GB744498A - Process for the production of diammonium compounds - Google Patents
Process for the production of diammonium compoundsInfo
- Publication number
- GB744498A GB744498A GB16190/53A GB1619053A GB744498A GB 744498 A GB744498 A GB 744498A GB 16190/53 A GB16190/53 A GB 16190/53A GB 1619053 A GB1619053 A GB 1619053A GB 744498 A GB744498 A GB 744498A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethoxy
- bis
- decane
- formula
- methyl
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- -1 piperidino, methylpiperidino, pyrrolidino, methyl-pyrrolidino, morpholino Chemical group 0.000 abstract 6
- 150000001450 anions Chemical class 0.000 abstract 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 abstract 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 abstract 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical group CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 abstract 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical class CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 abstract 1
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-Methylhexane Natural products CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 abstract 1
- PWPUPXJJCPIOGY-UHFFFAOYSA-N 4-(3-methylbutyl)morpholine Chemical compound CC(C)CCN1CCOCC1 PWPUPXJJCPIOGY-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 240000004760 Pimpinella anisum Species 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001649 bromium compounds Chemical class 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- DGUOMLICEVFHLS-UHFFFAOYSA-N decane;dihydrobromide Chemical compound Br.Br.CCCCCCCCCC DGUOMLICEVFHLS-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- KOOQJINBDNZUTB-UHFFFAOYSA-N n,n,3-trimethylbutan-1-amine Chemical compound CC(C)CCN(C)C KOOQJINBDNZUTB-UHFFFAOYSA-N 0.000 abstract 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- MHEMSXNXRWNGKW-UHFFFAOYSA-N tetradecane dihydrobromide Chemical compound Br.Br.CCCCCCCCCCCCCC MHEMSXNXRWNGKW-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of formula <FORM:0744498/IV(a)/1> where R1 and R2 are alkyl radicles of 1-4 carbon atoms or together with N form a piperidino, methylpiperidino, pyrrolidino, methyl-pyrrolidino, morpholino or methyl morpholino radicle, R is an alkyl radicle of 5-10 carbon atoms, m is 2-4, n is 6-14 and Anis a monovalent anion or a normal equivalent of a polyvalent anion. The compounds may be made by reacting a compound of formula <FORM:0744498/IV(a)/2> c.f. Specification 690,429, with 2 mols. of an alkyl halide of formula R-Hal; by reacting a compound of formula <FORM:0744498/IV(a)/3> with 2 mols. of an ester of formula R4-Hal, R4-O-SO2-OR4, or Aryl-SO2OR4, where R3 and R4 are alkyl radicles of 1-4 carbon atoms or by reacting a compound of formula <FORM:0744498/IV(a)/4> with 2 mols. of an amine of formula <FORM:0744498/IV(a)/5> and in all cases the anion of the product obtained may be subsequently exchanged for another anion. Representative of many ditertiary bisaminoalkoxy-alkanes specified for reaction are 1,6 - bis - (b - diethylamino - ethoxy) -, - (b - morpholino - ethoxy) - and - (g - dibutylaminopropoxy) - hexane, 1,6 - bis - (b - dimethylamino - ethoxy) - 3 - methyl - hexane, 1,7 - bis - (b - dimethylamino - ethoxy) - heptane, 1,8 - bis - (g - diethylamino - propoxy) - octane, 1,10-bis - (b - piperidino - and - morpholino - ethoxy) - decane, 1,10 - bis - (b - pyrrolidino - ethoxy)-decane hydrobromide, 1-(b -dimethylamino - ethoxy) - 10 - (g - diethylamino - propoxy) - decane and 1,14 - bis - (b - diethylamino - ethoxy)-tetradecane. Representative of specified halides of formula R-Hal are 2-amyl, 2-methyl-butyl-, isohexyl-, 3-methyl-pentyl-, 2-ethyl-hexyl- and n-decyl-chlorides, bromides and iodides. 1,10 - bis - [b - (n - amyl - methyl - amino) - ethoxy] - and - [g - (isoamyl - methylamino)-propoxy]-decane are specified starting materials for the second of the above processes. Representative of esters specified as containing R4 are methyl bromide, ethyl chloride, butyl bromide, dimethyl sulphate and p-toluene-sulphonic acid methyl ester. The products have an action similar to curane. In an example, 1,10 - bis - (b - dimethylamino - ethoxy)-decane is heated in acetone with isoamyl, n-amyl or n-hexyl bromide to yield the corresponding decane-dibromide and representative of many other products stated to be obtainable by a similar method are 1,6-bis-[g -(n-hexyldimethylammonium) - propoxy] - hexane - dimethosulphate, 1,8 - bis - [b - (isoamyl - dimethylammonium) - ethoxy] - octane - dichloride, 1,10 - bis - [b - (isoamyl - morpholinium) - ethoxy] - decane - di - bitartrate, 1,10-bis - [b - (n - octyl - dimethylammonium) - ethoxy] - decane - diiodide, 1,12 - bis - [b - (n - amyl - dimethylammonium) - ethoxy] - dodecane - dichloride and 1,14-bis-[b -(n-amyl-diethylammonium)-ethoxy], tetradecane-dibromide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH744498X | 1952-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB744498A true GB744498A (en) | 1956-02-08 |
Family
ID=4533383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16190/53A Expired GB744498A (en) | 1952-06-13 | 1953-06-12 | Process for the production of diammonium compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB744498A (en) |
-
1953
- 1953-06-12 GB GB16190/53A patent/GB744498A/en not_active Expired
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