WO1997000263A1 - Method for manufacturing cobalt catalysts - Google Patents

Method for manufacturing cobalt catalysts Download PDF

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Publication number
WO1997000263A1
WO1997000263A1 PCT/US1996/001086 US9601086W WO9700263A1 WO 1997000263 A1 WO1997000263 A1 WO 1997000263A1 US 9601086 W US9601086 W US 9601086W WO 9700263 A1 WO9700263 A1 WO 9700263A1
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Prior art keywords
formula
unsubstituted
cobalt
substituted
reacting
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PCT/US1996/001086
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French (fr)
Inventor
Christopher Mark Perkins
Mark Robert Sivik
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The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP9503028A priority Critical patent/JPH11509529A/en
Priority to CA002224462A priority patent/CA2224462C/en
Priority to AT96903702T priority patent/ATE192453T1/en
Priority to DE69608102T priority patent/DE69608102T2/en
Priority to EP96903702A priority patent/EP0832088B1/en
Priority to AU47700/96A priority patent/AU4770096A/en
Publication of WO1997000263A1 publication Critical patent/WO1997000263A1/en

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    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/06—Cobalt compounds
    • C07F15/065—Cobalt compounds without a metal-carbon linkage

Definitions

  • T y vriierein M ligand is selected from substituted and unsubstituted C1-C30 carboxylic acids having the formula: RC(O)O-.
  • catalysts are particularly useful in bleach-containing consumer compositions, especially automatic dishwashing detergents and laundry detergents comprising bleach.
  • Cobalt catalysts are well known, as are a variety of methods for manufacturing them. Most synthesis methods, however, are directed simply to methods effective for obtaining experimental quantities for academic studies. These are described, for example, in M. L. Tobe, "Base Hydrolysis of Transition-Metal Complexes", Adv. Inorg. Bioinorg. Mech.. (1983), 2, pages 1-94; J. Chem. Ed. (1989), 66 (12), 1043-45; “The Synthesis and Characterization of Inorganic Compounds", W.L. Jolly (Prentice-Hall; 1970), pp. 461-3; Inorg. Chem.. .18, 1497- 1502 (1979); Inorg. Chem..
  • cobalt catalysts for use in consumer products, however, it is necessary that the cobalt catalysts be prepared in large quantities by the most cost effective manner with the highest possible purity. It has been discovered by the present invention that cobalt catalysts containing carboxylate ligands can be prepared on an industrially useful scale by the present process. BACKGROUND ART
  • the present invention relates to methods for manufacturing cobalt complexes having the formula:
  • T is one or more counteranions present in a number y to obtain a charge-balanced salt
  • T are selected from the group consisting of chloride, iodide, 13", formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg-, BF4-, B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof
  • y is 1 or 2; with concentrated ammonium hydroxide and ammonium chloride; followed by
  • step (b) reacting the product of step (a) with an oxidizing agent selected from the group consisting of oxygen, hydrogen peroxide, and mixtures thereof; followed by
  • step (c) reacting the product of step (b) with a carboxylic acid anhydride of the formula:
  • each R is independently selected from substituted or unsubstituted C1-C30 moieties (preferably both R are the same);
  • the present invention relates to a method for manufacturing cobalt complexes having the formula:
  • This method comprises the first step of reacting a cobalt (II) salt having the formula:
  • T is one or more counteranions present in a number y to obtain a charge-balanced salt
  • T are selected from the group consisting of chloride, iodide, 13", formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg", BF4", B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof
  • y is 1 or 2; with concentrated ammonium hydroxide and ammonium chloride (preferably at least 20%, more preferably at least 25%, and typically between 28-32% solutions of concentrated ammonium hydroxide).
  • This step is typically conducted at room temperature; preferred temperatures are below about 90 °C, more preferably below 80 °C. Preferred is to use from about 5.0 to about 10.0 equivalents, more preferably from about 5.0 to about 5.5 equivalents, of ammonium hydroxide in a concentrated aqueous solution so as to minimize the volume of water present during the reaction.
  • This first step is followed by a step whereby the product of the first step is reacted with an oxidizing agent selected from the group consisting of an oxidizing source such as oxygen and, especially, hydrogen peroxide (preferably at concentrations of at least about 30% and more preferably at least about 50% by weight).
  • an oxidizing agent selected from the group consisting of an oxidizing source such as oxygen and, especially, hydrogen peroxide (preferably at concentrations of at least about 30% and more preferably at least about 50% by weight).
  • This step is also typically conducted at room temperature; preferred temperatures are below about 90 °C, more preferably below 80 °C.
  • This reaction step is then followed by reacting the product of the previous step with a carboxylic acid anhydride ofthe formula: RC(O)O(O)CR wherein each R is independently selected from substituted or unsubstituted C1-C30 moieties. It is preferred that both R moieties are the same, but mixed anhydrides may be used as desired for the desired cobalt complex being synthesized.
  • Reaction conditions for this step are typically room temperature (preferred temperatures are below about 90 °C, more preferably below 80 °C) for from about 10 to about 60 minutes. Additionally, about 1.0 to about 2.0 equivalents of the ammonium carboxylate salt can be added prior to the addition of the carboxylic acid anhydride to facilitate synthesis ofthe desired cobalt complex.
  • This reaction step is then optionally followed by exchanging the T counterion ofthe prepared cobalt complex with another T counterion. This may be carried out, for example, by treating the complex with an acid (e.g., HCl or HCIO4), or a sa (e.g., NaPF 6 ).
  • an acid e.g., HCl or HCIO4
  • a sa e.g., NaPF 6
  • the mixture is optionally filtered and the cobalt complex is collected.
  • Preferred collection methods include, for example, evaporation to remove the solvent or lyophiiization or precipitation (e.g., by addition of a co-solvent).
  • the cobalt complex collected may be used as is, or further purified or modified for inco ⁇ oration into the desired product or use to be made of the complex. This includes optionally washing the solid product with a suitable solvent, e.g., ethanol, to remove non-cobalt salts.
  • the present invention method preferably is carried out in one reaction vessel without isolation or separation of the intermediate reaction products. However, if desired, one or more of the reaction steps may be conducted in separate reaction vessels, and may be followed or preceeded by optional separation and/or collection steps ofthe intermediate reaction materials.
  • T are selected from the group consisting of chloride, iodide, I3", formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg", BF4", B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof.
  • T can be protonated if more than one anionic group exists in T, e.g., HPO4 2 -, HCO3", H2PO4-, etc.
  • T may be selected from the group consisting of non-traditional inorganic anions such as anionic surfactants (e.g., linear alkylbenzene sulfonates (LAS), alkyl sulfates (AS), alkylethoxysulfonates (AES), etc.) and/or anionic polymers (e.g., polyacrylates, polymethacrylates, etc.).
  • anionic surfactants e.g., linear alkylbenzene sulfonates (LAS), alkyl sulfates (AS), alkylethoxysulfonates (AES), etc.
  • anionic polymers e.g., polyacrylates, polymethacrylates, etc.
  • R is preferably selected from the group consisting of hydrogen and
  • C--C30 (preferably Cj-Cig) unsubstituted and substituted alkyl, C6-C30 (preferably Cg-Cjg) unsubstituted and substituted aryl, and C3-C30 (preferably C5-C18) unsubstituted and substituted heteroaryl, wherein substituents are selected from the group consisting of -NR* 3 , -NR' 4 + , -C(O)OR, -OR', -C(O)NR' , wherein R' is selected from the group consisting of hydrogen and Cj-Cg moieties.
  • Such substituted R therefore include the moieties -(CH2) n OH and -(CH2) n NR'4 + , wherein n is an integer from 1 to about 16, preferably from about 2 to about 10, and most preferably from about 2 to about 5.
  • M are carboxyUc acids having the formula above wherein R is selected from the group consisting of hydrogen, methyl, ethyl, propyl, straight or branched C4-C12 alkyl, and benzyl. Most preferred R is methyl.
  • the M moieties include mono-carboxylates, which are preferred, but more than one carboxylate may be present in the moiety as long as the binding to the cobalt is by only one carboxylate per moiety (in which case the other carboxylate in the M moiety may be protonated or in its salt form).
  • Preferred carboxylic acid M moieties include formic, benzoic, octanoic, nonanoic, decanoic, dodecanoic, malonic, maleic, succinic, adipic, phthalic, 2-ethylhexanoic, naphthenoic, oleic, palmitic, triflate, tartrate, stearic, butyric, citric, acrylic, aspartic, fumaric, lauric, linoleic, lactic, malic, and especially acetic acid. Therefore, most preferred methods use the anhydrides comprising these carboxyUc acids, and preferred anhydrides are the same acids. Most preferred anhydride is acetic anhydride.
  • the preferred cobalt complexes prepared by the present invention are cobalt(m) pentaamineacetate dichloride, i.e. [Co(NH3)5OAc]Cl2 (herein "PAC"); cobalt(m) pentaamineacetate diacetate, i.e. [Co(NH3)5OAc](OAc)2; [Co(NH 3 ) 5 OAc](PF 6 )2; [Co(NH 3 ) 5 OAcj(SO4); and [Co(NH 3 )5OAc](BF 4 )2.
  • PAC cobalt(m) pentaamineacetate dichloride
  • PAC cobalt(m) pentaamineacetate dichloride
  • PAC cobalt(m) pentaamineacetate diacetate
  • the starting cobalt(II) complexes useful herein, the [Co(H2O)g] T y complexes, are commercially available and can be prepared by a variety of methods.
  • the foUowing nonlimiting examples further Ulustrate the method according to the present invention.

Abstract

A method for manufacturing cobalt complexes having the formula: [Co(NH3)5M]Ty, wherein M ligands are selected from substituted and unsubstituted C1-C30 carboxylic acids having the formulas: RC(O)O-; said method comprising reacting cobalt (II) complexes having the formula [Co(H2O)6] Ty (e.g., T is chloride) with concentrated ammonium hydroxide/ammonium chloride, followed by an oxidizing agent (e.g., peroxide), followed by carboxylic acid anhydride of the formula RC(O)O(O)CR.

Description

METHOD FOR MANUFACTURING COBALT CATALYSTS
TECHNICAL FIELD The present invention relates to methods for manufacturing cobalt complexes having the formula:
[Co(NH3)5M] Ty vriierein M ligand is selected from substituted and unsubstituted C1-C30 carboxylic acids having the formula: RC(O)O-.
These catalysts are particularly useful in bleach-containing consumer compositions, especially automatic dishwashing detergents and laundry detergents comprising bleach.
BACKGROUND OF THE INVENTION Cobalt catalysts are well known, as are a variety of methods for manufacturing them. Most synthesis methods, however, are directed simply to methods effective for obtaining experimental quantities for academic studies. These are described, for example, in M. L. Tobe, "Base Hydrolysis of Transition-Metal Complexes", Adv. Inorg. Bioinorg. Mech.. (1983), 2, pages 1-94; J. Chem. Ed. (1989), 66 (12), 1043-45; "The Synthesis and Characterization of Inorganic Compounds", W.L. Jolly (Prentice-Hall; 1970), pp. 461-3; Inorg. Chem.. .18, 1497- 1502 (1979); Inorg. Chem.. 21, 2881-2885 (1982); Inorg. Chem.. 18, 2023-2025 (1979); Inorg. Synthesis. 173-176 (1960); and Journal of Physical Chemistry. 56, 22- 25 (1952). For use in consumer products, however, it is necessary that the cobalt catalysts be prepared in large quantities by the most cost effective manner with the highest possible purity. It has been discovered by the present invention that cobalt catalysts containing carboxylate ligands can be prepared on an industrially useful scale by the present process. BACKGROUND ART
U.S. Patent 4,810,410, to Diakun et al, issued March 7,1989; U.S. 5,246,612, to Van Dijk et al., issued September 21, 1993; U.S. 5,244,594, to Favre et al., issued September 14, 1993; and European Patent Application, Publication No. 408,131, published January 16, 1991 by Unilever NV, see also: U.S. Patent 5,114,611, to Van Kralingen et al, issued May 19, 1992 (transition metal complex of a transition metal, such as cobalt, and a non-macro-cyclic ligand); U.S. Pat. 4,430,243, to Bragg, issued February 7, 1984 (laundry bleaching compositions comprising catalytic heavy metal cations, including cobalt); German Patent Specification 2,054,019, published October 7, 1971 by Unilever N.V. (cobalt chelant catalyst); and European Patent Application Publication No. 549,271, published June 30, 1993 by Unilever PLC (macrocychc organic ligands in cleaning compositions). SUMMARY OF THE INVENTION
The present invention relates to methods for manufacturing cobalt complexes having the formula:
[Co(NH3)5M] Ty wherein the M ligand is selected from substituted and unsubstituted C1-C30 carboxylic acids having the formula:
RC(O)O-; said method comprising the steps of:
(a) reacting a cobalt (II) salt having the formula:
[Co(H2O)6] Ty wherein T is one or more counteranions present in a number y to obtain a charge-balanced salt (preferred T are selected from the group consisting of chloride, iodide, 13", formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg-, BF4-, B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof); and y is 1 or 2; with concentrated ammonium hydroxide and ammonium chloride; followed by
(b) reacting the product of step (a) with an oxidizing agent selected from the group consisting of oxygen, hydrogen peroxide, and mixtures thereof; followed by
(c) reacting the product of step (b) with a carboxylic acid anhydride of the formula:
RC(O)O(O)CR wherein each R is independently selected from substituted or unsubstituted C1-C30 moieties (preferably both R are the same);
(d) optionally, exchanging one T counterion with another T counterion; and (e) collecting the cobalt complex.
All parts, percentages and ratios used herein are expressed as percent weight unless otherwise specified. All documents cited are, in relevant part, incoφorated herein by reference.
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for manufacturing cobalt complexes having the formula:
[Co(NH3)5M] Ty wherein the M ligands are selected from substituted and unsubstituted C\- C30 carboxylic acids having the formulas:
RC(O)O-. This method comprises the first step of reacting a cobalt (II) salt having the formula:
[Co(H2O)6] Ty wherein T is one or more counteranions present in a number y to obtain a charge-balanced salt (preferred T are selected from the group consisting of chloride, iodide, 13", formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg", BF4", B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof); y is 1 or 2; with concentrated ammonium hydroxide and ammonium chloride (preferably at least 20%, more preferably at least 25%, and typically between 28-32% solutions of concentrated ammonium hydroxide). This step is typically conducted at room temperature; preferred temperatures are below about 90 °C, more preferably below 80 °C. Preferred is to use from about 5.0 to about 10.0 equivalents, more preferably from about 5.0 to about 5.5 equivalents, of ammonium hydroxide in a concentrated aqueous solution so as to minimize the volume of water present during the reaction.
This first step is followed by a step whereby the product of the first step is reacted with an oxidizing agent selected from the group consisting of an oxidizing source such as oxygen and, especially, hydrogen peroxide (preferably at concentrations of at least about 30% and more preferably at least about 50% by weight). This step is also typically conducted at room temperature; preferred temperatures are below about 90 °C, more preferably below 80 °C.
This reaction step is then followed by reacting the product of the previous step with a carboxylic acid anhydride ofthe formula: RC(O)O(O)CR wherein each R is independently selected from substituted or unsubstituted C1-C30 moieties. It is preferred that both R moieties are the same, but mixed anhydrides may be used as desired for the desired cobalt complex being synthesized. Reaction conditions for this step are typically room temperature (preferred temperatures are below about 90 °C, more preferably below 80 °C) for from about 10 to about 60 minutes. Additionally, about 1.0 to about 2.0 equivalents of the ammonium carboxylate salt can be added prior to the addition of the carboxylic acid anhydride to facilitate synthesis ofthe desired cobalt complex. This reaction step is then optionally followed by exchanging the T counterion ofthe prepared cobalt complex with another T counterion. This may be carried out, for example, by treating the complex with an acid (e.g., HCl or HCIO4), or a sa (e.g., NaPF6).
At the end of the reaction process, the mixture is optionally filtered and the cobalt complex is collected. Preferred collection methods include, for example, evaporation to remove the solvent or lyophiiization or precipitation (e.g., by addition of a co-solvent). The cobalt complex collected may be used as is, or further purified or modified for incoφoration into the desired product or use to be made of the complex. This includes optionally washing the solid product with a suitable solvent, e.g., ethanol, to remove non-cobalt salts.
The present invention method preferably is carried out in one reaction vessel without isolation or separation of the intermediate reaction products. However, if desired, one or more of the reaction steps may be conducted in separate reaction vessels, and may be followed or preceeded by optional separation and/or collection steps ofthe intermediate reaction materials.
Preferred T are selected from the group consisting of chloride, iodide, I3", formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg", BF4", B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof. Optionally, T can be protonated if more than one anionic group exists in T, e.g., HPO42-, HCO3", H2PO4-, etc. Further, T may be selected from the group consisting of non-traditional inorganic anions such as anionic surfactants (e.g., linear alkylbenzene sulfonates (LAS), alkyl sulfates (AS), alkylethoxysulfonates (AES), etc.) and/or anionic polymers (e.g., polyacrylates, polymethacrylates, etc.). Herein, R is preferably selected from the group consisting of hydrogen and
C--C30 (preferably Cj-Cig) unsubstituted and substituted alkyl, C6-C30 (preferably Cg-Cjg) unsubstituted and substituted aryl, and C3-C30 (preferably C5-C18) unsubstituted and substituted heteroaryl, wherein substituents are selected from the group consisting of -NR*3, -NR'4 +, -C(O)OR, -OR', -C(O)NR' , wherein R' is selected from the group consisting of hydrogen and Cj-Cg moieties. Such substituted R therefore include the moieties -(CH2)nOH and -(CH2)nNR'4+, wherein n is an integer from 1 to about 16, preferably from about 2 to about 10, and most preferably from about 2 to about 5. Most preferred M are carboxyUc acids having the formula above wherein R is selected from the group consisting of hydrogen, methyl, ethyl, propyl, straight or branched C4-C12 alkyl, and benzyl. Most preferred R is methyl. The M moieties include mono-carboxylates, which are preferred, but more than one carboxylate may be present in the moiety as long as the binding to the cobalt is by only one carboxylate per moiety (in which case the other carboxylate in the M moiety may be protonated or in its salt form). Preferred carboxylic acid M moieties include formic, benzoic, octanoic, nonanoic, decanoic, dodecanoic, malonic, maleic, succinic, adipic, phthalic, 2-ethylhexanoic, naphthenoic, oleic, palmitic, triflate, tartrate, stearic, butyric, citric, acrylic, aspartic, fumaric, lauric, linoleic, lactic, malic, and especially acetic acid. Therefore, most preferred methods use the anhydrides comprising these carboxyUc acids, and preferred anhydrides are the same acids. Most preferred anhydride is acetic anhydride.
The preferred cobalt complexes prepared by the present invention are cobalt(m) pentaamineacetate dichloride, i.e. [Co(NH3)5OAc]Cl2 (herein "PAC"); cobalt(m) pentaamineacetate diacetate, i.e. [Co(NH3)5OAc](OAc)2; [Co(NH3)5OAc](PF6)2; [Co(NH3)5OAcj(SO4); and [Co(NH3)5OAc](BF4)2.
The starting cobalt(II) complexes useful herein, the [Co(H2O)g] Ty complexes, are commercially available and can be prepared by a variety of methods. The foUowing nonlimiting examples further Ulustrate the method according to the present invention.
Example 1
Figure imgf000007_0001
NH4CI (25.0 g) is dissolved in NH4OH (150 mL). [Co(H2O)6]Cl2 (26.4 g, 0.10 mol) is added to this solution forming a slurry. H2O2 (30%, 40.0 mL) is slowly dripped into the solution with stirring. Acetic anhydride (30.6 g, 0.30 mol) is slowly added with stirring. The solution is stirred 1 hour at RT. At this point the reaction solution can either be lyophilized to a pink powder or the solution can be rotovapped down and the resulting solid pumped on overnight at 0.05 mm. to remove residual water and NH4OAC. The excess ammonium acetate and ammonium chloride salts can also be removed by washing the soUd with ethanol. Yield 35 gr., 78.1% by UV- Vis spectroscopy. HPLC [according to the method of D.A. Buckingham, et al, Inorg. Chem.. 28, 4567-4574 (1989)] shows all ofthe cobalt is present as [Co(NH3)5OAc]Cl2.
Example 2
Synthesis of (•Coftftty OAclCb Ammonium hydroxide (4498.0 mL, 32.3 mol, 28%) and ammonium chloride (749.8 g, 14.0 mol) are combined in a 12 L three-necked round-bottomed flask fitted with a condenser, internal thermometer, mechanical stirrer, and addition funnel. Once the mixture becomes homogeneous, cobalt(ϋ) chloride hexahydrate (1500.0 g, 6.3 mol) is added in portions over 5 min forming a slurry. The reaction mixture warms to 50 °C and takes on a muddy color. H2O (429.0 g, 6.3 mol, 50%) is added over 30 min. The mixture becomes deep red and homogeneous and the temperature raises to 60-65 °C during addition ofthe peroxide. Ammonium acetate (485.9 g, 6.3 mol) is then added to the mixture 30 min later. After stirring an additional 15 min, acetic anhydride (2242.5 g, 22.1 mol) is added over 1 h. The anhydride is added so as to keep the reaction temperature below 75 °C. The mixture is stirred for 2 h as it cools. The red mixture is filtered and the filtrate treated with isopropanol until an orange-pink solid forms. The solid is collected, washed with isopropanol, ether, and dried to give an orange-pink solid. UV-Vis measurements indicate the product to be 95.3% pure as [Co(NH3)5OAc]Cl2-
WHAT IS CLAIMED IS:

Claims

1. A method for manufacturing cobalt complexes having the formula:
[Co(NH3)5M] Ty wherein the M ligand is selected from substituted and unsubstituted C1-C30 carboxyUc acids having the formula:
RC(O)O-; said method comprising the steps of:
(a) reacting a cobalt (II) salt having the formula:
[Co(H2O)6] Ty wherein T is one or more counteranions present in a number y to obtain a charge-balanced salt; and y is 1 or 2; with concentrated ammonium hydroxide and ammonium chloride; foUowed by
(b) reacting the product of step (a) with an oxidizing agent selected from the group consisting of oxygen, hydrogen peroxide, and mixtures thereof; foUowed by
(c) reacting the product of step (b) with a carboxyUc acid anhydride of the formula:
RC(O)O(O)CR wherein each R is independently selected from substituted or unsubstituted C1-C30 moieties;
(d) optionally, exchanging one T counterion with another T counterion; and
(e) collecting the cobalt complex.
2. The method according to Claim 1 wherein T is selected from the group consisting of chloride, iodide, 13', formate, nitrate, nitrite, sulfate, sulfite, citrate, acetate, carbonate, bromide, PFg", BF4", B(Ph)4", phosphate, phosphite, silicate, tosylate, methanesulfonate, and combinations thereof.
3. The method according to either of Claims 1-2 wherein the concentrated ammonium hydroxide is at least 25% ammonium hydroxide.
4. The method according to any of Claims 1-3 wherein each R in the anhydride is independently selected from the group consisting of hydrogen and C1-C30 unsubstituted and substituted alkyl, C6-C30 unsubstituted and substituted aryl, and C3-C30 unsubstituted and substituted heteroaryl, wherein substituents are selected from the group consisting of -NR3, -NR'4+, -C(O)OR', -OR', -C(O)NR'2. wherein R' is selected from the group consisting of hydrogen and Cj-Cg moieties.
5. The method according to any of Claims 1-4 wherein the M ligand is a carboxylic acid moiety selected from formic, benzoic, octanoic, nonanoic, decanoic, dodecanoic, malonic, maleic, succinic, adipic, phthalic, 2-ethylhexanoic, naphthenoic, oleic, palmitic, triflate, tartrate, stearic, butyric, citric, acrylic, aspartic, fumaric, lauric, linoleic, lactic, malic, and preferably acetic acid.
6. A method for manufacturing cobalt complexes having the formula:
[Co(NH3)5M] Ty wherein the M ligand is selected from substituted and unsubstituted C1-C30 carboxylic acids having the formula:
RC(O)O-; wherein R is selected from Ci-Cjg unsubstituted and substituted alkyl moieties; said method comprising the steps of:
(a) reacting a cobalt (II) salt having the formula:
[Co(H2O)6] Ty wherein T is one or more counteranions present in a number y to obtain a charge-balanced salt; and y is 1 or 2; with concentrated ammonium hydroxide and ammonium chloride; followed by
(b) reacting the product of step (a) with hydrogen peroxide; followed by
(c) reacting the product of step (b) with a carboxylic acid anhydride of the formula:
RC(O)O(O)CR wherein each R is independently selected from C]-Cjg unsubstituted and substituted alkyl moieties; and
(d) optionally, exchanging one T counterion with another T counterion; and
(e) collecting the cobalt complex.
7. The method according to any of Claims 1-6 wherein both R in the anhydride are the same moiety selected from the group consisting of hydrogen, methyl, ethyl, propyl, straight or branched C4-C12 alkyl, and benzyl.
8. The method according to any of Claims 1-7 wherein the anhydride is acetic anhydride.
9. The method according to any of Claims 1-4 and 6 wherein each R in the anhydride is independently selected from the moieties -(CH2)nOH and - (CH2)nNR'4+, wherein n is an integer from 1 to 16, preferably from 2 to 10.
10. The method according to any of Claims 1-9 utilizing from 5.0 to 10.0 equivalents of ammonium hydroxide in a concentrated aqueous solution.
PCT/US1996/001086 1995-06-16 1996-01-25 Method for manufacturing cobalt catalysts WO1997000263A1 (en)

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JP9503028A JPH11509529A (en) 1995-06-16 1996-01-25 Manufacturing method of cobalt catalyst
CA002224462A CA2224462C (en) 1995-06-16 1996-01-25 Method for manufacturing cobalt catalysts
AT96903702T ATE192453T1 (en) 1995-06-16 1996-01-25 METHOD FOR PRODUCING COBALT CATALYSTS
DE69608102T DE69608102T2 (en) 1995-06-16 1996-01-25 METHOD FOR PRODUCING COBALT CATALYSTS
EP96903702A EP0832088B1 (en) 1995-06-16 1996-01-25 Method for manufacturing cobalt catalysts
AU47700/96A AU4770096A (en) 1995-06-16 1996-01-25 Method for manufacturing cobalt catalysts

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GB2034061A (en) * 1978-09-27 1980-05-29 Fuji Photo Film Co Ltd Silver halide colour photographic lightsensitive material

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* Cited by examiner, † Cited by third party
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WO2010010106A1 (en) 2008-07-23 2010-01-28 Pharmaleads Aminophosphinic derivatives that can be used in the treatment of pain

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AU4770096A (en) 1997-01-15
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US5597936A (en) 1997-01-28
DE69608102T2 (en) 2001-01-11
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