US3390158A - Aromatic quaternary ammonium salts with disinfectant activity - Google Patents
Aromatic quaternary ammonium salts with disinfectant activity Download PDFInfo
- Publication number
- US3390158A US3390158A US414833A US41483364A US3390158A US 3390158 A US3390158 A US 3390158A US 414833 A US414833 A US 414833A US 41483364 A US41483364 A US 41483364A US 3390158 A US3390158 A US 3390158A
- Authority
- US
- United States
- Prior art keywords
- chloride
- ether
- acetone
- ammonium salts
- quaternary 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 - Lifetime
Links
- 239000000645 desinfectant Substances 0.000 title description 9
- 230000000694 effects Effects 0.000 title description 9
- -1 Aromatic quaternary ammonium salts Chemical class 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 150000003839 salts Chemical class 0.000 description 18
- 239000000126 substance Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 6
- 229940073608 benzyl chloride Drugs 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- QLWONWWTZJMBAU-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.COC1=CC=C(CN(C)C)C=C1OC QLWONWWTZJMBAU-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- WWHJLVMBXXXUFO-UHFFFAOYSA-N 4-(chloromethyl)-1,2-dimethoxybenzene Chemical group COC1=CC=C(CCl)C=C1OC WWHJLVMBXXXUFO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- KHSLHYAUZSPBIU-UHFFFAOYSA-M benzododecinium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 KHSLHYAUZSPBIU-UHFFFAOYSA-M 0.000 description 1
- TTZLKXKJIMOHHG-UHFFFAOYSA-M benzyl-decyl-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 TTZLKXKJIMOHHG-UHFFFAOYSA-M 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- ISWNAMNOYHCTSB-UHFFFAOYSA-N methanamine;hydrobromide Chemical compound [Br-].[NH3+]C ISWNAMNOYHCTSB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Definitions
- the compounds of the invention are useful as disinfectants and can be made in solid crystalline form.
- An example of the compounds of the invention is acarbethoxypentadecyl benzyldimethylammonium chloride.
- the invention relates to new quaternary ammonium salts with disinfectant activity and to the method of preparing same.
- Ri-CH-COOR2 wherein R is a straight or branched aliphatic chain with 1016 carbon atoms, R is a straight or branched alkyl with l-8 carbon atoms, cycloalkyl or aralkyl, R is an alkyl with 1-4 carbon atoms, and the substituents Y and Z, identical or different, stand for an atom of hydrogen, halogen, or a methoxy group, and X is a halogen atom, preferably chlorine.
- the quaternary salts of the above quoted general Formula I represent altogether definable crystalline substances showing disinfectant effect enhanced by their surface activity. They are readily soluble in water, lower alcohols and glycols, capable of forming solutions of 30 percent or even higher concentrations, stable at normal tempera ture.
- Crystalline and chemically homogenous substances of this kind are advantageous above all in that they can secure constant effectiveness of disinfectants prepared with them, that they can be used mostly in the form of aqueous solutions of various concentrations, and in that they offer the possibility of determining the disinfectant effect by external conditions, permitting the study of the mechanism of their effect, etc. From an economical standpoint also the shipment of crystalline substances appears more advantageous and easier than the expensive, uncomfortable, and sometimes diflicult to handle aqueous solutions.
- the reaction can be carried out either without any medium, or in the medium of polar organic solvents, such as acetone, ether, ethly acetate, or dimet'hyl formamide, at a temperature within the range of normal temperature of 1525 up to C., and at atmospheric pressure, or with pressures up to 5 atm.
- polar organic solvents such as acetone, ether, ethly acetate, or dimet'hyl formamide
- the quaternary salt described in Example 5 can be prepared also by heating 12 g. butylester of a-dimethylaminopalmitic acid with 5 g. benzyl chloride to 90 C. for 6 hours. After cooling down the reaction mixture is allowed to stand for 12 hours at room temperature, in order to get crystallized the major part of the quaternary salt formed, thereupon it is stirred up with ether, and further processed to the final product in the way already described.
- the mother liquor obtained in the crystallization of the crude quaternary salt is evaporated and the residue extracted with 15 ml. water and 7.5 ml. ether.
- the aqueous extract is washed with ether, the ethereal extract in turn with water, and both evaporated. From the aqueous extracts further 1.5 g. of the crude quaternary salt is obtained, and from the ethereal extracts 2 g. of the unreacted starting cyclohexylester of tit-dimet-hylaminolauric acid recovered.
- the quaternary salt described in Example 7 can be obtained also by heating 8 g. cyclohexylester of a-dimethylarninolauric acid with 3.2 g. benzyl chloride in 10 ml. acetone or dimethylformamide at 40 C. for 4 days.
- the thus obtained crude quaternary salt is readily soluble in water, giving a clear solution, which forms a heavy sediment by shaking; the salt is soluble in alcohols, acetone and ether, while insoluble in petroleum ether; therefore it is purified by precipitation with petroleum ether from the ethereal solution, thus yielding an amorphous substance, which after some time crystallizes to form a light-yellow substance of fat-like consistence with a low M.P., the ot-carbethoxypentadecyl-/3.4-dimethoxybenzyl/ dimethylammonium chloride.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS673163 | 1963-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3390158A true US3390158A (en) | 1968-06-25 |
Family
ID=5415021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US414833A Expired - Lifetime US3390158A (en) | 1963-12-05 | 1964-11-30 | Aromatic quaternary ammonium salts with disinfectant activity |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3390158A (de) |
| AT (1) | AT249662B (de) |
| BE (1) | BE656646A (de) |
| CH (1) | CH472375A (de) |
| DE (1) | DE1518289A1 (de) |
| GB (1) | GB1029228A (de) |
| NL (1) | NL6414103A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110170164A1 (en) * | 2010-01-08 | 2011-07-14 | Ligang Wang | Tunable thin-film filter |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267344A (en) * | 1972-09-22 | 1981-05-12 | Proteinkemisk Institut. Tilknyttet Akademiet For De Tekniske Videnskaber | N-Substituted N-carboxyanhydrides of α-amino acids and their application in the preparation of peptides |
| GB201605100D0 (en) | 2016-03-24 | 2016-05-11 | Nicoventures Holdings Ltd | Vapour provision system |
| GB201605102D0 (en) | 2016-03-24 | 2016-05-11 | Nicoventures Holdings Ltd | Mechanical connector for electronic vapour provision system |
| GB201605105D0 (en) | 2016-03-24 | 2016-05-11 | Nicoventures Holdings Ltd | Vapour provision apparatus |
| GB201605101D0 (en) | 2016-03-24 | 2016-05-11 | Nicoventures Holdings Ltd | Electronic vapour provision system |
| AU201617188S (en) | 2016-07-15 | 2017-01-16 | Nicoventures Holdings Ltd | Cartomizer for a Vaping Device |
| CN109476408A (zh) | 2016-07-22 | 2019-03-15 | 尼科创业控股有限公司 | 蒸汽供应装置外壳 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2459062A (en) * | 1944-02-08 | 1949-01-11 | American Cyanamid Co | Quaternary ammonium compounds |
-
1964
- 1964-11-30 US US414833A patent/US3390158A/en not_active Expired - Lifetime
- 1964-12-02 CH CH1559164A patent/CH472375A/de unknown
- 1964-12-03 AT AT1024064A patent/AT249662B/de active
- 1964-12-04 BE BE656646D patent/BE656646A/xx unknown
- 1964-12-04 NL NL6414103A patent/NL6414103A/xx unknown
- 1964-12-05 DE DE19641518289 patent/DE1518289A1/de active Pending
- 1964-12-07 GB GB49635/64A patent/GB1029228A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2459062A (en) * | 1944-02-08 | 1949-01-11 | American Cyanamid Co | Quaternary ammonium compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110170164A1 (en) * | 2010-01-08 | 2011-07-14 | Ligang Wang | Tunable thin-film filter |
Also Published As
| Publication number | Publication date |
|---|---|
| BE656646A (de) | 1965-04-01 |
| DE1518289A1 (de) | 1969-05-22 |
| CH472375A (de) | 1969-05-15 |
| AT249662B (de) | 1966-10-25 |
| GB1029228A (en) | 1966-05-11 |
| NL6414103A (de) | 1965-06-07 |
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