GB735631A - Improvements relating to the preparation of quaternary ammonium compounds - Google Patents

Improvements relating to the preparation of quaternary ammonium compounds

Info

Publication number
GB735631A
GB735631A GB2368850A GB2368850A GB735631A GB 735631 A GB735631 A GB 735631A GB 2368850 A GB2368850 A GB 2368850A GB 2368850 A GB2368850 A GB 2368850A GB 735631 A GB735631 A GB 735631A
Authority
GB
United Kingdom
Prior art keywords
nitrate
potassium
chloride
bromide
ammonium
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
Application number
GB2368850A
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.)
MILTON ANTISEPTIC Ltd
Original Assignee
MILTON ANTISEPTIC 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 MILTON ANTISEPTIC Ltd filed Critical MILTON ANTISEPTIC Ltd
Priority to GB2368850A priority Critical patent/GB735631A/en
Publication of GB735631A publication Critical patent/GB735631A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

Quaternary ammonium salts QY are made from salts of the same cation QX by treating aqueous solutions of the latter with aqueous solutions of the acid HY or a salt thereof MY in the presence of an organic solvent in which QY is soluble, which solvent is substantially immiscible with water or with strong aqueous solutions of inorganic salts; Q is an ion NR1R2R3R4 where R1-R4 are the same or different organic radicals or two or three of them may form a single cyclic group; M is a mono- or polyvalent inorganic cation and X and Y are different mono- or polyvalent anions. The product may contain unchanged QX. In the examples (1) tetradecylpyridinium nitrate is made from the bromide and ammonium nitrate; (2) cetylbenzyldimethylammonium nitrate is obtained from the chloride and potassium nitrate; (3) myristylmethyldiethanolammonium nitrate is prepared from the chloride and potassium nitrate; (4) di-n-octyldimethylammonium nitrate is made from the bromide and potassium nitrate; (5) "lorol"-pyridinium nitrate is produced from the chloride and potassium nitrate; (6) myristylpyridinium nitrate is obtained from the iodide and ammonium nitrate; (7) cetylpyridinium chloride is prepared from the iodide and potassium chloride; (8) as in (7) using ammonium chloride; (9) cetylpyridinium nitrate is made from the iodide and potassium nitrate; (10) as in (9) using ammonium nitrate; (11), (12) and (13) as in (1) using varying proportions; (14) tetradecylpyridinium nitrate is produced from the bromide and potassium, calcium, sodium, ammonium or magnesium nitrate; (15) tetradecylpyridinium bromide is obtained from the nitrate and ammonium bromide; (16) myristylpyridinium chloride is treated with the following: potassium nitrate, nitric acid, potassium ethylsulphate, potassium methylsulphate, potassium acetate, acetic acid, potassium perchlorate, potassium sulphate and potassium dihydrogen phosphate. The solvent is chloroform in examples (1)-(6) and (11)-(16) and sec-butyl alcohol in the others. The salt MY may be added all at once or in successive portions after separation of the phases. If an emulsion forms it may be broken, e.g. by alteration of pH. Other specified ions for Q are dialkylmorpholinium, alkylpicolinium, alkyltrimethylammonium and p-t-octylphenoxyethoxyethyl - dimethylbenzylammonium. Y may also be nitrite. Other specified solvents are n- and iso-butyl alcohols. The Provisional Specification refers also to the following conversions: cetyltrimethylammonium bromide into chloride with ammonium chloride, sodium chloride or calcium chloride, cetylpyridinium chloride into nitrate with potassium nitrate (and isobutyl alcohol), cetyldimethylbenzylammonium bromide into nitrate with ammonium nitrate, cetyltrimethylammonium bromide into nitrate and iodide with potassium nitrate and iodide respectively, tetradecylpyridinium bromide into chloride and iodide with calcium or sodium chloride and potassium or sodium iodide respectively, and cetylpyridinium iodide into bromide with ammonium bromide.
GB2368850A 1950-09-27 1950-09-27 Improvements relating to the preparation of quaternary ammonium compounds Expired GB735631A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2368850A GB735631A (en) 1950-09-27 1950-09-27 Improvements relating to the preparation of quaternary ammonium compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2368850A GB735631A (en) 1950-09-27 1950-09-27 Improvements relating to the preparation of quaternary ammonium compounds

Publications (1)

Publication Number Publication Date
GB735631A true GB735631A (en) 1955-08-24

Family

ID=10199660

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2368850A Expired GB735631A (en) 1950-09-27 1950-09-27 Improvements relating to the preparation of quaternary ammonium compounds

Country Status (1)

Country Link
GB (1) GB735631A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3073827A (en) * 1959-06-03 1963-01-15 Air Prod & Chem Method for preparing quaternary alkyl nitrates of diazabicyclo-octane
US3083203A (en) * 1960-06-01 1963-03-26 Jefferson Chem Co Inc Method for preparing n, n'-dimethyltriethylenediammonium dinitrate
US3162686A (en) * 1959-02-26 1964-12-22 Dow Chemical Co Preparation of lower tetraalkyl quaternary ammonium nitrates
US3175005A (en) * 1961-10-09 1965-03-23 Armour & Co Preparation of quaternary ammonium nitrites
US3175004A (en) * 1961-03-24 1965-03-23 Armour & Co Preparation of quaternary ammonium nitrates
US3232941A (en) * 1959-03-13 1966-02-01 Pennsalt Chemicals Corp N,n'-dialkyltriethylenediammonium dinitrates
GB2230263A (en) * 1989-04-10 1990-10-17 Tobishi Pharmaceutical Co Quaternary ammonium compounds having muscle relaxation activity
US5705696A (en) * 1996-08-01 1998-01-06 General Electric Company Extractive method for the preparation of quaternary salts
WO2012099720A1 (en) * 2011-01-21 2012-07-26 Corning Incorporated Electrolyte synthesis for ultracapacitors
US8663492B2 (en) 2011-01-21 2014-03-04 Corning Incorporated Electrolyte synthesis for ultracapacitors
WO2014081628A1 (en) * 2012-11-20 2014-05-30 Corning Incorporated Electrolyte synthesis for ultracapacitors
US9117591B2 (en) 2011-01-21 2015-08-25 Corning Incorporated Electrolyte synthesis for ultracapacitors

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3162686A (en) * 1959-02-26 1964-12-22 Dow Chemical Co Preparation of lower tetraalkyl quaternary ammonium nitrates
US3232941A (en) * 1959-03-13 1966-02-01 Pennsalt Chemicals Corp N,n'-dialkyltriethylenediammonium dinitrates
US3073827A (en) * 1959-06-03 1963-01-15 Air Prod & Chem Method for preparing quaternary alkyl nitrates of diazabicyclo-octane
US3083203A (en) * 1960-06-01 1963-03-26 Jefferson Chem Co Inc Method for preparing n, n'-dimethyltriethylenediammonium dinitrate
US3175004A (en) * 1961-03-24 1965-03-23 Armour & Co Preparation of quaternary ammonium nitrates
US3175005A (en) * 1961-10-09 1965-03-23 Armour & Co Preparation of quaternary ammonium nitrites
GB2230263A (en) * 1989-04-10 1990-10-17 Tobishi Pharmaceutical Co Quaternary ammonium compounds having muscle relaxation activity
US5093370A (en) * 1989-04-10 1992-03-03 Tobishi Yakuhin Kogyo Kabushiki Kaisha Quaternary ammonium compounds having muscle relaxation activity
US5705696A (en) * 1996-08-01 1998-01-06 General Electric Company Extractive method for the preparation of quaternary salts
WO2012099720A1 (en) * 2011-01-21 2012-07-26 Corning Incorporated Electrolyte synthesis for ultracapacitors
US8663492B2 (en) 2011-01-21 2014-03-04 Corning Incorporated Electrolyte synthesis for ultracapacitors
US9117591B2 (en) 2011-01-21 2015-08-25 Corning Incorporated Electrolyte synthesis for ultracapacitors
US9275802B2 (en) 2011-01-21 2016-03-01 Corning Incorporated Electrolyte synthesis for ultracapacitors
WO2014081628A1 (en) * 2012-11-20 2014-05-30 Corning Incorporated Electrolyte synthesis for ultracapacitors

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