4-tert-Butylphenol

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4-tert-Butylphenol
4-tert-butylphenol.svg
Names
IUPAC name
4-tert-Butylphenol
Other names
p-tert-Butylphenol; Butylphen, Para tertiary butylphenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.436 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-679-0
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3
    Key: QHPQWRBYOIRBIT-UHFFFAOYSA-N
  • CC(C)(C)C1=CC=C(C=C1)O
Properties
C10H14O
Molar mass 150.221 g·mol−1
Appearancewhite solid
Density 0.908 g/cm3 (20 °C) [1]
Melting point 99.5 °C (211.1 °F; 372.6 K) [1]
Boiling point 239.8 °C (463.6 °F; 513.0 K) [1]
0.6 g/L (20 °C) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-tert-Butylphenol is an organic compound with the formula (CH3)3CC6H4OH. It is one of three isomeric tert-butyl phenols. It is a white solid with a distinct phenolic odor. It dissolves in basic water. [2]

Contents

Manufacture

It can be prepared by acid-catalyzed alkylation of phenol with isobutene, 2-tert-butylphenol being the major side product. It can be produced by diverse transalkylation reactions.

Uses

It major uses are in the production of epoxy resins and curing agents and also in polycarbonate resins. It has also found use in the production of phenolic resins. Another use is in the production of para tertiary butylphenol formaldehyde resin. It has also found use as a plasticizer.

Bisphenol A is difunctional and used to produce epoxy resin and polycarbonate. 4-tert-Butylphenol is monofunctional and so in polymer science terms, bisphenol A is a polymer chain extender but 4-tert-butylphenol is a chain stopper or sometimes called endcapper. It is thus use to control molecular weight by limiting chain growth.

4-tert-Butylphenol has an OH group and so it may be reacted with epichlorohydrin and sodium hydroxide to produce the glycidyl ether which is used in epoxy resin chemistry. This molecule has the CAS Registry number of 3101-60-8. [3] [4]

Laboratory reactions

Hydrogenation gives trans-4-tert-butylcyclohexanol. [5]

Controlled condensation with formaldehyde gives calixarenes. [6]

Safety

OSHA records show it as an irritant and has developed suggested test methods for its detection. [7] A European Union risk assessment report into the molecule dated May 2006 suggested it had potential depigmenting properties and was a potential endocrine disruptor. This was done under its EINECS number of 202-679-0. [8] Other papers have been published showing similar findings. [9]

Related Research Articles

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6H
5OH. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

<span class="mw-page-title-main">Phenol formaldehyde resin</span> Chemical compound

Phenol formaldehyde resins (PF) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commercial synthetic resins. They have been widely used for the production of molded products including billiard balls, laboratory countertops, and as coatings and adhesives. They were at one time the primary material used for the production of circuit boards but have been largely replaced with epoxy resins and fiberglass cloth, as with fire-resistant FR-4 circuit board materials.

<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.

<i>tert</i>-Butyllithium Chemical compound

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as solutions in hydrocarbons (such as pentane); it is not usually prepared in the laboratory.

<span class="mw-page-title-main">Epichlorohydrin</span> Chemical compound

Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

<span class="mw-page-title-main">Glycidol</span> Chemical compound

Glycidol is an organic compound with the formula HOCH2CHOCH2. The molecule contains both epoxide and alcohol functional groups. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

<span class="mw-page-title-main">Dimethylbenzylamine</span> Chemical compound

Dimethylbenzylamine is the organic compound with the formula C6H5CH2N(CH3)2. The molecule consists of a benzyl group, C6H5CH2, attached to a dimethylamino functional group. It is a colorless liquid. It is used as a catalyst for the formation of polyurethane foams and epoxy resins.

<span class="mw-page-title-main">Neopentyl glycol</span> Chemical compound

Neopentyl glycol is an organic chemical compound. It is used in the synthesis of polyesters, paints, lubricants, and plasticizers. When used in the manufacture of polyesters, it enhances the stability of the product towards heat, light, and water. By esterification reaction with fatty or carboxylic acids, synthetic lubricating esters with reduced potential for oxidation or hydrolysis, compared to natural esters, can be produced.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

<span class="mw-page-title-main">Propionaldehyde</span> Chemical compound

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a pungent and fruity odour. It is produced on a large scale industrially.

Para tertiary butylphenol formaldehyde resin also known as p-tert-butylphenol-formaldehyde resin (PTBP-FR) or 4-(1,1-dimethylethyl) phenol is a phenol-formaldehyde resin found in commercial adhesives, and in particular in adhesives used to bond leather and rubber. It has broad usage in a large variety of industries and can be found in many household items and textile products, and in particular it is used in the manufacture of shoes.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

<i>o</i>-Cresyl glycidyl ether Chemical compound

o-Cresyl glycidyl ether (ortho-cresyl glycidyl ether, o-CGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether. It has the formula C10H12O2 and the CAS Registry Number 2210-79-9. It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins. These are then further used in coatings, sealants, adhesives, composites and elastomers.

<span class="mw-page-title-main">Trimethylolpropane triglycidyl ether</span> Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. It has the formula C15H26O6 and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">C12–C13 alcohol glycidyl ether</span> Chemical compound

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family. It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 120547-52-6.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

<span class="mw-page-title-main">2,4,6-Tris(dimethylaminomethyl)phenol</span> Aromatic organic chemical

2,4,6-Tris(dimethylaminomethyl)phenol is an aromatic organic chemical that has tertiary amine and phenolic hydroxyl functionality in the same molecule. The formula is C15H27N3O and the CAS Registry Number is 90-72-2. It is REACH registered and the European Community Number is 202-013-9.

References

  1. 1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ↑ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   3527306730.
  3. ↑ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2021-04-19.
  4. ↑ "4-tert-butylphenyl glycidyl ether". www.wikidata.org. Retrieved 2021-04-19.
  5. ↑ Eliel, E. L.; Martin, R. J. L.; Nasipuri, D. (1967). "trans-4-t-BUTYLCYCLOHEXANOL". Organic Syntheses. 47: 16. doi:10.15227/orgsyn.047.0016.
  6. ↑ C. D. Gutsche, M. Iqbal (1990). "p-tert-Butylcalix[4]arene". Organic Syntheses. 68: 234. doi:10.15227/orgsyn.068.0234.
  7. ↑ "Sampling and Analytical Methods: p-tert-Butylphenol, PV2085". www.osha.gov. Retrieved 2021-04-16.
  8. ↑ European Union Risk Assessment report P-TERTIARY-BUTYLPHENOL May 2006 carried out in Norway
  9. ↑ Meier, Sonnich; Andersen, Thorny Cesilie; Lind-Larsen, Kristin; Svardal, Asbjørn; Holmsen, Holm (April 2007). "Effects of alkylphenols on glycerophospholipids and cholesterol in liver and brain from female Atlantic cod (Gadus morhua)". Comparative Biochemistry and Physiology. Toxicology & Pharmacology. 145 (3): 420–430. doi:10.1016/j.cbpc.2007.01.012. ISSN   1532-0456. PMID   17344102.
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