Etylacetat

Product Name:

Ethyl acetate

Synonymer:

EtylacetatBiosyntese; (Benzoyltio); Etylacetatprodusent; Etylacetat (99,8%, HyDry, Waterâ ‰ ¤50 ppm (av KF)); Etylacetat (99,8%, HyDry, med molekylsikt, Waterâ ‰ ¤50 ppm (av KF Diklor 2-; ALKOHOL, REAGENS, DENATURERT; ALKOHOL

CAS:

141-78-6

MF:

C4H8O2

MW:

88.11

EINECS:

205-500-4

Product Categories:

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Mol-fil:

141-78-6.mol

Melting point 

−84 °C(lit.)

Boiling point 

76,5-77,5 ° C (lys)

tetthet

0,902 g / ml ved 25 ° C (opplyst)

damptetthet

3 (20 °C, vs air)

vapor pressure 

73 mm Hg (20 ° C)

refractive index 

n20 / D 1.3720 (lys)

FEMA 

2414 | ETYLACETAT

Fp

26 ° F

storage temp. 

2-8°C

solubility 

Miscible with ethanol, acetone, diethyl ether and benzene.

pka

16-18 (kl 25â „ƒ)

form 

Væske

farge

APHA: ≤10

Spesifikk tyngdekraft

0,902 (20/20â „ƒ)

Relativ polaritet

0.228

Odor

Pleasant fruity odor detectable at 7 to 50 ppm (mean = 18 ppm)

Odor Threshold

0,87 ppm

explosive limit

2,2-11,5%, 38 ° F

Water Solubility 

80 g / l (20 ºC)

λmax

Î »: 256 nm Amax: â ‰ ¤1.00
λ: 275 nm Amax: ≤0.05
λ: 300 nm Amax: ≤0.03
λ: 325-400 nm Amax: ≤0.005

Merck 

14,3757

JECFA-nummer

27

BRN

506104

Henrys lovkonstant

0.39 at 5.00 °C, 0.58 at 10.00 °C, 0.85 at 15.00 °C, 1.17 at 20.00 °C, 1.58 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005)

Eksponeringsgrenser

TLV-TWA 400 ppm (～1400 mg / m3) (ACGIH, MSHA og OSHA); IDLH 10 000 ppm (NIOSH).

Stabilitet:

Stabil. Uforenlig med forskjellige plastmaterialer, sterke oksidasjonsmidler. Svært brannfarlig. Eksplosive damp / luftblandinger. Kan være fuktfølsom.

InChIKey

XEKOWRVHYACXOJ-UHFFFAOYSA-N

CAS DataBase Referanse

141-78-6 (CAS DataBase Reference)

NIST Chemistry Reference

Ethyl acetate(141-78-6)

EPA Substance Registry System

Etylacetat (141-78-6)

Farekoder

F,Xi,Xn,T

Risk Statements 

11-36-66-67-20/21/22-10-39/23/24/25-23/24/25-68/20/21/22

Safety Statements 

16-26-33-36/37-45-7-25

RIDADR 

UN 1173 3/PG 2

WGK Tyskland

1

RTECS 

AH5425000

F

1

Autoignition Temperature

427 ° C

TSCA

Yes

HS kode

2915 31 00

HazardClass 

3

PackingGroup

II

Hazardous Substances Data

141-78-6 (data om farlige stoffer)

Toxicity

LD50 oralt hos rotter: 11,3 ml / kg (Smyth)

organisk esterforbindelse

Ethyl Acetate is an organic ester compound with a molecular formula of C4H8O2 (commonly abbreviated as EtOAc or EA), appears as a colorless liquid. It is highly miscible with all common organic solvents (alcohols, ketones, glycols, esters), which make it a common solvent for cleaning, paint removal and coatings.
Etylacetat finnes i alkoholholdige drikker, frokostblandinger, reddiker, fruktjuicer, øl, vin, brennevin etc. Den har en fruktig karakteristisk lukt som ofte kjennes igjen i lim, neglelakkfjerner, koffeinfri te og kaffe, og sigaretter. På grunn av sin behagelige aroma og lave kostnader, blir dette kjemikaliet ofte brukt og produsert i stor skala i verden, mer enn 1 million tonn årlig.
etylacetatstruktur

Rensing og vannfjerningsmetoder

Ethyl acetate generally has a content of 95% to 98% containing a small amount of water, ethanol and acetic acid. It can be further purified as following: add 100mL of acetic anhydride into 1000mL of ethyl acetate; add 10 drops of concentrated sulfuric acid, heat and reflux for 4h to remove impurities such as ethanol and water, and then further subject to distillation. Distillate is oscillated by 20~30g of anhydrous potassium carbonate and further subject to re-distillation. The product has a boiling point of 77 °C and purity being over 99%.

Bruker

Produksjon

Industriell produksjon av etylacetat er i hovedsak klassifisert i tre prosesser.

The first one is a classical Fischer esterification process of ethanol with acetic acid in presence of acid catalyst. This process needs acid catalyst2 such as sulphuric acid, hydrochloride acid, ptoluene sulfonic acid etc. This mixture converts to the ester in about 65% yield at room temperature. 
CH3CH2OH + CH3COOH ↔ CH3COOC2H5 + H2O
The reaction can be accelerated by acid catalysis and the equilibrium can be shifted to the right by removal of water.

The second one is Tishchenko Reaction of acetaldehyde using aluminium triethoxide as a catalyst. In Germany and Japan, most ethyl acetate is produced via the Tishchenko process. 
2 CH3CHO → CH3COOC2H5
This method has been proposed by two different routes; (i) dehydrogenative process, which uses copper or palladium based catalyst and (ii) the oxidative one, which employs, PdO supported catalysts.

Den tredje, som nylig er kommersialisert, er tilsetning av eddiksyre til etylen ved bruk av leire og heteroploysyre7 som katalysator.
CH2 = CH2 + CH3COOH â † ’CH3COOC2H5
Prosessene har imidlertid noen ulemper; både konvensjonell forestring og tilsetning av eddiksyre til etylen trenger lagerbeholdere og apparater for flere fôrråvarer. Videre bruker de eddiksyre som forårsaker apparatkorrosjon. Selv om Teshchenko Reaction bare bruker ett fôr og det er et ikke-etsende materiale, er det vanskelig å håndtere acetaldehyd fordi det ikke er tilgjengelig utenfor petrokjemisk industriområde.
Under slike omstendigheter er en forbedret prosess for etylacetatproduksjon sterkt ønsket.

Slokkemiddel

tørt pulver, tørkesand, karbondioksid, skum og 1211 brannslokkingsmiddel

Professional standards

TWA 1400 mg/m³; STEL 2000 mg/m³

Description

Ethyl acetate (systematically, ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound with the formula CH3COOCH2CH3. 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.

Kjemiske egenskaper

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.

Fysiske egenskaper

Clear, colorless, mobile liquid with a pleasant, sweet fruity odor. Experimentally determined detection and recognition odor threshold concentrations were 23 mg/m3 (6.4 ppmv) and 48 mg/m3 (13.3 ppmv), respectively (Hellman and Small, 1974). Cometto-Mu?iz and Cain (1991) reported an average nasal pungency threshold concentration of 67,300 ppmv.

Bruker

Ethyl acetate is used primarily as a solvent and diluent, being favored because of its low cost, low toxicity, and agreeable odor. For example, it is commonly used to clean circuit boards and in some nail varnish removers (acetone and acetonitrile are also used). Coffee beans and tea leaves are decaffeinated with this solvent.It is also used in paints as an activator or hardener.[citation needed] Ethyl acetate is present in confectionery, perfumes, and fruits. In perfumes, it evaporates quickly, leaving only the scent of the perfume on the skin.
3 - 1 - Laboratoriebruk
I laboratoriet brukes blandinger som inneholder etylacetat ofte inkolumn kromatografi og ekstraksjoner. Etylacetat blir sjelden valgt som areaksjonsløsningsmiddel fordi det er utsatt for hydrolyse og transforestring.
3 - 2 - Forekomst i viner
Ethyl acetate is the most common ester in wine, being the product of the most common volatile organic acid — acetic acid, and the ethyl alcohol generated during the fermentation. The aroma of ethyl acetate is most vivid in younger wines and contributes towards the general perception of "fruitiness" in the wine. 
3 - 3 - Entomologisk drapsmiddel
Innen entomologi er etylacetat et effektivt kvelningsmiddel for bruk i insektinnsamling og studier. I en drepekar som er fylt med etylacetat, vil dampene drepe det innsamlede (vanligvis voksne) insektet raskt uten å ødelegge det. Fordi det ikke er hygroskopisk, holder etylacetat også insekten myk nok til å tillate riktig montering som passer for en samling.

Bruker

Etylacetat brukes som løsningsmiddel for lakk, lakk og nitrocellulose; asan kunstig frukt smak; ved rengjøring av tekstiler, og ved produksjon av kunstig silke og lær, parfymer og fotografiske filmer og plater (Merck1996).

Bruker

Farmasøytisk hjelpemiddel (smak); essenser av kunstig frukt; løsningsmiddel for nitrocellulose, lakk, lakk og flydoper; produksjon av røykfritt pulver, kunstlær, fotografiske filmer og plater, kunstig silke, parfymer; rengjøringstekstiler osv.

Produksjonsmetoder

Etylacetat kan fremstilles ved langsom destillasjon av en blanding av etanol og eddiksyre i nærvær av konsentrert svovelsyre. Det er også fremstilt fra etylen ved bruk av en aluminiumalkoksydkatalysator.

Produksjonsmetoder

Ethyl acetate is synthesized in industry mainly via the classic Fischer esterification reaction of ethanol and acetic acid. This mixture converts to the ester in about 65% yield at room temperature:
CH3CH2OH + CH3COOH ? CH3COOCH2CH3 + H2O
Reaksjonen kan akselereres ved syrekatalyse, og likevekten kan forskyves til høyre ved fjerning av vann. Det fremstilles også i industrien ved å bruke Tishchenko-reaksjonen, ved å kombinere to ekvivalenter acetaldehyd i nærvær av en alkoksydkatalysator:
2 CH3CHO â † ’CH3COOCH2CH3.

Preparation

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.

Reactions

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:
CH3CO2C2H5 + Na OH â † ’C2H5OH + CH3CO2Na
Hastighetskonstanten er 0,111 dm3 / mol.sek ved 25 ° C.

Aroma terskelverdier

Deteksjon: 5 ppb til 5 ppm

Luft- og vannreaksjoner

Meget brannfarlig, lett løselig i vann. Etylacetat hydrolyseres sakte av fuktighet.

Reaktivitetsprofil

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

Brannfarlig

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

Brennbarhet og eksplosibilitet

Etylacetat er brennbar væske (NFPA-klassifisering = 3), og dampen kan føre en betydelig avstand til en antennelseskilde og "blinke tilbake". Etylacetatdamp danner eksplosive blandinger med luft i konsentrasjoner på 2 til 11,5% (volum). Farlige gasser produsert i etylacetatbranner inkluderer karbonmonoksid og karbondioksid. Karbondioksid eller tørrkjemiske brannslokkere skal brukes til etylacetatbranner.

Chemical Reactivity

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.

Pharmaceutical Applications

I farmasøytiske preparater brukes etylacetat primært som løsningsmiddel, selv om det også har blitt brukt som smaksstoff. Som løsningsmiddel er det inkludert i aktuelle løsninger og geler, og i spiselige trykkfarger som brukes til tabletter.
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.
I matvareapplikasjoner brukes etylacetat hovedsakelig som smaksstoff. Det brukes også i kunstig fruktessens og som et ekstraksjonsløsningsmiddel i matforedling.

Sikkerhetsprofil

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.

Sikkerhet

Etylacetat brukes i matvarer, og orale og aktuelle farmasøytiske formuleringer. Det blir generelt sett på som et relativt ikke-giftig og ikke-irriterende materiale når det brukes som et hjelpestoff.
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 (mus, IP): 0,709 g / kg
LD50 (mus, oral): 4,10 g / kg
LD50 (rabbit, oral): 4.935 g/kg
LD50 (rat, oral): 5.62 g/kg

Chemical Synthesis

Ved å reagere eddiksyre og etanol i nærvær av svovelsyre; ved destillasjon av natriumkalium, eller blyacetat med etanol i nærvær av svovelsyre; bypolymerizatin av acetaldehyd i nærvær av aluminiumetylat oraluminiumacetat som katalysatorer.

Potensiell eksponering

Dette materialet brukes som løsningsmiddel for nitrocellulose og lakk. Det brukes også til å lage fargestoffer, smaksstoffer og parfymeri, og i produksjon av røykfritt pulver

Kilde

Identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).

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.
Fotolytisk. Rapporterte hastighetskonstanter for reaksjonen av etylacetat- og OH-radikaler i teatmosfæren (296 K) og den vandige løsningen er henholdsvis 1,51 x 10-12 og 6,60 x 10-13 cm3 / molekyl sec sek (Wallington et al., 1988b).
Kjemisk / fysisk. Hydrolyserer vann som danner etanol og eddiksyre (Kollig, 1993). Den estimerte halveringstiden for hydrolyse ved 25 ° C og pH 7 er 2,0 år (Mabey and Mill, 1978).

storage

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’.
Den alkaliske hydrolysen av etylacetat har vist seg å bli inhibert av polyetylenglykol og av blandede micellsystemer.

Shipping

UN1173 Etylacetat, fareklasse: 3; Etiketter: 3-brennbar væske.

Rensingsmetoder

De vanligste forurensningene i EtOAc er vann, EtOH og eddiksyre. Disse kan fjernes ved å vaske med vandig 5% Na2CO3, deretter med mettet vandig CaCl2 eller NaCl, og tørke med K2CO3, CaSO4 eller MgSO4. Mer effektiv tørking oppnås hvis løsningsmidlet tørkes ytterligere med P2O5, CaH2 eller molekylsikt før destillasjon. CaO har også blitt brukt. Alternativt kan etanol omdannes til etylacetat ved tilbakeløpskjøling med eddiksyreanhydrid (ca. 1 ml pr. 10 mlester), væsken destilleres deretter fraksjonelt, tørkes med K2CO3 og omdestilleres. [Beilstein 2 III 127.]

Incompatibilities

Etylacetat kan reagere kraftig med sterke oksidasjonsmidler, sterke baser, sterke syrer og nitrater for å forårsake brann eller eksplosjoner. Det reagerer også kraftig med klorsulfonsyre, litiumaluminiumhydrid, 2-klormetylfuran og kalium-tert-butoksid.

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.

Forskriftsstatus

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.

Råvarer

Etanol -> Svovelsyre -> Iseddiksyre -> Kaliumkarbonat -> 1-Butanol -> Kalsiumoksid -> Kaliumacetat -> keten

Forberedelsesprodukter

N-ETHYL 3-NITROBENZENESULFONAMIDE-->Methyl 4-bromo-3-nitrobenzoate-->ETHYL ISONICOTINOYLACETATE-->Sodium 1-heptanesulfonate-->D-glucose pentakis[3,4-dihydroxy-5-[(trihydroxy-3,4,5-benzoyl)oxy]benzoate]-->Ampicillin sodium-->Diphenyl N-cyanocarbonimidate-->4(1H)-Pyrimidinone, 2-methyl- (8CI,9CI)-->4-FLUOROBENZYL ISOCYANATE-->2-(2-FORMYL-PHENOXY)-PROPIONIC ACID-->N-METHOXYCARBONYLMALEIMIDE-->2-Amino-6-bromopyridine-->3-METHYL-4-PYRIDINECARBOXYLIC ACID-->N-BENZYL-6-CHLORO-N-METHYLPYRIDAZIN-3-AMINE-->polyurethane adhesive for dry laminating-->2-ISOCYANATO-4,6-DIMETHOXYPYRIMIDINE-->Methyl 3-bromo-4-methylbenzoate-->N-Acetylethylenediamine-->3-Hydroxypiperidine-->ETHYL PICOLINOYLACETATE-->N-Hexadecyltrimethylammonium chloride-->Boc-O-benzyl-L-tyrosine-->2-Acetylthiazole-->ALUMINUM DI(ISOPROPOXIDE)ACETOACETIC ESTER CHELATE-->Tea polyphenol-->2-(4-Ethoxyphenyl)-2-methylpropanol-->BOC-Glycine-->dry laminating adhesive AD-->adhesive No.1 for shrink packaging-->Triphenylsilanol-->granular adhesive PUA-->special adhesive JA-501 for laminating packaging materials-->special adhesive JA-502 for aluminum-plastics laminating tape-->Enoximone-->coating adhesive tiemao 102-->adhesive M-861 for polyolefin plastics-->self curing adhesive SL-B404-->wealant XY-2-->Water-proof adhesive-->adhesive JX-18-1