89-72-5

Usage

Uses

Used in Chemical Industry:
2-sec-Butylphenol is used as a chemical intermediate for the preparation of resins, plasticizers, and surface-active agents, contributing to the development of a wide range of industrial products.
Used in Agricultural Industry:
2-sec-Butylphenol is used as a herbicide and insecticide, helping to control weeds and pests in agricultural settings, thereby improving crop yields and quality.
Used in Polymer Industry:
2-sec-Butylphenol is used as a polymerization inhibitor and stabilizer intermediate, playing a crucial role in controlling the polymerization process and enhancing the stability of polymer products.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, such as 2-sec-Butylphenol, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.

Hazard

Skin, eye, and upper respiratory tract irri- tant.

Health Hazard

o-sec-Butylphenol is a skin, eye, and respiratory irritant. Acute occupational exposures have resulted in mild respiratory irritation as well as skin burns.

Fire Hazard

2-sec-Butylphenol is combustible.

Flammability and Explosibility

Notclassified

Safety Profile

A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and skin contact. A severe skin and eye irritant. Combustible when exposed to heat or flame. To fight fire, use foam, spray, CO2, dry chemical. When heated to decomposition it emits acrid and irritating fumes. See also PHENOL and other butyl phenols

Potential Exposure

Butylphenols may be used as intermediates in manufacturing varnish and lacquer resins; as a germicidal agent in detergent disinfectants; as a pour point depressant, in motor-oil additives; de-emulsifier for oil; soap-antioxidant, plasticizer, fumigant, and insecticide

Shipping

UN2430 Alkylphenols, solid, n.o.s. (including C2-C12 homologues), Hazard class: 8; Labels: 8— Corrosive material

Incompatibilities

Vapors may form explosive mixture with air. These phenol/cresol materials can react with oxidizers; reaction may be violent. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may cause the gas to ignite and explode. Heat is also generated by the acid-base reaction with bases; such heating may initiate polymerization of the organic compound. React with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). These reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid and can explode when heated. Many phenols form metal salts that may be detonated by mild shock

InChI:InChI=1/C10H14O/c1-3-8(2)9-6-4-5-7-10(9)11/h4-8,11H,3H2,1-2H3/t8-/m1/s1

Upstream product

• 106-98-9 1-butylene 
• 108-95-2 phenol 
• 688-74-4 boric acid tributyl ester 
• 107-01-7 butene-2 
• 99-71-8 4-(1-methylpropyl)phenol 
• 71-36-3 butan-1-ol 
• 1849-18-9 2,4-di-(sec-butyl)phenol 
• 5892-47-7 2,4,6-tri-(sec-butyl)phenol 
• 54932-77-3 2,5-di-(sec-butyl)phenol 
• 1126-79-0 n-butyl phenyl ether 
• 3766-81-2 o-sec-butylphenyl-N-methylcarbamate 
• 78-93-3 butanone 
• 86119-84-8 phosphoric acid 
• 78-92-2 iso-butanol 

Downstream Products

• 159650-89-2 (+)-(S)-2-sec-butylphenol 
• 36383-18-3 (-)-(R)-2-sec-butylphenol 
• 88-85-7 dinoseb 
• 74926-91-3 2-sec-butyl-6-ethylphenol 
• 76343-98-1 2-(2, 4-dchlorophenoxy) acetic acid 
• 74926-88-8 2-allyl-6-(1-methylpropyl)phenol 
• 5331-25-9 1-(2-sec-butyl-phenoxy)-propan-2-ol 
• 60309-14-0 2-sec-butylphenyl-N-n-propylcarbamate 
• 33356-26-2 Thiophosphoric acid O-(2-sec-butyl-phenyl) ester S-(2-ethoxy-ethyl) ester O'-ethyl ester 
• 65261-74-7 3-(2-sec-Butyl-phenoxy)-N-isopropyl-benzamide 
• 33356-27-3 Thiophosphoric acid O-(2-sec-butyl-phenyl) ester O'-ethyl ester S-(2-isopropoxy-ethyl) ester 
• 38528-02-8 Thiophosphoric acid O-(2-sec-butyl-phenyl) ester O'-ethyl ester S-propyl ester 
• 92320-68-8 1-sec-Butyl-2-(4-chloro-butoxy)-benzene 
• 60309-13-9 Ethyl-carbamic acid 2-sec-butyl-phenyl ester 

Relevant academic research and scientific papers

METHOD FOR PREPARING P-HYDROXYMANDELIC COMPOUNDS IN STIRRED REACTORS

The process allows the preparation of a p-hydroxymandelic compound, comprising at least one step of condensation of at least one aromatic compound bearing at least one hydroxyl group and whose para position is free, with glyoxylic acid, the condensation reaction being performed in at least one reactor equipped with at least one mixing means, the specific mixing power being between 0.1 kW/m3 and 15 kW/m3. In addition, the invention also relates to a process for preparing a 4-hydroxyaromatic aldehyde by oxidation of this p-hydroxymandelic compound.

PROCESS FOR PRODUCING A T-BUTYL PHENOL FROM A C4 RAFFINATE STREAM

This invention relates to processes for producing various t-butyl phenols, such as 2,6-di-tert-butyl phenol and ortho-tert-butyl phenol, by selectively reacting phenol or a substituted phenol with an isobutylene-containing C4 raffinate stream. The 2,6-di-tert-butyl phenol and ortho-tert-butyl phenol can be transalkylated to form other tert-butyl phenols, such as para-tert-butyl phenol, 2,4-di-tert-butyl phenol.

Process for functionalising a phenolic compound carrying an electron-donating group

The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.

Competitive degradation and detoxification of carbamate insecticides by membrane anodic fenton treatment

The competitive degradation of six carbamate insecticides by membrane anodic Fenton treatment (AFT), a new Fenton treatment technology, was carried out in this study. The carbamates studied were dioxacarb, carbaryl, fenobucarb, promecarb, bendiocarb, and carbofuran. The results indicate that AFT can effectively degrade these insecticides in both single component and multicomponent systems. The carbamates compete for hydroxyl radicals, and their kinetics obey the previously developed AFT kinetic model quite well. Hydroxyl radical reaction rate constants were obtained, and they decrease in the following order: dioxacarb ≈ carbaryl > fenobucarb > promecarb > bendiocarb > carbofuran. The AFT is shown to have higher treatment efficiency at higher temperature. Degradation products of the carbamates were determined by gas chromatography/mass spectrometry, and it appears that degradation can be initiated by hydroxyl radical attack at different sites in the molecule, depending on the individual structure of the compound. Substituted phenols are the commonly seen degradation products. The AFT treatment can efficiently remove the chemical oxygen demand of the carbamate mixture, significantly increasing the biodegradability. Earthworm studies show that the AFT is also an effective detoxification process.

A fluorescence detection scheme for capillary electrophoresis of N- methylcarbamates with on-column thermal decomposition and derivatization

This paper describes a fluorescence detection method for N- methylcarbamate (NMC) pesticides in micellar electrokinetic chromatography (MEKC) separation. Fulfillment of the fluorescence detection hinged on the discovery that quaternary ammonium surfactants (particularly cetyltrimethylammonium bromide, CTAB), besides serving as hydrophobic pseudophases in MEKC, are also capable of catalyzing the thermal decomposition of NMCs to liberate methylamine. Thus, a multifunctional MEKC medium consisting of borate buffer, CTAB, and derivatizing components (o- phthaldialdehyde/2-mercaptoethanol) was formulated, which allowed first normal MEKC separation, subsequent thermal decomposition, and finally in situ derivatization of NMCs. With careful optimization of the operation conditions, fluorescence detection of 10 NMC compounds was achieved, with column efficiencies typically higher than 50 000 and detection limits better than 0.5 ppm. The present work represents an unprecedented effort in capillary electrophoresis (CE), in which an intact capillary was consecutively utilized as chambers for separation, decomposition, derivatization, and detection, without involving any interfacing features. The success in the implementation of such a detection system resulted in strikingly simple instrumentation as compared with the traditional postcolumn fluorescence determination of NMCs by reversed-phase HPLC. Similar protocols should be workable in the determination of a wide range of pesticides and pharmaceuticals in CE formats.

O-alkylation of phenolic compounds via rare earth orthophosphate catalysts

Carbocyclic/aliphatic ethers, for example anisole, quaicol, guaethol, p-methoxyphenol and ethylene dioxybenzene, are selectively prepared, in good yield, by reacting a phenolic compound, for example a phenol, hydroquinone, pyrocatechin, naphthol, or the like, with an alcohol, for example methanol, ethanol, isopropanol, ethylene glycol, etc., in gaseous phase, in the presence of a catalytically effective amount of a trivalent rare earth metal orthophosphate, for example a lanthanum, cerium or samarium orthophosphate, optionally doped with an alkali or alkaline earth metal, preferably cesium.

Metal cation-exchanged montmorillonite (Mn+-mont)-catalysed aromatic alkylation with aldehydes and ketones

The alkylation of aromatic compounds with aldehydes and ketones in the presence of a variety of metal cation-exchanged montmorillonites (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+, Zn2+, H+, Na+) has been investigated. Al3+- and Zr4+-Monts are revealed to be effective as catalysts, while no reaction takes place with Na+-mont. Al3+-Mont-catalysed alkylation of phenol with several aldehydes produces mainly or almost solely the corresponding gem-bis(hydroxyphenyl)alkanes (bisphenols) in good yields, while that with several ketones affords selectively the corresponding alkylphenols in moderate to good yields. The alkylation always occurs at the carbonyl carbon without any skeletal rearrangement and the kind of products depends much on the steric hindrance of an electrophilic intermediary carbocation. The alkylation of anisole, veratrole and p-cresol proceeds well, while that of toluene, benzene, chlorobenzene and nitrobenzene scarcely occurs.

Acidity effect in the regiochemical control of the alkylation of phenol with alkenes

Treatment of 1:1 mixtures of phenol and linear alkenes in the presence of an acidic promoter in CHCl3 at room temperature results in ortho-regioselective monoalkylation producing sec-alkylphenols in 48-60% yield. In similar reactions, branched alkenes lead exclusively to the corresponding para-tert-alkylphenols in 80-85% yield. Addition of increasing amounts of potassium phenolate to the reacting system reduces the protic acidity and promotes ortho-regioselective tert-alkylation. These results are tentatively explained in terms of competition of 'H-bond-template' and 'charge-controlled' mechanisms.

Rearrangement Alkyl Phenyl Ethers to Alkylphenols in the Presence of Cation-exchanged Montmorillonite (Mn+-Mont)

The rearrangement of alkyl phenyl ethers such as 4-phenoxybutan-2-one 1, 1-phenoxybutane 2a, 2-phenoxybutane 2b, 2-methyl-2-phenoxypropane 2c and phenoxycyclohexane 2d have been investigated in the presence of cation-exchanged montmorilonite (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+ and Zn2+).The ether 1 rearranged to 4-(4-hydroxyphenyl)butan-2-one 3 (raspberry ketone), the odour source of rasprerry, in 16-34percent GLC yield, where Zn2+-mont was the most effective catalyst.Similarly, other ethers 2a-d rearranged to the corresponding alkylphenols in up to 75percent isolated yield with good product selectivity, Al3+-mont being the catalyst of choice.Al3+-Mont was regenerated and resulted in the rearrangement of 2b, 2c and 2d.

Equilibria for the isomerization of (secondary-alkyl)phenols and cyclohexylphenols

Equilibria of a series of isomerizations and trans-alkylations of alkylphenols have been investigated in the liquid phase over a wide range of temperatures.Equilibria of isomerizations connected with the displacement of a substituent on a benzene nucleus were studied for secondary-butyl, -amyl, -hexyl, and cyclohexyl-phenols, and di-(secondary-butyl)phenols.Equilibria of positional isomerization connected with the displacement of an oxyphenyl radical in an alkyl chain were investigated for oxyphenyl-pentanes, -hexanes, -octanes, and -decanes.Trans-alkylation was investigated for di- and tri-(secondary-butyl)phenols.Values of ΔrH0m and ΔrS0m were found for all investigated reactions.An analysis was made of the thermodynamic quantities for the reactions.Enthalpies of formation of isopropylphenols (IPP) in the gaseous state were calculated.The values of ΔfH0m/(kJ * mol-1) were found at 298.15 K: o-IPP, -(175.3 +/- 2.4); p-IPP, -(175.3 +/- 2.4); m-IPP, -(175.3 +/-2.4); 2,4-di-IPP, -(254.1 +/- 2.8); 2,5-di-IPP, -(254.1 +/- 2.8); 2,6-di-IPP, -(254.1 +/- 2.8); 3,5-di-IPP, -(254.1 +/- 2.8); 2,4,6-tri-IPP, -(333.0 +/- 3.1).