C8H6O2. Release to the environment of this substance can occur from industrial use: in the production of articles. Public (risk management) activities co-ordination table. This substance has been found in the following regulatory activities (directly, or inheriting the regulatory context of a parent substance): Welcome to the ECHA website. The association between water and phenol is unusually strong; when crystalline phenol is left out in a humid environment, it picks up enough water from the air to form liquid droplets. In 1865 the British surgeon Joseph Lister used phenol as an antiseptic to sterilize his operating field. Nitro groups are strongly deactivating (i.e., make the aromatic ring less reactive), however, and it is often difficult to add a second or third nitro group to an aromatic compound. Unexposed grains of silver bromide react more slowly than the exposed grains. The information is aggregated from the data coming from REACH substance registrations provided by industry. This substance is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites. ECHA maintains the C&L Inventory, but does not review or verify the accuracy of the information. For example, the systematic name for vanillin is 4-hydroxy-3-methoxybenzaldehyde. The CLP Regulation uses the UN Global Harmonised System (GHS) and European Union Specific Hazard Statements (EUH). The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. The common phenol hydroquinone is the component of photographic developer that reduces exposed silver bromide crystals to black metallic silver. ECHA has no public registered data indicating whether or into which articles the substance might have been processed. Besides serving as the generic name for the entire family, the term phenol is also the specific name for its simplest member, monohydroxybenzene (C 6 H 5 OH), also known as benzenol, or carbolic acid. According to the classification provided by companies to ECHA in CLP notifications this substance is toxic to aquatic life with long lasting effects, causes serious eye irritation, causes skin irritation and may cause an allergic skin reaction. [provided by RefSeq, Oct 2008] Substances indicated, in 2009, as being intended to be registered by at least one company in the EEA. Precautionary statements - describe recommended measures to minimise or prevent adverse effects resulting from exposure to a hazardous product or improper storage or handling of a hazardous product. Substances which have been registered and can be placed on the EEA market by those companies with a valid registration. Occupational exposure limit (OEL) values are derived within two legal frameworks that form an integral part of the EU’s mechanism for protecting the health of workers. This substance is used in the following areas: building & construction work. Therefore, trivial names (i.e., vanillin, salicylic acid, pyrocatechol, resorcinol, cresol, hydroquinone, and eugenol) are often used for the most common phenolic compounds. This information is only displayed if the substance is well-defined, its identity is not claimed confidential and there is sufficient information available in ECHA’s databases for ECHA’s algorithms to generate a molecular structure. The Prior Informed Consent Regulation administers the import and export of certain hazardous chemicals and places obligations on companies who wish to export these chemicals to non-EU countries. For example, chromic acid oxidizes most phenols to conjugated 1,4-diketones called quinones. This substance is used for the manufacture of: chemicals, plastic products, fabricated metal products, electrical, electronic and optical equipment and machinery and vehicles. However, substance notifications in the InfoCard are aggregated independently of the impurities and additives. Phenol/formaldehyde resins used to manufacture high-pressure laminates are typically produced by reacting phenol and formaldehyde by means of an alkaline catalyst such as sodium hydroxide [10]. The CLP Regulation makes sure that the hazards presented by chemicals are clearly communicated to workers and consumers in the European Union. The chemical formula of formaldehyde is CH2O: it has one carbon (C) atom, two hydrogen (H) atoms and one oxygen (O) atom. inside a watch) or with very low concentrations considered not to pose risks to human health or the environment. the products in which the substance may be used) may refer to uses as intermediate and under controlled conditions, for which there is no consumer exposure. The POPs Regulation bans or severely restricts the production and use of persistent organic pollutants in the European Union. Phenol-formaldehyde resin, also called phenolic resin, any of a number of synthetic resins made by reacting phenol (an aromatic alcohol derived from benzene) with formaldehyde (a reactive gas derived from methane). The per substance REACH registration status is being calculated and will be made available as soon as possible. Phenol-formaldehyde polymers are polymers formed by the interaction of a phenol, or a mixture of phenols, and formaldehyde. They are formed through the reaction of phenol with formaldehyde, followed by cross-linking of the polymeric chains. Note that for readability purposes, only the pictograms, signal words and hazard statements referred in more than 5% of the notifications under CLP are displayed. This is unique source of information on the chemicals manufactured and imported in Europe. Details of dossier compliance checks and testing proposal evaluation. Information on applicable regulatory frameworks is also automatically generated and may not be complete or up to date. in case of consumer and professional uses). InfoCards are generated automatically based on the data available at the time of generation. If the substance is covered by more than one CLH entry (e.g. This enzyme is an important component of cellular metabolism for the elimination of formaldehyde, a potent irritant and sensitizing agent that causes lacrymation, rhinitis, pharyngitis, and contact dermatitis. The resin curing behavior, molecular structure, bonding performance, and properties of resin-impregnated wood were investigated. Phenols occur either as colourless liquids or white solids at room temperature and may be highly toxic and caustic. This is why novolacs (F:P <1) do not harden without the addition of a crosslinking agents, and why resoles with the formula F:P >1 will. Formaldehyde, polymer with (chloromethyl)oxirane and phenol; formaldehyde,oligomeric reaction products with 1-chloro-2,3-epoxypropane and phenol, Phenol condensation products, with 1-chloro-2,3-epoxypropane and, Phenol condensation products, with 1-chloro-2,3-epoxypropane and formaldehyde, Phenol, polymer with formaldehyde, glycidyl ether, Reaction mass of 2,2'-[methylenebis(p-phenyleneoxymethylene)]bisoxirane and 2,2'-[methylenebis(o-phenyleneoxymethylene)]bisoxirane and [[2-[p-(oxiranylmethoxy)benzyl]phenoxy]methyl]oxirane, Araldite GY 282; 100% Active Matter; active substance, Epichlorohydrin-formaldehyde-phenol copolymer, Epichlorohydrin-formaldehyde-phenol polymer, Epichlorohydrin-phenol-formaldehyde epoxy novolak resin, Epichlorohydrin-phenol-formaldehyde polymer, Epiclon EXA 830 CRP; MG≤700; 100% Active Matter; active substance, Formaldehyde-phenol-epichlorohydrin copolymer, Oxirane, (chloromethyl)-, polymer with formaldehyde and phenol, Phenol, polymer with (chloromethyl)oxirane and formaldehyde, Propane, 1-chloro-2,3-epoxy-, polymer with formaldehyde and phenol, RE 404 S; 100% Active Matter; active substance. Close Find out more on how we use cookies. This material is provided for educational purposes only and is not intended for medical advice, diagnosis or treatment. Chlorobenzene is hydrolyzed by a strong base at high temperatures to give a phenoxide salt, which is acidified to phenol. Release to the environment of this substance can occur from industrial use: formulation of mixtures. Dynea produces a large volume of formaldehyde as an intermediate product, but we also supply formaldehyde in various consentrations and quality grades to the external market. BPR regulation aims to improve the functioning of the biocidal products market in the EU, while ensuring a high level of protection for humans and the environment. Lignin is a good candidate to replace phenol in the phenol formaldehyde resins’ formulation because (a) its polyphenolic structure is similar to that of phenolic resin (Fig. Substances for which classification and labelling data have been notified to ECHA by manufacturers or importers. Phenoxide ions, generated by treating a phenol with sodium hydroxide, are so strongly activated that they undergo electrophilic aromatic substitution even with very weak electrophiles such as carbon dioxide (CO2). 4 Fluctuations in price of phenol as a result of changes in oil price and concerns about chronic exposure of workers to phenol during the manufacturing process are the main reasons why over the last three decades many researchers have studied replacing phenol with biobased materials. Phenol dissolves to give a 9.3 percent solution in water, compared with a 3.6 percent solution for cyclohexanol in water. Professor of Chemistry, Whitman College, Walla Walla, Washington. For example, phenol itself is used (in low concentrations) as a disinfectant in household cleaners and in mouthwash. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. ECHA has no public registered data indicating whether or in which chemical products the substance might be used. Phenols with only one other substituent can be named using either the appropriate numbers or the ortho (1,2), meta (1,3), and para (1,4) system. If the substance was not covered by the EC Inventory, ECHA attributes a list number in the same format, starting with the numbers 6, 7, 8 or 9. This substance is used in the following products: coating products and fillers, putties, plasters, modelling clay. A milder, more general reaction is the diazotization of an arylamine (a derivative of aniline, C6H5NH2) to give a diazonium salt, which hydrolyzes to a phenol. phenol-formaldehyde resin. Picric acid (2,4,6-trinitrophenol) is an important explosive that was used in World War I. The structure of phenol. The molecular structure is based on structures generated from information available in ECHA’s databases. This section provides an overview of the calculated volume at which the substance is manufactured or imported to the European Economic Area (EU28 + Iceland, Liechtenstein and Norway). Phenol, formaldehyde polymer. Synonyms. This substance has not been registered under the REACH Regulation, therefore as yet ECHA has not received any data about this substance from registration dossiers. Phenols are not as acidic as carboxylic acids, but they are much more acidic than aliphatic alcohols, and they are more acidic than water. Less-toxic phenols, such as n-hexylresorcinol, have supplanted phenol itself in cough drops and other antiseptic applications. Registration, Evaluation, Authorisation and Restriction of Chemicals, Chemical Agents Directive and Carcinogens or Mutagens Directive, Formaldehyde, oligomeric reaction products with 1-chloro-2,3-epoxypropane and phenol, Substance Evaluation - CoRAP, Pre-Registration process, Formaldehyde, polymer with 2-(chloromethyl)oxirane and phenol, 2-(2-{[2-(oxiran-2-ylmethoxy)phenyl]methyl}phenoxymethyl)oxirane; 2-(2-{[4-(oxiran-2-ylmethoxy)phenyl]methyl}phenoxymethyl)oxirane; 2-(4-{[4-(oxiran-2-ylmethoxy)phenyl]methyl}phenoxymethyl)oxirane, 2-(chloromethyl)oxirane; formaldehyde; phenol, bisphenol-F-epichlorohydrin resin, MM=<700, Epichlorohydrin formaldehyde-phenol polymer; epoxy resin, epoxy phenol novolak resin: Phenol, polymer with formaldehyde, glycidyl ether or Epichlorohydrin-formaldehyde-phenol copolymer OR Formaldehyde, oligomeric reaction products with 1-chloro-2,3-epoxypropane and phenol, Formaldehyde, olgomeric reaction products with 1-chloro-2,3epoxypropane and phenol, FORMALDEHYDE, OLIGOMERIC REACTION PRODUCTS WITH 1-CHLORO-2,3- EPOXYPROPANE AND PHENOL, Formaldehyde, Oligomeric reaction products with 1-chloro2,3-epoxypropane and phenol, Formaldehyde, polymer with (chloromethyl)oxirane and phenol. Three nitro groups are more easily substituted onto phenol, because the strong activation of the hydroxyl group helps to counteract the deactivation of the first and second nitro groups. Commercial materials are most commonly based on phenol itself; other phenols such as cresols, xylenols and resorcinol are used to a limited extent. 1) (Forss and Fuhrmann1979), (b) the material comes from renewable resources, and (c) it can be used as a macromolecular material without previous treatment (Nimz 1983; Pang et al. Corrections? This substance is used in the following areas: formulation of mixtures and/or re-packaging and building & construction work. 28064-14-4 - Phenol, polymer with formaldehyde, glycidyl ether - Searchable synonyms, formulas, resource links, and other chemical information. Impurities or additives: When a specific critical property is calculated from industry data and where the majority of data submitters have indicated that the property relates to cases containing impurities and/or additives, then the respective critical property icon is modified with an asterisk (*). Phenols are common in nature; examples include tyrosine, one of the standard amino acids found in most proteins; epinephrine (adrenaline), a stimulant hormone produced by the adrenal medulla; serotonin, a neurotransmitter in the brain; and urushiol, an irritant secreted by poison ivy to prevent animals from eating its leaves. The date of the last update corresponds to the publication date of the InfoCard and not necessarily to the date in which the update occurred in the source data. Hydroquinone is used in developing photographic film by reducing activated (exposed to light) silver bromide (AgBr) to black metallic silver (Ag↓). A majority of data submitters agree this substance is Skin sensitising. If generated, an InChI string will also be generated and made available for searching. This section is based on three sources for information (harmonised classification and labelling (CLH), REACH registrations and CLP notifications). This information is only displayed if the substance is well–defined, its identity is not claimed confidential and there is sufficient information available in ECHA’s databases for ECHA’s algorithms to generate a molecular structure. Formaldehyde is made of methanol and phenol from benzene using the cumene process. Phenol, any of a family of organic compounds characterized by a hydroxyl (―OH) group attached to a carbon atom that is part of an aromatic ring. Much of the chemistry of phenols is like that of alcohols. Please upgrade your Internet Explorer to a newer version. The human genome contains several non-transcribed pseudogenes related to this gene. The cumene hydroperoxide reaction is fairly specific to phenol itself. To make more-complicated phenolic compounds, a more general synthesis is needed. Other relevant information includes the following: To see the full list of notified classifications and to get more information on impurities and additives relevant to classification please consult the C&L Inventory. It does not represent a new labelling, classification or hazard statement, neither reflect other factors that affect the susceptibility of the effects described, such as duration of exposure or substance concentration (e.g. The ‘Substance identity’ section is calculated from substance identification information from all ECHA databases. Hydrogen bonding results in higher melting points and much higher boiling points for phenols than for hydrocarbons with similar molecular weights. Updates? Systematic names are more useful, however, because a systematic name specifies the actual structure of the compound. ECHA has no data from registration dossiers on the precautionary measures for using this substance. Used in the production of resins, principally urea formaldehyde and phenol-formaldehyde, which are used to make cores and moulds for foundries. Phenol is the simplest member of a family of compounds in which an -OH group is attached directly to a benzene ring. Phenol, the cresols (methylphenols), and other simple alkylated phenols can be obtained from the distillation of coal tar or crude petroleum. Phenolic resins are a group of the most versatile polymers yet invented. More information about CAS and the CAS registry can be found here. The Waste Framework Directive aims to protect the environment and human health from the generation and management of waste and to improve efficient use of resources. Phenol-formaldehyde resins are inexpensive, heat-resistant, and waterproof, though somewhat brittle. Many of the more complex phenols used as flavourings and aromas are obtained from essential oils of plants. The molecular formula identifies each type of element by its chemical symbol and identifies the number of atoms of each element found in one discrete molecule of the substance. During this time formaldehyde was mainly used as an embalming agent or medical preservative, but these early uses represent less than 1% of total formaldehyde sales today. Phenols are similar to alcohols but form stronger hydrogen bonds. This site is not fully supported in Internet Explorer 7 (and earlier versions). Use descriptors are adapted from ECHA guidance to improve readability and may not correspond textually to descriptor codes described in Chapter R.12: Use Descriptor system of ECHA Guidance on information requirements and chemical safety assessment. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. Prepolymer resol resins with the molar ratio of phenol/formaldehyde 1/2.4 and different amounts of NaOH were synthesized and characterized using 13C … Let us know if you have suggestions to improve this article (requires login). Tool showing an overview of substances in various key regulatory processes that authorities are working on. Formaldehyde, phenol polymer. The type of uses and classifications may vary between different submissions to ECHA and for a full understanding it is recommended to consult the source data. Although phenols are often considered simply as aromatic alcohols, they do have somewhat different properties. For readability purpose, only non-confidential use descriptors occurring in more than 5% of total occurrences are displayed. The CLP Regulation ensures that the hazards presented by chemicals are clearly communicated to workers and consumers in the European Union through classification and labelling of chemicals. Substances may have impurities and additives that lead to different classifications. Formaldehyde, polymer with 3-chloro-1-propene and phenol | C10H13ClO2 | CID 168810 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. The Dow process is somewhat more general, but the stringent conditions required often lead to low yields, and they may destroy any other functional groups on the molecule. Oxidation yields a hydroperoxide (cumene hydroperoxide), which undergoes acid-catalyzed rearrangement to phenol and acetone. We apologise for the inconvenience in the meantime. The use information is displayed per substance life cycle stage (consumer use, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites or in manufacturing). Typical mole ratios of formaldehyde to phenol range from 1.2 to 1.9 mol of formaldehyde per mol of phenol. Furthermore, some substances can be found in an article, but with unlikely exposure (e.g. disodium tetraborate EC no. This substance is used for the manufacture of: plastic products, mineral products (e.g. For example, phenol (molecular weight [MW] 94, boiling point [bp] 182 °C [359.6 °F]) has a boiling point more than 70 degrees higher than that of toluene (C6H5CH3; MW 92, bp 111 °C [231.8 °F]). Most functional groups can survive this technique, as long as they are stable in the presence of dilute acid. 2017). The CAS number is the substance numerical identifier assigned by the Chemical Abstracts Service, a division of the American Chemical Society, to substances registered in the CAS registry database. Phenols are highly reactive toward electrophilic aromatic substitution, because the nonbonding electrons on oxygen stabilize the intermediate cation. ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA organises consultations to get feedback from all interested parties and to gather the widest possible range of scientific information for the regulatory processes. Other phenols obtained from plants include thymol, isolated from thyme, and eugenol, isolated from cloves. Amines, tallow alkyl, reaction products with formaldehyde and phenol, ethoxylated Unknown: TSCA Inv Amines, tallow alkyl, reaction products with formaldehyde and phenol, ethoxylated Valid: Inactive 2020 CDR Full Exempt Amines, tallow alkyl, reaction products with formaldehyde and phenol… InfoCards are updated when new information is available. Thus, they are more soluble in water than are alcohols and have higher boiling points. The chemical equation is given below. Besides serving as the generic name for the entire family, the term phenol is also the specific name for its simplest member, monohydroxybenzene (C6H5OH), also known as benzenol, or carbolic acid. Such notifications are required for hazardous substances, mixtures, or articles, manufactured or imported at over 1 kg per annum. Other substituted phenols are used in the dye industry to make intensely coloured azo dyes. A substance identified primarily by an EC or list number may be linked with more than one CAS number, or with CAS numbers that have been deleted. For a detailed overview on identified uses and environmental releases, please consult the registered substance factsheet. In that case, the ATP (Adaptation to Technical Progress) number is displayed. REACH registration dossiers have greater data requirements (such as supporting studies) than do notifications under CLP. Individual Protection Measures, Such as Personal Protective Equipment Its chemical formula can also be … Phenol-formaldehyde resins are heat-resistant and … Additionally, if available, information on the use of the substance and how consumers and workers are likely to be exposed to it can also be displayed here. Formaldehyde reacts with ammonia forms formamidine and water. Molecular Formula C 7 H 8 O 2; Average mass 124.137 Da; Monoisotopic mass 124.052429 Da; ChemSpider ID 150578 The EC Number is the numerical identifier for substances in the EC Inventory. The described Product category (i.e. Phenolic resins account for a large portion of phenol production. The simplest way to draw the structure of phenol is: Benzene is converted to isopropylbenzene (cumene) by treatment with propylene and an acidic catalyst. The most obvious difference is the enhanced acidity of phenols. This information has not been reviewed or verified by ECHA, and may change without prior notice. In industry, phenol is used as a starting material to make plastics, explosives such as picric acid, and drugs such as aspirin. Phenol-formaldehyde resin. Tham khảo hộp thông tin. The purpose of the information provided under this section is to highlight the substance hazardousness in a readable format. In this interactive chemical reaction, graphene oxide (GO) was reduced to RGO by phenol, and simultaneously phenol was oxidized to benzoquinone. Butylated hydroxytoluene (BHT) has a much lower toxicity and is a common antioxidant in foods. Unlike simple alcohols, most phenols are completely deprotonated by sodium hydroxide (NaOH). Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Molecular Formula. If the hydroxyl group is the principal functional group of a phenol, the compound can be named as a substituted phenol, with carbon atom 1 bearing the hydroxyl group. Author of. If a substance is classified under multiple CLH entries, a link to the C&L Inventory is provided to allow users to view CLH information associated with the substance and no text is automatically generated for the InfoCard. An oxygen atom normally forms two σ bonds with other atoms; the water molecule, H2O, is the... Get exclusive access to content from our 1768 First Edition with your subscription. Formaldehyde is an organic compound with the formula CH2O or HCHO and is one of the most important building blocks in the chemical industry. Prepolymer resol resins with different phenol/formaldehyde/NaOH molar ratios were synthesized and characterized by technical analysis as well as by C-13 NMR spectra for samples in CD3OD solution. Phenol formaldehyde; Structure of Bakelite. Phenol is quite toxic, however, and concentrated solutions cause severe but painless burns of the skin and mucous membranes. Here you can find all of the regulations and regulatory lists in which this substance appears, according to the data available to ECHA. Phenol, polymer with formaldehyde. The EC or list number is the primary substance identifier used by ECHA. The ‘Hazard classification and labelling’ section shows the hazards of a substance based on the standardised system of statements and pictograms established under the CLP (Classification Labelling and Packaging) Regulation. Formaldehyde was initially manufactured in small quantities (5-20kg) for use in a few factories and university laboratories, but improvements to the manufacturing process eventually led to large-scale production of formaldehyde. Our editors will review what you’ve submitted and determine whether to revise the article. phenol formaldehyde. Compounds with other principal functional groups can be named with the hydroxyl group as a hydroxy substituent. This section provides links to the list of precautions (precautionary statements) and to the guidance on safe use, if they have been provided in REACH registration dossiers. If no EU harmonised classification and labelling exists and the substance was not registered under REACH, information derived from classification and labelling (C&L) notifications to ECHA under CLP Regulation is displayed under this section. Although they came into existence at the very start of the age of polymers, they continued to be developed into more and more applications. Information on precautionary measures and the safe use is submitted by the registrant of a substance and the registrant is solely responsible for its accuracy and completeness. In this study, three different boron compounds were used together with alkaline catalyst to synthesize phenol formaldehyde (PF) resole resins in situ. The ‘Properties of concern’ section shows ECHA-assigned graphical indicators for certain substance properties that are regarded as being of relevance or importance to human health and/or the environment based on the information provided to the Agency. Benzene is easily converted to chlorobenzene by a variety of methods, one of which is the Dow process. Abstract. CAS Number: 92-69-3 REACH regulation aims to improve the protection of human health and the environment from the risks that can be posed by chemicals. These notifications can be provided by manufacturers, importers and downstream users. More information about Classification and Labelling is available in the Regulations section of ECHA website. Under the trade name Bakelite, a phenol-formaldehyde resin was one of the earliest plastics, invented by American industrial chemist Leo Baekeland and patented in 1909. The molecular formula identifies each type of element by its chemical symbol and identifies the number of atoms of each element found in one discrete molecule of the substance. the electronic edition of the Official Journal of the European Union. Similar to alcohols, phenols have hydroxyl groups that can participate in intermolecular hydrogen bonding; in fact, phenols tend to form stronger hydrogen bonds than alcohols. What is the Classification and Labelling Inventory? Most of the phenol used today is produced from benzene, through either hydrolysis of chlorobenzene or oxidation of isopropylbenzene (cumene). More information about the EC Inventory can be found here. For example, the systematic name for thymol is 5-methyl-2-isopropylphenol. Many phenolic compounds were discovered and used long before chemists were able to determine their structures. Molecular Weight: 170.21. Data sources include IBM Watson Micromedex (updated 7 Dec 2020), Cerner Multum™ (updated 4 Dec 2020), ASHP (updated 3 Dec … Warning! The source of the information is mentioned in the introductory sentence of the hazard statements. Uses of Formaldehyde – CH 2 O. If available, additional information on classification and labelling (C&L) is derived from REACH registration dossiers submitted by industry. ECHA has no public registered data indicating whether or in which chemical products the substance might be used. Please note: Precautionary measures and guidance on safe use concern the use and handling of the specific substance as such, not of the presence of the substance in other articles or mixtures. It is possible that a harmonisation is introduced through an amendment to the CLP Regulation. Formaldehyde, polymer with (Chloromethyl) Oxirane and phenol. The ability of phenols to form strong hydrogen bonds also enhances their solubility in water. 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