23182-08-3

Upstream product

• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 107-13-1 acrylonitrile 

Downstream Products

• 69461-64-9 1-(1,3,4-trimethylcyclohex-3-en-1-yl)ethanone 

Relevant academic research and scientific papers

Evidence for 2-Hexene-1,6-diyl Diradicals Accompanying the Concerted Diels-Alder Cycloaddition of Acrylonitrile with Nonpolar 1,3-Dienes

The spontaneous reactions of a series of alkyl 1,3-dienes with acrylonitrile (AN) were investigated.Reproducible spontaneous copolymerizations were shown to compete with the expected concerted cycloadditions.For dienes which exist in s-cis/s-trans equilibrium, both copolymer and cycloadduct are formed.Kinetic measurements show that the alternating copolymerization and cycloaddition are two independent paralell second order reactions.With 1,3-cyclohexadiene and 1,2-dimethylenecyclohexane, for which s-gauche is in equilibrium with s-cis, copolymerization still competes with cycloaddition.The s-trans-locked verbenene forms only copolymer, while s-cis-locked cyclopentadiene and 1,2-dimethylenecyclopentane form only cycloadduct rapidly.Our explanation involves a 2-hexene-1,6-diradical, formed by combination between the terminal carbons of the s-gauche or s-trans diene and acrylonitrile.This does not cyclize but initiates copolymerization.Competitively s-cis conformer undergoes classical concerted addition.

Microwave-assisted organic synthesis in near-critical water at 300°C - A proof-of-concept study

Microwave-assisted organic synthesis in near-critical water (NCW) in the 270-300°C temperature range has been investigated in a dedicated multimode microwave reactor utilizing heavy-walled quartz reaction vessels. Several different known transformations such as the hydrolysis of esters or amides, the hydration of alkynes, Diels-Alder cycloadditions, pinacol rearrangements, and the Fischer indole synthesis were successfully performed in microwave-generated NCW without the addition of an acid or base catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Continuous Flow Synthesis under High-Temperature/High-Pressure Conditions Using a Resistively Heated Flow Reactor

A cheap, easy-to-build, and effective resistively heated reactor for continuous flow synthesis at high temperature and pressure is herein presented. The reactor is rapidly heated directly using an electric current and is capable of rapidly delivering temperatures and pressures up to 400 °C and 200 bar, respectively. High-temperature and high-pressure applications of this reactor were safely performed and demonstrated by selected transformations such as esterifications, transesterifications, and direct carboxylic acid to nitrile reactions using supercritical ethanol, methanol, and acetonitrile. Reaction temperatures were between 300 and 400 °C with excellent conversions and good to excellent isolated product yields. Examples of Diels-Alder reactions were also carried out at temperatures up to 300 °C in high yield. No additives or catalysts were used in the reactions.

Perfume systems

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perf

PERFUME SYSTEMS

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities' options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.

Translating high-temperature microwave chemistry to scalable continuous flow processes

A comparison between batch microwave and conventionally heated continuous flow scale-up protocols for three selected model reactions is presented. Using high-temperature/-pressure conditions as process intensification principles, reaction times for all three transformations were reduced to a few seconds or minutes at temperatures ranging from.

Sintered silicon carbide: A new ceramic vessel material for microwave chemistry in single-mode reactors

Silicon carbide (SiC) is a strongly microwave absorbing chemically inert ceramic material that can be utilized at extremely high temperatures due to its high melting point and very low thermal expansion coefficient. Microwave irradiation induces a flow of electrons in the semiconducting ceramic that heats the material very efficiently through resistance heating mechanisms. The use of SiC carbide reaction vessels in combination with a single-mode microwave reactor provides an almost complete shielding of the contents inside from the electromagnetic field. Therefore, such experiments do not involve electromagnetic field effects on the chemistry, since the semiconducting ceramic vial effectively prevents microwave irradiation from penetrating the reaction mixture. The involvement of electromagnetic field effects (specific/nonthermal microwave effects) on 21 selected chemical transformations was evaluated by comparing the results obtained in microwave-transparent Pyrex vials with experiments performed in SiC vials at the same reaction temperature. For most of the 21 reactions, the outcome in terms of conversion/purity/product yields using the two different vial types was virtually identical, indicating that the electromagnetic field had no direct influence on the reaction pathway. Due to the high chemical resistance of SiC, reactions involving corrosive reagents can be performed without degradation of the vessel material. Examples include high-temperature fluorine-chlorine exchange reactions using triethylamine trihydrofluoride, and the hydrolysis of nitriles with aqueous potassium hydroxide. The unique combination of high microwave absorptivity, thermal conductivity, and effusivity on the one hand, and excellent temperature, pressure and corrosion resistance on the other hand, makes this material ideal for the fabrication of reaction vessels for use in microwave reactors. Simulating conductive heat transfer in a microwave: Using reaction vials made out of strongly microwave-absorbing silicon carbide (SiC) in a microwave reactor simulates a conductively heated autoclave experiment due to efficient shielding of the electromagnetic field by the SiC vial. Advantages of SiC vials for microwave processing include their excellent corrosion resistance, thermal stability, and high thermal effusivity and conductivity.

Continuous-Flow microreactor Chemistry under High-Temperature/pressure

High-temperature organic synthesis can be performed under continuous-flow conditions in a stainless steel microtubular flow reactor capable of achieving temperatures of 350 °C and 200 bar. Under these extreme experimental environments transformations normally performed in a high-boiling solvent at reflux temperature - or under sealed-vessel microwave conditions - can be readily converted to a flow regime by using lower boiling solvents in or near their supercritical state. Wiley-VCH Verlag GmbH & Co, KGaA.

Silicon carbide passive heating elements in microwave-assisted organic synthesis

Microwave-assisted organic synthesis in nonpolar solvents is investigated utilizing cylinders of sintered silicon carbide (SiC)-a chemically inert and strongly microwave absorbing material-as passive heating elements (PHEs). These heating inserts absorb microwave energy and subsequently transfer the generated thermal energy via conduction phenomena to the reaction mixture. The use of passive heating elements allows otherwise microwave transparent or poorly absorbing solvents such as hexane, carbon tetrachloride, tetrahydrofuran, dioxane, or toluene to be effectively heated to temperatures far above their boiling points (200-250 °C) under sealed vessel microwave conditions. This opens up the possibility to perform microwave synthesis in unpolar solvent environments as demonstrated successfully for several organic transformations, such as Claisen rearrangements, Diels-Alder reactions, Michael additions, N-alkylations, and Dimroth rearrangements. This noninvasive technique is a particularly valuable tool in cases where other options to increase the microwave absorbance of the reaction medium, such as the addition of ionic liquids as heating aids, are not feasible due to an incompatibility of the ionic liquid with a particular substrate. The SiC heating elements are thermally and chemically resistant to 1500 °C and compatible with any solvent or reagent.

Diels-Alder reactions using supercritical water as an aqueous solvent medium

A variety of Diels-Alder reactions have been performed in supercritical water as a reaction medium. The rapid reaction of Diels-Alder reactions of cyclopentadiene and various electron poor dienophiles such as diethyl fumarate and acrylonitrile is observed in supercritical water, and leads to high yields of clean products without added catalysts.