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Transition Metal Phosphides for the Catalytic Hydrodeoxygenation of Waste Oils Into Green Diesel
catalysts Review Transition Metal Phosphides for the Catalytic Hydrodeoxygenation of Waste Oils into Green Diesel M. Consuelo Alvarez-Galvan * , Jose M. Campos-Martin * and Jose L. G. Fierro * Energy and Sustainable Chemistry Group (EQS), Instituto de Catálisis y Petroleoquímica, CSIC, c/Marie Curie, 2 Cantoblanco, 28049 Madrid, Spain * Correspondence: [email protected] (M.C.A.-G.); [email protected] (J.M.C.-M.); jlgfi[email protected] (J.L.G.F.) Received: 28 February 2019; Accepted: 15 March 2019; Published: 22 March 2019 Abstract: Recently, catalysts based on transition metal phosphides (TMPs) have attracted increasing interest for their use in hydrodeoxygenation (HDO) processes destined to synthesize biofuels (green or renewable diesel) from waste vegetable oils and fats (known as hydrotreated vegetable oils (HVO)), or from bio-oils. This fossil-free diesel product is produced completely from renewable raw materials with exceptional quality. These efficient HDO catalysts present electronic properties similar to noble metals, are cost-efficient, and are more stable and resistant to the presence of water than other classical catalytic formulations used for hydrotreatment reactions based on transition metal sulfides, but they do not require the continuous supply of a sulfide source. TMPs develop a bifunctional character (metallic and acidic) and present tunable catalytic properties related to the metal type, phosphorous-metal ratio, support nature, texture properties, and so on. Here, the recent progress in TMP-based catalysts for HDO of waste oils is reviewed. First, the use of TMPs in catalysis is addressed; then, the general aspects of green diesel (from bio-oils or from waste vegetable oils and fats) production by HDO of nonedible oil compounds are presented; and, finally, we attempt to describe the main advances in the development of catalysts based on TMPs for HDO, with an emphasis on the influence of the nature of active phases and effects of phosphorous, promoters, and preparation methods on reactivity. -
Preparation of Aromatic Carbonyl Compounds
~" ' MM II II II Ml I III II II I Ml II I II J European Patent Office © Publication number: 0 178 184 B1 Office_„. europeen- desj brevets^ » © EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 28.04.93 © Int. CI.5: C07C 45/45, C07C 49/76, C07C 51/58 © Application number: 85307320.3 @ Date of filing: 11.10.85 © Preparation of aromatic carbonyl compounds. © Priority: 11.10.84 US 659598 (73) Proprietor: RAYCHEM CORPORATION (a Dela- ware corporation) @ Date of publication of application: 300 Constitution Drive 16.04.86 Bulletin 86/16 Menlo Park, California 94025(US) © Publication of the grant of the patent: @ Inventor: Horner, Patrick James 28.04.93 Bulletin 93/17 139 Buckthorn Way Menlo Park California 94025(US) © Designated Contracting States: Inventor: Jansons, Vlktors AT BE CH DE FR GB IT LI NL SE 123 New York Avenue Los Gatos California 95030(US) References cited: Inventor: Gors, Helnrlch Carl EP-A- 0 024 286 EP-A- 0 069 598 2508 Mardell Way DE-A- 2 014 514 GB-A- 1 420 506 Mountain View California, 94043(US) GB-A- 2 103 604 US-A- 1 874 580 US-A- 3 282 989 Representative: Jay, Anthony William et al Raychem Limited Intellectual Property Law Department Faraday Road Dorcan Swindon Wiltshire (GB) 00 00 00 Note: Within nine months from the publication of the mention of the grant of the European patent, any person ® may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition CL shall be filed in a written reasoned statement. -
5 Phosphorus Oxychloride1 Acute Exposure Guideline Levels
Acute Exposure Guideline Levels for Selected Airborne Chemicals: Volume 10 Committee on Acute Exposure Guideline Levels Committee on Toxicology Board on Environmental Studies and Toxicology Division on Earth and Life Studies Copyright © National Academy of Sciences. All rights reserved. Acute Exposure Guideline Levels for Selected Airborne Chemicals: Volume 10 THE NATIONAL ACADEMIES PRESS 500 FIFTH STREET, NW WASHINGTON, DC 20001 NOTICE: The project that is the subject of this report was approved by the Governing Board of the National Research Council, whose members are drawn from the councils of the National Academy of Sciences, the National Academy of Engineering, and the Insti- tute of Medicine. The members of the committee responsible for the report were chosen for their special competences and with regard for appropriate balance. This project was supported by Contract No. W81K04-06-D-0023 and EP-W-09-007 be- tween the National Academy of Sciences and the U.S. Department of Defense and the U.S. Environmental Protection Agency. Any opinions, findings, conclusions, or recom- mendations expressed in this publication are those of the author(s) and do not necessarily reflect the view of the organizations or agencies that provided support for this project. International Standard Book Number-13: 978-0-309-21987-7 International Standard Book Number-10: 0-309-21987-6 Additional copies of this report are available from The National Academies Press 500 Fifth Street, NW Box 285 Washington, DC 20055 800-624-6242 202-334-3313 (in the Washington metropolitan area) http://www.nap.edu Copyright 2011 by the National Academy of Sciences. -
Psilocybin † † † ‡ Haden A
Review pubs.acs.org/chemneuro DARK Classics in Chemical Neuroscience: Psilocybin † † † ‡ Haden A. Geiger, Madeline G. Wurst, and R. Nathan Daniels*, , † Department of Pharmaceutical Sciences, Lipscomb University College of Pharmacy and Health Sciences, Nashville, Tennessee 37204, United States ‡ Department of Pharmacology, Vanderbilt University Medical Center, Nashville, Tennessee 37232-6600, United States ABSTRACT: Psilocybin is found in a family of mushrooms commonly known as “magic mushrooms” that have been used throughout history to induce hallucinations. In the late 1950s Albert Hofmann, of Sandoz Laboratories, identified and synthesized the psychoactive compounds psilocybin and psilocin which are found in psilocybe mushrooms. Psilocybin was marketed by Sandoz as Indocybin for basic psychopharmacological and therapeutic clinical research. Psilocybin saw a rapid rise in popularity during the 1960s and was classed as a Schedule I drug in 1970. This led to a significant decrease in psilocybin research. Recently, however, preliminary studies with psilocybin have shown promise as potential for the treatment of obsessive compulsive disorder, alcohol addiction, tobacco addiction, and major depressive disorder, and the treatment of depression in terminally ill cancer patients. This review describes in detail the synthesis, metabolism, pharmacology, adverse drug reactions, and importance of psilocybin to neuroscience in the past and present. KEYWORDS: Psilocybin, psilocin, indolealkylamine, hallucinogen, psychedelic, magic mushrooms, mushrooms, O-acetylpsilocin, indocybin I. INTRODUCTION The structure of psilocybin, and other indolealkylamine Psilocybin (1, Figure 1), a tryptamine alkaloid, is found in a hallucinogens, is similar to that of the endogenous neuro- family of mushroom-forming fungi that when ingested can transmitter serotonin (3), the hormone melatonin (4), and the hypothesized endogenous psychedelic, N,N-dimethyltrypt- cause hallucinations. -
Cancer Drug Pharmacology Table
CANCER DRUG PHARMACOLOGY TABLE Cytotoxic Chemotherapy Drugs are classified according to the BC Cancer Drug Manual Monographs, unless otherwise specified (see asterisks). Subclassifications are in brackets where applicable. Alkylating Agents have reactive groups (usually alkyl) that attach to Antimetabolites are structural analogues of naturally occurring molecules DNA or RNA, leading to interruption in synthesis of DNA, RNA, or required for DNA and RNA synthesis. When substituted for the natural body proteins. substances, they disrupt DNA and RNA synthesis. bendamustine (nitrogen mustard) azacitidine (pyrimidine analogue) busulfan (alkyl sulfonate) capecitabine (pyrimidine analogue) carboplatin (platinum) cladribine (adenosine analogue) carmustine (nitrosurea) cytarabine (pyrimidine analogue) chlorambucil (nitrogen mustard) fludarabine (purine analogue) cisplatin (platinum) fluorouracil (pyrimidine analogue) cyclophosphamide (nitrogen mustard) gemcitabine (pyrimidine analogue) dacarbazine (triazine) mercaptopurine (purine analogue) estramustine (nitrogen mustard with 17-beta-estradiol) methotrexate (folate analogue) hydroxyurea pralatrexate (folate analogue) ifosfamide (nitrogen mustard) pemetrexed (folate analogue) lomustine (nitrosurea) pentostatin (purine analogue) mechlorethamine (nitrogen mustard) raltitrexed (folate analogue) melphalan (nitrogen mustard) thioguanine (purine analogue) oxaliplatin (platinum) trifluridine-tipiracil (pyrimidine analogue/thymidine phosphorylase procarbazine (triazine) inhibitor) -
Solvent-Free and Safe Process for the Quantitative Production of Phosgene from Triphosgene by Deactivated Imino-Based Catalysts
Organic Process Research & Development 2010, 14, 1501–1505 Solvent-Free and Safe Process for the Quantitative Production of Phosgene from Triphosgene by Deactivated Imino-Based Catalysts Heiner Eckert* and Johann Auerweck Department of Chemistry, Technische UniVersitaet Muenchen, Lichtenbergstr. 4, Garching 85747, Germany Abstract: Scheme 1. Decomposition of triphosgene (1a) into carbon tetrachloride, carbon dioxide, and 1 equiv of phosgene (3) Phosgene is quantitatively formed from solid triphosgene in a solvent-free and safe process without any reaction heat, catalyzed by planar N-heterocycles with deactivated imino functions. The rate of phosgene generation is adjustable to the rate of phosgene consumption in the subsequent phosgenation reaction by thermal control, catalyst concentration, and in some cases, specific proper- ties of selected metal phthalocyanines. A thermal runaway reaction of this process is impossible. phosgene in most reactions, yet several phosgenation reactions are advantageously carried out with phosgene, that is, when excessive triphosgene is difficult to remove during the reaction Introduction workup because of its high boiling point of over 200 °C. Its Phosgene (3) is a highly useful and versatile chemical in excess can be destroyed by hydrolysis, when phosgenation performing syntheses.1a Although consisting of only four atoms, products are not sensitive to moisture as are carbonates, four important transformations can be carried out with it in carbamates, ureas, diarylketones, alkylhalides, cyanides, and organic -
Amide Activation: an Emerging Tool for Chemoselective Synthesis
Featuring work from the research group of Professor As featured in: Nuno Maulide, University of Vienna, Vienna, Austria Amide activation: an emerging tool for chemoselective synthesis Let them stand out of the crowd – Amide activation enables the chemoselective modification of a large variety of molecules while leaving many other functional groups untouched, making it attractive for the synthesis of sophisticated targets. This issue features a review on this emerging field and its application in total synthesis. See Nuno Maulide et al., Chem. Soc. Rev., 2018, 47, 7899. rsc.li/chem-soc-rev Registered charity number: 207890 Chem Soc Rev View Article Online REVIEW ARTICLE View Journal | View Issue Amide activation: an emerging tool for chemoselective synthesis Cite this: Chem. Soc. Rev., 2018, 47,7899 Daniel Kaiser, Adriano Bauer, Miran Lemmerer and Nuno Maulide * It is textbook knowledge that carboxamides benefit from increased stabilisation of the electrophilic carbonyl carbon when compared to other carbonyl and carboxyl derivatives. This results in a considerably reduced reactivity towards nucleophiles. Accordingly, a perception has been developed of amides as significantly less useful functional handles than their ester and acid chloride counterparts. Received 27th April 2018 However, a significant body of research on the selective activation of amides to achieve powerful DOI: 10.1039/c8cs00335a transformations under mild conditions has emerged over the past decades. This review article aims at placing electrophilic amide activation in both a historical context and in that of natural product rsc.li/chem-soc-rev synthesis, highlighting the synthetic applications and the potential of this approach. Creative Commons Attribution 3.0 Unported Licence. -
Pentachloride Hazard Summary Identification
Common Name: PHOSPHORUS PENTACHLORIDE CAS Number: 10026-13-8 RTK Substance number: 1525 DOT Number: UN 1806 Date: August 1999 ----------------------------------------------------------------------- ----------------------------------------------------------------------- HAZARD SUMMARY * Phosphorus Pentachloride can affect you when breathed * Exposure to hazardous substances should be routinely in. evaluated. This may include collecting personal and area * Phosphorus Pentachloride is a CORROSIVE air samples. You can obtain copies of sampling results CHEMICAL and contact can severely irritate and burn the from your employer. You have a legal right to this skin and eyes with possible eye damage. information under OSHA 1910.1020. * Breathing Phosphorus Pentachloride can irritate the nose * If you think you are experiencing any work-related health and throat. problems, see a doctor trained to recognize occupational * Breathing Phosphorus Pentachloride can irritate the diseases. Take this Fact Sheet with you. lungs causing coughing and/or shortness of breath. Higher exposures can cause a build-up of fluid in the lungs WORKPLACE EXPOSURE LIMITS (pulmonary edema), a medical emergency, with severe OSHA: The legal airborne permissible exposure limit shortness of breath. (PEL) is 1 mg/m3 averaged over an 8-hour * Exposure to Phosphorus Pentachloride can cause workshift. headache, dizziness, weakness, nausea and vomiting. * Phosphorus Pentachloride may damage the liver and NIOSH: The recommended airborne exposure limit is kidneys. 1 mg/m3 averaged over a 10-hour workshift. * Phosphorus Pentachloride is a REACTIVE CHEMICAL and an EXPLOSION HAZARD. ACGIH: The recommended airborne exposure limit is 0.85 mg/m3 averaged over an 8-hour workshift. IDENTIFICATION Phosphorus Pentachloride is a white to pale yellow, WAYS OF REDUCING EXPOSURE crystalline solid with a pungent odor. -
Pcls' Pocl3-VMR Patent Application Publication May 21, 2009 US 2009/0131653 A1
US 20090131653A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0131653 A1 Ratnam et al. (43) Pub. Date: May 21, 2009 (54) GENERATION OF PHOSPHORUS (86) PCT No.: PCT/IN2006/000151 OXYCHLORIDE AS BY-PRODUCT FROM PHOSPHORUS PENTACHLORIDE AND DMF § 371 (OX1), AND ITS USE FOR CHLORINATION (2), (4) Date/1 Dec- 31, 2007 REACTION BY CONVERTING INTO (30) Foreign Application Priority Data VILSMEIER-HAACK REAGENT May 4, 2005 (IN) ......................... .. 545/MUM/2005 (75) Inventors: Rakesh Ratnam, Maharashtra (IN); Publication Classi?cation Aurora Sundeep, Maharashtra (51) Int Cl SE1); M‘illzamgifd M0?zuddm’ C07H 1/00 (2006.01) “as ra( ) 0070251/30 (2006.01) C d Add (52) US. Cl. ....................................... .. 536/124; 564/278 orrespon ence ress: THENATHLAWGROUP (57) ABSTRACT 112 south West street A process is described Wherein after formation of ?rst crop of AleXandria, VA 22314 (Us) Vilsmeier-Haack reagent by reacting Phosphorus Pentachlo ride With N,N-dimethylformamide to form a ?rst crop of 73 A - ; PHARMEDMEDICARE Vilsmeier rea g ent as insoluble c rY stals ’ a b YP- roduct of this ( ) sslgnee PRIVATE LIMITED Mumbai reaction, the Phosphorus Oxy-Chloride, reacts With N,N (IN) ’ dimethylformamide to give a second crop of Vilsmeier reagent. This second crop of Vilsmeier reagent is soluble in DMF. This process makes it possible to double the yield of (21) APP1- N04 11/919,826 chlorinated substrate, such as sucrose-6-acetate or sucrose-6 benZoate, from the same quantity of Phosphorus Pentachlo (22) PCT Filed: Apr. 28, 2006 ride : Mechanism of Combined Vilsmeier Reagent for the Chlorination of sugars. -
United States Patent Office
Patented May 31, 1949 2,471,472 UNITED STATES2,471.472 PATENT OFFICE METHOD OF FORMING PHOSPHONIC AND THOPHOSPHONCACD CHLORDES Willard H. Woodstock, Flossmoor, Ill., assignor to Victor Chemical Works, a corporation of Illinois No Drawing. Application April 28, 1945, Seria No. 590,956 6 Claims. (CI. 260-543) 1. 2 This invention relates to a method of form phonic acids. Such chloroalkyl esters and ing phosphorus compounds and the resulting alkenyl-1-phosphonic esters above methyl are new compounds, as are the phosphorus oxydi products,of alkenyl and phosphorus more particularly oxydichlorides to East and sulfo chloride compounds themselves. dichlorides from addition products of olefins and In Formula. A R represents an alkyl or aryl phosphorus pentachloride. group, and X represents hydrogen or alkyl or Unsymmetrical olefins, having a terminal aryl grOp. double bond, react with PCls to form phosphorus In Formula. B R is a normal alkyl group. addition products, and these addition products Suitable olefins for the (A) reaction include may then be reacted with phosphorus pentasul O styrene, alpha methyl styrene, alpha chloroSty fide or phosphorus pentoxide. rene, indene, isobutylene, 2.2.diphenyl ethylene, Type A olefins which have two alkyl groups di-isobutylene, and the isoalkylenes where two or an aryl group attached to the 2-carbon gen carbon atoms are attached to the number 2 car erally react with phosphorus pentachloride to bon. Such isoalkylenes include isoamylenes, iso add -Cl to the 2-carbon and -PCl4 to the 1.- . heptenes, iso-octenes, etc. carbon. Type B olefins which have only one Starting hydrocarbons of the (B) type include alkyl group on the 2-carbon atom generally re propylene, buttene-1, pentene-1, octene-1, etc. -
LEGO® Stoichiometry
Finding Compound Formulas with LEGO Bricks by Dean Campbell and Richard Villarreal Matter is made of atoms. An element is matter which has all the same kind of atoms. A compound is matter which has a specific relative amount of elements. For example, water is a compound that is one part of the element oxygen and two parts of the element hydrogen. Ionic compounds are compounds that are made of ions – atoms that have an electrical charge. Positively charged ions are called cations and negatively charged ions are called anions. Even though the ions have an electrical charge, the compounds that they form have no electrical charge and are called electrically neutral. The charges of the ions determine how many cations must combine with how many anions to make a neutral compound. LEGO bricks can be used to figure out these combinations to get the proper formula of ionic compounds by arranging rows of bricks representing cations and bricks representing anions so that the rows must be of equal length. The following table gives an example of how this works: Cation Green brick Anion Yellow brick +1 (like sodium, Na+) 1 peg long -1 (like chloride, Cl-) 1 peg long +2 (like calcium, Ca2+) 2 pegs long -2 (like oxide, O2-) 2 pegs long +3 (like aluminum, Al3+) 3 pegs long -3 (like phosphide, P3-) 3 pegs long Example 1 Example 2 Example 3 Example 4 Example 1 - sodium chloride (also known as table salt): A green one-peg brick represents the positively charged sodium ion and the yellow one-peg brick represents the negatively charged chloride ion. -
The Effect of High-Dose Thiotepa, Alone Or in Combination with Other
Bone Marrow Transplantation (2007) 40, 891–896 & 2007 Nature Publishing Group All rights reserved 0268-3369/07 $30.00 www.nature.com/bmt ORIGINAL ARTICLE The effect of high-dose thiotepa, alone or in combination with other chemotherapeutic agents, on a murine B-cell leukemia model simulating autologous stem cell transplantation A Abdul-Hai, L Weiss, D Ergas, IB Resnick, S Slavin and MY Shapira Department of Bone Marrow Transplantation and Cancer Immunotherapy, Hadassah–Hebrew University Medical Center, Jerusalem, Israel The use of thiotepa (TH) is increasing, especially in stem Introduction cell transplantation, mainly due to its safety and blood– brain barrier penetration. We evaluated the use of TH in a Thiotepa (TH, triethylene thiophosphoramide), an ethylene murine model simulating autologous stem cell transplan- amide, developed by Lederle Laboratories in 1952, tation, with or without additional agents. Between 1 and possesses mechlorethamine-like alkylating activity and 11 days following inoculation of BALB/c mice with 105– has been used clinically for over 35 years.1 It is of particular 108 B-cell leukemia (BCL1) cells (simulating pre-trans- use in breast cancer, mainly as second-line treatment.2 plant leukemia loads), each group received an ‘induction- TH has been given intrathecally for carcinomatous like’ irradiation and/or cytotoxic regimen. Animals were meningitis, and intravesically for bladder carcinoma.3,4 either followed without treatment, or an adoptive transfer Mild-to-moderate activity was observed in several solid (AT) was performed to untreated BALB/c mice. Admi- tumors and hematological malignancies.1,5 There has nistered alone without AT, high-dose TH did not change been, however, a sustained interest in defining clinical roles the time to appearance of leukemia.