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Butyllactat

Butyl Lactate

HCID 8738
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Grundinformationen

CAS
138-22-7
Standard-SMILES
CCCCOC(=O)C(C)O
InChIKey
MRABAEUHTLLEML-UHFFFAOYSA-N
Summenformel
C7H14O3
Durchschnittliche Molmasse
146,18 g/mol
Monoisotopische Masse
146,09429431

Überblick

Butyl lactate appears as a clear colorless liquid with a mild odor. Flash point 168 °F. Less dense than water and insoluble in water. Vapors heavier than air. Used as a solvent, and to make other chemicals.

Namen und Bezeichner

Bevorzugter Name
Butyl Lactate
IUPAC
butyl 2-hydroxypropanoate
Lokaler Name
Butyllactat
Englischer Name
Butyl lactate
Summenformel
C7H14O3
Molmasse
146.18

Namen und Synonyme

BUTYL LACTATEButyl 2-hydroxypropanoate138-22-7n-Butyl lactatePropanoic acid, 2-hydroxy-, butyl esterLactic acid, butyl ester2-Hydroxypropanoic acid butyl esterButylester kyseliny mlecneButyl alpha-hydroxypropionateFEMA No. 2205DTXSID70421960UI63W814U
Weitere Namen anzeigen
FEMA 22052-Propanoic AcidPropanoicacid,2-hydroxy-,butylesterButylLactate>butyl DL-lactateLactic acid butylButyl lactate 98%
NSC-6533DTXCID5022196RefChem:122266205-316-4Butyllactate(+/-)-Butyl lactateNSC 6533Butyl L-lactate

Datenbank-Bezeichner

CAS
138-22-7
PubChem CID
8738
DTXSID
DTXSID7042196
ChEMBL
CHEMBL3183988
ChEBI
CHEBI:169137

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,1
Polarare Oberfläche (TPSA)
46,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
5
Schwere Atome
10
Formalladung
0
Komplexität
101

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
SolventsSolvents -> Esters (<C12)
Cosmetics · 2 Einträge

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

Solvent

FragrancesFragrance Ingredient (Butyl lactate) -> IFRA transparency List
OdorMild, transient odor
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 5 Einträge

0.98 (USCG, 1999) - Less dense than water; will float

0.9744 g/cu cm at 27 °C

0.974-0.984

0.98

0.98

Flavoring AgentsEU Flavoring substances
Color/Form · 2 Einträge

Water-white, stable liquid

Clear, colorless to white liquid

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 · 6 Einträge

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1950) of reports.

Danger

H315 (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.

Warning

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Propanoic acid, 2-hydroxy-, butyl ester

Commission 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 standard

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.)

Other Safety InformationIMAP assessments - Propanoic acid, 2-hydroxy-, butyl ester: Human health tier I assessment
DOT LabelCombustible Liquid
Fire HazardsCombustible. Extinguish with dry chemical, CO2, or alcohol foam. Use water spray to "knock down" vapors and cool exposed containers. (USCG, 1999)

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 4 Einträge

CIR ingredient: Butyl Lactate

Used as a solvent for paints, dyes, polymers, etc.; [ACGIH]

Painting (Solvents) [Category: Paint]

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, adhesives.

U.S. Production · 2 Einträge

2023: 35,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7736]

Industry UsesFragrance
Methods of Manufacturing... Esterification of lactic acid and the respective alcohol.
Formulations/Preparations · 2 Einträge

Grade: Technical, 95% min.

The commercial grade contains condensation products and its physical and chemical properties will vary

Use Classification · 4 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Cosmetics -> Solvent

General Manufacturing Information · 2 Einträge

Not Known or Reasonably Ascertainable

Propanoic acid, 2-hydroxy-, butyl ester: ACTIVE

Anwendungen

Zugehörige Reaktionen

11
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 103352
HRID 103352als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 248612
HRID 248612als Eduktuspto-grants-1993_05
Reaktionsgleichung von HRID 493450
HRID 493450als Eduktuspto-grants-2009_05
Reaktionsgleichung von HRID 1099475
HRID 1099475als Eduktuspto-grants-2012_03
Reaktionsgleichung von HRID 1209948
HRID 1209948als EduktTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
Reaktionsgleichung von HRID 1251615
HRID 1251615als Produktals Eduktuspto-grants-2002_01
Reaktionsgleichung von HRID 1251616
HRID 1251616als Produktuspto-grants-2002_01
Reaktionsgleichung von HRID 1294050
HRID 1294050als Eduktuspto-grants-2007_07
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UNII
0UI63W814U
EC Number
205-316-4
Nikkaji
J39.933G
Solubility · 6 Einträge

Slight (NIOSH, 2024)

Miscible with many lacquer solvents, diluents, oils, slightly soluble in water

Very soluble in ethyl ether, ethanol

In water, 3.846X10+4 mg/L at 20 °C

40 mg/mL at 20 °C

slightly soluble in water; soluble in organic solvents, oils

Flash Point · 5 Einträge

160 °F (USCG, 1999)

160 °F

160 °F (closed cup)

160 °F

160 °F

Boiling Point · 6 Einträge

370 °F at 760 mmHg (USCG, 1999)

77 °C at 10 mm Hg

186.00 °C. @ 760.00 mm Hg

185-187 °C; 76 °C (6 mm Hg)

370 °F

370 °F

Physikochemische Eigenschaften

Schmelzpunkt
-28 °C · -28 °C (lit.)
Siedepunkt
185 · 185-187 °C (lit.)
Dichte
0.984 g/mL · 0.984 g/mL at 25 °C (lit.)
Dampfdichte
5.04 · 5.04 (vs air)
Dampfdruck
0.4 mm · 0.4 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.421(lit.)
FEMA
2205 · 2205 | BUTYL LACTATE
Flammpunkt
157 °F · 157 °F
storage temp.
Sealed in dry,Room Temperature
pka
13.06 · 13.06±0.20(Predicted)
Aggregatzustand
Liquid
Farbe
Clear colorless
Geruch (Odor)
100 % · at 100.00 %. green fruity apple kiwi melon rind lactonic waxy winey apple skin soapy
Geruchsart
green
Wasserlöslichkeit
42 g/L · 42 g/L (25 ºC)
JECFA Number
932 · 932
Henry's Law Constant
4.9 · 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
0.88 · 0.88
CAS Datenbank
138 · 138-22-7(CAS DataBase Reference)
NIST chemische Informationen
2 · Propanoic acid, 2-hydroxy-, butyl ester(138-22-7)
EPA chemische Informationen
n-Butyl lactate (138-22-7)
Fire PotentialFlammable when exposed to heat or flame
Health HazardsVAPOR: Headache, coughing, possible sleepiness, nausea or vomiting, or dizziness may result. LIQUID: Irritating to skin and eyes. (USCG, 1999)
Hazards SummaryWorkers exposed to n-butyl lactate complained of headaches and drowsiness. [ACGIH] Liquid is irritating to the skin and eyes. [CAMEO]
DOT ID and Guide1993 128(combustible liquid, n.o.s.)
Reactive GroupAlcohols and Polyols
FIFRA Requirements · 1 Eintrag

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 · 1 Eintrag

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 LimitsClass IIIA Combustible Liquid: Fl.P. at or above 140 °F and below 200 °F.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
First Aid · 2 Einträge

Excerpt from NIOSH Pocket Guide for n-Butyl lactate:

(General first aid procedures)

Fire Fighting Procedures · 4 Einträge

Extinguishing methods: Alcohol Foam

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 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.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.
Cleanup Methods · 1 Eintrag

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.

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 2 Einträge

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.

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 · 5 Einträge

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 EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Allowable Tolerances · 1 Eintrag

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 RecommendationsImportant additional information about respirator selection
Threshold Limit Values (TLV) · 4 Einträge

5.0 [ppm]

8 hr Time Weighted Avg (TWA): 5 ppm

Excursion 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]

Toxikologische Informationen

Body Burdenn-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).
Target OrgansEyes, skin, respiratory system, central nervous system
Ecotoxicity Values · 4 Einträge

EC50; Species: Pseudokirchneriella subcapitata (Green Algae, 1x10+4 cells/mL); Conditions: freshwater, static, 20 °C, pH 8.0; Concentration: 329000 ug/L for 72-96 hr; Effect: decreased population biomass /formulation, 97% purity/

EC50; Species: Pseudokirchneriella subcapitata (Green Algae, 1x10+4 cells/mL); Conditions: freshwater, static, 20 °C, pH 8.0; Concentration: 929000 ug/L for 72-96 hr (95% confidence interval: 881000-980000 ug/L); Effect: decreased population growth rate /formulation, 97% purity/

EC50; Species: Daphnia magna (Water Flea); Conditions: freshwater, static; Concentration: 320000 ug/L for 48 hr (95% confidence interval: 320000-399000 ug/L); Effect: intoxication, decreased mobility /formulation, 97% purity/

LC50; Species: Danio rerio (Zebra Danio); Conditions: freshwater, static; Concentration: 75000 ug/L for 96 hr (95% confidence interval: 56000-10000 ug/L) /formulation, 97% purity/

Environmental Fate · 3 Einträge

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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routesinhalation, ingestion, skin and/or eye contact
Toxicity Summary · 2 Einträge

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 Symptomsirritation eyes, skin, nose, throat; drowsiness, headache, central nervous system depression; nausea, vomiting
Soil Adsorption/Mobility · 1 Eintrag

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 · 1 Eintrag

/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 work; occasional 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 · 1 Eintrag

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 · 1 Eintrag

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).

Regulatorische Informationen

FIFRA Requirements · 1 Eintrag

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.

Sicherheitsdaten

OEB
A
OEL
TWA: 5 ppm (25 mg/m3)
wgk
2
tsca
TSCA listed
hs_code
29155090
RTECS-Nr.
OD4025000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-37/39
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
138-22-7(Hazardous Substances Data)

OccurrenceReported found in cognac, cider and white wine.

Verwendenn-Butyl lactate is used as a food and feed additive.

Darstellung · 1 Eintrag

synthetischeThe 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Zinkdilactat(3S-cis)-3,6-Dimethyl-1,4-dioxan-2,5-dion1-Butanoldextrolactic acidCalciumdilactat

Nachgelagerte Produkte

Butyl-O-butyryllactat2-Furyl-methanal