EP1135392A2 - Procede de preparation de tetraaza macrocycles pontes transversalement - Google Patents

Procede de preparation de tetraaza macrocycles pontes transversalement

Info

Publication number
EP1135392A2
EP1135392A2 EP99963923A EP99963923A EP1135392A2 EP 1135392 A2 EP1135392 A2 EP 1135392A2 EP 99963923 A EP99963923 A EP 99963923A EP 99963923 A EP99963923 A EP 99963923A EP 1135392 A2 EP1135392 A2 EP 1135392A2
Authority
EP
European Patent Office
Prior art keywords
hgand
tetraaza
macrocychc
formula
mixtures
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
EP99963923A
Other languages
German (de)
English (en)
Inventor
George Douglas Ii Hiler
Christopher Mark Perkins
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22332328&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP1135392(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP1135392A2 publication Critical patent/EP1135392A2/fr
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
    • C07F13/005—Compounds without a metal-carbon linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water

Definitions

  • the present invention relates to an improved process for preparing cross-bridged tetraaza macrocycles, said macrocycles suitable as ligands for use m preparing transition metal complexes
  • the present invention provides a process which is well suited for use in industrial and other commercial preparations of the herein described crossed-b ⁇ dged macrocycles.
  • Tetraaza macrocyclics for example, cyclam
  • Tetraaza macrocyclics have been prepared in numerous ways, however, there is a paucity of information relating to the preparation of cross-bridged tetraaza macrocyclics inter aha bis N-substituted tetraaza macrocyclics inter alia 5,12 dialkyl 1,5,8,12- tetraaza-b ⁇ cyclo[6.6.2]hexadecanes which have recently found wide applicability as ligands especially in the area of transition metal catalysts inter alia bleach catalysts.
  • WO 98/39335 Al discloses a rational procedure for preparing cross bridged macropolycychc ligands which is amenable to high yields necessary for industrial scale-up.
  • the reductive ring cleavage step which results in bicyclo bridged-ring formation utilizes a borohyd ⁇ de reducing agent.
  • This type of reducing agent can place constraints on the formulator. For example, the need to break up the amine/borohyd ⁇ de complex du ⁇ ng work-up and the proper recovery and disposal of boron waste products adds cost to the process. Also, if excess borohyd ⁇ de is needed, this requires neutralization which involves the use of acid and the evolution of large quantities of hydrogen gas.
  • a first aspect of the present invention relates to a process for preparing a tetraaza macrocychc hgand having the formula:
  • each R is independently Cj-Cg linear or branched alkyl, -(CH 2 ) x C0 2 M, and mixtures thereof, preferably both of the R units are not methyl; M is hydrogen or a salt forming cation; x is from 1 to 6; each index n is independently from 0 to 3; said process comprising the steps of a) hydrogenat g a tetraaza macrocychc hgand precursor having the formula:
  • X is an anion which provides charge neutrality, with from about 1 ppm of a transition metal hydrogenation catalyst at a pH of at least 8 to form a tetraaza macrocychc hgand; and b) optionally isolating said hgand.
  • the present invention relates to the catalytic hydrogenation of tetraaza macrocycles having the formula: wherein the covalent bond between the N-substituted quaternary ring nitrogen and the bridging carbon is broken and a cross-bridged macrocychc hgand having the formula:
  • each R is independently Cj-C 8 linear or branched alkyl, - (CH 2 ) s C0 2 M, and mixtures thereof, preferably both of the R units are not methyl; more preferably one R unit is methyl and the other R unit is selected from the group consisting of ethyl, propyl, butyl, pentyl, hexyl. and mixtures thereof; of the methyl/alkyl R unit mixtures preferably one R is methyl and the other R is ethyl or propyl.
  • a most preferred hgand consists of a unit wherein one R unit is methyl and the other R unit is ethyl.
  • a preferred gand is a macrocychc ring wherein each R unit is ethyl.
  • M is hydrogen or a salt forming cation, non-limiting examples of which are sodium, potassium, calcium, ammonium.
  • R is -(CH 2 ) x C0 2 M the index x has the value from 1 to about 6. preferably x is 1.
  • the index n defines the size of the macrocychc ring. The index n has the value of from 0 to about 3.
  • a preferred macrocychc ring has one opposite set of n indices equal to 1 and the other set of n indices equal to 0 as in the general formula: wherein R is the same as defined herein above.
  • Preferred ligands according to the present invention comprise R unit pairs which are selected from the group consisting of methyl and ethyl, di ethyl, methyl and propyl, ethyl and propyl, methyl and butyl, ethyl and butyl, and mixtures thereof.
  • the starting materials for the process of the present invention are tetraaza macrocychc hgand precursors, or alternatively, bis-quaternary as tetracycles, having the formula-
  • X is an anion which serves to provide electronic neutrality to the bis-quaternary cis tetracycle.
  • electroactive neutrality refers to "a sufficient amount of an anionic species which satisfies the molecular charge balance requirements" and that a mixture of mono-, di-, tri-. etc. electronic species may be use herein.
  • X preferably has unit negative charge, for example, halogen, tosylate, methylsulfate, ethylsulfate.
  • X may have more than one negative charge, for example, sulfate, in which case the formulator requires only half the amount necessary when using a unit negative-charged anion.
  • Preferred X is chloride, bromide, iodide, sulfate, ethyl sulfate, methyl sulfate, tosylate, mesylate, triflate, and mixtures thereof.
  • Step (a) comprises the reductive cleavage via catalytic hydrogenation as outlined in the following scheme'
  • Step (a) is conducted in the presence of a catalyst, preferably a supported catalyst.
  • a catalyst preferably a supported catalyst.
  • catalysts include platinum on carbon, palladium on carbon (Pd/C), palladium hydroxide on carbon (Pd(OH) 2 /C), rhodium on carbon (Rh/C), Raney nickel, and mixtures thereof.
  • a preferred catalyst is Pd(0H) /C.
  • the supported catalysts may comprise from about 1% to about 50% by weight of transition metal, however, the pure metal, i.e. palladium, can be used without the need for a "support", i.e., carbon.
  • catalytic amount of catalyst is sufficient to provide the reduction of step (a).
  • the term catalytic amount is defined as "from about 1 ppm of a 5% by weight transition metal catalyst".
  • the formulator, due to poisoning of the catalyst surface by reaction products may use more than a catalytic amount of a catalyst.
  • the amount of catalyst used in step (a) of the present invention is preferably from about 10 ppm of a catalyst which contains from about 5% to 50% by weight, of a transition metal, more preferably from about 100 ppm, yet more preferably from about 0.1% by weight, of a transition metal supported catalyst
  • a reaction solution which comprises 0.1% by weight, of a transition metal supported catalyst, said catalyst comprising, for example, 10% by weight of palladium on carbon, has 0.01% transition metal or 100 ppm transition metal present.
  • step (a) of the present invention need only be enough to sufficiently saturate the catalyst surface, preferably the hydrogen pressure is from 200 psi, more preferably from 400 psi, most preferably from 800 psi to about 2000 psi, more preferably to 1000 psi.
  • Step (a) of the present process can be conducted at a temperature of from 20° C, preferably from about 40° C, more preferably from about 60° C to about 100° C, preferably to about 90° C, more preferably to about 80° C, most preferably to about 65° C.
  • the pH under which Step (a) must be conducted is at least 8, preferably at least 10, more preferably at least about 11.
  • the base which is used to adjust the pH is in the form of an aqueous solution.
  • Preferred bases are selected from the group consisting of potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, and mixtures thereof. As a non-limiting example, it is satisfactory to use a sufficient amount of 1 M (molar) aqueous base to adjust the pH to the required level.
  • a convenient and preferred base is potassium carbonate.
  • Step (a) can be conducted in the presence of a solvent other than water, or m the absence of water.
  • a mixture of a suitable solvent and water is a suitable means for conducting the hydrogenation process of the present invention.
  • water is absent, sufficient base must be present to stabilize the transition state of the reactants and products during hydrogenation.
  • solvents include methanol, ethanol, n- propanol, isopropanol, N.N-dimethyl formamide, n-butanol. iso-butanol, tert-butanol, and mixtures thereof; preferred solvents are selected from the group consisting of ethanol, n- propanol, N,N-d ⁇ methyl formamide, and mixtures thereof.
  • the ratio of said volume of an aqueous base, to said solvent is from about 1 : 10 to about 1 : 1, preferably the ratio of the volume of aqueous base to solvent is 1 :4. It is desirable, but not a requirement, that the aqueous base and solvent form a two phase system.
  • Step (b) is an isolation step.
  • this step involves filtration of the reaction solution to remove the catalyst.
  • this step may comprise a neutralization step, however, the product can be isolated or removed from the reaction matrix in any manner which the formulator desires.
  • the reaction solution containing the cross- bridged hgand is filtered to remove the catalyst to form a crude filtrate.
  • This crude filtrate can be neutralized or the tetraaza macrocychc hgand can be isolated by extraction or crystallization directly from the preferably aqueous solution.
  • Steps (a) and (b) and any optional extensions thereto may be suitably adapted for either batch processes or continuous processes, for example, continuous flow processes.
  • the process of the present invention may comp ⁇ se other optional steps as deemed necessary and/or desirable by the formulator. These optional steps may include but are not limited to, pre-saturation of the catalyst with hydrogen, drawing a vacuum on the system, and recovery of the catalyst and solvents.
  • the ligands formed by the process of the present invention are converted into manganese containing transition metal catalysts in a subsequent, however optional, process step
  • the bleach catalysts comprise a central manganese atom and a cross-branched hgand formed by the process of the present invention.
  • the final bleach catalyst may comprise one or more other compatible ligands inter aha chlorine atom.
  • the preferred catalysts are suitable as bleaching agents.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un ligand tétraaza macrocyclique de formule (I) dans laquelle chaque R est, de manière indépendante, un alkyle linéaire C1-C8 ou un alkyle ramifié (CH2)xCO2M, et des mélanges de ce ligand, pourvu que les deux R ne soient pas des groupes méthyle, M est un hydrogène ou un cation formant un sel, x prend les valeurs de 1 à 6, chaque indice n prend, de manière indépendante, les valeurs de 1 à 3. Ce procédé consiste à mettre en contact un précurseur tétracyclique cis di-quaternaire avec de l'hydrogène en présence d'un catalyseur au palladium dans une solution aqueuse de pH au moins égal à environ 10 et à une température comprise entre environ 40 °C et environ 100°C.
EP99963923A 1998-11-30 1999-11-18 Procede de preparation de tetraaza macrocycles pontes transversalement Ceased EP1135392A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11030998P 1998-11-30 1998-11-30
US110309P 1998-11-30
PCT/US1999/027316 WO2000032601A2 (fr) 1998-11-30 1999-11-18 Procede de preparation de tetraaza macrocycles pontes transversalement

Publications (1)

Publication Number Publication Date
EP1135392A2 true EP1135392A2 (fr) 2001-09-26

Family

ID=22332328

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99963923A Ceased EP1135392A2 (fr) 1998-11-30 1999-11-18 Procede de preparation de tetraaza macrocycles pontes transversalement

Country Status (5)

Country Link
EP (1) EP1135392A2 (fr)
JP (1) JP2002531457A (fr)
AU (1) AU2026100A (fr)
CA (1) CA2348893A1 (fr)
WO (1) WO2000032601A2 (fr)

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JP2025530749A (ja) 2022-09-02 2025-09-17 ダニスコ・ユーエス・インク 洗剤組成物及びそれに関連する方法
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CA2348893A1 (fr) 2000-06-08
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JP2002531457A (ja) 2002-09-24

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