NITED STATES PATENT OFFICE J

Total Page:16

File Type:pdf, Size:1020Kb

NITED STATES PATENT OFFICE J Patented Feb. 20, 1945 2,369,919 U NITED STATES PATENT OFFICE j _ 2,369,919 KETOETHENONES AND rnoonss 'rnnanroa John Carl Sauer, Wilmington, Del., assignor to E. I. du Pont de Nemours & Company, Wilming ton, Del.. a corporation of Delaware No Drawing. Application October 13, 1938, Serial No. 234,843 ' 2 Claims. (Cl. 260-550) This invention relates to organic compounds ployed or in 30 minutes when the reaction is car ried out in re?uxing benzene or xylene with a and more particularly to certain disubstituted trialkylamine such as triethylamine. Higher ethenones, i. e., ketoethenones. Numerous investigations into the dehydrohalo - temperatures promote a more rapid reaction. A genation of primary acid halides,3i. e., those in test which may be applied to determine the end which .the acid halide group ' point is to withdraw a sample of t ev reaction mixture, ?lter it, add a small amount of amine to the ?ltrate, and boil- If no precipitate forms, (H) . -o-x the reaction is substantially complete. The higher substituted ethenones are conveniently (X being a halogen) is attached to a methylene puri?ed by recrystallization, and distillation is group, have been made, but there is no record usually unnecessary. - of the preparation of low melting dehydrohalo The lower acyl halides such as propanoyl chlo= genation products of monosubstituted ethanoyl ride are very reactive towards tertiary aliphatic halides. ' ‘ I 15 amines and are best dehydrohalogenated under This invention has as an object the prepara re?ux by adding the amine to the acyl halide tion of low melting intermolecular dehydrohalo solution (or vice versa) just fast enough to keep genation products of primary acid halides. A the solvent gently re?uxing when low boiling further object is the provision of a process there solvents such as diethyl ether are employed. for. Another object is the preparation of inter 20 With high boiling solvents such as dichloroben mediates for dyes and other useful organic chem zene, any suitable and convenient rate of addi icals. Qther objects will appear hereinafter. tion of the one reactant to the other may be These objects are accomplished by the follow employed. The lower acyl halides as a rule are ing invention which comprises reacting a tertiary completely dehydrohalogenated with trimethyl aliphatic amine free from active hydrogen under 25 amine within a few minutes at room tempera anhydrous conditions with a primary monoacyl tures. ' halide R—CH2—CO—X, where X is a halogen The more detailed practice of the invention is and R is a monovalent organic radical‘which, illustrated by the following examples, wherein at temperatures up‘to 170° C., is chemically inert parts given are by weight unless otherwise stated. to tertiary amines, acyl halides, and ethenones, 30 There are of course many forms of the invention and isolating, also under anhydrous conditions, other than these speci?c embodiments. the resulting intermolecular dehydrohalogena tion product, i. e., the disubstituted ethenone.v EXAMPLE ,I v The nature of the suitable amines and acid hal Dodecdnoyldecylethenone ides is more precisely explained hereinafter. 35 The reaction is carried out in the case of the C11H2sCOC(C1aH21)=@Q higher acid halides, i. e. of at least eight carbon To n-dodecanoyl chloride (43.6 parts) in an atoms (octanoyl and higher‘ halides) by dissolv hydrous ether (350 parts) is added triethylamine ing the acyl halide in an inert solvent and add ‘(20.6 :parts). These materials are thoroughly ing a chemically equivalent amount of the ter 40 mixed out of contact with air, then left at room _' tiary aliphatic amine with exclusion of moisture, temperature for 3 days. Filtration yields tri 1. e., under anhydrous conditions. The acyl hal ethylamine hydrochloride (28 parts or the theo ide may also be added to the amine in‘ an inert retical am'ount) melting at 251-4° C. When the solvent. The reaction mixture is agitated and solvent is evaporated from the filtrate in vacuo if necessary cooled to abstract the heat of reac 45 and the residue crystallized from ‘acetone, do tion. At 0°~25° C., the time required for com decanoyldecylethenone, a compound of the above plete reaction varies from 1-16 hours, depending .' probable formula and melting at 41-42’ C. is ob on the acyl halide and-amine used. Dehyd'ro tained in 90% yield. This compound was found halogenation is usually complete in an hour at on analysis to contain 78.78% carbon and 12.19% room temperature when trimethylamine is em 50 hydrogen. and to have a molecular weight of 2 ' 2,869,919 351. The calculated values are 79.10%, 12.09%, Exmrta IV and 364, respectively. The following table lists the proportions of 3-methylbutanolllisopfomllethenone reactants used and the yields of dodecanoyldecyl CHa-CH(CH3) CHzCOC(CH(CH3) 2) =C=O ethenone obtained from dodecanoyl chloride in 5 To 3-methylbutanoyl chloride (216 parts) in similar experiments. anhydrous ether (715 parts) is added gaseous an Pms Amine Solvent Reaction Per n‘dodecan- ' cent oyl chlonde Nature Parts Nature Parts Time Temp. yield Hours ‘’ C. 6 Ethyl ether. 160 25 78 6 Benzene"... 160 25 78 e Ethyl ether. 160 25 ‘7s 6. 9 Benzene“... 100 l 78 92 8 Xylene ____ -_ 110 l 135 100 Exmu: II hydrous trimethylamine with stirring until all 0ctadecanoylhewadecylethenone and its deriva evidence of reaction ceases. The resulting mix 20 ture is allowed to stand at room temperature for tives CI7H3SCOC(C16H33) =C=O 16 hours, the trimethylamine hydrochloride ?l To n-octadecanoyl chloride (15 parts) in an tered off, and the solvent evaporated from the hydrous benzene (180 parts) is added triethyl ?ltrate. The residue, amounting to 28 parts or a amine (6 parts) .- Dehydrohalogenation com 60% yield, is 3amethylbutanoylisopropylethenone mences almost immediately, and the reaction of the above probable formula. It boils at mixture is permitted to stand at room tempera 108-,110n C./35 mm., has an index of refraction, ture for 16 hours. After ?ltering out 6.9 parts ND25, of 1.4343, and a molecular weight of 163 of triethylamine hydrochloride (the theoretical ‘ (calculated value 168). This substituted ethenone ~ yield), the ?ltrate is concentrated on a steam may readily be converted into alpha-isovaleryl bath in vacuo, and the residue is taken up in pe isovaleranilide (M. P. 105-6° C.) by reaction with troleum ether (32 parts). Upon cooling, 12 parts aniline and into ethyl alpha-isovalerylisovalerate or a 97% yield of octadecanoylhexadecyleth (B. P. 135° C./32 mm.) by reaction with ethyl al enone, a compound of the above probable formula cohol. The former compound had a nitrogen and melting at 62-3° C., is obtained. It was content of 5.7%. and the latter a saponi?cation found to have a molecular weight of 494 and car number of 265, values which check closely with bon and hydrogen contents of 80.4% and 12.3%.. the theoretical. The identity of these derivatives The calculated values are 532, 81.1% and 12.7%, further characterizes the substituted ethenone. respectively. In the preparation of many chem EXAMPLE V ical derivatives, e. g., from amines and hy droxylated compounds, it is not necessary to iso 40 Propanoylmethylethenone late the substituted ethenone from’ the solvent. CH3CH2C0C(CH3) =C'=O Thus, to a, portion of the ?ltrate containing the Triethylamine (200 parts) is added slowly and octadecanoylhexadecylethenone is added a with agitation over a period of 2 to 3 hours to a chemically equivalent amount of aniline. The mixture of anhydrous ether. (980 parts) and compound alpha-octadecanoylstearanilide pre propanoyl chloride (179 parts) contained in a re cipitates from the solution and melts at 77-8“ C. action vessel ?tted with a re?ux condenser, a after recrystallization from alcohol. It has a ni stirrer, and a means for slowly adding the amine. trogen content of 2.6%, which checks the theo After the mixture has stood at room temperature retical within experimental error. for 20 hours, ?ltration by the “inverted method” In Example II above, octadecanoyl bromide described in Organic Syntheses, vol. XVI, p. 82, may be substituted for octadecanoyl chloride, and is employed, and the theoretical amount of tri the same compound obtained in yields of around ethylamine hydrochloride is separated. On 80%. Ether or benzene may be used as the sol evaporating the "solvent from the ?ltrate, there vent. _ I is obtained 75 parts or a 74% yield of alpha EXAMPLE III propanoylmethylethenone, a compound of the Octanwlhexillethenone above probable formula, 13. P. 57-8° C./12 mm. C1H15COC'(C'aH13) =C=O and ND25 1.4280. It was found to have a molecu lar weight of 114, and carbon and hydrogen con To n-octanoyl chloride (53 parts) in 355 parts tents of 63.88% and 7.61%. The calculated values of anhydrous ether is added triethylamine (34 are 112, 64.29%, and.'1.15%, respectively. parts). The reaction mixture is agitated out of Any solvent which dissolves and is inert toward contact with air and cooled in ice for 20 minutes acyl halides, tertiary amines, and ethenones is to offset the heat of reaction. The mixture is operable. Thus, a wide variety of solvents, in set aside for 2 days at room temperature, and cluding ethers, aromatic or aliphatic hydrocar the triethylamine hydrochloride then ?ltered off, bons, aromatic or aliphatic chlorinated hydrocar 96% of the theoretical amount being obtained. ' hons containing inactive halogen atoms, such as The solvent is evaporated from the ?ltrate. The trichlorethylene or carbon tetrachloride, are suit . residue (15 parts, or 75% yield) .is octanoyl-' able, Chlorinated hydrocarbons not suitable as hexylethenone, a compound of the above probable solvents include benzyl chloride and alpha- or formula.
Recommended publications
  • EPA Handbook: Optical and Remote Sensing for Measurement and Monitoring of Emissions Flux of Gases and Particulate Matter
    EPA Handbook: Optical and Remote Sensing for Measurement and Monitoring of Emissions Flux of Gases and Particulate Matter EPA 454/B-18-008 August 2018 EPA Handbook: Optical and Remote Sensing for Measurement and Monitoring of Emissions Flux of Gases and Particulate Matter U.S. Environmental Protection Agency Office of Air Quality Planning and Standards Air Quality Assessment Division Research Triangle Park, NC EPA Handbook: Optical and Remote Sensing for Measurement and Monitoring of Emissions Flux of Gases and Particulate Matter 9/1/2018 Informational Document This informational document describes the emerging technologies that can measure and/or identify pollutants using state of the science techniques Forward Optical Remote Sensing (ORS) technologies have been available since the late 1980s. In the early days of this technology, there were many who saw the potential of these new instruments for environmental measurements and how this technology could be integrated into emissions and ambient air monitoring for the measurement of flux. However, the monitoring community did not embrace ORS as quickly as anticipated. Several factors contributing to delayed ORS use were: • Cost: The cost of these instruments made it prohibitive to purchase, operate and maintain. • Utility: Since these instruments were perceived as “black boxes.” Many instrument specialists were wary of how they worked and how the instruments generated the values. • Ease of use: Many of the early instruments required a well-trained spectroscopist who would have to spend a large amount of time to setup, operate, collect, validate and verify the data. • Data Utilization: Results from path integrated units were different from point source data which presented challenges for data use and interpretation.
    [Show full text]
  • Preparation and Purification of Atmospherically Relevant Α
    Atmos. Chem. Phys., 20, 4241–4254, 2020 https://doi.org/10.5194/acp-20-4241-2020 © Author(s) 2020. This work is distributed under the Creative Commons Attribution 4.0 License. Technical note: Preparation and purification of atmospherically relevant α-hydroxynitrate esters of monoterpenes Elena Ali McKnight, Nicole P. Kretekos, Demi Owusu, and Rebecca Lyn LaLonde Chemistry Department, Reed College, Portland, OR 97202, USA Correspondence: Rebecca Lyn LaLonde ([email protected]) Received: 31 July 2019 – Discussion started: 6 August 2019 Revised: 8 December 2019 – Accepted: 20 January 2020 – Published: 9 April 2020 Abstract. Organic nitrate esters are key products of terpene oxidation in the atmosphere. We report here the preparation and purification of nine nitrate esters derived from (C)-3- carene, limonene, α-pinene, β-pinene and perillic alcohol. The availability of these compounds will enable detailed investigations into the structure–reactivity relationships of aerosol formation and processing and will allow individual investigations into aqueous-phase reactions of organic nitrate esters. Figure 1. Two hydroxynitrate esters with available spectral data. Relative stereochemistry is undefined. 1 Introduction derived ON is difficult, particularly due to partitioning into the aerosol phase in which hydrolysis and other reactivity Biogenic volatile organic compound (BVOC) emissions ac- can occur (Bleier and Elrod, 2013; Rindelaub et al., 2014, count for ∼ 88 % of non-methane VOC emissions. Of the to- 2015; Romonosky et al., 2015; Thomas et al., 2016). Hydrol- tal BVOC estimated by the Model of Emission of Gases and ysis reactions of nitrate esters of isoprene have been stud- Aerosols from Nature version 2.1 (MEGAN2.1), isoprene is ied directly (Jacobs et al., 2014) and the hydrolysis of ON estimated to comprise half, and methanol, ethanol, acetalde- has been studied in bulk (Baker and Easty, 1950).
    [Show full text]
  • Volatile Organic Compound Production in Synechococcus WH8102
    Volatile Organic Compound Production in Synechococcus WH8102 by Duncan Ocel A THESIS submitted to Oregon State University Honors College in partial fulfillment of the requirements for the degree of Honors Baccalaureate of Science in Chemistry and Botany (Honors Scholar) Presented May 21, 2018 Commencement June 2018 2 3 AN ABSTRACT OF THE THESIS OF Duncan Ocel for the degree of Honors Baccalaureate of Science in Chemistry and Botany presented on May 21, 2018. Title: Volatile Organic Compound Production in Synechococcus WH8102. Abstract approved:_____________________________________________________ Kimberly Halsey High-resolution mass spectrometry was used to measure a range of volatile organic compounds (VOCs) in real time as they were produced by the ubiquitous marine cyanobacterium Synechococcus WH8102 during a 24-hour light/dark cycle. Ethenone, acetaldehyde, ethanol, isoprene, acetic acid, dimethyl sulfide (DMS), acetone, phenol, and several as-yet unidentified compounds were measured in higher concentration in live cultures than in azide-killed cultures or sterile artificial seawater. Several compounds were found in higher concentration in the daylight part of the diel cycle than in the night, suggesting VOCs are produced during active photosynthesis. Key Words: phytoplankton, volatile organic compounds, Synechococcus, acetaldehyde, dimethyl sulfide Corresponding e-mail address: [email protected] 4 ©Copyright by Duncan Ocel May 21,2018 All Rights Reserved 5 Volatile Organic Compound Production in Synechococcus WH8102 by Duncan Ocel A THESIS submitted to Oregon State University Honors College in partial fulfillment of the requirements for the degree of Honors Baccalaureate of Science in Chemistry and Botany (Honors Scholar) Presented May 21, 2018 Commencement June 2018 6 Honors Baccalaureate of Science in Chemistry and Botany project of Duncan Ocel presented on May 21, 2018.
    [Show full text]
  • Oxidation of N-Butylcyclohexane in the Low Temperature Region
    CORE Metadata, citation and similar papers at core.ac.uk Provided by Drexel Libraries E-Repository and Archives Oxidation of n-Butylcyclohexane in the Low Temperature Region A Thesis Submitted to the Faculty of Drexel University by Robert Harris Natelson in partial fulfillment of the requirements for the degree of Doctor of Philosophy May 2010 © Copyright 2010 Robert H. Natelson. All Rights Reserved. ii DEDICATIONS This work is dedicated to my mom and dad. iii ACKNOWLEDGMENTS I would first like to thank my advisors Dr. Nicholas P. Cernansky and Dr. David L. Miller for providing me the opportunity to conduct my graduate research studies under their guidance. Our lively discussions have been an important part of my learning process. I would also like to express my gratitude to my Ph.D. Defense committee, including Drs. Cernansky, Miller, Howard Pearlman, Ying Sun, and James Tangorra for their time, questions, and suggestions. I would also like to thank Dr. Vedha Nayagam at NASA Glenn Research Center for first introducing me to the research area of combustion. My colleague at Hess Lab, Matthew Kurman, has been an invaluable collaborator in my work, and I cannot imagine completing this study without his support in the laboratory. I would also like to acknowledge the thoughtful discussions I have had with my other Hess Lab friends, including Jamie Lane, Ashutosh Gupta, Rodney Johnson, David Lenhert, Xiaohui Gong, Jincai Zheng, Seuk Chun Choi, Yi Ma, Laton McGibbon, Kevin Wujcik, Brian Folkes, Haider Hasan, Farinaz Farid, and Julius Corrubia. The MEM department and Hess Lab staff, including Ms.
    [Show full text]
  • Preparation and Purification of Atmospherically Relevant Α
    Technical Note: Preparation and purification of atmospherically relevant a-hydroxynitrate esters of monoterpenes Elena Ali McKnight, Nicole P. Kretekos, Demi Owusu, Rebecca Lyn LaLonde 5 Chemistry Department, Reed College, Portland, OR, 97202, USA Correspondence to: Rebecca Lyn LaLonde ([email protected]) Abstract. Organic nitrate esters are key products of terpene oxidation in the atmosphere. We report here the preparation and purification of nine nitrate esters derived from (+)-3-carene, limonene, a-pinene, b-pinene and perillic alcohol. The availability of these compounds will enable detailed investigations into the structure 10 reactivity relationships of aerosol formation and processing and will allow individual investigations into aqueous phase reactions of organic nitrate esters. 1 Introduction Biogenic volatile organic compound (BVOC) emissions account for ~88% of non-methane VOC emissions. Of the total BVOC estimated by the Model of Emission of Gases and Aerosols from Nature version 2.1 15 (MEGAN2.1), isoprene is estimated to comprise half, and methanol, ethanol, acetaldehyde, acetone, a-pinene, b-pinene, limonene, ethene and propene together encompass another 30%. Of the terpenoids, a-pinene alone is estimated to generate ~66 Tg year -1 (Guenther et al., 2012). These monoterpenes can be oxidized by nitrate radicals that are projected to account for more than half of the monoterpene-derived secondary organic aerosol (SOA) in the US (Pye et al., 2010). Nitrate oxidation pathways have been shown to be important particularly 20 during nighttime. A large portion (30-40%) of monoterpene emissions occur at night (Pye et al., 2010). These emissions can then react with NO3 radicals, formed from the oxidation of NO2 emissions by O3, (Pye et al., 2010).
    [Show full text]
  • Article Is Available On- Line At
    Atmos. Chem. Phys., 21, 11505–11518, 2021 https://doi.org/10.5194/acp-21-11505-2021 © Author(s) 2021. This work is distributed under the Creative Commons Attribution 4.0 License. Unexplored volatile organic compound emitted from petrochemical facilities: implications for ozone production and atmospheric chemistry Chinmoy Sarkar1,a, Gracie Wong1, Anne Mielnik1, Sanjeevi Nagalingam1, Nicole Jenna Gross1, Alex B. Guenther1, Taehyoung Lee2, Taehyun Park2, Jihee Ban2, Seokwon Kang2, Jin-Soo Park3, Joonyoung Ahn3, Danbi Kim3, Hyunjae Kim3, Jinsoo Choi3, Beom-Keun Seo4, Jong-Ho Kim4, Jeong-Ho Kim5, Soo Bog Park4, and Saewung Kim1 1Department of Earth System Science, University of California Irvine, Irvine, CA 92697, USA 2Department of Environmental Science, Hankuk University of Foreign Studies, Yongin 17035, South Korea 3Air Quality Research Division, National Institute of Environmental Research, Incheon 22689, South Korea 4Institute of Environmental Research, Hanseo University, Seosan-si, South Korea 5APM Engineering Co. Ltd., Bucheon-si, South Korea anow at: Air Quality Research Center, University of California Davis, Shields Avenue, Davis, CA 95616, USA Correspondence: Chinmoy Sarkar ([email protected]), Jin-Soo Park ([email protected]), and Saewung Kim ([email protected]) Received: 22 October 2020 – Discussion started: 2 November 2020 Revised: 6 July 2021 – Accepted: 6 July 2021 – Published: 2 August 2021 Abstract. A compound was observed using airborne pro- potential to significantly influence local photochemistry, and ton transfer reaction time-of-flight mass spectrometry (PTR- therefore, further studies focusing on the photooxidation and TOF-MS) measurements in the emission plumes from the atmospheric fate of ketene through chamber studies are re- Daesan petrochemical facility in South Korea.
    [Show full text]
  • PDF (Detailed Experimental Procedures, Full
    CO Coupling Chemistry of a Terminal Mo Carbide: Sequential Addition of Proton, Hydride, and CO Releases Ethenone Joshua A. Buss, Gwendolyn A. Bailey, Julius Oppenheim, David G. VanderVelde, William A. Goddard III, and Theodor Agapie Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd. MC 127-72, Pasadena, CA, USA Supporting Information Contents Experimental Details S3 General Considerations S3 Carbide–CO Coupling from Carbide 1 S3 In situ generation of carbide 1 S3 Figure S1— Partial 13C{1H} (126 MHz, THF, -50 °C) and 31P{1H} (202 MHz, THF, -50 °C) NMR spectra showing clean deprotonation of methylidyne 4 with benzyl potassium. S4 Addition of CO to Carbide 1 to form Metallaketene Complex 2 S4 1 Figure S2— H NMR Spectrum (400 MHz, C6D6, 23 °C) of 2. S5 31 1 Figure S3— P{ H} NMR Spectrum (162 MHz, C6D6, 23 °C) of 2. S5 13 1 Figure S4— C{ H} NMR Spectrum (101 MHz, C6D6, 23 °C) of 2. S6 Figure S5—31P{1H} NMR spectrum (202 MHz, THF, 23 °C) of 2-13C. S6 Figure S6—13C{1H} NMR spectrum (126 MHz, THF, 23 °C) of 2-13C. S6 Preparation of a mixture predominantly of carbide isomer 3 S7 1 13 Figure S7— H NMR Spectrum (400 MHz, C6D6, 23 °C) of 3- C. S8 31 1 13 Figure S8— P{ H} NMR spectrum (162 MHz, C6D6, 23 °C) of 3- C. S8 13 1 13 Figure S9— C{ H} NMR spectrum (101 MHz, C6D6, 23 °C) of 3- C. S8 Sequential Addition of Proton, Hydride, and CO to Carbide 1 S9 Synthesis of Methylidyne 4 S9 1 Figure S10— H NMR Spectrum (300 MHz, C6D6, 23 °C) of 4.
    [Show full text]
  • Compilation of Chemical Kinetic Data for Combustion Chemistry. Part 2. Non-Aromatic C, H, O, N, and S Containing Compounds
    v NBS PUBLICATIONS r A111D2 TBOmi NAT'L INST OF STANDARDS & TECH R.I.C. All 102730091 Westley, Francls/Compllatlon of chemical 2 QC100 .11573 NO. 73 V2;1987 C.2 NBS-PUB-C NSRDS-NBS 73, Part U.S. DEPARTMENT OF COMMERCE / National Bureau of Standards 1 BB he National Bureau of Standards was established by an act of Congress on March 3, 1901. The Bureau’s overall M goal is to strengthen and advance the nation’s science and technology and facilitate their effective application for public benefit. To this end, the Bureau conducts research to assure international competidveness and leadership of U.S. industry, science arid technology. NBS work involves development and transfer of measurements, standards and related science and technology, in support of continually improving U.S. productivity, product quality and reliability, innovation and underlying science and engineering. The Bureau’s technical work is performed by the National Measurement Laboratory, the National Engineering Laboratory, the Institute for Computer Sciences and Technology, and the Institute for Materials Science and Engineering. The National Measurement Laboratory Provides the national system of physical and chemical measurement; • Basic Standards 2 coordinates the system with measurement systems of other nations and • Radiation Research furnishes essential services leading to accurate and uniform physical and • Chemical Physics chemical measurement throughout the Nation’s scientific community, • Analytical Chemistry industry, and commerce; provides advisory and research
    [Show full text]
  • Optical Gas Imaging
    OPTICAL GAS IMAGING Infrared Cameras for Gas Leak Detection MAKE INVISIBLE GASES VISIBLE SAVE LIVES, REVENUE, AND THE DAY A facility can have thousands of connections and fittings that require regular inspection, but the reality is only a small percentage of these components will ever leak. Testing them all with a traditional “sniffer” takes a great deal of time, effort and may put the inspector in an unsafe environment. SEE HYDROCARBON LEAKS CLEARLY FIND SF6 LEAKS EASILY FIND LEAKS AT STEEL PLANTS METHANE AND HYDROCARBONS SULFUR HEXAFLUORIDE (SF6) CARBON MONOXIDE (CO) Scan thousands of connections for natural gas Scan substation circuit breakers for sulfur hexafluoride Protect workers and the environment from toxic levels (methane) and other hydrocarbon leaks quickly and from (SF6) leaks at a safe distance from high-voltage areas, of carbon monoxide (CO) by pinpointing leaks quickly a safe distance to avoid regulatory violations, fines, and without the need to shut down operations. and efficiently. lost revenue. Optical gas imaging cameras give you the power to spot invisible gases as they escape, so you can find fugitive emissions faster and more reliably than with sniffer detectors. With a FLIR GF-Series camera, you can document gas leaks that lead to lost product, lost revenue, fines, and safety hazards. DETECT LEAKS FROM HYDROGEN-COOLED GENERATORS SPOT HARD-TO-FIND CO2 LEAKS DETECT R-124 COMPRESSOR LEAKS HYDROGEN (CO TRACER GAS) CARBON DIOXIDE (CO ) REFRIGERANTS From natural gas extraction to 2 2 petrochemical operations and power Imaging the tracer gas, CO2, with an optical gas camera Prevent shut-downs by detecting carbon dioxide Find leaks early to avoid interruptions in operations, generation, companies have saved allows operators of hydrogen-cooled generators to (CO2) leaks early in chemical production, manufacturing, and prevent the loss of perishable products, and limit the more than $10 million annually in lost efficiently find hydrogen leaks.
    [Show full text]
  • Hazardous Substance Fact Sheet
    Right to Know Hazardous Substance Fact Sheet Common Name: KETENE Synonyms: Carbomethene; Keten CAS Number: 463-51-4 Chemical Name: Ethenone RTK Substance Number: 1092 Date: June 2011 Revision: September 2016 DOT Number: None Description and Use EMERGENCY RESPONDERS >>>> SEE LAST PAGE Ketene is a colorless gas with a sharp, penetrating odor. It is Hazard Summary used to make other chemicals such as aspirin, acetates and Hazard Rating NJDHSS NFPA Acetic Anhydride. HEALTH 3 - FLAMMABILITY 3 - REACTIVITY 1 - FLAMMABLE POISONOUS GASES ARE PRODUCED IN FIRE CONTAINERS MAY EXPLODE IN FIRE Reasons for Citation POLYMERIZER Ketene is on the Right to Know Hazardous Substance List Hazard Rating Key: 0=minimal; 1=slight; 2=moderate; 3=serious; because it is cited by OSHA, ACGIH and NIOSH. 4=severe This chemical is on the Special Health Hazard Substance List. Ketene can affect you when inhaled. Contact can irritate the skin and eyes. Exposure to Ketene can irritate the nose and throat. Inhaling Ketene can irritate the lungs. Higher exposures may cause a build-up of fluid in the lungs (pulmonary edema), a medical emergency. Ketene is a FLAMMABLE GAS and a DANGEROUS FIRE HAZARD. Ketene can POLYMERIZE resulting in uncontrolled SEE GLOSSARY ON PAGE 5. reactions. These reactions may be explosive. FIRST AID Eye Contact Workplace Exposure Limits Immediately flush with large amounts of water for at least 15 OSHA: The legal airborne permissible exposure limit (PEL) is minutes, lifting upper and lower lids. Remove contact 0.5 ppm averaged over an 8-hour workshift. lenses, if worn, while rinsing. NIOSH: The recommended airborne exposure limit (REL) is Skin Contact 0.5 ppm averaged over a 10-hour workshift and Quickly remove contaminated clothing.
    [Show full text]
  • Acetic Acid/Propionic Acid Conversion on Metal Doped Molybdenum Carbide Catalyst Beads for Catalytic Hot Gas Filtration
    catalysts Communication Acetic Acid/Propionic Acid Conversion on Metal Doped Molybdenum Carbide Catalyst Beads for Catalytic Hot Gas Filtration Mi Lu 1,† , Andrew W. Lepore 2,†, Jae-Soon Choi 1 , Zhenglong Li 1, Zili Wu 2 , Felipe Polo-Garzon 2 and Michael Z. Hu 1,* 1 Energy and Transportation Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA; [email protected] (M.L.); [email protected] (J.-S.C.); [email protected] (Z.L.); [email protected] (M.Z.H.) 2 Chemical Science Division, Oak Ridge National Laboratory, Oak Ridge, TN 37830, USA; [email protected] (A.W.L.); [email protected] (Z.W.); [email protected] (F.P.-G.) * Correspondence: [email protected]; Tel.: +865-574-8782 † These authors contributed equally to this work. Received: 14 November 2018; Accepted: 7 December 2018; Published: 9 December 2018 Abstract: Catalytic hot gas filtration (CHGF) is used to precondition biomass derived fast pyrolysis (FP) vapors by physically removing reactive char and alkali particulates and chemically converting reactive oxygenates to species that are more easily upgraded during subsequent catalytic fast pyrolysis (CFP). Carboxylic acids, such as acetic acid and propionic acid, form during biomass fast pyrolysis and are recalcitrant to downstream catalytic vapor upgrading. This work developed and evaluated catalysts that can convert these acids to more upgradeable ketones at the laboratory scale. Selective catalytic conversion of these reactive oxygenates to more easily upgraded compounds can enhance bio-refinery processing economics through catalyst preservation by reduced coking from acid cracking, by preserving carbon efficiency, and through process intensification by coupling particulate removal with partial upgrading.
    [Show full text]
  • Table of Recommended Rate Constants for Chemical Reactions Occurring in Combustion
    A111D2 14bB cn 0- NATL INST OF STANMffii.SSJ All 1021 46399 1964 ffiSWR***""" NBS-PUB-C « JC $ to NSRDS-NBS 67 \ %J 0* U.S. DEPARTMENT OF COMMERCE / National Bureau of Standards U, 2 NATIONAL BUREAU OF STANDARDS The National Bureau of Standards' was established by an act of Congress on March 3, 1901. The Bureau's overall goal is to strengthen and advance the Nation's science and technology and facilitate their effective application for public benefit. To this end, the Bureau conducts research and provides: (1) a basis for the Nation’s physical measurement system, (2) scientific and technological services for industry and government, (3) a technical basis for equity in trade, and (4) technical services to promote public safety. The Bureau’s technical work is per- formed by the National Measurement Laboratory, the National Engineering Laboratory, and the Institute for Computer Sciences and Technology. THE NATIONAL MEASUREMENT LABORATORY provides the national system of physical and chemical and materials measurement; coordinates the system with measurement systems of other nations and furnishes essential services leading to accurate and uniform physical and chemical measurement throughout the Nation’s scientific community, industry, and commerce; conducts materials research leading to improved methods of measurement, standards, and data on the properties of materials needed by industry, commerce, educational institutions, and Government; provides advisory and research services to other Government agencies; develops, produces, and distributes Standard Reference Materials; and provides calibration services. The Laboratory consists of the following centers: Absolute Physical Quantities 2 — Radiation Research — Thermodynamics and Molecular Science — Analytical Chemistry — Materials Science.
    [Show full text]