FR2385684A1 - Procede de preparation de la 1-amino-2-bromo-4-hydroxyanthraquinone - Google Patents
Procede de preparation de la 1-amino-2-bromo-4-hydroxyanthraquinoneInfo
- Publication number
- FR2385684A1 FR2385684A1 FR7807963A FR7807963A FR2385684A1 FR 2385684 A1 FR2385684 A1 FR 2385684A1 FR 7807963 A FR7807963 A FR 7807963A FR 7807963 A FR7807963 A FR 7807963A FR 2385684 A1 FR2385684 A1 FR 2385684A1
- Authority
- FR
- France
- Prior art keywords
- amino
- hydroxyanthraquinone
- bromo
- degrees
- sulfuric acid
- 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.)
- Granted
Links
- MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004327 boric acid Substances 0.000 abstract 2
- 230000033444 hydroxylation Effects 0.000 abstract 2
- 238000005805 hydroxylation reaction Methods 0.000 abstract 2
- ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 abstract 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 abstract 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- FOMYGPSJEJGIPX-UHFFFAOYSA-N NC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.[Br] Chemical compound NC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.[Br] FOMYGPSJEJGIPX-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- -1 dibromo compound Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La 1-amino-2-bromo-4-hydroxyanthraquinone est préparée par hydroxylation de la 1-amino-2,4-dibromanthraquinone dans l'acide sulfurique concentré en présence d'acide borique à 110-130 degrés C et isolement du produit d'hydroxylation. On brome la 1-aminoanthraquinone dans l'acide sulfurique à 50-85 % entre 80 degrés C et 130 degrés C avec 1,5 à 2,1 molécules de brome par molécule de 1-aminoanthraquinone, on ajoute de l'oléum de manière à amener la concentration de l'acide sulfurique entre 96 % et 101 % (5 % SO3 ), on ajoute de l'acide borique et on hydroxyle le composé dibromé sans l'isoler. La 1-amino-2-bromo-4-hydroxyanthraquinone, très pure, est un produit intermédiaire dans la fabrication de colorants dispensables tels que la 1-amino-2-phénoxy-4-hydroxyanthraquinone et les 1-amino-2-alcoxy-4-hydroxyanthraquinones.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2713575A DE2713575C2 (de) | 1977-03-28 | 1977-03-28 | Verfahren zur Herstellung von 1-Amino-2-brom-4-hydroxyanthrachinon |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2385684A1 true FR2385684A1 (fr) | 1978-10-27 |
FR2385684B1 FR2385684B1 (fr) | 1983-07-18 |
Family
ID=6004853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7807963A Granted FR2385684A1 (fr) | 1977-03-28 | 1978-03-20 | Procede de preparation de la 1-amino-2-bromo-4-hydroxyanthraquinone |
Country Status (7)
Country | Link |
---|---|
US (1) | US4197250A (fr) |
JP (1) | JPS53120740A (fr) |
CH (1) | CH634823A5 (fr) |
DE (1) | DE2713575C2 (fr) |
FR (1) | FR2385684A1 (fr) |
GB (1) | GB1597323A (fr) |
IT (1) | IT1094954B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0190994A3 (en) * | 1985-02-04 | 1988-12-07 | Ciba-Geigy Ag | Process for the preparation of 1-amino-2-bromo-4-hydroxyanthraquinone |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6030304B2 (ja) * | 1977-04-26 | 1985-07-16 | 住友化学工業株式会社 | アントラキノン系中間物の製造法 |
US4292247A (en) * | 1977-04-25 | 1981-09-29 | Sumitomo Chemical Company, Limited | Process for producing anthraquinone intermediates |
JPS58118548A (ja) * | 1982-01-08 | 1983-07-14 | Sumitomo Chem Co Ltd | アントラキノン系中間物の製造方法 |
DE3415917A1 (de) * | 1984-04-28 | 1985-11-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1-amino-2-brom-4-hydroxyanthrachinon |
DE3841988A1 (de) * | 1988-12-14 | 1990-06-21 | Basf Ag | Verfahren zur herstellung von 1-amino-2-brom-4-hydroxy-anthrachinon |
JP5114901B2 (ja) * | 2006-09-15 | 2013-01-09 | コニカミノルタホールディングス株式会社 | 含窒素多環複素環化合物の製造方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE203083C (fr) * | 1906-12-24 | |||
US2604480A (en) * | 1947-08-29 | 1952-07-22 | Celanese Corp | 1-amino-2-bromo-4-hydroxy-anthraquinone by hydrolysis of 1-amino 2,4-dibrom anthraquinone |
JPS49120926A (fr) * | 1973-03-22 | 1974-11-19 | ||
DE2428337A1 (de) * | 1974-06-12 | 1975-12-18 | Basf Ag | Verfahren zur herstellung von 1-amino2-halogen-4-hydroxyanthrachinon |
-
1977
- 1977-03-28 DE DE2713575A patent/DE2713575C2/de not_active Expired
-
1978
- 1978-03-13 IT IT21189/78A patent/IT1094954B/it active
- 1978-03-16 US US05/887,219 patent/US4197250A/en not_active Expired - Lifetime
- 1978-03-20 FR FR7807963A patent/FR2385684A1/fr active Granted
- 1978-03-23 GB GB11618/78A patent/GB1597323A/en not_active Expired
- 1978-03-23 CH CH322178A patent/CH634823A5/de not_active IP Right Cessation
- 1978-03-28 JP JP3499178A patent/JPS53120740A/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE203083C (fr) * | 1906-12-24 | |||
US2604480A (en) * | 1947-08-29 | 1952-07-22 | Celanese Corp | 1-amino-2-bromo-4-hydroxy-anthraquinone by hydrolysis of 1-amino 2,4-dibrom anthraquinone |
JPS49120926A (fr) * | 1973-03-22 | 1974-11-19 | ||
DE2428337A1 (de) * | 1974-06-12 | 1975-12-18 | Basf Ag | Verfahren zur herstellung von 1-amino2-halogen-4-hydroxyanthrachinon |
Non-Patent Citations (1)
Title |
---|
CA1975 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0190994A3 (en) * | 1985-02-04 | 1988-12-07 | Ciba-Geigy Ag | Process for the preparation of 1-amino-2-bromo-4-hydroxyanthraquinone |
Also Published As
Publication number | Publication date |
---|---|
CH634823A5 (de) | 1983-02-28 |
US4197250A (en) | 1980-04-08 |
FR2385684B1 (fr) | 1983-07-18 |
GB1597323A (en) | 1981-09-03 |
DE2713575B1 (de) | 1978-10-12 |
JPS53120740A (en) | 1978-10-21 |
DE2713575C2 (de) | 1979-06-07 |
IT7821189A0 (it) | 1978-03-13 |
IT1094954B (it) | 1985-08-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |