GB821242A - Quaternary ammonium compounds - Google Patents

Quaternary ammonium compounds

Info

Publication number
GB821242A
GB821242A GB13815/56A GB1381556A GB821242A GB 821242 A GB821242 A GB 821242A GB 13815/56 A GB13815/56 A GB 13815/56A GB 1381556 A GB1381556 A GB 1381556A GB 821242 A GB821242 A GB 821242A
Authority
GB
United Kingdom
Prior art keywords
units
chloride
dimethylaminomethyl
tris
phenol
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
GB13815/56A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB821242A publication Critical patent/GB821242A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises quaternary ammonium compounds formed from one mole. of tris-(dimethylaminomethyl) phenol and one to three moles. of a compound comprising a hydrocarbon group or a substituted hydrocarbon group having ten to twenty-one carbon atoms attached to a reactive halogen. The compounds of the invention are prepared from tris-(dimethylaminomethyl) phenol and organic halides of formula RX, where R is C10-C21 hydrocarbon or substituted hydrocarbon and X is a halogen. Many values are specified for R viz. alkyl, alkenyl, mono-, di-, or tri-alkylbenzyl, alkadienyl, alkynyl, alkenylbenzyl, alkynylbenzyl, alkoxyalkyl, or hydrocarbon groups substituted with ester, ketone or amide groups. Any of the geometrical isomers or a mixture of isomers of the tris-(dimethylaminomethyl) phenol may be used. When more than one mole. of RX is reacted with a mole. of tris-(dimethylaminomethyl) phenol, RX need not represent the same specific compound. A catalyst, e.g. sodium iodide may be used in the reaction process, which preferably takes place at 50-150 DEG C., preferably the reflux temperature of the reaction mixture at atmospheric pressure or above, a solvent such as ethanol, isopropanol, butanol, nitromethane, acetonitrile, dimethyl formamide, dioxane, propyl ether or butyl ether may also be present. The reaction is continued until the required number of moles. of RX has reacted with the tris-(dimethylaminomethyl) phenol, as determined by estimating the theoretical amount of ionizable halide in the reaction system. Examples are given of the preparation of compounds from one unit of tris-(dimethylaminomethyl) phenol, and 1, 2 and 3 units of dodecylmethylbenzyl chloride, three units of dodecenyl chloride, three units of decyl bromide, three units of propoxydecyl chloride, three units of bromododecanamide, three units of octylbenzyl chloride, one unit of dodecyl chloride, one unit each of dodecynyl chloride, decyl bromide and propoxydecyl chloride. Other compounds mentioned, which may be prepared by similar methods are those containing three units of dodecylmethyl benzyl bromide, two units of dodecenyl chloride, octadecynyl chloride, one and two units of decyl bromide, ocytyl chlorobutyrate, chlorodecylcyclobutyl ketone, and one unit of decyl bromide together with two units of dodecynyl chloride.
GB13815/56A 1955-05-23 1956-05-04 Quaternary ammonium compounds Expired GB821242A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US821242XA 1955-05-23 1955-05-23

Publications (1)

Publication Number Publication Date
GB821242A true GB821242A (en) 1959-10-07

Family

ID=22169221

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13815/56A Expired GB821242A (en) 1955-05-23 1956-05-04 Quaternary ammonium compounds

Country Status (1)

Country Link
GB (1) GB821242A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008095069A2 (en) * 2007-01-31 2008-08-07 Sigma-Aldrich Co. High stability polyionic liquid salts
US7776582B2 (en) 2004-07-09 2010-08-17 Sigma-Aldrich Co. Optically enhanced chiral ionic liquids
US8168830B2 (en) 2004-07-23 2012-05-01 Sigma-Aldrich Co. Llc High stability diionic liquid salts
US8182581B2 (en) 2004-07-23 2012-05-22 Sigma-Aldrich Co. Llc High stability diionic liquid salts

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7776582B2 (en) 2004-07-09 2010-08-17 Sigma-Aldrich Co. Optically enhanced chiral ionic liquids
US8168830B2 (en) 2004-07-23 2012-05-01 Sigma-Aldrich Co. Llc High stability diionic liquid salts
US8182581B2 (en) 2004-07-23 2012-05-22 Sigma-Aldrich Co. Llc High stability diionic liquid salts
US8956445B2 (en) 2004-07-23 2015-02-17 Sigma-Aldrich Co. High stability diionic liquid salts
WO2008095069A2 (en) * 2007-01-31 2008-08-07 Sigma-Aldrich Co. High stability polyionic liquid salts
WO2008095069A3 (en) * 2007-01-31 2009-04-23 Sigma Aldrich Co High stability polyionic liquid salts
US8097721B2 (en) 2007-01-31 2012-01-17 Sigma-Aldrich Co. Llc High stability polyionic liquid salts
US8481722B2 (en) 2007-01-31 2013-07-09 Sigma-Aldrich Co. Llc High stability polyionic liquid salts

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