Process for the Production of Copper Phthalocyanine
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Title Formation and Properties of Various Amine Complexes of Iron
Formation and Properties of Various Amine Complexes of Title Iron-Phthalocyanine (Commemoration Issue Dedicated to Professor Eiji Suito on the Occasion of his Retirement) Author(s) Kobayashi, Takashi; Kurokawa, Fumio; Uyeda, Natsu Bulletin of the Institute for Chemical Research, Kyoto Citation University (1975), 53(2): 186-199 Issue Date 1975-09-25 URL http://hdl.handle.net/2433/76604 Right Type Departmental Bulletin Paper Textversion publisher Kyoto University Bull.Inst. Chem.Res., KyotoUniv., Vol. 53,No. 2, 1975 Formation and Properties of Various Amine Complexes of Iron-Phthalocyanine Takashi KOBAYASHI,Fumio KUROKAWA, and Natsu UYEDA* ReceivedMay 12, 1975 Theformation of additivecomplexes was studied in regard to iron-phthalocyanine(FePc) dispersed in variousamines. The compositionswere determinedby means of weight-lossmeasurement and fromthe thermal behavior of the additivecomplexes as observedby DTA and X-raypowder diffraction. The decompositiontemperature ranges from 100 to 300°C,above which the crystallitesare converted into the a-formof pure FePc. Infraredabsorption spectra indicated that amine molecules are co- ordinatedto the centralmetal of FePc, whilesome extra moleculesare freelyincluded in the space of crystallattice. Fromkinetic study of visiblelight absorptionspectra, it was foundthat newabsorption appearswhen the secondmolecule of the two is combinedto the Fe atom of Pc-ring,indicating that a chargetransfer mechanism is involvedin the complexformation. INTRODUCTION The behavior of transition metal derivatives of porphyrin calls for biological signifi- cance when it forms additive complexes with various n-donor molecules which have the ability of co-ordinating to the central metal ion. In the previous paper,') we reported on the formation and properties of similar complexes of zinc-derivative of tetrabenztetraazapor- phyrin (zinc-phthalocyanine) suspended in various n-donor dispersion media. -
Preparative Method of Novel Phthalocyanines from 3- Nitro
Available online a t www.derpharmachemica.com Scholars Research Library Der Pharma Chemica, 2012, 4(4):1397-1403 (http://derpharmachemica.com/archive.html) ISSN 0975-413X CODEN (USA): PCHHAX Preparative Method of Novel Phthalocyanines from 3- Nitro Phthalic Anhydride, Cobalt salt and Urea with Chloromethylpolyestyrene as a Heterogenous, Reusable and Efficient Catalyst Mohammad Ali Zolfigol 2, Ali Reza Pourali 1, Sami Sajjadifar 3,4 and Shohreh Farahmand 1,2,4 1Faculty of Chemistry, Bu-Ali Sina University, Hamedan, P.O. Box 6517838683, Iran 2School of Chemistry, Damghan University, Damghan, Iran 3Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran 4Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran _____________________________________________________________________________________________ ABSTRACT 3-Nitrophthalic anhydride was reacted with urea and cobalt salt in nitrobenzene under N 2 at 185°C and cobalt- tetraanitrophthalocyanine (CoTNP) was produced. Cobalt-tetraaminophthalocyanine (CoTAP) was produced by reduction of CoTNP caused by Sodium borohydride under N 2(g). CoTAP and chloromethylpolystyrene was refluxed in nitrobenzene or DMF at 180 oC for 12h. The mixture was cooled down to reach the room temperature and then solvent removed and the resulting precipitate was washed with water to remove excess CoTAP, and dried it to get a light green solid (CoTAP-linked-polymer). Kaywords Phthalocyanines, Cobaltetraminophthalocyanine, CoTAP ,Phthalocyanines linked polymer. _____________________________________________________________________________________________ INTRODUCTION Phthalocyanines are of interest not only as model compounds for the biologically important porphyrins but also because the intensely colored metal complexes are of commercial importance as dyes and pigments [1], the copper derivatives being an important blue pigment [2]. -
Phthalocyanine
Phthalocyanine sc-215718 Material Safety Data Sheet Hazard Alert Code EXTREME HIGH MODERATE LOW Key: Section 1 - CHEMICAL PRODUCT AND COMPANY IDENTIFICATION PRODUCT NAME Phthalocyanine STATEMENT OF HAZARDOUS NATURE CONSIDERED A HAZARDOUS SUBSTANCE ACCORDING TO OSHA 29 CFR 1910.1200. NFPA FLAMMABILITY1 HEALTH0 HAZARD INSTABILITY0 SUPPLIER Company: Santa Cruz Biotechnology, Inc. Address: 2145 Delaware Ave Santa Cruz, CA 95060 Telephone: 800.457.3801 or 831.457.3800 Emergency Tel: CHEMWATCH: From within the US and Canada: 877-715-9305 Emergency Tel: From outside the US and Canada: +800 2436 2255 (1-800-CHEMCALL) or call +613 9573 3112 PRODUCT USE ■ Phthalocyanine is a macrocyclic compound, It consists of four isoindole-class [(C6H4)C2N] units linked by four nitrogen atoms to form a conjugated chain, which take play in hosting various different metal ions in its centre. This macrocyclic structure like porphyrins(biopigments) is highly coloured Phthalocyanine derivatives derived from the basic compound of (C6H4C2N)4N4 are used as light-fast blue or green pigments. The hosted metals and substituted groups result in distinct colors; phthalocyanine (blue-green), copper phthalocyanine (blue), chlorinated copper phthalocyanine (green), and sulfonated copper phthalocyanine (green). They have also been involved in the study of photosensitizer chemistry or metal complex chemistry such as transition-metal complex catalyst chemistry for uniform polymerization, luminescence chemistry and spectrophotometric analysis, organic synthesis and polymerization. Phthalocyanine pigments are used in enamels, linoleum, inks, plastics, and rubber goods. Photoisomerizable phthalocyanines are used in rewritable CD or DVD printing. Some phthalocyanines such as fluoraluminium phthalocyanine are used in cancer treatment. Due to pi-electron cloud overlaps, phthalocyanines exhibit semiconductor property. -
Phthaloyl Amino Acids As Anti-Inflammatory And
MEDICINAL Med Chem Res (2014) 23:1701–1708 CHEMISTRY DOI 10.1007/s00044-013-0730-1 RESEARCH ORIGINAL RESEARCH Phthaloyl amino acids as anti-inflammatory and immunomodulatory prototypes Ana Cristina Lima Leite • Fa´bio Fernandes Barbosa • Marcos Verı´ssimo de Oliveira Cardoso • Diogo R. M. Moreira • Lucas Cunha D. Coeˆlho • Elany Barbosa da Silva • Gevanio Bezerra de Oliveira Filho • Valdeˆnia Maria Oliveira de Souza • Vale´ria Reˆgo A. Pereira • Luiza de C. Reis • Paulo Michel Pinheiro Ferreira • Claudia Pessoa • Almir Gonc¸alves Wanderley • Fernanda Virgı´nia B. Mota • Teresinha G. da Silva Received: 7 May 2013 / Accepted: 15 August 2013 / Published online: 12 September 2013 Ó Springer Science+Business Media New York 2013 Abstract A series of phthalimide analogs were synthesized Introduction by derivatization of phthalic anhydride, a highly toxic sub- stance, using a ‘‘one pot’’ condensation reaction to a-amino It is well known that the free radicals formed during acids. All phthaloyl amino acid derivatives presented anti-oral inflammation play an important role in killing the micro- inflammatory activity, but compounds 2e and 2g were found organism and activating leukocytes and macrophages. to possess the best activities comparable to thalidomide. Most Overproduction of these radicals is associated with a wide of the compounds effectively suppressed nitric oxide pro- range of pathological conditions (Ariel and Serhan, 2007; duction in murine cells stimulated with lipopolysaccharide. N- Nathan, 2002). Thus, it is important to develop anti- phthaloyl amino acids did not exhibit any significant cyto- inflammatory and immunomodulatory drugs that could toxicity in vitro when tested against tumor cells as well as a regulate the overproduction of these undesirable species spleen cell culture of BALB/c mice. -
Phthalocyanine Blue in Aqueous Solutions†
RSC Advances COMMUNICATION View Article Online View Journal | View Issue Phthalocyanine blue in aqueous solutions† Mark C. Staniford,a Marina M. Lezhninaab and Ulrich H. Kynast*a Cite this: RSC Adv.,2015,5,3974 Received 24th September 2014 Accepted 4th December 2014 DOI: 10.1039/c4ra11139g www.rsc.org/advances Using laponite nano-clay carriers, a facile method for the solubilisation Na0.7(H2O)n{(Li0.3Mg5.5)[Si8O20(OH)4]}, can be viewed as a nano- of natively insoluble phthalocyanines into aqueous solution is scaled hectorite derivative8 or a charged offspring of talcum, described. Copper(II) phthalocyanine, technologically a most relevant primarily consisting of disk-shaped platelets of 25 nm in pigment (C.I. Pigment Blue 15), thus yields hitherto unknown clear and diameter and 1 nm in height, which completely exfoliate to Creative Commons Attribution 3.0 Unported Licence. stable aqueous dispersions of either colloidal a-CuPc or monomeric form clear dispersions in water (see also Fig. 2 and the corre- CuPc, depending on details of the preparation. sponding caption).9 The resulting negatively charged platelets have been shown to adsorb numerous cationic dye species, among them Methy- Copper(II) phthalocyanine (CuPc, Fig. 1) is one of the most lene Blue10 or luminescent Rhodamine dyes,11 which can be frequently used pigments in painting and coating industries, attracted via polar and coulomb forces. However, very recently, with an annual production of approximately 60 000 t per year. the neutral and nonpolar dyes Indigo12 and Nile Red,13 both ffi The blue colorant possesses a very high extinction coe cient completely insoluble in water, have also been found to interact p–p* due to the intense transitions within the ligand electronic strong enough with nano-clays to be solubilised, the lumines- This article is licensed under a system. -
Phthalocyanine Adsorption to Graphene on Ir(111): Evidence for Decoupling from Vibrational Spectroscopy M
Supplemental material to: Phthalocyanine adsorption to graphene on Ir(111): Evidence for decoupling from vibrational spectroscopy M. Endlich,1, a) S. Gozdzik,1 N. N´eel,1 A. L. da Rosa,2, 3 T. Frauenheim,2 T. O. Wehling,2, 4 and J. Kr¨oger1, b) 1)Institut f¨ur Physik, Technische Universit¨at Ilmenau, D-98693 Ilmenau, Germany 2)Bremen Center for Computational Materials Science, University Bremen, D-28359 Bremen, Germany 3)Federal University of Minas Gerais, Department of Physics, 31270-901 Belo Horizonte, MG, Brazil 4)Institute for Theoretical Physics, University Bremen, D-28359 Bremen, Germany a)Electronic mail: [email protected] b)Electronic mail: [email protected] 1 Fig. S1. Relaxed geometry of free H2Pc with indicated Cartesian coordinates x, y. The z axis is oriented perpendicular to the xy plane. Specific molecule groups and atoms are labeled. The free H2Pc molecule (Fig. S1) exhibits D2h symmetry. The symmetry classes, Q, of this group together with the characters, χ, of specific reducible representations are summarized in Table SI. D2h E C2(z) C2(y) C2(x) I σ(xy) σ(xz) σ(yz) Γ 168 2 0 −2 0 58 4 2 Tab. S I. Symmetry operations of the D2h point group (the group elements are divided into classes, i.e., E: identity, C2: two-fold rotation with relevant rotation axes given in parentheses, I: inversion, σ: reflection with relevant mirror planes given in parentheses). Γ represents a set of specific reducible representations of the symmetry operations whose characters are given in the bottom row. -
Recent Advances and Future Prospects of Phthalimide Derivatives
Journal of Applied Pharmaceutical Science Vol. 6 (03), pp. 159-171, March, 2016 Available online at http://www.japsonline.com DOI: 10.7324/JAPS.2016.60330 ISSN 2231-3354 Recent Advances and Future Prospects of Phthalimide Derivatives Neelottama Kushwahaa*, Darpan Kaushikb aPranveer Singh Institute of Technology, Kanpur, India. bPrasad Institute of Technology, Jaunpur, India. ABSTRACT ARTICLE INFO Article history: Among bicyclic non-aromatic nitrogen heterocycles, phthalimides are an interesting class of compounds with a Received on: 21/05/2015 large range of applications. Phthalimide contains an imide functional group and may be considered as nitrogen Revised on: 13/09/2015 analogues of anhydrides or as diacyl derivatives of ammonia. They are lipophilic and neutral compounds and can Accepted on: 02/11/2015 therefore easily cross biological membranes in vivo and showing different pharmacological activities. In the Available online: 10/03/2016 present work compounds containing phthalimide subunit have been described as a scaffold to design new prototypes drug candidates with different biological activities and are used in different diseases as, for example Key words: AIDS, tumor, diabetes, multiple myeloma, convulsion, inflammation, pain, bacterial infection among others. Phthalimide derivatives, imide, biological activity. INTRODUCTION have served as starting materials and intermediates for the synthesis of many types of alkaloids and pharmacophores. Phthalimides possess a structural feature –CO-N(R)- CO- and an imide ring which help them to be biologically active Structure of Phthalimide and pharmaceutically useful. Phthalimides have received attention due to their androgen receptor antagonists (Sharma et Phthalimide is an imido derivative of phthalic acid. In al., 2012), anticonvulsant (Kathuria and Pathak, 2012), organic chemistry, imide is a functional group consisting of two antimicrobial (Khidre et al., 2011), hypoglycaemic (Mbarki and carbonyl groups bound to nitrogen. -
United States Patent Office (-(B) Lice (-(B)L
2,953,574 United States Patent Office Patented Sept. 20, 1960 1. 2 0.1 to 0.8, preferably 0.2-0.4. It is to be noted, as will be shown in the following examples, that some chlorine atoms are introduced during the reaction of benzene sul 2,953,574 fonyl chloride upon cobalt phthalocyanine. The degree DYE COMPOSITIONS CONTAINING COBALT of chlorination, however, appears to have little effect with PHTHALOCYANNE PHENYL SULFONES the exception of a slight shift toward the green. The Tellis A. Martin, Evansville, Ind., assignor to General affinity for fiber of such a mixture containing chlorinated Aniline & Film Corporation, New York, N.Y., a cor phthalocyanines is highly surprising and unexpected since poration of Delaware chlorinated cobalt phthalocyanine derivatives exhibit very poor affinity for fiber. No Drawing. Filed Dec. 29, 1953, Ser. No. 401,060 10 The mixture of cobalt phthalocyanine dyes character 3 Claims. (CI. 260-314.5) ized by the above general formula are prepared by (a) the reaction of a benzene sulfonyl chloride upon cobalt phthalocyanine or (b) by the reaction of cobalt phthalo This invention relates to dyeing compositions contain 5 cyanine sulfonyl chloride and either benzene, halogenated ing cobalt phthalocyanine phenyl sulfones and particu benzene, or alkylated benzene. An excess of the benzene larly to compositions consisting of mixtures of cobalt Sulfonyl chloride or the benzene or benzene derivative is phthalocyanine and cobalt phthalocyanine containing employed. These two reactions are best effected by heat from one to four phenylsulfonyl groups. ing the co-reactants in a suitable solvent, such as, di Metal phthalocyanines of the benzene series wherein 20 chlorobenzene, trichlorobenzene, nitrobenzene, and the one or all of the benzene nuclei contain quaternary or like, and in the presence of a catalyst such as, aluminum ternary salt groups attached to an aryl radical, which is chloride, ferric chloride, antimony chloride and the like, bridged to the phthalocyanine nucleus by -S-, -SO at a temperature ranging from 80-190° C. -
United States Patent to 11 B 4,001,273 Hetzel Et Al
United States Patent to 11 B 4,001,273 Hetzel et al. 45 Jan. 4, 1977 54 CONTINUOUS MANUFACTURE OF 56 References Cited PHTHALIMIDE UNITED STATES PATENTS (75) Inventors: Eckhard Hetzel; Ludwig Vogel, both 2,566,992 9/1951 Morgan et al. ................ 260/326 R of Frankenthal; Gerhard Rotermund, Heidelberg; Hans FOREIGN PATENTS OR APPLICATIONS Christoph Horn, Lambsheim, all of 300,770 8/1972 Austria .......................... 260/326 R Germany OTHER PUBLICATIONS 73) Assignee: BASF Aktiengesellschaft, Pfeifer et al., “Chem. Abstracts," vol. 77, p. 353, No. Ludwigshafen (Rhine), Germany 126,087s (1972). 22 Filed: July 8, 1974 Primary Examiner-Elbert L. Roberts Assistant Examiner-S. P. Williams 21 ) Appl. No.: 486,678 Attorney, Agent, or Firm-Johnston, Keil, Thompson & 44 Published under the second Trial Voluntary Shurtleff Protest Program on March 2, 1976 as document 57 ABSTRACT No. B 486,678. Continuous manufacture of phthalimide by reaction of 30) Foreign Application Priority Data phthalic anhydride with ammonia and washing the offgas with a melt containing phthalimide. The product July 10, 1973 Germany .......................... 233496 is a starting material for the manufacture of dyes, pesti 52) U.S.C. ........................................... 260/326 R cides and pigments, especially copper phthalocyanines. 51 Int. Cl........................................ C07D 209/.48 (58) Field of Search ................................ 260/326 R 7 Claims, No Drawings 4,001,273 1 2 from by-products and the proportion of phthalimide CONTINUOUS MANUFACTURE OF has been increased. Such an off-gas can be used with PHTHALIMIDE advantage for numerous syntheses; since the off-gas is conveniently trapped in aqueous alkali, for cxample in This application discloses and claims subject matter 5 sodium hydroxide solution, or potassium hydroxide described in German Patent Application No. -
Title Formation and Properties of Various Amine Complexes
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Kyoto University Research Information Repository Formation and Properties of Various Amine Complexes of Title Iron-Phthalocyanine (Commemoration Issue Dedicated to Professor Eiji Suito on the Occasion of his Retirement) Author(s) Kobayashi, Takashi; Kurokawa, Fumio; Uyeda, Natsu Bulletin of the Institute for Chemical Research, Kyoto Citation University (1975), 53(2): 186-199 Issue Date 1975-09-25 URL http://hdl.handle.net/2433/76604 Right Type Departmental Bulletin Paper Textversion publisher Kyoto University Bull.Inst. Chem.Res., KyotoUniv., Vol. 53,No. 2, 1975 Formation and Properties of Various Amine Complexes of Iron-Phthalocyanine Takashi KOBAYASHI,Fumio KUROKAWA, and Natsu UYEDA* ReceivedMay 12, 1975 Theformation of additivecomplexes was studied in regard to iron-phthalocyanine(FePc) dispersed in variousamines. The compositionswere determinedby means of weight-lossmeasurement and fromthe thermal behavior of the additivecomplexes as observedby DTA and X-raypowder diffraction. The decompositiontemperature ranges from 100 to 300°C,above which the crystallitesare converted into the a-formof pure FePc. Infraredabsorption spectra indicated that amine molecules are co- ordinatedto the centralmetal of FePc, whilesome extra moleculesare freelyincluded in the space of crystallattice. Fromkinetic study of visiblelight absorptionspectra, it was foundthat newabsorption appearswhen the secondmolecule of the two is combinedto the Fe atom of Pc-ring,indicating that a chargetransfer mechanism is involvedin the complexformation. INTRODUCTION The behavior of transition metal derivatives of porphyrin calls for biological signifi- cance when it forms additive complexes with various n-donor molecules which have the ability of co-ordinating to the central metal ion. -
Synthesis of Heterocycles from Anthranilic Acid and Its Derivatives
Synthesis of Heterocycles from Anthranilic acid and its Derivatives Per Wiklund All previously published papers were reproduced with permission from the publisher. Published and printed by Karolinska University Press Box 200, SE-171 77 Stockholm, Sweden © Per Wiklund, 2004 ISBN 91-7349-913-7 Abstract Anthranilic acid (2-aminobenzoic acid, Aa) is the biochemical precursor to the amino acid tryptophan, as well as a catabolic product of tryptophan in animals. It is also integrated into many alkaloids isolated from plants. Aa is produced industrially for production of dyestuffs and pharmaceuticals. The dissertation gives a historical background and a short review on the reactivity of Aa. The synthesis of several types of nitrogen heterocycles from Aa is discussed. Treatment of anthranilonitrile (2-aminobenzonitrile, a derivative of Aa) with organomagnesium compounds gave deprotonation and addition to the nitrile triple bond to form amine-imine complexed dianions. Capture of these intermediate with acyl halides normally gave aromatic quinazolines, a type of heterocyclic compounds that is considered to be highly interesting as scaffolds for development of new drugs. When the acyl halide was a tertiary 2-haloacyl halide, the reaction instead gave 1,4- benzodiazepine-3-ones via rearrangement. These compounds are isomeric to the common benzodiazepine drugs (such as diazepam, Valium®) which are 1,4- benzodiazepine-2-ones. Capture of the dianions with aldehydes or ketones, led to 1,2- dihydroquinazolines. Unsubstituted imine anions could be formed by treatment of anthranilonitrile with diisobutylaluminium hydride. Also in this case capture with aldehydes gave 1,2-dihydroquinazolines. Several different dicarboxylic acid derivatives of Aa were treated with dehydrating reagents, and the resulting products were more or less complex 1,3-benzoxazinones, one of which required X-ray crystallography confirm its structure. -
Intercalation of Copper Phthalocyanine Within Bulk
Intercalation of Copper Phthalocyanine Within Bulk Graphite as a New Strategy Toward the Synthesis of CuO-Based CO Oxidation Catalysts Gaëlle Couvret, Ghislain Genay, Cerise Robert, Loic Michel, Valérie Caps To cite this version: Gaëlle Couvret, Ghislain Genay, Cerise Robert, Loic Michel, Valérie Caps. Intercalation of Copper Phthalocyanine Within Bulk Graphite as a New Strategy Toward the Synthesis of CuO-Based CO Oxidation Catalysts. Frontiers in Chemistry, Frontiers Media, 2020, 8, 10.3389/fchem.2020.00735. hal-02928127 HAL Id: hal-02928127 https://hal.archives-ouvertes.fr/hal-02928127 Submitted on 2 Sep 2020 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. ORIGINAL RESEARCH published: 31 August 2020 doi: 10.3389/fchem.2020.00735 Intercalation of Copper Phthalocyanine Within Bulk Graphite as a New Strategy Toward the Synthesis of CuO-Based CO Oxidation Catalysts Gaëlle Couvret, Ghislain Genay, Cerise Robert, Loïc Michel and Valérie Caps* ICPEES (Institut de Chimie et Procédés pour l’Energie, l’Environnement et la Santé), Université de Strasbourg - ECPM / CNRS UMR 7515, Strasbourg, France Graphite is a widely available natural form of carbon with peculiar chemical and surface properties. It is essentially hydrophobic and consists in very stable stacks of graphene layers held together by highly delocalized π-π interactions.