DE3005397A1 - Verbessertes verfahren zur herstellung von 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalid - Google Patents
Verbessertes verfahren zur herstellung von 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalidInfo
- Publication number
- DE3005397A1 DE3005397A1 DE19803005397 DE3005397A DE3005397A1 DE 3005397 A1 DE3005397 A1 DE 3005397A1 DE 19803005397 DE19803005397 DE 19803005397 DE 3005397 A DE3005397 A DE 3005397A DE 3005397 A1 DE3005397 A1 DE 3005397A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- bis
- azo
- catalyst
- aqueous solution
- 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
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 29
- 239000007864 aqueous solution Substances 0.000 claims description 26
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- -1 alkali metal salt Chemical class 0.000 claims description 10
- 239000003570 air Substances 0.000 claims description 9
- 150000004700 cobalt complex Chemical class 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001868 cobalt Chemical class 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 239000005749 Copper compound Substances 0.000 claims description 5
- 150000001869 cobalt compounds Chemical class 0.000 claims description 5
- 150000001880 copper compounds Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UXNOLMRPDQQINC-UHFFFAOYSA-N (2-hydroxyphenyl)-[2-[[(2-hydroxyphenyl)-sulfomethylidene]amino]ethylimino]methanesulfonic acid Chemical compound OC1=CC=CC=C1C(S(O)(=O)=O)=NCCN=C(S(O)(=O)=O)C1=CC=CC=C1O UXNOLMRPDQQINC-UHFFFAOYSA-N 0.000 claims description 3
- GFCKAAHPNWTBNI-UHFFFAOYSA-N (2-hydroxyphenyl)-[2-[[(2-hydroxyphenyl)-sulfomethylidene]amino]phenyl]iminomethanesulfonic acid Chemical compound OC1=CC=CC=C1C(S(O)(=O)=O)=NC1=CC=CC=C1N=C(S(O)(=O)=O)C1=CC=CC=C1O GFCKAAHPNWTBNI-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- ADPPSJHKROUSPZ-UHFFFAOYSA-N 3-hydroxy-4-[(2-hydroxy-5-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OC1=CC=C([N+]([O-])=O)C=C1N=NC1=C(O)C(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=C12 ADPPSJHKROUSPZ-UHFFFAOYSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- NFINRKWENNOUKO-UHFFFAOYSA-N 1-amino-6-hydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1(N)C=CC=CC1O NFINRKWENNOUKO-UHFFFAOYSA-N 0.000 claims 1
- GSMVBKWAHBCOIL-UHFFFAOYSA-N 1-formyl-6-hydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical compound OC1C=CC=CC1(C=O)S(O)(=O)=O GSMVBKWAHBCOIL-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- BQGGOSXJLSPVRH-UHFFFAOYSA-N 2-[bis[4-(dimethylamino)phenyl]methyl]-5-(dimethylamino)benzoic acid Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C(=CC(=CC=1)N(C)C)C(O)=O)C1=CC=C(N(C)C)C=C1 BQGGOSXJLSPVRH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- TYIHCISAZQHKHT-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3h-2-benzofuran-1-one Chemical compound C1=CC(N(C)C)=CC=C1C1C2=CC=C(N(C)C)C=C2C(=O)O1 TYIHCISAZQHKHT-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- IGLJWNJJOFKOTF-UHFFFAOYSA-N chembl2009321 Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1N=NC1=C(O)C=CC2=CC=CC=C12 IGLJWNJJOFKOTF-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- VVXLFFIFNVKFBD-UHFFFAOYSA-N 4,4,4-trifluoro-1-phenylbutane-1,3-dione Chemical compound FC(F)(F)C(=O)CC(=O)C1=CC=CC=C1 VVXLFFIFNVKFBD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/18—Preparation by oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54015002A JPS5919548B2 (ja) | 1979-02-14 | 1979-02-14 | ３，３−ビス−（４−ジメチルアミノフエニル）−６−ジメチルアミノフタリドの改良製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3005397A1 true DE3005397A1 (de) | 1980-08-28 |
| DE3005397C2 DE3005397C2 (en, 2012) | 1987-12-10 |
Family
ID=11876687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803005397 Granted DE3005397A1 (de) | 1979-02-14 | 1980-02-13 | Verbessertes verfahren zur herstellung von 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalid |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4271075A (en, 2012) |
| JP (1) | JPS5919548B2 (en, 2012) |
| DE (1) | DE3005397A1 (en, 2012) |
| GB (1) | GB2042577B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659053A (en) * | 1992-04-08 | 1997-08-19 | Basf Aktiengesellschaft | Preparation of Di- or triarylmethane dyes by oxidation |
| US5792879A (en) * | 1992-04-08 | 1998-08-11 | Basf Aktiengesellschaft | Preparation of DI-OR triarylmethane dyes by oxidation |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0753828B2 (ja) * | 1986-02-07 | 1995-06-07 | 山田化学工業株式会社 | ３，３−ビス−（４−ジメチルアミノフエニル）−６−ジメチルアミノフタリドの製造法 |
| JP2591618B2 (ja) * | 1987-05-18 | 1997-03-19 | 山田化学工業株式会社 | ３，３―ビス―（４―ジメチルアミノフェニル）―６―ジメチルアミノフタリドの製造法 |
| US5973168A (en) * | 1997-06-18 | 1999-10-26 | Mitsui Chemicals, Inc. | Preparation process of phthalide compound |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1347467A (en) * | 1970-11-18 | 1974-02-27 | Clayton Aniline Co Ltd | Process for the preparation of crystal biolet lactone |
| GB1395627A (en) * | 1971-08-04 | 1975-05-29 | Basf Ag | Catalytic oxidation of di-arylmethane and tri-arylmethane compounds |
| US4076728A (en) * | 1977-03-17 | 1978-02-28 | American Cyanamid Company | Process for manufacturing crystal violet lactone |
| JPH05278867A (ja) * | 1992-03-31 | 1993-10-26 | Eastman Kodak Japan Kk | 紙搬送装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5231384B1 (en, 2012) * | 1970-08-29 | 1977-08-15 | ||
| DE2557687A1 (de) * | 1975-12-20 | 1977-06-30 | Basf Ag | Verfahren zur herstellung von lactonen der triphenylmethanreihe |
-
1979
- 1979-02-14 JP JP54015002A patent/JPS5919548B2/ja not_active Expired
-
1980
- 1980-01-29 US US06/116,383 patent/US4271075A/en not_active Expired - Lifetime
- 1980-02-06 GB GB8003997A patent/GB2042577B/en not_active Expired
- 1980-02-13 DE DE19803005397 patent/DE3005397A1/de active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1347467A (en) * | 1970-11-18 | 1974-02-27 | Clayton Aniline Co Ltd | Process for the preparation of crystal biolet lactone |
| GB1395627A (en) * | 1971-08-04 | 1975-05-29 | Basf Ag | Catalytic oxidation of di-arylmethane and tri-arylmethane compounds |
| US4076728A (en) * | 1977-03-17 | 1978-02-28 | American Cyanamid Company | Process for manufacturing crystal violet lactone |
| JPH05278867A (ja) * | 1992-03-31 | 1993-10-26 | Eastman Kodak Japan Kk | 紙搬送装置 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659053A (en) * | 1992-04-08 | 1997-08-19 | Basf Aktiengesellschaft | Preparation of Di- or triarylmethane dyes by oxidation |
| US5792879A (en) * | 1992-04-08 | 1998-08-11 | Basf Aktiengesellschaft | Preparation of DI-OR triarylmethane dyes by oxidation |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2042577B (en) | 1983-02-23 |
| US4271075A (en) | 1981-06-02 |
| JPS55120562A (en) | 1980-09-17 |
| DE3005397C2 (en, 2012) | 1987-12-10 |
| JPS5919548B2 (ja) | 1984-05-07 |
| GB2042577A (en) | 1980-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |