DE2704964C2 - Verfahren zur Herstellung von Isoviolan thron - Google Patents
Verfahren zur Herstellung von Isoviolan thronInfo
- Publication number
- DE2704964C2 DE2704964C2 DE2704964A DE2704964A DE2704964C2 DE 2704964 C2 DE2704964 C2 DE 2704964C2 DE 2704964 A DE2704964 A DE 2704964A DE 2704964 A DE2704964 A DE 2704964A DE 2704964 C2 DE2704964 C2 DE 2704964C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- isoviolanthrone
- bromobenzanthrone
- potassium hydroxide
- butanol
- 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 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 42
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 26
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 claims description 20
- WVECFEIAZAKUNF-UHFFFAOYSA-N 3-bromobenzo[b]phenalen-7-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC3=C2C1=CC=C3Br WVECFEIAZAKUNF-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 10
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001256 steam distillation Methods 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- LCZJUUYGFMLYCS-UHFFFAOYSA-N 3-(7-oxobenzo[a]phenalen-3-yl)sulfanylbenzo[b]phenalen-7-one Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=CC=C1SC1=CC=C2C3=C1C=CC=C3C(=O)C1=CC=CC=C12 LCZJUUYGFMLYCS-UHFFFAOYSA-N 0.000 description 2
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000984 vat dye Substances 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
-
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/22—Dibenzanthrones; Isodibenzanthrones
- C09B3/24—Preparation by synthesis of the nucleus
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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2704964A DE2704964C2 (de) | 1977-02-07 | 1977-02-07 | Verfahren zur Herstellung von Isoviolan thron |
| FR7802394A FR2379503B1 (fr) | 1977-02-07 | 1978-01-27 | Procede de preparation de l'isoviolanthrone |
| IT19734/78A IT1091809B (it) | 1977-02-07 | 1978-01-27 | Processo per la preparazione di isolviolantrone |
| CH115178A CH635058A5 (en) | 1977-02-07 | 1978-02-02 | Process for the preparation of isoviolanthrone |
| GB4599/78A GB1594186A (en) | 1977-02-07 | 1978-02-06 | Manufacture of isoviolanthrone |
| JP1205378A JPS5398941A (en) | 1977-02-07 | 1978-02-07 | Preparation of isoviolanthrone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2704964A DE2704964C2 (de) | 1977-02-07 | 1977-02-07 | Verfahren zur Herstellung von Isoviolan thron |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2704964B1 DE2704964B1 (de) | 1978-06-29 |
| DE2704964C2 true DE2704964C2 (de) | 1979-02-15 |
Family
ID=6000520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2704964A Expired DE2704964C2 (de) | 1977-02-07 | 1977-02-07 | Verfahren zur Herstellung von Isoviolan thron |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5398941A (fr) |
| CH (1) | CH635058A5 (fr) |
| DE (1) | DE2704964C2 (fr) |
| FR (1) | FR2379503B1 (fr) |
| GB (1) | GB1594186A (fr) |
| IT (1) | IT1091809B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN169487B (fr) * | 1986-05-15 | 1991-10-26 | Ciba Geigy Ag | |
| CN114213226B (zh) * | 2021-12-29 | 2023-05-05 | 赤峰市恒祥化工有限公司 | 一种异紫蒽酮的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH129191A (de) * | 1927-08-31 | 1928-12-01 | Ig Farbenindustrie Ag | Verfahren zur Darstellung von Dichlorisodibenzanthron. |
| US2153312A (en) * | 1938-04-23 | 1939-04-04 | Du Pont | Process for the preparation of isodibenzanthrone |
| NL95611C (fr) * | 1938-11-24 |
-
1977
- 1977-02-07 DE DE2704964A patent/DE2704964C2/de not_active Expired
-
1978
- 1978-01-27 FR FR7802394A patent/FR2379503B1/fr not_active Expired
- 1978-01-27 IT IT19734/78A patent/IT1091809B/it active
- 1978-02-02 CH CH115178A patent/CH635058A5/de not_active IP Right Cessation
- 1978-02-06 GB GB4599/78A patent/GB1594186A/en not_active Expired
- 1978-02-07 JP JP1205378A patent/JPS5398941A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2704964B1 (de) | 1978-06-29 |
| IT1091809B (it) | 1985-07-06 |
| FR2379503A1 (fr) | 1978-09-01 |
| JPS5398941A (en) | 1978-08-29 |
| FR2379503B1 (fr) | 1985-06-14 |
| GB1594186A (en) | 1981-07-30 |
| CH635058A5 (en) | 1983-03-15 |
| IT7819734A0 (it) | 1978-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |