WO2012123378A1 - Procédé de production et d'utilisation de cyanoguanidine et de cyanamide - Google Patents

Procédé de production et d'utilisation de cyanoguanidine et de cyanamide Download PDF

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Publication number
WO2012123378A1
WO2012123378A1 PCT/EP2012/054171 EP2012054171W WO2012123378A1 WO 2012123378 A1 WO2012123378 A1 WO 2012123378A1 EP 2012054171 W EP2012054171 W EP 2012054171W WO 2012123378 A1 WO2012123378 A1 WO 2012123378A1
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WO
WIPO (PCT)
Prior art keywords
cyanamide
cyanoguanidine
ammonia
calcium
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2012/054171
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English (en)
Inventor
Robert Kurt Graupner
J. Dustin Hultine
James Alden Van Vechten
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Puregeneration UK Ltd
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Puregeneration UK Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Puregeneration UK Ltd filed Critical Puregeneration UK Ltd
Publication of WO2012123378A1 publication Critical patent/WO2012123378A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/02—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of guanidine from cyanamide, calcium cyanamide or dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
    • C01C3/00—Cyanogen; Compounds thereof
    • C01C3/16—Cyanamide; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
    • C01C3/00—Cyanogen; Compounds thereof
    • C01C3/16—Cyanamide; Salts thereof
    • C01C3/18—Calcium cyanamide
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05C—NITROGENOUS FERTILISERS
    • C05C9/00—Fertilisers containing urea or urea compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/02—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/24—Mixing, stirring of fuel components
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/54—Specific separation steps for separating fractions, components or impurities during preparation or upgrading of a fuel
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals

Definitions

  • the present invention is concerned with novel methods of producing cyanoguanidine, which is also known as dicyandiamide, and cyanamide.
  • cyanoguanidine which is also known as dicyandiamide, and cyanamide.
  • the present application is also concerned with the use of cyanoguanidine and cyanamide as a fuel.
  • cyanamide-based compositions means a composition comprising cyanamide, calcium cyanamide, cyanoguanidine or dicyanoguanidine and optionally one or more other compounds related to cyanamide, for example guanidine, urea and guanylurea.
  • Urea, guanidine, and guanylurea are related to calcium cyanamide because they are products of the partial hydrolysis of cyanoguanidine and urea is a product of the partial hydrolysis of hydrogen cyanamide.
  • FBG solid free-base guanidine
  • cyanoguanidine for example for use directly as a transportation fuel or fertiliser.
  • a rotary arc reactor is used.
  • the coal suitably dried powdered coal as discussed above, can be injected into the rotary arc reactor.
  • the present inventors have found that the impurities will be released into the CO gas stream (CO being the reaction product of calcium oxide and carbon) and can be condensed out into potentially valuable commodities.
  • the elevated temperature is provided by an electric arc reactor, suitably a rotating arc reactor.
  • an electric arc reactor suitably a rotating arc reactor.
  • other methods of supplying intense localized heat may also be used.
  • a non-rotating arc would work, for example.
  • a solar furnace could be used to heat the carbon and metal oxide to produce a melt that yields metal carbide, by passing the carbon/metal oxide mixture through the focal point of a solar furnace.
  • a microwave arc/plasma could also be used.
  • a method to produce transportation fuel comprising: a) mixing a source of carbon and of hydrogen with calcium oxide and nitrogen gas with a practical minimum of free oxygen and,
  • step b) The method of any one of paragraphs 96) to 127) wherein at least some of the free 5 hydrogen gas that is produced in step b) is reacted with carbon dioxide according to the known art Bosch Reaction to produce carbon and water, this carbon being added to the supply of source carbon and hydrogen materials.
  • acetylene produced is partially oxidized to produce carbon black that is added to the supply of carbon material.
  • a catalyst that may be a mixture of metallic zinc and vanadium pentoxide, to form a mixture of ammonia and carbon dioxide being used as a fuel.
  • step (b) oxidizing the ammonia formed in step (a) to form water and nitrogen generating energy.
  • ammonium hydroxide calcium cyanamide, magnesium cyanamide, zinc cyanamide, calcium hydroxide, magnesium hydroxide, zinc hydroxide, hydrogen cyanamide, cyanoguanidine, guanidine, ammonium carbamate, guanylurea, urea, calcium carbide, magnesium carbide, zinc carbide, water, and a combination thereof.
  • Fig. 7 shows a schematic description of a rotary arc component of this apparatus by means of valves; wherein a) the reagents calcium oxide and carbon are introduced to the rotary arc and reflector assembly so that a constant pressure is maintained within the rotating arc and reflector components of this apparatus and b) as the solid (calcium carbide) product of this pressurized compartment is separated and passed through valves to a fluidized bed maintained as a temperature controlled gradient for synthesis of the cyanamide-based composition.
  • Fig. 8 shows a schematic description of a rotary arc component of this apparatus by means of valves; wherein a) the reagents calcium oxide and methane are introduced to the rotary arc and reflector assembly so that a constant pressure is maintained within the rotating arc and reflector components of this apparatus and b) as the solid (calcium carbide) product of this pressurized compartment is separated and passed through valves to a fluidized bed maintained as a temperature controlled gradient for synthesis of the cyanamide-based composition.
  • Fig. 12 shows a schematic flowchart as a means to safely store electrical energy in the form of chemical energy by using the reagents nitrogen and methane and where off-site electrical power can be used to synthesize cyanoguanidine.
  • Fig. 13 shows a schematic flowchart as a means to safely store electrical energy in the form of chemical energy by using the reagents nitrogen and carbon and where on-site or stranded electrical power can be automatically switched from power grid or source to rotary arc and synthesis of calcium cyanamide.
  • Fig. 12 shows a schematic flowchart as a means to safely store electrical energy in the form of chemical energy by using the reagents nitrogen and carbon and where on-site or stranded electrical power can be automatically switched from power grid or source to rotary arc and synthesis of calcium cyanamide.
  • FIG. 17 shows a schematic flowchart where synthesized cyanamide-based compositions made from a metal oxide, a carbon source and electrical energy can be stored and transported in the form of chemical energy that in turn may be used for multiple fuel and multiple nitrogen-based commodity applications.
  • Fig. 18 shows a schematic flowchart illustrating the production of cyanoguanidine using a rotary arc.
  • the oxidation of hydrogen to form water may be performed by combusting the hydrogen in an engine.
  • the oxidation of ammonia to form nitrogen and water may be performed by combusting the ammonia in an engine.
  • the ammonia and hydrogen may be oxidized in an ammonia fuel cell and a hydrogen fuel cell, respectively.
  • fuel cells include high temperature fuel cells such as solid oxide fuels cell and molten carbonate fuel cells, and relatively lower temperature fuel cells such as alkaline-fuel cells, PEM fuel cells and phosphoric acid fuel cells.
  • the combustion of ammonia to form water and nitrogen may also lead to the formation of nitrogen oxides which have the general formula N x O y ., such as, for example, NO or N0 2 . Elevated levels of the nitrogen oxides are obtained depending upon reaction conditions.
  • the nitrogen oxides are pollutants and their emission is regulated.
  • An advantage of using ammonia as the fuel in the present invention is that pollution caused by the nitrogen oxides may be abated or eliminated by reaction of unburned ammonia exiting the combustion chamber with the nitrogen oxides in a post combustion reactor.
  • the unburned ammonia acts as a reducing agent to convert nitrogen oxides into molecular nitrogen.
  • ammonia generated from the reaction of cyanoguanidine with water is oxidized or combusted to produce energy. While pure ammonia has also been proposed as a fuel, the use of pure ammonia has several drawbacks. Ammonia is a gas at room temperature and requires high pressure to liquefy. It is a corrosive substance which in large quantities may cause respiratory problems and even death. While it is possible to dissolve ammonia in water to produce a fuel, the resulting fuel has a pH of over 1 1 and a strong ammonia odor. Finally, ammonia has a relatively low energy density compared to gasoline and other alternative fuels.
  • Fig. 1 The second preferred practice for the production of the dicyandiamide or cyanamide fuel is illustrated in Fig. 1 as "option #2".
  • the nitrogen gas is not introduced until after the electric arc has driven Reaction 1 to make CaC 2 at temperatures of about 2000 °C (see Li et al., op. cit.). This allows the reaction with nitrogen to proceed at the optimum temperature for formation of calcium cyanamide and avoids the energy needed to heat the nitrogen gas (in the presence of carbon) to such a temperature and the precautions needed to deal properly with the possible formation of HCN gas.
  • the nitrogen gas is introduced optionally additional heating supplied to maintain the reactants at the desired temperature for a longer time to drive reaction (8) to form CaCN 2 . From thereon the practice is as described above for "option #1".

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

La présente invention se rapporte à un procédé de production d'une composition comprenant de la cyanoguanidine. Le procédé consiste à: a) utiliser une source d'énergie pour mettre en réaction un oxyde métallique avec une source de carbone afin de produire un carbure métallique finement divisé à une température élevée, et mettre immédiatement en réaction le carbure métallique finement divisé à chaud avec de l'azote gazeux pour former un cyanamide métallique. Dans certains modes de réalisation, le procédé comprend l'étape: b) de mise en réaction du cyanamide de métal associé à un quelconque carbure métallique intact avec de l'eau pour décomposer le carbure métallique en acétylène et ses composés dérivés et en hydroxyde métallique. De plus, de l'énergie peut être tirée de la réaction par c) combustion de l'acétylène et de ses composés dérivés pour libérer de l'énergie. En outre un hydroxyde métallique peut être récupéré du processus par d) séparation du cyanamide métallique et de l'hydroxyde métallique pour recyclage dans le processus de production. La cyanoguanidine peut ensuite être utilisée, par exemple, comme engrais.
PCT/EP2012/054171 2011-03-11 2012-03-09 Procédé de production et d'utilisation de cyanoguanidine et de cyanamide Ceased WO2012123378A1 (fr)

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
US201161464980P 2011-03-11 2011-03-11
US61/464,980 2011-03-11
US201161517521P 2011-04-21 2011-04-21
US61/517,521 2011-04-21
US201161519574P 2011-05-25 2011-05-25
US61/519,574 2011-05-25
US201161520236P 2011-06-06 2011-06-06
US61/520,236 2011-06-06
US201161571289P 2011-06-24 2011-06-24
US61/571,289 2011-06-24

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WO2012123378A1 true WO2012123378A1 (fr) 2012-09-20

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PCT/EP2012/054173 Ceased WO2012123380A2 (fr) 2011-03-11 2012-03-09 Procédé de production et d'utilisation de cyanoguanidine et de cyanamide

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Cited By (11)

* Cited by examiner, † Cited by third party
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CN107500315A (zh) * 2017-09-06 2017-12-22 山东益丰生化环保股份有限公司 一种单氰胺溶液的清洁制备方法
WO2018231047A1 (fr) * 2017-06-15 2018-12-20 Petroliam Nasional Berhad (Petronas) Système et procédé de dosage du mercure dans un flux d'hydrocarbures
CN110228817A (zh) * 2019-06-10 2019-09-13 陕西师范大学 一种制备纳米氰氨化铟粉末的方法
CN110775988A (zh) * 2019-11-26 2020-02-11 山东益丰生化环保股份有限公司 一种单氰胺的制备方法
WO2020210252A1 (fr) * 2019-04-12 2020-10-15 Hultine Dustin J Synthèse intégrée de produits chimiques de marchandises à partir de déchets plastiques
CN113224302A (zh) * 2021-05-08 2021-08-06 陕西科技大学 一种利用原位自催化实现石墨化碳包覆的氰胺化铁材料及其应用
CN113224303A (zh) * 2021-05-08 2021-08-06 陕西科技大学 一种利用原位自催化实现石墨化碳包覆的氰胺化铁材料的制备方法
US11591533B1 (en) 2022-01-05 2023-02-28 J. Dustin Hultine Removal of hydrogen sulfide and other acids from hydrocarbon gas
WO2024050226A3 (fr) * 2022-08-29 2024-04-18 Thg, Llc Engrais issu de composés de cyanamide hydrolysés
WO2024124121A1 (fr) * 2022-12-09 2024-06-13 Thg, Llc Recyclage de matériaux à teneur réduite en carbone
US20240188566A1 (en) * 2021-03-19 2024-06-13 Arxada, LLC Biocidal Composition and Method

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ES2957422B2 (es) * 2022-06-06 2024-06-10 Hydrogen & Innovation S L Procedimiento de eliminacion de compuestos nitrogenados

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