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2-Ethylhexan-1-ol
2-ETHYL-1-HEXANOL · OCTANOL · 2-Ethylhexan-1-ol · 2EH · ISOOCTYL ALCOHOL · ISOOCTANOL · Ethylhexanol · 1-hexanol,2-ethyl-
Identifikatoren & physikalische Daten
| CAS No. | 104-76-7 |
|---|---|
| Summenformel | C8H18O |
| Durchschnittliche Molmasse | 130,23 g/mol |
| Monoisotopische Masse | 130,1357652 g/mol |
| SMILES | CCCCC(CC)CO |
| InChIKey | YIWUKEYIRIRTPP-UHFFFAOYSA-N |
| PubChem CID | 7720 |
| ChEMBL | CHEMBL31637 |
| ChEBI | CHEBI:16011 |
| EC No. | 203-234-3 |
| DTXSID | DTXSID5020605 |
| Lokaler Name | 2-Ethylhexan-1-ol |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 52,5 |
| Stoffklassen | PhthalateVolatile Organic Compound (VOC) |
| Lipide | Fatty Acyls [FA] -> Fatty alcohols [FA05] |
| Solvents | Solvents -> Alcohols (<C12) |
| Duftstoffe | Fragrance Ingredient (2-Ethyl-1-hexanol) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 2.3-3.1 |
| Geruch | Mild, oily, sweet, slightly floral odor reminiscent of roseIntense and unpleasant |
| Geschmack | Sweet, fatty-floral taste with fruital noteIntense and unpleasant |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.834 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8344 at 20 °C/20 °CBulk density: 6.9 lb/gal at 20 °C% IN SATURATED AIR: 0.0066 @ 20 °CDENSITY OF "SATURATED" AIR: LESS THAN 1.001 (AIR= 1)Relative density (water = 1): 0.830.830-0.8340.833 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 9.8 centapoise at 20 °C12,0 mm²/s at 20 °C |
| Color/Form | Colorless liquid |
| Schmelzpunkt | −76 °C(lit.) |
| Siedepunkt | 183-186 °C(lit.) |
| Dampfdichte | 4.49 (vs air) |
| Dampfdruck | 0.2 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.431(lit.) |
| FEMA | 3151 | 2-ETHYL-1-HEXANOL |
| Flammpunkt | 171 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Water1 g/L (20 ºC) |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 15.05±0.10(Predicted) |
| Farbe | Clear |
| pH | 7 (1g/l, H2O, 20℃) |
| Geruch | sweet. |
| Biologische Quelle | synthetic |
| Geruchsschwelle | 0.013ppm |
| Geruchsart | citrus |
| Explosionsgrenze | 0.88%, 104°F |
| Spezifische Wärmekapazität | Cp(liquid): 2.44 J/(g·K), at 25℃ |
| Merck | 14,3808 |
| JECFA Number | 267 |
| BRN | 1719280 |
| Henry-Konstante | 4.6×10-1 mol/(m3Pa) at 25℃, Plyasunov and Shock (2000) |
| Dielektrizitätskonstante | 3.4(18℃) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong acids. |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 |
| InChIKey | YIWUKEYIRIRTPP-UHFFFAOYSA-N |
| SMILES | CCCCC(CC)CO |
| LogP (Verteilungskoeffizient) | 2.9 at 25℃ |
| CAS Datenbank | 104-76-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Hexanol, 2-ethyl-(104-76-7) |
| EPA chemische Informationen | 2-Ethylhexanol (104-76-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.7% (26 of 3744) of reports.WarningH315 (88.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3744 reports by companies from 58 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard] |
|---|---|
| Regulatorische Informationen | Chemical: 1-Hexanol, 2-ethyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)1-Hexanol, 2-ethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Hexanol, 2-ethyl- 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: 31-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/151941-Hexanol, 2-ethyl-: HSNO Approval: HSR001386 Approved with controls |
| Weitere Sicherheitsinformationen | IMAP assessments - 1-Hexanol, 2-ethyl-: Human health tier II assessment |
| DOT-Kennzeichnung | Flammable Liquid Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Above 73 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | 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. |
| Gesundheitsgefahren | Anesthesia, nausea, headache, dizzinessmildly irritating to skin and eyes. (USCG, 1999) |
| Gefahrenübersicht | A skin, eye, and respiratory tract irritantInhalation of high concentrations may cause CNS effects[ICSC] An irritantMay cause severe injury to eyesEffects in high-dose animal studies include degenerative changes to brain[MSDSonline] |
| Reaktive Gruppe | Alcohols and Polyols |
| Special Reports | WHOEnviron Health Criteria Number 32: Toxicological Evaluation of Certain Food Additives and Contaminants. (1993) |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Ethyl-1-hexanol is included on this list. Effective date: 6/1/87Sunset date: 12/19/95. |
| FIFRA-Anforderungen | Residues of 2-ethyl-1-hexanol are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: Solvent, adjuvant of surfactants. Limit: Not more than 10% of pesticide.Residues of 2-ethyl-1-hexanol are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. Use: Solvent, adjuvant of surfactants. Limit: Not more than 10% of pesticide. |
| Reactivity Profile | 2-ETHYL HEXANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. This compound is incompatible with strong oxidizing agents and strong acids. (NTP, 1992) |
| Brandbekämpfung | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:Use water spray, alcohol-resistant foam, dry powder, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | 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. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Sichere Lagerung | Separated from strong oxidants and strong bases. Store in an area without drain or sewer access. Ventilation along the floor. |
| Firefighting Hazards | A dangerous fire hazard when exposed to heat or flamecan react vigorously with oxidizing materials. |
| Expositionsschutz und Persönliche Schutzausrüstung | 10.0 [ppm] |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Use water spray to cool unopened containers.Wear self contained breathing apparatus for fire fighting if necessary.To fight fire, use foam, carbon dioxide, dry chemical. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. |
| Reinigungsverfahren | Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.Contain spillage, and then collects with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulation ... Keep in sutable, closed containers for disposal.Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. |
| Freisetung ohne Brand | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: |
| Entsorgungsverfahren | Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material.Contaminated packaging: Dispose of as unused product.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. |
| Verschüttetes entsorgen | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Körperbelastung | 2-Ethylhexanol was detected in 17.6% of 387 samples of expired air from 54 study subjects selected from urban areas who were normal, healthy and nonsmokingthe geometric mean concentration was 4 ng/L of expired air at 25 °C(1). 2-Ethylhexanol was not detected in twelve breath samples from subjects in Bayonne, NJ(2). 2-Ethylhexanol was found in 1 of 8 samples (Pittsburgh, Pa) of mother's milk collected from various US cities(3). In a national study in fiscal year 1982, 2-ethylhexanol was found in 7 of 46 composite samples of adipose tissue(4). The age distribution of positive composites was (age, fraction positive samples): 0-14, 1/1215-44, 4/1745+, 2/17(4).the geometric mean concn was 4 ng/L of expired air at 25 °C(1). It was not detected in twelve breath samples from subjects in Bayonne, NJ(3). 2-Ethylhexanol was found in 1 of 8 samples (Pittsburgh, Pa) of mother's milk collected from various US cities(2). In a national study in FY 82, 2-ethylhexanol was found in 7 of 46 composite samples of adipose tissue(4). The age distribution of positive composites was (age, fraction positive samples): 0-14, 1/1245+, 2/17. |
| Wechselwirkungen | Pregnant Wistar rats were admin undiluted di(2-ethylhexyl)phthalate (DEHP12.5 or 25 mmol/kg bw), 2-ethyl-1-hexanol (6.25 or 12.5 mmol/kg bw, approx equivalent to 800 and 1600 mg/kg bw), or 2-ethylhexanoic acid (EA6.25 or 12.5 mmol/kg bw) by gavage on day 12 of gestation. Control rats were not gavaged (untreated controls). Caffeine (150 mg/kg) was dissolved in water and injected ip in some pregnant rats of each group. Rats were killed on day 20 of gestationfollowing Caesarean section, implantation sites were determined in situ and the number of dead or resorbed fetuses was determined. Live fetuses were removed and examinedinternal and external soft tissue and skeletal malformations were recorded. At least seven litters for each experimental condition were analyzed. Administration of each test compound resulted in statistically significant, dose-related increases in malformed live fetuses ... 2-ethyl-1-hexanol: 6.25 mmol/kg bw (7 litters) - 2.0 + or - 1.3%, 12.5 mmol/kg bw (7 litters) - 22.2 + or - 14.7% ... compared to controls (no malformed live fetuses in 7 litters). Defects in fetuses following treatment with 2-ethyl-1-hexanol included hydronephrosis (7.8% of live fetuses), tail defects (4.9% of live fetuses), limb defects (9.7% of live fetuses), and other defects (1.0% of live fetuses). For each test compound, caffeine was reported to potentiate (increase) the percent of malformed live fetuses. However, administration of test compounds did not significantly affect the percentage of dead and resorbed fetuses compared to controls. No maternal effects associated with the test compounds were reported ... . |
| Ökotoxizitätswerte | EC50Species: Chlorococcales (Green Algae Order)Conditions: freshwater, staticConcentration: 130000 ug/L for 24 hrEffect: physiology, assimilation efficiencyLC50Species: Artemia salina (Brine Shrimp) naupliiConditions: saltwater, static, 24 °CConcentration: 19000 ug/L for 24 hrSpecies: Lepomis macrochirus (Bluegill) weight 0.1 gConditions: freshwater, static, 20 °C, pH 7.4, hardness 272 mg/L CaCO3Concentration: 10000 ug/L for 24 hr (95% confidence interval: 10000-33000 ug/L) /100% purity technical material/Concentration: 10000 ug/L for 96 hr (95% confidence interval: 10000-33000 ug/L) /100% purity technical material/For more Ecotoxicity Values (Complete) data for 2-ETHYL-1-HEXANOL (8 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 35(SRC), determined from a structure estimation method(2), indicates that 2-ethylhexanol is expected to have very high mobility in soil(SRC). Volatilization of 2-ethylhexanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 0.136 mm Hg(3), and water solubility, 880 mg/L(4). 2-Ethylhexanol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Based on 31, 52, and 5% biodegradation when incubated for 21 days in soil from a waste disposal site, in soil amended with nitrogen, and in soil incubated under anaerobic conditions, respectively(5), biodegradation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 35(SRC), determined from a structure estimation method(2), indicates that 2-ethylhexanol 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 2.6X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.136 mm Hg(4), and water solubility, 880 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 41 hours and 16 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 30(SRC), from an estimated log Kow of 2.73(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using river water incubated at 18-19 °C, 59% biodegradation after 9 days(11) suggests that biodegradation may be an important enviornmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-ethylhexanol, which has a vapor pressure of 0.136 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-ethylhexanol 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 26 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Ethylhexanol 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). |
| Lebensmitteluntersuchungswerte | 2-Ethylhexanol is a volatile found in fruits, such as cassava(1), apricots(2), plums(2), apples(3), and nectarines(4). 2-Ethylhexanol was detected in raw and roasted earth almonds (Cyperus esculentus L)(5). It is also a meat flavor volatile and has been identified in raw beef(6), duck meat(7), frankfurters(8) and fried bacon(9). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour, by ingestion and through the skin. |
| Milk Concentrations | 2-Ethylhexanol was detected in 1 (Pittsburgh, PA) of 8 samples of mother's milk analyzed from US cites(1). |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Earlier work with pure cultures had shown that the interaction of microbes with plasticizers leads to the formation of metabolites including 2-ethylhexanoic acid and 2-ethylhexanol that resist further degradation... These compounds have been shown to exhibit acute toxicity using Microtox, Daphnia, rainbow trout and fathead minnow toxicity assays. Since it is already well established that plasticizers are ubiquitous in the environment, it is expected that their recalcitrant metabolites will also be ubiquitous. This is of concern because, while the plasticizers do not exhibit acute toxicity, their metabolites do. |
| Plant Concentrations | 2-Ethyl-1-hexanol was detected in shoot samples of Marginatus (Plectranthus coleoides) /White-edged Swedish Ivy/ at a concentration range of 0-36 ppm(1).2-Ethylhexanol is a plant volatile which has been identified in cassava(1), apricots(2), plums(2), apples(3), and nectarines(4). The amount of 2-ethylhexanol emitted from immature apples is not substantially different from that emitted from apples at different post-harvest periods(3). 2-Ethylhexanol was detected, not quantified, in whole and ground musty sorghum(5). |
| Signs and Symptoms | Cough. Dizziness. Headache. Sore throat. Weakness.Redness. Dry skin.Redness. Pain. Blurred vision.Nausea. Further see Inhalation. |
| Acute Toxicity Link | Chemical: 2-ETHYLHEXANOL |
| Luftstandards | 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. 2-Ethylhexanol is produced, as an intermediate or a final product, by process units covered under this subpart. |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29339990 |
| RTECS-Nr. | MP0350000 |
| R-Sätze (R) | 37/38-41-36-21-52/53-36/37/38-20 |
| Toxizität | LD50 orally in Rabbit: 3730 mg/kg LD50 dermal Rat > 3000 mg/kg |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-36/39-36/37/39-36-61 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 104-76-7(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 InhalationEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Selbstentzündungstemperatur | 550 °F |
Anwendungen & Verwendung
Beschreibung
2-Ethylhexanol, also known as 2-Ethylhexan-1-ol, abbreviated as 2-EH, is a branched eight-carbon alcohol. In industry, 2-EH is mainly used to make ester plasticizers, which can be used to produce soft polyvinyl chloride. 2-EH can also be used to make a chemical used in the production of coating materials, adhesives, printing inks and impregnation agents. 2-EH occurs naturally in food and is used as a volatile flavoring agent and is indirectly approved as a food additive by the FDA. In addition, 2-EH is also used as an inert pesticide ingredient in pesticide formulations for cultivated crops, raw agricultural products (RAG) or animals.
Occurrence
Reported found in papaya, peach, pear, blackberry, strawberry, cabbage, Parmesan and mozzarella cheese, butter, roasted chicken, cognac, sherry, grape wines, tea, avocado, kiwifruit, crab and clam.
Verwenden
2-Ethylhexanol is the most important C8 alcohol and is mainly used as the alcohol component for the manufacture of ester plasticizers for soft poly(vinyl chloride) (PVC). Other minor uses include the manufacturing of 2-ethylhexyl acrylate, as a dispersing agent and wetting agent, as a solvent for gums and resins, as a cosolvent for nitrocellulose, and in ceramics, paper coatings, rubber latex, textiles, and fragrances.
Herstellung & Synthese
synthetische
2-ethylhexanol synthesis: Condensation of acetaldehyde into butanol aldehyde, dehydration to obtain crotonaldehyde, hydrogenation to n-butyraldehyde, condensation dehydration to obtain 2-ethyl-2-hexenal, and then hydrogenation to obtain 2-ethylhexanol.