Experiment 7 – Aldehydes, Ketones, and Carboxylic Acids
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Methyl Ethyl Ketone (2-Butanone)
Methyl Ethyl Ketone (2-Butanone) 78-93-3 Hazard Summary Methyl ethyl ketone is used as a solvent. Acute (short-term) inhalation exposure to methyl ethyl ketone in humans results in irritation to the eyes, nose, and throat. Limited information is available on the chronic (long-term) effects of methyl ethyl ketone in humans. Chronic inhalation studies in animals have reported slight neurological, liver, kidney, and respiratory effects. No information is available on the developmental, reproductive, or carcinogenic effects of methyl ethyl ketone in humans. Developmental effects, including decreased fetal weight and fetal malformations, have been reported in mice and rats exposed to methyl ethyl ketone via inhalation and ingestion. EPA has classified methyl ethyl ketone as a Group D, not classifiable as to human carcinogenicity. Please Note: The main sources of information for this fact sheet are EPA's Health Effects Assessment for Methyl Ethyl Ketone (1) and EPA's Integrated Risk Information System (IRIS) (6), which contains information on inhalation chronic toxicity of methyl ethyl ketone and the RfC and oral chronic toxicity and the RfD. Uses The primary use of methyl ethyl ketone is as a solvent in processes involving gums, resins, cellulose acetate, and cellulose nitrate. (1) Methyl ethyl ketone is also used in the synthetic rubber industry, in the production of paraffin wax, and in household products such as lacquer and varnishes, paint remover, and glues. (1) Sources and Potential Exposure Methyl ethyl ketone has been detected in both indoor and outdoor air. Methyl ethyl ketone can be produced in outdoor air by the photooxidation of certain air pollutants, such as butane and other hydrocarbons. -
Direct Β‑Functionalization of Cyclic Ketones with Aryl Ketones Via the Merger of Photoredox and Organocatalysis Filip R
Communication pubs.acs.org/JACS Direct β‑Functionalization of Cyclic Ketones with Aryl Ketones via the Merger of Photoredox and Organocatalysis Filip R. Petronijevic,́† Manuel Nappi,† and David W. C. MacMillan* Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States *S Supporting Information ABSTRACT: The direct β-coupling of cyclic ketones with aryl ketones has been achieved via the synergistic combination of photoredox catalysis and organocatalysis. Diaryl oxymethyl or aryl−alkyl oxymethyl radicals, transiently generated via single-electron reduction of ketone precursors, readily merge with β-enaminyl radical species, generated by photon-induced enamine oxidation, to produce γ-hydroxyketone adducts. Experimental evidence indicates that two discrete reaction pathways can be operable in this process depending upon the nature of the ketyl radical precursor and the photocatalyst. he direct β-functionalization of saturated ketones and T aldehydes is an important yet elusive goal in organic chemistry.1 While carbonyl groups are readily amenable to ipso- and α-carbon substitution with a range of nucleophiles and electrophiles respectively,2,3 activation at the β-methylene position poses a significant synthetic challenge. With a few notable exceptions,1,4 carbonyl β-functionalization has tradition- ally been restricted to the conjugate addition of soft nucleophiles are accessed via carbene catalysis,9,10 nucleophilic addition of into α,β-unsaturated carbonyl systems. As such, the development acetal-protected Grignard reagents,11 or stoichiometric metal- 5 − of a general catalytic platform for the direct β-functionalization activated homoenolate equivalents.12 16 of saturated ketones or aldehydes would represent a conceptual Drawing from the mechanistic insights gained in the course of and practical advance for the field. -
Methyl Isopropyl Ketone Safety Data Sheet According to Federal Register / Vol
Methyl isopropyl ketone Safety Data Sheet according to Federal Register / Vol. 77, No. 58 / Monday, March 26, 2012 / Rules and Regulations Date of issue: 05/25/2015 Version: 1.0 SECTION 1: Identification 1.1. Identification Product form : Substance Substance name : Methyl isopropyl ketone CAS-No. : 563-80-4 Product code : (US) W1814 Formula : C5H10O Synonyms : 3-Methylbutane-2-one / Isopropyl methyl ketone / Methyl-2-butanone, 3- / 2-Acetylpropane / 3- Methylbutanone-2 / 3-Methylbutanone / 3-Methylbutan-2-one / 3-Methyl-2-butanone / 2- Butanone, 3-methyl- / Butan-2-one, 3-methyl- 1.2. Recommended use and restrictions on use No additional information available 1.3. S upplie r Synerzine 5340 Hwy 42 S Ellenwood, Georgia 30294 - USA T 404-524-6744 - F 404-577-1651 [email protected] - www.synerzine.com 1.4. Emergency telephone number Emergency number : Infotrac 1-800-535-5053 (Contract# 102471) Dial +1-352-323-3500 when outside the US SECTION 2: Hazard(s) identification 2.1. Classification of the substance or mi xt ure GHS -US classification Flammable liquids Category H225 Highly flammable liquid and vapour 2 Specific target organ toxicity H336 May cause drowsiness or dizziness (single exposure) Category 3 Hazardous to the aquatic H402 Harmful to aquatic life environment - Acute Hazard Category 3 Full text of H statements : see section 16 2.2. GHS Label elements, including precautionary statements GHS-US labeling Hazard pictograms (GHS-US) : Signal word (GHS-US) : Danger Hazard statements (GHS-US) : H225 - Highly flammable liquid and vapour H336 - May cause drowsiness or dizziness H402 - Harmful to aquatic life Precautionary statements (GHS-US) : P210 - Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. -
Toxicological Profile for 2-Butanone Released for Public Comment in May 2019
Toxicological Profile for 2-Butanone October 2020 2-BUTANONE 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. 2-BUTANONE 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. The adequacy of information to determine a substance's -
Aldehydes and Ketones
12 Aldehydes and Ketones Ethanol from alcoholic beverages is first metabolized to acetaldehyde before being broken down further in the body. The reactivity of the carbonyl group of acetaldehyde allows it to bind to proteins in the body, the products of which lead to tissue damage and organ disease. Inset: A model of acetaldehyde. (Novastock/ Stock Connection/Glow Images) KEY QUESTIONS 12.1 What Are Aldehydes and Ketones? 12.8 What Is Keto–Enol Tautomerism? 12.2 How Are Aldehydes and Ketones Named? 12.9 How Are Aldehydes and Ketones Oxidized? 12.3 What Are the Physical Properties of Aldehydes 12.10 How Are Aldehydes and Ketones Reduced? and Ketones? 12.4 What Is the Most Common Reaction Theme of HOW TO Aldehydes and Ketones? 12.1 How to Predict the Product of a Grignard Reaction 12.5 What Are Grignard Reagents, and How Do They 12.2 How to Determine the Reactants Used to React with Aldehydes and Ketones? Synthesize a Hemiacetal or Acetal 12.6 What Are Hemiacetals and Acetals? 12.7 How Do Aldehydes and Ketones React with CHEMICAL CONNECTIONS Ammonia and Amines? 12A A Green Synthesis of Adipic Acid IN THIS AND several of the following chapters, we study the physical and chemical properties of compounds containing the carbonyl group, C O. Because this group is the functional group of aldehydes, ketones, and carboxylic acids and their derivatives, it is one of the most important functional groups in organic chemistry and in the chemistry of biological systems. The chemical properties of the carbonyl group are straightforward, and an understanding of its characteristic reaction themes leads very quickly to an understanding of a wide variety of organic reactions. -
References on Use of CO2 for Medical
Some References on the Use of CO2 for Medical Entomology Survey Becker N et al. Comparison of carbon dioxide, octenol and a host-odour as mosquito attractants in the Upper Rhine Valley, Germany. Med Vet Entomol 1995;9:377-80. Abstract: Field studies were conducted in the Upper Rhine Valley to determine the responses of mosquitoes to CDC traps baited with either CO2, octenol, light or paired combinations of these. Among eight mosquito species caught, the attractant effect on trap catches was studied in the four most abundant: Aedes vexans, Ae. rossicus, Ae. cinereus and Culex pipiens. Traps baited only with light or octenol caught few mosquitoes, whereas many were caught by traps baited with CO2 alone or in combination with either of the other candidate attractants. CO2 baited traps, with or without light, caught the most Aedes. The combination of CO2 and octenol attracted most Cx pipiens, but this apparent synergy was not significant. Using a caged hamster compared to CO2 as bait in a CDC light-trap with only intermittent fan suction, the hamster attracted less mosquitoes than CO2 emitted at a rate of 225 g/h on days 1 and 2, whereas on days 3 and 4 the smell from the hamster's cage became significantly more attractive than this rate of CO2 for all species of mosquitoes. Canyon DV, Hii JL. Efficacy of carbon dioxide, 1-octen-3-ol, and lactic acid in modified Fay- Prince traps as compared to man-landing catch of Aedes aegypti. J Am Mosq Control Assoc 1997;13:66-70. Abstract: The attractants 1-octen-3-ol and lactic acid significantly decreased catches of Aedes aegypti in Townsville, Australia, by 50% in a controlled laboratory environment and by 100% in the field when compared to carbon dioxide baited bidirectional Fay-Prince trap catches. -
EPA Method 8315A (SW-846): Determination of Carbonyl Compounds by High Performance Liquid Chromatography (HPLC)
METHOD 8315A DETERMINATION OF CARBONYL COMPOUNDS BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC) 1.0 SCOPE AND APPLICATION 1.1 This method provides procedures for the determination of free carbonyl compounds in various matrices by derivatization with 2,4-dinitrophenylhydrazine (DNPH). The method utilizes high performance liquid chromatography (HPLC) with ultraviolet/visible (UV/vis) detection to identify and quantitate the target analytes. This method includes two procedures encompassing all aspects of the analysis (extraction to determination of concentration). Procedure 1 is appropriate for the analysis of aqueous, soil and waste samples and stack samples collected by Method 0011. Procedure 2 is appropriate for the analysis of indoor air samples collected by Method 0100. The list of target analytes differs by procedure. The appropriate procedure for each target analyte is listed in the table below. Compound CAS No. a Proc. 1b Proc. 2 b Acetaldehyde 75-07-0 X X Acetone 67-64-1 X Acrolein 107-02-8 X Benzaldehyde 100-52-7 X Butanal (Butyraldehyde) 123-72-8 X X Crotonaldehyde 123-73-9 X X Cyclohexanone 108-94-1 X Decanal 112-31-2 X 2,5-Dimethylbenzaldehyde 5779-94-2 X Formaldehyde 50-00-0 X X Heptanal 111-71-7 X Hexanal (Hexaldehyde) 66-25-1 X X Isovaleraldehyde 590-86-3 X Nonanal 124-19-6 X Octanal 124-13-0 X Pentanal (Valeraldehyde) 110-62-3 X X Propanal (Propionaldehyde) 123-38-6 X X m-Tolualdehyde 620-23-5 X X o-Tolualdehyde 529-20-4 X p-Tolualdehyde 104-87-0 X a Chemical Abstract Service Registry Number. -
Aldehydes and Ketone
ALDEHYDES AND KETONE www.gneet.com ALDEHYDES AND KETONES In aldehydes, the carbonyl group is linked to either two hydrogen atom or one hydrogen atom and one carbon containing group such as alkyl, aryl or aralkyl group Examples * In ketones, the carbonyl group is linked to two carbon containing groups which may be same or different alkyl, aryl group. If two R and R’ groups are same, the ketone is called simple or symmetrical ketone and if R and R’ are different, then ketone is known as mixed or an unsymmetrical ketone. STRUCTURE Carbonyl carbon of both aldehyde and ketones is sp2 – hybridised, One of the three sp2 hybridised orbital get involved in σ- bond formation with half –filled p-orbital of oxygen atom whereas rest of the two are consumed in σ-bond formation with hydrogen and carbon depending on the structure of aldehyde or ketone. Unhybridised p-orbital of carbonyl carbon form π-bond with another half-filled p-orbital of oxygen atom by sideways overlapping. ISOMERISM IN ALDEHYDES AND KETONES (a) Chain isomerism: Aldehydes ( with 4 or more carbon atoms) and ketone ( with 5 or more carbon atoms) show chain isomerism. Example i) C4H8O CH3-CH2-CH2-CHO ( butanal) 1 ALDEHYDES AND KETONE www.gneet.com ii) C5H10O (b) Position isomerism: aliphatic aldehydes do not show position isomerism, because –CHO group is always present at the end of carbon chain. Aromatic aldehyde show position isomerism. Example (c) Metamerism: Higher ketones show metamerism due to presence of different alkyl groups attached to the same functional group C5H10O (d) Functional isomerism : Aldehydes and ketones show functional isomerism in them. -
Toxicological Profile for Formaldehyde
TOXICOLOGICAL PROFILE FOR FORMALDEHYDE U.S. DEPARTMENT OF HEALTH AND HUMAN SERVICES Public Health Service Agency for Toxic Substances and Disease Registry July 1999 FORMALDEHYDE ii DISCLAIMER The use of company or product name(s) is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry. FORMALDEHYDE iii UPDATE STATEMENT Toxicological profiles are revised and republished as necessary, but no less than once every three years. For information regarding the update status of previously released profiles, contact ATSDR at: Agency for Toxic Substances and Disease Registry Division of Toxicology/Toxicology Information Branch 1600 Clifton Road NE, E-29 Atlanta, Georgia 30333 FORMALDEHYDE vii QUICK REFERENCE FOR HEALTH CARE PROVIDERS Toxicological Profiles are a unique compilation of toxicological information on a given hazardous substance. Each profile reflects a comprehensive and extensive evaluation, summary, and interpretation of available toxicologic and epidemiologic information on a substance. Health care providers treating patients potentially exposed to hazardous substances will find the following information helpful for fast answers to often-asked questions. Primary Chapters/Sections of Interest Chapter 1: Public Health Statement: The Public Health Statement can be a useful tool for educating patients about possible exposure to a hazardous substance. It explains a substance’s relevant toxicologic properties in a nontechnical, question-and-answer format, and it includes a review of the general health effects observed following exposure. Chapter 2: Health Effects: Specific health effects of a given hazardous compound are reported by route of exposure, by type of health effect (death, systemic, immunologic, reproductive), and by length of exposure (acute, intermediate, and chronic). -
Influence of Impurities in a Methanol Solvent on the Epoxidation of Propylene with Hydrogen Peroxide Over Titanium Silicalite‐1
Supplementary Materials Influence of Impurities in a Methanol Solvent on the Epoxidation of Propylene with Hydrogen Peroxide over Titanium Silicalite‐1 Gang Wang, Yue Li, Quanren Zhu, Gang Li, Chao Zhang, and Hongchen Guo* State Key Laboratory of Fine Chemicals and School of Chemical Engineering, Dalian University of Technology, No. 2 Linggong Road, Dalian 116024, PR China; [email protected] (G.W.); [email protected] (Y.L.); [email protected] (Q.Z.); [email protected] (G.L.); [email protected] (C.Z.) * Correspondence: [email protected]; Tel./Fax: +86‐411‐84986120 Received: 23 November 2019; Accepted: 18 December 2019; Published: date Table S1. Influence of fusel alcohol content on the product distribution and turnover numbers in epoxidation of propylene with H2O2a Conten Selectivity, % Impurity TONb t, wt.% 1M2Pc 2M1Pc PGc DGMEc PGMEc AAc PAc ATc noned 0.00 314.5 0.50 0.52 0.17 0.08 0.00 0.23 0.06 0.00 ethanol 1.00 296.8 0.48 0.46 0.17 0.06 0.01 0.22 0.06 0.00 1.50 286.8 0.45 0.45 0.15 0.05 0.02 0.26 0.06 0.01 2.00 282.9 0.38 0.42 0.14 0.04 0.02 0.28 0.07 0.01 2.50 267.9 0.38 0.41 0.14 0.03 0.03 0.29 0.07 0.01 2‐propanol 0.50 296.8 0.45 0.49 0.17 0.06 0.00 0.21 0.07 0.03 0.75 286.8 0.43 0.47 0.15 0.06 0.00 0.22 0.07 0.05 1.00 282.9 0.41 0.47 0.15 0.04 0.00 0.25 0.08 0.07 1.25 267.9 0.37 0.38 0.14 0.03 0.00 0.26 0.09 0.08 1‐propanol 0.50 297.7 0.51 0.55 0.18 0.06 0.00 0.21 0.11 0.00 0.75 289.0 0.45 0.49 0.18 0.05 0.00 0.22 0.11 0.00 1.00 282.5 0.44 0.49 0.17 0.05 0.00 0.24 0.14 0.01 1.25 266.0 0.43 0.48 0.16 0.05 0.00 0.26 0.14 0.01 Note: a Reaction conditions: pre‐adsorbed TS‐1 powder 0.4 g, fresh methanol or simulated methanol solvents containing ethanol, 2‐propanol and 1‐propanol 35.5 mL, H2O2 (50 wt.%) 4.5 mL, NH3∙H2O (0.32 mol/L) 0.2 mL, propylene pressure 0.6 MPa, 50 ℃, 1 h. -
Dose–Response Assay for Synthetic Mosquito (Diptera: Culicidae) Attractant Using a High-Throughput Screening System
insects Article Dose–Response Assay for Synthetic Mosquito (Diptera: Culicidae) Attractant Using a High-Throughput Screening System Dae-Yun Kim 1, Theerachart Leepasert 2, Michael J. Bangs 1 and Theeraphap Chareonviriyaphap 1,* 1 Department of Entomology, Faculty of Agriculture, Kasetsart Univeristy, Bangkok 10900, Thailand; [email protected] (D.-Y.K.); [email protected] (M.J.B.) 2 Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand; [email protected] * Correspondence: [email protected] Simple Summary: Entomological surveillance is important to evaluate vector management inter- ventions. However, collecting adult mosquitoes using direct human bait is controversial and often discouraged because of potential infection risk. Alternatively, active and passive trapping methods are available. Female mosquitoes detect human host cues such as body heat, carbon dioxide, and other volatile body emanations using olfactory sensilla to direct movement to a host. Attractive chemical lures have been identified and evaluated using a variety of olfactometric methods to in- crease trap production and efficiency. In this study, we evaluated a simple olfactometer without need of airflow. To ‘optimize’ a commercial mosquito attractant, 10 different doses of product, the TM Biogents-lure (BG-lure ), were compared. Results showed dose-dependent responses with 0.005 g with the highest attraction for Aedes aegypti, while doses of 0.2 g and above produced a repellent Citation: Kim, D.-Y.; Leepasert, T.; response. There was no significantly different response behavior between permethrin-susceptible Bangs, M.J.; Chareonviriyaphap, T. and -resistant Ae. aegypti. Culex quinquefasciatus showed significantly different responses compared Dose–Response Assay for Synthetic to Ae. -
Propionaldehyde Pad
PROPIONALDEHYDE PAD CAUTIONARY RESPONSE INFORMATION 4. FIRE HAZARDS 7. SHIPPING INFORMATION 4.1 Flash Point: 7.1 Grades of Purity: 97-99+% Common Synonyms Liquid Colorless Suffocating, –22°F O.C. 7.2 Storage Temperature: Ambient Methyl acetaldehyde unpleasant odor 4.2 Flammable Limits in Air: 2.6%-16.1% Propanal 7.3 Inert Atmosphere: No requirement 4.3 Fire Extinguishing Agents: Carbon Propionic aldehyde 7.4 Venting: Open (flame arrester) or pressure- dioxide or dry chemical for small fires, Propyl aldehyde Floats and mixes slowly with water. Flammable, irritating vapor is vacuum Propylic aldehyde produced. alcohol-type foam for large fires. 4.4 Fire Extinguishing Agents Not to Be 7.5 IMO Pollution Category: C Used: Water may be ineffective. 7.6 Ship Type: 3 Keep people away. Avoid contact with liquid and vapor. Wear goggles, self-contained breathing apparatus, and rubber overclothing 4.5 Special Hazards of Combustion 7.7 Barge Hull Type: Currently not available (including gloves). Products: Not pertinent Shut off ignition sources and call fire department. 4.6 Behavior in Fire: Vapor is heavier than 8. HAZARD CLASSIFICATIONS Stay upwind and use water spray to ``knock down'' vapor. air and may travel considerable distance Notify local health and pollution control agencies. to a source of ignition and flash back. 8.1 49 CFR Category: Flammable liquid Protect water intakes. 4.7 Auto Ignition Temperature: 405°F 8.2 49 CFR Class: 3 4.8 Electrical Hazards: Not pertinent 8.3 49 CFR Package Group: II FLAMMABLE. Fire Flashback along vapor trail may occur. 4.9 Burning Rate: 4.4 mm/min.