- Synthesis of 1-hydroxymethylene-1,1-bis(phosphonic acids) from acid anhydrides: Preparation of a new cyclic 1-acyloxymethylene-1,1-bis(phosphonic acid)
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In continuing with our work to find new pathways to bis(phosphonate) structures we report on their synthesis from tris(trimethylsilyl) phosphite and acid anhydride. This new synthesis allows a direct access to a 1-hydroxymethylene-1,1-bis(phosphonic acid) functionalised by a carboxylic function on the side chain. Moreover, we describe the formation of an original cyclic bis(phosphonate) obtained from phthalic anhydride. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Guenin, Erwann,Degache, Estelle,Liquier, Jean,Lecouvey, Marc
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Read Online
- Strategies for the preparation of (1-acetyloxyethylidene)-1,1-bisphosphonic acid derivatives
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The novel strategies for the synthesis of acetylated etidronic acid derivatives were investigated. (1-Acetyloxyethylidene)-1,1-bisphosphonic acid and its P,P′-dimethyl, trimethyl and tetramethyl esters were prepared in high 81-100% yields.
- Turhanen, Petri A.,Veps?l?inen, Jouko J.
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Read Online
- Method for preparing hydroxyalkylene diphosphonic acid from yellow phosphorus
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The invention relates to the technical field of scale inhibitors, in particular to a preparation method of hydroxyalkylene diphosphonic acid. The preparation method comprises the following steps: insufficiently burning yellow phosphorus in oxygen to obtain phosphorus trioxide, and then making the phosphorus trioxide react with fatty acid and water to obtain hydroxyalkylene diphosphonic acid. The method has the advantages of fewer raw materials and simple steps, thereby saving the reaction time and lowering the energy consumption. A large amount of hydrogen chloride gas is not generated in thereaction process, and a hydroxyalkylene diphosphonic acid product with high yield and good quality can be obtained.
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Paragraph 0016-0023
(2020/05/30)
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- "water soluble" palladium nanoparticle engineering for C-C coupling, reduction and cyclization catalysis
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The use of Pd nanoparticles (Pd-NPs) to realize several important organic reactions allows efficient catalysis with low metal loading (1000 ppm), hence providing a greener catalytic system. However, to be truly green Pd-NPs need to be synthesized in a sustainable manner and be able to react in aqueous media in order to avoid the use of organic solvents. Here we describe an original and eco-friendly synthesis of Pd-NPs (using benign reactants and simple conditions) perfectly stable in water. Remarkably, this synthesis allows for control over their size and morphology by simply tuning the pH of the stabilizer. We then evaluate the catalytic efficiency of these Pd-NPs on six different model reactions (Suzuki Miyaura, Sonogashira, Heck, nitrophenol reduction and pentynoic cycloisomerization) in aqueous media. We show that the stabilizer structure influences the activity owing to its ability to promote the mass transfer of the organic substrates towards the NP surface in the aqueous environment. Finally, catalytic evaluations show that our nano-catalysts prepared in an eco-friendly manner are among the best catalysts described so far in the literature in each case, with high turnover frequencies reached with a low loading of palladium.
- Iben Ayad,Belda Marín,Colaco,Lefevre,Méthivier,Ould Driss,Landoulsi,Guénin
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supporting information
p. 6646 - 6657
(2019/12/26)
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- Copolymers having gem-bisphosphonate groupings
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A copolymer includes a main hydrocarbon chain and side groups including carboxylic groups and polyoxyalkylate groups. The copolymer further includes gem-bisphosphonate groups. A composition, such as n admixture for suspensions of mineral particles, includes the copolymer. The copolymer can be used for fluidifying suspensions of mineral particles and maintaining the fluidity of such suspensions. The copolymer can also be used for reducing the sensitivity of hydraulic compositions to clays and alkaline sulfates.
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Page/Page column 8
(2018/10/15)
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- 1-hydroxyethylidene-1,1-diphosphonic acid and ethyl acetate coproduction process
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The invention discloses a 1-hydroxyethylidene-1,1-diphosphonic acid and ethyl acetate coproduction process. The coproduction process is completed by taking phosphorus trichloride, glacial acetic acid, deionized water and ethyl alcohol according to steps as shown in the specification. By replacement of deionized water with ethyl alcohol as an esterlysis agent, a great quantity of acetic acid can be generated after alcoholysis of esters into HEDP (1-hydroxyethylidene-1,1-diphosphonic acid), ethyl acetate is quickly generated by ethyl acetate and acetic acid under acceleration of strong organic acid HEDP. Due to simultaneity and mutual promotion of two reactions, reaction rate is increased while waste recycling is realized, economic benefits are increased, wastewater quantity is decreased, and indexes of prepared HEDP coproduced ethyl acetate products accord with indexes of industrial products.
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Paragraph 0014; 0015; 0016; 0017; 0018; 0020
(2018/01/19)
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- Hydroxyethylidene diphosphonic acid production process for the concentration of the low-concentration acetic acid
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The invention provides a low-concentration acetic acid concentrating process for a hydroxyl ethylidene diphosphonic acid production process. The process provided by the invention has the advantages that the process is a continuous concentrating process and the concentration of finally-collected acetic acid is higher than 99%. The process is characterized by being implemented by a mixing kettle, a reactor, a gas-liquid separator and more than three hydrolysis reactors. According to the process, a process flow is shown in a drawing, a liquid intermediate product, i.e. hydroxyl ethylidene diphosphonic acetate, obtained through the gas-liquid separator is sequentially and cyclically filled in the hydrolysis reactors of one to n, the sequential hydrolysis and discharging are carried out, and an obtained acetic acid solution sequentially enters a next hydrolysis reactor and participates in hydrolysis, so that the continuous increase of the concentration and the comprehensive utilization of heat energy are realized.
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Paragraph 0020-0026
(2017/01/23)
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- A high-purity arsenic of the process for the preparation of hydroxy ethylidene diphosphonic acid
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The invention relates to a preparation process for high-purity low-arsenic hydroxyethylidene diphosphonic acid. The preparation process comprises the following steps: with phosphorus trichloride, acetic acid and ammonium thioacetate as raw materials, controlling process conditions at first, reacting acetic acid with phosphorus trichloride in a reaction vessel to produce hydroxyethylidene diphosphonic acid and adding ammonium thioacetate in the process of the reaction; and then subjecting an obtained material to concentration and air flushing to remove impurities, adding ammonium thioacetate and carrying out arsenic removal and centrifugation so as to obtain the high-purity low-arsenic hydroxyethylidene diphosphonic acid. According to the invention, scientific technology is employed for product purification, no other substance like a crystal nucleus and a crystallization promoter is added, so no new impurity is introduced. Hydroxyethylidene diphosphonic acid in the high-purity low-arsenic hydroxyethylidene diphosphonic acid prepared in the invention is more than 95%, and arsenic content in the high-purity low-arsenic hydroxyethylidene diphosphonic acid is less than 2 ppm; the preparation process overcomes problems in packaging, transporting and on-site application of liquid hydroxyethylidene diphosphonic acid and broadens the application fields of the high-purity low-arsenic hydroxyethylidene diphosphonic acid.
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Paragraph 0019-0028
(2017/04/11)
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- METHOD FOR THE SYNTHESIS OF ETHANE-1-HYDROXY-1,1-DIPHOSPHONIC ACID
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The present invention is related toa method for the synthesis of ethane-1-hydroxy-1,1-diphosphonic acid or its salt which includes the steps of reacting tetraphosphorus hexaoxideand acetic acid under controlled reaction conditions; hydrolyzing the formed ethane-1-hydroxy-1,1-diphosphonic acid condensates to form ethane-1-hydroxy-1,1-diphosphonic acid; further processing the ethane-1-hydroxy-1,1-diphosphonic acid solution. The process according to the method of the present invention is highly controllable and further is characterized by a high selectivity.
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Page/Page column 24
(2015/05/06)
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- Microwave-assisted efficient synthesis of bisphosphonate libraries: A useful procedure for the preparation of bisphosphonates containing nitrogen and sulfur
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Microwave-assisted rapid and efficient procedure for the synthesis of bisphosphonate and their libraries is described in solvent-free medium. Bisphosphonates having nitrogen and sulfur are synthesized following this new procedure. This procedure is simple and can be useful for the generation of compound libraries of a class of bone-resorptive inhibitors such as N- and N-, S- containing bisphosphonates.
- Lenin, Racha,Raju, Rallabandi Madusudan,Rao, Divvela V. N. Srinivasa,Ray, Uttam Kumar
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p. 1624 - 1629
(2013/07/26)
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- A study of the reaction of phosphorus trichloride with paraformaldehyde in the presence of carboxylic acids
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We investigated the mechanism of the reaction of paraformaldehyde with phosphorus trichloride in the presence of carboxylic acids (acetic, propanoic, and formic). Our results revealed that bisphosphonic acids were obtained without the use of water. The structures of the reaction products were studied by 1D and 2D homonuclear and heteronuclear 1H-, 13C-, 31P- NMR spectroscopy. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional tables.]
- Troev,Todorov,Naydenova,Mitova,Vassilev
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p. 1147 - 1155
(2013/09/23)
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- Non-hydrolysable analogues of inorganic pyrophosphate as inhibitors of hepatitis C virus RNA-dependent RNA-polymerase
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Inorganic pyrophosphate (PPi) is the product of the polymerization reaction catalyzed by DNA-and RNA-polymerases. A number of novel non-hydrolsable PPi analogues was synthesized; some of them inhibited the polymerization reaction catalyzed by hepatitis C virus RNA-dependent RNA-polymerase (NS5B). A new pharmacophore based on a non-hydrolysable methylenediphosphonate backbone has been developed. The structure-activity relationship analysis of 12 bisphosphonates is presented and the structural features crucial for NS5B polymerase activity inhibition are stated. Pleiades Publishing, Ltd., 2012.
- Yanvarev,Korovina,Usanov,Kochetkov
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experimental part
p. 224 - 229
(2012/08/27)
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- Process for producing biphosphonic acids and forms thereof
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Disclosed herein is a process for producing bisphosphonic acids and salts thereof. The process comprising reacting a carboxylic acid of Formula [I] with phosphorous acid and halophosphorus compound in the presence of a solvent selected from aliphatic hydrocarbon or water miscible cyclic ether. Further, the present invention also provides novel forms of bisphosphonic acids and process for preparation thereof.
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Page/Page column 4-5
(2009/12/27)
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- Amidoalkylation of phosphorus trichloride with acetamide and alkyl oxocycloalkanecarboxylates
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The course of the reaction between phosphorus trichloride, acetamide, and ethyl oxoalkanecarboxylates was studied in terms of the production of side-products. When alkyl 2-oxocycloalkanecarboxylates were used as substrates, together with the expected prod
- Ziora, Zyta,Kafarski, PaweL
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experimental part
p. 1047 - 1053
(2009/12/03)
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- PROCESS FOR PRODUCING BISPHOSPHONIC ACIDS AND FORMS THEREOF
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Disclosed herein is a process for producing bisphosphonic acids and salts thereof. The process comprising reacting a carboxylic acid of Formula [I] with phosphorous acid and halophosphorus compound in the presence of a solvent selected from aliphatic hydrocarbon or water miscible cyclic ether. Further, the present invention also provides novel forms of bisphosphonic acids and process for preparation thereof.
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Page/Page column 12-13
(2008/06/13)
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- Biphosphonate conjugates and methods of making and using the same
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The present invention is directed to particular bisphosphonate compounds, and in particular, to bisphosphonate conjugates that are useful in the treatment of soft tissues surrounding bone and bone-related diseases, such as bone cancer and osteoporosis.
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- Bisphosphonate derivatives, their preparations and uses
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The present invention relates to derivatives of 1-hydroxymethylene-1,1-bisphosphonic acid, the pharmaceutical compositions comprising them, and their application in therapeutics, particularly for the treatment of cancerous tumors. It is also directed to a methods of preparation of such derivatives.
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- METHOD FOR PRODUCTION ON THE SPOT OF A DISINFECTANT PERACETIC ACID SYSTEM
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A method for preparing a disinfectant and sterilizing peracetic acid solution, comprising the production just before use of peracetic acid by mixing an activator (HP) with a parent mixture.
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- Process for the production of an aqueous monoester peroxycarboxylic acid solution, the solution obtainable by this process, and its use as disinfectant
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Process for the production of an aqueous monoester peroxycarboxylic acid solution by reaction of a peroxygen compound with at least one dicarboxylic acid and with at least one alcohol optionally in the presence of an acid catalyst. Aqueous monoester peroxycarboxylic acid solution obtainable by this process. Use of the aqueous monoester peroxycarboxylic acid solution as disinfectant.
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- Bisphosphonate conjugates and methods of making and using the same
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The present invention is directed to particular bisphosphonate compounds, and in particular, to bisphosphonate conjugates that are useful in the treatment of soft tissues surrounding bone and bone-related diseases, such as bone cancer and osteoporosis.
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- A mild and efficient one-pot synthesis of 1-hydroxymethylene-1,1-bisphosphonic acids. Preparation of new tripod ligands
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A simple and efficient one-pot procedure for synthesis of 1-hydroxymethylene-1,1-bisphosphonic acids by reaction of acyl chlorides and tris(trimethylsilyl)phosphite is described. This method was applied to the synthesis of new phosphonated chelating tripod ligands.
- Lecouvey, Marc,Mallard, Isabelle,Bailly, Théodorine,Burgada, Ramon,Leroux, Yves
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p. 8475 - 8478
(2007/10/03)
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- Bisphosphonate conjugates and methods of making and using the same
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The present invention is directed to particular bisphosphonate compounds, and in particular, to bisphosphonate conjugates that are useful in the treatment of soft tissues surrounding bone and bone-related diseases, such as bone cancer and osteoporosis.
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- Method for production on the spot of a disinfectant peracetic acid system
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A method for preparing a disinfectant and sterilizing peracetic acid solution, comprising the production just before use of peracetic acid by mixing an activator (HP) with a parent mixture.
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- Regimen for treatment or prophylaxis of osteoporosis
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Methods for treating or preventing osteoporosis, including regimens for intermittent dosing of bone resorption inhibiting polyphosphonate compound or a pharmaceutically acceptable salt or ester of any such compound.
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- Oral compositions
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Oral compositions providing antitartar and antigingivitis benefits containing an antitartar agent and a stannous salt.
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- PHOSPHONYLATION BY TETRAPHOSPHORUS HEXOXIDE
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The general usefulness of P4O6 as starting material for the preparation of inorganic and organic phosphorus compounds is demonstrated by reactions of P4O6 with nucleophilic and electrophilic compounds.
- Schuelke, Ulrich
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p. 623 - 626
(2007/10/02)
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- Regimen for treating osteoporosis
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A method for treating or preventing osteoporosis utilizing a cyclic regimen comprising alternating for two or more cycles the administration of a bone resorption inhibiting polyphosphonate and a no treatment (rest) period. Further disclosed is a kit for use in implementing this method of treatment.
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- Stable peroxy-containing microbicides
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Stable peroxy-containing concentrates useful for the production of microbicidal agents consisting essentially of 0.5% to 20% by weight of peracetic or perpropionic acid or their precursors, 25% to 40% by weight of H2 O2, 0.25% to 10% by weight of an organic phosphonic acid capable of sequestering bivalent metal cations and their water-soluble acid salts, 0 to 5% by weight of anionic surface-active compounds of the sulfonate and sulfate type, Remainder: water.
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- Oral composition for calculus retardation
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Oral compositions, such as toothpaste, mouthwash, and the like, containing certain polyphosphonic acids and their salts which retard dental calculus formation without damaging tooth structure.
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- Process for the manufacture of acylation products of phosphorous acid
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A process for the manufacture of acylation products of a phosphorous acid having at least two phosphorus atoms in their molecules, which consists essentially of the steps of mixing one mol of phosphorus trichloride with from 2.5 to 3 mols of a mixture of carboxylic acid plus water, said acid being selected from the group consisting of an aliphatic monocarboxylic acid having 2 to 12 carbon atoms and benzoic acid; the share of said water in said mixture being from 1.2 to 1.5 mols; at a temperature up to 80° C; heating the reaction blend thus obtained, after completing of said mixing to 100° C to 160° C and recovering said acylation products.
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