Aromatic compositions useful in various applications, such as aromatic fluid solvents and high temperature heat transfer fluids, are provided herein. Also provided are advantageous methods for obtaining the aromatic compositions, utilizing hydroalkylation of precursor aromatic hydrocarbons such as benzene, toluene, xylene, and the like. Particularly preferred aromatic compositions include one or more of cycloalkylaromatic, dicycloalkylaromatic, biphenyl, terphenyl, and diphenyl oxide compounds. The aromatic compositions may be blended with an aromatic solvent or other aromatic fluid comprising one or more of alkylnaphthalenes, alkylbenzenes, and naphthalene, e.g., to form a useful aromatic fluid solvent, or the aromatic compositions may be utilized as high temperature heat transfer fluids (with or without additional blend components).

A method of producing phenol and acetone can include: alkylating benzene with a C.sub.2-6 alkyl source in the presence of a zeolite catalyst to produce a C.sub.8-12 alkylbenzene; oxidizing the C.sub.8-12 alkylbenzene in the presence of an oxygen containing gas to produce a C.sub.8-12 alkylbenzene hydroperoxide; cleaving decomposing the C.sub.8-12 alkylbenzene hydroperoxide in the presence of an acid catalyst to produce phenol, a C.sub.3-6 ketone, and undesirable side products such as, but not limited to acetaldehyde, DMBA, acetophenone, AMS, AMS dimers, unidentified heavies, or a combination including at least one of the foregoing; and monitoring a concentration of the C.sub.8-12 alkylbenzene hydroperoxide in a process stream of a reactor in real time at a temperature and a pressure of the process stream; and in real time, controlling a parameter of the reactor and/or the cleaving decomposing in response to the concentration of the C.sub.8-12 alkylbenzene hydroperoxide.

A method of producing phenol and acetone can include: alkylating benzene with a C.sub.2-6 alkyl source in the presence of a zeolite catalyst to produce a C.sub.8-12 alkylbenzene; oxidizing the C.sub.8-12 alkylbenzene in the presence of an oxygen containing gas to produce a C.sub.8-12 alkylbenzene hydroperoxide; cleaving decomposing the C.sub.8-12 alkylbenzene hydroperoxide in the presence of an acid catalyst to produce phenol, a C.sub.3-6 ketone, and undesirable side products such as, but not limited to acetaldehyde, DMBA, acetophenone, AMS, AMS dimers, unidentified heavies, or a combination including at least one of the foregoing; and monitoring a concentration of the C.sub.8-12 alkylbenzene hydroperoxide in a process stream of a reactor in real time at a temperature and a pressure of the process stream; and in real time, controlling a parameter of the reactor and/or the cleaving decomposing in response to the concentration of the C.sub.8-12 alkylbenzene hydroperoxide.

The invention discloses a process for the oxidation of limonene, comprising the reaction of limonene with hydrogen peroxide in the presence of a catalyst containing atoms and/or ions of at least one metal, selected from the group consisting of molybdenum, tungsten, scandium, vanadium, titanium, lanthanum, zirconium, praseodymium, neodymium, samarium, europium, terbium, dysprosium, erbium or ytterbium, characterised in that the molecular weight of the catalyst is less than 2,000 g/mol and that the reaction is performed at a pH value of more than 7.5.

The invention discloses a process for the oxidation of limonene, comprising the reaction of limonene with hydrogen peroxide in the presence of a catalyst containing atoms and/or ions of at least one metal, selected from the group consisting of molybdenum, tungsten, scandium, vanadium, titanium, lanthanum, zirconium, praseodymium, neodymium, samarium, europium, terbium, dysprosium, erbium or ytterbium, characterised in that the molecular weight of the catalyst is less than 2,000 g/mol and that the reaction is performed at a pH value of more than 7.5.

Disclosed are processes and systems for oxidizing cycloalkylbenzene such as cyclohexylbenzene to make an oxygenate such as a hydroperoxide thereof. A liquid distributor having multiple liquid ingress ports is used for supplying a cycloalkylbenzene-containing liquid into an oxidation reactor in the form of liquid streams forming part of the reaction medium. A gas distributor distributing an O.sub.2-containing gas into the reaction medium in the form of gas streams is preferably located below the liquid distributor. Preferably the gas bubbles upwards in the reaction medium. The agitation and mixing provided by the liquid streams, gas streams/bubbles result in sufficient homogeneity of cycloalkylbenzene concentration, cycloalkylbenzene hydroperoxide concentration, dissolved oxygen concentration, and temperature in the liquid phase.

Disclosed are processes and systems for oxidizing cycloalkylbenzene such as cyclohexylbenzene to make an oxygenate such as a hydroperoxide thereof. A liquid distributor having multiple liquid ingress ports is used for supplying a cycloalkylbenzene-containing liquid into an oxidation reactor in the form of liquid streams forming part of the reaction medium. A gas distributor distributing an O.sub.2-containing gas into the reaction medium in the form of gas streams is preferably located below the liquid distributor. Preferably the gas bubbles upwards in the reaction medium. The agitation and mixing provided by the liquid streams, gas streams/bubbles result in sufficient homogeneity of cycloalkylbenzene concentration, cycloalkylbenzene hydroperoxide concentration, dissolved oxygen concentration, and temperature in the liquid phase.

Systems, methods, and apparatus for distribution of oxygen-containing gas within a gas-liquid oxidation reaction are provided herein. The invention is particularly suited for oxidation of liquid-phase organic reactants with oxidizing gas, such as the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide using an oxygen-containing gas. The oxygen-containing gas is distributed through a gas distributor and into a liquid-phase reaction medium within an oxidation reactor. In some aspects, this achieves a high degree of uniformity of oxygen concentration within the liquid-phase reaction medium. The gas distributor is disposed within a lower portion of the reactor, and may comprise a network of conduits in fluid communication with each other, which are arranged within a plane that is substantially parallel to a bottom surface of the reactor. A plurality of orifices are disposed on the conduits, such that oxygen-containing gas flows through the conduits and into the liquid-phase reaction medium via the orifices.

Systems, methods, and apparatus for distribution of oxygen-containing gas within a gas-liquid oxidation reaction are provided herein. The invention is particularly suited for oxidation of liquid-phase organic reactants with oxidizing gas, such as the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide using an oxygen-containing gas. The oxygen-containing gas is distributed through a gas distributor and into a liquid-phase reaction medium within an oxidation reactor. In some aspects, this achieves a high degree of uniformity of oxygen concentration within the liquid-phase reaction medium. The gas distributor is disposed within a lower portion of the reactor, and may comprise a network of conduits in fluid communication with each other, which are arranged within a plane that is substantially parallel to a bottom surface of the reactor. A plurality of orifices are disposed on the conduits, such that oxygen-containing gas flows through the conduits and into the liquid-phase reaction medium via the orifices.

Systems, methods, and apparatus for distribution of oxygen-containing gas within a gas-liquid oxidation reaction are provided herein. The invention is particularly suited for oxidation of liquid-phase organic reactants with oxidizing gas, such as the oxidation of cyclohexylbenzene to cyclohexylbenzene hydroperoxide using an oxygen-containing gas. The oxygen-containing gas is distributed through a gas distributor and into a liquid-phase reaction medium within an oxidation reactor. In some aspects, this achieves a high degree of uniformity of oxygen concentration within the liquid-phase reaction medium. The gas distributor is disposed within a lower portion of the reactor, and may comprise a network of conduits in fluid communication with each other, which are arranged within a plane that is substantially parallel to a bottom surface of the reactor. A plurality of orifices are disposed on the conduits, such that oxygen-containing gas flows through the conduits and into the liquid-phase reaction medium via the orifices.