GB1013008A - Substituted anthraquinones - Google Patents
Substituted anthraquinonesInfo
- Publication number
- GB1013008A GB1013008A GB3407564A GB3407564A GB1013008A GB 1013008 A GB1013008 A GB 1013008A GB 3407564 A GB3407564 A GB 3407564A GB 3407564 A GB3407564 A GB 3407564A GB 1013008 A GB1013008 A GB 1013008A
- Authority
- GB
- United Kingdom
- Prior art keywords
- boric
- boric acid
- acid complex
- dichloroanthraquinone
- compounds
- 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
- 150000004056 anthraquinones Chemical class 0.000 title abstract 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 4
- 229960002645 boric acid Drugs 0.000 abstract 3
- 235000010338 boric acid Nutrition 0.000 abstract 3
- 239000004327 boric acid Substances 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- WYPZQZXSFVPVMI-UHFFFAOYSA-N 1,4-diamino-5,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(N)=CC=C2N WYPZQZXSFVPVMI-UHFFFAOYSA-N 0.000 abstract 1
- MEHLXACDLXEVBE-UHFFFAOYSA-N 1,4-dichloro-5,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(O)=CC=C2O MEHLXACDLXEVBE-UHFFFAOYSA-N 0.000 abstract 1
- IHFRLMPZDSBHDG-UHFFFAOYSA-N 1-amino-5,8-dichloro-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(O)=CC=C2N IHFRLMPZDSBHDG-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 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
-
- 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
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
- C09B1/10—Dyes containing halogen
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises the compounds 1,4-diamino - 5,8 - dichloroanthraquinone, 1-amino - 4 - hydroxy, 5,8 - dichloroanthraquinone and 2,5,8-trichloroquinizarin. These compounds, and 5,8-dichloroquinizarin are prepared by chlorinating a boric acid complex of the corresponding 1,4-substituted anthraquinone and subsequently hydrolysing the chlorinated boric acid complex to split off the boric-acid. Specified solvents used are concentrated sulphuric acid, oleum or chlorosulphonic acid and halogenating catalysts, which may be present in amounts of 0.1 to 5% by weight based on the boric acid complex, are iodine, sulphur monochloride and iron III salts. The process preferably takes place at 30 DEG to 120 DEG C. for 1 to 8 hours in a closed system. The hydrolysis step may be carried out using bisulphite.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF40552A DE1199279B (en) | 1963-08-21 | 1963-08-21 | Process for the preparation of anthraquinones chlorinated in the alpha position |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1013008A true GB1013008A (en) | 1965-12-15 |
Family
ID=7098283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3407564A Expired GB1013008A (en) | 1963-08-21 | 1964-08-20 | Substituted anthraquinones |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE651989A (en) |
| CH (1) | CH439330A (en) |
| DE (1) | DE1199279B (en) |
| FR (1) | FR1406210A (en) |
| GB (1) | GB1013008A (en) |
| NL (1) | NL6409118A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3161104D1 (en) * | 1980-04-22 | 1983-11-10 | Ciba Geigy Ag | Process for the preparation of oh or chloro derivatives of quinizarine bisubstituted in position 5 and 8 |
| DE3832740A1 (en) * | 1988-09-27 | 1990-04-05 | Basf Ag | METHOD FOR PRODUCING 1-AMINO-2-CHLORINE-4-HYDROXY-ANTHRACHINONE |
-
1963
- 1963-08-21 DE DEF40552A patent/DE1199279B/en active Granted
-
1964
- 1964-07-21 CH CH954464A patent/CH439330A/en unknown
- 1964-08-07 NL NL6409118A patent/NL6409118A/xx unknown
- 1964-08-14 FR FR985190A patent/FR1406210A/en not_active Expired
- 1964-08-19 BE BE651989D patent/BE651989A/xx unknown
- 1964-08-20 GB GB3407564A patent/GB1013008A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1406210A (en) | 1965-07-16 |
| DE1199279B (en) | 1965-08-26 |
| NL6409118A (en) | 1965-02-22 |
| BE651989A (en) | 1965-02-19 |
| DE1199279C2 (en) | 1966-03-24 |
| CH439330A (en) | 1967-07-15 |
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