DOCSLIB.ORG

Alcohol Ethoxylates

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Alcohol Ethoxylates Human & Environmental Risk Assessment on ingredients of European household cleaning products Alcohol Ethoxylates Version 2.0 September 2009 This version is based on the Version 1 (May 2007) where the equation 4.2 (page 24) has been corrected All rights reserved. No part of this publication may be used, reproduced, copied, stored or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the HERA Substance Team or the involved company. The content of this document has been prepared and reviewed by experts on behalf of HERA with all possible care and from the available scientific information. It is provided for information only . Much of the original underlying data which has helped to develop the risk assessment is in the ownership of individual companies. HERA cannot accept any responsibility or liability and does not provide a warranty for any use or interpretation of the material contained in this publication. 1 1. Executive summary General Alcohol ethoxylates (AE) are a major class of non-ionic surfactants which are widely used in laundry detergents and to a lesser extent in household cleaners, institutional and industrial cleaners, cosmetics, agriculture, and in textile, paper, oil and other process industries. Human health The presence of AE in household detergents gives rise to a variety of possible consumer contact scenarios including direct and indirect skin contact from its use in laundry detergents, inhalation through the use of spray cleaners and oral ingestion derived from residues deposited on dishes. The aggregate consumer exposure to AE has been conservatively estimated to be at maximum 6.48 µg/kg bw/day. A substantial amount of toxicological data and information in vivo and in vitro demonstrates that there is no evidence for AEs being genotoxic, mutagenic or carcinogenic. No adverse reproductive or developmental effects were observed. The majority of available toxicity studies revealed NOAELs in excess of 100 mg/kg bw/d but the lowest NOAEL for an individual AE was established to be 50 mg/kg bw/day. This value was subsequently considered as a conservative, representative value in the risk assessment of AE. The effects were restricted to changes in organ weights with no histopathological organ changes with the exception of liver hypertrophy (indicative of an adaptive response to metabolism rather than a toxic effect). It is noteworthy that there was practically no difference in the NOAEL in oral studies of 90-day or 2 years of duration in rats. A comparison of the aggregate consumer exposure and the systemic NOAEL (taking into account an oral absorption value of 75%) results in a Margin of Exposure of 5,800. Taking into account the conservatism in the exposure assessment and the assigned systemic NOAEL, this margin of exposure is considered more than adequate to account for the inherent uncertainty and variability of the hazard database and inter and intra-species extrapolations. AEs are not contact sensitizers. Neat AE are irritating to eyes and skin. The irritation potential of aqueous solutions of AEs depends on concentrations. Local dermal effects due to direct or indirect skin contact in certain use scenarios where the products are diluted are not of concern as AEs are not expected to be irritating to the skin at in-use concentrations. Potential irritation of the respiratory tract is not a concern given the very low levels of airborne AE generated as a consequence of spray cleaner aerosols or laundry powder detergent dust. In summary, the human health risk assessment has demonstrated that the use of AE in household laundry and cleaning detergents is safe and does not cause concern with regard to consumer use. Environment The environmental risk assessment uses the “sum of toxic units” approach, in which the ratio of the predicted environmental concentration (PEC) of each individual AE homologue to the predicted no effect concentration (PNEC) of that AE homologue is 2 first calculated, and then the sum of these ratios, or “toxic units”, is calculated for all AE homologues used in laundry cleaners and household cleaning products. Thus 230 different AE homologues, with hydrocarbon chain lengths from 8 to 18 and with ethylene oxide chain lengths from 0 to 22, are considered in the AE environmental risk assessment. The environmental concentrations in river water are determined from measured effluent concentrations from European sewage treatment facilities, using recently developed analytical methods able to measure environmental concentrations of individual AE homologues with hydrocarbon chain lengths from 12 to 18 and ethylene oxide chain lengths from 0 to 18. These homologues cover more than 80% of the tonnage used in laundry cleaners and household cleaning products. Conservative estimates have been made for the concentrations of the other AE homologues, and these are included in the risk assessment. The total local AE concentration in river water receiving sewage effluent (PEClocal dissolved ) is 1.01 µg/l. The equilibrium partitioning method has been used to predict the concentrations of the individual AE homologues in river sediment from the river water concentrations. Maximum values for soil concentrations have been estimated from measured concentrations of several representative European sewage sludges. The local sediment, soil, and sewage treatment plant concentrations have been determined as 1.01mg/kg wet sediment, 0.24 mg/kg wet soil, and 9.8 µg/l respectively, with the sewage treatment plant concentration determined from the measured AE effluent concentrations. Two complementary methods, both based on high quality chronic effects data, are used to determine the toxicity of the AE homologues in river water. The deterministic method uses a recently published QSAR for the species with the best high quality chronic information, Daphnia magna , with an application factor of 10. The probabilistic method uses a chronic QSAR, recently developed using data from 17 different species and an application factor of 1, to predict the NOEC values for each AE homologue. Equilibrium partitioning is then used to determine the toxicity of AE homologues in sediment and soil, with the soil values being supported by acute and chronic single homologue data for some AE homologues. Two risk assessments, one using the deterministic (D) method and one using the probabilistic method (P), have been carried out for the environmental concentrations of AE used in laundry cleaners and household cleaning products. The resulting risk assessment ratio (PEC/PNEC value) for all the AE homologues in surface water is 0.041 with the deterministic method (D), and 0.024 with the probabilistic method (P). Risk assessment ratios are 0.316(D) and 0.181(P) in sediment, 0.103(D) and 0.068(P) in soil, and 0.007 in the sewage treatment plant, where a simple method assuming the acute data for the most toxic AE mixture applies to all AE has been used. As all the risk assessment ratios are below 1, there is no cause for concern in any of the environmental compartments. In summary, AE usage in laundry cleaners and household cleaning products is not a cause for concern in the EU environment, as shown by consideration of surface water, sediment, sewage treatment facilities, and soil. 3 Table of contents 1. Executive summary....................................................................................................2 General.......................................................................................................................2 Human health.............................................................................................................2 Environment...............................................................................................................2 Table of contents............................................................................................................4 3. Substance characterisation.........................................................................................9 3.1 CAS number and grouping information ..............................................................9 3.2 Chemical structure and composition....................................................................9 3.2.1. Chemical Structure.......................................................................................9 3.2.2 Physicochemical Properties ........................................................................10 3.2.2.1. Solubility in water...............................................................................10 3.2.2.2. Melting point.......................................................................................13 3.2.2.3. Boiling Point .......................................................................................14 3.2.2.4. Vapour pressure data and Henry’s Law constant ...............................15 3.2.2.5. Log K ow , Koc , and K d information for AE homologues.......................16 3.3 Manufacturing route and production volume ....................................................18 3.4 Homologue distribution in HERA applications.................................................19 4. Environmental assessment.......................................................................................21 4.1. Environmental Exposure Assessment...............................................................21 4.1.1. Environmental Fate....................................................................................21
Load more

Recommended publications
  • 1.1 10 Oxidation of Alcohols and Aldehydes
    1.1 10 Oxidation of alcohols and aldehydes By the end of this spread, you should be able to … 1Describe the oxidation of primary alcohols to form aldehydes and carboxylic acids. 1Describe the oxidation of secondary alcohols to form ketones. 1Describe the oxidation of aldehydes to form carboxylic acids. Key definition Oxidation of alcohols You will recall from your AS chemistry studies that primary and secondary alcohols can A redox reaction is one in which both reduction and oxidation take place. be oxidised using an oxidising agent. s !SUITABLEOXIDISINGAGENTISASOLUTIONCONTAININGACIDIlEDDICHROMATEIONS + 2− H /Cr2O7 . s 4HEOXIDISINGMIXTURECANBEMADEFROMPOTASSIUMDICHROMATE +2Cr2O7, and sulfuric acid, H2SO. During the reaction, the acidified potassium dichromate changes from orange to green. Remember that tertiary alcohols are not oxidised by acidified dichromate ions. Primary alcohols Primary alcohols can be oxidised to aldehydes and to carboxylic acids (see AS Chemistry spread 2.2.3). H H H O H O Oxidation Oxidation H CCOH H CC H CC H H H H H OH Primary alcohol Aldehyde Carboxylic acid Figure 1 Ethanol oxidised to ethanal, and finally to ethanoic acid The equation for the oxidation of ethanol to the aldehyde ethanal is shown below. Note that the oxidising agent is shown as [O] – this simplifies the equation. CH3CH2OH + [O] }m CH3CHO + H2O When preparing aldehydes in the laboratory, you will need to distil the aldehyde from the reaction mixture as it is formed. This prevents the aldehyde from being oxidised further to a carboxylic acid. Key definition When making the carboxylic acid, the reaction mixture is usually heated under reflux before distilling the product off.
    [Show full text]
  • Enhancing the Efficacy of Antimicrobial Peptide BM2, Against Mono-Species Biofilms, with Detergents
    Enhancing the efficacy of Antimicrobial peptide BM2, against mono-species biofilms, by combining with detergents A thesis submitted for the degree of Doctor of Clinical Dentistry (Endodontics) Arpana Arthi Devi Department of Oral Rehabilitation, School of Dentistry, University of Otago, Dunedin, New Zealand 2016 Abstract Title Enhancing the efficacy of antimicrobial peptide BM2, against mono-species biofilms, by combining with detergents. Aim To investigate if a detergent regime could enhance the antimicrobial ability of BM2. Method Strains of Enterococcus faecalis, Streptococcus gordonii, Streptococcus mutans, and Candida albicans were grown from glycerol stocks after confirmation of the strains. After subculturing single colonies were cultured in TSB and CSM liquid media for 24hr to obtain a microbial suspension which was adjusted to OD600nm = 0.5. Dilution series of the peptidomimetic BM2 and detergents were prepared in aqueous solution and minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined using a broth micro-dilution method. Further on planktonic cells and monospecies biofilms were exposed to the detergent and BM2 combinations. The efficacy of BM2 and detergents at causing biofilm detachment was measured using a crystal violet based assay. Results Planktonic cells were easier to kill with some of the detergents in isolation or in combination with BM2. SDS and CTAB in combination with BM2 increased the efficacy of BM2 against the test organisms. Tween 20 did not kill any of the test organisms alone or in combination. Biofilms were harder to eradicate and detergent, BM2 combinations gave varied results for the different species tested. Detergents in combination with BM2 did not increase the efficacy of the antimicrobial peptide in disrupting S.
    [Show full text]
  • Ethoxylation Reactor Modelling and Design
    Ethoxylation Reactor Modelling and Design by Yen-ni Chiu Bachelor of Engineering (Chemical) UNSW A thesis submitted in fulfillment of the requirements for the degree of Doctor of Philosophy Facaulty of Engineering and Industrial Sciences Swinburne University of Technology Melbourne, Australia To Mum, Dad, Jess and Ted Abstract The manufacture of nonionic surfactants generally involves ethoxylation via ethylene oxide condensation onto a hydrophobe substrate, mostly in the presence of an alkaline catalyst. Nonionic surfactants are used widely in industrial applications, such as detergents, health and personal care, coatings, and polymers. In Australia, approximately one-third of the annual consumption of nonionic surfactants is imported from offshore manufacturers; the market is highly competitive with the local manufacturer facing increasing competition from imports. Optimisation is a pressing need for the current manufacturing plant of the industrial partner for this research project, Huntsman Corporation Australia Pty Limited, the sole domestic manufacturer of nonionic surfactants in Australia. Therefore, the objectives of this research project were • to gain a better understanding of the various chemical and physical processes occurring simultaneously in an ethoxylation process; • to identify the process limitation in an existing production plant operated by Huntsman Corporation Australia, and • to explore measures for enhancing the asset productivity of the production plant. An ethoxylation process working model, describing the chemical kinetics and the physical transport processes involved, was developed to aid the exploration of optimisation opportunities, which would otherwise be empirical. Accordingly, this research project was structured into a two-stage program. The first stage determined the ethoxylation kinetics experimentally. The second stage investigated the interactions of physical transport processes numerically using a computational fluid dynamics (CFD) technique.
    [Show full text]
  • Long Chain Alcohols (C6-22 Primary Aliphatic Alcohols)
    SIAM 22, 18-21 April 2006 UK/ICCA SIDS INITIAL ASSESSMENT PROFILE Chemical Category Name Long Chain Alcohols (C6-22 primary aliphatic alcohols) Chemical name CAS no. Chemical name CAS no. 1-Hexanol 111-27-3 Alcohols, C16-18 67762-27-0 1-Octanol 111-87-5 Alcohols, C14-18 67762-30-5 1-Decanol 112-30-1 Alcohols, C10-16 67762-41-8 1-Undecanol 112-42-5 Alcohols, C8-18 68551-07-5 1-Tridecanol 112-70-9 Alcohols, C14-16 68333-80-2 1-Tetradecanol 112-72-1 Alcohols, C6-12 68603-15-6 1-Pentadecanol 629-76-5 Alcohols, C12-16 68855-56-1 1-Hexadecanol 36653-82-4 Alcohols, C12-13 75782-86-4 CAS Nos 1-Eicosanol 629-96-9 Alcohols, C14-15 75782-87-5 1-Docosanol 661-19-8 Alcohols, C12-14 80206-82-2 Alcohols, C12-15 63393-82-8 Alcohols, C8-10 85566-12-7 Alcohols, C9-11 66455-17-2 Alcohols, C10-12 85665-26-5 Alcohols, C12-18 67762-25-8 Alcohols, C18-22 97552-91-5 9-Octadecen-1-ol 143-28-2 Alcohols, C14-18. 68155-00-0 (9Z)- & C16-18-unsatd Alcohols, C16-18 68002-94-8 Tridecanol, 90583-91-8 & C18 Unsaturated branched & linear Structural Formula CH3(CH2)nCH2OH Linear n = 4 to 20 CH3(CH2)nCHCH2OH 2-Alkyl branched n + m = 3 to 18, and m is predominantly (CH2)mCH3 = 0. Present in essentially-linear alcohols CH3(CH2)nCH(CH2)mOH Other-methyl branching n + m= 9 or 10 CH3 Present in essentially-linear Fischer- Tropsch derived alcohols CH3(CH2)7CH=CH(CH2)7CH2O Unsaturated H 9-Z unsaturated components are present in some commercial products.
    [Show full text]
  • United States Patent (19) 11 Patent Number: 6,013,801 Köll, Deceased Et Al
    US00601 3801A United States Patent (19) 11 Patent Number: 6,013,801 Köll, deceased et al. (45) Date of Patent: Jan. 11, 2000 54 METHOD FOR PRODUCING 4,590,223 5/1986 Arai et al. ........................... 544/401 X AMINOETHYLETHANOLAMINE AND/OR 5,455,352 10/1995 Huellmann et al. .................... 544/401 HYDROXYETHYL PPERAZINE FOREIGN PATENT DOCUMENTS 75 Inventors: Juhan Köll, deceased, late of Stenungsund, by Mall Koll, legal 0 354993 2/1990 European Pat. Off. ...... CO7C 213/06 representative; Magnus Frank, 2013 676 1/1972 Germany ....................... CO7D 51/64 Göteborg, both of Sweden 27 16946 10/1978 Germany ....................... CO7C 89/02 206670 2/1984 Germany. 73 Assignee: Akzo Nobel N.V., Arnhem, Netherlands 1512967 10/1989 Russian Federation ........ CO7C 91/12 21 Appl. No.: 08/875,871 OTHER PUBLICATIONS 22 PCT Filed: Jan. 11, 1996 86 PCT No.: PCT/EP96/00207 Ludwig Knorr und Henry W. Brownadon: Ueber Alkohol basen aus Aethylendiamin und uber das Aethylenbismor S371 Date: Oct. 30, 1998 pholin, Dec. 11, 1902 pp. 4470–4473. S 102(e) Date: Oct. 30, 1998 87 PCT Pub. No.: WO96/24576 Primary Examiner Michael G. Ambrose PCT Pub. Date: Aug. 15, 1996 Attorney, Agent, or Firm-Ralph J. Mancini 30 Foreign Application Priority Data 57 ABSTRACT Feb. 8, 1995 (SE) Sweden .................................. 9500444 A method for preparing aminoethylethanolamine, and/or hydroxyethylpiperazine is described. Reaction of ethylene 51) Int. Cl." ........................ C07D 295/88; CO7C 213/04 oxide with ethylendiamine, piperazine, or a mixture of both 52 U.S. Cl. ............................................. 544/401; 564/503 produces these compounds. The process is integrated into a 58 Field of Search .............................
    [Show full text]
  • Transcription 12.01.12
    Lecture 2B • 01/12/12 We covered three different reactions for converting alcohols into leaving groups. One was to turn an alcohol into an alkyl chloride, that was using thionyl chloride. Second reaction was using tosyl chloride; the primary difference between those two reactions is one of stereochemistry. An inversion of stereochemistry does occur if you use thionyl chloride, because it does affect the carbon-oxygen bond, but because forming a tosylate does not touch the carbon-oxygen bond, only the oxygen- hydrogen bond, there’s no change in stereochemistry there. We then saw phosphorus tribromide that reacts very similarly to the thionyl chloride; you get an alkyl bromide instead, but it also has inversion of configuration. The last reaction is not a new mechanism, it is just an Sn2 reaction, it’s called the Finkelstein reaction. Really this works, in a sense, off of Le Châtelier’s principle. In solution, in theory, sodium iodide can displace bromide, but sodium bromide can displace iodide, so you can have an Sn2 reaction that goes back and forth and back and forth and back and forth. Except, sodium iodide is somewhat soluble in acetone, while sodium chloride and sodium bromide are not. So, in fact, one of the things that we get out of this as a by-product is sodium bromide, which, again, is not soluble in acetone and therefore precipitates out and is no longer part of the reaction mixture, so there’s no reverse reaction possible. Because of this solubility trick, it allows this reaction to be pulled forward, which means you can get the alkyl iodide.
    [Show full text]
  • Fatty Acids: Fatty Acid Is a Carboxylic Acid Often with a Long Aliphatic Chain, Which Is Either Saturated Or Unsaturated
    Introduction 1 Fatty Acids: Fatty acid is a carboxylic acid often with a long aliphatic chain, which is either saturated or unsaturated. Fatty acids and their derivatives are consumed in a wide variety because they are used as raw materials for a wide variety of industrial products like, paints, surfactant, textiles, plastics, rubber, cosmetics, foods and pharmaceuticals. Industrially, fatty acids are produced by the hydrolysis of triglycerides, with the removal of glycerol moiety. As mentioned before, fatty acids can be classified into two classes, the first is unsaturated fatty acid with one or more double bonds in the alkyl chain and the other is saturated fatty acid. Long chain 3-alkenoic acids are a family of polyunsaturated fatty acids which have in common a carbon–carbon double bond in the position 3. They are used as key precursors for synthesis of many organic compounds. There are many methods for the synthesis of such acids; here we will mention two of these methods. Nucleophilic substitution of allylic substrates with organometallic reagents, treatment of β-vinyl-β-propiolactone with butylmagnesium bromide in the presence of copper(I) iodide in THF at –30 o C, gave 3-nonenoic acid as a major product and 3-butyl-4-pentenoic acid with the ratio 98:2 respectively(1). Knoevenagel condensation of an aldehyde with malonic acid in the presence of organic bases was considerable value for the synthesis of unsaturated fatty acids. This reaction is mainly related to its application for the synthesis of α-β-unsaturated fatty acids. For the synthesis of β-γ-unsaturated fatty acids the Linstead modification (2) of the Knoevenagel condensation, in which triethanolamine or other tertiary amines are used.
    [Show full text]
  • Predicting Distribution of Ethoxylation Homologues With
    1 PREDICTING THE DISTRIBUTION OF ETHOXYLATION HOMOLOGUES WITH A PROCESS SIMULATOR Nathan Massey, Chemstations, Inc. Introduction Ethoxylates are generally obtained by additions of ethylene oxide (EO) to compounds containing dissociated protons. Substrates used for ethoxylation are primarily linear and branched C12-C18 alcohols, alkyl phenols, nonyl (propylene trimer) or decyl (propylene tetramer) groups, fatty acids and fatty acid derivatives. The addition of EO to a substrate containing acidic hydrogen is catalyzed by bases or Lewis acids. Amphoteric catalysts, as well as heterogeneous catalysts are also used. The degree of ethoxylation ( the moles of EO added per mole of substrate ) varies over wide ranges, in general between 3 and 40, and is chosen according to the intended use. As an illustration of how this distribution might be predicted using a process simulator, Chemcad was used to simulate the ethoxylation of Nonylphenols. Description of the Ethoxylation Chemistry The reaction mechanisms of base catalyzed and acid catalyzed ethoxylation differ, which affects the composition of the reaction products. In base catalyzed ethoxylation an alcoholate anion, formed initially by reaction with the catalyst ( alkali metal, alkali metal oxide, carbonate, hydroxide, or alkoxide ) nucleophilically attacks EO. The resulting union of the EO addition product can undergo an equilibrium reaction with the alcohol starting material or ethoxylated product, or can react further with EO: Figure 1 O RO- + H2CCH2 - - RO CH2CH2O O ROH H2CCH2 - - RO RO CH2CH2OH RO RO CH2CH2O 2 As Figure 1 illustrates, in alkaline catalyzed ethoxylations several reactions proceed in parallel. The addition of EO to an anion with the formation of an ether bond is irreversible.
    [Show full text]
  • Reactions of Alcohols & Ethers 1
    REACTIONS OF ALCOHOLS & ETHERS 1. Combustion (Extreme Oxidation) alcohol + oxygen carbon dioxide + water 2 CH3CH2OH + 6 O2 4 CO2 + 6 H2O 2. Elimination (Dehydration) ° alcohol H 2 S O 4/ 1 0 0 C alkene + water H2SO4/100 ° C CH3CH2CH2OH CH3CH=CH2 + H2O 3. Condensation ° excess alcohol H 2 S O 4 / 1 4 0 C ether + water H2SO4/140 ° C 2 CH3CH2OH CH3CH2OCH2CH3 + H2O 4. Substitution Lucas Reagent alcohol + hydrogen halide Z n C l2 alkyl halide + water ZnCl2 CH3CH2OH + HCl CH3CH2Cl + H2O • This reaction with the Lucas Reagent (ZnCl2) is a qualitative test for the different types of alcohols because the rate of the reaction differs greatly for a primary, secondary and tertiary alcohol. • The difference in rates is due to the solubility of the resulting alkyl halides • Tertiary Alcohol→ turns cloudy immediately (the alkyl halide is not soluble in water and precipitates out) • Secondary Alcohol → turns cloudy after 5 minutes • Primary Alcohol → takes much longer than 5 minutes to turn cloudy 5. Oxidation • Uses an oxidizing agent such as potassium permanganate (KMnO4) or potassium dichromate (K2Cr2O7). • This reaction can also be used as a qualitative test for the different types of alcohols because there is a distinct colour change. dichromate → chromium 3+ (orange) → (green) permanganate → manganese (IV) oxide (purple) → (brown) Tertiary Alcohol not oxidized under normal conditions CH3 KMnO4 H3C C OH NO REACTION K2Cr2O7 CH3 tertbutyl alcohol Secondary Alcohol ketone + hydrogen ions H O KMnO4 H3C C CH3 + K2Cr2O7 C + 2 H H3C CH3 OH propanone 2-propanol Primary Alcohol aldehyde + water carboxylic acid + hydrogen ions O KMnO4 O H H KMnO H H 4 + CH3CH2CH2OH C C C H C C C H + 2 H K2Cr2O7 + H2O K Cr O H H H 2 2 7 HO H H 1-propanol propanal propanoic acid 6.
    [Show full text]
  • Chapter 18 Ethers and Epoxides; Thiols and Sulfides Ethers
    Chapter 18 Ethers and Epoxides; Thiols and Sulfides Ethers • Ethers (R–O–R’): – Organic derivatives of water, having two organic groups bonded to the same oxygen atom © 2016 Cengage Learning 2 NAMES AND PROPERTIES OF ETHERS 3 Nomenclature: Common Names • Simple ethers are named by identifying two organic substituents and adding the word ether – Name the groups in alphabetical order – Symmetrical: Use dialkyl or just alkyl © 2016 Cengage Learning 4 Nomenclature: IUPAC Names • The more complex alkyl group is the parent name • The group with the oxygen becomes an alkoxy group © 2016 Cengage Learning 5 Nomenclature: Cyclic Ethers (Heterocycles) • Heterocyclic: Oxygen is part of the ring. O • Epoxides (oxiranes) H2C CH2 O • Oxetanes • Furans (Oxolanes) O O • Pyrans (Oxanes) O O O • Dioxanes O © 2013 Pearson Education, Inc. 6 Epoxide Nomenclature • Name the starting alkene and add “oxide” © 2013 Pearson Education, Inc. 7 Epoxide Nomenclature • The oxygen can be treated as a substituent (epoxy) on the compound • Use numbers to specify position • Oxygen is 1, the carbons are 2 and 3 • Substituents are named in alphabetical order © 2013 Pearson Education, Inc. 8 Properties of Ethers • Possess nearly the same geometry as water – Oxygen atom is sp3-hybridized – Bond angles of R–O–R bonds are approximately tetrahedral • Polar C—O bonds © 2013 Pearson Education, Inc. 9 Properties of Ethers: Hydrogen Bond • Hydrogen bond is a attractive interaction between an electronegative atom and a hydrogen atom bonded to another electronegative atom • Ethers cannot hydrogen bond with other ether molecules, so they have a lower boiling point than alcohols • Ether molecules can hydrogen bond with water and alcohol molecules • They are hydrogen bond acceptors © 2013 Pearson Education, Inc.
    [Show full text]
  • Linear Alpha-Olefins (681.5030)
    IHS Chemical Chemical Economics Handbook Linear alpha-Olefins (681.5030) by Elvira O. Camara Greiner with Yoshio Inoguchi Sample Report from 2010 November 2010 ihs.com/chemical November 2010 LINEAR ALPHA-OLEFINS Olefins 681.5030 B Page 2 The information provided in this publication has been obtained from a variety of sources which SRI Consulting believes to be reliable. SRI Consulting makes no warranties as to the accuracy completeness or correctness of the information in this publication. Consequently SRI Consulting will not be liable for any technical inaccuracies typographical errors or omissions contained in this publication. This publication is provided without warranties of any kind either express or implied including but not limited to implied warranties of merchantability fitness for a particular purpose or non-infringement. IN NO EVENT WILL SRI CONSULTING BE LIABLE FOR ANY INCIDENTAL CONSEQUENTIAL OR INDIRECT DAMAGES (INCLUDING BUT NOT LIMITED TO DAMAGES FOR LOSS OF PROFITS BUSINESS INTERRUPTION OR THE LIKE) ARISING OUT OF THE USE OF THIS PUBLICATION EVEN IF IT WAS NOTIFIED ABOUT THE POSSIBILITY OF SUCH DAMAGES. BECAUSE SOME STATES DO NOT ALLOW THE EXCLUSION OR LIMITATION OF LIABILITY FOR CONSEQUENTIAL OR INCIDENTAL DAMAGES THE ABOVE LIMITATION MAY NOT APPLY TO YOU. IN SUCH STATES SRI CONSULTING’S LIABILITY IS LIMITED TO THE MAXIMUM EXTENT PERMITTED BY SUCH LAW. Certain statements in this publication are projections or other forward-looking statements. Any such statements contained herein are based upon SRI Consulting’s current knowledge and assumptions about future events including without limitation anticipated levels of global demand and supply expected costs trade patterns and general economic political and marketing conditions.
    [Show full text]
  • Soln-2212-PT3-S20-Ch-16-18.Pdf
    1. 2. H2SO4 H2SO4 H2SO41) BH3, THF 1) BH3, THF 1) BH3, THF - - - 2) OH , H2O2, H2O2) OH , H2O2, H2O 2) OH , H2O2, H2O OH OH OH 3. OH OH OH H2SO4 1) BH3, THF - 2) OH , H2O2, H2O OH PBr3 PBr3 PBr3 Pyridine Pyridine Pyridine OH PBr3 Pyridine O O O Mg Mg Mg HO HO HO1) 1) 1) Ether Ether Ether 2) HCl 2) HCl 2) HCl Br Br Br MgBr MgBr MgBr O Mg HO 1) Ether 2) HCl Br 4. MgBr **This reaction reduces an aldehyde to a primary alcohol and a ketone to a secondary alcohol. Since only one EQ of reagent is given the most reactive functional group will be reduced (in this case the aldehyde) **ketones are less reactive than aldehydes and the more steric hindrance surrounding the ketone the less reactive it is. Note: NaBH4 reduces ketones but is too weak to reduce an ester/double/triple bonds 5. ** With these reagents a tertiary amide will be reduced to a tertiary amine, a secondary amide will be reduced to a secondary amine, and a primary amide will be reduced to a primary amine 6. ** Recall from chapter 7, OChem 1 H2 and Lindlars catalyst always reduces an alkyne to a CIS ALKENE ** Li/Na and liquid NH3 always reduces an alkyne to a TRANS ALKENE 7. **A ketone/aldehyde reacts with primary amines in trace acid to produce an imine, and reacts with a secondary amine in trace acid to produce an enamine (double bond forms between the alpha and beta carbons) **Sodium cyanoborohydride (NaBH3CN) is used to reduce imines/enamines back to their respective secondary/tertiary amines 8.
    [Show full text]