DOCSLIB.ORG

CXXVI.-Y%C Fiycld)~-Omicles of Undecylenic Acid

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
CXXVI.-Y%C Fiycld)~-Omicles of Undecylenic Acid View Article Online / Journal Homepage / Table of Contents for this issue THE IIY DROBROMIDES OF UNDECYLENIC ACID. 1191 CXXVI.-Y%c fIycld)~-omiclesof Undecylenic Acid. By JAMES WALKERand JOHNs. LUMSDEN. BRUNNER(Bey-., 1886, 18, 2226), by the addition of hydrogen bromide to undecylenic acid, CI,H,,02, obtained a bromundecylic acid, C,,H,,O,Br, which fused at 35’. No details of the mode of preparation or purification are given. The same acid is mentioned by Nordlinger (Ber., 1890, 23, 2357), but again no details are given. Nardlinger also, by the addition of hydrogen bromide to the methyl and ethyl esters of undecylenic acid, prepared the corresponding esters of a bromundecylic acid, As it has been proved with practical certainty that ufidecylenic acid has the formula CH,:CH*[CH,],*CO,H, compounds obtained from it by the addition of hydrogen bromide must have one or other of the formula : CH,Br*CH,*[CH,],*CO,H and CH,*C€€Br*[CH,~,*CO2H. Nordlinger, on the strength of the rule that the halogen atom in such additions generally takes up the position more remote from the Published on 01 January 1901. Downloaded by Fudan University 23/11/2017 08:36:04. carboxyl group, assumes that Brunner’s acid has the formula CH,Br*[CH,]9*C0,H and that the esters which he himself prepared are the esters of this acid. Since these esters have been made the starting point for determining the constitution of various substances, it is plainly of importance to know if Nordlinger’s assumptions are justified, In the present paper, it is shown that the acid CH,Br*[CH,],*CO,H is not Brunner’s acid, which has in all probability the other con- stitution, C?H,*CHBr*[CH,],*CO,H. Both these acids are simul- taneously formed by the addition of hydrogen bromide to undecylenic acid, and no doubt the esters of both are produced by the addition of hydrogen bromide to undecylenic esters, a circumstance which would explain the divergent results obtained by different observers in syntheses involving their use. View Article Online 1192 WALKER AND LUMSDEN: Addition of Hydrogen Bromide to Undecplenic Acid. The hydrogen bromide which we used in the following experiments was in all cases free from bromine, and dried by means of phosphoric oxide. Addition without the use of a Solvent.-The following is a typical experiment. Seven grams of undecylenic acid were saturated with hydrogen bromide at the ordinary temperature. The acid fused and became slightly warm. Absorption ceased when 35 grams of the gas had been taken up. Dry air was then led through the liquid product to remove the excess of hydrogen bromide. This occasioned a loss of 0.5 gram, so that 7 grams of undecylenic acid had united with 3.0 grams of hydrogen bromide, the calculated quantity being 3.1 grams. After remaining for some time in a vacuous desiccator, the liquid partially solidified, and the crystals (4 grams) were separated from the oil (6 grams) by filtration. The crude crystals were spread on porous tiles to remove the oil which still adhered to them, and were recrystallised from warm light petroleum. The substance separated in clusters of needles which melted at 50°. The oil did not solidify at the laboratory temperature even after long-continued standing, but crystallised on cooling to Oo. The crys- tals were washed on the ice-cooled filter with cooled light petroleum, and were then spread on porous tiles. On recrystallisation from light petroleum, they melted at 359 In this experiment, Brunner's acid mas formed in about equal propor- tion with another acid of higher melting point, The proportions of Published on 01 January 1901. Downloaded by Fudan University 23/11/2017 08:36:04. the two acids vary very much in different experiments-, sometimes one, sometimes the other, preponderating. Addition in Ethereal Xolut iom-Seven grams of undecylenic acid were dissolved in anhydrous ether, and the solution saturated at the ordinary temperature with hydrogen bromide, the excess of which was after- wards removed by a current of dry air. On evaporation of the ether, the residue solidified, and was purified by spreading on a porous tile and recrystallisation from light petroleum. Five grams of Brunner's acid melting at 35' were thus obtained. Tbe presence of the ether seems to favour the formation of the isomeride of lower melting point. Addition in, Toluene Solution.-Twenty-five grams of undecylenic acid were dissolved in 20 grams of toluene, the solution cooled in ice, and saturated with hydrogen bromide. When saturation was com- plete, a solid separated, which was filtered off, thoroughly mixed with a little light pstroleum at Oo, and refiltered. After drying on a tile, its weight was found to be 16 grams and its melting point 49-50°. View Article Online THE HYDROBROMIDFX OF UNDECYLENIC ACID. 1193 The filtrates on cooling to Oo deposited a further amount of solid, which was purified as already mentioned. In all, 26.5 grams of the acid of higher melting point were obtained from the 25 grams of undecglenic acid, and this we have found to be the best method of preparing it. w-Bromundecylic Acid, CH,Br*[CH,],*C02H, This acid, prepared in toluene solution in the manner just detailed, is insoluble in water, but freely soluble in the ordinary organic sol- vents, for example, alcohol, ether, chloroform, or benzene. Whilst easily soluble in warm light petroleum, it is only sparingly SO at the ordinary temperature, and very sparingly so at 0". Light petroleum therefore forms the most convenient solvent for its recrystallisation. It usually separates in clusters of fine needles, which, when pure, melt sharply at 51' without discoloration or evolution of gas. The sub- stance gave the following numbers on analysis : 0.1472, heated in a Carius tube with 0.4323 AgNO,, required 199C.C. of decinormnl NH,CNS to precipitate the excess of AgNO, Br = 30.05. C,,H,,O,Br requires Br = 30.19 per cent. The substance may be warmed either by itself or in organic solvents to a temperature considerably above its melting point without noteworthy evolution of hydrogen bromide occurring. The aqueous solutions of its alkali salts also are compsratively stable, showing little tendency to the separation of bromide and regeneration of undecylenic acid. o-Hydroxyundecylic Acid, CH2(0H)*[CH,],*C0,H. Thirteen grams of o-bromundecylic acid were dissolved in the calcu- lated quantity of normal sodium hydroxide solution, and the resulting Published on 01 January 1901. Downloaded by Fudan University 23/11/2017 08:36:04. liquid was warmed for 12 hours at 60-70' with excess of freshly precipi- tated silver hydroxide, the mixture being constantly agitated by means of a Witt stirrer. The action was then complete, bromine in my form being absent from the solution, The silver compounds were removed by filtration, treated with a little warm dilute sodium hydroxide solution, and again filtered. The filtrates mere united, and acidified with nitric acid, whereupon a solid acid separated, which was filtered off, washed with water, dried on porous tiles, and crystallised from benzene. On recrystallisation from much hot water, the acid separated in clusters of very long, fine needles, and melted at 70". From the above quantity of bromundecylic acid, 5.5 grams of the purified hydroxy-acid were obtained. 0.0801 gave 0*0800H,O and 0.1922 CO,. C = 65.43 ; H = 11.10. C,,H,,O, requires C = 65.35 ; H = 10.S9 per cent. 0.1206 of the calcium salt gave 0.0372 CaSO,. Ca= 9.07. (C,1H,0,)2Ca requires Ca = 9*05 per cent. View Article Online 1194 WALKER AND LUMSDEN: The acid is thus monobasic, and has the composition of a hydroxy- undecylic acid. It is easily soluble in alcohol or ether, moderately so in benzene, separating readily from a warm solution, and sparingly in light petroleum. One hundred parts of water at 20" dissolve 0.04 part of the acid. As it is more than 20 times as soluble in boiling water, it can easily be purified by crystallisstion frdm this solvent. A solution of the sodium salt containing 1 part in 200 is freely precipitated on addition of soluble salts of barium, caloium, strontium, silver, zinc, or mercury. The barium, strontium, calcium, and silver salts are much more soluble at the boiling point than st the ordinary temperature. The calcium salt was purified for analysis by recrys- tallisation frorn boiling water. The solution of sodium salt of tho above strength affords only a slight precipitate with a soluble mag- nesium salt. A more concentrated solution of the sodium salt, however, gave a curdy, somewhat stringy, precipitate, which dissolved slightly on heating, and was reprecipitated in a granular form on cooling the filtered solution, As this hydroxyundecylic acid is derived from the straight-ohain undecylenic acid, it also has its carbon atoms in a straight-chain. On oxidation with chromium trioxide, it is converted into a dicarboxylic acid having the same number of carbon atoms as itself. The hydroxyl which it contains is therefore part of a primary alcohol group. The acid therefore must have the constitution CII,(OH)I[~H~]!,*CO~H,and consequently the bromo-acid from which it was derived must be CH,Br*[CH,],*CO,H. n-Nonanedicnrboxylic Acid, CO,H*[CH,],=CO,H, Published on 01 January 1901. Downloaded by Fudan University 23/11/2017 08:36:04. One gram of o-hydroxyundecylicacid was dissolved in glacial acetic acid, and to the solution were added 10 c,c. of a 1 : 10 solution of chromium trioxide in glacial acetic acid, A slight rise of temperature was observed when the solutions were mixed.
Load more

Recommended publications
  • Retention Indices for Frequently Reported Compounds of Plant Essential Oils
    Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 9,375.433 B2 Dilly Et Al
    US009375433B2 (12) United States Patent (10) Patent No.: US 9,375.433 B2 Dilly et al. (45) Date of Patent: *Jun. 28, 2016 (54) MODULATORS OF ANDROGENSYNTHESIS (52) U.S. Cl. CPC ............. A6 IK3I/519 (2013.01); A61 K3I/201 (71) Applicant: Tangent Reprofiling Limited, London (2013.01); A61 K3I/202 (2013.01); A61 K (GB) 31/454 (2013.01); A61K 45/06 (2013.01) (72) Inventors: Suzanne Dilly, Oxfordshire (GB); (58) Field of Classification Search Gregory Stoloff, London (GB); Paul USPC .................................. 514/258,378,379, 560 Taylor, London (GB) See application file for complete search history. (73) Assignee: Tangent Reprofiling Limited, London (56) References Cited (GB) U.S. PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this 5,364,866 A * 1 1/1994 Strupczewski.......... CO7C 45/45 patent is extended or adjusted under 35 514,254.04 U.S.C. 154(b) by 0 days. 5,494.908 A * 2/1996 O’Malley ............. CO7D 261/20 514,228.2 This patent is Subject to a terminal dis 5,776,963 A * 7/1998 Strupczewski.......... CO7C 45/45 claimer. 514,217 6,977.271 B1* 12/2005 Ip ........................... A61K 31, 20 (21) Appl. No.: 14/708,052 514,560 OTHER PUBLICATIONS (22) Filed: May 8, 2015 Calabresi and Chabner (Goodman & Gilman's The Pharmacological (65) Prior Publication Data Basis of Therapeutics, 10th ed., 2001).* US 2015/O238491 A1 Aug. 27, 2015 (Cecil's Textbook of Medicine pp. 1060-1074 published 2000).* Stedman's Medical Dictionary (21st Edition, Published 2000).* Okamoto et al (Journal of Pain and Symptom Management vol.
    [Show full text]
  • Fatty Acids As Essential Adjuvants to Treat Various Ailments and Their Role in Drug Delivery: a Review
    Nutrition 65 (2019) 138À157 Contents lists available at ScienceDirect Nutrition journal homepage: www.nutritionjrnl.com Review article Fatty acids as essential adjuvants to treat various ailments and their role in drug delivery: A review Aakash Katdare B. Pharm, MS. Pharm, Shreya Thakkar B. Pharm, M. Pharm, Shivshankar Dhepale B. Pharm, MS. Pharm, Dignesh Khunt B. Pharm, M. Pharm, Manju Misra B. Pharm, M. Pharm, Ph.D. * Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research, Ahmedabad, India ARTICLE INFO ABSTRACT Article History: Since the discovery of fatty acids, a niche has been carved for their vital role as adjuvants in drug delivery and Received 23 May 2018 as treatment for various diseases. The literature has repeatedly described the essential role of various fatty Received in revised form 1 February 2019 acids in treating a wide range of diseases and disorders, from central nervous system diseases to wound heal- Accepted 20 March 2019 ing. The use of fatty acids has expanded to many horizons and in recent decades they have gained impor- tance as drug delivery adjuvants in addition to their auxiliary benefits in treating various diseases. Although Keywords: fatty acids aid in solving both formulation-based and therapeutic challenges to our knowledge, they have Polyunsaturated FA never been viewed as dual agents in modern scientific literature. The aim of this review was to provide this FA Lipids perspective and combine the very discreet literature about fatty acids, which includes their role as therapeu- Oils tic adjuvants and drug delivery agents. It gives insights on the use of fatty acids in treating the diseases of the Penetration enhancers eye, skin, central nervous system, viral diseases, and so on.
    [Show full text]
  • Biochemistry Prologue to Lipids
    Paper : 05 Metabolism of Lipids Module: 01 Prologue to Lipids Principal Investigator Dr. Sunil Kumar Khare, Professor, Department of Chemistry, IIT-Delhi Paper Coordinator and Dr. Suaib Luqman, Scientist (CSIR-CIMAP) Content Writer & Assistant Professor (AcSIR) CSIRDr. Vijaya-CIMAP, Khader Lucknow Dr. MC Varadaraj Content Reviewer Prof. Prashant Mishra, Professor, Department of Biochemical Engineering and Biotechnology, IIT-Delhi 1 METABOLISM OF LIPIDS Biochemistry Prologue to Lipids DESCRIPTION OF MODULE Subject Name Biochemistry Paper Name 05 Metabolism of Lipids Module Name/Title 01 Prologue to Lipids 2 METABOLISM OF LIPIDS Biochemistry Prologue to Lipids 1. Objectives To understand what is lipid Why they are important How they occur in nature 2. Concept Map LIPIDS Fatty Acids Glycerol 3. Description 3.1 Prologue to Lipids In 1943, the term lipid was first used by BLOOR, a German biochemist. Lipids are heterogeneous group of compounds present in plants and animal tissues related either actually or potentially to the fatty acids. They are amphipathic molecules, hydrophobic in nature originated utterly or in part by thioesters (carbanion-based condensations of fatty acids and/or polyketides etc) or by isoprene units (carbocation-based condensations of prenols, sterols, etc). Lipids have the universal property of being: i. Quite insoluble in water (polar solvent) ii. Soluble in benzene, chloroform, ether (non-polar solvent) 3 METABOLISM OF LIPIDS Biochemistry Prologue to Lipids Thus, lipids include oils, fats, waxes, steroids, vitamins (A, D, E and K) and related compounds, such as phospholipids, triglycerides, diglycerides, monoglycerides and others, which are allied more by their physical properties than by their chemical assests.
    [Show full text]
  • Measurement of Attenuation Cross-Sections of Some Fatty Acids in the Energy Range 122–1330 Kev
    Pramana – J. Phys. (2016) 87: 12 c Indian Academy of Sciences DOI 10.1007/s12043-016-1213-y Measurement of attenuation cross-sections of some fatty acids in the energy range 122–1330 keV D K GAIKWAD1,∗,PPPAWAR1 and T P SELVAM2 1Department of Physics, Dr Babasaheb Ambedkar Marathwada University, Aurangabad 431 004, India 2Radiation Physics and Advisory Division, BARC, Anushaktinagar, Mumbai 400 085, India ∗Corresponding author. E-mail: [email protected] MS received 14 June 2015; revised 7 August 2015; accepted 7 September 2015; published online 18 June 2016 Abstract. The mass attenuation coefficients (μm) have been measured for undecylic acid (C11H22O2), lau- ric acid (C12H24O2), tridecylic acid (C13H26O2), myristic acid (C14H28O2), pentadecylic acid (C15H30O2)and 57 133 137 60 22 palmitic acid (C16H32O2)using Co, Ba, Cs, Co and Na emitted γ radiation with energies 122, 356, 511, 662, 1170, 1275 and 1330 keV, respectively. The accurate values of the effective atomic number (Zeff), atomic cross-section (σt,), electronic cross-section (σe) and the effective electron density (Neff) have great signifi- cance in radiation protection and dosimetry. These quantities were obtained by utilizing experimentally measured values of mass attenuation coefficients (μm). A NaI(Tl) scintillation detector with 8.2% (at 662 keV) resolu- tion was used for detecting of attenuated γ -photons. The variation in Zeff and Neff of fatty acids with energy is discussed. The experimental and theoretical results are in good agreement within 2% deviation. Keywords. Fatty acids; NaI(Tl) scintillation detector; Zeff and Neff. PACS Nos 32.80.−t; 32.90.+a; 32.80.Fb; 20; 33.80.−b 1.
    [Show full text]
  • Environmental Alterations in Biofuel Generating Molecules in Zilla Spinosa
    Z. Naturforsch. 2017; 72(3-4)c: 77–91 Hemmat Khattab* and Zeinab El Marid Environmental alterations in biofuel generating molecules in Zilla spinosa DOI 10.1515/znc-2016-0151 acclimatization of Z. spinosa plants to soil water scarcity Received February 1, 2016; revised September 1, 2016; accepted associated with heat stress experienced during summer. September 4, 2016 In addition, the alterations in the fatty acid profiles may match biofuel requirements. In conclusion, the most ade- Abstract: Now days, production of fuels and petrochemi- quate growing season (spring) will be decisive for achiev- cals from renewable lignocellulosic biomass is an indis- ing high lipid productivity associated with improved pensable issue to meet the growing energy demand. biofuel quality in terms of high saturated fatty acids per- Meanwhile, the changes in the climate and soil topogra- centage that improves its cetane number. However, the phy influence the growth and development as well as can- dry summer season enhanced the accumulation of greater opy level of the lignocellulosic biomass. In this study, Zilla amount of lignin that may enhance the biodiesel quantity. spinosa Turr (Zilla) plants with similar age and size were collected from three main sectors (upstream, midstream, Keywords: biofuel; carbohydrates; cellulose; fatty acids; and downstream) of Wadi Hagul during spring (April) and heat stress; lignin; lipids; water scarcity; Zilla spinose summer (July) seasons. Environmental stresses evoked (Turr). reduction in the energy trapping pigments concomitant with increments in chlorophyll fluorescence in summer harvested plants particularly at downstream. Further- more, the biofuels generating compounds including car- 1 Introduction bohydrate, lignin, and lipid making the plant biomasses The Bio-energy from natural photosynthetic biomass can are greatly affected by environmental conditions.
    [Show full text]
  • NON-CLINICAL REVIEW(S) DEPARTMENT of HEALTH & HUMAN SERVICES Food and Drug Administration
    CENTER FOR DRUG EVALUATION AND RESEARCH APPLICATION NUMBER: 206089Orig1s000 NON-CLINICAL REVIEW(S) DEPARTMENT OF HEALTH & HUMAN SERVICES Food and Drug Administration PHARMACOLOGY/TOXICOLOGY MEMORANDUM CDER Stamp Date: September 27, 2018 NDA: 206089 Sponsor: Clarus Therapeutics, Inc. Drug: Testosterone undecanoate (JATENZO) Replacement therapy in adult males for conditions associated Indication: with a deficiency or absence of endogenous testosterone due to primary or hypogonadotropic hypogonadism Subject: Final Labeling Review Reviewer: Yangmee Shin, PhD Background: Clarus Therapeutics resubmitted NDA 206089 under a 505(b)(2) regulatory pathway following a 2nd Complete Response (CR) letter issued on March 22, 2018. NDA 206089 was first submitted on January 3, 2014 as a 505(b)(2) application. To support the nonclinical requirements of NDA via a 505(b)(2) pathway, the sponsor submitted published literature along with the findings of a 3-month oral toxicology study of Clarus’ oral testosterone undecanoate (TU) formulation in dogs. The sponsor also provided literature references to address ADME of TU by the oral route. The 3-month oral toxicology study in male dogs and relevant published literature were provided to support the use of borage oil as a novel excipient. The sponsor also supplied published literature regarding the fertility, pregnancy, and carcinogenicity of testosterone (T). Pharmacology and Toxicology recommended approval of the initial submission of NDA 206089 during the first cycle review. In the 1st resubmission to NDA 206089 on June 22, 2017, Clarus refiled the NDA as a 505(b)(1) application and provided nonclinical studies of oral TU including a 9-month oral toxicology study in male dogs, a battery of genotoxicity tests, a 6-month carcinogenicity study in Tg·rasH2 male mice, and a fertility study in male rats, upon agreement with the Division on November 19, 2015.
    [Show full text]
  • Fatty Acids, Trivial and Systematic Names
    FATTY ACIDS, TRIVIAL AND SYSTEMATIC NAMES Trivial Name Systematic Name Abbreviation Formic Acid Methanoic Acid Acetic Acid Ethanoic Acid Propionic Acid Propanoic Acid Butyric Acid Butanoic Acid 4:0 Valerianic Acid Pentanoic Acid 5:0 Caproic Acid Hexanoic Acid 6:0 Enanthic Acid Heptanoic Acid 7:0 Caprylic Acid Octanoic Acid 8:0 Pelargonic Acid Nonanoic Acid 9:0 Capric Acid Decanoic Acid 10:0 Obtusilic Acid 4-Decenoic Acid 10:1(n-6) Caproleic Acid 9-Decenoic Acid 10:1(n-1) Undecylic Acid Undecanoic Acid 11:0 Lauric Acid Dodecanoic Acid 12:0 Linderic Acid 4-Dodecenoic Acid 12:1(n-8) Denticetic Acid 5-Dodecenoic Acid 12:1(n-7) Lauroleic Acid 9-Dodecenoic Acid 12:1(n-3) Tridecylic Acid Tridecanoic Acid 13:0 Myristic Acid Tetradecanoic Acid 14:0 Tsuzuic Acid 4-Tetradecenoic Acid 14:1(n-10) Physeteric Acid 5-Tetradecenoic Acid 14:1(n-9) Myristoleic Acid 9-Tetradecenoic Acid 14:1(n-5) Pentadecylic Acid Pentadecanoic Acid 15:0 Palmitic Acid Hexadecanoic Acid 16:0 Gaidic acid 2-Hexadecenoic Acid 16:1(n-14) Sapienic Acid 6-Hexadecenoic Acid 16:1(n-10) Hypogeic Acid trans-7-Hexadecenoic Acid t16:1(n-9) cis-Hypogeic Acid 7-Hexadecenoic Acid 16:1(n-9) Palmitoleic Acid 9-Hexadecenoic Acid 16:1(n-7) Palmitelaidic Acid trans-9-Hexadecenoic Acid t16:1(n-7) Palmitvaccenic Acid 11-Hexadecenoic Acid 16:1(n-5) Margaric Acid Heptadecanoic Acid 17:0 Civetic Acid 8-Heptadecenoic Acid 17:1 Stearic Acid Octadecanoic Acid 18:0 Petroselinic Acid 6-Octadecenoic Acid 18:1(n-12) Oleic Acid 9-Octadecenoic Acid 18:1(n-9) Elaidic Acid trans-9-Octadecenoic acid t18:1(n-9)
    [Show full text]
  • Man Hon. Tsang Oakland, CA (US); E E SE, 9
    USOO81831 89B2 (12) United States Patent (10) Patent No.: US 8,183,189 B2 Chen et al. (45) Date of Patent: May 22, 2012 (54) PREPARATION OF A SULFURIZED 3,509,051 A 4, 1970 Farmer et al. MOLYBDENUMAMIDE COMPLEX AND 4,098,705. A 7/1978 Sakurai et al. 4,259,194 A 3, 1981 deVries et al. ADDITIVE COMPOSITIONS HAVINGLOW 4,259,195 A 3/1981 King et al. RESIDUAL ACTIVE SULFUR 4.261,843 A 4/1981 King et al. 4,263,152 A 4, 1981 King et al. (75) Inventors: Quinlai Chen, Walnut Creek, CA (US); 4,289,635 A 9, 1981 Schroeck Man Hon. Tsang Oakland, CA (US); E E SE,9 a. Gaurav Bhalla, Hercules, CA (US); 6,174,842 B1 1/2001 Gatto 5. William R. Ruhe, Jr., Benicia, CA (US) 6,358,894 B1 3/2002 Leta et al. 6,509,303 B1 1/2003 Gatto (73) Assignee: Chevron Oronite Company LLC, San 6,914,037 B2 7/2005 Gatto Ramon, CA (US) 2002fOO38.5256,962,896 A1B2 11/20054/2002 Ruhe,Callis etJr. al.et al. (*) Notice: Subject to any disclaimer, the term of this 38885, A. ck 239, Athlet al. ............. 508,198 patent is extended or adjusted under 35 2005/0209111 A1* 9, 2005 Ruhe et al. .................... 508/242 U.S.C. 154(b) by 191 days. OTHER PUBLICATIONS (21) Appl. No.: 12/570,974 PCT International Search Report PCT/US2009/059083 Date of mailing Jun. 18, 2010. (22) Filed: Sep. 30, 2009 * cited by examiner (65)65 PriorO PublicationDO Dat Primary Examiner – Walter D Griffin US 2011 FOOT718O A1 Mar.
    [Show full text]
  • A Review of Medium-Chain Fatty Acid Production
    processes Review Fermentation of Organic Residues to Beneficial Chemicals: A Review of Medium-Chain Fatty Acid Production Panagiota Stamatopoulou , Juliet Malkowski, Leandro Conrado, Kennedy Brown and Matthew Scarborough * Department of Civil and Environmental Engineering, University of Vermont, Burlington, VT 05405, USA; [email protected] (P.S.); [email protected] (J.M.); [email protected] (L.C.); [email protected] (K.B.) * Correspondence: [email protected] and [email protected] Received: 14 October 2020; Accepted: 23 November 2020; Published: 28 November 2020 Abstract: Medium-chain fatty acids (MCFAs) have a variety of uses in the production of industrial chemicals, food, and personal care products. These compounds are often produced through palm refining, but recent work has demonstrated that MCFAs can also be produced through the fermentation of complex organic substrates, including organic waste streams. While “chain elongation” offers a renewable platform for producing MCFAs, there are several limitations that need to be addressed before full-scale implementation becomes widespread. Here, we review the history of work on MCFA production by both pure and mixed cultures of fermenting organisms, and the unique metabolic features that lead to MCFA production. We also offer approaches to address the remaining challenges and increase MCFA production from renewable feedstocks. Keywords: chain elongation; carboxylate platform; medium-chain fatty acids; carboxylic acids; mixed culture fermentation 1. Introduction Microbial fermentation processes play an important role in food production, nutrient cycling, and pollution remediation. For more than 9000 years, humans have relied on microbial fermentation to produce and protect food [1], and fermentation processes have been used to convert wastes into valuable products since at least the 13th century [2].
    [Show full text]
  • United States Patent (19) 11 4,277,468 Hofmeister Et Al
    United States Patent (19) 11 4,277,468 Hofmeister et al. 45 Jul. 7, 1981 (54) 11-METHYLENESTEROIDS, THEIR 56) References Cited PREPARATION AND PHARMACEUTICAL U.S. PATENT DOCUMENTS PREPARATIONS CONTAINING THEM 3,927,046 12/1975 van den Broek ................ 260/.397.45 (75) Inventors: Helmut Hofmeister; Rudolf Wiechert; OTHER PUBLICATIONS Klaus Annen; Henry Laurent; Fried et al., JACS 83 (1961), pp. 4663-4464. Hermann Steinbeck, all of Berlin, Fed. Rep. of Germany Primary Examiner-Elbert L. Roberts Attorney, Agent, or Firm-Millen & White 73) Assignee: Schering Aktiengesellschaft, Berlin 57 ABSTRACT and Bergkamen, Fed. Rep. of 11-Methylene steroids of Formula I Germany OR 21 Appl. No.: 135,066 H2Cs Sesno CECC 22 Filed: Mar. 28, 1980 (30) Foreign Application Priority Data x1a Mar. 30, 1979 DE Fed. Rep. of Germany ....... 291.338 wherein m (51) Int. Cl. ................................................ CO7 1/OO R is hydrogen or acyl, and 52 U.S. C. ............................... 424/243; 260/397.45; X is oxygen or two hydrogen atoms 260/.397.5 have valuable pharmacological properties. 58) Field of Search ............. 260/.397.4, 397.45, 397.5; 424/243 10 Claims, No Drawings 4,277,468 2 acid, isonicotinic acid, furan-2-carboxylic acid, O 11-METHYLENE STEROIDS, THEIR tridecanoylglycolic acid, O-hexadecanoylglycolic acid, PREPARATION AND PHARMACEUTICAL g-tridecanoyloxypropionic acid, etc. Suitable sulfonic PREPARATIONS CONTAINING THEM acids include: methane-, ethane-, 3-chloroethane-, pro pane-, isopropane-, butane-, cyclopentane-, cyclohex BACKGROUND OF THE INVENTION ane-, benzene-, p-toluene- and p-chlorobenzenesulfonic The present invention relates to 11-methylene ste acids, etc.; and, furthermore, N,N-dimethyl-, N,N- roids, a process for their preparation, and pharmaceuti diethyl, bis(3-chloroethyl)-aminosulfonic acids, etc.; or cal preparations containing them.
    [Show full text]
  • UNITED STATES PATENT of FICE 2,345,632 POLAM DES ) Edwin A
    Patented Apr. 4, 1944 2,345,632 UNITED STATES PATENT OF FICE 2,345,632 POLAM DES ) Edwin A. Robinson, Chatham, and Maurice J. Kelley, Newark, N.J., assignors to National Oil Products Company, Harrison, N.J., a corpora tion of New Jersey N. No Drawing. Application May 20, 1939, serial No. 274,808 13 Claims. (CL 260-404.5) This invention relates to textile lubricants and vide a process for the preparation of textile softeners, more particularly to textile lubricants lubricants and softeners from polyamines. and softeners comprising mixed fatty polyamides. We have now found that polyamides having It has been proposed to use higher fatty the general formula R1CO-NR3-X-COR2 in amides, such as oleic acid amide, oleic acid which R1 stands for an alkyl radical containing methyl amide and oleic acid ethylene diamide from 7 to 21 carbon atoms, Ra stands for an alkyl as Softeners and lubricants for textile materials. radical containing from 1 to 4 Carbon atoms, ER3 Such amides are ordinarily prepared by reacting stands for hydrogen or an acyl group containing a fatty acid or fatty ester with a mono- or poly from 2 to 5 carbon atoms and X stands for the amine. The reaction of monoamines with higher O grouping (CRR-CR-R-NR) , Wherein R4 fatty acids or fatty esters yields products which and R5 stand for hydrogen or alkyl radicals, and n. are not readily dispersible in water, and since is a whole number, may be applied to textile these products contain no residual amino group, materials so as to impart thereto excellent soft they may not be solubilized to any substantial ness, drape and pliability without causing yellow extent by treatment with acids.
    [Show full text]