DOCSLIB.ORG

The Synthesis of a Water-Soluble Molecule

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
The Synthesis of a Water-Soluble Molecule THE SYNTHESIS OF A WATER-SOLUBLE MOLECULE CONTAINING A HYDROPHOBIC CAVITY by W. HARRY MANDEVILLE B. S. Colorado School of Mines (1971) SUBMITTED IN PARTIAL FULFILLMENT OF'THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY at the MASSACHUSETTS INSTITUTE OF TECHNOLOGY May 16, 1975 Signature of Author / Department of Chemistry May , 1975 Certified by K Thesis Supervisor Accepted by --~~~~~~~~~ ( Chairman, Departmental ARCHIVES Committee JUN 11 1975 -2- This Doctoral. Thesis has been examined by a committee of the Department of Chemistry as follows: Professor Dietmar Seyferth I/ Chairman Professor George MI.Whitesides \K. u- '|Thesis Supervisor Professor K. Barry Sharpless -3- to SUSIE... 143 for CHRISTMAS and SNOW and to MY PARENTS -4- "You know how when you stand in the rain with your mouth open how rarely the raindrops hit your tongue... Chemistry is a lot like that. I like standing in the rain." April 30, 1975 -5- THE SYNTHESIS of a WATER-SOLUBLE MOLECULE CONTAINING a HYDROPHOBIC CAVITY by W. Harry Mandeville Submitted to the Department of Chemistry at the Massachusetts Institute of Technology, May 16, 1975, in partial fulfillment of the requirements for the degree of Doctor of Philosophy. ABSTRACT Part I: The Synthesis of a Water-Soluble Molecule Containing a Hydrophobic Cavity The syntheses and characterization of three macrocyclic compounds, cyclohexatriaconta[l,2,13,14,25,26-b,b',b"]tris- quinoxaline (1) cyclohexatriaconta[l,2,13,14,25,26-b,b',b"] tris(diethyl 1H,3H,2-oxoimadazo[4,5-g]quinoxalino-l,3-di- a-acetate) (2) and cyclopentatetraconta[1,2,16,17,31,32-b, b',b"]trisqu'lnoxaline (3 are described. These compounds have been prepared from the benzene derivatives tris(deca- methylene)benzene (7a) and tris(tridecamethylene)benzene (7c) via a ring-opening ozonolysis. Compounds 7a and 7c were prepared from the corresponding cyclic acetylenes, cyclo- dodecyne (4) and cyclopentadecyne ED via a titanium trichloride catalyzed cyclotrimerization. A new, convenient synthesis for the cyclic alkynes 4 and 6, utilizing the corresponding cyclic ketones as starting materials, is also described. One other compound, tris(hendecamethylene)benzene (7b) was also prepared but its ozonolysis did not yield the expected macrocyclic derivative. a 0· _. 0 041 -6- 7a, n 10 4, n=10' 7b, n= 11 (CHFc)n III 5, n=11 2 7o, n13 K, 6. n=13 a i I Part II: The Elucidation of the Mecnanism of Oxidation with Adams' Catalyst. Several mechanisms for the oxidation of alcohols by Adams' catalyst and molecular oxygen are postulated. Each of these mechanisms is discussed with respect to evidence already in the literature and with respect to new evidence found in the present work. The deuterium isotope effect for the oxidation of 2-propanol-dl has been determined to be 1.8. The competitive oxidation of cis- and trans-4-t- butylcyclohexanol has shown the oxidation follows the same stereochemical path as the von Auwers-Skita rule dictates for the reduction of cyclohexanones with hydrogen. The oxidation of cyclobutanol and cyclopentanol show the reaction does not proceed via a homolytic cleavage of a hydrogen-oxygen bond to form a metal-oxygen bond. Part III: Selectivity in Organic Group Transfer in Reactions of Mixed Lithium Diorganocuprates. This work has been published: W. Harry Mandeville and George M. Whitesides, J. Org. Chem., 39, 400 (1974). Thesis Supervisor: George M. Whitesides Title: Professor of Chemistry -7- ACKNOWLEDGEMENTS I would like to gratefully acknowledge the M.I.T. Department of Chemistry for support in the form of a teaching assistantship for the academic year 1971-2 and Professor George M. Whitesides and the National Science Foundation for support in the form of Research Assistantships for the remainder of my stay at M.I.T. I would like to thank Jim Simms for running a "taut ship" in the spec lab and for keeping most of the instruments running most of the time and Dan Traficante for help in taking my carbon-13 nmr spectra. Finally, I would like to thank all of the other Dreyfus inmates who have made my life either miserable or livable during the last four years: Demers and the Beaver, the two other inhabitants of my bay; at times the stench was terrific but we all survived; Hill, the Scarlet Speedster; Lilburn, who says sulfur chemistry has to smell bad, anyway; Cox, for late night beers, poker, softball and for falling for the old raw Easter egg trick; the Turk and Wilson for more nocturnal beer drinking; Michaelson, Q. Kyle, Mad-Dog Dolhun and the other poker players who let me take their money; Bock, Mac, Nate and X, who lived with me in the ghetto at 181 Harvard St.; why was I never mugged; Kaufman, Trzupek, and Bird-Brain, my predecessors in chemical trivia; the Gutman, for financial -8- advice; Costa, for general rowdiness; Kazdin, for 7,000 bad ideas-and one good one; John Ning, for leaving; van Volkom, where did he go; Feitler, Rogers, Foley and the rest of the morons here who kept me from ever getting bored. A last note of thanks is due to Susie; she brought me back to earth on the weekends, and to George; his interest in chemistry was contagious. Thanks also to Katie Hallinan for doing a superb job of typing this thesis. -9- TABLE of CONTENTS Page Part I: The Synthesis of a Water-Soluble Molecule 18 Containing a Hydrophobic Cavity. Cyclododecyne, Cyclotridecyne and Cyclo- 21 pentadecyne. Cyclotrimerization of the Cyclic Acetylenes. 27 Ozonolysis of the Cyclic Trimers of Cyclo- 29 dodecyne, Cyclotridecyne and Cyclopentadecyne Derivatization of the Cyclic a-Diketones. 30 Optimization of the Ozonolysis Conditions. 38 Ozonolysis in Aprotic Solvents. 41 Ozonolysis in heptane. 42 Ozonolysis in methylene chloride. 43 Ozonolysis in a Protic Solvent. 43 Ozonolysis in methanol/methylene chloride. 46 Reduction of Ozonolysis Mixtures. 46 Attempted Oxidation of 7a with Ruthenium 50 Tetroxide. Preparation of a Water-Soluble Derivative. 50 Conclusions. 59 Experimental Section. 60 General. 60 1,l-Dichlorocyclododecane 61 Cyclododecyne (4). 62 Cyclopentadecyne (6). 63 13 ,13-Dibromobicyclo[10.1.0]tridecane. 63 -10- Cyclotrideca-1,2-diene. 64 Cyclotridecyne (5). 64 Tris(decamethylene)benzene (7a). 65 (Cyclododecyne Cyclotrimer.) 4 Tris(hendecamethylene)benzene (7b). 66 (Cyclotridecyne Cyclotrimer.) Tris(tridecamethylene)benzene (7c). 66 (Cyclopentadecyne Cyclotrimer.)- 2-Oximinocyclododecanone. 67 Cyclododecane-1,2-dione. 67 2,3-Decamethylenequinoxaline (la). 67 2,3-Decamethylenequinoxaline dihydro- 67 chloride. Solubility in Water. Attempted Preparation of 1,4-Dimethyl-2,3- 67 decamethylenequinoxaline. Methyl Iodide. Attempted Preparation of 1,4-Dimethyl-2,3- 68 decamethylenequinoxaline. Dimethyl Sulfate. 1,4-Diethyl-2,3-decamethylenequinoxaline. 68 Attempted Preparation of 2,3-Decamethylene- 69 quinoxalinedi-N,N'-oxide. 6-Methyl-2,3-decamethylenequinoxaline. 69 6,7-Dimethyl-2,3-decamethylenequinoxaline. 69 2,3-Decamethylenepyrazine-5,6-dicarboxylic 69 Acid. Potassium Permanganate Oxidation of 2,3-Decamethylenequinoxaline. 2,3-Decamethylene-5,6-dicyanopyrazine. 70 2,3-Decamethylenepyrazine-5,6-dicarboxylic 70 Acid. Hydrolysis of 2,3-Decamethylene-5,6- Dicyanopyrazine. -11- 2,3-Decamethylenepyrazine-5,6-dicarboxylate 71 Dipotassium Salt. Attempted Oxidation of Hexatriaconta[1,2,13 71 14,25,26-b,b',b"]trisquinoxaline (1) with Potassium Permanganate. Attempted Oxidation of 1 with Potassium 71 Permanganate. Phase Transfer. 3,4-Decamethylene-1,2,5-thiadiazole- 72 1,1-dioxide. 3,4-Decamethylene-2,5-diphenylcyclo- 72 pentadienone. Cyclod.odecane-1,2-dioneMonosemicarba- 73 zone. Benzimidazolone (23). 73 5,6-Dinitrobenzimidazolone (24). 73 Diethyl 5,6-dinitrobenzimidazolone-1,3-di- 74 a-acetate (25). Dimethyl 5,6-dinitrobenzimidazolone- 74 1,3-di-a-acetate. 5,6-Dinitrobenzimidazolone-1,3-di-a- 74 acetic Acid. Diethyl 5,6-diaminobenzimidazolone-1,3-di- 75 a-acet:ate (26). Diethyl 1H,3H,2-oxoimidazo[l4,5-g]cyclo- 75 dodeca [b]uinoxaline-1,3-di-a-acetate (27). 1H,3H,2-Oxoimidazo[4,5-g]cyclododeca[b] 76 quinoxaline-1,3-di-a-acetic Acid (28b). Preparative Scale Ozonolysis of 7a. 76 Preferred Method. ' 2,3-DE!camethylenequinoxaline (lb) and Cyclo- 77 hexatriaconta[l,2,13,14,25,26-b,b',b"]tris- quinoxaline Ul. Condensation of the Ozonolysis Product with 14. -12- Ozonolysis of 7a. (General Techniques.) 79 Diethyl lH,3H, 2-oxoimidazo[4,5-2]cyclo 79 dodeca [b] quinoxaline-1,3-di--a-acetate (27). and Cyclohexatriaconta[1,2,13,14,25,2T- b,b',b"]tris(diethyl H,3H,2-oxoimidazo T475-g] quinoxaline-1 ,3di-c-acetate (2). Condensation of the Ozonolysis Product with 25. 2,3-Tridecamethylenequinoxaline and Cyclo- 81 pentatetraconta[1,2,16,17,31,32-b,b' ,b"] trisquinoxaline (3). Ozonolysis of 7c and Condensationwithm4. Ozonolysis of 7b. 82 Part II. The Elucidation of the Mechanism of Oxidation 84 with Adams' Catalyst. Conclusions. 112 Experimental Section. 113 General. 113 Preparation of the Catalyst. (Typical 113 Procedure A.) Preparation of the Catalyst. (Typical 113 Procedure B.) Competitive Oxidation of Cyclobutanol 114 and Cyclopentanol. (Typical Procedure.) 2-Propanol-2-dl. 114 Competitive Oxidation of Propanol-2 and 115 2-Propanol-2-dl with Adams' Catalyst. trans-4-t-Butylcyclohexanol. 115 Separation of cis- from trans-4-t-Butyl- 115 cyclohexanol. Competitive Oxidation of cis- and trans-4- 116 t-Butylcyclohexanol in Acid Medium with Adams' Catalyst. (Typical Procedure.) -13- Part III. Selectivity in Organic Group Transfer in 117 Reactions of Mixed Lithium Diorganocuprates. Appendix. The Attempted Synthesis of Biotin. 118 Conclusions. 123 Experimental Section. 125 General. 125 4,5-Dimethylimidazolone (31). 125 1,3-Diacetyl-4,5-imidazolone (32) . 125 1,3-D.iacetyl-4,5-bis (exomethylene) 125 imidazolone (33). Dimethlyl 4H,7H-dihydro-1, 3-diacetyl- 126 benzimidazolone-5,6-dicarboxylate. Dimethyl 1,3-diacetylbenzimidazolone- 126 5,6-d:icarboxylate. 1,3-Diacetyl 4H,6H-thiopheno[d]imi- 127 dazolone-5,5-dioxide (30).
Load more

Recommended publications
  • 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.
    [Show full text]
  • 1 Transformer Oil 2 Residual Fuel Oil 3 Diesel Oil Heavy 4
    1 TRANSFORMER OIL 2 RESIDUAL FUEL OIL 3 DIESEL OIL HEAVY 4 SPINDLE OIL MIXTURES CONTAINING 5 CRUDE OIL 6 MOTOR OIL 7 ROAD OIL 8 FUEL OIL NO.4 9 FUEL OIL NO.5 10 FUEL OIL NO.6 LUBRICATING OILS AND 11 BLENDING STOCKS 12 PENETRATING OIL 13 TURBINE OIL 3 14 ROOFERS FLUX 15 CRUDE OIL 16 STRAIGHT RUN RESIDUE OCTAMETHYLCYCLOTETRA 17 SILOXANE BENZENEPROPANOIC ACID, 3,5- 1,1- 3,5-BIS(1,1-DIMETHYLETHYL 18 4- ), -C7-C9 4-HYDROXY-C7-C9ALCOHOL S BRANCHED AND LINEAR 19 1- -1- 1-PHENYL-1-XYLYL ETHANE BENZENETRICARBOXYLIC 20 ACID, TRIOCTYL ESTER 21 CASTOR OIL IMIDAZOLIUM COMPOUNDS, 1- -4,5- -1- 1-BENZYL-4,5-DIHYDRO-1-(H 22 -2- YDROXYETHYL)-2-NORCOC O ALKYL, CHLORIDES 4 2-PROPENOIC ACID 2- POLYMER WITH 4- 1,1- 4-(1,1-DIMETHYLETHYL)PHE 2,5- NOL,FORMALDEHYDE, 23 2- 2,5-FURANDIONE, 65% / 2-METHYLOXIRANE AND OXIRANE (65% IN NAPHTHA/XYLENE) 24 n-PENTYL PROPIONATE 25 -2- 2-ETHYLHEXYL ACRYLATE 26 DECYL ACRYLATE 27 RAPESEED OIL RAPESEED OIL (low erucic acid 4% 28 containing less than 4% free fatty acids) RAPE SEED OIL FATTY ACID 29 METHYL ESTERS ALCOHOLS (C12-C13), C12-C13 30 PRIMARY, LINEAR AND ESSENTIALLY LINEAR 31 C13+ ALCOHOLS (C13+) 5 ALCOHOLS (C14-C18), C14-C18 32 PRIMARY, LINEAR AND ESSENTIALLY LINEAR ALCOHOLS (C8-C11), C8-C11 33 PRIMARY, LINEAR AND ESSENTIALLY LINEAR ACID OIL MIXTURE FROM SOYABEAN, CORN (maize) 34 AND SUNFLOWER OIL REFINING NAPHTHALENE CRUDE 35 (MOLTEN) 36 SOYABEAN OIL SOYBEAN OIL FATTY ACID 37 METHYL ESTER 38 BUTYLBENZENE (all isomers) 39 TALLOW 40 TALLOW FATTY ACID (2- BIS(2-ETHYLHEXYL) 41 ) TEREPHTHALATE 42 -(2- ) DI-(2-ETHYLHEXYL)
    [Show full text]
  • The Detection and Determination of Esters
    Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1958 The etD ection and Determination of Esters. Mohd. Mohsin Qureshi Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Qureshi, Mohd. Mohsin, "The eD tection and Determination of Esters." (1958). LSU Historical Dissertations and Theses. 501. https://digitalcommons.lsu.edu/gradschool_disstheses/501 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. Copright by Mohcl Mohsin Qureshi 1959 THE DETECTION AND DETERMINATION OF ESTERS A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemistry by Mohd. Mohsin Qureshi M.Sc., Aligarh University, 1944 August, 1958 ACKNOWLEDGMENT The author wishes to express his sincere apprecia­ tion and gratitude to Dr. Philip W. West under whose guidance this research was carried out. He is grateful to Dr. James G. Traynham for sup­ plying him with a number of esters and for his many helpful suggestions. The financial support given to him by the Continental Oil Company is gratefully acknowledged. He offers his sincere thanks to Miss Magdalena Usategul for her valuable suggestions and her ungrudging help during the course of this investigation. Dr. Anil K.
    [Show full text]
  • Impact of Sulfur Dioxide Oxidation by Stabilized Criegee Intermediate on Sulfate 2 3 Golam Sarwar 1*, Heather Simon 2, Kathleen Fahey 1, Rohit Mathur 1,Wendy S
    1 Impact of sulfur dioxide oxidation by Stabilized Criegee Intermediate on sulfate 2 3 Golam Sarwar 1*, Heather Simon 2, Kathleen Fahey 1, Rohit Mathur 1,Wendy S. Goliff 3,William R. 4 Stockwell 4 5 6 7 1Atmospheric Modeling and Analysis Division, National Exposure Research Laboratory, U.S. Environmental 8 Protection Agency, RTP, NC 27711, USA. 9 10 2Office of Air Quality Planning and Standards, U.S. Environmental Protection Agency, Research Triangle Park, 11 North Carolina, USA. 12 13 3College of Engineering Center for Environmental Research and Technology, University of California at Riverside, 14 Riverside, CA 92507, USA. 15 16 4Department of Chemistry, Howard University, Washington, DC 20059, USA. 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 ______________________________ 45 46 *Corresponding author : Golam Sarwar, U.S. EPA, 109 T.W. Alexander Drive, Research 47 Triangle Park, NC 27711, USA; Tel.: 919-541-2669; fax: 919-541-1379; e-mail : 48 [email protected] 49 - 1 - 50 Abstract 51 We revise the Carbon Bond chemical mechanism to explicitly represent three Stabilized Criegee 52 Intermediates (SCIs) and their subsequent reactions with sulfur dioxide, water monomer, and 53 water dimer, and incorporate the reactions into the Community Multiscale Air Quality model. 54 The reaction of sulfur dioxide with SCI produces sulfuric acid which partitions into sulfate. We 55 examine the impact of sulfur dioxide oxidation by SCI on sulfate using two different measured 56 rate constants for the reaction of sulfur dioxide and SCI.
    [Show full text]
  • General Disclaimer One Or More of the Following Statements May Affect
    General Disclaimer One or more of the Following Statements may affect this Document This document has been reproduced from the best copy furnished by the organizational source. It is being released in the interest of making available as much information as possible. This document may contain data, which exceeds the sheet parameters. It was furnished in this condition by the organizational source and is the best copy available. This document may contain tone-on-tone or color graphs, charts and/or pictures, which have been reproduced in black and white. This document is paginated as submitted by the original source. Portions of this document are not fully legible due to the historical nature of some of the material. However, it is the best reproduction available from the original submission. Produced by the NASA Center for Aerospace Information (CASI) NASA CR - 159480 EXXON/GRUS. 1KWD. 78 NIGH PERFORMANCE, HIGH DENSITY HYDROCARBON FUELS J. W. Frankenfeld, T. W. Hastings, M. Lieberman and W. F. Taylor EXXON RESEARCH AND ENGINEERING COMPANY prepared for NATIONAL AERONAUTICS AND SPACE ADMINISTRATION (NASA-CR-159''PO) HIGH PEPPOFMANCF, HIGH V79-20267 DENSTTv HYDR I-CARBON FTIELS (Exxon P.esearch and Engineering Co.) 239 rp HC A11/MF A01 CSCL 21D 'Inclas G3/28 19456 NASA Lewis Research Center Contract NAS 3-20394 Qnr{l,,Y^ ^'Pr I€ ^i NASA CR - 159480 EXXON/GRUS . 1KWD . 78 L: HIGH PERFORMANCE, HIGH DENSITY HYDROCARBON FUELS J. W. Frankenfeld, T. W. Hastings, M. Lieberman and W. F. Taylor EXXON RESEARCH AND ENGINEERING COMPANY prepared for NATIONAL AERONAUTICS AND SPACE ADMINISTRATION NASA Lewis Research Center Contract NAS 3-20394 FOREWARD The research described in this report was performed at Exxon Research and Engineering Company, Linden, New Jersey and Contract NAS 320394 with Mr.
    [Show full text]
  • Dibasic Acids for Nylon Manufacture
    - e Report No. 75 DIBASIC ACIDS FOR NYLON MANUFACTURE by YEN-CHEN YEN October 1971 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE MENLO PARK, CALIFORNIA CONTENTS INTRODUCTION, ....................... 1 SUMMARY .......................... 3 General Aspects ...................... 3 Technical Aspects ..................... 7 INDUSTRY STATUS ...................... 15 Applications and Consumption of Sebacic Acid ........ 15 Applications and Consumption of Azelaic Acid ........ 16 Applications of Dodecanedioic and Suberic Acids ...... 16 Applications of Cyclododecatriene and Cyclooctadiene .... 17 Producers ......................... 17 Prices ........................... 18 DIBASIC ACIDS FOR MANUFACTURE OF POLYAMIDES ........ 21 CYCLOOLIGOMERIZATIONOF BUTADIENE ............. 29 Chemistry ......................... 29 Ziegler Catalyst ..................... 30 Nickel Catalyst ..................... 33 Other Catalysts ..................... 34 Co-Cyclooligomerization ................. 34 Mechanism ........................ 35 By-products and Impurities ................ 37 Review of Processes .................... 38 A Process for Manufacture of Cyclododecatriene ....... 54 Process Description ................... 54 Process Discussion .................... 60 Cost Estimates ...................... 60 A Process for Manufacture of Cyclooctadiene ........ 65 Process Description ................... 65 Process Discussion .................... 70 Cost Estimates ...................... 70 A Process for Manufacture of Cyclodecadiene
    [Show full text]
  • United States Patent 0 Patented Feb
    2,874,164 United States Patent 0 Patented Feb. 17, 1959 1 2 Another object of the present invention is to provide such processes in which the amount of a speci?c diluent 2,874,164 to e?iciently suppress combustion can be readily deter PREVENTION OF COMBUSTION 1N mine for a given system containing ?lms of known ozo OXYGEN-OZONE MIXTURES nides or ozonide decomposition products having ascer tainable ignition temperatures. Victor A. Hann, St. Davids, Pa., assignor to The Welsbach Other and further objects of the present invention will Corporation, Philadelphia, Pa., a corporation of Dela appear from the following description of illustrative em ware bodiments of the same. No Drawing. Application August 21, 1956 10 The processes of the present invention are capable of Serial No. 605,423 various procedural embodiments without departing from the present inventive concept and reference should there 8 Claims. (Cl. 260—339) fore be had to the appended claims to determine the scope of this invention. _ This invention relates to processes for the prevention 15 As noted above, the ?lms containing ozonides or ozo of combustion in oxygen-ozone mixtures and more par nide decomposition products in the presence of an oxy ticularly to the prevention of combustion in systems con gen'ozone atmosphere act like a combustible mixture taminated by ozonides or their decomposition products although there is apparently insu?icient organic matter formed during the oxidation of unsaturated organic ma in the gas phase to constitute a combustible mixture. terials by oxygen-ozone mixtures and is a continuation 20 These ?lms contain ascertainable proportions of ozonides in-part of my co-pending application Serial No.
    [Show full text]
  • Advanced Oxidation Process for Small Compactor/Dumpster/Waste Storage Area Lift Station Bacteria, Virus & Odor Abatement System
    BOSII Advanced Oxidation Process for Small Compactor/Dumpster/Waste Storage Area Lift Station Bacteria, Virus & Odor Abatement System RGF has been an International leader in inno- vative environmental systems since 1985 Best warranty in the industry - two (2) full years parts and labor Fully automatic, easy to use and install, versa- tile and portable No costly and complicated chemicals Leaves no residue / operates unattended BOSII uses Photohydroionization®, nature’s natural deodorizer, environmentally friendly Low power consumption, 110 or 220 volt Low maintenance - only one filter to clean yearly cell replacement 3 year continuous operation average Photohy- BACTERIA / ODOR ABATEMENT SYSTEM droionization® Cell life - FOR - Advanced Oxidation gases actually destroys LIFT STATIONS, DUMPSTERS, FOOD PROCESSING, RESTAURANTS, HOTELS, NURSING HOMES, RECYCLE odor molecules, it is not a cover-up CENTERS, FAST FOOD, SUPERMARKETS, LAUNDRIES… PhotohydroionizationTM destroys bacteria, just to name a few. viruses, mold, organic pollutants and odors THE BOS PHOTOHYDROIONIZATION® MODULE WILL DESTROY, NOT JUST COVER-UP, THE FOLLOWING AIRBORNE SUBSTANCES: •DECOMPOSING ORGANICS •FUNGUS •SMOKE •YEAST •MOLD & MILDEW •POLLEN •BACTERIA •HYDROCARBONS •ALGAE •KETONES •URINE / FECES •SPORES •CHEMICAL FUMES •VOC's THE BOSII SYSTEM OF LOW COST ADVANCED OXIDATION PRODUCTION IS DE- SIGNED TO PROVIDE COMMERCIAL AIRBORNE BACTERIA AND ODOR DESTRUCTION BOSII Lab Results Odor reduction (Hydrogen Sulfide) Before and after bacteria samples application of BOSII unit to commercial dumpster compactor * Independent Lab data available Outstanding Features HOURS • No Costly Chemicals • Low Maintenance - Monthly filter cleaning, • All stainless steel PHI Cell replacement 3 years • Automatic Unattended Operation • Reduces Fly Infestation • Safety Service Cut Off Switch • Reduces airborne bacteria • 2 Year Limited Warranty • Reduces liability • Destroys Odors- Is Not a Cover Up • Eliminates odors • Economical to Use Specifications MODEL BOSII VOLTAGE 110V 60 HZ 3 AMPS WEIGHT 10 LBS.
    [Show full text]
  • Chemical Chemical Hazard and Compatibility Information
    Chemical Chemical Hazard and Compatibility Information Acetic Acid HAZARDS & STORAGE: Corrosive and combustible liquid. Serious health hazard. Reacts with oxidizing and alkali materials. Keep above freezing point (62 degrees F) to avoid rupture of carboys and glass containers.. INCOMPATIBILITIES: 2-amino-ethanol, Acetaldehyde, Acetic anhydride, Acids, Alcohol, Amines, 2-Amino-ethanol, Ammonia, Ammonium nitrate, 5-Azidotetrazole, Bases, Bromine pentafluoride, Caustics (strong), Chlorosulfonic acid, Chromic Acid, Chromium trioxide, Chlorine trifluoride, Ethylene imine, Ethylene glycol, Ethylene diamine, Hydrogen cyanide, Hydrogen peroxide, Hydrogen sulfide, Hydroxyl compounds, Ketones, Nitric Acid, Oleum, Oxidizers (strong), P(OCN)3, Perchloric acid, Permanganates, Peroxides, Phenols, Phosphorus isocyanate, Phosphorus trichloride, Potassium hydroxide, Potassium permanganate, Potassium-tert-butoxide, Sodium hydroxide, Sodium peroxide, Sulfuric acid, n-Xylene. Acetone HAZARDS & STORAGE: Store in a cool, dry, well ventilated place. INCOMPATIBILITIES: Acids, Bromine trifluoride, Bromine, Bromoform, Carbon, Chloroform, Chromium oxide, Chromium trioxide, Chromyl chloride, Dioxygen difluoride, Fluorine oxide, Hydrogen peroxide, 2-Methyl-1,2-butadiene, NaOBr, Nitric acid, Nitrosyl chloride, Nitrosyl perchlorate, Nitryl perchlorate, NOCl, Oxidizing materials, Permonosulfuric acid, Peroxomonosulfuric acid, Potassium-tert-butoxide, Sulfur dichloride, Sulfuric acid, thio-Diglycol, Thiotrithiazyl perchlorate, Trichloromelamine, 2,4,6-Trichloro-1,3,5-triazine
    [Show full text]
  • Pacs by Chemical Name (Mg/M3) (Pdf)
    Table 4: Protective Action Criteria (PAC) Rev 25 based on applicable 60-minute AEGLs, ERPGs, or TEELs. Values are presented in mg/m3. August 2009 Table 4 is an alphabetical listing of the chemicals in the PAC data set. It provides Chemical Abstract Service Registry Numbers (CASRNs)1, PAC values, and technical information on the source of the PAC values. Table 4 presents all values for TEEL-0, PAC-1, PAC-2, and PAC-3 in mg/m3. The conversion of ppm to mg/m3 is calculated assuming 25 ºC and 760 mm Hg. The columns presented in Table 4 provide the following information: Heading Definition No. The ordered numbering of the chemicals as they appear in this alphabetical listing. Chemical Name The chemical name given to the PAC Development Team. CASRN The Chemical Abstract Service Registry Number for this chemical. TEEL-0 This is the threshold concentration below which most people will experience no adverse health effects. This PAC is always based on TEEL-0 because AEGL-0 or ERPG-0 values do not exist. PAC-1 Based on the applicable AEGL-1, ERPG-1, or TEEL-1 value. PAC-2 Based on the applicable AEGL-2, ERPG-2, or TEEL-2 value. PAC-3 Based on the applicable AEGL-3, ERPG-3, or TEEL-3 value. Source of PACs: Technical comments provided by the PAC development team that TEEL-0, PAC-1, indicate the source of the data used to derive PAC values. Future efforts PAC-2, PAC-3 are directed at reviewing, revising, and enhancing this information.
    [Show full text]
  • Flammable Liquids and Solids Chemical Class Standard Operating Procedure
    1 Flammable Liquids and Solids Chemical Class Standard Operating Procedure Flammable Liquids and Solids H224 H225 H226 H227 H228 This SOP is not a substitute for hands-on training. Print a copy and insert into your laboratory SOP binder. Department: Chemistry Date SOP was written: Thursday, July 1, 2021 Date SOP was approved by PI/lab supervisor: Thursday, July 1, 2021 Name: F. Fischer Principal Investigator: Signature: ______________________________ Name: Matthew Rollings Internal Lab Safety Coordinator or Lab Manager: Lab Phone: 510.301.1058 Office Phone: 510.643.7205 Name: Felix Fischer Emergency Contact: Phone Number: 510.643.7205 Tan Hall 674, 675, 676, 679, 680, 683, 684 Location(s) covered by this SOP: Hildebrand Hall: D61, D32 1. Purpose This SOP covers the precautions and safe handling procedures for the use of Flammable Liquids and Solids. For a list of Flammable Liquids and Solids covered by this SOP and their use(s), see “List of Chemicals”. Procedures described in Section 12 apply to all materials covered in this SOP. A change to the “List of Chemicals” does not constitute a change in the SOP requiring review or retraining. If you have questions concerning the applicability of any recommendation or requirement listed in this procedure, contact the Principal Investigator/Laboratory Supervisor or the campus Chemical Hygiene Officer at [email protected]. Rev. Date: 2021-06-29 2 Flammable Liquids and Solids Chemical Class Standard Operating Procedure 2. Physical & Chemical Properties/Definition of Chemical Group Flammable liquid means a liquid having a flash point1 of not more than 199.4 °F (93 °C).
    [Show full text]
  • Accuracy and Methodologic Challenges of Volatile Organic Compound–Based Exhaled Breath Tests for Cancer Diagnosis: a Systematic Review and Pooled Analysis
    1 Supplementary Online Content Hanna GB, Boshier PR, Markar SR, Romano A. Accuracy and Methodologic Challenges of Volatile Organic Compound–Based Exhaled Breath Tests for Cancer Diagnosis: A Systematic Review and Pooled Analysis. JAMA Oncol. Published online August 16, 2018. doi:10.1001/jamaoncol.2018.2815 Supplement. eTable 1. Search strategy for cancer systematic review eTable 2. Modification of QUADAS-2 assessment tools eTable 3. QUADAS-2 results eTable 6. STARD assessment of each study eTable 7. Summary of factors reported to influence levels of volatile organic compounds within exhaled breath eFigure 1. Risk of bias and applicability concerns using QUADAS-2 eFigure 2. PRISMA flowchart of literature search eTable 4. Details of studies on exhaled volatile organic compounds in cancer eTable 5. Cancer VOCs in exhaled breath and their chemical class. eFigure 3. Chemical classes of VOCs reported in different tumor sites. This supplementary material has been provided by the authors to give readers additional information about their work. © 2018 American Medical Association. All rights reserved. Downloaded From: https://jamanetwork.com/ on 10/01/2021 2 eTable 1. Search strategy for cancer systematic review # Search 1 (cancer or neoplasm* or malignancy).ab. 2 limit 1 to abstracts 3 limit 2 to cochrane library [Limit not valid in Ovid MEDLINE(R),Ovid MEDLINE(R) Daily Update,Ovid MEDLINE(R) In-Process,Ovid MEDLINE(R) Publisher; records were retained] 4 limit 3 to english language 5 limit 4 to human 6 limit 5 to yr="2000 -Current" 7 limit 6 to humans 8 (cancer or neoplasm* or malignancy).ti. 9 limit 8 to abstracts 10 limit 9 to cochrane library [Limit not valid in Ovid MEDLINE(R),Ovid MEDLINE(R) Daily Update,Ovid MEDLINE(R) In-Process,Ovid MEDLINE(R) Publisher; records were retained] 11 limit 10 to english language 12 limit 11 to human 13 limit 12 to yr="2000 -Current" 14 limit 13 to humans 15 7 or 14 16 (volatile organic compound* or VOC* or Breath or Exhaled).ab.
    [Show full text]