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Dibasic Acids for Nylon Manufacture
- e Report No. 75 DIBASIC ACIDS FOR NYLON MANUFACTURE by YEN-CHEN YEN October 1971 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE MENLO PARK, CALIFORNIA CONTENTS INTRODUCTION, ....................... 1 SUMMARY .......................... 3 General Aspects ...................... 3 Technical Aspects ..................... 7 INDUSTRY STATUS ...................... 15 Applications and Consumption of Sebacic Acid ........ 15 Applications and Consumption of Azelaic Acid ........ 16 Applications of Dodecanedioic and Suberic Acids ...... 16 Applications of Cyclododecatriene and Cyclooctadiene .... 17 Producers ......................... 17 Prices ........................... 18 DIBASIC ACIDS FOR MANUFACTURE OF POLYAMIDES ........ 21 CYCLOOLIGOMERIZATIONOF BUTADIENE ............. 29 Chemistry ......................... 29 Ziegler Catalyst ..................... 30 Nickel Catalyst ..................... 33 Other Catalysts ..................... 34 Co-Cyclooligomerization ................. 34 Mechanism ........................ 35 By-products and Impurities ................ 37 Review of Processes .................... 38 A Process for Manufacture of Cyclododecatriene ....... 54 Process Description ................... 54 Process Discussion .................... 60 Cost Estimates ...................... 60 A Process for Manufacture of Cyclooctadiene ........ 65 Process Description ................... 65 Process Discussion .................... 70 Cost Estimates ...................... 70 A Process for Manufacture of Cyclodecadiene -
The Human Urine Metabolome
The Human Urine Metabolome Souhaila Bouatra1, Farid Aziat1, Rupasri Mandal1, An Chi Guo2, Michael R. Wilson2, Craig Knox2, Trent C. Bjorndahl1, Ramanarayan Krishnamurthy1, Fozia Saleem1, Philip Liu1, Zerihun T. Dame1, Jenna Poelzer1, Jessica Huynh1, Faizath S. Yallou1, Nick Psychogios3, Edison Dong1, Ralf Bogumil4, Cornelia Roehring4, David S. Wishart1,2,5* 1 Department of Biological Sciences, University of Alberta, Edmonton, Alberta, Canada, 2 Department of Computing Sciences, University of Alberta, Edmonton, Alberta, Canada, 3 Cardiovascular Research Center, Massachusetts General Hospital, Harvard Medical School, Boston, Massachusetts, United States of America, 4 BIOCRATES Life Sciences AG, Innsbruck, Austria, 5 National Institute for Nanotechnology, Edmonton, Alberta, Canada Abstract Urine has long been a ‘‘favored’’ biofluid among metabolomics researchers. It is sterile, easy-to-obtain in large volumes, largely free from interfering proteins or lipids and chemically complex. However, this chemical complexity has also made urine a particularly difficult substrate to fully understand. As a biological waste material, urine typically contains metabolic breakdown products from a wide range of foods, drinks, drugs, environmental contaminants, endogenous waste metabolites and bacterial by-products. Many of these compounds are poorly characterized and poorly understood. In an effort to improve our understanding of this biofluid we have undertaken a comprehensive, quantitative, metabolome-wide characterization of human urine. This involved both computer-aided literature mining and comprehensive, quantitative experimental assessment/validation. The experimental portion employed NMR spectroscopy, gas chromatography mass spectrometry (GC-MS), direct flow injection mass spectrometry (DFI/LC-MS/MS), inductively coupled plasma mass spectrometry (ICP-MS) and high performance liquid chromatography (HPLC) experiments performed on multiple human urine samples. -
United States Patent Office Patented Aug
2,716,133 United States Patent Office Patented Aug. 23, 1955 2 process not covered by either of the two foregoing inven tions. The invention disclosed here describes these im 2,716,133 provements. - PURFICATION AND SEPARATION OF The water phase, containing mixed dicarboxylic acids DICARBOXYLIC ACDS as well as all the impurities previously listed (a, b, c, d, g, and h), is evaporated so that the solids content of the Leo S. Pooler, Chicago, Ill., assignor- to The C. P. Hall solution is increased to between 60% and 85% while Company of Illinois, Chicago, Ill., a corporation of being blown vigorously with air to effect further oxida Ohio tion. No Drawing. Application June 21, 1950, The dicarboxylic acid solution is then delivered to the Serial No. 169,542 crystallizer where it is cooled slowly to develop large crystals, after which the slurry is filtered and the crystals 6 Claims. (CI. 260-537) are washed. The mother liquor, is returned to the re actor for further oxidation. Small amounts of di This invention relates to the purification of dicar ; carboxylic acids are found in the mother liquor. boxylic acids produced from the oxidation of Saturated, The crude dicarboxylic acids coming from the filters unsaturated and substituted fatty acids. It includes the contain the same impurities as previously listed (a, b, c, use of the dichlorobenzenes (either pure Substances d, g, and h), but in lesser amounts than before the con or a mixture of the isomers) for the separation and puri centration, crystallization and filtration. fication of these -
Certificate of Analysis
National Institute of Standards and Technology Certificate of Analysis Standard Reference Material® 2277 Organic Acids in Methanol:Methylene Chloride This Standard Reference Material (SRM) is a solution of 24 organic acids in methanol:methylene chloride. This SRM is intended primarily for use in the calibration of chromatographic instrumentation used for the determination of organic acids. A unit of SRM 2277 consists of five 2 mL ampoules, each containing approximately 1.2 mL of solution. Certified Concentrations of Constituents: The certified concentration values and estimated uncertainties for the 24 constituents, expressed as mass fractions, are given in Table 1 along with the Chemical Abstract Service (CAS) Registry Numbers. The certified concentration values are based on results obtained from the gravimetric preparation of this solution and from the analytical results determined by using gas chromatography. A NIST certified value is a value for which NIST has the highest confidence in its accuracy in that all known or suspected sources of bias have been investigated or accounted for by NIST. Expiration of Certification: The certification of SRM 2277 is valid, within the measurement uncertainties specified, until 31 December 2017, provided the SRM is handled and stored in accordance with the instructions given in this certificate (see “Instructions for Use”). The certification is nullified if the SRM is damaged, contaminated, or otherwise modified. Maintenance of SRM Certification: NIST will monitor this SRM over the period of its certification. If substantive technical changes occur that affect the certification before the expiration of this certificate, NIST will notify the purchaser. Registration (see attached sheet) will facilitate notification. -
Novel Retinoid Derivatives and an Anti-Cancer Pharmaceutical Composition Comprising Said Compounds
(19) & (11) EP 1 390 343 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 235/78 (2006.01) 14.10.2009 Bulletin 2009/42 (86) International application number: (21) Application number: 02728253.2 PCT/KR2002/001014 (22) Date of filing: 29.05.2002 (87) International publication number: WO 2002/096857 (05.12.2002 Gazette 2002/49) (54) NOVEL RETINOID DERIVATIVES AND AN ANTI-CANCER PHARMACEUTICAL COMPOSITION COMPRISING SAID COMPOUNDS NEUE RETINOIDDERIVATE UND EINE PHARMAZEUTISCHE ANTI-KREBS- ZUSAMMENSETZUNG, DIE DIESE VERBINDUNGEN ENTHÄLT NOUVEAUX DERIVES DE RETINOIDE ET COMPOSITION PHARMACEUTIQUE ANTI-CANCER RENFERMANT LESDITS COMPOSES (84) Designated Contracting States: • HAN, Hye-Sook AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU 50-44 Jungkok-dong MC NL PT SE TR Seoul 143-220 (KR) Designated Extension States: • KIM, So-Mi AL LT LV MK RO SI 306-501 Deayoudealim Apt. Cheju-si 690-012 (KR) (30) Priority: 29.05.2001 KR 2001029813 • KIM, Dong-Myong 20.03.2002 KR 2002015016 1330-1207 Mokdongshinsigaji Apt. Seoul 158-076 (KR) (43) Date of publication of application: •OH, Deok-Kun 25.02.2004 Bulletin 2004/09 301-103 Jugong Apt. Kyunggi-do 427-040 (KR) (73) Proprietor: Chebigen Co., Ltd. • PARK, Jong-Sup Seoul 135-080 (KR) 1-2202 Wooseong Apt. Seoul 135-270 (KR) (72) Inventors: •BAE, Tae-Sung • UM, Soo-Jong 139, Sooryong 108-102 Parktown Seoan Apt. Jeonlabuk-do 576-922 (KR) Kyunggi-do 463-020 (KR) • SIN, Hong-Sig (74) Representative: Grünecker, Kinkeldey, 103-1602 Woobang Apt. -
Identification of Methyl-Branched Chain Dicarboxylic Acids in Amniotic Fluid and Urine in Propionic and Methylmalonic Acidemia
DICARBOXYLIC ACIDS IN AMNIOTIC FLUID 003 1-39981841181 I - 1 185$02.00/0 PEDIATRIC RESEARCH Vol. 18, No. 1 1, 1984 Copyright O 1984 International Pediatric Research Foundation, Inc Prinred in US.A. Identification of Methyl-branched Chain Dicarboxylic Acids in Amniotic Fluid and Urine in Propionic and Methylmalonic Acidemia CORNELIS JAKOBS, LAMBERTUS DORLAND, LAWRENCE SWEETMAN, MARINUS DURAN, WILLIAM L. NYHAN, AND SYBE K. WADMAN Department ofpediatricr, Academic Hospital of the Free University ofAmsterdarn, Amsterdam, The Netherlands [C.J.], University Children's Hospital "Het Wilhelmina Kinderziekenhuis, " Utrecht, The Netherlands [L.D.,M.D.,S.K.W.], and Department of Pediatrics, University of California Sun Diego, La Jolla, California 92093 [L.S.,W.L.N.] ABSTRACT. 3-Methyladipic, 4-methylpimelic, 4-meth- were considerably greater than in AF. Evidence was obtained for ylsuberic, pimelic, and azeleic acids were identified by gas the presence of a number of other methyl-branched dicarboxylic chromatography-mass spectrometry in the amniotic fluid acids. 4-MPA and 4-MSuA have not previously been identified of fetuses with propionic acidemia. These compounds were in body fluids. virtually undetectable in normal amniotic fluid. Concentra- tions much higher than those of the amniotic fluid were MATERIALS AND METHODS found in the urine of neonatal infants with propionic aci- demia and methylmalonic acidemia. It appears that the Normal AF samples were obtained between 16 and 18 weeks accumulation of these compounds is a consequence of the of pregnancy by amniocentesis and stored at -20°C. Amniotic accumulation of propionyl-CoA. Evidence was obtained for fluids from pregnancies at risk were sent for analysis as sterile the presence of other methyl-branched chain dicarboxylic fluids or frozen on dry ice and stored prior to analysis at -20°C. -
C18 Diacid Market to Grow and Expand Into an Array of Novel Products with Superior Properties Allyson Beuhler, Phd
C18 Diacid Market to Grow and Expand Into an Array of Novel Products with Superior Properties Allyson Beuhler, PhD Overview Diacids are a commercially important class of chemicals, produced annually in tens of thousands of tons with applications in a variety of end uses. The difunctionality of diacids makes them particularly useful buildinG blocks in condensation polymerization applications. Due to the variable aliphatic chain lenGth between the two carboxylic acid Groups, a variety of physical properties are observed. As such, the properties of the products made can be tailored by choosinG the appropriate chain lenGth. Octadecanedioic acid (ODDA) is a C18 diacid that is now commercially available from two pathways, one usinG microbial fermentation and one usinG metathesis of natural oils. The latter pathway is expected to dramatically increase the availability of C18 diacid and lower its cost. The products made from this diacid typically show superior properties, such as water and chemical resistance, as compared to the shorter chain alternatives. Consequently, a myriad of new products made from ODDA should now be accessible. Aliphatic diacids, also known as α,ω-dicarboxylic acids, comprise two carboxylic acid functional groups linked by an aliphatic hydrocarbon spacer. The General formula for this class of compound is HO2C(CH2)nCO2H. Typically, n is between 0 and 22. Table 1 describes the diacid portfolio that is available in the market place at research and/or commercial levels. Table 1. Selected diacids IUPAC Name Common Name Carbon -
C,-C,O-Dicarboxylic Aciduria: Investigations of a Patient with Riboflavin Responsive Multiple Acyl- Coa Dehydrogenation Defects
Pediatr. Res. 16: 861-868 (1982) C,-C,o-Dicarboxylic Aciduria: Investigations of a Patient with Riboflavin Responsive Multiple Acyl- CoA Dehydrogenation Defects N. GREGERSEN,'~'' H. WINTZENSEN, S. KBLVRAA E. CHRISTENSEN, M. F. CHRISTENSEN, N. J. BRANDT, AND K. RASMUSSEN Research Laboratory for Metabolic Disorders, University Department of Clinical Chemistry, Aarhus Kommunehospital, Aarhus; Department of Pediatrics, Herning Hospital, Herning; Institute of Human Genetics, University of Aarhus, Aarhus; and Section of Clinical Genetics, University Department of Pediatrics and of Gynaecology and Obstetrics, Rigshospitalet, Copenhagen, Denmark. Summary one or more acute attacks, most frequently characterized by a Reye-like syndrome (37) with vomitGg and increasing lethargy The abnormal metabolites-adipic, suberic, and sebacic acids- that eventually leads to coma. Biochemical characteristics includes were detected in large amounts in the urine of a boy during a metabolic acihosis, hypoglycemia, fatty infiltration of the liver, Reye's syndrome-like crisis. Substantial amounts of 5-OH-caproic and large amounts of the Cs-CIO-dicarboxylicacids, i.e., adipic, acid, caproylglycine, glutaric acid, and 3- OH-butyric acid and suberic, and sebacic acids in the urine. In spite of the similarities moderately elevated amounts of ethylmalonic acid, methylsuccinic between the clinical pictures during the acute attacks in these acid, 3-OH-isovaleric acid, and isovalerylglycine were also found. patients, the biochemical presentation exhibited a high degree of -
Recent Trends in the Development of Sustainable Catalytic Systems for The
Recent trends in the development of sustainable catalytic systems for the oxidative cleavage of cycloalkenes by hydrogen peroxide Tony Cousin, Gregory Chatel, Nathalie Kardos, Bruno Andrioletti, Micheline Draye To cite this version: Tony Cousin, Gregory Chatel, Nathalie Kardos, Bruno Andrioletti, Micheline Draye. Recent trends in the development of sustainable catalytic systems for the oxidative cleavage of cycloalkenes by hydrogen peroxide. Catalysis Science & Technology, Royal Society of Chemistry, 2019, 9 (19), pp.5256-5278. 10.1039/C9CY01269A. hal-02357883 HAL Id: hal-02357883 https://hal.archives-ouvertes.fr/hal-02357883 Submitted on 2 Apr 2021 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Please do not adjust margins Catalysis Science & Technology MINIREVIEW Recent trends in the development of sustainable catalytic systems for the oxidative cleavage of cycloalkenes by hydrogen peroxide Received 00th January 20xx, a,b a a b† a† Accepted 00th January 20xx Tony Cousin , Gregory Chatel , Nathalie Kardos , Bruno Andrioletti and Micheline Draye DOI: 10.1039/x0xx00000x Dicarboxylic acids constitute one of the most important oxygenated intermediates in the chemical industry originating a wide range of daily products: fibers, pharmaceuticals, cosmetics, lubricants, pesticides and plasticizers. -
Metabolomic Analyses Reveals New Stage-Specific Features of the COVID-19
Early View Original research article Metabolomic analyses reveals new stage-specific features of the COVID-19 Hongling Jia, Chaowu Liu, Dantong Li, Qingsheng Huang, Dong Liu, Ying Zhang, Chang Ye, Di Zhou, Yang Wang, Yanlian Tan, Kuibiao Li, Fangqin Lin, Haiqing Zhang, Jingchao Lin, Yang Xu, Jingwen Liu, Qing Zeng, Jian Hong, Guobing Chen, Hao Zhang, Lingling Zheng, Xilong Deng, Changwen Ke, Yunfei Gao, Jun Fan, Biao Di, Huiying Liang Please cite this article as: Jia H, Liu C, Li D, et al. Metabolomic analyses reveals new stage- specific features of the COVID-19. Eur Respir J 2021; in press (https://doi.org/10.1183/13993003.00284-2021). This manuscript has recently been accepted for publication in the European Respiratory Journal. It is published here in its accepted form prior to copyediting and typesetting by our production team. After these production processes are complete and the authors have approved the resulting proofs, the article will move to the latest issue of the ERJ online. Copyright ©The authors 2021. This version is distributed under the terms of the Creative Commons Attribution Non-Commercial Licence 4.0. For commercial reproduction rights and permissions contact [email protected] Metabolomic analyses reveals new stage-specific features of the COVID-19 Hongling Jia1,2#, Chaowu Liu3#, Dantong Li15#, Qingsheng Huang4#, Dong Liu5#, Ying Zhang1#, Chang Ye4, Di Zhou6, Yang Wang6, Yanlian Tan2, Kuibiao Li1, Fangqin Lin4, Haiqing Zhang7, Jingchao Lin6, Yang Xu1, Jingwen Liu1, Qing Zeng1, Jian Hong8, Guobing Chen9, Hao Zhang10, -
Co-Crystallisation of Α,Ω-Dicarboxylic Acids with Nicotinamide and Isonicotinamide
CO-CRYSTALLISATION OF α,ω-DICARBOXYLIC ACIDS WITH NICOTINAMIDE AND ISONICOTINAMIDE by RAJA SEKHAR VOGURI under the supervision of Dr. Maryjane Tremayne A thesis submitted to The University of Birmingham for the degree of MASTER OF RESEARCH School of Chemistry The University of Birmingham September 2010 University of Birmingham Research Archive e-theses repository This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder. ABSTRACT Pharmaceutical co-crystallisation is an alternative and potentially reliable method to manipulate physical properties of API‟s via supramolecular synthesis. A number of binary co-crystals were synthesised using different solvents, different stoichiometric ratios (ratio of starting materials) and different methods of synthesis (solvent-mediated crystallisation, solvent-drop grinding and neat grinding), with a view to investigate solvent and stoichiometric effects on the materials formed. Selected α,ω-alkanedicarboxylic acids (HOOC-(CH2)n-COOH) were crystallised with nicotinamide for n = 0, 1, 2, 4, 5, 6, 7 and isonicotinamide for n = 5, 6, 7 yielding 12 new solid materials. The melting point of the starting materials and new products are determined and analysed, and the new crystalline materials characterised using NMR, FTIR, powder X-ray diffraction data (PXRD) and single X-ray diffraction data (SXRD). -
And Long-Chain Dicarboxylic Aciduria in Patients with Zellweger Syndrome and Neonatal Adrenoleukodystrophy
003 1-3998/86/2001-0062$02.00/0 PEDIATRIC RESEARCH Vol. 20, No. 1, 1986 Copyright O 1986 International Pediatric Research Foundation, Inc. Printed in U.S.A. Medium- and Long-Chain Dicarboxylic Aciduria in Patients with Zellweger Syndrome and Neonatal Adrenoleukodystrophy Departement de Biochimie (INSERM U 75), Faculte de Medecine Necker-Enfants Malades; Service de Neuropediatrie et Service d'Endocrinologie (ZNSERM U ISS), H6pital Saint- Vincent-de-Paul, Paris, Cedex, France ABSTRACT. This study reports that patients with neo- CASE REPORTS natal adrenoleukodystrophy and Zellweger syndrome ex- crete a very peculiar pattern of organic acids. Dicarboxylic Table 1 summarizes the clinical and biological data in the acids with an even number of carbon atoms (adipic, suberic, seven patients. More detailed clinical and histopathological data sebacic, 2- and 3-hydroxy-sebacic, hexadecanedioic), as have been reported elsewhere (9, 10). None of the patients had well as with an odd number of carbon atoms (pimelic, attack of drowsiness, vomiting, or episodes of hypoglycemia and azelaic, un-, tri-, and pentadecanedioic) were found in acidosis during the course of the disease. The days before the excess in the urines of six patients with neonatal adreno- study, all patients were eating a normal controlled diet providing leukodystrophy and one with Zellweger syndrome. The a daily caloric intake of 100-120 kcal/kg, with 2.5 g/kg protein accumulation of dicarboxylic acids, reflecting an impair- and 2 g/kg lipid. Estimated dietary intake of phytol was less than ment of their &oxidation in mitochondria and/or peroxi- 1 mg/kg/day. Patients 1, 2, and 5 received Phenobarbital and somes, thus appears as an additional useful marker of patients 3 and 4, Carbamazepine.