US3254102A - Fatty quaternary ammonium group vb metal compounds - Google Patents

Fatty quaternary ammonium group vb metal compounds Download PDF

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US3254102A
US3254102A US140690A US14069061A US3254102A US 3254102 A US3254102 A US 3254102A US 140690 A US140690 A US 140690A US 14069061 A US14069061 A US 14069061A US 3254102 A US3254102 A US 3254102A
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quaternary ammonium
compounds
fatty
metal
metal compounds
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Ronald R Swanson
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General Mills Inc
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    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/19—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/141—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
    • C25D3/00—Electroplating: Baths therefor
    • C25D3/02—Electroplating: Baths therefor from solutions
    • C25D3/54—Electroplating: Baths therefor from solutions of metals not provided for in groups C25D3/04 - C25D3/50
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/10—Groups 5 or 15

Definitions

  • a fatty quaternary ammonium metal compound wherein the anion of said quaternary compound is an inorganic anion containing a metal of Group VB of the Periodic Table.
  • the compounds of the present invention are represented by the following formula:
  • X is a fatty quaternary ammonium cation and Y is an inorganic anion containing a metal of Group VB of the Periodic Table, and m is the valence of the inorganic anion.
  • fatty refers to an aliphatic hydrocarbon radical of 8-24 carbon atoms.
  • fatty quaternary ammonium refers to a quaternary ammonium compound having at least -1 fatty radical attached to the quaternary nitrogen atom.
  • metals of Group VB of the Periodic Table refers to vanadium, niobium (columbium) tantalum, as shown in the Periodic Table set forth on page 573 of General Inorganic Chemistry by Sneed and Maynard, Van Nostrand, New York, 1942.
  • the compounds of the present invention are prepared by reacting fatty quaternary ammonium compounds, particularly the fatty quaternary ammonium chlorides, with a salt having the desired metal containing anion. Using this procedure, the fatty quaternary ammonium compound is dissolved in an organic solvent and contacted with aqueous solution of an inorganic salt having the metal containing inorganic anion. The aqueous solution is then discarded and the organic solvent removed from the organic phase by distillation, preferably under vacuum, to yield the product of the present invention.
  • quaternary ammonium compounds for the preparation of the compounds for the present invention include trimethyl octyl ammonium chloride, methyl triisooctyl ammonium chloride, dimethyl dioleyl ammonium chloride, monomethyl trioleyl ammonium chloride, tetrapal-mityl ammonium chloride, trimethyl myristyl ammonium chloride, dimethyl distearyl ammonium chloride, trimethyl tallow ammonium chloride, dimethyl dicoco ammonium chloride, wherein coco refers to fatty radicals derived from coconut oil fatty acids, methyl octyl morpholium chloride, dilauryl morpholium chloride, lauryl stearyl morpholium chloride, octyl pyridinium chlor
  • the quaternary ammonium compound can be saturated, or contain ethylenic, acetylenic, or aromatic unsaturation. Generally, the quaternary ammonium compound may contain other functional groups, although it is generally preferred to employ compounds "Ice containing functional groups which will remain inert during the preparative procedure.
  • the term caprylyfl used herein refers to the hydrocarbon radicals (octyl and decyl) derived from a mixture of caprylic acid and capric acid.
  • Another method for preparing the compounds of the present invention is by contacting the quaternary ammonium starting material with a simple metallic salt.
  • the quaternary and the metal salt are combined in a mutual solvent and, upon removing the solvent, the desired quaternary ammonium metal compound is prepared.
  • a quaternary ammonium compound having an anion VCl this can be done by contacting quaternary ammonium starting material with vanadium tric'hloride in a mutual solvent such.
  • the product must be completely soluble in the chosen solvent, it is not generally necessary that both the starting quaternary compound and the metallic salt be completely soluble in the solvent, but it is only necessary that they be partially soluble.
  • This technique is most useful when the anion of the quaternary ammonium compound is identical to the anion of the metal compound.
  • the quaternary ammonium chloride should be used to prepare the vanadium chloride complex from the vanadium salt.
  • fatty quaternary ammonium compounds having the following anions can be prepared: TaFq Ta O TaOK TaO TaO Nb O NbO 'NbgO V(VN)6 3, VO3 F2 VOiF5 [VOF4HQO] 2.
  • other compounds containing other anions containing metals of Group VB will be obvious to those skilled in the art.
  • Example I Into a separatory funnel were placed 15 grams of methyl tricaprylyl ammonium chloride, ml. of diethyl ether, and about 50 ml. of a 0.25 M aqueous solution of Na VO After vigorous Shaking, the aqueous solution was discarded and another portion of the 0.25 M aqueous solution of Na VO contacted with the organic solution. This procedure was repeated 20 times. After removing the aqueous phase, the organic phase was stripped of solvent and there was recovered a product having the structural formula (R NCH V0 which analyzed 9.5% V0, as compared to theoretical values of 8.6% where R is caprylyl.
  • the compounds of the present invention are useful as sizing materials for papers, cellulosic materials, polyamides, glass, vitrious and ceramic compositions, as fungicides, as pesticides, as biocides, as bactericides, as anti-barnacle coatings, as corrosion inhibitors, as dyes, as pigments, as colorants, as ultra violet protectors, as wood preservatives, as additives for plastic materials, as additives for adhesives, as additives for glass laminates, as an additive for printing inks for plastics, as fuel and gasoline additives, as lubricant additives, as coating additives, as materials of construction for nuclear engineering, as acceler- Patented May 31, 1966 ators for curing of synthetic resins, as catalysts for emulsion polymerization, as catalysts for intermediate materials for the preparation of catalysts for a variety of chemical reactions, as additives for vinyl plastisols, as

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
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Description

United States Patent 3,254 102 FATTY QUATERNARYAMMONIUM GROUP VB METAL COMPOUNDS Ronald R. Swanson, Minneapolis, Minn., assignor to General Mills, Inc., a corporation of Delaware No Drawing. Filed Sept. 26, 1961, Ser. No. 140,690 6 Claims. (Cl. 260-429) This invention relates to novel quaternary ammonium compounds.
It is an object of this invention to provide novel quaternary ammonium metal compounds. It is another object of this invention to provide the novel process for the preparation of quaternary ammonium metal compounds. Other objects -will appear hereinafter.
The objects of this invention are accomplished by a fatty quaternary ammonium metal compound wherein the anion of said quaternary compound is an inorganic anion containing a metal of Group VB of the Periodic Table. The compounds of the present invention are represented by the following formula:
where X is a fatty quaternary ammonium cation and Y is an inorganic anion containing a metal of Group VB of the Periodic Table, and m is the valence of the inorganic anion.
As used herein, the term fatty refers to an aliphatic hydrocarbon radical of 8-24 carbon atoms. The term fatty quaternary ammonium refers to a quaternary ammonium compound having at least -1 fatty radical attached to the quaternary nitrogen atom. As used herein, the term metals of Group VB of the Periodic Table refers to vanadium, niobium (columbium) tantalum, as shown in the Periodic Table set forth on page 573 of General Inorganic Chemistry by Sneed and Maynard, Van Nostrand, New York, 1942.
The compounds of the present invention are prepared by reacting fatty quaternary ammonium compounds, particularly the fatty quaternary ammonium chlorides, with a salt having the desired metal containing anion. Using this procedure, the fatty quaternary ammonium compound is dissolved in an organic solvent and contacted with aqueous solution of an inorganic salt having the metal containing inorganic anion. The aqueous solution is then discarded and the organic solvent removed from the organic phase by distillation, preferably under vacuum, to yield the product of the present invention.
Because of the availability of quaternary ammonium chlorides, they are generally used as a starting material in the preparation. However, other quaternary ammonium salts can be used with equal success. Suitable quaternary ammonium compounds for the preparation of the compounds for the present invention include trimethyl octyl ammonium chloride, methyl triisooctyl ammonium chloride, dimethyl dioleyl ammonium chloride, monomethyl trioleyl ammonium chloride, tetrapal-mityl ammonium chloride, trimethyl myristyl ammonium chloride, dimethyl distearyl ammonium chloride, trimethyl tallow ammonium chloride, dimethyl dicoco ammonium chloride, wherein coco refers to fatty radicals derived from coconut oil fatty acids, methyl octyl morpholium chloride, dilauryl morpholium chloride, lauryl stearyl morpholium chloride, octyl pyridinium chloride, stearyl pyridinium chloride, methyl trilinoleyl ammonium chloride, trioctyl benzyl ammonium chloride, stearyl tribenzyl ammonium chloride, and butyl lauryl dibenzyl ammonium chloride. The quaternary ammonium compound can be saturated, or contain ethylenic, acetylenic, or aromatic unsaturation. Generally, the quaternary ammonium compound may contain other functional groups, although it is generally preferred to employ compounds "Ice containing functional groups which will remain inert during the preparative procedure. The term caprylyfl used herein refers to the hydrocarbon radicals (octyl and decyl) derived from a mixture of caprylic acid and capric acid.
Another method for preparing the compounds of the present invention is by contacting the quaternary ammonium starting material with a simple metallic salt. The quaternary and the metal salt are combined in a mutual solvent and, upon removing the solvent, the desired quaternary ammonium metal compound is prepared. 'For example, if it is desired to prepare a quaternary ammonium compound having an anion VCl this can be done by contacting quaternary ammonium starting material with vanadium tric'hloride in a mutual solvent such.
as ether or isopropanol. While the product must be completely soluble in the chosen solvent, it is not generally necessary that both the starting quaternary compound and the metallic salt be completely soluble in the solvent, but it is only necessary that they be partially soluble. This technique is most useful when the anion of the quaternary ammonium compound is identical to the anion of the metal compound. For example, the quaternary ammonium chloride should be used to prepare the vanadium chloride complex from the vanadium salt. One advantage of this technique and a highly unusual feature of the present invention is that it is possible to prepare, by
this method, anions which could not otherwise be pre-,
pared because of their instability in water.
,Using the above described preparative procedures, fatty quaternary ammonium compounds having the following anions can be prepared: TaFq Ta O TaOK TaO TaO Nb O NbO 'NbgO V(VN)6 3, VO3 F2 VOiF5 [VOF4HQO] 2. other compounds containing other anions containing metals of Group VB will be obvious to those skilled in the art.
In order to illustrate certain preferred embodiments of .the present invention, the following example is included. Unless otherwise indicated, all parts and percentages used herein are .by weight.
Example I Into a separatory funnel were placed 15 grams of methyl tricaprylyl ammonium chloride, ml. of diethyl ether, and about 50 ml. of a 0.25 M aqueous solution of Na VO After vigorous Shaking, the aqueous solution was discarded and another portion of the 0.25 M aqueous solution of Na VO contacted with the organic solution. This procedure was repeated 20 times. After removing the aqueous phase, the organic phase was stripped of solvent and there was recovered a product having the structural formula (R NCH V0 which analyzed 9.5% V0, as compared to theoretical values of 8.6% where R is caprylyl.
The foregoing example is an illustration of certain preferred embodiments of the present invention and is not to be construed as limitations on the scope thereof. The compounds of the present invention are useful as sizing materials for papers, cellulosic materials, polyamides, glass, vitrious and ceramic compositions, as fungicides, as pesticides, as biocides, as bactericides, as anti-barnacle coatings, as corrosion inhibitors, as dyes, as pigments, as colorants, as ultra violet protectors, as wood preservatives, as additives for plastic materials, as additives for adhesives, as additives for glass laminates, as an additive for printing inks for plastics, as fuel and gasoline additives, as lubricant additives, as coating additives, as materials of construction for nuclear engineering, as acceler- Patented May 31, 1966 ators for curing of synthetic resins, as catalysts for emulsion polymerization, as catalysts for intermediate materials for the preparation of catalysts for a variety of chemical reactions, as additives for vinyl plastisols, as electroplating.materials, as a source of pure metals having unusual properties because of their complex nature, as vapor-phase plating chemicals, as anti-static additives for plastics and coatings, and the like. The products of the present invention can also be used to impregnate ceramics, silica, clay, alumina, and the like, and after firing the impregnated material, a product is obtained having the desired metal uniformly impregnated throughout the material.
The embodiments of the present invention in which an exclusive property or privilege is claimed, are defined as follows:
1. Complex compounds of the structure where X is a fatty quaternary ammonium cation wherein at least one of the four organic groups attached to the nitrogen atom is an aliphatic hydrocarbon radical of 8-24 carbon atoms, Y is an inorganic anion containing a metal of Group VB of the Periodic Table of Elements and m is the valence of said anion.
2. The complex compounds of claim 1 wherein the metal is vanadium.
4 3. The complex compounds of claim 1 wherein the metal is niobium.
4. The complex compounds of claim 1 wherein the metal is tantalum.
5. The complex compounds of the formula:
X VO
where R is selected from the group consisting of octyl and decyl.
References Cited by the Examiner UNITED STATES PATENTS 2,580,473 1/1952 Sowa et a1. 260429 2,798,103 7/1957 Schaffer et a1. 260-429 2,902,401 9/1959 Harwood et a1. 260429 TOBIAS E. LEVOW, Primary Examiner.
ABRAHAM H. WINKELSTEIN, Examiner.
W. I. VanBALEN, Assistant Examiner.

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365313A (en) * 1962-06-11 1968-01-23 American Cyanamid Co Anti-corrosion compositions
US3505372A (en) * 1966-11-23 1970-04-07 Frances J Josh Onium salts containing metal complexes as the anions
US3539605A (en) * 1968-01-30 1970-11-10 Nalco Chemical Co Ion exchange method of preparing quaternary ammonium compounds
US3620711A (en) * 1967-07-18 1971-11-16 Ici Ltd Herbicidal process and compositions for use therein
US4605752A (en) * 1984-11-09 1986-08-12 Exxon Research And Engineering Co. Quaternary ammonium tetrathiovanadates
EP0227179A1 (en) * 1985-12-19 1987-07-01 ENICHEM SYNTHESIS S.p.A. Stainless steels stress corrosion inhibitors

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2580473A (en) * 1946-03-22 1952-01-01 Sowa Complex ammonium salts and processes for producing the same
US2798103A (en) * 1953-07-20 1957-07-02 Union Oil Co Separation of aromatic compounds by clathrate formation with a werner complex
US2902401A (en) * 1956-07-13 1959-09-01 Armour & Co Fungicidal compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2580473A (en) * 1946-03-22 1952-01-01 Sowa Complex ammonium salts and processes for producing the same
US2798103A (en) * 1953-07-20 1957-07-02 Union Oil Co Separation of aromatic compounds by clathrate formation with a werner complex
US2902401A (en) * 1956-07-13 1959-09-01 Armour & Co Fungicidal compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365313A (en) * 1962-06-11 1968-01-23 American Cyanamid Co Anti-corrosion compositions
US3505372A (en) * 1966-11-23 1970-04-07 Frances J Josh Onium salts containing metal complexes as the anions
US3620711A (en) * 1967-07-18 1971-11-16 Ici Ltd Herbicidal process and compositions for use therein
US3539605A (en) * 1968-01-30 1970-11-10 Nalco Chemical Co Ion exchange method of preparing quaternary ammonium compounds
US4605752A (en) * 1984-11-09 1986-08-12 Exxon Research And Engineering Co. Quaternary ammonium tetrathiovanadates
EP0227179A1 (en) * 1985-12-19 1987-07-01 ENICHEM SYNTHESIS S.p.A. Stainless steels stress corrosion inhibitors

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