109-60-4 Usage
Description
Propyl acetate, also known as propyl ethanoate, is an organic compound with a molecular formula of C5H10O2. It is a clear and colourless liquid with with a mild fruity odor. It is highly flammable with a flash point of 14°C and a flammability rating of 3. It is highly miscible with all common organic solvents (alcohols, ketones, glycols, esters) but has only slight miscibility in water. Propyl acetate is found in apple and formed by the esterification of acetic acid and 1-propanol (known as acondensation reaction), often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct. It is primarily intended as a solvent in the coatings and printing inks industries. It is widely used in fragrances and as a flavor additive due to its odor. It also acts as a good solvent for cellulose nitrate, acrylates, alkyd resins, rosin, plasticizers, waxes, oils and fats.
Chemical Properties
Propyl acetate has a fruity (pear–raspberry) odor with a pleasant, bittersweet flavor reminiscent of pear on dilution. The Odor Threshold is 70 milligram per cubic meter and 2.8 milligram per cubic meter (New Jersey Fact Sheet).
Physical properties
Clear, colorless, flammable liquid with a pleasant, pear-like odor. Experimentally determined
detection and recognition odor threshold concentrations were 200 μg/m3 (48 ppbv) and 600 μg/m3
(140 ppbv), respectively (Hellman and Small, 1974). An odor threshold concentration of 240 ppbv
was determined by a triangular odor bag method (Nagata and Takeuchi, 1990). Cometto-Mu?iz
and Cain (1991) reported an average nasal pungency threshold concentration of 17,575 ppmv.
Occurrence
Reported found in apple, apple juice, apricot, banana, black currants, guava, grapes, melon, peach, pears, pineapple,
plum, strawberry, tomato, vinegar, wheat and rye bread, feta cheese, Gruyere cheese, domiati cheese, yogurt, beef fat, beer,
cognac, bourbon and malt whiskey, cider, grape wines, cocoa, potato chips, honey, passion fruit, starfruit, fig, prickly pear, jackfruit,
litchi, sake, loquat, mountain papaya, arrack, nectarine and pepino fruit.
Uses
n-Propyl acetate is used as a solvent for cellulose derivatives, plastics, and resins; in flavors and perfumes; and in organic synthesis.
Preparation
Propyl Acetate is formed by the esterification of acetic acid and 1-propanol with sulfuric acid as a catalyst and water produced as a byproduct. or By direct acetylation of propyl alcohol.
Definition
ChEBI: Propyl acetate is an acetate ester obtained by the formal condensation of acetic acid with propanol. It has a role as a fragrance and a plant metabolite. It derives from a propan-1-ol.
Production Methods
n-Propyl acetate is manufactured from acetic acid and a
mixture of propene and propane in the presence of a zinc
chloride catalyst. It is used as a solvent for nitrocellulose-
based lacquers, waxes, polyamide inks, acrylic inks, and
insecticide formulations .
Manufacturers include Eastman Chemical Company,
Hoechst Celanese Corporation, and Union Carbide
Corporation.
Aroma threshold values
Detection: 2.7 to 11 ppm. Aroma characteristics at 1.0%: pungent, solventlike ethereal, fruity lift, green
banana sweet with an apple and tropical fruit nuance.
Taste threshold values
Taste characteristics at 10 to 15 ppm: bubble gum estery, fruity, ethereal, tutti-frutti, banana and honey.
General Description
N-propyl acetate appears as a clear colorless liquid with a pleasant odor. Flash point 58°F. Less dense than water, Vapors are heavier than air.
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Reactivity Profile
Propyl acetate is an ester. Propyl acetate is colorless, highly flammable liquid, moderately toxic. Dangerous fire hazard when exposed to heat, flame, sparks, or strong oxidizers. When heated to decomposition Propyl acetate emits acrid smoke and irritating fumes [Lewis, 3rd ed., 1993, p. 1093].
Hazard
Flammable, dangerous fire risk, explosive
limits in air 2–8%. Eye and upper respiratory tract
irritant.
Health Hazard
The acute toxicity of n-propyl acetate islow in test animals. The toxicity, however,is slightly greater than ethyl acetate andisopropyl acetate. Exposure to its vaporsproduces irritation of the eyes, nose, andthroat and narcotic effects. A 5-hour expo sure to 9000- and 6000-ppm concentrationsproduced narcotic symptoms in cats andmice, respectively (Flury and Wirth 1933).A 4-hour exposure to 8000 ppm was lethalto rats. Ingestion of the liquid can cause narcotic action. A high dose can cause death. Adose of 3000 mg/kg by subcutaneous admin istration was lethal to cats. The liquid maycause mild irritation upon contact with skinLD50 value, oral (mice): 8300 mg/kg.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Highlyflammable
Safety Profile
Moderately toxic by
intraperitoneal and subcutaneous routes.
Mildly toxic by ingestion and inhalation.
Human systemic effects by inhalation:
lachrymation, cough. A skin irritant. A
narcotic at high concentrations. Isopropyl
acetate is slightly less narcotic than normal propyl acetate. A flammable liquid and
dangerous fire hazard when exposed to heat,
flame, or oxidizers. Explosive in the form of
vapor when exposed to heat or flame. Can
react vigorously with oxidizing materials. To
fight fire, use alcohol foam, CO2, dry
chemical. When heated to decomposition it
emits acrid smoke and irritating fumes.
Potential Exposure
Propyl acetate is a used as a solvent
for plastics and cellulose ester resins; perfume ingredient;
component of food flavoring. It is also used as a chemical
intermediate.
Environmental fate
Photolytic. Reported rate constants for the reaction of n-propyl acetate and OH radicals in the
atmosphere and aqueous solution are 2.7 x 10-12 cm3/molecule?sec (Hendry and Kenley, 1979) and
2.30 x 10-13 cm3/molecule?sec (Wallington et al., 1988b).
Chemical/Physical. Slowly hydrolyzes in water forming acetic acid and 1-propanol.
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent
concentration of 248 mg/L. The adsorbability of the carbon used was 149 mg/g carbon (Guisti et
al., 1974).
Shipping
UN1276 n-Propyl acetate, Hazard Class: 3;
Labels: 3-Flammable liquid.
Purification Methods
Wash the ester with saturated aqueous NaHCO3 until neutral, then with saturated aqueous NaCl. Dry it with MgSO4 and fractionally distil it. [Beilstein 2 IV 138.]
Incompatibilities
Contact with nitrates, strong oxidizers;
strong alkalis; strong acids; may pose risk of fire and
explosions. Attacks plastic.
References
1.https://en.wikipedia.org/wiki/Propyl_acetate2.http://www.hmdb.ca/metabolites/HMDB342373.http://www.eastman.com/Pages/ProductHome.aspx?product=710010524.http://www.khchemicals.com/zh/categories/acetates/n-propyl-acetate/5.https://www.alfa.com/zh-cn/catalog/L15355/6.http://product-finder.basf.com/group/corporate/product-finder/en/brand/N_PROPYL_ACETATE
Check Digit Verification of cas no
The CAS Registry Mumber 109-60-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 109-60:
(5*1)+(4*0)+(3*9)+(2*6)+(1*0)=44
44 % 10 = 4
So 109-60-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O2/c1-3-4-7-5(2)6/h3-4H2,1-2H3
109-60-4Relevant articles and documents
Transacylation. Biomimetic synthesis of esters of acetic acid
Devedjiev, Ivan T.,Ganev, Vesselin G.
, p. 350 - 352 (2006)
By mixing of β-hydroxypropyl phosphate and acetic acid in ethanol solution, ethyl acetate is produced. As found, acetyl phosphate is first formed, then it reacts with the solvent to give the final ethyl acetate product. By similar procedures, acetates of methanol, n-propanol, and n-butanol are also produced. Propylene oxide serves as a condensing agent.
-
Glukhovtsev,Nikishin
, (1976)
-
Ignatenko
, p. 219 (1973)
Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters
Salnikov, Oleg G.,Chukanov, Nikita V.,Kovtunova, Larisa M.,Bukhtiyarov, Valerii I.,Kovtunov, Kirill V.,Shchepin, Roman V.,Koptyug, Igor V.,Chekmenev, Eduard Y.
, p. 1389 - 1396 (2021)
Magnetic resonance imaging of [1-13C]hyperpolarized carboxylates (most notably, [1-13C]pyruvate) allows one to visualize abnormal metabolism in tumors and other pathologies. Herein, we investigate the efficiency of 1H and 13C hyperpolarization of acetate and pyruvate esters with ethyl, propyl and allyl alcoholic moieties using heterogeneous hydrogenation of corresponding vinyl, allyl and propargyl precursors in isotopically unlabeled and 1-13C-enriched forms with parahydrogen over Rh/TiO2 catalysts in methanol-d4 and in D2O. The maximum obtained 1H polarization was 0.6±0.2 % (for propyl acetate in CD3OD), while the highest 13C polarization was 0.10±0.03 % (for ethyl acetate in CD3OD). Hyperpolarization of acetate esters surpassed that of pyruvates, while esters with a triple carbon-carbon bond in unsaturated alcoholic moiety were less efficient as parahydrogen-induced polarization precursors than esters with a double bond. Among the compounds studied, the maximum 1H and 13C NMR signal intensities were observed for propyl acetate. Ethyl acetate yielded slightly less intense NMR signals which were dramatically greater than those of other esters under study.
Heteropolyacid encapsulated in Cu3(BTC)2 nanocrystals: An effective esterification catalyst
Wee, Lik H.,Janssens, Nikki,Bajpe, Sneha R.,Kirschhock, Christine E.A.,Martens, Johan A.
, p. 275 - 280 (2011)
An original synthesis approach to prepare Cu3(BTC)2 (BTC = benzene tricarboxylic acid) encapsulated Keggin phosphotungstic acid (HPW) [HPW/Cu3(BTC)2] involving mixing of reagents at room temperature, quenching in liquid nitrogen and freeze drying has resulted in the formation of nanocrystals. The catalytic properties of the as-synthesized nanocrystalline materials were assessed using a model esterification reaction of acetic acid with 1-propanol. HPW/Cu3(BTC)2 catalyst is partially dissolved in presence of acetic acid. In the esterification reaction the molar ratio of acetic acid to 1-propanol is critical. At high molar ratio of acetic acid to 1-propanol (1:2) leaching of Cu2+ and HPW was observed. However, at low molar ratio of acetic acid to 1-propanol (1:40) leaching of Cu2+ and HPW could be prevented and the catalyst was stable. Nanosized HPW/Cu3(BTC)2 showed higher catalytic activity compared to micron-size Cu3(BTC)2 (HKUST-1), ultrastable Y zeolite and micron-sized HPW/Cu3(BTC)2 catalysts. The stability of the nanosized MOF catalyst in acidic reaction medium after esterification reaction was investigated by powder X-ray diffraction (PXRD), scanning electron microscope (SEM) and N2 adsorption.
Base-Catalyzed Solvolysis of 1,1,1-Trihaloacetones in the Presence of Ammonia Buffer. Analogy with Substitution at Silicon and Tin
Stanczyk, W.,Chmielecka, J.,Chojnowski, J.
, p. 3757 - 3759 (1982)
-
Supported heteropolyacids: Sytnhesis, characterization and effect of supports on esterification reactions
Brahmkhatri,Patel
, p. 380 - 384 (2010)
12-Tungstophosphoric acid supported onto silica was synthesized by impregnation. The supports and synthesized catalysts were characterized for chemical stability, ion exchange capacity, thermogravimetric analysis, differential scanning calorimetry, FT-IR, and BET surface area. The catalytic activity was evaluated for liquid phase esterification reactions. The catalyst was regenerated and reused. The best catalyst was cal- cined at different temperatures and its catalytic activity was also evaluated for esterification reactions under optimized conditions. Further, obtained results are compared with l2-tungstophosphoric acid supported onto zirconia in order to see effect of acidic nature of support on catalytic activity as well as thermal stability of the catalyst. Pleiades Publishing, Ltd., 2010.
Oxidation of Propane: Influence of the Nature of Catalyst, Cocatalyst, and Coreductant
Chepaikin, E. G.,Menchikova, G. N.,Pomogailo, S. I.
, p. 781 - 786 (2021/08/03)
Abstract: Variation of the nature of the components of the catalytic systems comprisinga catalyst [Pd/C, Pd(α,α-bipy)Cl2,RhCl3] and a cocatalyst(FeSO4, CuSO4), as well as acoreductant (H2, CO), allows exerting some control overthe selectivity of the process of propane oxidation with oxygen. In particular,the yield of carbonyl compounds such as acetone and propanal in the presence ofthe Pd/C–FeSO4–H2catalytic systemreached 90%, and that of propyl esters in the presence ofRhCl3–CuSO4–CO catalyticsystem was 64.5%. These differences are supposedly attributable to the changesin the process mechanism depending on the composition of the catalyticsystems. [Figure not available: see fulltext.]
Alcohol-Activated Vanadium-Containing Polyoxometalate Complexes in Homogeneous Glucose Oxidation Identified with 51V-NMR and EPR Spectroscopy
Wesinger, Stefanie,Mendt, Matthias,Albert, Jakob
, p. 3662 - 3670 (2021/06/18)
Alcoholic solvents, especially methanol, show an activating affect for heteropolyacids in homogenously catalysed glucose transformation reactions. In detail, they manipulate the polyoxometalate-based catalyst in a way that thermodynamically favoured total oxidation to CO2 can be completely supressed. This allows a nearly 100 % carbon efficiency in the transformation reaction of glucose to methyl formate in methanolic solution at mild reaction conditions of 90 °C and 20 bar oxygen pressure. By using powerful spectroscopic tools like 51V-NMR and continuous wave EPR we could unambiguously prove that the vanadate-methanol-complex[VO(OMe)3]n is responsible for the selectivity shift in methanolic solution compared to the aqueous reference system.
