GB763455A - Improvements in addition compounds of amines and halides of aluminium and boron - Google Patents
Improvements in addition compounds of amines and halides of aluminium and boronInfo
- Publication number
- GB763455A GB763455A GB28005/53A GB2800553A GB763455A GB 763455 A GB763455 A GB 763455A GB 28005/53 A GB28005/53 A GB 28005/53A GB 2800553 A GB2800553 A GB 2800553A GB 763455 A GB763455 A GB 763455A
- Authority
- GB
- United Kingdom
- Prior art keywords
- boron
- aluminium
- amine
- iodine
- carbon atoms
- 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
Links
- 150000001412 amines Chemical class 0.000 title abstract 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title abstract 8
- 229910052796 boron Inorganic materials 0.000 title abstract 8
- 150000001875 compounds Chemical class 0.000 title abstract 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title abstract 5
- 229910052782 aluminium Inorganic materials 0.000 title abstract 5
- 239000004411 aluminium Substances 0.000 title abstract 5
- 150000004820 halides Chemical class 0.000 title abstract 4
- -1 alkyl radicals Chemical class 0.000 abstract 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 8
- 229910015900 BF3 Inorganic materials 0.000 abstract 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 229910052740 iodine Chemical group 0.000 abstract 4
- 239000011630 iodine Chemical group 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 230000002421 anti-septic effect Effects 0.000 abstract 3
- 229940064004 antiseptic throat preparations Drugs 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Substances 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 2
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- 239000003899 bactericide agent Substances 0.000 abstract 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 239000000417 fungicide Substances 0.000 abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- DCNHQNGFLVPROM-VAWYXSNFSA-N (e)-n,n-dimethyloctadec-9-en-1-amine Chemical compound CCCCCCCC\C=C\CCCCCCCCN(C)C DCNHQNGFLVPROM-VAWYXSNFSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 239000004166 Lanolin Substances 0.000 abstract 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 abstract 1
- LPVNUKXUQMFECB-UHFFFAOYSA-K aluminum triiodoborane triiodide Chemical compound B(I)(I)I.[I-].[Al+3].[I-].[I-] LPVNUKXUQMFECB-UHFFFAOYSA-K 0.000 abstract 1
- 230000001166 anti-perspirative effect Effects 0.000 abstract 1
- 239000003213 antiperspirant Substances 0.000 abstract 1
- YMEKEHSRPZAOGO-UHFFFAOYSA-N boron triiodide Chemical compound IB(I)I YMEKEHSRPZAOGO-UHFFFAOYSA-N 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 229940039717 lanolin Drugs 0.000 abstract 1
- 235000019388 lanolin Nutrition 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 abstract 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises as new products stable compounds having the general formula [(R1)(R2)(R3)N]n.EX3 in which R1 is a straight chain alkyl, alkenyl or alkadienyl radical having from 12 to 18 carbon atoms with a terminal carbon atom of the chain attached to the nitrogen atom, R2 and R3 are selected from hydrogen, alkyl radicals containing 1-5 carbon atoms, and the cyclohexyl, phenyl and benzyl radicals, E is aluminium or boron, X is chlorine, bromine, or iodine and n is an integer from 1 to 4, or X is fluorine, E is boron and n is an integer from 1 to 3. The radical R1 may be n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 9-octadecenyl, hexadecenyl, tetradecenyl, trans-9-octadecenyl or 9-12 octadecadienyl. Specified C1-C5 alkyl radicals are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and n-amyl. The addition compounds may be obtained by simply contacting the amine with the halide in the presence or absence of an inert solvent such as benzene, toluene, ether, ethyl acetate, cyclohexane or dioxane. When boron trifluoride is used the reaction may be effected by using gaseous boron trifluoride, the ether-boron trifluoride complex, or the boron trifluoride complex with ethyl acetate or dioxane. The addition compounds may be purified by precipitation from solution in an organic solvent. Examples are given for the production of complexes of aluminium chloride with two and four molecular proportions of monolauryl amine; of boron trichloride with one, two, three and four molecular proportions of monolauryl amine and with four molecular proportions of mixed coconut oil monoamines and monostearyl amine respectively; of aluminium bromide, aluminium iodide boron tri-iodide and boron tribromide respectively with four molecular proportions of monolauryl amine, and of boron fluoride with one, two and three molecular proportions of monolauryl amine, one, two and three molecular proportions of monocetyl amine and with 1 molecular proportion of 9-octadecenyl dimethyl amine. Other amines specified are mono-tetradecyl amine, lauryldimethylamine, cetyldiethylamine and cetyl dimethylamine. The complexes formed by the addition of one mol. of the amine to one mol. of the halide are soluble in various solvents, e.g. ethyl acetate, benzene, toluene, alcohol, ether and dioxane and the solutions are stated to be valuable antiseptics, fungicides, larvicides and bactericides. The products are soluble in water and are useful detergents, wetting agents, and emulsifying agents. They may also be used as finishing agents for textiles, e.g. cotton and cellulose acetate. Specification 645,425 is referred to.ALSO:Compounds having the general formula [(R1)(R2)(R3)N]nEX3 in which R1 is a straight chain alkyl, alkenyl, or alkadienyl radical having from 12 to 18 carbon atoms with a terminal carbon atom of the chain attached to the nitrogen atom, R2 and R3 are selected from hydrogen, alkyl radicals containing 1 to 5 carbon atoms, E is aluminium or boron, X is chlorine, bromine or iodine, and n is an integar from 1 to 4, or X is fluorine, E is boron and n is an integar from 1 to 3 (see Group IV(b)) can be incorporated directly into paints and lacquers where they function as spreading agents and retard the growth of fungi. Specification 645,425 is referred to. Aluminium triiodide is obtained by heating iodine to 180 DEG C. and dropping small pieces of aluminium ribbon into the molten iodine while maintaining a blanket of carbon dioxide over the mixture which is then cooled and heated to volatilise the remaining iodine. Boron triiodide and aluminium fluoride are obtained by adding boron trofluoride to molten aluminium triiodide at 190 DEG C. in a flask fitted with a condenser, thermometer and gas inlet tube.ALSO:Compounds having the general formula [(R1) (R2) (R3) N]n-EX3 in which R1 is a straight chain alkyl, alkenyl, or alkadienyl radical having from 12 to 18 carbon atoms with a terminal carbon atom of the chain attached to the nitrogen atom, R2 and R3 are selected from hydrogen, alkyl radicals containing 1 to 5 carbon atoms, and the cyclohexyl, phenyl, and benzyl radicals, E is aluminium or boron, X is chlorine, bromine, or iodine, and n is an integer from 1 to 4, or X is fluorine, E is boron and n is an integer from 1 to 3 (see Group IV (b) are stated to be useful as antiseptics larvicides and insecticides, and also as anti-perspirants, e.g. when contained in a non-ionic cream base, alcohol, or lanolin. The compounds containing one molecule of the halide are soluble in various organic solvents, e.g. ethyl acetate, benzene, toluene, alcohol, ether, or dioxane and the solutions may be used an antiseptics, fungicides, larvicides and bactericides. Specification 645,425, [Group III], is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28005/53A GB763455A (en) | 1953-10-12 | 1953-10-12 | Improvements in addition compounds of amines and halides of aluminium and boron |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28005/53A GB763455A (en) | 1953-10-12 | 1953-10-12 | Improvements in addition compounds of amines and halides of aluminium and boron |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB763455A true GB763455A (en) | 1956-12-12 |
Family
ID=10268738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28005/53A Expired GB763455A (en) | 1953-10-12 | 1953-10-12 | Improvements in addition compounds of amines and halides of aluminium and boron |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB763455A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0377728A1 (en) * | 1988-06-24 | 1990-07-18 | Great Lakes Chemical Corp | Water soluble organic ammonium perhalides. |
-
1953
- 1953-10-12 GB GB28005/53A patent/GB763455A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0377728A1 (en) * | 1988-06-24 | 1990-07-18 | Great Lakes Chemical Corp | Water soluble organic ammonium perhalides. |
| EP0377728A4 (en) * | 1988-06-24 | 1990-12-12 | Great Lakes Chemical Corporation | Water soluble organic ammonium perhalides |
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