GB786758A - New quaternary ammonium pyrophosphate compounds - Google Patents

New quaternary ammonium pyrophosphate compounds

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Publication number
GB786758A
GB786758A GB5402/55A GB540255A GB786758A GB 786758 A GB786758 A GB 786758A GB 5402/55 A GB5402/55 A GB 5402/55A GB 540255 A GB540255 A GB 540255A GB 786758 A GB786758 A GB 786758A
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United Kingdom
Prior art keywords
quaternary ammonium
pyrophosphate
ammonium
compounds
group
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.)
Expired
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GB5402/55A
Inventor
Peter William Brett Semmens
James Denis Summers-Smith
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB5402/55A priority Critical patent/GB786758A/en
Priority to DEI11324A priority patent/DE1012415B/en
Priority to FR1145485D priority patent/FR1145485A/en
Publication of GB786758A publication Critical patent/GB786758A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
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    • 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
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Developing Agents For Electrophotography (AREA)

Abstract

The invention comprises quaternary ammonium pyrophosphate compounds in which each quaternary ammonium group has the four nitrogen covalencies attached to organic groups at least one of which is or contains an alkyl radical having 6 or more carbon atoms, said compounds having the formula X2Y2P2O7 in which Y is a quaternary ammonium group and X is hydrogen or a quaternary ammonium group which may or may not be the same group as Y. The compounds may be obtained by the following general method: A column of a strongly basic anion exchange resin is activated in the hydroxide form by contact with an aqueous solution of a water-soluble hydroxide, e.g. sodium hydroxide. An aqueous solution of any water-soluble quaternary ammonium salt (e.g. the bromide) containing the appropriate quaternary ammonium group is repeatedly passed through the column until the anion is not detectable in the drainings and the resulting solution of quaternary ammonium hydroxide is treated with an aqueous solution of pyrophosphoric acid until the pH is 4.5. The mixture is then evaporated to dryness under vacuum and the diquaternary ammonium pyrophosphate product may be dried over phosphoric oxide in a vacuum desiccator. If the tetra-quaternary ammonium pyrophosphate is required, the same procedure is adopted except that the pH is adjusted to 8.5. When compounds in which X and Y in the above general formula are different groups are to be prepared, a solution of the compound X2H2P2O7 is first prepared by the above method and this is then treated with a solution of the quaternary ammonium hydroxide YOH, wherein Y is different from X until the pH is 8.5 and the solid compound X2Y2P2O7 is obtained by evaporation. Specified quaternary ammonium groups are cetyl trimethyl ammonium, didecyl dimethyl ammonium, cetyl pyridinium, tetradecyl pyridinium, lauryl benzyl dimethyl ammonium, 2-(p-tert.-octyl phenoxy) ethyl benzyl diethyl ammonium, di-n-octyl dimethyl ammonium and stearyl benzyl dimethyl ammonium. Examples are given for the production of di-(cetyl trimethyl ammonium) dihydrogen pyrophosphate and tetra-(cetyl trimethyl ammonium) pyrophosphate using the above general method. An example is also given to illustrate an alternative method of preparing the tetra-pyrophosphate salts. In this case an anion exchange resin is activated by contact in a column with an aqueous solution containing tetra-sodium pyrophosphate and then washed with water until the washings give a pH of 7-8. A solution of cetyl trimethyl ammonium hydroxide (prepared by passing the corresponding bromide through a column of anion exchange resin activated by contact with an aqueous solution of sodium hydroxide) is adjusted to a pH of 7.0 with an aqueous normal solution of sulphuric acid and the resultant solution is then passed repeatedly down the column of ion exchange resin, which has been activated with the sodium pyrophosphate solution, until the drainings are free from sulphate ion and the collected drainings are then evaporated under reduced pressure and dried over phosphoric acid. The products are stated to be suitable for use as boundary lubricants (see Group III).ALSO:A composition suitable for use as a boundary lubricant comprises one or more quaternary ammonium pyrophosphate compounds (as defined below) and one or more suitable liquid or solid vehicles in which the pyrophosphate compound or compounds may be dissolved or dispersed. The quarternary ammonium pyrophosphate compounds are compounds in which each quaternary ammonium group has the four nitrogen covalencies attached to organic groups at least one of which is or contains an alkyl radical having 6 or more carbon atoms and have the formula X2Y2P2O, in which Y is a quaternary ammonium group and X is hydrogen or a quaternary ammonium group which may or may not be the same group as Y (see Group IV (b)). Specified quaternary ammonium groups are cetyl trimethyl-, didecyl (or di-n-octyl) dimethyl-, lauryl benzyl dimethyl-, stearyl benzyl dimethyl-, and 2-(p-tert. octyl phenoxy) ethyl benzyl diethyl-ammonium, cetyl pyridinium, and tetradecyl pyridinium. Specified vehicles in which the pyrophosphates may be dissolved or dispersed are hydrocarbons, mineral oils, vegetable oils such as castor oil, siloxane oils, aliphatic esters, alkylene glycols, petroleum jelly, animal fats, vegetable and mineral grease-like substances, solid siloxane compounds and fatty acids and their soaps and esters. Specified quaternary ammonium compounds are di-(cetyl trimethyl ammonium) dihydrogen pyrophosphate and tetra aetyl trimethyl ammonium) pyrophosphate.
GB5402/55A 1955-02-23 1955-02-23 New quaternary ammonium pyrophosphate compounds Expired GB786758A (en)

Priority Applications (3)

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GB5402/55A GB786758A (en) 1955-02-23 1955-02-23 New quaternary ammonium pyrophosphate compounds
DEI11324A DE1012415B (en) 1955-02-23 1956-02-21 lubricant
FR1145485D FR1145485A (en) 1955-02-23 1956-02-23 Chemical compounds applicable as limit lubricants, and their manufacturing process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5402/55A GB786758A (en) 1955-02-23 1955-02-23 New quaternary ammonium pyrophosphate compounds

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GB786758A true GB786758A (en) 1957-11-27

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DE (1) DE1012415B (en)
FR (1) FR1145485A (en)
GB (1) GB786758A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3506712A (en) * 1964-08-31 1970-04-14 Mobil Oil Corp Quaternary amine salts useful as fuel stabilizers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3506712A (en) * 1964-08-31 1970-04-14 Mobil Oil Corp Quaternary amine salts useful as fuel stabilizers

Also Published As

Publication number Publication date
DE1012415B (en) 1957-07-18
FR1145485A (en) 1957-10-25

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