DE601996C - Verfahren zur Darstellung von Kondensationsprodukten aus Phloroglucin und primaeren aromatischen Aminen - Google Patents
Verfahren zur Darstellung von Kondensationsprodukten aus Phloroglucin und primaeren aromatischen AminenInfo
- Publication number
- DE601996C DE601996C DEI46329D DEI0046329D DE601996C DE 601996 C DE601996 C DE 601996C DE I46329 D DEI46329 D DE I46329D DE I0046329 D DEI0046329 D DE I0046329D DE 601996 C DE601996 C DE 601996C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- phloroglucinol
- phloroglucine
- oxybenzene
- aromatic amines
- 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
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 title claims description 30
- 229960001553 phloroglucinol Drugs 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 9
- 150000003142 primary aromatic amines Chemical class 0.000 title claims description 7
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- -1 3, 5 - Di - (nitrophenylamino) oxybenzenes Chemical class 0.000 description 4
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HIAYRDRZFTZQIJ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C(=C(C=C1)ON)ON)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C1=C(C(=C(C=C1)ON)ON)C1=CC=CC=C1 HIAYRDRZFTZQIJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CIUYJYRQKYGNQP-UHFFFAOYSA-N (3-nitrophenyl)methanamine Chemical compound NCC1=CC=CC([N+]([O-])=O)=C1 CIUYJYRQKYGNQP-UHFFFAOYSA-N 0.000 description 1
- QFXJYJSYVMLCKA-UHFFFAOYSA-N (4-nitrophenoxy)methanamine Chemical compound NCOC1=CC=C([N+]([O-])=O)C=C1 QFXJYJSYVMLCKA-UHFFFAOYSA-N 0.000 description 1
- XASKKFXVYNAGJL-UHFFFAOYSA-N 1-N,3-N,5-N-tris(4-chlorophenyl)benzene-1,3,5-triamine Chemical compound ClC1=CC=C(C=C1)NC1=CC(=CC(=C1)NC1=CC=C(C=C1)Cl)NC1=CC=C(C=C1)Cl XASKKFXVYNAGJL-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- WWEXPFROUMQFIP-UHFFFAOYSA-N 2,4,6-triphenylbenzene-1,3,5-triamine Chemical compound NC1=C(C=2C=CC=CC=2)C(N)=C(C=2C=CC=CC=2)C(N)=C1C1=CC=CC=C1 WWEXPFROUMQFIP-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- SZXQDMFBQIEOAB-UHFFFAOYSA-N 4,5,6-triphenylbenzene-1,2,3-triamine Chemical compound C1(=CC=CC=C1)C1=C(C(=C(C(=C1N)N)N)C1=CC=CC=C1)C1=CC=CC=C1 SZXQDMFBQIEOAB-UHFFFAOYSA-N 0.000 description 1
- FOHHWGVAOVDVLP-UHFFFAOYSA-N 4-chloro-3-nitroaniline Chemical compound NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FOHHWGVAOVDVLP-UHFFFAOYSA-N 0.000 description 1
- ODVBBZFQPGORMJ-UHFFFAOYSA-N 4-nitrobenzylamine Chemical compound NCC1=CC=C([N+]([O-])=O)C=C1 ODVBBZFQPGORMJ-UHFFFAOYSA-N 0.000 description 1
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
- BUCZIOGWFDGHER-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)NC=1C(=C(C=CC1)NC1=CC=C(C=C1)[N+](=O)[O-])NC1=CC=C(C=C1)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)NC=1C(=C(C=CC1)NC1=CC=C(C=C1)[N+](=O)[O-])NC1=CC=C(C=C1)[N+](=O)[O-] BUCZIOGWFDGHER-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE613516D BE613516A (enrdf_load_stackoverflow) | 1933-01-21 | ||
| FR767500D FR767500A (enrdf_load_stackoverflow) | 1933-01-21 | ||
| DEI46329D DE601996C (de) | 1933-01-21 | 1933-01-21 | Verfahren zur Darstellung von Kondensationsprodukten aus Phloroglucin und primaeren aromatischen Aminen |
| DEI48483D DE613516C (de) | 1933-01-21 | 1933-12-02 | Verfahren zur Darstellung von Kondensationsprodukten |
| GB2181/34A GB415945A (en) | 1933-01-21 | 1934-01-22 | Manufacture of condensation products from phloroglucinol and aromatic amines |
| GB34699/34A GB448242A (en) | 1933-01-21 | 1934-12-03 | Manufacture of condensation products |
| FR45499D FR45499E (fr) | 1933-01-21 | 1934-12-03 | Procédé de préparation de produits de condensation à partir de phloroglucine et d'amines aromatiques |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI46329D DE601996C (de) | 1933-01-21 | 1933-01-21 | Verfahren zur Darstellung von Kondensationsprodukten aus Phloroglucin und primaeren aromatischen Aminen |
| DEI48483D DE613516C (de) | 1933-01-21 | 1933-12-02 | Verfahren zur Darstellung von Kondensationsprodukten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE601996C true DE601996C (de) | 1934-08-29 |
Family
ID=25943635
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI46329D Expired DE601996C (de) | 1933-01-21 | 1933-01-21 | Verfahren zur Darstellung von Kondensationsprodukten aus Phloroglucin und primaeren aromatischen Aminen |
| DEI48483D Expired DE613516C (de) | 1933-01-21 | 1933-12-02 | Verfahren zur Darstellung von Kondensationsprodukten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48483D Expired DE613516C (de) | 1933-01-21 | 1933-12-02 | Verfahren zur Darstellung von Kondensationsprodukten |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE613516A (enrdf_load_stackoverflow) |
| DE (2) | DE601996C (enrdf_load_stackoverflow) |
| FR (2) | FR45499E (enrdf_load_stackoverflow) |
| GB (2) | GB415945A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011254A1 (de) * | 1978-11-21 | 1980-05-28 | Bayer Ag | Verfahren zur Herstellung von Hydroxy-diphenylaminen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0402935A3 (en) * | 1989-06-16 | 1992-02-26 | Mitsui Petrochemical Industries, Ltd. | Method of producing n-alkylaminophenols |
| GB2358867B (en) * | 2000-02-03 | 2004-03-24 | Clive Stephen Delmonte | Three dimensional benzenoid polymer compositions and uses thereof |
-
0
- FR FR767500D patent/FR767500A/fr not_active Expired
- BE BE613516D patent/BE613516A/xx unknown
-
1933
- 1933-01-21 DE DEI46329D patent/DE601996C/de not_active Expired
- 1933-12-02 DE DEI48483D patent/DE613516C/de not_active Expired
-
1934
- 1934-01-22 GB GB2181/34A patent/GB415945A/en not_active Expired
- 1934-12-03 FR FR45499D patent/FR45499E/fr not_active Expired
- 1934-12-03 GB GB34699/34A patent/GB448242A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011254A1 (de) * | 1978-11-21 | 1980-05-28 | Bayer Ag | Verfahren zur Herstellung von Hydroxy-diphenylaminen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR767500A (enrdf_load_stackoverflow) | 1934-07-17 |
| GB448242A (en) | 1936-06-03 |
| FR45499E (fr) | 1935-09-12 |
| BE613516A (enrdf_load_stackoverflow) | |
| GB415945A (en) | 1934-09-06 |
| DE613516C (de) | 1935-05-20 |
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