591-87-7

Basic information

• Product Name: Allyl acetate
• Synonyms: 2-Propenyl acetate;2-Propenyl ester of acetic acid;2-propenylmethanoate;3-acetoxy-1-propene;acetated’allyle;Aceticacid,2-propenylester;aceticacidprop-2-enylester;CH2=C(CH3)OC(=O)CH3
• CAS NO: 591-87-7
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 209-734-8
• Product Categories: Allyl Monomers;Monomers;Polymer Science
• Mol File: 591-87-7.mol
• Article Data: 104

Chemical Properties

• Melting Point: 6°C
• Boiling Point: 103-104 °C(lit.)
• Flash Point: 44 °F
• Appearance: Clear colorless/Liquid
• Density: 0.928 g/mL at 25 °C(lit.)
• Vapor Pressure: 31.4mmHg at 25°C
• Refractive Index: n20/D 1.404(lit.)
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• Solubility: 28g/l
• Explosive Limit: 2.1-13.0%(V)
• Water Solubility: slightly
• Merck: 14,285
• BRN: 1742050
• CAS DataBase Reference: Allyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl acetate(591-87-7)
• EPA Substance Registry System: Allyl acetate(591-87-7)

Safety Data

• Hazard Codes: F,T
• Statements: 11-21-23/25-36-25
• Safety Statements: 16-26-36-45-27
• RIDADR: UN 2333 3/PG 2
• WGK Germany: 3
• RTECS: AF1750000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 591-87-7(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Allyl acetate is used as a flavoring agent in various food products due to its pleasant aroma. It is added to nonalcoholic beverages at a concentration of 1 ppm, ice cream and ices at 2 ppm, candy at 5 ppm, baked goods at 5 ppm, and margarine at 2 ppm.
Used in Industrial Applications:
Allyl acetate serves as an important industrial intermediate, playing a crucial role in the synthesis of colophony and bond. It is utilized in the production of various chemicals and materials, contributing to the development of different industries.
Chemical Properties:
Allyl acetate is a flammable, colorless liquid with an acrid odor. It is insoluble in water and slightly less dense than water, which causes it to float on the surface. The flash point of allyl acetate is below 75°F, making it a potential fire hazard. It is poisonous by ingestion and moderately toxic by inhalation and skin contact, and it can cause irritation to the skin and eyes.

Production Methods

Allyl acetate is produced by the following methods: decarboxylation of allylmalonic acid with heat, boiling ethyl 4- chloro-N-valerate in quinoline, and acetoxylation of propylene. Allyl acetate is produced primarily for manufacturing allyl alcohol. It is also used as a synthetic flavoring for cheese, butter, and fruit.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Allyl acetate is an ester. Reacts with acids to liberate heat along with alcohols and acids. Generates heat with strong oxidizing acids. The reaction may be sufficiently exothermic to ignite the reaction products. Also generates heat with basic solutions. Generates flammable hydrogen with alkali metals and hydrides. Emits acrid smoke and irritating fumes when heated to decomposition.

Hazard

Skin and eye irritant; poisonous.

Health Hazard

TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

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 and poison 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.

Safety Profile

Poison by ingestion. Moderately toxic by inhalation and skin contact. A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. Dangerous fire hazard. See also ALLYL COMPOUNDS

Potential Exposure

Allyl Acetate is used to control insects in homes and animal shelters, and to treat lice in humans. May be used to enhance taste of dairy products and fruit. Generally speaking, most allyl compounds may be metabolized to allyl alcohol (see A:0540) which is metabolized to acrolein (see A:0380).

Shipping

UN2333 Allyl acetate, Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous materials

Purification Methods

The ester is freed from peroxides by standing with crystalline ferrous ammonium sulfate, then washed with 5% NaHCO3, followed by saturated CaCl2 solution. Dry it with Na2SO4 and fractionally distil it in an all-glass apparatus. FLAMMABLE LIQUID. [Beilstein 2 H 136, 2 IV 180.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Incompatible with strong acids (liberates heat), nitrates, strong alkalis (liberates heat). Contact with alkali metals and strong reducing agents such as hydrides evolves highly flammable hydrogen gas. Attacks some plastics, coatings, and rubber. Flow or agitation of substance may generate electrostatic charges due to low conductivity; ground all equipment containing this material

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.

Upstream product

• 556-56-9 allyl iodid 
• 563-63-3 silver(I) acetate 
• 628-66-0 1,3-diacetoxypropane 
• 7575-57-7 allyl benzenesulfonate 
• 108-24-7 acetic anhydride 
• 7393-45-5 cyclopropyl chloride 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 30074-98-7 1-Acetyl-4(1H)-pyridinon 
• 107-18-6 allyl alcohol 
• 23277-12-5 tetrahydro-2-methyl-2-furyl hydroperoxide 
• 187737-37-7 propene 
• 3375-31-3 palladium diacetate 
• 623-84-7 1,2-diacetoxypropane 

Downstream Products

• 6387-89-9 glycidyl acetate 
• 16703-82-5 DL-2,5-Diacetoxy-1-acetoxymethyl-cyclohexen-⁽³⁾ 
• 131323-45-0 (E)-1-(furan-2-yl)but-2-en-1-one 
• 14315-97-0 1,1,3-trimethoxypropane 
• 18545-28-3 3-acetoxypropanal 
• 592-20-1 Acetol acetate 
• 143056-89-7 3-acetoxy-1,1-dimethoxy-propane 
• 73827-97-1 allyl-3-hydroxy-3-(2-methoxy-4,5-methylenedioxyphenyl)-propionate 
• 3897-04-9 methyl 2-acetylpent-4-enoate 
• 4383-22-6 Allylbenzylamine 
• 4121-39-5 9-allyl-9H-adenine 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 512-56-1 trimethyl phosphite 
• 757-54-0 allylphosphonic acid dimethyl ester 

Relevant articles and documents

Effect of palladium and copper content of zeolite catalysts on the kinetic parameters of the oxidative acetylation of propylene

1. Using the methods of mathematical planning of an experiment, a kinetic model has been obtained for the oxidative acetylation of propylene to allyl acetate and the effect of the composition of the Pd, Cu/mordenite catalyst on its parameters has been determined. 2. The kinetic parameters (1g k0)0, Q, 1g a0 and E0 correlate strongly and form a gully on the surface of the minimized functional. Regularization of the values of the kinetic parameters was carried out by isolating a subregion of the gully satisfying the Boudart thermodynamic relationships. 3. On varying the Pd and Cu content of the catalyst within the limits 0.1 to 3.0%, the activation energy and the logarithm of the preexponential factor of the rate constant vary over the range 2-11 kcal/mole and 0.255-3.453, respectively.

Heterocyclization, deprotection and isomerization in an intramolecular palladium-catalysed tertiary amine-allyl coupling reaction

N-Methyl-N-allyl-2-(1-acetoxyalIyl)benzylamine reacts in the presence of tetrakis(triphenylphosphine)palladium to afford a mixture of an isoindole, a 2-benzazepine and allyl acetate; the likely reaction pathway involves a multistep procedure whereby each Pd atom is implicated at least four times, the formation of the isoindole occuring first, followed by an isomerisation to the benzazepine derivative.

Second-Generation meta-Phenolsulfonic Acid-Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification

A second-generation m-phenolsulfonic acid-formaldehyde resin (PAFR II) catalyst was prepared by condensation polymerization of sodium m-phenolsulfonate and paraformaldehyde in an aqueous H2SO4 solution. This reusable, robust acid resin catalyst was improved in both catalytic activity and stability, maintaining the characteristics of the previous generation catalyst (p-phenolsulfonic acid-formaldehyde resin). PAFR II was applied in the batchwise and continuous-flow direct esterification without water removal and provided higher product yields in continuous-flow esterification than any other commercial ion-exchanged acid catalyst tested.

How to Design Selective Ligands for Highly Conserved Binding Sites: A Case Study Using N-Myristoyltransferases as a Model System

A model system of two related enzymes with conserved binding sites, namely N-myristoyltransferase from two different organisms, was studied to decipher the driving forces that lead to selective inhibition in such cases. Using a combination of computational and experimental tools, two different selectivity-determining features were identified. For some ligands, a change in side-chain flexibility appears to be responsible for selective inhibition. Remarkably, this was observed for residues orienting their side chains away from the ligands. For other ligands, selectivity is caused by interfering with a water molecule that binds more strongly to the off-target than to the target. On the basis of this finding, a virtual screen for selective compounds was conducted, resulting in three hit compounds with the desired selectivity profile. This study delivers a guideline on how to assess selectivity-determining features in proteins with conserved binding sites and to translate this knowledge into the design of selective inhibitors.

Catalytic application of zinc complex of oxygen depleted 1,3-bis(pyrazole)-p-tert-butylcalix[4]arene

In this paper we have described the synthesis and coordination properties of monometallic Zinc complex of oxygen depleted bis(pyrazole)-p-tert-butylcalix[4]arene ligand. We also present the catalytic activity of the Zinc–bis(pyrazole) complex, in acetylation of alcohols and lactide polymerization.

Coating of polydopamine on polyurethane open cell foams to design soft structured supports for molecular catalysts

Polydopamine-coated polyurethane open cell foams are used as structured supports for molecular catalysts through the covalent anchoring of alkoxysilyl arms by the catechol groups of the mussel-inspired layer. This strong bonding prevents their leaching. No alteration of the mechanical properties of the flexible support is observed after repeated uses of the catalytic materials.

Palladium-Catalyzed Aerobic Homocoupling of Alkynes: Full Mechanistic Characterization of a More Complex Oxidase-Type Behavior

A combined experimental and computational approach has been used to shed light on the mechanism of the Pd-catalyzed oxidative homocoupling of alkynes using oxygen as the oxidant. Mechanistic understanding is important because of the synthetically relevant direct involvement of oxygen in the oxidative coupling and because of the presence of related processes as undesired side reactions in cross-coupling reactions involving terminal alkynes. A low-ligated [Pd(PPh3)(alkyne)] complex is key in the process, and it can be conveniently generated from allylic palladium(II) complexes in the presence of a base or from Pd(I) allylic dimers as precatalysts. The catalytic coupling occurs by alkyne metalation to give an anionic [Pd(PPh3)(alkynyl)]- complex that is then oxidized by oxygen. The interaction with oxygen occurs only on this electron-rich Pd(0) anionic species and leads to a (κO,κO-peroxo)palladium(II) singlet intermediate that undergoes subsequent protonolysis to give a (κO-hydroperoxo)palladium(II) complex and then hydrogen peroxide. The second alkyne metalation occurs on a Pd(II) derivative to give a bis(alkynyl)palladium(II) complex that evolves to the product by reductive elimination as the product-forming step. This reaction is an oxidase-type process that, in contrast to most Pd-catalyzed oxidative processes, occurs without separation of the substrate transformation and the catalyst oxidation, with these two processes being intertwined and dependent on one another.

METHODS AND COMPOSITIONS FOR TERPENOID SYNTHESIS

In one aspect, the disclosure relates to methods for preparation of terpene and terpene-like molecules. In a further aspect, the disclosure relates to the products of the disclosed methods, i.e., terpene and terpene-like molecules prepared using the disclosed methods. Intermediates for the synthesis of a wide variety of terpenoids are γ-allyl Knoevenagel adducts or quasi γ-allyl Knoevenagel adducts are disclosed. In various aspects, methods of preparing terpenoids through these intermediates are disclosed. The methods can comprise α-alkylation of an allylic electrophile followed by ring-closure metathesis to a polycyclic terpenoid structure. In a further aspect, the disclosure pertains to terpenoid frameworks, and compounds prepared via disclosed oxidation and substitution reactions on the disclosed terpenoid frameworks. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

Assembly of Terpenoid Cores by a Simple, Tunable Strategy

Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.

Method for the production of acetic acid allyl ester

The invention relates to a method for producing propenyl ethanoate, and mainly aims at solving the problems in the prior art that a catalyst is low in activity and selectivity. Through adopting the method for producing the propenyl ethanoate, propylene, acetic acid, oxygen and water are taken as raw materials, and react with a Pd catalyst in a fixed bed reactor in a contacting manner, so as to generate an effluent containing the propenyl ethanoate; the tubular fixed bed reactor comprises at least two annular baffle plates (7) and at least one inverted conical baffle plate (8); the annular baffle plates (7) and the inverted conical baffle plate (8) are alternately arranged along the axial direction of a reaction tube (2); an upper opening and a lower opening are formed in each annular baffle plate (7); and the projection area of each upper opening in the horizontal direction is smaller than that of each lower opening in the horizontal direction. According to the technical scheme, the problem is well solved; and the method can be applied to industrial production of the propenyl ethanoate employing a propylene gas phase method.