Acetone Cyanohydrin
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From Acrolein Cyanohydrin
Agric. Biol. Chem., 52 (2), 589-591, 1988 589 Note carried out at iuu~zuirc under an increased pressure/' Here, we present a novel single-step synthesis of 5-(/?- methylthioethyl)hydantoin (2), in which we employed Single-step Synthesis of 5-(j6- single-step reactions of acrolein cyanohydrin (AC, 4), Methylthioethyl)hydantoin methyl mercaptan and ammoniumcarbonate in polar solvents (the AC method), and of acrolein (AL, 1), from Acrolein Cyanohydrin hydrogen cyanide, methyl mercaptan and ammonium and Acrolein carbonate (the ALmethod), accompanied with the for- mation of a-ureido-y-methylthiobutyramide (UMA, 5). Chisei Shibuya and Shunji Ouchi* By an alkaline hydrolysis of these products, dl- methionine (MT, 3) was obtained in an 85%yield on the Food Products & Pharmaceuticals Plant, bases of acrolein cyanohydrin and of acrolein. Asahi Chemical Industry Co., Ltd., Whenthe single-step hydantoination was carried out 6-2700 Asahimachi, Nobeoka, from ACor AL, a mixture of 2 and 5 was obtained. Miyazaki 882, Japan Approximately 12mol% of 5 was formed in each case of *Analytical Research Center, using AL and AC. Asahi Chemical Industry Co., Ltd., These new reactions are summarized in the following 1-3-1 Yako, Kawasaki-ku, Kawasaki-shi, equations: Kanagawa 210, Japan According to this procedure, acrolein and acrolein Received July 27, 1987 cyanohydrin, which are unstable to alkali, were not polymerized by the presence of excess ammoniumcar- bonate,-and the desired reaction proceeded in high yields. Single-step hydantoination of ACusing methanol as the A number of methods for DL-methionine synthesis solvent was carried out, and the effect of quantities of through the hydantoin intermediate have been reported methyl mercaptan, hydrogen cyanide and ammonium since Pierson1* obtained methionine in a 50%yield starting carbonate on the yield of MTwas investigated. -
Transport of Dangerous Goods
ST/SG/AC.10/1/Rev.16 (Vol.I) Recommendations on the TRANSPORT OF DANGEROUS GOODS Model Regulations Volume I Sixteenth revised edition UNITED NATIONS New York and Geneva, 2009 NOTE The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the United Nations concerning the legal status of any country, territory, city or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries. ST/SG/AC.10/1/Rev.16 (Vol.I) Copyright © United Nations, 2009 All rights reserved. No part of this publication may, for sales purposes, be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, electrostatic, magnetic tape, mechanical, photocopying or otherwise, without prior permission in writing from the United Nations. UNITED NATIONS Sales No. E.09.VIII.2 ISBN 978-92-1-139136-7 (complete set of two volumes) ISSN 1014-5753 Volumes I and II not to be sold separately FOREWORD The Recommendations on the Transport of Dangerous Goods are addressed to governments and to the international organizations concerned with safety in the transport of dangerous goods. The first version, prepared by the United Nations Economic and Social Council's Committee of Experts on the Transport of Dangerous Goods, was published in 1956 (ST/ECA/43-E/CN.2/170). In response to developments in technology and the changing needs of users, they have been regularly amended and updated at succeeding sessions of the Committee of Experts pursuant to Resolution 645 G (XXIII) of 26 April 1957 of the Economic and Social Council and subsequent resolutions. -
Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers
molecules Article Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers Samuel Delgado-Hernández 1,2 , Fernando García-Tellado 1,* and David Tejedor 1,* 1 Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Astrofísico Francisco Sánchez 3, 38206 La Laguna, Spain; [email protected] 2 Doctoral and Postgraduate School, Universidad de La Laguna, Apartado Postal 456, 38200 La Laguna, Spain * Correspondence: [email protected] (F.G.-T.); [email protected] (D.T.) Abstract: A novel organocatalytic multicomponent cyanovinylation of aldehydes was designed for the synthesis of conjugated cyanomethyl vinyl ethers. The reaction was implemented for the synthesis of a 3-substituted 3-(cyanomethoxy)acrylates, using aldehydes as substrates, acetone cyanohydrin as the cyanide anion source, and methyl propiolate as the source of the vinyl com- ponent. The multicomponent reaction is catalyzed by N-methyl morpholine (2.5 mol%) to deliver the 3-(cyanomethoxy)acrylates in excellent yields and with preponderance of the E-isomer. The multicomponent reaction manifold is highly tolerant to the structure and composition of the aldehyde (aliphatic, aromatic, heteroaromatics), and it is instrumentally simple (one batch, open atmospheres), economic (2.5 mol% catalyst, stoichiometric reagents), environmentally friendly (no toxic waste), and Citation: Delgado-Hernández, S.; sustainable (easy scalability). García-Tellado, F.; Tejedor, D. Cyanovinylation of -
Cyanide Poisoning and How to Treat It Using CYANOKIT (Hydroxocobalamin for Injection) 5G
Cyanide Poisoning and How to Treat It Using CYANOKIT (hydroxocobalamin for injection) 5g 1. CYANOKIT (single 5-g vial) [package insert]. Columbia, MD: Meridian Medical Technologies, Inc.; 2011. Please see Important Safety Information on slides 3-4 and full Prescribing Information for CYANOKIT starting on slide 33. CYANOKIT is a registered trademark of SERB Sarl, licensed by Meridian Medical Technologies, Inc., a Pfizer company. Copyright © 2015 Meridian Medical Technologies, Inc., a Pfizer company. All rights reserved. CYK783109-01 November/2015. Indication and Important Safety Information……………………………………………………………………………….………..…..3 . Identifying Cyanide Poisoning……………………………………………………………………………………………………………….…………….….5 . How CYANOKIT (hydroxocobalamin for injection) Works……………………………………………………………….12 . The Specifics of CYANOKIT…………………………………………………………………………………………………………………………….………17 . Administering CYANOKIT………………………………………………………………………………………………………………………………..……….21 . Storage and Disposal of CYANOKIT…................................................................................................................................26 . Grant Information for CYANOKIT……………………………………………………………………………………………………………………....30 . Full Prescribing Information………………………………………………………………………………………………….………………………………33 Please see Important Safety Information on slides 3-4 and full Prescribing Information for CYANOKIT starting on slide 33. CYANOKIT (hydroxocobalamin for injection) 5 g for intravenous infusion is indicated for the treatment of known or suspected cyanide poisoning. -
Hazardous Chemicals in Secondhand Marijuana Smoke
Hazardous Chemicals in Secondhand Marijuana Smoke “The following 33 marijuana smoke constituents included in Table 1 are listed under 33 Chemicals Proposition 65 as causing cancer: acetaldehyde, acetamide, acrylonitrile, 4- aminobiphenyl, arsenic, benz[a]anthracene, benzene, benzo[a]pyrene, That Can benzo[b]fluoranthene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzofuran, 1,3- butadiene, cadmium, carbazole, catechol, chromium (hexavalent compounds), Cancer chrysene, dibenz[a,h]anthracene, dibenz[a,i]pyrene, dibenzo[a,e]pyrene, “Many of the chemical diethylnitrosamine, dimethylnitrosamine, formaldehyde, indeno[1,2,3,-c,d]pyrene, constituents that have been isoprene, lead, mercury, 5-methylchrysene, naphthalene, nickel, pyridine, and identified in marijuana smoke quinoline.” are carcinogens.” 2009 OEHHA document, Evidence on the Carcinogenicity of Marijuana Smoke Hydrogen Cyanide interferes with the normal use of oxygen by nearly every organ of Hydrogen the body. Exposure to hydrogen cyanide (AC) can be rapidly fatal. It has whole-body (systemic) effects, particularly affecting those organ systems most sensitive to low Cyanide oxygen levels: the central nervous system (brain), the cardiovascular system (heart Is the same chemical used for and blood vessels), and the pulmonary system (lungs). Hydrogen cyanide (AC) is a chemical weapons. chemical warfare agent (military designation, AC). Ammonia gas is a severe respiratory tract irritant. Can cause severe irritation of the Ammonia nose and throat. Can cause life-threatening accumulation of fluid in the lungs Household cleaner used on (pulmonary edema). Symptoms may include coughing, shortness of breath, difficult floors and toilets. There is 3 breathing and tightness in the chest. Symptoms may develop hours after exposure times more in secondhand and are made worse by physical effort. -
Assessment of Portable HAZMAT Sensors for First Responders
The author(s) shown below used Federal funds provided by the U.S. Department of Justice and prepared the following final report: Document Title: Assessment of Portable HAZMAT Sensors for First Responders Author(s): Chad Huffman, Ph.D., Lars Ericson, Ph.D. Document No.: 246708 Date Received: May 2014 Award Number: 2010-IJ-CX-K024 This report has not been published by the U.S. Department of Justice. To provide better customer service, NCJRS has made this Federally- funded grant report available electronically. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. Department of Justice. Assessment of Portable HAZMAT Sensors for First Responders DOJ Office of Justice Programs National Institute of Justice Sensor, Surveillance, and Biometric Technologies (SSBT) Center of Excellence (CoE) March 1, 2012 Submitted by ManTech Advanced Systems International 1000 Technology Drive, Suite 3310 Fairmont, West Virginia 26554 Telephone: (304) 368-4120 Fax: (304) 366-8096 Dr. Chad Huffman, Senior Scientist Dr. Lars Ericson, Director UNCLASSIFIED This project was supported by Award No. 2010-IJ-CX-K024, awarded by the National Institute of Justice, Office of Justice Programs, U.S. Department of Justice. The opinions, findings, and conclusions or recommendations expressed in this publication are those of the author(s) and do not necessarily reflect those of the Department of Justice. This document is a research report submitted to the U.S. Department of Justice. This report has not been published by the Department. Opinions or points of view expressed are those of the author(s) and do not necessarily reflect the official position or policies of the U.S. -
The Detoxification of Gold-Mill Tailings with Hydrogen Peroxide by A
J. S. At,. Inst. Min. Metal/., vol. 87, no. 9. Sap. 1987. pp. 279-283. The detoxification of gold-mill tailings with hydrogen peroxide by A. GRIFFITHS., H. KNORRE**, S. GOS:I:,and R. HIGGINS§ SYNOPSIS Hydrogen peroxide is gaining acceptance as a reagent for the treatment of.mining effluents c?ntaininQ cyanide. In this paper some of the chemical and environmental aspects of treatment with hydrogen peroxide are discussed, and one way of improving the economics of the process is described. This is known as selective detoxification, which involves the oxidation of the less stable (cyanide) complexes while not affecting the more stable complexes, which contribute very little to the concentration of free cyanide or to the toxicity of the treated water. SAMEVATTING Waterstofperoksied word al hoe meer aanvaar as 'n reagens vir die behandeling van mynuitvl?eisels w~t si~ni~d bevat. Sommige van die chemiese en omgewingsaspekte van behandeling met waterstofperoks,led word In hlerdle referaat bespreek en een manier om die ekonomie van die proses te verbeter word beskryf. Dlt s~aan bekend. as selektiewe ontgifting en behels die oksidasie van die minder stabiele (sianied) komplekse sonder om die meer stablele komplekse wat baie min tot die konsentrasie van vry sianied, of tot die giftigheid van die behandelde water bydra, te be"invloed. Introduction The detoxification plant supplied by Degussa for use Oxidation of CN- at the gold mine of Ok Tedi Mining Ltd in Papua New CN~ + HP2 CNO- + H2O Guinea represents the first large-scale application of - Hydrolysis of CNO- hydrogen peroxide for the detoxification of tailings from CNO- + 2 H+ a cyanidation plant. -
Hydroxyacetonitrile (HOCH2CN) As a Precursor for Formylcyanide (CHOCN), Ketenimine (CH2CNH), and Cyanogen (NCCN) in Astrophysical Conditions
A&A 549, A93 (2013) Astronomy DOI: 10.1051/0004-6361/201219779 & c ESO 2013 Astrophysics Hydroxyacetonitrile (HOCH2CN) as a precursor for formylcyanide (CHOCN), ketenimine (CH2CNH), and cyanogen (NCCN) in astrophysical conditions G. Danger1, F. Duvernay1, P. Theulé1, F. Borget1, J.-C. Guillemin2, and T. Chiavassa1 1 Aix-Marseille Univ, CNRS, PIIM UMR 7345, 13397 Marseille, France e-mail: [email protected] 2 Institut des Sciences Chimiques de Rennes, École Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35708 Rennes Cedex 7, France Received 8 June 2012 / Accepted 19 November 2012 ABSTRACT Context. The reactivity in astrophysical environments can be investigated in the laboratory through experimental simulations, which provide understanding of the formation of specific molecules detected in the solid phase or in the gas phase of these environments. In this context, the most complex molecules are generally suggested to form at the surface of interstellar grains and to be released into the gas phase through thermal or non-thermal desorption, where they can be detected through rotational spectroscopy. Here, we focus our experiments on the photochemistry of hydroxyacetonitrile (HOCH2CN), whose formation has been shown to compete with aminomethanol (NH2CH2OH), a glycine precursor, through the Strecker synthesis. Aims. We present the first experimental investigation of the ultraviolet (UV) photochemistry of hydroxyacetonitrile (HOCH2CN) as a pure solid or diluted in water ice. Methods. We used Fourier transform infrared (FT-IR) spectroscopy to characterize photoproducts of hydroxyacetonitrile (HOCH2CN) and to determine the different photodegradation pathways of this compound. To improve the photoproduct identifications, irradiations of hydroxyacetonitrile 14N and 15N isotopologues were performed, coupled with theoretical calculations. -
Cyanide Remediation: Current and Past Technologies C.A
CYANIDE REMEDIATION: CURRENT AND PAST TECHNOLOGIES C.A. Young§ and T.S. Jordan, Department of Metallurgical Engineering, Montana Tech, Butte, MT 59701 ABSTRACT Cyanide (CN-) is a toxic species that is found predominantly in industrial effluents generated by metallurgical operations. Cyanide's strong affinity for metals makes it favorable as an agent for metal finishing and treatment and as a lixivant for metal leaching, particularly gold. These technologies are environmentally sound but require safeguards to prevent accidental spills from contaminating soils as well as surface and ground waters. Various methods of cyanide remediation by separation and oxidation are therefore reviewed. Reaction mechanisms are given throughout. The methods are compared in regard to their effectiveness in treating various cyanide species: free cyanide, thiocyanate, weak-acid dissociables and strong-acid dissociables. KEY WORDS cyanide, metal-cyanide complex, thiocyanate, oxidation, separation INTRODUCTION ent on the transport of these heavy metals through their tissues, cyanide is very toxic. Waste waters from industrial operations The mean lethal dose to the human adult is transport many chemicals that have ad- between 50 and 200 mg [2]. U.S. EPA verse effects on the environment. Various standards for drinking and aquatic-biota chemicals leach heavy metals which would waters regarding total cyanide are 200 and otherwise remain immobile. The chemicals 50 ppb, respectively, where total cyanide and heavy metals may be toxic and thus refers to free and metal-complexed cya- cause aquatic and land biota to sicken or nides [3]. According to RCRA, all cyanide species are considered to be acute haz- die. Most waste-water processing tech- ardous materials and have therefore been nologies that are currently available or are designated as P-Class hazardous wastes being developed emphasize the removal of when being disposed of. -
Substituent and Solvent Effects on HCN Elimination from L-Aryl-L,2,2-Tricyanoethanes [1]
Substituent and Solvent Effects on HCN Elimination from l-Aryl-l,2,2-tricyanoethanes [1] Fouad M. Fouad Max-Planck-Institut für Biochemie, D-8033 Martinsried bei München, West Germany and Patrick G. Farrell Department of Chemistry, McGill University, Montreal, Quebec, Canada, H3A 2K6 Z. Naturforsch. 34b, 86-94 (1979); received August 2, 1978 1,2,2-Tricyanoethanes, Elimination of HCN The elimination of HCN from 9-dicyanomethyl-fluorene (2), 1,1-diphenyl-1,2,2- tricyanoethane (3), and 2-phenyl-I,l,2-tricyano-propane (4) in anhydrous methanol has been studied and shown to occur via an (E l)anion mechanism. Elimination of HCN from 2 in acidic, buffered and MeO~/MeOH solutions have also been studied. Addition of water or benzene to the reaction medium shifts the mechanism to (E 1 CB)R. Elimination of HCN from N,N-dimethyl-4-(I,I,2-tricyanoethyl) aniline (5) in anhydrous methanol occurs via an (E 1 CB)r mechanism and the kinetics indicate that addition of HCN to the product alkene occurs. Activation parameters, isotope effects and solvent effects have been examined in an effort to obtain information about the nature of the transition states of these reactions. Introduction tion via the ElcB mechanism [2-5]. Within the The base catalyzed elimination of HCN from overall ElcB mechanistic scheme a number of various polycyanoethane derivatives has been the possible rate-determining steps may be envisaged, subject of several mechanistic investigations because giving rise to different kinetic schemes, and exam- of the potential stabilization of an intermediate ples of elimination via each of these pathways have carbanion in such systems, thus favouring elimina- been reported [6]. -
The List of Extremely Hazardous Substances)
APPENDIX A (THE LIST OF EXTREMELY HAZARDOUS SUBSTANCES) THRESHOLD REPORTABLE INVENTORY RELEASE QUANTITY QUANTITY CAS NUMBER CHEMICAL NAME (POUNDS) (POUNDS) 75-86-5 ACETONE CYANOHYDRIN 500 10 1752-30-3 ACETONE THIOSEMICARBAZIDE 500/500 1,000 107-02-8 ACROLEIN 500 1 79-06-1 ACRYLAMIDE 500/500 5,000 107-13-1 ACRYLONITRILE 500 100 814-68-6 ACRYLYL CHLORIDE 100 100 111-69-3 ADIPONITRILE 500 1,000 116-06-3 ALDICARB 100/500 1 309-00-2 ALDRIN 500/500 1 107-18-6 ALLYL ALCOHOL 500 100 107-11-9 ALLYLAMINE 500 500 20859-73-8 ALUMINUM PHOSPHIDE 500 100 54-62-6 AMINOPTERIN 500/500 500 78-53-5 AMITON 500 500 3734-97-2 AMITON OXALATE 100/500 100 7664-41-7 AMMONIA 500 100 300-62-9 AMPHETAMINE 500 1,000 62-53-3 ANILINE 500 5,000 88-05-1 ANILINE,2,4,6-TRIMETHYL- 500 500 7783-70-2 ANTIMONY PENTAFLUORIDE 500 500 1397-94-0 ANTIMYCIN A 500/500 1,000 86-88-4 ANTU 500/500 100 1303-28-2 ARSENIC PENTOXIDE 100/500 1 THRESHOLD REPORTABLE INVENTORY RELEASE QUANTITY QUANTITY CAS NUMBER CHEMICAL NAME (POUNDS) (POUNDS) 1327-53-3 ARSENOUS OXIDE 100/500 1 7784-34-1 ARSENOUS TRICHLORIDE 500 1 7784-42-1 ARSINE 100 100 2642-71-9 AZINPHOS-ETHYL 100/500 100 86-50-0 AZINPHOS-METHYL 10/500 1 98-87-3 BENZAL CHLORIDE 500 5,000 98-16-8 BENZENAMINE, 3-(TRIFLUOROMETHYL)- 500 500 100-14-1 BENZENE, 1-(CHLOROMETHYL)-4-NITRO- 500/500 500 98-05-5 BENZENEARSONIC ACID 10/500 10 3615-21-2 BENZIMIDAZOLE, 4,5-DICHLORO-2-(TRI- 500/500 500 FLUOROMETHYL)- 98-07-7 BENZOTRICHLORIDE 100 10 100-44-7 BENZYL CHLORIDE 500 100 140-29-4 BENZYL CYANIDE 500 500 15271-41-7 BICYCLO[2.2.1]HEPTANE-2-CARBONITRILE,5- -
Investigation of Cyano·Methylation Reaction by Cyano·Hydrine and Its Determination in Tobacco-Smoke. ( Strecker·Reactions )
PERIODICA POLYTECHNICA SER. CHEM. ENG. VOL. 36, NO. 3, PP. 209-2113 {I992} INVESTIGATION OF CYANO·METHYLATION REACTION BY CYANO·HYDRINE AND ITS DETERMINATION IN TOBACCO-SMOKE. ( STRECKER·REACTIONS ) 3 Vikt6ria HORVATH,l Lajos TREZLl, Tibor SZARVAS2, Janos PIPEK , Csaba VIDA 1 and Krisztina BAUER4 1 Department of Organic Chemical Technology, 3Department of Physics Technical University of Budapest, 2 Institute of Isotopes of the Hungarian Academy of Sciences 4 Plant Protection Institute,Hungarian Academy of Sciences. Received: September 9, 1992 Abstract The results of our research work [1-7) of several years aimed at the binding of the unhealthy components of tobacco smoke directed our attention to the analysis and identification of the unknown peak observed during the high sensitivity radiochromatographic analysis of tobacco smoke condensates.It was a fruitless effort to remove the formaldehyde, the ac etaldehyde and hydrogen cyanide present in tobacco smoke, or even to try to eliminate them separately, during the analysis the new, unknown peak appeared again and again on the radiochromatogram. During our research work we stated, that we were facing the Strecker reaction [8-9), known since 1850, that is,with the formation of cyanohydrine of the aldehydes and hydrogen cyanide present in tobacco smoke, corresponding to the new peak. Cyanohydrines to react quickly and energetically with basic aminoacids, during which reaction cyanomethyl derivatives are being formed. This reaction is proceeding also under physiological circumstances with the basic amino groups of proteins, contributing to the development of respiratory and cardiovascular insufficiencies. By means of model reactions and using solutions of tobacco smoke gases the process of the reaction was proved in a primary way, also its circumstances having been cleared.