US3535380A - 2-alkyl quaternary ammonium compounds - Google Patents

2-alkyl quaternary ammonium compounds Download PDF

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Publication number
US3535380A
US3535380A US703191A US3535380DA US3535380A US 3535380 A US3535380 A US 3535380A US 703191 A US703191 A US 703191A US 3535380D A US3535380D A US 3535380DA US 3535380 A US3535380 A US 3535380A
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US
United States
Prior art keywords
alkyl
quaternary ammonium
benzyl
ammonium compounds
compounds
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 - Lifetime
Application number
US703191A
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English (en)
Inventor
Zdzislaw W Dudzinski
Reginald L Wakeman
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.)
Stepan Co
Original Assignee
Millmaster Onyx Corp
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Publication date
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Assigned to MILLMASTER ONYX GROUP, INC., A DE CORP. reassignment MILLMASTER ONYX GROUP, INC., A DE CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KEWANEE INDUSTRIES, INC.
Assigned to BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. reassignment BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MILLMASTER ONYX GROUP, INC., A DE CORP.
Assigned to STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE. reassignment STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: MILLMASTER ONYX GROUP, INC., A CORP. OF DE.
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Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • ROHCHa wherein R is a straight-chain alkyl having an even number of carbon atoms between 12 and 14, R and R" are lower alkyls, R is a member of the group consisting of benzyl, alkyl-subsituted benzyl wherein the alkyl contains l to carbon atoms, halo-substituted benzyl, and menaphthyl, and wherein X is a halide.
  • This invention relates to quaternary amonium compounds, and it particularly relates to such compounds wherein the nitrogen is directly linked to the penultimate carbon atom of the starting hydrocarbon.
  • the quaternary ammonium compounds embodying the present invention have the structure:
  • R is a straight-chain alkyl having an even number of carbon atoms between 12 and 14, R and R are lower alkyls, preferably either methyl or ethyl, R is a member of the group consisting of benzyl, alkyl-substituted benzyl wherein the alkyl contains 1 to 5 carbon atoms, halo-substituted benzyl, and menaphthyl, and wherein X is a halide.
  • EXAMPLE 1 1 gram equivalent Weight of dimethyl-2 amino hexadecane was reacted with 0.98 gram equivalent weight of benzyl chloride, in an equal weight of 20% isopropanol in distilled water by agitating and heating to 80 C., under ice reflux in a round-bottom flask for about 1 hour, or until no further reaction occurred, as measured by argentometric titration of the ionic chlorine. Reaction was about complete as dimethyl benzyl Z-hexadecyl ammonium chloride, and also present was about 3% of dimethyl 2-hexadecyl amine hydrochloride.
  • the Z-alkyl quaternary ammonium chlorides of Examples 1 and 2 were tested for microbiocidal activity in comparison with the corresponding l-alkyl quaternary ammonium chlorides, using the standard Phenol Coefiicient Method as described in the Oflicial Methods of Analysis of the Association of Oflicial Agricultural Chemists, 9th Edition, pages 63-65, against Staphylococcus aureus and Salmonella typhosa.
  • Dimethyl benzyl Dimethyl benzyl l-amino Z-amino hexadecyl hexadecyl ammoammonium chloride: nium chloride S. aureus 1330 580 S. typhosa 777 640
  • the same procedure was used to compare the corresponding 2-dodecyl, 2-tetradecyl, Z-hexadecyl, and 2 From the above, it can be seen that there is a spectacular and most unexpected jump in biocidal activity between the dodecyl and the tetradecyl compounds.
  • the hexadecyl compounds are even more germicidally active than the tetradecyl.
  • substituted benzyl chlorides wherein the benzyl ring may be substituted in any one or all positions by an alkyl group having from 1 to 5 carbon atoms, or by a halogen such, as chlorine or bromine; or a menaphthyl compound such as a halomethyl naphthylene, exemplified by alphachloromethyl naphthylene, may advantageously be used.
  • the invention claimed 3,287,410 11/1966 DlldZlIlSkl et al. 260583 A compound having the f l 5 2,692,286 10/ 1954 Stayner 260567.6

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US703191A 1968-02-05 1968-02-05 2-alkyl quaternary ammonium compounds Expired - Lifetime US3535380A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70319168A 1968-02-05 1968-02-05
GB4955570 1970-10-19

Publications (1)

Publication Number Publication Date
US3535380A true US3535380A (en) 1970-10-20

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Family Applications (1)

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US703191A Expired - Lifetime US3535380A (en) 1968-02-05 1968-02-05 2-alkyl quaternary ammonium compounds

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US (1) US3535380A (enrdf_load_stackoverflow)
GB (1) GB1266660A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4444790A (en) * 1982-05-27 1984-04-24 Millmaster Onyx Group, Inc. Quaternary ammonium disinfectants
US4450174A (en) * 1982-05-27 1984-05-22 Millmaster Onyx Group, Inc. Decyl quaternary ammonium compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2692286A (en) * 1953-06-29 1954-10-19 California Research Corp Preparation of quaternary ammonium halides
US3287410A (en) * 1963-04-22 1966-11-22 Millmaster Onyx Corp Method of preparing aliphatic amines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2692286A (en) * 1953-06-29 1954-10-19 California Research Corp Preparation of quaternary ammonium halides
US3287410A (en) * 1963-04-22 1966-11-22 Millmaster Onyx Corp Method of preparing aliphatic amines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4444790A (en) * 1982-05-27 1984-04-24 Millmaster Onyx Group, Inc. Quaternary ammonium disinfectants
US4450174A (en) * 1982-05-27 1984-05-22 Millmaster Onyx Group, Inc. Decyl quaternary ammonium compounds

Also Published As

Publication number Publication date
GB1266660A (enrdf_load_stackoverflow) 1972-03-15

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Legal Events

Date Code Title Description
AS Assignment

Owner name: BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. 111 FOU

Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004139/0941

Effective date: 19821222

Owner name: MILLMASTER ONYX GROUP, INC., A DE CORP.

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:KEWANEE INDUSTRIES, INC.;REEL/FRAME:004139/0909

Effective date: 19830407

AS Assignment

Owner name: STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A CORP. OF DE.;REEL/FRAME:004606/0309

Effective date: 19860815

Owner name: STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP. OF DE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A CORP. OF DE.;REEL/FRAME:004606/0309

Effective date: 19860815