DE3402983A1 - Verfahren zur orthoalkylierung von gegebenenfalls alkylsubstituierten m-phenylendiaminen - Google Patents
Verfahren zur orthoalkylierung von gegebenenfalls alkylsubstituierten m-phenylendiaminenInfo
- Publication number
- DE3402983A1 DE3402983A1 DE19843402983 DE3402983A DE3402983A1 DE 3402983 A1 DE3402983 A1 DE 3402983A1 DE 19843402983 DE19843402983 DE 19843402983 DE 3402983 A DE3402983 A DE 3402983A DE 3402983 A1 DE3402983 A1 DE 3402983A1
- Authority
- DE
- Germany
- Prior art keywords
- alloy
- weight
- aluminum
- substituted
- phenylenediamines
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 23
- 150000004988 m-phenylenediamines Chemical class 0.000 title claims description 16
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 32
- 229910000838 Al alloy Inorganic materials 0.000 claims description 24
- 229910001297 Zn alloy Inorganic materials 0.000 claims description 18
- 229910052782 aluminium Inorganic materials 0.000 claims description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 8
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 238000005804 alkylation reaction Methods 0.000 description 15
- 230000029936 alkylation Effects 0.000 description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000990 Ni alloy Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 4
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 4
- -1 aluminum anilide Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004998 toluenediamines Chemical class 0.000 description 2
- FJWZMLSQLCKKGV-UHFFFAOYSA-N 1-(2-ethylphenyl)propane-1,1-diamine Chemical class CCC1=CC=CC=C1C(N)(N)CC FJWZMLSQLCKKGV-UHFFFAOYSA-N 0.000 description 1
- XKBQWBOFFVJBHI-UHFFFAOYSA-N 1-ethylcyclohexa-3,5-diene-1,2-diamine Chemical compound CCC1(N)C=CC=CC1N XKBQWBOFFVJBHI-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843402983 DE3402983A1 (de) | 1984-01-28 | 1984-01-28 | Verfahren zur orthoalkylierung von gegebenenfalls alkylsubstituierten m-phenylendiaminen |
| EP85100427A EP0150770B1 (de) | 1984-01-28 | 1985-01-17 | Verfahren zur Orthoalkylierung von gegebenenfalls alkylsubstituierten m-Phenylendiaminen |
| DE8585100427T DE3560003D1 (en) | 1984-01-28 | 1985-01-17 | Process for the orthoalkylation of eventually alkyl-substituted meta-phenylenediamines |
| JP60009998A JPS60163847A (ja) | 1984-01-28 | 1985-01-24 | 随意アルキル‐置換のｍ‐フエニレンジアミンのオルト‐アルキル化法 |
| US06/860,144 US4760185A (en) | 1984-01-28 | 1986-05-06 | Process for the ortho-alkylation of optionally alkyl-substituted m-phenylenediamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843402983 DE3402983A1 (de) | 1984-01-28 | 1984-01-28 | Verfahren zur orthoalkylierung von gegebenenfalls alkylsubstituierten m-phenylendiaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3402983A1 true DE3402983A1 (de) | 1985-08-01 |
Family
ID=6226178
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843402983 Withdrawn DE3402983A1 (de) | 1984-01-28 | 1984-01-28 | Verfahren zur orthoalkylierung von gegebenenfalls alkylsubstituierten m-phenylendiaminen |
| DE8585100427T Expired DE3560003D1 (en) | 1984-01-28 | 1985-01-17 | Process for the orthoalkylation of eventually alkyl-substituted meta-phenylenediamines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585100427T Expired DE3560003D1 (en) | 1984-01-28 | 1985-01-17 | Process for the orthoalkylation of eventually alkyl-substituted meta-phenylenediamines |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4760185A (enExample) |
| EP (1) | EP0150770B1 (enExample) |
| JP (1) | JPS60163847A (enExample) |
| DE (2) | DE3402983A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0437788A1 (de) * | 1990-01-19 | 1991-07-24 | Bayer Ag | Verfahren zur Herstellung pulverförmiger Aluminiumlegierungen |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3834196A1 (de) * | 1988-10-07 | 1990-04-26 | Bayer Ag | Verfahren zur gewinnung alkylierter aromatischer amine |
| BR9005108A (pt) * | 1989-10-10 | 1991-09-17 | Dow Chemical Co | Metodo de preparacao de um catalisador,processo para a preparacao de aminas orto-alquiladas e catalisador |
| US5072047A (en) * | 1989-10-10 | 1991-12-10 | The Dow Chemical Company | Ortho-alkylation of aromatic amines |
| BR9005107A (pt) * | 1989-10-10 | 1991-09-17 | Dow Chemical Co | Processo para a preparacao de um catalisador,processo para a preparacao de aminas orto-alquiladas e catalisador |
| US5124483A (en) * | 1989-10-10 | 1992-06-23 | The Dow Chemical Company | Ortho-alkylation of aromatic amines |
| CN101417953A (zh) * | 2007-10-25 | 2009-04-29 | 杭州崇舜化学有限公司 | 一种二乙基甲苯二胺的合成方法 |
| CN106946714B (zh) * | 2017-03-16 | 2022-03-22 | 安阳工学院 | 一种二乙基甲苯二胺的合成工艺 |
| CN107999089B (zh) * | 2017-11-28 | 2021-02-02 | 万华化学集团股份有限公司 | 用于生产二乙基甲苯二胺的催化剂及其制备方法、应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA620573A (en) * | 1961-05-23 | Farbenfabriken Bayer Aktiengesellschaft | Process for the production of aromatic amines which are alkylated on the nucleus | |
| CA560990A (en) * | 1958-07-29 | Stroh Rudolf | Alkylation of aromatic amines | |
| DE1056138B (de) * | 1955-01-22 | 1959-04-30 | Bayer Ag | Verfahren zur Herstellung von kernalkylierten aromatischen Aminen |
| DE1051271B (de) * | 1955-01-22 | 1959-02-26 | Bayer Ag | Verfahren zur Herstellung von kernalkylierten aromatischen Aminen |
| US4436936A (en) * | 1981-06-19 | 1984-03-13 | Ciba-Geigy Corporation | Alkylation and aralkylation of aromatic amines |
-
1984
- 1984-01-28 DE DE19843402983 patent/DE3402983A1/de not_active Withdrawn
-
1985
- 1985-01-17 DE DE8585100427T patent/DE3560003D1/de not_active Expired
- 1985-01-17 EP EP85100427A patent/EP0150770B1/de not_active Expired
- 1985-01-24 JP JP60009998A patent/JPS60163847A/ja active Granted
-
1986
- 1986-05-06 US US06/860,144 patent/US4760185A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0437788A1 (de) * | 1990-01-19 | 1991-07-24 | Bayer Ag | Verfahren zur Herstellung pulverförmiger Aluminiumlegierungen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3560003D1 (en) | 1986-11-20 |
| JPH0220623B2 (enExample) | 1990-05-10 |
| EP0150770A3 (en) | 1985-08-28 |
| EP0150770A2 (de) | 1985-08-07 |
| JPS60163847A (ja) | 1985-08-26 |
| EP0150770B1 (de) | 1986-10-15 |
| US4760185A (en) | 1988-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |