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Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002
Minutes of the IUPAC Chemical Nomenclature and Structure Representation Division (VIII) Committee Meeting Boston, MA, USA, August 18, 2002 Members Present: Dr Stephen Heller, Prof Herbert Kaesz, Prof Dr Alexander Lawson, Prof G. Jeffrey Leigh, Dr Alan McNaught (President), Dr. Gerard Moss, Prof Bruce Novak, Dr Warren Powell (Secretary), Dr William Town, Dr Antony Williams Members Absent: Dr. Michael Dennis, Prof Michael Hess National representatives Present: Prof Roberto de Barros Faria (Brazil) The second meeting of the Division Committee of the IUPAC Division of Chemical Nomenclature and Structure Representation held in the Great Republic Room of the Westin Hotel in Boston, Massachusetts, USA was convened by President Alan McNaught at 9:00 a.m. on Sunday, August 18, 2002. 1.0 President McNaught welcomed the members to this meeting in Boston and offered a special welcome to the National Representative from Brazil, Prof Roberto de Barros Faria. He also noted that Dr Michael Dennis and Prof Michael Hess were unable to be with us. Each of the attendees introduced himself and provided a brief bit of background information. Housekeeping details regarding breaks and lunch were announced and an invitation to a reception from the U. S. National Committee for IUPAC on Tuesday, August 20 was noted. 2.0 The agenda as circulated was approved with the addition of a report from Dr Moss on the activity on his website. 3.0 The minutes of the Division Committee Meeting in Cambridge, UK, January 25, 2002 as posted on the Webboard (http://www.rsc.org/IUPAC8/attachments/MinutesDivCommJan2002.rtf and http://www.rsc.org/IUPAC8/attachments/MinutesDivCommJan2002.pdf) were approved with the following corrections: 3.1 The name Dr Gerard Moss should be added to the members present listing. -
C–H Arylation of Triphenylene, Naphthalene and Related Arenes Using Pd/C† Cite This: Chem
Chemical Science View Article Online EDGE ARTICLE View Journal | View Issue C–H arylation of triphenylene, naphthalene and related arenes using Pd/C† Cite this: Chem. Sci.,2015,6,1816 Karl D. Collins, Roman Honeker,‡ Suhelen Vasquez-C´ espedes,´ ‡ Dan-Tam D. Tang and Frank Glorius* A highly selective arylation of a number of polyaromatic hydrocarbons (PAHs) with aryliodonium salts and Pd/C as the only reagent is reported. The first C–H functionalization of triphenylene is explored, and proceeds at the most sterically hindered position. This non-chelate assisted C–H functionalization Received 4th October 2014 extends the reactivity profile of Pd/C and provides controlled access to p-extended PAHs, an important Accepted 19th December 2014 aspect of work towards the preparation of nanographenes. Mechanistic studies suggest in situ formation DOI: 10.1039/c4sc03051f of catalytically active insoluble nanoparticles, and that the reaction likely proceeds via a Pd(0)/Pd(II) type www.rsc.org/chemicalscience reaction manifold. Creative Commons Attribution 3.0 Unported Licence. Introduction precedent for the direct arylation of larger PAHs is reported. Seminal work by Oi and Inoue reported an effective arylation of Pd/C has long been established as an efficient catalyst in phenanthrene and uoranthene with aryltin trichlorides.10 One hydrogenation and cross-coupling reactions.1 Although sup- example of phenanthrene arylation has also been reported by ported catalysts are formally heterogeneous in nature, studies of Shi.11 Important studies by the group of Itami demonstrated a Pd/C suggest it typically acts as a reservoir of homogeneous more general solution (Scheme 1) using prepared boroxines as active catalytic species, following leaching of palladium from coupling partners.7d 1c,1e,2 the support into the solution. -
Polycyclic Aromatic Hydrocarbon Structure Index
NIST Special Publication 922 Polycyclic Aromatic Hydrocarbon Structure Index Lane C. Sander and Stephen A. Wise Chemical Science and Technology Laboratory National Institute of Standards and Technology Gaithersburg, MD 20899-0001 December 1997 revised August 2020 U.S. Department of Commerce William M. Daley, Secretary Technology Administration Gary R. Bachula, Acting Under Secretary for Technology National Institute of Standards and Technology Raymond G. Kammer, Director Polycyclic Aromatic Hydrocarbon Structure Index Lane C. Sander and Stephen A. Wise Chemical Science and Technology Laboratory National Institute of Standards and Technology Gaithersburg, MD 20899 This tabulation is presented as an aid in the identification of the chemical structures of polycyclic aromatic hydrocarbons (PAHs). The Structure Index consists of two parts: (1) a cross index of named PAHs listed in alphabetical order, and (2) chemical structures including ring numbering, name(s), Chemical Abstract Service (CAS) Registry numbers, chemical formulas, molecular weights, and length-to-breadth ratios (L/B) and shape descriptors of PAHs listed in order of increasing molecular weight. Where possible, synonyms (including those employing alternate and/or obsolete naming conventions) have been included. Synonyms used in the Structure Index were compiled from a variety of sources including “Polynuclear Aromatic Hydrocarbons Nomenclature Guide,” by Loening, et al. [1], “Analytical Chemistry of Polycyclic Aromatic Compounds,” by Lee et al. [2], “Calculated Molecular Properties of Polycyclic Aromatic Hydrocarbons,” by Hites and Simonsick [3], “Handbook of Polycyclic Hydrocarbons,” by J. R. Dias [4], “The Ring Index,” by Patterson and Capell [5], “CAS 12th Collective Index,” [6] and “Aldrich Structure Index” [7]. In this publication the IUPAC preferred name is shown in large or bold type. -
Temperature-Induced Oligomerization of Polycyclic Aromatic Hydrocarbons
www.nature.com/scientificreports OPEN Temperature-induced oligomerization of polycyclic aromatic hydrocarbons at ambient Received: 7 June 2017 Accepted: 10 July 2017 and high pressures Published: xx xx xxxx Artem D. Chanyshev 1,2, Konstantin D. Litasov1,2, Yoshihiro Furukawa3, Konstantin A. Kokh1,2 & Anton F. Shatskiy1,2 Temperature-induced oligomerization of polycyclic aromatic hydrocarbons (PAHs) was found at 500–773 K and ambient and high (3.5 GPa) pressures. The most intensive oligomerization at 1 bar and 3.5 GPa occurs at 740–823 K. PAH carbonization at high pressure is the fnal stage of oligomerization and occurs as a result of sequential oligomerization and polymerization of the starting material, caused by overlapping of π-orbitals, a decrease of intermolecular distances, and fnally the dehydrogenation and polycondensation of benzene rings. Being important for building blocks of life, PAHs and their oligomers can be formed in the interior of the terrestrial planets with radii less than 2270 km. High-pressure transformations of polycyclic aromatic hydrocarbons (PAHs) and benzene become extremely important due to wide applications for example in graphene- and graphene-based nanotechnology1–3, synthesis of organic superconductors4, 5, petroleum geoscience, origin of organic molecules in Universe and origin of life. In particular, PAHs were found in many space objects: meteorites6–8, cometary comae9, interstellar clouds and planetary nebulas10–12. Although the prevalent hypothesis for the formation of these PAHs is irradiation-driven polymerization of smaller hydrocarbons13, alternative explanation could be shock fragmentation of carbonaceous solid material11. PAH-bearing carbonaceous material could contribute to the delivery of extraterrestrial organic materials to the prebiotic Earth during the period of heavy bombardment of the inner Solar System from 4.5 to 3.8 Ga ago14–16. -
Summary of Information for ABC for Polycyclic Aromatic Hydrocarbons
Air Toxics Science Advisory Committee Summary of Information for ABC for Polycyclic Aromatic Hydrocarbons September 16, 2015 ATSAC Meeting #10 Presenter: Sue MacMillan, DEQ ATSAC lead Sue MacMillan | Oregon Department of Environmental Quality 26 Individual PAHs to Serve as Basis of ABC for Total PAHs Acenaphthene Cyclopenta(c,d)pyrene Acenaphthylene Dibenzo(a,h)anthracene Anthracene Dibenzo(a,e)pyrene Anthanthrene Dibenzo(a,h)pyrene Benzo(a)pyrene Dibenzo(a,i)pyrene Naphthalene Benz(a)anthracene Dibenzo(a,l)pyrene has separate Benzo(b)fluoranthene Fluoranthene ABC. Benzo(k)fluoranthene Fluorene Benzo( c)pyrene Indeno(1,2,3-c,d)pyrene Benzo(e)pyrene Phenanthrene Benzo(g,h,i)perylene Pyrene Benzo(j)fluoranthene 5-Methylchrysene Chrysene 6-Nitrochrysene Use of Toxic Equivalency Factors for PAHs • Benzo(a)pyrene serves as the index PAH, and has a documented toxicity value to which other PAHs are adjusted • Other PAHs adjusted using Toxic Equivalency Factors (TEFs), aka Potency Equivalency Factors (PEFs). These values are multipliers and are PAH-specific. • Once all PAH concentrations are adjusted to account for their relative toxicity as compared to BaP, the concentrations are summed • This summed concentration is then compared to the toxicity value for BaP, which is used as the ABC for total PAHs. Source of PEFs for PAHs • EPA provides a range of values of PEFs for each PAH • Original proposal suggested using upper-bound value of each PEF range as the PEF to use for adjustment of our PAHs • Average PEF value for each PAH is a better approximation of central tendency, and is consistent with the use of PEFs by other agencies • Result of using average, rather than upper-bound PEFs: slightly lower summed concentrations for adjusted PAHs, thus less apt to exceed ABC for total PAHs Documents can be provided upon request in an alternate format for individuals with disabilities or in a language other than English for people with limited English skills. -
Laboratory Spectroscopy and Astronomical Significance of The
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Repository@Nottingham Laboratory spectroscopy and astronomical significance of the fully-benzenoid PAH triphenylene and its cation V. Kofmana,b, P.J. Sarrec, R.E. Hibbinsc,d, I.L. ten Kateb, H. Linnartza aSackler Laboratory for Astrophysics, Leiden Observatory, Leiden University, PO Box 9513, 2300 RA Leiden, The Netherlands bDepartment of Earth Sciences, Utrecht University, Budapestlaan 4, 3584 CD Utrecht, The Netherlands cSchool of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom dDepartment of Physics, Norwegian University of Science and Technology, N-7491 Trondheim, Norway Abstract Triphenylene (C18H12) is a highly symmetric polycyclic aromatic hydrocarbon (PAH) molecule with a `fully-benzenoid' electronic structure. This confers a high chemical stability compared with PAHs of similar size. Although numerous infrared and UV-visible experimental spectroscopic and theoretical studies of a wide range PAHs in an astrophysical context have been conducted, triphenylene and its radical cation have received almost no attention. There exists a huge body of spectroscopic evidence for neutral and ionised PAHs in astrophysical sources, obtained principally through detection of infrared emission features that are characteristic of PAHs as a chemical class. However, it has so far not proved possible to identify spectroscopically a single isolated PAH in space, although PAHs including triphenylene have been detected -
Certificate of Analysis
National Institute of Standards & Technology Certificate of Analysis Standard Reference Material® 1597a Complex Mixture of Polycyclic Aromatic Hydrocarbons from Coal Tar This Standard Reference Material (SRM) is intended for use in the evaluation and validation of analytical methods for the determination of a natural, combustion-related mixture of polycyclic aromatic hydrocarbons (PAHs). SRM 1597a is isolated from a coal tar sample and dissolved in toluene. It is suitable for direct analysis (i.e., without sample cleanup or concentration) in the determination of PAHs using analytical techniques such as gas chromatography (GC), liquid chromatography (LC), or gas chromatography/mass spectrometry (GC/MS). This SRM may also be used to evaluate procedures for measurement of mutagenic activity of combustion-related mixtures of PAHs and related compounds. A unit of SRM 1597a consists of one 5 mL ampoule, containing 1.3 mL of material. Certified Mass Fraction Values: Certified values for concentrations, expressed as mass fractions, for 34 PAHs are provided in Table 1. The certified values are based on the agreement of results obtained at NIST from two or more chemically independent analytical techniques [1,2]. A NIST certified value is a value for which NIST has the highest confidence in its accuracy in that all known or suspected sources of bias have been investigated or accounted for by NIST. Reference Mass Fraction Values: Reference values for concentrations, expressed as mass fractions, are provided for 36 additional PAHs in Table 2 and for 10 polycyclic aromatic sulfur heterocycles (PASH) in Table 3. Reference values are given in Table 4 for the mutagenic activity of SRM 1597a. -
Nanostructural Origin of Blue Fluorescence in the Mineral Karpatite
Potticary, J. , Jensen, T. T., & Hall, S. R. (2017). Nanostructural origin of blue fluorescence in the mineral karpatite. Scientific Reports, 7(1), [9867]. https://doi.org/10.1038/s41598-017-10261-w Publisher's PDF, also known as Version of record License (if available): CC BY Link to published version (if available): 10.1038/s41598-017-10261-w Link to publication record in Explore Bristol Research PDF-document This is the final published version of the article (version of record). It first appeared online via Nature at https://www.nature.com/articles/s41598-017-10261-w. Please refer to any applicable terms of use of the publisher. University of Bristol - Explore Bristol Research General rights This document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/red/research-policy/pure/user-guides/ebr-terms/ www.nature.com/scientificreports OPEN Nanostructural origin of blue fuorescence in the mineral karpatite Received: 9 June 2017 Jason Potticary 1,2, Torsten T. Jensen 1,3 & Simon R. Hall1 Accepted: 7 August 2017 The colour of crystals is a function of their atomic structure. In the case of organic crystals, it is the Published: xx xx xxxx spatial relationships between molecules that determine the colour, so the same molecules in the same arrangement should produce crystals of the same colour, regardless of whether they arise geologically or synthetically. There is a naturally-occurring organic crystal known as karpatite which is prized for its beautiful blue fuorescence under ultra-violet illumination. -
Separation of 54 Pahs on an Agilent J&W Select PAH GC Column
Separation of 54 PAHs on an Agilent J&W Select PAH GC Column Application Note Author Introduction John Oostdijk Polycyclic aromatic hydrocarbons (PAHs) are compounds that contain two or more Agilent Technologies, Inc. aromatic rings. They are formed during incomplete combustion or pyrolysis of organic matter, industrial processes and cooking and food processing. PAHs are therefore analyzed in environmental and food samples. The difficulty in analyzing PAHs lies in separating PAH isomers. These isomers have the same chemical structure and same ion fragment and therefore cannot be separated by mass spectrometers. The Select PAH capillary column has enhanced selectivity towards PAHs, separating the isomers and enabling accurate PAH analysis. This application note describes an optimized oven program for the Select PAH column. In PAH analysis, there is a difference between the European (EU) and American (EPA) legislation. The legislations both describe a different set of PAHs and address different matrix origins. Table 1 lists the PAH regulated by EU and EPA legislation, including the potential interferences. For this application note, we chose a sample containing 54 PAHs to demonstrate the unique selectivity of the Select PAH. Conditions Peak MW Compound EPA SFC & CAS Technique: GC/MS, Triple Quad 610 EFSA PAHs Column: Select PAH, 30 m x 0.25 mm, df=0.15 µm (part number (15+1) CP7462) 7 154 Acenaphthene X 83-32-9 Sample Conc: approx 0.1-0.3 µg/mL 8 166 Fluorene X 86-73-7 Injection Volume: 1 μL Temperature: 70 °C (0.7 min), 85 °C/min, 180 -
Hydrogen Abstractions from Arylmethanes
AN ABSTRACT OF THE THESIS OF JERRY DEAN UNRUH for the DOCTOR OF PHILOSOPHY (Name) (Degree) in ORGANIC CHEMISTRY presented on ttr:e-( /9 2 O (Major) Title: HYDROGEN ABSTP ArTTnNs FROM ARV! ,TviWTHANES Redacted for Privacy Abstract approved: Dr. 'Gerald Jay Gleicher The relative rates of hydrogen abstraction from a series of 13 arylmethanes by the trichloromethyl radical were determined at 700. The attacking radical was generated from bromotrichloromethane us ing benzoyl peroxide as the initiator.The solvent was benzene- bromotrichloromethane. An excellent correlation, with a coefficient of 0.977, was obtained when the logs of the relative rates of hydrogen abstraction were plotted against the change in pi-binding energy be- tween the incipient radicals and the arylmethanes, if the pi-binding energy were calculated by the SCF approach. When the logs of the kinetic data were correlated with the change in pi-binding energy as calculated by the HMO approach, the correlation was poor, with a co- efficient of 0.855. A possible explanation for this difference might be the HZIckel method's complete neglect of electron interactions. The kinetic data were also plotted against the values of a param- eter,Z1E-3,which are indicative of the ground state electronic environment of the methyl group. A correlation was essentially non- existent.This, coupled with the excellent correlation with the changes in pi-binding energies, indicates that the transition state for hydrogen abstraction by the trichloromethyl radical must certainly lie near the intermediate radical with carbon-hydrogen bond breaking well advanced. The relative rates of hydrogen abstraction from a series of nine arylmethanes by the t-butoxy radical were also determined at 70o. -
Fluoranthene
) , "- United States Office of Water EPA 440/5-80-049 Environmental Protection Regulations and Standards October 1980 Agency Criteria and Standards Division Washington DC 20460 aEPA Ambient Water Quality Criteria for Fluoranthene ... AMBIENT WATER QUALITY CRITERIA FOR FLUORANTHENE Prepared By U.S. ENVIRONMENTAL PROTECTION AGENCY Office of Water Regulations and Standards Criteria and Standards Division Washington, D.C. Office of Research and Development Environmental Criteria and Assessment Office Cincinnati, Ohio Carcinogen Assessment Group Washington, D.C. Environmental Research Laboratories Corvalis, Oregon Duluth, Minnesota Gulf Breeze, Florida Narragansett, Rhode Island - -J i DISCLAIMER This report has been reviewed by the Environmental Criteria and Assessment Office, U.S. Environmental Protection Agency, and approved for publication. Mention of trade names or commercial products does not constitute endorsement or recommendation for use. AVAILABILITY NOTICE This document is available to the public through the National Technical Information Service, (NTIS), Springfield, Virginia 22161. ii FOREWORD Section 304 (a) (1) of the Clean Water Act of 1977 (P.L. 95-217), requires the Administrator of the Environmental Protection Agency to publish criteria for water quality accurately reflecting the latest scientific knowledge on the kind and extent of all identifiable effects on health and we 1fare wh ich may be expected from the presence of pollutants in any body of water, including ground water. Proposed water quality criteria for the 65 toxic pollutants listed under section 307 (a) (1) of the Cl ean Water Act were deve loped and a not ice of their availability was published for public comment on March 15, 1979 (44 FR 15926), July 25, 1979 (44 FR 43660), and October 1, 1979 (44 FR 56628). -
Ambient Air Pollution by Polycyclic Aromatic Hydrocarbons (PAH)
Ambient Air Pollution by Polycyclic Aromatic Hydrocarbons (PAH) Position Paper Annexes July 27th 2001 Prepared by the Working Group On Polycyclic Aromatic Hydrocarbons PAH Position Paper Annexes July 27th 2001 i PAH Position Paper Annexes July 27th 2001 Contents ANNEX 1...............................................................................................................................................................1 MEMBERSHIP OF THE WORKING GROUP .............................................................................................................1 ANNEX 2...............................................................................................................................................................3 Tables and Figures 3 Table 1: Physical Properties and Structures of Selected PAH 4 Table 2: Details of carcinogenic groups and measurement lists of PAH 9 Table 3: Review of Legislation or Guidance intended to limit ambient air concentrations of PAH. 10 Table 4: Emissions estimates from European countries - Anthropogenic emissions of PAH (tonnes/year) in the ECE region 12 Table 5: Summary of recent (not older than 1990) typical European PAH- and B(a)P concentrations in ng/m3 as annual mean value. 14 Table 6: Summary of benzo[a]pyrene Emissions in the UK 1990-2010 16 Table 7: Current network designs at national level (end-1999) 17 Table 8: PAH sampling and analysis methods used in several European countries. 19 Table 9: BaP collected as vapour phase in European investigations: percent relative to total (vapour