US3535380A - 2-alkyl quaternary ammonium compounds - Google Patents
2-alkyl quaternary ammonium compounds Download PDFInfo
- 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
- Authority
- 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
Links
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 4
- -1 dimethyl 2-hexadecyl Chemical group 0.000 description 4
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000003641 microbiacidal effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- PIJNMTNOJHPXFV-UHFFFAOYSA-N 2-methylheptadecan-3-amine Chemical compound CCCCCCCCCCCCCCC(N)C(C)C PIJNMTNOJHPXFV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000001461 argentometric titration Methods 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical group [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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
Landscapes
- 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)
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 |
Family
ID=26266507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US703191A Expired - Lifetime US3535380A (en) | 1968-02-05 | 1968-02-05 | 2-alkyl quaternary ammonium compounds |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3535380A (enrdf_load_stackoverflow) |
| GB (1) | GB1266660A (enrdf_load_stackoverflow) |
Cited By (2)
| 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)
| 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 |
-
1968
- 1968-02-05 US US703191A patent/US3535380A/en not_active Expired - Lifetime
-
1970
- 1970-10-19 GB GB4955570A patent/GB1266660A/en not_active Expired
Patent Citations (2)
| 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)
| 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 |