US3336243A US321295A US32129563A US3336243A US 3336243 A US3336243 A US 3336243A US 321295 A US321295 A US 321295A US 32129563 A US32129563 A US 32129563A US 3336243 A US3336243 A US 3336243A Authority US United States Prior art keywords liquid copolymer phenolic acrylamide resin Prior art date 1963-11-04 Legal status (The legal status is an assumption and is not a … [provided by RefSeq, Oct 2008] 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. (See chemical bonding: Intermolecular forces for more information about hydrogen bonding.) Many phenolic compounds were discovered and used long before chemists were able to determine their structures. 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. Therefore, trivial names (i.e., vanillin, salicylic acid, pyrocatechol, resorcinol, cresol, hydroquinone, and eugenol) are often used for the most common phenolic compounds. Molecular Formula. Phenols are similar to alcohols but form stronger hydrogen bonds. For a detailed overview on identified uses and environmental releases, please consult the registered substance factsheet. Typically novolaks are prepared by the condensation of a … Phenol itself is the only one of the family that you are likely to need to know about for UK A level purposes. REACH registered substance data was upgraded on 9th November. If the substance is covered by more than one CLH entry (e.g. The ‘Substance identity’ section is calculated from substance identification information from all ECHA databases. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. This is unique source of information on the chemicals manufactured and imported in Europe. Phenol is the simplest member of a family of compounds in which an -OH group is attached directly to a benzene ring. Phenol formaldehyde; Structure of Bakelite. The examples provided are generic examples and may not apply to the specific substance you are viewing. 215–540–4, is covered by three harmonisations: 005–011–00–4; 005–011–01–1 and 005–011–02–9), CLH information cannot be displayed in the InfoCard as the difference between the CLH classifications requires manual interpretation or verification. 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. Properties of concern are calculated at four "levels" of certainty: The following properties of concern are calculated: The substance properties displayed in this section are derived from Harmonised classification and labelling (CLH) data, entries in the Candidate list of substances of very high concern for authorisation, the PBT assessment list, the ED assessment list, REACH registered dossier data and from notifications made under CLP. Typical mole ratios of formaldehyde to phenol range from 1.2 to 1.9 mol of formaldehyde per mol of phenol. ECHA has no data from registration dossiers on the precautionary measures for using this substance. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. C8H6O2. Phenol-formaldehyde resins are heat-resistant and … Furthermore, some substances can be found in an article, but with unlikely exposure (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. This site is not fully supported in Internet Explorer 7 (and earlier versions). 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]. Although they came into existence at the very start of the age of polymers, they continued to be developed into more and more applications. ChemIDplus - 9003-35-4 - KXGFMDJXCMQABM-UHFFFAOYSA-N - Phenol-formaldehyde resin - Similar structures search, synonyms, formulas, resource links, and other chemical information. The CLP Regulation uses the UN Global Harmonised System (GHS) and European Union Specific Hazard Statements (EUH). 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. CAS Number: 92-69-3 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. Molecular Formula C 7 H 8 O 2; Average mass 124.137 Da; Monoisotopic mass 124.052429 Da; ChemSpider ID 150578 Commercial materials are most commonly based on phenol itself; other phenols such as cresols, xylenols and resorcinol are used to a limited extent. Prepolymer resol resins with the molar ratio of phenol/formaldehyde 1/2.4 and different amounts of NaOH were synthesized and characterized using 13C … For example, chromic acid oxidizes most phenols to conjugated 1,4-diketones called quinones. In this interactive chemical reaction, graphene oxide (GO) was reduced to RGO by phenol, and simultaneously phenol was oxidized to benzoquinone. Individual Protection Measures, Such as Personal Protective Equipment Harmonisation is based on the substance’s physical, toxicological and eco-toxicological hazard assessment. 2017). Benzene is converted to isopropylbenzene (cumene) by treatment with propylene and an acidic catalyst. Like other alcohols, phenols undergo oxidation, but they give different types of products from those seen with aliphatic alcohols. More information about CAS and the CAS registry can be found here. Benzene is easily converted to chlorobenzene by a variety of methods, one of which is the Dow process. ECHA has no public registered data indicating whether or into which articles the substance might have been processed. Most functional groups can survive this technique, as long as they are stable in the presence of dilute acid. The resin curing behavior, molecular structure, bonding performance, and properties of resin-impregnated wood were investigated. However, substance notifications in the InfoCard are aggregated independently of the impurities and additives. 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 (*). 2-Propenoic acid, polymer with 4-(1,1-dimethylethyl)phenol, formaldehyde, 2,5-furandione, 2-methyloxirane, 4-nonylphenol and oxirane Valid Active 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. For example, vanillin, the principal flavouring in vanilla, is isolated from vanilla beans, and methyl salicylate, which has a characteristic minty taste and odour, is isolated from wintergreen. Molecular formula. 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. 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. Phenol, the cresols (methylphenols), and other simple alkylated phenols can be obtained from the distillation of coal tar or crude petroleum. This substance is used for the manufacture of: plastic products, mineral products (e.g. InfoCards are generated automatically based on the data available at the time of generation. The Support section provides tools and practical guidance to companies which have responsibilities under the EU chemicals legislation. More information about Classification and Labelling is available in the Regulations section of ECHA website. The molecular structure is based on structures generated from information available in ECHA’s databases. We apologise for the inconvenience in the meantime. Phenols are highly reactive toward electrophilic aromatic substitution, because the nonbonding electrons on oxygen stabilize the intermediate cation. Linear Formula: C 6 H 5 C 6 H 4 OH. Release to the environment of this substance can occur from industrial use: in the production of articles. To make more-complicated phenolic compounds, a more general synthesis is needed. This section is based on three sources for information (harmonised classification and labelling (CLH), REACH registrations and CLP notifications). If available, additional information on classification and labelling (C&L) is derived from REACH registration dossiers submitted by industry. 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. An effective explosive needs a high proportion of oxidizing groups such as nitro groups. It is possible that a harmonisation is introduced through an amendment to the CLP Regulation. What is the Classification and Labelling Inventory? 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. EC Inventory, C&L Inventory, Substance Evaluation - CoRAP, Registration dossier, Pre-Registration process, Other, Substances of very high concern identification, Recommendation for the Authorisation List, Getting started with EU chemicals legislation, Classification of substances and mixtures, Harmonised classification and labelling (CLH). Although phenols are often considered simply as aromatic alcohols, they do have somewhat different properties. In the presence of oxygen in the air, many phenols slowly oxidize to give dark mixtures containing quinones. 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. For example, phenol itself is used (in low concentrations) as a disinfectant in household cleaners and in mouthwash. disodium tetraborate EC no. 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 resins are heat-resistant and waterproof, though somewhat brittle. 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. Details of dossier compliance checks and testing proposal evaluation. The ‘Hazard classification’ and labelling section uses the signal word, pictogram(s) and hazard statements of the substance under the harmonised classification and labelling (CLH) as its primary source of information. Formaldehyde is an organic compound with the formula CH2O or HCHO and is one of the most important building blocks in the chemical industry. 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. This substance is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. Phenols are widely used in household products and as intermediates for industrial synthesis. Information on applicable regulatory frameworks is also automatically generated and may not be complete or up to date. Corrections? Data sources include IBM Watson Micromedex (updated 7 Dec 2020), Cerner Multum™ (updated 4 Dec 2020), ASHP (updated 3 Dec … 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). 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). Release to the environment of this substance can occur from industrial use: formulation of mixtures. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. Phenol-formaldehyde polymers are polymers formed by the interaction of a phenol, or a mixture of phenols, and formaldehyde. Warning! phenol-formaldehyde resin. 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]). 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. For example, phenols react with acids to give esters, and phenoxide ions (ArO−) can be good nucleophiles in Williamson ether synthesis. 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. Tham khảo hộp thông tin. 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. This substance is used in the following areas: formulation of mixtures and/or re-packaging and building & construction work. 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. Unexposed grains of silver bromide react more slowly than the exposed grains. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. 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. 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. The chemical equation is given below. 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. Butylated hydroxytoluene (BHT) has a much lower toxicity and is a common antioxidant in foods. Formaldehyde, polymer with (Chloromethyl) Oxirane and phenol. Substances may have impurities and additives that lead to different classifications. REACH registration dossiers have greater data requirements (such as supporting studies) than do notifications under CLP. Mixtures of phenols (especially the cresols) are used as components in wood preservatives such as creosote. For example, the systematic name for vanillin is 4-hydroxy-3-methoxybenzaldehyde. Picric acid (2,4,6-trinitrophenol) is an important explosive that was used in World War I. Formaldehyde, phenol polymer. 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. When information is available in all sources, the first two are displayed as a priority. It is the responsibility of the substance manufacturers and importers to consult official publications, e.g. In that case, the ATP (Adaptation to Technical Progress) number is displayed. 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. Compounds with other principal functional groups can be named with the hydroxyl group as a hydroxy substituent. Phenol may have been the first surgical antiseptic. Used in the production of resins, principally urea formaldehyde and phenol-formaldehyde, which are used to make cores and moulds for foundries. This information has not been reviewed or verified by ECHA, and may change without prior notice. This material is provided for educational purposes only and is not intended for medical advice, diagnosis or treatment. Substances which have been registered and can be placed on the EEA market by those companies with a valid registration. Public (risk management) activities co-ordination table. More information about the EC Inventory can be found here. Formaldehyde reacts with ammonia forms formamidine and water. 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 source of the information is mentioned in the introductory sentence of the hazard statements. 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. 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… 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. Phenolic resins are a group of the most versatile polymers yet invented. 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. By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Uses of Formaldehyde – CH 2 O. Updates? Our editors will review what you’ve submitted and determine whether to revise the article. Hydrolysis of chlorobenzene (the Dow process), https://www.britannica.com/science/phenol, National Center for Biotechnology Information - PubChem - Phenol. The structure of phenol. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. For readability purpose, only non-confidential use descriptors occurring in more than 5% of total occurrences are displayed. This website uses cookies to ensure you get the best experience on our websites. Most of the phenol used today is produced from benzene, through either hydrolysis of chlorobenzene or oxidation of isopropylbenzene (cumene). If at least one company has indicated that the substance classification is affected by impurities or additives, this will be indicated by an informative sentence. Systematic names are more useful, however, because a systematic name specifies the actual structure of the compound. the electronic edition of the Official Journal of the European Union. Author of. Substances indicated, in 2009, as being intended to be registered by at least one company in the EEA. Close Find out more on how we use cookies. 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. 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. This substance is used in the following products: coating products and fillers, putties, plasters, modelling clay. Chlorobenzene is hydrolyzed by a strong base at high temperatures to give a phenoxide salt, which is acidified to phenol. It covers their hazardous properties, classification and labelling, and information on how to use them safely. 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. If generated, an InChI string will also be generated and made available for searching. inside a watch) or with very low concentrations considered not to pose risks to human health or the environment. When the molar ratio of formaldehyde:phenol reaches one, in theory every phenol is linked together via methylene bridges, generating one single molecule, and the system is entirely crosslinked. The ability of phenols to form strong hydrogen bonds also enhances their solubility in water. 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. ECHA organises consultations to get feedback from all interested parties and to gather the widest possible range of scientific information for the regulatory processes. The polymerization of phenol with formaldehyde involves electrophilic aromatic substitution at the ortho and para positions of phenol (probably somewhat randomly), followed by cross-linking of the polymeric chains. The per substance REACH registration status is being calculated and will be made available as soon as possible. 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