Ethylacetat Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die D?mpfe sind schwerer als Luft und k?nnen sich am Boden ausbreiten. Fernzündung m?glich.
CHEMISCHE GEFAHREN
Erhitzen kann zu sehr heftiger Verbrennung oder Explosion führen. Zersetzung unter Einfluss von UV-Licht, S?urenund Basen. Reagiert mit starken Oxidationsmitteln, Basen oder S?uren. Greift Aluminium und Kunststoffe an.
ARBEITSPLATZGRENZWERTE
TLV: 400 ppm (als TWA); (ACGIH 2005).
MAK: 400 ppm, 1500 mg/m? Spitzenbegrenzung: überschreitungsfaktor I(2); Schwangerschaft: Gruppe C; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation der D?mpfe.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitssch?dliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen und die Atemwege. M?glich sind Auswirkungen auf das Zentralnervensystem. Exposition weit oberhalb der Arbeitsplatzgrenzwerte kann zum Tod führen.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Die Flüssigkeit entfettet die Haut.
LECKAGE
Gefahrenbereich verlassen! Ausgelaufene Flüssigkeit m?glichst in abdichtbaren Beh?ltern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Kanalisation spülen. Pers?nliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabh?ngigem Atemschutzger?t.
R-S?tze Betriebsanweisung:
R11:Leichtentzündlich.
R36:Reizt die Augen.
R66:Wiederholter Kontakt kann zu spr?der oder rissiger Haut führen.
R67:D?mpfe k?nnen Schl?frigkeit und Benommenheit verursachen.
R20/21/22:Gesundheitssch?dlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R10:Entzündlich.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R68/20/21/22:Gesundheitssch?dlich: M?glichkeit irreversiblen Schadens durch Einatmen,Berührung mit der Haut und durch Verschlucken.
S-S?tze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S33:Ma?nahmen gegen elektrostatische Aufladungen treffen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S7:Beh?lter dicht geschlossen halten.
S25:Berührung mit den Augen vermeiden.
Aussehen Eigenschaften
C4H8O2; (Ethylacetat; Essigester; Essigether). Farblose, charakteristisch riechende Flüssigkeit.
Gefahren für Mensch und Umwelt
Leichtentzündlich. Die Dämpfe sind viel schwerer als Luft und bilden mit Luft explosionsfähige Gemische. Mit Oxidationsmittel heftige Reaktion, ggf. Entzündung möglich.
Ethylacetat besitzt in niedrigen Dampfkonzentrationen einen angenehm fruchtargtigen Geruch, in mittleren Konzentrationen schleimhautreizende, in höheren Dosen narkotische Wirkung. Dasselbe tritt nach Verschlucken ein, wobei geringe Dosen krampflösend und auf die Atmung vertiefend wirken. Die Symptome nach Inhalation sind: Kratzen im Hals, Appetitlosigkeit, Magenschmerzen , Kopfschmerzen. Bei höheren Konzentrationen, je nach aufgenommener Menge, subnarkotische bis narkotische Symptome, evtl.. Atemlähmung. Lungenödeme sind möglich. Durch entfettende Wirkung sind Hautekzeme möglich.
Schwach wassergefährdender Stoff (WGK 1).
Schutzma?nahmen und Verhaltensregeln
Von Zündquellen fernhalten.
Nur in gut gelüfteten Bereichen verwenden.
Schutzhandschuhe nur als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Mit saugfähigem, inertem Material z. Rench Rapid oder Chemozorb aufnehmen. Rückstände mit viel Wasser und Netzmittel wegspülen.
Wasser, Kohlendioxid, Trockenlöschmittel, Schaum.
Erste Hilfe
Nach Augenkontakt: Bei Kontakt gründlich mit Wasser (mind. 10 Min.) spülen. Augenarzt konsultieren.
Nach Einatmen: Frischluft.
Nach Verschlucken: Sofort und wiederholt reichlich Wasser trinken. Erbrechen vermeiden (Aspirationsgefahr!). Arzt aufsuchen.
Nach Kleidungskontakt: Benetzte Kleidung sofort ausziehen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Sondermüll (halogenfreie Lösungsmittel) entsorgen.
Beschreibung
Ethyl acetate (systematically, ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound with the formula CH
3COOCH
2CH
3. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, decaffeinating tea and coffee, and cigarettes (see list of additives in cigarettes). Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tons. In 2004, an estimated 1.3M tons were produced worldwide.
Chemische Eigenschaften
Ethyl acetate has a pleasant ethereal fruity, brandy-like odor, reminiscent of pineapple, somewhat nauseating in high
concentration. It has fruity sweet taste when freshly diluted in water. Ethyl acetate is probably one of the most used of all flavor
chemicals by volume. Ethyl acetate is slowly decomposed by moisture and then acquires an acid status due to the acetic acid formed.
Physikalische Eigenschaften
Clear, colorless, mobile liquid with a pleasant, sweet fruity odor. Experimentally determined
detection and recognition odor threshold concentrations were 23 mg/m
3 (6.4 ppm
v) and 48 mg/m
3
(13.3 ppm
v), respectively (Hellman and Small, 1974). Cometto-Mu?iz and Cain (1991) reported
an average nasal pungency threshold concentration of 67,300 ppm
v.
Occurrence
Although it has been reported present in some natural fruital aromas and in some distillates (rum, rum ether),
it has not been reported yet as a constituent of essential oils; it has been identified also in the petals of Magnolia fuscata. Reported
found in many foods including fresh and cooked apple, apricot, banana (169 ppm), sweet and sour cherry, citrus peel oils and juices,
blueberry, cranberry, black currants, raspberry, blackberry, guava, passion fruit, melon, peaches, papaya, pineapple, cabbage, onion,
leek, potato, tomato (3 to 6 ppm), clove, ginger, vinegar, breads, cheeses (0.2 to 0.8 ppm), butter (2 ppm), yogurt, milk, meats, cognac,
beer (4 to 64 ppm), whiskies, cider, sherry, grape wines, rum, cocoa, coffee, tea, filberts, peanuts, popcorn, oats, honey, soybeans,
coconut, olive oil (0.02 ppm) and olive.
Verwenden
Ethyl acetate is used as a solvent for varnishes, lacquers, and nitrocellulose; as anartificial fruit flavor; in cleaning textiles;and in the manufacture of artificial silk andleather, perfumes, and photographic filmsand plates (Merck 1996). Ethyl Acetate is generally used as a solvent in organic reactions. Environmental contaminants; Food contaminants.
synthetische
Ethyl acetate is made by esterification of acetic acid with ethanol, from acetaldehyde, or by the direct addition of ethylene to acetic acid. BP started a 220,000 tonne/year plant in 2001 to operate the last of these processes, known as AVADA. Ethylene and acetic acid react in the presence of a heteropolyacid catalyst to give ethyl acetate at a claimed high selectivity and 99.97% purity. This is the world’s largest ethyl acetate plant and is motivated by its increasing use as a more “acceptable” solvent than hydrocarbons.
In some countries, where ethanol is expensive or there is surplus acetaldehyde capacity, ethyl acetate is made by a Tishchenko reaction. Sasol in South Africa was said to be investigating such a process in the early 2000s. Ethanol is a solvent for surface coatings, cleaning preparations, and cosmetics. Industrial ethanol is aerobically fermented to white vinegar (dilute acetic acid) of the type used for pickling. Gourmet vinegars—wine vinegar, cider vinegar, and so on, made by fermentation of alcoholic beverages—are also available. Ten percent of industrial ethanol production was used for vinegar in the United States in 2001.
Vorbereitung Methode
Ethyl acetate can be manufactured by the slow distillation of a
mixture of ethanol and acetic acid in the presence of concentrated
sulfuric acid. It has also been prepared from ethylene using an
aluminum alkoxide catalyst.
Reaktionen
Ethyl acetate can be hydrolyzed in acidic or basic conditions to regain acetic acid and ethanol. The use of an acid catalyst accelerates the hydrolysis, which is subject to the Fischer equilibrium mentioned above. In the laboratory, and usually for illustrative purposes only, ethyl esters are typically hydrolyzed in a two step process starting with a stoichiometric amount of strong base, such as sodium hydroxide. This reaction gives ethanol and sodium acetate, which is unreactive toward ethanol:
CH
3CO
2C
2H
5 + Na OH → C
2H
5OH + CH
3CO
2Na
The rate constant is 0.111 dm3 / mol.sec at 25 °C.
Allgemeine Beschreibung
Ethyl acetate, a carboxylate ester, is bio-friendly organic solvent with wide range of industrial applications. Its synthesis by reactive distillation and by acceptorless dehydrogenative dimerization of ethanol has been explored. Its utility as a less toxic alternative to diethyl ether in the formalin-ether (F-E) sedimentation procedure for intestinal parasites has been investigated. Its ability as an acyl acceptor in the immobilized lipase-mediated preparation of biodiesel from crude vegetable oils has been examined. The complete degradation of ethyl acetate to CO
2 using manganese octahedral molecular sieve (OMS-2) has been investigated.
Air & Water Reaktionen
Highly flammable. Slightly soluble in water. Ethyl acetate is slowly hydrolyzed by moisture.
Reaktivit?t anzeigen
Ethyl acetate is also sensitive to heat. On prolonged storage, materials containing similar functional groups have formed explosive peroxides. Ethyl acetate may ignite or explode with lithium aluminum hydride. Ethyl acetate may also ignite with potassium tert-butoxide. Ethyl acetate is incompatible with nitrates, strong alkalis and strong acids. Ethyl acetate will attack some forms of plastics, rubber and coatings. Ethyl acetate is incompatible with oxidizers such as hydrogen peroxide, nitric acid, perchloric acid and chromium trioxide. Violent reactions occur with chlorosulfonic acid. . SOCl2 reacts with esters, such as Ethyl acetate, forming toxic SO2 gas and water soluble/toxic acyl chlorides, catalyzed by Fe or Zn (Spagnuolo, C.J. et al. 1992. Chemical and Engineering News 70(22):2.).
Health Hazard
The acute toxicity of ethyl acetate is low. Ethyl acetate vapor causes eye, skin, and
respiratory tract irritation at concentrations above 400 ppm. Exposure to high
concentrations may lead to headache, nausea, blurred vision, central nervous system
depression, dizziness, drowsiness, and fatigue. Ingestion of ethyl acetate may cause
gastrointestinal irritation and, with larger amounts, central nervous system
depression. Eye contact with the liquid can produce temporary irritation and
lacrimation. Skin contact produces irritation. Ethyl acetate is regarded as a substance
with good warning properties.
No chronic systemic effects have been reported in humans, and ethyl acetate has not
been shown to be a human carcinogen, reproductive, or developmental toxin
Flammability and Explosibility
Ethyl acetate is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Ethyl acetate vapor forms explosive mixtures with air at concentrations of 2 to 11.5% (by volume). Hazardous gases produced in ethyl acetate fires include carbon monoxide and carbon dioxide. Carbon dioxide or dry chemical extinguishers should be used for ethyl acetate fires.
Chemische Reaktivit?t
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Pharmazeutische Anwendungen
In pharmaceutical preparations, ethyl acetate is primarily used as a
solvent, although it has also been used as a flavoring agent. As a
solvent, it is included in topical solutions and gels, and in edible
printing inks used for tablets.
Ethyl acetate has also been shown to increase the solubility of
chlortalidone and to modify the polymorphic crystal forms
obtained for piroxicam pivalate, mefenamic acid, and fluconazole,and has been used in the formulation of microspheres. Ethyl acetate has been used as a solvent in the preparation of a
liposomal amphotericin B dry powder inhaler formulation.(9) Its use
as a chemical enhancer for the transdermal iontophoresis of insulin
has been investigated.
In food applications, ethyl acetate is mainly used as a flavoring
agent. It is also used in artificial fruit essence and as an extraction
solvent in food processing.
Sicherheitsprofil
Potentially poisonous by ingestion. Toxicity depends upon alcohols in question, generally ethanol with methanol as a denaturant. A flammable liquid and dangerous fire hazard; can react vigorously with oxidzing materials. Moderate explosion hazard. See ETHANOL, METHYL ALCOHOL, and n-PROPYL ALCOHOL.
Sicherheit(Safety)
Ethyl acetate is used in foods, and oral and topical pharmaceutical
formulations. It is generally regarded as a relatively nontoxic and
nonirritant material when used as an excipient.
However, ethyl acetate may be irritant to mucous membranes,
and high concentrations may cause central nervous system
depression. Potential symptoms of overexposure include irritation
of the eyes, nose, and throat, narcosis, and dermatitis.
Ethyl acetate has not been shown to be a human carcinogen or a
reproductive or developmental toxin.
The WHO has set an estimated acceptable daily intake of ethyl
acetate at up to 25 mg/kg body-weight.
In the UK, it has been recommended that ethyl acetate be
temporarily permitted for use as a solvent in food and that the
maximum concentration consumed in food should be set at
1000 ppm.
LD50 (cat, SC): 3.00 g/kg
LD50 (guinea-pig, oral): 5.50 g/kg
LD50 (guinea-pig, SC): 3.00 g/kg
LD50 (mouse, IP): 0.709 g/kg
LD50 (mouse, oral): 4.10 g/kg
LD50 (rabbit, oral): 4.935 g/kg
LD50 (rat, oral): 5.62 g/kg
m?gliche Exposition
This material is used as a solvent for
nitrocellulose and lacquer. It is also used in making dyes,flavoring and perfumery, and in smokeless powder
manufacture
Carcinogenicity
Ethyl acetate was not mutagenic in bacterial
assays; it was not genotoxic in a number
of in vivo assays but did cause chromosomal
damage in hamster cells in vitro.
Ethyl acetate has a fruity odor detectable
at 10ppm.
The 2003 ACGIH threshold limit valuetime-
weighted average (TLV-TWA) for ethyl
acetate is 400pm (1440mg/m3).
Environmental Fate
Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.00 g/g which is 54.9%
of the ThOD value of 1.82 g/g.
Photolytic. Reported rate constants for the reaction of ethyl acetate and OH radicals in the
atmosphere (296 K) and aqueous solution are 1.51 x 10
-12 and 6.60 x 10
-13 cm
3/molecule?sec,
respectively (Wallington et al., 1988b).
Chemical/Physical. Hydrolyzes in water forming ethanol and acetic acid (Kollig, 1993). The
estimated hydrolysis half-life at 25 °C and pH 7 is 2.0 yr (Mabey and Mill, 1978).
Stoffwechsel
Ethyl acetate is hydrolysed to ethyl alcohol, which is then partly excreted in the expired air and urine. The rest is metabolized, the acetate fraction becoming incor porated in the body pool (Fassett, 1963).
Lager
Ethyl acetate should be stored in an airtight container, protected
from light and at a temperature not exceeding 30°C. Ethyl acetate is
slowly decomposed by moisture and becomes acidic; the material
can absorb up to 3.3% w/w water.
Ethyl acetate decomposes on heating to produce ethanol and
acetic acid, and will emit acrid smoke and irritating fumes. It is
flammable and its vapor may travel a considerable distance to an
ignition source and cause a ‘flashback’.
The alkaline hydrolysis of ethyl acetate has been shown to be
inhibited by polyethylene glycol and by mixed micelle systems.
Versand/Shipping
UN1173 Ethyl acetate, Hazard Class: 3; Labels:
3-Flammable liquid.
l?uterung methode
The most common impurities in EtOAc are water, EtOH and acetic acid. These can be removed by washing with aqueous 5% Na2CO3, then with saturated aqueous CaCl2 or NaCl, and drying with K2CO3, CaSO4 or MgSO4. More efficient drying is achieved if the solvent is further dried with P2O5, CaH2 or molecular sieves before distillation. CaO has also been used. Alternatively, ethanol can be converted to ethyl acetate by refluxing with acetic anhydride (ca 1mL per 10mL of ester), the liquid is then fractionally distilled, dried with K2CO3 and redistilled. [Beilstein 2 III 127.]
Inkompatibilit?ten
Ethyl acetate can react vigorously with strong oxidizers, strong
alkalis, strong acids, and nitrates to cause fires or explosions. It also
reacts vigorously with chlorosulfonic acid, lithium aluminum
hydride, 2-chloromethylfuran, and potassium tert-butoxide.
Waste disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Generators of waste containing this contaminant (≧100 kg/
mo) must conform with EPA regulations governing storage,
transportation, treatment, and waste disposal.
Regulatory Status
Included in the FDA Inactive Ingredients Database (oral tablets and
sustained-action tablets; topical and transdermal preparations).
Included in nonparenteral medicines licensed in the UK (tablets,
topical solutions, and gels). Ethyl acetate is also accepted for use in
food applications in a number of countries including the UK.
Included in the Canadian List of Acceptable Non-medicinal
Ingredients.
Ethylacetat Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
self curing adhesive SL-B404
D-Glucosepentakis[3,4-dihydroxy-5-[(trihydroxy-3,4,5-benzoyl)oxy]benzoat]
(Ethyl-3-oxobutyrato-O1',O3)bis(propan-2-olato)aluminium
adhesive JX-18-1
adhesive M-861 for polyolefin plastics
Hexadecyltrimethylammoniumchlorid
ETHYL PICOLINOYLACETATE
Ethyl-3-(4-pyridyl)-3-oxopropionat
Enoximone
N-Acetylethylenediamine
Water-proof adhesive
Triphenylsilanol
special adhesive JA-501 for laminating packaging materials
O-Benzyl-N-[(tert-butoxy)carbonyl]-L-tyrosin
2-(4-Ethoxyphenyl)-2-methylpropanol
2-Amino-6-bromopyridine
Tea polyphenol
3-METHYL-4-PYRIDINECARBOXYLIC ACID
N-ETHYL 3-NITROBENZENESULFONAMIDE
special adhesive JA-502 for aluminum-plastics laminating tape
wealant XY-2
1-(Thiazol-2-yl)ethan-1-on
Methyl 4-bromo-3-nitrobenzoate
4-FLUOROBENZYL ISOCYANATE
4(1H)-Pyrimidinone, 2-methyl- (8CI,9CI)
2-(2-FORMYL-PHENOXY)-PROPIONIC ACID
adhesive No.1 for shrink packaging
Piperidin-3-ol
Natrium-[2S-[2α,5α,6β(S*)]]-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylat
N-(tert-Butoxycarbonyl)glycin
Diphenyl N-cyanocarbonimidate
dry laminating adhesive AD
polyurethane adhesive for dry laminating
N-BENZYL-6-CHLORO-N-METHYLPYRIDAZIN-3-AMINE
2-ISOCYANATO-4,6-DIMETHOXYPYRIMIDINE
Methyl 3-bromo-4-methylbenzoate
Natriumheptan-1-sulfonat
coating adhesive tiemao 102
granular adhesive PUA
Methyl-2,5-dihydro-2,5-dioxo-1H-pyrrol-1-carboxylat
