DE1493901A1 - Verfahren zur Herstellung von N-monohydroxyalkylierten tertiaeren Aminobenzolen - Google Patents
Verfahren zur Herstellung von N-monohydroxyalkylierten tertiaeren AminobenzolenInfo
- Publication number
- DE1493901A1 DE1493901A1 DE19651493901 DE1493901A DE1493901A1 DE 1493901 A1 DE1493901 A1 DE 1493901A1 DE 19651493901 DE19651493901 DE 19651493901 DE 1493901 A DE1493901 A DE 1493901A DE 1493901 A1 DE1493901 A1 DE 1493901A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- och
- radical
- patent application
- amino
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001448 anilines Chemical group 0.000 title description 7
- -1 aralkyl radical Chemical class 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 102100022958 Adenylate kinase 7 Human genes 0.000 claims 1
- 108050000848 Adenylate kinase 7 Proteins 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 26
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000009835 boiling Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- OHKDMYGHPZFZDG-UHFFFAOYSA-N n-benzyl-2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(NCC=2C=CC=CC=2)=C1 OHKDMYGHPZFZDG-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
- XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XJQYUBVMTIEXHL-UHFFFAOYSA-N C1=CC=C2C(C(O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 Chemical compound C1=CC=C2C(C(O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 XJQYUBVMTIEXHL-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 241000985694 Polypodiopsida Species 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241001116498 Taxus baccata Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006487 butyl benzyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229940058172 ethylbenzene Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HBURMPHNNVHZKM-UHFFFAOYSA-N n-benzyl-2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(NCC=2C=CC=CC=2)=C1 HBURMPHNNVHZKM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0056059 | 1965-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493901A1 true DE1493901A1 (de) | 1969-07-24 |
Family
ID=7227692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651493901 Pending DE1493901A1 (de) | 1965-05-08 | 1965-05-08 | Verfahren zur Herstellung von N-monohydroxyalkylierten tertiaeren Aminobenzolen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3489801A (enExample) |
| BE (1) | BE680700A (enExample) |
| CH (1) | CH472365A (enExample) |
| DE (1) | DE1493901A1 (enExample) |
| GB (1) | GB1148076A (enExample) |
| NL (1) | NL6605722A (enExample) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573606A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines |
| US2597247A (en) * | 1948-08-02 | 1952-05-20 | Smith Kline French Lab | Nu-substituted amino-ethanols |
| US2683719A (en) * | 1949-10-18 | 1954-07-13 | Smith Kline French Lab | Nu-(beta-phenoxyisopropyl) ethanolamines |
| US2599001A (en) * | 1950-09-02 | 1952-06-03 | Smith Kline French Lab | Nu, nu-disubstituted-beta-haloalkylamines |
| US2887477A (en) * | 1955-09-07 | 1959-05-19 | Eastman Kodak Co | 2-hydroxy-5-methylsulfonylphenylazodiphenylamine compounds |
| US3154535A (en) * | 1962-01-30 | 1964-10-27 | Deering Milliken Res Corp | Polyethyleneoxy azo fugitive tints |
| US3154534A (en) * | 1962-01-30 | 1964-10-27 | Deering Milliken Res Corp | Polyethyleneoxy azo fugitive tints |
| DE1224611B (de) * | 1963-09-25 | 1966-09-08 | Kalle Ag | Lichtempfindliches Kopiermaterial fuer die Diazotypie mit 2, 5-Dialkoxy-4-tert.-aminobenzol-diazoniumsalzen |
| US3337525A (en) * | 1964-06-05 | 1967-08-22 | Deering Milliken Res Corp | (hydroxyethyl polyethyleneoxyamino)-phenylazo naphthalen-1, 8-diols |
-
1965
- 1965-05-08 DE DE19651493901 patent/DE1493901A1/de active Pending
-
1966
- 1966-04-28 NL NL6605722A patent/NL6605722A/xx unknown
- 1966-05-05 US US553600A patent/US3489801A/en not_active Expired - Lifetime
- 1966-05-06 BE BE680700D patent/BE680700A/xx unknown
- 1966-05-06 GB GB20088/66A patent/GB1148076A/en not_active Expired
- 1966-05-06 CH CH661266A patent/CH472365A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1148076A (en) | 1969-04-10 |
| BE680700A (enExample) | 1966-11-07 |
| NL6605722A (enExample) | 1966-11-10 |
| CH472365A (de) | 1969-05-15 |
| US3489801A (en) | 1970-01-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1569816A1 (de) | Verfahren zur Herstellung neuer Farbstoffe | |
| DE2855764A1 (de) | Verfahren zur herstellung von nitrodiarylamin unter verwendung eines promotors | |
| DE3639752C2 (de) | Verfahren zur Herstellung von amphoteren oberflächenaktiven Agentien | |
| DE1493901A1 (de) | Verfahren zur Herstellung von N-monohydroxyalkylierten tertiaeren Aminobenzolen | |
| DE2451219B2 (de) | Verfahren zur herstellung konzentrierter loesungen von farbstoffen und farbstoffzwischenprodukten und verwendung der loesungen | |
| DE946830C (de) | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe | |
| EP0056574B1 (de) | Naphtholsulfonsäureverbindungen, ihre Herstellung und Verwendung als Kupplungskomponenten | |
| DE2007372A1 (de) | Verfahren zur Herstellung von beta Acyloxyathyl ammoniumsalzen | |
| DE2065365B2 (de) | 1,3-disubstituierte Azetidine sowie Verfahren zu deren Herstellung und ihre Anwendung | |
| DE2751784A1 (de) | Azofarbstoffe | |
| DE1242603B (de) | Verfahren zur Herstellung von 5-Hydroxy-5-aminoalkyl-di-benzo-[a, d]-cycloheptanen | |
| DE69516715T2 (de) | Herstellung von n-(3-halopropyl)iminostilben und seine umsetzung in opipramol | |
| DE1695667A1 (de) | Neue Pyrrolderivate,deren Herstellung und deren Verwendung | |
| DE1543885C3 (de) | Verfahren zur Herstellung von 2-Methoxy^-amino-S-chlorbenzoesäuremethylester | |
| EP0037975B1 (de) | Neue Schwefelfarbstoffe der Carbazolreihe, ihre Herstellung und Verwendung sowie neue Zwischenprodukte | |
| EP0224789B1 (de) | Pyrazolinverbindungen | |
| DE3546858C2 (de) | Verfahren zur Herstellung von Ranitidin | |
| DE1593783A1 (de) | Verfahren zur Herstellung von 1-(2-Nitrilophenoxy)-2-hydroxy-3-isopropylaminopropan und dessen Salzen | |
| DE2631040A1 (de) | Verfahren zur herstellung basischer oxazinfarbstoffe | |
| DE2514553A1 (de) | Verfahren zur herstellung von propanolaminderivaten | |
| DE3516905C2 (enExample) | ||
| DE2827980C3 (de) | Reaktivfarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben von hydroxylgruppenhaltigen TextUfasern, Leder und Papier | |
| DE1059465B (de) | Verfahren zur Herstellung von Barbitursaeurederivaten | |
| AT368488B (de) | Verfahren zur herstellung von 2-substituierten 1-(2,6-dimethylphenoxy)-propanen | |
| DE3025549A1 (de) | Schwefelfarbstoffe, ihre herstellung und verwendung sowie zwischenprodukte zur herstellung der schwefelfarbstoffe |