Grundinformationen
- Standard-SMILES
CC(=O)OCC(C)C- InChIKey
GJRQTCIYDGXPES-UHFFFAOYSA-N- Summenformel
- C6H12O2
- Durchschnittliche Molmasse
- 116,16 g/mol
- Monoisotopische Masse
- 116,08372962
Überblick
Isobutyl acetate appears as 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.
Namen und Bezeichner
- Bevorzugter Name
- Isobutyl Acetate
- IUPAC
- 2-methylpropyl acetate
- Lokaler Name
- Isobutylacetat
- Englischer Name
- Isobutyl acetate
- Summenformel
- C6H12O2
- Molmasse
- 116.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
110-19-0- PubChem CID
- 8038
- DTXSID
DTXSID5026837- ChEMBL
CHEMBL46999- ChEBI
CHEBI:50569- UNII
- 7CR47FO6LF
- EC Number
- 203-745-1
- Nikkaji
- J1.972K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,8
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 76,6
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Flammable agents - 3rd degree
Volatile Organic Compound (VOC)
Cosmetics
Cosmetic ingredients (Isobutyl Acetate) -> CIR (Cosmetic Ingredient Review)
Solvent
LogP
log Kow = 1.78
1.78
1.60
Odor
Fruit-like odor
Fruity, floral odor
FRUITY (CURRANT-PEAR), FLORAL (HYACINTH-ROSE) ODOR
SOLVENTY NAIL POLISH-LIKE ODOR
Taste
CHARACTERISTIC ETHER-LIKE, SLIGHTLY BITTER FLAVOR
BANANA TASTE
Density
0.871 at 68 °F (USCG, 1999) - Less dense than water; will float
0.8712 g/cu cm at 20 °C
Bulk density: 7.23 lb/gal
DENSITY OF SATURATED AIR: 1.08 (AIR = 1); CONVERSION FACTORS: 1 MG/L IS EQUIVALENT TO 211 PPM; 1 PPM IS EQUIVALENT TO 4.75 MG/CU M
Relative density (water = 1): 0.87
0.862-0.871
Physikochemische Eigenschaften
- Schmelzpunkt
- -99 °C · -99 °C (lit.)
- Siedepunkt
- 115 · 115-117 °C (lit.)
- Dichte
- 0.867 g/mL · 0.867 g/mL at 25 °C (lit.)
- Dampfdichte
- 4 · >4 (vs air)
- Dampfdruck
- 15 mm · 15 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.39(lit.)
- FEMA
- 2175 · 2175 | ISOBUTYL ACETATE
- Flammpunkt
- 71 °F · 71 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 5.6 g/L · water: soluble5.6g/L at 20°C
- Aggregatzustand
- Liquid
- Farbe
- Clear
- PH
- 5 · 5 (4g/l, H2O, 20℃)
- Geruch (Odor)
- Agreeable fruity odor in low concentrations, disagreeable in higher concentrations; mild, characteristic ester; nonresidual.
- Geruchsart
- fruity
- Odor Threshold
- 0.008 ppm · 0.008ppm
- Biologische Quelle
- synthetic
- Explosionsgrenze
- 2.4 · 2.4-10.5%(V)
- Wasserlöslichkeit
- 7 g/L · 7 g/L (20 ºC)
- Spezifische Wärmekapazität
- 2.01 J/ · Cp(liquid): 2.01 J/(g·K), at 25℃
- Merck
- 14 · 14,5130
- JECFA Number
- 137 · 137
- BRN
- 1741909 · 1741909
- Henry's Law Constant
- (x 10-4 atmm3/mol): 4.85 at 25 °C (approximate - calculated from water solubility and vapor pressure)
- Dielectric constant
- 5.6 · 5.6(20℃)
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- SOLVENTPERFUMING
- InChI
- 1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3
- InChIKey
- GJRQTCIYDGXPES-UHFFFAOYSA-N
- SMILES
- CC(C)COC(C)=O
- LogP
- 2.3 at · 2.3 at 25℃
- Oberflächenspannung
- 23.15 mN/m · 23.15mN/m at 298.15K
- CAS Datenbank
- 110 · 110-19-0(CAS DataBase Reference)
- NIST chemische Informationen
- Isobutyl acetate(110-19-0)
- EPA chemische Informationen
- Isobutyl acetate (110-19-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 6% (177 of 2941) of reports.
Danger
H225 (94%): Highly Flammable liquid and vapor [Danger Flammable liquids]
Gefahrenhinweise
Regulatory Information
Chemical: Acetic acid, 2-methylpropyl ester
Regulation (EC) No 178/2002 (amended)
Acetic acid, 2-methylpropyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-methylpropyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 14-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14421
Acetic acid, 2-methylpropyl ester: HSNO Approval: HSR001092 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Highly flammable. Vapour/air mixtures are explosive.
Fire Potential
A very dangerous fire and moderate explosion hazard when exposed to heat, flame, or oxidizers.
Highly flammable liquid
Health Hazards
Vapors may irritate upper respiratory tract and cause nausea, vomiting, dizziness and loss of consciousness. Liquid irritates eyes and may irritate skin. (USCG, 1999)
· May cause toxic effects if inhaled or absorbed through skin.
DOT ID and Guide
1213 129
1213 129
FDA Requirements
Isobutyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Isobutyl acetate synthetic flavoring substances & adjuvants may be safely used in food in accordance with the following conditions ... They consist of one or more of the following /substances including isobutyl acetate/ used alone or in combination with flavoring substances generally recognized as safe in food, or regulated by an appropriate section in this part.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Use foam, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer for medical attention .
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from NIOSH Pocket Guide for Isobutyl acetate:
General First Aid:
(General first aid procedures)
Firefighting Hazards
Flashback along vapor trail may occur.
The vapors are heavier than air.
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
100.0 [ppm]
Fire Fighting Procedures
To fight fire, use alcohol foam, CO2, dry chemical.
Water may be ineffective on fire /involving isobutyl acetate/. Cool exposed containers with water.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
Fire Fighting: Use self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.
Storage Conditions
... MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ...
Cleanup Methods
1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quant, absorb on paper towels. Evaporate in a safe place (such as a fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn the paper in a suitable location away from combustible materials. Large quantities can be collected and atomized in a suitable combustion chamber. Isobutyl acetate should not be allowed to enter a confined space, such as a sewer, because of the possibility of an explosion.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. Apply appropriate foam to diminish vapor and fire hazard.
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill motion. Use surface active agent (eg detergent, soaps, alcohols), if approved by the EPA.. Inject "universal" gelling agent to solidify encircled spill and increase effectiveness of booms. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount . Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Environmental considerations: Air spill: Apply water spray to mist to knock down vapors.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Isobutyl acetate is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
/Proposed methods of disposal should be used on statutory requirements of the state where disposal is to occur. The usual methods would be expected to include:/ 1) Absorbing in vermiculite, dry sand, earth or a similar material and disposing in a secured sanitary landfill. 2) Atomizing in a suitable combustion chamber.
The following wastewater treatment technologies have been investigated for Isobutyl acetate: Concentration process: Activated carbon.
Toxikologische Informationen
Ecotoxicity Values
LC50; Species: Chlorococcales (Green Algae Order); Conditions: freshwater, static; Concentration: 600000 ug/L for 24 hr /formulation/
LC50; Species: Daphnia magna (Water Flea) age < or =24 hr; Conditions: freshwater, static, 20-22 °C; Concentration: 250000 ug/L for 24 hr /formulation/
TLm Brine shrimp 1200 ppm/24 hr /Conditions of bioassay not specified/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a structure estimation method(2), indicates that isobutyl acetate is expected to have very high mobility in soil(SRC). Volatilization of isobutyl acetate from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.54X10-4 atm-cu m/mole(3). Isobutyl acetate is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 17.8 mm Hg at 25 °C(4). Biodegradation is expected to occur based upon theoretical BODs of 60% and 81% in 5- and 20-day, respectively, fresh water dilution tests(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a structure estimation method(2), indicates that isobutyl acetate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.54X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.2 hours and 4.9 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow of 1.78(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation is expected to occur based upon theoretical BODs of 60% and 81% in 5- and 20-day, respectively, fresh water dilution tests(8). Hydrolysis is expected to occur slowly based upon estimated hydrolysis half-lives of 3 years and 122 days at pH 7 and 8, respectively(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isobutyl acetate, which has a vapor pressure of 17.8 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isobutyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.9 days(SRC), calculated from its rate constant of 5.52X10-12 cu cm/molecule-sec at 25 °C(3). Isobutyl acetate does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Exposure Routes
The substance can be absorbed into the body by inhalation of its vapour.
inhalation, ingestion, skin and/or eye contact
Signs and Symptoms
Cough. Sore throat. Dizziness. Headache.
Dry skin.
Redness.
Nausea.
irritation eyes, skin, upper respiratory system; headache, drowsiness, anesthesia; In Animals: narcosis
Effluent Concentrations
Isobutyl acetate was detected at a mean concentration of 0.23 ug/cu m in the effluent of a waste incinerator in Germany(1). An accidental spill at the BASF plant in Germany released an unspecified concentration of isobutyl acetate into the Rhine River in 1991(2). Isobutyl acetate was identified, not quantified, in the effluent of common household waste(3). UK emissions of isobutyl acetate were reported as 0.44% by mass distribution in 1990(4). Isobutyl acetate was detected in 15 of 44 furniture emission samples(5). Isobutyl acetate was detected but not quantified in the emissions of kitchen waste, kitchen waste exudate and stored food exudate(6).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of isobutyl acetate can be estimated to be 16(SRC). According to a classification scheme(2), this estimated Koc value suggests that isobutyl acetate is expected to have very high mobility in soil.
Regulatorische Informationen
FDA Requirements
Isobutyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Isobutyl acetate synthetic flavoring substances & adjuvants may be safely used in food in accordance with the following conditions ... They consist of one or more of the following /substances including isobutyl acetate/ used alone or in combination with flavoring substances generally recognized as safe in food, or regulated by an appropriate section in this part.
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Isobutyl acetate is produced, as an intermediate or final product, by process units covered under this subpart.
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
Isobutyl acetate is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
Sicherheitsdaten
- OEB
- A
- OEL
- TWA: 150 ppm (700 mg/m3)
- wgk
- 1
- IDLA
- 1,300 ppm [10% LEL]
- tsca
- TSCA listed
- ridadr
- UN 1213
- hs_code
- 2915 39 00
- RTECS-Nr.
- AI4025000
- risk_code
- 11-66
- Toxizität
- LD50 orally in Rabbit: 13400 mg/kg LD50 dermal Rabbit > 17400 mg/kg
- hazard_code
- F
- safety_code
- 16-23-25-29-33
- hazard_class
- 3
- packing_group
- II
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 110-19-0(Hazardous Substances Data)
- Hazard Classifications
- Flam. Liq. 2STOT SE 3
- Selbstentzündungstemperatur
- 793 °F
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Uses
CIR ingredient: Isobutyl Acetate
Solvent uses include nitrocellulose, thinners, sealants, lacquers, and perfumes; [Hawley]
Painting (Solvents) [Category: Paint]
Solvent for nitrocellulose; in thinners, sealants, and topcoat lacquers; perfumery; flavoring agent.
Used in fragrances
INGREDIENT OF SYNTHETIC FLAVOR USEFUL IN BANANA, RASPBERRY, STRAWBERRY, BUTTER.
U.S. Production
2023: 10,000,000 - <50,000,000 lb
(1975) GREATER THAN 4.54X10+5 GRAMS
(1984) 3.8X10+10 g
Acetic acid, 2-methylpropyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1712]
For more U.S. Production (Complete) data for ISOBUTYL ACETATE (6 total), please visit the HSDB record page.
Methods of Manufacturing
Preparation from isobutyl alcohol plus acetic acid
Tischenko reaction of acetaldehyde with isobutyraldehyde yields a mixture of isobutyl acetate with ethyl acetate and isobutyl isobutyrate
Treating isobutanol with acetic acid in the presence of catalysts.
Formulations/Preparations
Grades: Technical; solvent; perfume; FCC /food chemicals codex/.
Grade or purity: 95-99+%
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Solvent
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Acetic acid, 2-methylpropyl ester: ACTIVE
In public use since the 1920s. Use in fragrances in the US amounts to approximately 5000 lb/yr
Anwendungen
BeschreibungIsobutyl 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.
OccurrenceReported 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.
VerwendenIsobutyl 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.
Darstellung
synthetischeBy direct esterification of isobutyl alcohol with acetic acid.
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Vorgelagerte Rohstoffe
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Ergänzende Hinweise
DefinitionChEBI: The acetate ester of isobutanol.
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