DE2236777C2 - Verfahren zur Herstellung von Diaminodiphenyläthern - Google Patents
Verfahren zur Herstellung von DiaminodiphenyläthernInfo
- Publication number
- DE2236777C2 DE2236777C2 DE2236777A DE2236777A DE2236777C2 DE 2236777 C2 DE2236777 C2 DE 2236777C2 DE 2236777 A DE2236777 A DE 2236777A DE 2236777 A DE2236777 A DE 2236777A DE 2236777 C2 DE2236777 C2 DE 2236777C2
- Authority
- DE
- Germany
- Prior art keywords
- dimethylformamide
- aminophenol
- hydrogenated
- mixture
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 150000002170 ethers Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 60
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 5
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical class C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- -1 p-chloronitrobenzene Dimethylformamide Chemical compound 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 1
- MNBARIDWGOFKTJ-UHFFFAOYSA-M potassium;2-aminophenolate Chemical compound [K+].NC1=CC=CC=C1[O-] MNBARIDWGOFKTJ-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QJAIOCKFIORVFU-UHFFFAOYSA-N n,n-dimethyl-4-nitroaniline Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=C1 QJAIOCKFIORVFU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- FWEWPZKKHMLKFC-UHFFFAOYSA-M potassium;4-aminophenolate Chemical compound [K+].NC1=CC=C([O-])C=C1 FWEWPZKKHMLKFC-UHFFFAOYSA-M 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16486571A | 1971-07-26 | 1971-07-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2236777A1 DE2236777A1 (de) | 1973-02-08 |
| DE2236777C2 true DE2236777C2 (de) | 1984-05-10 |
Family
ID=22596412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2236777A Expired DE2236777C2 (de) | 1971-07-26 | 1972-07-26 | Verfahren zur Herstellung von Diaminodiphenyläthern |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5540573B1 (xx) |
| BE (1) | BE785589A (xx) |
| CA (1) | CA992991A (xx) |
| CH (1) | CH574906A5 (xx) |
| DE (1) | DE2236777C2 (xx) |
| FR (1) | FR2147681A5 (xx) |
| GB (1) | GB1334659A (xx) |
| IT (1) | IT960928B (xx) |
| NL (1) | NL178315C (xx) |
| SE (1) | SE403906B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539428A (en) * | 1982-05-10 | 1985-09-03 | Mallinckrodt, Inc. | Preparation of diaminodiphenyl ethers |
| US4551551A (en) * | 1982-09-27 | 1985-11-05 | Mallinckrodt, Inc. | Preparation of bis(aminophenyl) ethers from (N-acetyl)aminophenols or their phenolates |
| CN107162919B (zh) * | 2017-07-13 | 2019-03-19 | 山东冠森高分子材料科技股份有限公司 | 一种二氨基二苯醚的生产方法 |
| CN107188814A (zh) * | 2017-07-13 | 2017-09-22 | 山东冠森高分子材料科技股份有限公司 | 封闭无氧环境注氢还原制取二氨基二苯醚工艺 |
| CN111072503A (zh) * | 2019-12-28 | 2020-04-28 | 南通汇顺化工有限公司 | 一种制备3,4’-二氨基二苯醚的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3192263A (en) * | 1960-08-18 | 1965-06-29 | Du Pont | Production of dinitrophenyl and diaminophenyl ethers |
| DE1593871B2 (de) * | 1967-04-27 | 1976-08-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von nitroaminodiarylaethern |
-
1972
- 1972-06-14 CA CA144,720A patent/CA992991A/en not_active Expired
- 1972-06-29 BE BE785589A patent/BE785589A/xx not_active IP Right Cessation
- 1972-06-29 CH CH971772A patent/CH574906A5/xx not_active IP Right Cessation
- 1972-07-03 IT IT51305/72A patent/IT960928B/it active
- 1972-07-24 JP JP7405572A patent/JPS5540573B1/ja active Pending
- 1972-07-25 SE SE7209723A patent/SE403906B/xx unknown
- 1972-07-25 GB GB3480972A patent/GB1334659A/en not_active Expired
- 1972-07-26 FR FR7226931A patent/FR2147681A5/fr not_active Expired
- 1972-07-26 DE DE2236777A patent/DE2236777C2/de not_active Expired
- 1972-07-26 NL NLAANVRAGE7210310,A patent/NL178315C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA992991A (en) | 1976-07-13 |
| BE785589A (fr) | 1972-12-29 |
| JPS5540573B1 (xx) | 1980-10-18 |
| CH574906A5 (xx) | 1976-04-30 |
| GB1334659A (en) | 1973-10-24 |
| FR2147681A5 (xx) | 1973-03-09 |
| DE2236777A1 (de) | 1973-02-08 |
| SE403906B (sv) | 1978-09-11 |
| IT960928B (it) | 1973-11-30 |
| NL178315B (nl) | 1985-10-01 |
| NL178315C (nl) | 1986-03-03 |
| NL7210310A (xx) | 1973-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: MALLINCKRODT, INC. (N.D.GES.DES STAATES DELAWARE), |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: DERZEIT KEIN VERTRETER BESTELLT |
|
| 8339 | Ceased/non-payment of the annual fee |