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Butylbenzoat

Butyl Benzoate

HCID 8698
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Grundinformationen

CAS
136-60-7
Standard-SMILES
CCCCOC(=O)c1ccccc1
InChIKey
XSIFPSYPOVKYCO-UHFFFAOYSA-N
Summenformel
C11H14O2
Durchschnittliche Molmasse
178,23 g/mol
Monoisotopische Masse
178,09937969

Überblick

Butyl benzoate is a benzoate ester obtained by condensation of benzoic acid and butanol. It is used as a perfume ingredient and as a solvent for cellulose ether, a dye carrier for textiles. It has a role as a fragrance, an antimicrobial food preservative and a plant metabolite.

Namen und Bezeichner

Bevorzugter Name
Butyl Benzoate
IUPAC
butyl benzoate
Lokaler Name
Butylbenzoat
Englischer Name
Butyl benzoate
Summenformel
C11H14O2
Molmasse
178.23

Namen und Synonyme

BUTYL BENZOATEn-Butyl benzoateBenzoic acid, butyl esterAnthrapole AZDai Cari XBNBenzoic acid n-butyl esterButylester kyseliny benzooveHSDB 2089Marvanol Carrier BB1TGZ0D0O8INSC 8474EINECS 205-252-7
Weitere Namen anzeigen
n-ButylTGIFEMA 8752AI3-00521daicarixbnanthrapoleazButylbenzoat
DTXSID8040694UNII-1TGZ0D0O8INSC-8474Butyl ester of benzoic acidButylester kyseliny benzoove [Czech]Hipochem B-3-MBRN 1867073DTXCID6020694

Datenbank-Bezeichner

CAS
136-60-7
PubChem CID
8698
DTXSID
DTXSID8040694
ChEMBL
CHEMBL1868953
ChEBI
CHEBI:156070
UNII
1TGZ0D0O8I
EC Number
205-252-7
Nikkaji
J2.019B

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3,8
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
13
Formalladung
0
Komplexität
148

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Benzoic Acid Derivatives
Cosmetics · 2 Einträge

Cosmetic ingredients (Butyl Benzoate) -> CIR (Cosmetic Ingredient Review)

Preservative

SpringerMaterials PropertiesAngular frequency
FragrancesFragrance Ingredient (Butyl benzoate) -> IFRA transparency List
LogP3.68
OdorMILD ODOR
Density1.00 @ 20 °C
Flavoring AgentsEU Flavoring substances
Color/Form · 2 Einträge

THICK, OILY LIQUID

COLORLESS LIQUID

Solubility · 4 Einträge

PRACTICALLY INSOL IN WATER

SOL IN ALCOHOL, ETHER AND ACETONE

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 38.5% (209 of 543) of reports.

Warning

H302 (16.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 543 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Benzoic acid, butyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzoic acid, butyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, butyl 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: 12-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27541

Butyl benzoate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzoic acid, butyl ester: Human health tier I assessment
Fire PotentialLow, when exposed to heat or flame.
Hazards SummaryNo rats died after exposure to saturated vapor for 8 hours; [HSDB] Oral LD50 (rat) = 5140 mg/kg; [Merck Index] Oral LD50 (rat) = 735 mg/kg; [RTECS]
FDA RequirementsButyl benzoate is an indirect food additive for use only as a component of adhesives.

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Butyl Benzoate

Used as a dye carrier in polyester fibers; [Ullmann] Used as a plasticizer; as dye carrier for polyester fibers; as additive in disinfectants; as penetrating agent in pesticide formulations; as additive in fermentation of soy sauce; as solvent for cellulose ether; as perfume ingredient; in food industry; in entomology; in the lacquer industry; Patent for use as selective yellow jacket attractant; Naturally occurring in palm, papaya, and babaco fruit and in green peas; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

USED IN THE LACQUER INDUSTRY TO A SLIGHT EXTENT; AS A PLASTICIZER

DYE CARRIER IN THE DYEING OF POLYESTER FIBERS; ADDITIVE IN DISINFECTANTS; PENETRATING AGENT IN PESTICIDE FORMULATIONS; ADDITIVE IN FERMENTATION OF SOY SAUCE

SOLVENT FOR CELLULOSE ETHER; PERFUME INGREDIENT

U.S. Production · 3 Einträge

2023: 550,000 - <1,000,000 lb

(1972) 2.53X10+9 GRAMS

(1975) 1.4X10+9 GRAMS

Consumer UsesDye
Industry UsesPlasticizer
Methods of ManufacturingESTERIFICATION OF BENZOIC ACID WITH 1-BUTANOL
Formulations/Preparations · 2 Einträge

GRADES: TECHNICAL.

It shows a purity of not less than 98%.

Use Classification · 2 Einträge

Fragrance Ingredients

Cosmetics -> Preservative

General Manufacturing Information · 3 Einträge

Synthetic Rubber Manufacturing

Benzoic acid, butyl ester: ACTIVE

A GOOD SOLVENT FOR ESTER GUM, COPAL ESTER, CUMARONE, BUT A POOR SOLVENT FOR CELLULOSE NITRATE & ACETATE, SHELLAC & COPALS, & NOT FOR GLYCERYL PHTHALATE RESINS.

Zugehörige Reaktionen

9
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 358233
HRID 358233als Eduktuspto-grants-1984_08
Reaktionsgleichung von HRID 884314
HRID 884314als Eduktuspto-grants-2012_08
Reaktionsgleichung von HRID 884315
HRID 884315als Eduktuspto-grants-2012_08
Reaktionsgleichung von HRID 884316
HRID 884316als Eduktuspto-grants-2012_08
Reaktionsgleichung von HRID 884317
HRID 884317als Eduktuspto-grants-2012_08
Reaktionsgleichung von HRID 884318
HRID 884318als Eduktuspto-grants-2012_08
Reaktionsgleichung von HRID 1045247
HRID 1045247als Eduktuspto-grants-2013_10
Reaktionsgleichung von HRID 1174423
HRID 1174423als Eduktuspto-grants-2010_11
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MISCIBLE WITH OILS AND HYDROCARBONS

Water solubility of 59 mg/l.

Flash Point225 °F (107 °C) (OPEN CUP)
Boiling Point250 °C

Physikochemische Eigenschaften

Schmelzpunkt
-22 °C · -22 °C
Siedepunkt
249 °C · 249 °C (lit.)
Dichte
1.01 g/mL · 1.01 g/mL at 25 °C (lit.)
Dampfdruck
8.5 Pa · 8.5Pa at 20℃
Brechungsindex
20 · n20/D 1.498(lit.)
Flammpunkt
223 °F · 223 °F
storage temp.
room temp
Löslichkeit
0.06 g/l · 0.06g/l
Aggregatzustand
Oily Liquid
Farbe
Clear yellow
Geruch (Odor)
100 % · at 100.00 %. mild amber balsam fruity
Geruchsart
balsamic
Wasserlöslichkeit
34.1 mg/L · 34.1mg/L at 20℃
Merck
14 · 14,1552
BRN
1867073 · 1867073
Henry's Law Constant
2.5 · 2.5×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Kosmetik-Inhaltsstoffe Funktionen
FRAGRANCEPRESERVATIVE
InChI
1S/C11H14O2/c1-2-3-9-13-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3
InChIKey
XSIFPSYPOVKYCO-UHFFFAOYSA-N
SMILES
CCCCOC(=O)c1ccccc1
LogP
3.3 · 3.3
CAS Datenbank
136 · 136-60-7(CAS DataBase Reference)
NIST chemische Informationen
Benzoic acid, butyl ester(136-60-7)
EPA chemische Informationen
Butyl benzoate (136-60-7)
NFPA Hazard Classification · 3 Einträge

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and CategoriesAcute Tox. 4 (16.6%)
Hazardous Reactivities and IncompatibilitiesCan react with oxidizing materials.

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresCarbon dioxide, dry chemical, water mist, fog, spray.
Storage Conditions... STORED IN PLACES THAT ARE COOL ENOUGH TO PREVENT ACCIDENTAL IGNITION ... PROVIDE ADEQUATE VENTILATION ... LOCATE ... STORAGE AREA WELL AWAY FROM AREAS OF FIRE HAZARD ... MUST BE KEPT APART FROM POWERFUL OXIDIZING AGENTS ... .

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Biodegradation is expected to be the major degradation process in soil. Two biodegradation screening studies have found butyl benzoate to be readily biodegradable(1-2). A measured Koc value of 125(3) suggests that butyl benzoate will be mobile in soil. Its detection in environmental ground waters(4) indicates that it can leach(SRC).

AQUATIC FATE: Biodegradation is expected to be the major degradation process in natural water. Two biodegradation screening studies have found butyl benzoate to be readily biodegradable(1-2). Some volatilization may occur. The volatilization half-lives from a model environmental river (1 meter deep) and model pond have been estimated to be 33 hours and 20 days, respectively(3,4). Aquatic bioconcentration and adsorption to sediment are not expected to be important fate processes(SRC).

ATMOSPHERIC FATE: Based upon an extrapolated vapor pressure of 0.01 mm Hg at 25 °C(1), butyl benzoate is expected to exist almost entirely in the vapor-phase in the ambient atmosphere(2). It will degrade in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals (estimated half-life of about 3.25 days)(3,SRC).

Food Survey Values · 1 Eintrag

Butyl benzoate has been identified as a volatile component of dalieb fruit (edible fruit of a palm tree that grows along the Nile River)(1). Butyl benzoate has been identified as a volatile component of papaya fruit, babaco fruit and green peas(2-4). It has been identified in molasses aroma(5).

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Plant Concentrations · 1 Eintrag

Butyl benzoate has been identified as a volatile component of dalieb fruit (edible fruit of a palm tree that grows along the Nile River)(1). Butyl benzoate has been identified as a volatile component of papaya fruit, babaco fruit and green peas(2-4).

Effluent ConcentrationsButyl benzoate was qualitatively detected in water samples collected from advanced waste treatment facilities in Lake Tahoe, CA (Oct 24, 1974), Orange County, CA (Jan-Feb, 1976), and Blue Plains, Washington DC (Sep 20, 1974)(1).
Soil Adsorption/MobilityA Koc of 125 was experimentally determined for butyl benzoate(1); this Koc value indicates high soil mobility(2).
Natural Pollution Sources · 1 Eintrag

Butyl benzoate has been identified as a volatile component of dalieb fruit (edible fruit of a palm tree that grows along the Nile River)(1). Butyl benzoate has been identified as a volatile component of papaya fruit, babaco fruit and green peas(2-4).

Human Toxicity ExcerptsBenzoic acid and its derivatives, used as preservatives in food, have been associated with urticaria. /Benzoic acid and its derivatives; from table/
Artificial Pollution SourcesButyl benzoate is commonly used as a dye carrier during textile dyeing operations and is released in the wastewaters that result from dyeing operation(1-2).
Environmental Biodegradation · 1 Eintrag

Using an aerobic dilution method and an adapted culture taken from a treatment plant, 50 ppm butyl benzoate was observed to biodegrade readily as 100% of added butyl benzoate degraded within one day(1). Using the standard BOD dilution method, butyl benzoate was found to have a 5-day theoretical BOD of 50% and a 30-day theoretical BOD of 73%(2).

Environmental Bioconcentration · 1 Eintrag

Based upon a reported water solubility of 59 mg/L(1), the BCF for butyl benzoate can be estimated to be 62 from a recommended regression-derived equation(2,SRC). This BCF value suggests that bioconcentration in aquatic organisms is not important(SRC).

Volatilization from Water/Soil · 1 Eintrag

Based upon a water solubility of 59 mg/L(1) and an extrapolated vapor pressure of 0.01 mm Hg at 25 °C(2), the Henry's Law constant for butyl benzoate can be estimated to be 3.97X10-5 atm cu m/mole; a Henry's Law constant of this magnitude indicates that volatilization from environmental waters is possible, but should not be rapid(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 33 hours(3,SRC). Volatilization half-life from an model environmental pond (2 meters deep) can be estimated to be about 20 days(4,SRC).

Regulatorische Informationen

FDA RequirementsButyl benzoate is an indirect food additive for use only as a component of adhesives.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
hs_code
29163100
RTECS-Nr.
DG4925000
risk_code
22-36/37/38
Toxizität
LD50 orally in rats: 5.14 g/kg (Smyth)
hazard_code
Xn,Xi
safety_code
26-36
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
136-60-7(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2
Anwendungen · 1 Eintrag

VerwendenButyl benzoate is used as a solvent for cellulose ether, a dye carrier for textiles, and a perfume ingredient . It occurs naturally as a volatile component of various fruits and vegetables. It has been approved by the FDA as an indirect food additive for use as a component of adhesives.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Tetrachlormethan1-Butanol, 4-bromo-, 1-benzoateCarbamic acid, N-benzoyl-N-(phenylmethyl)-, 1,1-dimethylethyl esterButoxy(tert-butyl)dimethylsilane4-Iodobutyl benzoate2,2,2-trichloroacetophenoneValerophenonPhenylvalerat

Nachgelagerte Produkte

Butyl-2-[[3-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-hydroxy-1-naphthyl]azo]benzoat6-Methyluracil
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Butyl benzoate is a benzoate ester obtained by condensation of benzoic acid and butanol. It is used as a perfume ingredient and as a solvent for cellulose ether, a dye carrier for textiles. It has a role as an antimicrobial food preservative, a fragrance and a plant metabolite.