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Butyllactat
FEMA 2205 · N-BUTYL LACTATE · BUTYL 2-HYDROXYPROPANOATE · 2-Propanoic Acid · Propanoicacid,2-hydroxy-,butylester · BUTYL LACTATE · ButylLactate>butyl DL-lactate · Lactic acid butyl
Identifikatoren & physikalische Daten
| CAS No. | 138-22-7 |
|---|---|
| Summenformel | C7H14O3 |
| Durchschnittliche Molmasse | 146,18 g/mol |
| Monoisotopische Masse | 146,09429431 g/mol |
| SMILES | CCCCOC(=O)C(C)O |
| InChIKey | MRABAEUHTLLEML-UHFFFAOYSA-N |
| PubChem CID | 8738 |
| ChEMBL | CHEMBL3183988 |
| ChEBI | CHEBI:169137 |
| EC No. | 205-316-4 |
| DTXSID | DTXSID7042196 |
| Lokaler Name | Butyllactat |
Chemische & physikalische Eigenschaften
| XLogP | 1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 101 |
| Stoffklassen | Flammable agents - 2nd degree |
| Solvents | Solvents -> Esters (<C12) |
| Kosmetika | Cosmetic ingredients (Butyl Lactate) -> CIR (Cosmetic Ingredient Review)Solvent |
| Duftstoffe | Fragrance Ingredient (Butyl lactate) -> IFRA transparency List |
| Geruch | Mild, transient odor |
| Lebensmittelzusatzstoffe | FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.98 (USCG, 1999) - Less dense than waterwill float0.9744 g/cu cm at 27 °C0.974-0.9840.984 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Water-white, stable liquidClear, colorless to white liquid |
| Löslichkeit | Slight (NIOSH, 2024)Miscible with many lacquer solvents, diluents, oils, slightly soluble in waterVery soluble in ethyl ether, ethanolIn water, 3.846X10+4 mg/L at 20 °C40 mg/mL at 20 °Cslightly soluble in watersoluble in organic solvents, oils42 g/L (25 ºC) |
| Flammpunkt | 160 °F (USCG, 1999)160 °F (closed cup)157 °F |
| Siedepunkt | 370 °F at 760 mmHg (USCG, 1999)77 °C at 10 mm Hg186.00 °C. @ 760.00 mm Hg185-187 °C76 °C (6 mm Hg)185-187 °C (lit.) |
| Schmelzpunkt | -28 °C (lit.) |
| Dampfdichte | 5.04 (vs air) |
| Dampfdruck | 0.4 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.421(lit.) |
| FEMA | 2205 | BUTYL LACTATE |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 13.06±0.20(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| Geruch | at 100.00 %. green fruity apple kiwi melon rind lactonic waxy winey apple skin soapy |
| Geruchsart | green |
| JECFA Number | 932 |
| Henry-Konstante | 4.9×100 mol/(m3Pa) at 25℃, HSDB (2015) |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCESOLVENT |
| InChI | 1S/C7H14O3/c1-3-4-5-10-7(9)6(2)8/h6,8H,3-5H2,1-2H3 |
| InChIKey | MRABAEUHTLLEML-UHFFFAOYSA-N |
| SMILES | CCCCOC(=O)C(C)O |
| LogP (Verteilungskoeffizient) | 0.88 |
| CAS Datenbank | 138-22-7(CAS DataBase Reference) |
| NIST chemische Informationen | Propanoic acid, 2-hydroxy-, butyl ester(138-22-7) |
| EPA chemische Informationen | n-Butyl lactate (138-22-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.3% (5 of 1950) of reports.DangerH315 (98.7%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 1950 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Propanoic acid, 2-hydroxy-, butyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Propanoic acid, 2-hydroxy-, butyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanoic acid, 2-hydroxy-, 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)n-Butyl lactate: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Propanoic acid, 2-hydroxy-, butyl ester: Human health tier I assessment |
| DOT-Kennzeichnung | Combustible Liquid |
| Brandgefahren | Combustible. Extinguish with dry chemical, CO2, or alcohol foam. Use water spray to "knock down" vapors and cool exposed containers. (USCG, 1999) |
| Brandpotenzial | Flammable when exposed to heat or flame |
| Gesundheitsgefahren | VAPOR: Headache, coughing, possible sleepiness, nausea or vomiting, or dizziness may result. LIQUID: Irritating to skin and eyes. (USCG, 1999) |
| Gefahrenübersicht | Workers exposed to n-butyl lactate complained of headaches and drowsiness. [ACGIH] Liquid is irritating to the skin and eyes. [CAMEO] |
| DOT-Nummer und Handbuch | 1993 128(combustible liquid, n.o.s.) |
| Reaktive Gruppe | Alcohols and Polyols |
| FIFRA-Anforderungen | Unless specifically excluded, residues resulting from the use of the following substances as either an inert or an active ingredient in a pesticide chemical formulation, including antimicrobial pesticide chemicals, are exempted from the requirement of a tolerance under /Federal food, Drug, and Cosmetic Act/ (FFDCA) section 408, if such use is in accordance with good agricultural or manufacturing practices. Lactic acid, n-butyl ester is included on this list. |
| Reactivity Profile | BUTYL LACTATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Avoid contact with strong oxidizing agents and strong bases. Will not polymerize (USCG, 1999). |
| Flammable Limits | Class IIIA Combustible Liquid: Fl.P. at or above 140 °F and below 200 °F. |
| Brandbekämpfung | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| Erste Hilfe | Excerpt from NIOSH Pocket Guide for n-Butyl lactate:(General first aid procedures) |
| Brandbekämpfungsverfahren | Extinguishing methods: Alcohol FoamIf 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 be ineffective. 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.Use alcohol foam, foam, carbon dioxide, dry chemical.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. |
| Reinigungsverfahren | Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.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. |
| Preventive Measures | Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors.Work clothing that becomes wet or significantly contaminated should be removed and replaced.For more Preventive Measures (Complete) data for n-Butyl lactate (8 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| Allowable Tolerances | Unless specifically excluded, residues resulting from the use of the following substances as either an inert or an active ingredient in a pesticide chemical formulation, including antimicrobial pesticide chemicals, are exempted from the requirement of a tolerance under FFDCA section 408, if such use is in accordance with good agricultural or manufacturing practices. Lactic acid, n-butyl ester is included on this list. |
| Respirator Recommendations | Important additional information about respirator selection |
| Threshold Limit Values (TLV) | 5.0 [ppm]8 hr Time Weighted Avg (TWA): 5 ppmExcursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.5 ppm [1973] |
| Körperbelastung | n-Butyl lactate was detected in expired air at a rate of 3.4 ug/hr of 1 of 8 male subjects, median age of 38(1). |
| Zielorgane | Eyes, skin, respiratory system, central nervous system |
| Ökotoxizitätswerte | EC50Species: Pseudokirchneriella subcapitata (Green Algae, 1x10+4 cells/mL)Conditions: freshwater, static, 20 °C, pH 8.0Concentration: 329000 ug/L for 72-96 hrEffect: decreased population biomass /formulation, 97% purity/Concentration: 929000 ug/L for 72-96 hr (95% confidence interval: 881000-980000 ug/L)Effect: decreased population growth rate /formulation, 97% purity/Species: Daphnia magna (Water Flea)Conditions: freshwater, staticConcentration: 320000 ug/L for 48 hr (95% confidence interval: 320000-399000 ug/L)Effect: intoxication, decreased mobility /formulation, 97% purity/LC50Species: Danio rerio (Zebra Danio)Concentration: 75000 ug/L for 96 hr (95% confidence interval: 56000-10000 ug/L) /formulation, 97% purity/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that n-butyl lactate is expected to have very high mobility in soil(SRC). Volatilization of n-butyl lactate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 0.40 mm Hg(3), and water solubility, 3.846X10+4 mg/L(4). n-Butyl lactate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Using the Closed Bottle test, n-butyl lacate exhibited 22-39% degradation in 5 days(5), suggesting that biodegradation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that n-butyl lactate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.0X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.40 mm Hg(4), and water solubility, 3.846X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 23 and 170 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.80(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using the Closed Bottle test, n-butyl lacate exhibited 22-39% degradation in 5 days(9), suggesting that biodegradation may be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyl lactate, which has a vapor pressure of 0.4 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyl lactate 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 1.5 days(SRC), calculated from its rate constant of 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). n-Butyl lactate 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). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | inhalation, ingestion, skin and/or eye contact |
| Toxizitätsübersicht | Based on the available information included in this report, the CIR Expert Panel concludes that Glycolic and Lactic Acid, their common salts and their simple esters, are safe for use in cosmetic products at concentrations less than or equal to 10%, at final formulation pH greater than or equal to 3.5, when formulated to avoid increasing sun sensitivity or when directions for use include the daily use of sun protection. These ingredients are safe for use in salon products at concentrations less than or equal to 30%, at final formulation pH greater than or equal to 3.0, in products designed for brief, discontinuous use followed by thorough rinsing from the skin, when applied by trained professionals, and when application is accompanied by directions for the daily use of sun protection...Butyl Lactate...Safe for use in cosmetics, with qualifications |
| Signs and Symptoms | irritation eyes, skin, nose, throatdrowsiness, headache, central nervous system depressionnausea, vomiting |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of n-butyl lactate can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that n-butyl lactate is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Prolonged exposures to n-butyl lactate at concentrations of approx. 7 ppm with short, peak exposures of 11 ppm resulted in headache and irritation of the pharyngeal and laryngeal mucosa, with coughing, in all workers. Some workers complained of sleepiness and headache in the evening after workoccasional nausea and vomiting were experienced. Complaints of irritation of the conjunctiva were not confirmed by examination. Routine blood and urine clinical analyses were normal. Some symptoms of exposure (headache, coughing, pharyngitis) were related to air concentrations of 4 ppm measured with a personal monitoring device. However, when exposure concentrations were below 1.4 ppm, no signs or symptoms of butyl lactate exposure occurred, and medical examinations were negative. |
| Artificial Pollution Sources | n-Butyl lactate's production and use as a solvent for nitrocellulose, ethyl cellulose, oils, dyes, natural gums, many synthetic polymers, lacquers, varnishes, inks, stencil pastes, antiskinning agent, chemical (intermediate), perfumes, dry-cleaning fluids, and adhesives(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: n-Butyl lactate, present at 1.53, 2.0 and 2.08 mg/L, exhibited degradation of 22, 39, and 25%, respectively, in 5 days using an activated sludge inoculum in the Closed Bottle test. The percent degradation was 57, 63 and 69 after 28, 20 and 28 days respectively(1). |
| Berufliche Expositionsstufe (OEB) | A |
| Arbeitsplatzgrenzwert (OEL) | TWA: 5 ppm (25 mg/m3) |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29155090 |
| RTECS-Nr. | OD4025000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-37/39 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 138-22-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Reported found in cognac, cider and white wine.
Verwenden
n-Butyl lactate is used as a food and feed additive.
Herstellung & Synthese
synthetische
The racemic d-form is prepared by reacting zinc ammonium l-lactate with n-butyl alcohol in the presence of concentrated H2SO4; the l-form is prepared by reacting zinc ammonium d-lactate with n-butyl alcohol in the presence of HCl; the racemic form is prepared by several methods, one being from calcium or sodium lactate and n-butyl alcohol in benzene in the presence of H2SO4, with subsequent azeotropic distillation of the mixture.