Toxicity of Possible Impurities and By-Products in Fluorocarbon Products
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Problem Formulation of the Risk Evaluation for Perchloroethylene (Ethene, 1,1,2,2-Tetrachloro)
EPA Document# EPA-740-R1-7017 May 2018 DRAFTUnited States Office of Chemical Safety and Environmental Protection Agency Pollution Prevention Problem Formulation of the Risk Evaluation for Perchloroethylene (Ethene, 1,1,2,2-Tetrachloro) CASRN: 127-18-4 May 2018 TABLE OF CONTENTS ABBREVIATIONS ............................................................................................................................ 8 EXECUTIVE SUMMARY .............................................................................................................. 11 1 INTRODUCTION .................................................................................................................... 14 1.1 Regulatory History ..................................................................................................................... 16 1.2 Assessment History .................................................................................................................... 16 1.3 Data and Information Collection ................................................................................................ 18 1.4 Data Screening During Problem Formulation ............................................................................ 19 2 PROBLEM FORMULATION ................................................................................................. 20 2.1 Physical and Chemical Properties .............................................................................................. 20 2.2 Conditions of Use ...................................................................................................................... -
Fluorinated Polymers As Smart Materials for Advanced Biomedical Applications
polymers Review Fluorinated Polymers as Smart Materials for Advanced Biomedical Applications Vanessa F. Cardoso 1,2,* ID , Daniela M. Correia 3,4, Clarisse Ribeiro 1,5 ID , Margarida M. Fernandes 1,5 and Senentxu Lanceros-Méndez 4,6 1 Centro/Departamento de Física, Universidade do Minho, 4710-057 Braga, Portugal; cribeiro@fisica.uminho.pt (C.R.); margaridafernandes@fisica.uminho.pt (M.M.F.) 2 CMEMS-UMinho, Universidade do Minho, DEI, 4800-058 Guimaraes, Portugal 3 Departamento de Química e CQ-VR, Universidade de Trás-os-Montes e Alto Douro, 5001-801 Vila Real, Portugal; [email protected] 4 BCMaterials, Basque Center for Materials, Applications and Nanostructures, UPV/EHU Science Park, 48940 Leioa, Spain; [email protected] 5 CEB—Centre of Biological Engineering, University of Minho, 4710-057 Braga, Portugal 6 IKERBASQUE, Basque Foundation for Science, 48013 Bilbao, Spain * Correspondence: [email protected]; Tel.: +351-253-60-40-73 Received: 11 January 2018; Accepted: 6 February 2018; Published: 8 February 2018 Abstract: Fluorinated polymers constitute a unique class of materials that exhibit a combination of suitable properties for a wide range of applications, which mainly arise from their outstanding chemical resistance, thermal stability, low friction coefficients and electrical properties. Furthermore, those presenting stimuli-responsive properties have found widespread industrial and commercial applications, based on their ability to change in a controlled fashion one or more of their physicochemical properties, in response to single or multiple external stimuli such as light, temperature, electrical and magnetic fields, pH and/or biological signals. In particular, some fluorinated polymers have been intensively investigated and applied due to their piezoelectric, pyroelectric and ferroelectric properties in biomedical applications including controlled drug delivery systems, tissue engineering, microfluidic and artificial muscle actuators, among others. -
Cyclobutane Derivatives in Drug Discovery
Cyclobutane Derivatives in Drug Discovery Overview Key Points Unlike larger and conformationally flexible cycloalkanes, Cyclobutane adopts a rigid cyclobutane and cyclopropane have rigid conformations. Due to the ring strain, cyclobutane adopts a rigid puckered puckered conformation Offer ing advantages on (~30°) conformation. This unique architecture bestowed potency, selectivity and certain cyclobutane-containing drugs with unique pharmacokinetic (PK) properties. When applied appropriately, cyclobutyl profile. scaffolds may offer advantages on potency, selectivity and pharmacokinetic (PK) profile. Bridging Molecules for Innovative Medicines 1 PharmaBlock designs and Cyclobutane-containing Drugs synthesizes over 1846 At least four cyclobutane-containing drugs are currently on the market. cyclobutanes, and 497 Chemotherapy carboplatin (Paraplatin, 1) for treating ovarian cancer was cyclobutane products are prepared to lower the strong nephrotoxicity associated with cisplatin. By in stock. CLICK HERE to replacing cisplatin’s two chlorine atoms with cyclobutane-1,1-dicarboxylic find detailed product acid, carboplatin (1) has a much lower nephrotoxicity than cisplatin. On information on webpage. the other hand, Schering-Plough/Merck’s hepatitis C virus (HCV) NS3/4A protease inhibitor boceprevir (Victrelis, 2) also contains a cyclobutane group in its P1 region. It is 3- and 19-fold more potent than the 1 corresponding cyclopropyl and cyclopentyl analogues, respectively. Androgen receptor (AR) antagonist apalutamide (Erleada, 4) for treating castration-resistant prostate cancer (CRPC) has a spirocyclic cyclobutane scaffold. It is in the same series as enzalutamide (Xtandi, 3) discovered by Jung’s group at UCLA in the 2000s. The cyclobutyl- (4) and cyclopentyl- derivative have activities comparable to the dimethyl analogue although the corresponding six-, seven-, and eight-membered rings are slightly less 2 active. -
Recent Advances in the Total Synthesis of Cyclobutane-Containing Natural Products Cite This: Org
Volume 7 | Number 1 | 7 January 2020 ORGANIC CHEMISTRY FRONTIERS rsc.li/frontiers-organic ORGANIC CHEMISTRY FRONTIERS View Article Online REVIEW View Journal | View Issue Recent advances in the total synthesis of cyclobutane-containing natural products Cite this: Org. Chem. Front., 2020, 7, 136 Jinshan Li,†a Kai Gao, †a Ming Bianb and Hanfeng Ding *a,c Complex natural products bearing strained cyclobutane subunits, including terpenoids, alkaloids and steroids, not only display fascinating architectures, but also show potent biological activities. Due to their unique structures as critical core skeletons in these molecules, a variety of new strategies for the con- Received 24th September 2019, struction of cyclobutane rings have greatly emerged during the last decade. In this review, we wish to Accepted 11th November 2019 summarize the recent progress in the cyclobutane-containing natural product synthesis with an emphasis DOI: 10.1039/c9qo01178a on disconnection tactics employed to forge the four-membered rings, aiming to provide a complement rsc.li/frontiers-organic to existing reviews. 1. Introduction stereoselectively, poses significant challenges in synthetic chemistry. On the other hand, cyclobutanes readily undergo a In the class of strained carbocycles, cyclobutanes have been number of ring-opening reactions by virtue of their tendency known as intriguing structural motifs for more than one to release inherent strain energies. In some cases, however, century but remained relatively less explored in parallel with striking ring strains can be dramatically reduced by the instal- their homologues.1 Due to the highly strained ring systems (ca. lation of a gem-dialkyl substituent (through the Thorpe–Ingold − 26.7 kcal mol 1), construction of cyclobutane rings, especially effect),2 a carbonyl group, a heteroatom, or other functional- ities (Fig. -
Dichloroethylene
Development Support Document Final, October 15, 2007 Accessible 2013 1,1-Dichloroethylene CAS Registry Number: 75-35-4 Prepared by Shannon Ethridge, M.S. Toxicology Section Chief Engineer’s Office ___________________________________________________________ TEXAS COMMISSION ON ENVIRONMENTAL QUALITY 1,1 Dichloroethylene Page 2 TABLE OF CONTENTS CHAPTER 1 SUMMARY TABLES ........................................................................................... 4 CHAPTER 2 MAJOR USES OR SOURCES ............................................................................ 6 CHAPTER 3 ACUTE EVALUATION ....................................................................................... 6 3.1 HEALTH-BASED ACUTE REV AND ESL ................................................................................. 6 3.1.1 Physical/Chemical Properties and Key Studies ............................................................. 6 3.1.2 Mode-of-Action (MOA) Analysis ................................................................................. 10 3.1.3 Dose Metric .................................................................................................................. 10 3.1.4 Point of Departure (POD) for the Key Study............................................................... 10 3.1.5 Dosimetric Adjustments ............................................................................................... 11 3.1.6 Critical Effect and Adjustment of PODHEC .................................................................. 11 3.1.7 Health-Based -
Health Effects Support Document for Hexachlorobutadiene Health Effects Support Document for Hexachlorobutadiene
Health Effects Support Document for Hexachlorobutadiene Health Effects Support Document for Hexachlorobutadiene U.S. Environmental Protection Agency Office of Water (4304T) Health and Ecological Criteria Division Washington, DC 20460 www.epa.gov/safewater/ EPA 822-R-03-002 February 2003 Printed on Recycled Paper FOREWORD The Safe Drinking Water Act (SDWA), as amended in 1996, requires the Administrator of the Environmental Protection Agency (EPA) to establish a list of contaminants to aid the agency in regulatory priority setting for the drinking water program. In addition, SDWA requires EPA to make regulatory determinations for no fewer than five contaminants by August 2001. The criteria used to determine whether or not to regulate a chemical on the CCL are the following: The contaminant may have an adverse effect on the health of persons. The contaminant is known to occur or there is a substantial likelihood that the contaminant will occur in public water systems with a frequency and at levels of public health concern. In the sole judgment of the administrator, regulation of such contaminant presents a meaningful opportunity for health risk reduction for persons served by public water systems. The Agency’s findings for the three criteria are used in making a determination to regulate a contaminant. The Agency may determine that there is no need for regulation when a contaminant fails to meet one of the criteria. This document provides the health effects basis for the regulatory determination for hexachlorobutadiene. In arriving at the regulatory determination, data on toxicokinetics, human exposure, acute and chronic toxicity to animals and humans, epidemiology, and mechanisms of toxicity were evaluated. -
Toxicological Profile for 1,1-Dichloroethene Draft for Public Comment December 2019 1,1-DICHLOROETHENE Ii
F Toxicological Profile for 1,1-Dichloroethene Draft for Public Comment December 2019 1,1-DICHLOROETHENE ii DISCLAIMER Use of trade names is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry, the Public Health Service, or the U.S. Department of Health and Human Services. This information is distributed solely for the purpose of pre dissemination public comment under applicable information quality guidelines. It has not been formally disseminated by the Agency for Toxic Substances and Disease Registry. It does not represent and should not be construed to represent any agency determination or policy. ***DRAFT FOR PUBLIC COMMENT*** 1,1-DICHLOROETHENE iii FOREWORD This toxicological profile is prepared in accordance with guidelines developed by the Agency for Toxic Substances and Disease Registry (ATSDR) and the Environmental Protection Agency (EPA). The original guidelines were published in the Federal Register on April 17, 1987. Each profile will be revised and republished as necessary. The ATSDR toxicological profile succinctly characterizes the toxicologic and adverse health effects information for these toxic substances described therein. Each peer-reviewed profile identifies and reviews the key literature that describes a substance's toxicologic properties. Other pertinent literature is also presented, but is described in less detail than the key studies. The profile is not intended to be an exhaustive document; however, more comprehensive sources of specialty information are referenced. The focus of the profiles is on health and toxicologic information; therefore, each toxicological profile begins with a relevance to public health discussion which would allow a public health professional to make a real-time determination of whether the presence of a particular substance in the environment poses a potential threat to human health. -
1,1-Dichloroethene (Vinylidene Chloride)
This report contains the collective views of an international group of experts and does not necessarily represent the decisions or the stated policy of the United Nations Environment Programme, the International Labour Organization, or the World Health Organization. Concise International Chemical Assessment Document 51 1,1-DICHLOROETHENE (VINYLIDENE CHLORIDE) Please note that the pagination and layout of this web version are not identical to the printed CICAD First draft prepared by Dr Bob Benson, US Environmental Protection Agency, Denver, Colorado, USA Published under the joint sponsorship of the United Nations Environment Programme, the International Labour Organization, and the World Health Organization, and produced within the framework of the Inter-Organization Programme for the Sound Management of Chemicals. World Health Organization Geneva, 2003 The International Programme on Chemical Safety (IPCS), established in 1980, is a joint venture of the United Nations Environment Programme (UNEP), the International Labour Organization (ILO), and the World Health Organization (WHO). The overall objectives of the IPCS are to establish the scientific basis for assessment of the risk to human health and the environment from exposure to chemicals, through international peer review processes, as a prerequisite for the promotion of chemical safety, and to provide technical assistance in strengthening national capacities for the sound management of chemicals. The Inter-Organization Programme for the Sound Management of Chemicals (IOMC) was established in 1995 by UNEP, ILO, the Food and Agriculture Organization of the United Nations, WHO, the United Nations Industrial Development Organization, the United Nations Institute for Training and Research, and the Organisation for Economic Co-operation and Development (Participating Organizations), following recommendations made by the 1992 UN Conference on Environment and Development to strengthen cooperation and increase coordination in the field of chemical safety. -
Chlorotrifluoroethylene Interim AEGL Document
ACUTE EXPOSURE GUIDELINE LEVELS (AEGLs) FOR CHLOROTRIFLUOROETHYLENE (CAS Reg. No. 79-38-9) CF2 = CFCl INTERIM ACUTE EXPOSURE GUIDELINE LEVELS (AEGLs) FOR CHLOROTRIFLUOROETHYLENE (CAS Reg. No. 79-38-9) INTERIM CHLOROTRIFLUOROETHYLENE INTERIM: 06/2008/ Page 3 of 34 PREFACE Under the authority of the Federal Advisory Committee Act (FACA) P. L. 92-463 of 1972, the National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances (NAC/AEGL Committee) has been established to identify, review and interpret relevant toxicologic and other scientific data and develop AEGLs for high priority, acutely toxic chemicals. AEGLs represent threshold exposure limits for the general public and are applicable to emergency exposure periods ranging from 10 minutes to 8 hours. Three levels – AEGL-1, AEGL-2 and AEGL-3 C are developed for each of five exposure periods (10 and 30 minutes, 1 hour, 4 hours, and 8 hours) and are distinguished by varying degrees of severity of toxic effects. The three AEGLs are defined as follows: AEGL-1 is the airborne concentration (expressed as parts per million or milligrams per cubic meter [ppm or mg/m3]) of a substance above which it is predicted that the general population, including susceptible individuals, could experience notable discomfort, irritation, or certain asymptomatic, non-sensory effects. However, the effects are not disabling and are transient and reversible upon cessation of exposure. AEGL-2 is the airborne concentration (expressed as ppm or mg/m3) of a substance above which it is predicted that the general population, including susceptible individuals, could experience irreversible or other serious, long-lasting adverse health effects or an impaired ability to escape. -
Jailbreaking Benzene Dimers † Andrey Yu
Communication pubs.acs.org/JACS Jailbreaking Benzene Dimers † Andrey Yu. Rogachev, Xiao-Dong Wen, and Roald Hoffmann* Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, United States *S Supporting Information 5 and 6 were calculated as not much less stable than the known ABSTRACT: We suggest four new benzene dimers, dimers. (C6H6)2, all featuring one or more cyclohexadiene rings trans-fused to 4- or 6-membered rings. These hypothetical dimers are 50−99 kcal/mol less stable than two benzenes, but have computed activation energies to fragmentation ≥27 kcal/mol. A thorough search of potential escape routes was undertaken, through cyclobutane ring cleavage to 12-annulenes, sigmatropic 1,5-H-shifts, electrocyclic ring-openings of the 6-membered rings, and Diels−Alder dimerizations. Some channels for reaction emerge, but there is a reasonable chance that some of these new benzene dimers can be made. Apparently trans-bridging a butadiene 1,2 on a cyclobutane ring, with the latter’s freedom to pucker, is not as difficult as one n the course of thinking about benzene under gigapascal might think.11 Nor is it problematic for a butadiene to bridge the I pressure,1 we decided we might learn something from the gauche positions of an approximately staggered ethane. dimers of benzene, as signposts to the pressure-induced poly- No longer succumbing to the prejudice of avoiding trans- merization of the compound. To induce the benzenes to dimerize, bridging of a cyclobutane ring by a butadiene, from this point we brought two benzene molecules to an uncomfortably close we proceeded down a systematic (human, not machine) path, contact,2 and then let loose the geometry optimization of a 3 generating geometries for all reasonable cycloadducts. -
United States Patent Office Patented Mar
3,239,568 United States Patent Office Patented Mar. 8, 1966 2 the metal atom bonded to the oxygen atom of the alkoxide 3,239,568 molecule. MANUFACTURE OF ALKALMETAL (COAEPOUNDS Thus the alkali metallometallic alkoxides of this inven David O. De Pree and anaes D. Johnston, Baton Rotage, tion are bifunctional compounds-that is they contain two La., assignors to Ethyl Corporation, New York, N.Y., 5 reactive centers. One of the striking features of this in a corporation of Virginia vention is that in a reaction with a hydrocarbon halide or No Drawing. Filled Aug. 9, 1960, Ser. No. 48,356 hydrocarbon sulfate alkylating agent only the “metal 6 Claims. (C. 260-632) lo,' i.e. This invention involves a process for the manufacture O of organic compounds, in particular, alkali metal alkox --M ides, which can easily be converted to the corresponding functional group reacts, and the "metallic,” i.e. alcohols. This invention is also concerned with bimetal lic organometallic compounds which are utilized in pre paring the alkali metal alkoxides of this invention. --OM Prior to this invention no satisfactory method was reactive center does not. known for increasing the molecular weight of metal alk Although the terms alkali metallometallic alkoxide and oxides using direct reactions of organic halides or organic metal alkoxide are employed throughout this specifica Sulfates. A process which employs hydrocarbon halides tion the process of this invention can be carried out using or hydrocarbon sulfates, and in particular, long chain hy 20 the corresponding alkenoxides and aryioxides, as these drocarbon halides, to produce alkali metal alkoxides of compounds are essentially equivalent to alkoxides for the increased chain length would be of particular value to purposes of this invention. -
Hydrocarbon Compounds 22
05_Chem_GRSW_Ch22.SE/TE 6/11/04 3:52 PM Page 237 Name ___________________________ Date ___________________ Class __________________ HYDROCARBON COMPOUNDS 22 SECTION 22.1 HYDROCARBONS (pages 693–701) This section describes the bonding in hydrocarbons and distinguishes straight-chain from branched-chain alkanes. It also provides rules for naming branch-chained alkanes. Organic Chemistry and Hydrocarbons (pages 693–694) 1. What is organic chemistry? It__________________________________________________ is the study of the chemistry of carbon compounds. 2. Organic compounds that contain only carbon and hydrogen are called ______________________hydrocarbons . 3. Is the following sentence true or false? Hydrogen atoms are the only atoms that can bond to the carbon atoms in a hydrocarbon. ______________________false 4. Circle the letter of each statement that is true about carbon’s ability to form bonds. a. Carbon atoms have four valence electrons. b. Carbon atoms always form three covalent bonds. c. Carbon atoms can form stable bonds with other carbon atoms. Alkanes (pages 694–699) 5. Is the following sentence true or false? Alkanes contain only single covalent bonds. ______________________true 6. What is the simplest alkane? ______________________methane 7. What are straight-chain alkanes?They ______________________________________________ contain any number of carbon atoms, one after another, in a chain. 8. The names of all alkanes end with the suffix ______________________-ane . Match the name of the straight-chain alkane with the number of carbon atoms it contains. _______d 9. nonane a. 3 _______a 10. propane b. 4 c _______ 11. heptane c. 7 © Pearson Education, Inc., publishing as Prentice Hall. All rights reserved. _______b 12. butane d. 9 13. The straight-chain alkanes form a(n) ______________________________homologous series because there is an incremental change of a CH2 group from one compound in the series to the next.