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Industrial process
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The
Cumene_process
Organic compound
chemicals, primarily phenol and acetone (known as the cumene process). Commercial production of cumene is by Friedel–Crafts alkylation of benzene with propylene
Cumene
Chemical compound
but the cumene process is the dominant technology. Accounting for 95% of production (2003) is the cumene process, also called Hock process. It involves
Phenol
Aromatic organic chemical compound
cumene: C 6H 5CH(CH 3) 2 + O2 → C 6H 5C(CH 3) 2OOH Dicumyl peroxide is a side product. Cumene hydroperoxide is an intermediate in the cumene process for
Cumene_hydroperoxide
Organic compounds of the form R–O–O–R′
reagents in major commercial processes. In the cumene process, acetone and phenol are produced by decomposition of cumene hydroperoxide (Me = methyl):
Organic_peroxides
American chemical company
chemical manufacturer. It produces phenol in Frankford through the cumene process, where it is converted to caprolactam in Hopewell, polymerized to nylon
AdvanSix
Chemical reactor
oxidation of harmful chemical compounds in wastewater streams or of cumene in the cumene process. Also in the treatment of waste water trickle bed reactors are
Trickle-bed_reactor
Product of a reaction used in another
chemical intermediates. Cumene is made from benzene and propylene and used to make acetone and phenol in the cumene process. The cumene itself is of relatively
Chemical_intermediate
Process of producing goods
oil Burton process – cracking of hydrocarbons Cracking (chemistry) – the generic term for breaking up the larger molecules Cumene process – making phenol
Industrial_processes
Organic compound ((CH3)2CO); simplest ketone
acetone is produced via the cumene process; as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with
Acetone
Spontaneous oxidation by oxygen at normal temperature
chemicals are produced by autoxidation: in the cumene process, isopropylbenzene undergoes autoxidation to give cumene hydroperoxide. This compound is then converted
Autoxidation
Chemical product derived from petroleum
styrene as a monomer cumene – isopropylbenzene; a feedstock in the cumene process phenol – hydroxybenzene; often made by the cumene process acetone – dimethyl
Petrochemical
Chemical process for formation of phenol from benzene
and Poland. Rather than using the Raschig–Hooker process, some companies use the Hock or cumene process, which instead synthesizes acetone and phenol from
Raschig–Hooker_process
Chemical compound (CH3CH=CH2)
Propylene and benzene are converted to acetone and phenol via the cumene process. Propylene is also used to produce isopropyl alcohol (propan-2-ol),
Propylene
Simplest secondary alcohol
methods, as acetone is itself normally prepared from propene via the cumene process. IPA cost is primarily driven by raw material cost, and this way is
Isopropyl_alcohol
Chemical manufacturing plant in Australia
room. It is called the Cumene-Phenol plant because of the intermediate materials is cumene or isopropylbenzene in the cumene process. It produces equimolar
Huntsman_(chemical_plant)
Chemical compound
by-product of the cumene process. In this procedure, cumene is converted to its radical, through a reaction with oxygen. Normally these cumene radicals are
Α-Methylstyrene
Chemical compound
Therefore, this newer process without producing the acetone by-product appears attractive and is similar to the cumene process as a hydroperoxide is formed
Cyclohexanone
Chemical compound
dechlorination of polychlorophenols. Alternatively, it arises via the cumene process, which starts with the alkylation of chlorobenzene with propylene. Nomenclature
3-Chlorophenol
Organic compound (C6H5NH2); simplest aromatic amine
alternatively be prepared from ammonia and phenol derived from the cumene process. Many analogues and derivatives of aniline are known where the phenyl
Aniline
Chemical compound
cymene-cresol process, toluene is alkylated with propene to give p-cymene, which can be oxidatively dealkylated in a manner similar to the cumene process. p-Cresol
P-Cresol
Class of chemical compounds
large scale for the production of phenol by the Cumene process or Hock process for its cumene and cumene hydroperoxide intermediates. Such reactions rely
Hydroperoxide
Chemical compound
resins and fragrances. Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In the
Acetophenone
Chemical compound
material for the synthesis of acetone before the development of the cumene process: Ca(CH3COO)2 → CaCO3(s) + (CH3)2CO A saturated solution of calcium acetate
Calcium_acetate
Chemical compound (CH3C(O)CH2CH3)
isobutylbenzene, which is analogous to the industrial production of acetone. The cumene process can be modified to produce phenol and a mixture of acetone and butanone
Butanone
Chemical compound
industrially in two main ways. The most widely used route is similar to the cumene process in reaction mechanism and involves the dialkylation of benzene with
Hydroquinone
Set of reactions to attach substituents to an aromatic ring
from benzene and ethylene and for the production of cumene from benzene and propene in cumene process: Industrial production typically uses solid acids
Friedel–Crafts_reaction
Chemical compound
2-naphthol. 2-Naphthol can also be produced by a method analogous to the cumene process. The Sudan dyes are popular dyes noted for being soluble in organic
2-Naphthol
Chemical compound
cymene–cresol process, toluene is alkylated with propylene to give isomers of cymene, which can be oxidatively dealkylated analogous to the cumene process. Another
M-Cresol
Chemical compound
patent in 2009 for a process based on direct hydroalkylation of two benzene molecules. A route to phenol analogous to the cumene process begins with cyclohexylbenzene
Cyclohexylbenzene
Chemical used in plastics, xenoestrogen
and large amounts of both starting materials are available from the cumene process. As the only by-product is water, it may be considered an industrial
Bisphenol_A
Petrochemical process to break down saturated hydrocarbons in smaller molecules
Steam cracking is a petrochemical process in which saturated hydrocarbons are broken down ("cracked") into smaller, often unsaturated, hydrocarbons. It
Steam_cracking
Chemical compound
It is synthesized as a by-product in the autoxidation of cumene, which mainly affords cumene hydroperoxide. Alternatively, it can be produced by the addition
Dicumyl_peroxide
Crookesite Cryolite Crystal Crystal structure Cubic metre per mole Cumene process Cuprite Curium Cyanide Cyclopentadiene Cylindrite Cymophane Cytosine
Index_of_chemistry_articles
Chemical compound
dehydrated to give styrene, a useful monomer. Cumene hydroperoxide derived from oxygenation of cumene (isopropylbenzene), which affords cumyl alcohol
Propylene_oxide
Hydrocarbon compound (C6H6)
manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene
Benzene
Transfer of an alkyl group from one molecule to another
fundamental benzene-based feedstocks such as ethylbenzene (precursor to styrene), cumene (precursor to phenol and acetone), linear alkylbenzene sulfonates (for detergents)
Alkylation
Chemical compound
a viable option for smaller-capacity plants. Two processes were in use. In the single-step process developed by Sergey Lebedev, ethanol is converted
Butadiene
Chemical compound
as a solution in (aromatic) solvents, commonly toluene but also xylene, cumene, or mesitylene, Used in large excess, it activates precatalysts for alkene
Methylaluminoxane
Flammable liquid hydrocarbon mixture
reddish brown liquid that is a mixture of hydrocarbons (toluene, xylene, and cumene, etc.), could also be intended in some contexts. Generally, in pre 19th
Naphtha
Organic compound consisting entirely of hydrogen and carbon
xylenes, acetone together with phenol from cumene (isopropylbenzene), and cyclohexanone from cyclohexane. The process, which is called autoxidation, begins
Hydrocarbon
Measuring versus elapsed time the net rate of heat flow
hazards. For example, it has been used to determine autocatalytic kinetics of cumene hydroperoxide (CHP), an intermediate which is used in the chemical industry
Isothermal_microcalorimetry
Chemical substance
estimated to be 1.42 ug/Kg bw/day. Calcium xylene sulfonate and sodium cumene sulfonate have been shown to cause temporary, slight eye irritation in animals
Hydrotrope
Chemical compound
commercially in a process known as POSM (Lyondell Chemical Company) or SM/PO (Shell) for styrene monomer / propylene oxide. In this process, ethylbenzene
Styrene
Substance that can explode
5-Bis(trinitromethyl)tetrazole Chlorine oxides Copper(I) acetylide Copper(II) azide Cumene hydroperoxide Cycloprop(-2-)enyl nitrate (CXP or CPN) Cyanogen azide Cyanuric
Explosive
and plug fuel lines. Substituted aromatics such as toluene, xylene, and cumene, combined with limited benzene, solved the problem. By 1935, there were
History_of_gasoline
Chemical compounds in which hydroxyl group is attached directly to an aromatic ring
of benzene/toluene with propylene to form cumene then O 2 is added with H 2SO 4 to form phenol (Hock process). In addition to the reactions above, many
Phenols
isobutene, a reaction that proceeds via the carbocation (CH3)3C+. The process also leads to some triisobutenes and tetraisobutenes. The commercial material
Diisobutene
French chemist (1813–1891)
categorization of compounds more or less known or completely unknown like cumene, the latter having been discovered in collaboration with Gerhardt when they
Auguste_André_Thomas_Cahours
Chemical compound
the petroleum industry by alkylation of isobutene with isobutane. This process is conducted in alkylation units in the presence of acid catalysts. It
2,2,4-Trimethylpentane
Hydrocarbon compound containing one or more C=C bonds
in this process: CH2=CH2 + CH3CH=CHCH3 → 2 CH2=CHCH3 Transition metal catalyzed hydrovinylation is another important alkene synthesis process starting
Alkene
Family of organic compounds
naturally in coal tar oil and as byproducts of the crude oil refinery process. Others can be prepared by Friedel-Crafts alkylation. Alkylbenzenes used
Alkylbenzene
Chemical mixture
picolines, carbazole, quinolines benzene, toluene, and xylenes ("BTX") plus cumenes 1,2,3-Trimethylbenzene occurs naturally in coal tar. Many of these chemicals
Coal_tar
transportation or at a fixed facility, the accident origin (e.g., storage, process reactor, rail tank car, tank truck), the material involved, its amount
List of boiling liquid expanding vapor explosions
List_of_boiling_liquid_expanding_vapor_explosions
Hydrocarbon compound containing one or more C≡C bonds
aldehyde. This reaction was once a major industrial process but it has been displaced by the Wacker process. This reaction occurs in nature, the catalyst being
Alkyne
Organic compounds of the form >C=O
aerobic oxidation of cyclohexane. Acetone is prepared by air-oxidation of cumene. For specialized or small scale organic synthetic applications, ketones
Ketone
Classification of agents that are possibly carcinogenic to humans
salts Coconut oil diethanolamine condensate para-Cresidine Crotonaldehyde Cumene Cupferron Cycasin Dacarbazine Dantron (Chrysazin, 1,8-Dihydroxyanthraquinone)
IARC_group_2B
Enzyme family protecting the organism from oxidative damages
developed using various hydroperoxides as substrates for reduction, e.g. cumene hydroperoxide, tert-butyl hydroperoxide and hydrogen peroxide. The other
Glutathione_peroxidase
Petrochemical complex in Grangemouth, Scotland
"Rigidex 1 + 2". Then in 1960 a cumene-phenol plant was commissioned, utilising benzene from the Refinery and propylene in a process proprietary to the Distillers
Ineos_Grangemouth
Chemical compound
production of gasoline from methanol via the "MTG (Methanol to Gasoline) process". It is a relatively easily oxidized benzene derivative, with E1/2 of 2
Durene
Chemical compound
C3-Benzenes Trimethylbenzenes Mesitylene Pseudocumene Hemellitene Other Cumene n-Propylbenzene 4-Ethyltoluene C4-Benzenes Cymenes o-Cymene m-Cymene p-Cymene
Methylcyclopentane
Chemical compound
impurity, as heptane is usually used as a solvent. Nevertheless, by concise processes of distillation and refining, it is possible to separate 2-methylhexane
2-Methylhexane
Standard measure of the performance of an engine or aviation fuel
point in the piston's stroke. Knock occurs when the peak of the combustion process no longer occurs at the optimum moment for the four-stroke cycle. In a
Octane_rating
Saturated alicyclic hydrocarbon
give aromatic derivatives: The process provides a way to produce high octane gasoline. In another major industrial process, cyclohexanol is produced by
Cycloalkane
Chemical reaction
hydrocarbons: benzaldehyde from toluene, acrolein from propylene, acetone from cumene, cyclohexanone from cyclohexanol. In teaching laboratories and small scale
Alcohol_oxidation
Substances harmful to people, property or the environment
27 April 2016. Media related to Dangerous goods at Wikimedia Commons Processing Radioactive Materials - large set of images by the IAEA showing automated
Dangerous_goods
Hydrocarbon compound containing a non-aromatic ring with a C=C bond
groups from one or multiple terminal alkenes to form a cycloalkene. This process can be used to form cycloalkenes of either E or Z configurations, depending
Cycloalkene
Chemical compound
hydroformylation followed by hydrogenation of the dialdehyde. In a related process, 1,7-octadiene undergoes hydrocyanation to give dinitrile, which can be
1,7-Octadiene
Hydrocarbon compound; precursor to styrene and polystyrene
distillation process. In the 1980s a zeolite-based process using vapor phase alkylation offered a higher purity and yield. Then a liquid phase process was introduced
Ethylbenzene
Organic compounds with the formula (CH3)2C6H4
shifted to favor the highly valued p-xylene via the patented UOP-Isomar process or by transalkylation of xylene with itself or trimethylbenzene. These
Xylene
American engineering and defense contractor
expanded into steam pyrolysis, Orthoflow fluid catalytic cracking, phenol-from-cumene and coal-to-synthetic fuels technologies and the 1960s saw the growth in
KBR,_Inc.
Chemical compound
a series of distillation, adsorption or crystallization and reaction processes from the m-xylene, o-xylene, and ethylbenzene. Its melting point is the
P-Xylene
Industrial park in Marl, North Rhine-Westphalia, Germany
acrylate, butyl chloride, butyraldehyde Chlorine, copolyamides, copolyesters, cumene Dichlorobutane, dichloroethane Ethoxylate, ethylbenzene, ethyl chloride
Marl_Chemical_Park
Weed control herbicide
due to a merger). It is photosynthesis inhibitor. IPU is synthesized from cumene, which is treated with nitric acid (HNO3) to form p-nitrocumene. The nitrite
Isoproturon
Type of saturated hydrocarbon compound
catalysts. The thermal cracking process follows a homolytic mechanism with formation of free radicals. The catalytic cracking process involves the presence of
Alkane
Privately owned multinational chemicals company
plant in February 2011. The facility used a gasification fermentation process to convert cellulosic waste materials, such as yard and vegetative waste
Ineos
Hydrocarbon composed of multiple aromatic rings
particularly due to biofuel use in India and China. As of 2004, industrial processes and the extraction and use of fossil fuels made up slightly more than
Polycyclic aromatic hydrocarbon
Polycyclic_aromatic_hydrocarbon
Amount of heat released by combustion of a quantity of substance
water in a combustion process is in a liquid state after a combustion process. GPSA LHV This definition, used by Gas Processors Suppliers Association
Heat_of_combustion
Aromatic hydrocarbon
purification is done by any of the distillation or solvent extraction processes used for BTX aromatics (benzene, toluene, and xylene isomers). Toluene
Toluene
Chemical compound
functions in fish and algae. Its biodegradation has been heavily examined. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.
Pyrene
peroxide and other organic peroxides such as tert-butyl hydroperoxide and cumene hydroperoxide, peroxide stimulon gets activated. Studies of E. coli response
Oxidation_response
Hydrocarbon compound (C22H14) made of 5 fused benzene rings
including a one-pot-four-bond forming procedure which provided a solution-processable conjugated pentacene dimer (5c) which exhibited photoconductive gain
Pentacene
Chemical compound
montmorillonite or in cumene in the presence of methanesulfonic acid. In both variants yields of 95-97 % of itaconic anhydride are achieved. Another process of cyclizing
Itaconic_anhydride
Chemical compound
distillation to isolate naphthalene. The crude naphthalene resulting from this process is about 95% naphthalene by weight. The chief impurities are the sulfur-containing
Naphthalene
Chemical compound
of cumin and thyme. Significant amounts are formed in sulfite pulping process from the wood terpenes. p-Cymene is a common ligand for ruthenium. The
P-Cymene
Synthetic plant growth regulator
various processes such as the ripening of climacteric fruit, the opening of flowers (dehiscence process), and the shedding of leaves (abscission process). The
1-Methylcyclopropene
Polycyclic aromatic hydrocarbon composed of three fused benzene rings
Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes. This process involves electrophilic aromatic substitution using a tethered cyclohexanol
Phenanthrene
Chemical compound
Kumada coupling using nickel diphosphine catalysts. This mild and efficient process contrasted with older methods. C4-Benzenes Tamao, Kohei; Sumitani, Koji;
N-Butylbenzene
Tidal island in northeast England
of the West Saxon Anglo-Saxon Chronicle record: Her wæron reðe forebecna cumene ofer Norðhymbra land, ⁊ þæt folc earmlic bregdon, þæt wæron ormete þodenas
Lindisfarne
Chemical compound
other polycyclic aromatic hydrocarbons, is generated during combustion processes. Most human exposure is through tobacco smoke or ingestion of charred
Anthracene
Cage-like allotrope of carbon
thin films of carbon dust (soot). The soot had been generated by an arc-process between two graphite electrodes in a helium atmosphere where the electrode
Buckminsterfullerene
Chemical compound
toluene: CH3C6H5 + C2H4 → CH3C6H4C2H5 Over typical acid catalysts, this process gives a mixture of the 2-, 3-, and 4- isomers. Using a modified zeolite
4-Ethyltoluene
Covalent compound that contains two double bonds
butadiene and pentadiene are prepared by steam cracking. In a similar process, dicyclopentadiene is obtained from coal tars. Conjugated dienes can be
Diene
Type of chemical reaction
mechanisms of these systems is known. In combination with BINOL ligands and cumene hydroperoxide, lanthanide alkoxides can be used to epoxidize both trans
Asymmetric nucleophilic epoxidation
Asymmetric_nucleophilic_epoxidation
Chemical compound
2024, it was used to produce lower-energy excitations in solar cells in a process known as singlet fission. An interface layer between tetracene and silicon
Tetracene
Exposure to dangerous levels of airborne contaminants
cresol 4170-30-3 0241 Crotonaldehyde 143.5 mg/m3 50 ppm 123739 98-82-8 0170 Cumene 4428 mg/m3 900 ppm 98828 (10% Lower explosive limit LEL) 110-82-7 0242 Cyclohexane
Immediately dangerous to life or health
Immediately_dangerous_to_life_or_health
Conjugated hydrocarbon ring molecules with at least one triple bond
1002/anie.200901741 Dehydro[12]annulenes: Structures, Energetics, and Dynamic Processes Lawrence A. Januar, Vivian Huynh, Taylor S. Wood, Claire Castro, and William
Annulyne
Chemicals regulated in the United States
Colchicine 64-86-8 Conjugated estrogens – Creosotes – p-Cresidine 120-71-8 Cumene 98-82-8 Cupferron 135-20-6 Cyanazine 21725-46-2 Cycasin 14901-08-7 Cycloate
California Proposition 65 list of chemicals
California_Proposition_65_list_of_chemicals
Chemical compound
Valery V.; Sharpless, K. Barry (2002). "A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes"
1-Decyne
Chemical compound
temperatures over a suitable solid catalyst such as alumina. The mechanism of the process has been studied extensively, with several intermediates having been identified
Hexamethylbenzene
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