 2004 - 2010 (2019/04/14)
MsAcT catalyzes the esterification of primary alcohols in water. When utilizing acid and alcohol as starting materials low yields dictated by thermodynamics were observed. However, with activated esters such as ethyl acetate and vinyl acetate very high yields of the desired ester can be achieved in combination with the appropriate alcohol. This study investigated both the intrinsic kinetic properties of MsAcT for the hydrolysis and transesterification of esters in water as well as the thermodynamics of the reaction. In comparison to the chemical or enzymatic ester synthesis using either toxic reagent, and harsh organic solvents, the MsAcT-catalyzed synthesis of esters of primary alcohols can be achieved efficiently in water without neutralization steps.
