GB433625A - The manufacture of aminoalkylated amines - Google Patents
The manufacture of aminoalkylated aminesInfo
- Publication number
- GB433625A GB433625A GB531134A GB531134A GB433625A GB 433625 A GB433625 A GB 433625A GB 531134 A GB531134 A GB 531134A GB 531134 A GB531134 A GB 531134A GB 433625 A GB433625 A GB 433625A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- diethylaminoethanol
- methoxy
- aniline
- sodium
- 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 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 16
- XFQXNCWPENNOBZ-UHFFFAOYSA-N 1-amino-2-ethylbutan-1-ol Chemical compound CCC(CC)C(N)O XFQXNCWPENNOBZ-UHFFFAOYSA-N 0.000 abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 9
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 8
- 150000003388 sodium compounds Chemical class 0.000 abstract 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 6
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 6
- 239000011734 sodium Substances 0.000 abstract 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 6
- YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 abstract 5
- 229910000149 boron phosphate Inorganic materials 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- 229910052708 sodium Inorganic materials 0.000 abstract 5
- YGGTVPCTAKYCSQ-UHFFFAOYSA-N 6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(N)=C21 YGGTVPCTAKYCSQ-UHFFFAOYSA-N 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 229960001413 acetanilide Drugs 0.000 abstract 3
- DPZKNWQVLDASPZ-UHFFFAOYSA-N n-(6-methoxyquinolin-8-yl)formamide Chemical compound N1=CC=CC2=CC(OC)=CC(NC=O)=C21 DPZKNWQVLDASPZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000011592 zinc chloride Substances 0.000 abstract 3
- 235000005074 zinc chloride Nutrition 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 150000003927 aminopyridines Chemical class 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- RRFMPCSQKFOUFO-UHFFFAOYSA-N 6-chloroquinolin-8-amine Chemical compound C1=CN=C2C(N)=CC(Cl)=CC2=C1 RRFMPCSQKFOUFO-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- IIBOGKHTXBPGEI-UHFFFAOYSA-N N-benzylformamide Chemical compound O=CNCC1=CC=CC=C1 IIBOGKHTXBPGEI-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000006004 Quartz sand Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 150000005022 aminoacridines Chemical class 0.000 abstract 1
- 150000005010 aminoquinolines Chemical class 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229940043430 calcium compound Drugs 0.000 abstract 1
- 150000001674 calcium compounds Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- GSEODROUOWOWFK-UHFFFAOYSA-N n',n'-diethyl-n-(6-methoxyquinolin-8-yl)ethane-1,2-diamine Chemical compound C1=CN=C2C(NCCN(CC)CC)=CC(OC)=CC2=C1 GSEODROUOWOWFK-UHFFFAOYSA-N 0.000 abstract 1
- GUZZRZFJWKNPHZ-UHFFFAOYSA-N n',n'-diethyl-n-methyl-n-phenylethane-1,2-diamine Chemical compound CCN(CC)CCN(C)C1=CC=CC=C1 GUZZRZFJWKNPHZ-UHFFFAOYSA-N 0.000 abstract 1
- QUMIGAREEPSVLG-UHFFFAOYSA-N n',n'-diethyl-n-phenylethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC=CC=C1 QUMIGAREEPSVLG-UHFFFAOYSA-N 0.000 abstract 1
- YUFVJWXSCSRIKJ-UHFFFAOYSA-N n',n'-diethyldodecane-1,12-diamine Chemical compound CCN(CC)CCCCCCCCCCCCN YUFVJWXSCSRIKJ-UHFFFAOYSA-N 0.000 abstract 1
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 abstract 1
- VDZUFVNIVVQEBG-UHFFFAOYSA-N n-(6-chloroquinolin-8-yl)-n',n'-diethylethane-1,2-diamine Chemical compound C1=CN=C2C(NCCN(CC)CC)=CC(Cl)=CC2=C1 VDZUFVNIVVQEBG-UHFFFAOYSA-N 0.000 abstract 1
- IPXGUHRVSUTXKJ-UHFFFAOYSA-N n-(6-methoxyquinolin-8-yl)acetamide Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)=O)=C21 IPXGUHRVSUTXKJ-UHFFFAOYSA-N 0.000 abstract 1
- VFXMWBGLBNFTSY-UHFFFAOYSA-N n-benzyl-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNCC1=CC=CC=C1 VFXMWBGLBNFTSY-UHFFFAOYSA-N 0.000 abstract 1
- LQVFVMJVCVOTJT-UHFFFAOYSA-N n-butyl-n',n'-diethylethane-1,2-diamine Chemical compound CCCCNCCN(CC)CC LQVFVMJVCVOTJT-UHFFFAOYSA-N 0.000 abstract 1
- RFOMHNNUBSJWIA-UHFFFAOYSA-N n-butyl-n'-phenylethane-1,2-diamine Chemical compound CCCCNCCNC1=CC=CC=C1 RFOMHNNUBSJWIA-UHFFFAOYSA-N 0.000 abstract 1
- NOCSAAHHSOQRCI-UHFFFAOYSA-N n-pyridin-2-ylformamide Chemical compound O=CNC1=CC=CC=N1 NOCSAAHHSOQRCI-UHFFFAOYSA-N 0.000 abstract 1
- GSBXXONXMOZQSW-UHFFFAOYSA-N n-pyridin-4-ylformamide Chemical compound O=CNC1=CC=NC=C1 GSBXXONXMOZQSW-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- WIPRQKODGRKUEW-UHFFFAOYSA-N rhodoquine Chemical compound C1=CN=C2C(NCCCN(CC)CC)=CC(OC)=CC2=C1 WIPRQKODGRKUEW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004576 sand Substances 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 229910001948 sodium oxide Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL36897D NL36897C (enrdf_load_stackoverflow) | 1934-02-17 | ||
| DER84867D DE602049C (de) | 1932-05-10 | 1932-05-10 | Verfahren zur Einfuehrung von Aminoalkylgruppen in basische Gruppen organischer Verbindungen |
| GB531134A GB433625A (en) | 1934-02-17 | 1934-02-17 | The manufacture of aminoalkylated amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB531134A GB433625A (en) | 1934-02-17 | 1934-02-17 | The manufacture of aminoalkylated amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB433625A true GB433625A (en) | 1935-08-19 |
Family
ID=9793707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB531134A Expired GB433625A (en) | 1932-05-10 | 1934-02-17 | The manufacture of aminoalkylated amines |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB433625A (enrdf_load_stackoverflow) |
| NL (1) | NL36897C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2313415A1 (fr) * | 1975-06-02 | 1976-12-31 | Texaco Development Corp | Procede pour preparer selectivement des polyalkylenepolyamines essentiellement non cycliques |
| FR2313379A1 (fr) * | 1975-06-02 | 1976-12-31 | Texaco Development Corp | Procede de preparation de n-(aminoalkyl) piperazines |
| FR2313352A1 (fr) * | 1975-06-02 | 1976-12-31 | Texaco Development Corp | Procede de preparation de polyalkylenepolyamines non cycliques |
-
0
- NL NL36897D patent/NL36897C/xx active
-
1934
- 1934-02-17 GB GB531134A patent/GB433625A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2313415A1 (fr) * | 1975-06-02 | 1976-12-31 | Texaco Development Corp | Procede pour preparer selectivement des polyalkylenepolyamines essentiellement non cycliques |
| FR2313379A1 (fr) * | 1975-06-02 | 1976-12-31 | Texaco Development Corp | Procede de preparation de n-(aminoalkyl) piperazines |
| FR2313352A1 (fr) * | 1975-06-02 | 1976-12-31 | Texaco Development Corp | Procede de preparation de polyalkylenepolyamines non cycliques |
Also Published As
| Publication number | Publication date |
|---|---|
| NL36897C (enrdf_load_stackoverflow) |
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