DE2156662A1 - Process for the production of crystal violet lactone - Google Patents
Process for the production of crystal violet lactoneInfo
- Publication number
- DE2156662A1 DE2156662A1 DE19712156662 DE2156662A DE2156662A1 DE 2156662 A1 DE2156662 A1 DE 2156662A1 DE 19712156662 DE19712156662 DE 19712156662 DE 2156662 A DE2156662 A DE 2156662A DE 2156662 A1 DE2156662 A1 DE 2156662A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- aqueous solution
- crystal violet
- violet lactone
- benzohydryl
- 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
- 238000000034 method Methods 0.000 title claims description 14
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- -1 Aminophenyl Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- IDMRITGMIYGSQM-UHFFFAOYSA-N 6-(dimethylamino)-3,5-bis[4-(dimethylamino)phenyl]-3h-2-benzofuran-1-one Chemical compound C1=CC(N(C)C)=CC=C1C1C2=CC(C=3C=CC(=CC=3)N(C)C)=C(N(C)C)C=C2C(=O)O1 IDMRITGMIYGSQM-UHFFFAOYSA-N 0.000 description 1
- 241000840267 Moma Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- C07D307/885—3,3-Diphenylphthalides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Description
THE CLAYTON ANILINE COMPANY LIMITED - MANCHESTER /GBTHE CLAYTON ANILINE COMPANY LIMITED - MANCHESTER / GB
(Case l-7298/CLY 2 ( Case l-7298 / CLY 2
Verfahren zur Herstellung von Kristallviolettlacton.Process for the production of crystal violet lactone.
Die Erfindung betrifft ein Verfahren zur Herstellung von 3,5-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalid (Kristallviolettlacton). Kristallviolettlacton wird in Papierbeschichtungsmitteln zur Herstellung von kohlefreiera Kopierpapier verwendet.The invention relates to a method for producing 3,5-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide (Crystal violet lactone). Crystal violet lactone is used in paper coatings to make carbon-free Copy paper used.
209822/1071209822/1071
Bekannt sind Verfahren» nach denen Krietallviolettlacton dadurch hergestellt wird, daß man 2-/T, h' -»Bis (dlaothylamino)-benzhydryl7-5-<ilmethylanilnol)enzoesaure in wßßriger Mineralsäure mit Oxidationsmitteln wie z. B. Bleidioxid» KaliuRdichromat oder Kaliumperraanganat behandelt. Ein schwerwiegender Kachteil der Oxidation unter sauren Be* dingungen besteht darin» daß das zuerst gebildete Oxidations« produkt unter Bildung von dunkel gefärbten teerigen Produkten der weiteren Oxidation unterliegen kann. Ein anderes Verfahren xur Herstellung von Kristallvlölettlacton besteht darin» daß stan das obengenannte Vorprodukt unter alkalischen Bedingungen bei einer Temperatur ist Bereich von $0 bis 1250C an der Luft oxidiert (Patentschrift 1 039 ?04)· Dieses Oxidationsverfahren ist seitraubend, «s verlangt kostspielige und komplizierte Qerüte und fahrt hflufig dazu, daft das rohe Kristallvlolettlaoton in einer physikalischen Fora erhalten wird, dl« nur schwer auf ein Filter aufgebracht werden kann·Processes are known by which crystal violet lactone is prepared by adding 2- / T, h '- »bis (dlaothylamino) -benzhydryl7-5- <ilmethylanilnol) enzoic acid in aqueous mineral acid with oxidizing agents such as e.g. B. lead dioxide »potassium dichromate or potassium peranganate treated. A serious disadvantage of oxidation under acidic conditions is "that the oxidation product formed first can be subject to further oxidation with the formation of dark-colored tarry products. Another method xur producing Kristallvlölettlacton is "that stan the above-mentioned precursor under alkaline conditions at a temperature range is from $ 0 to 125 0 C in air oxidized (Patent 1039? 04) · This oxidation process is seitraubend," s requires costly and complicated issues and often leads to the fact that the crude crystal volet clay is obtained in a physical form that is difficult to apply to a filter.
der vorliegenden Erfindung wird Krlstallvlolettlaeton in hoben Ausbeuten dadurch erhalten, daß nan eine VasserstoffperoxidlSsung su einer Lösung eines Alkalisalses derof the present invention is Krlstallvlolettlaeton Obtained in high yields by adding a hydrogen peroxide solution to a solution of an alkali metal 2·/Τ, 4* «Bis (dimethylamine) »benshy dry l7-5-dlae thy lasinobenxoesäure bei einem pH im Bereich von 8 bis 12,$ und tlner Temperatur von 60 bis 10O0C sugibt, und aus diesem2 · / Τ, 4 * «bis (dimethylamine)» benshy dry l7-5-dlae thy lasinobenxoic acid at a pH in the range from 8 to 12, $ and an internal temperature of 60 to 10O 0 C sugibt, and from this
209822/1071209822/1071
Gemisch das gebildete Kristallviolettlaeton mit Hilfe bekannter Verfahren isoliert. Dieses Verfahren ist einfach und kann mit Hilfe einer gewöhnlichen Moma&lausrüstung ohne Anwendung τοπ Druck durchgeführt werden.The mixture Kristallviolettlaeton formed by known methods isolated. This procedure is simple and can be carried out with the help of ordinary Moma & l equipment without applying τοπ pressure.
In einer bevorzugten Ausführungsform des erfindungace« aS£en Verfahrens enthält die Lösung des Ausg&ngsiaaterials Isopropy!alkohol· Hierdurch wird die Form des entstehenden rohen Produktes wesentlich verbessert« Beispielsweise wird Isopropy!alkohol zweckmäßig in Mengen von etwa 5 bis 100 Gew„j£ des Alkallsalzes der a-^M-BisCdimethylainlno)-benzhydrylT^-KSlmethyiamincbensoeaaure verwendet.In a preferred embodiment of the invention A method contains the solution of the starting material Isopropy! Alcohol · This improves the shape of the resulting raw product significantly «For example Isopropyl alcohol is expediently used in amounts of about 5 to 100% by weight of the alkali salt of a- ^ M-bisCdimethylainlno) -benzhydrylT ^ -KSlmethyiamine- like acid used.
KristallviölettIacton ist in einem Gemisch aus Wasser und Isopropylalkohol praktisch anlöslich und kann deshalb aus diesem Oeisiech leicht dureh Filtrieren gewonnen werden.Crystal Violet lactone is in a mixture of water and Isopropyl alcohol is practically soluble and can therefore from this oil can easily be obtained by filtration.
Kachfolgend wird die Erfindung anhand eines Beispiels nüher erläutert·The invention is explained in more detail below using an example.
16 Teile 2-^Tr#<«-Ble(di»ethylamino)-benEhydryl7*«5-dijnethyl· aminebenzoesäure werden in Form einer rohen Paste in einem16 parts of 2- ^ Tr # <«- lead (di» ethylamino) -benehydryl7 * «5-dijnethylaminebenzoic acid are in the form of a crude paste in one
2098Z2/10712098Z2 / 1071
aua 170 Teilen Wasser, 9 Teilenaua 170 parts of water, 9 parts
und 7 Teilen Isopropylalkoholand 7 parts isopropyl alcohol
Dip Lösung wird auf 92°C erwßrmt und wiihrend eines äoitraur.is von 1 l/?. Stunden δ Tolle einor Jij^i^en Lösung von MaeBt%raVοίfparo2 ld Dip solution is warmed to 92 ° C and during a temperature of 1 liter. Hours δ Tolle einor Jij ^ i ^ en solution of MaeBt% raVοίfparo2 ld
Kohle fjucofflßt, das Gerciach euf 20°C aURekUhlt, das rohe Kristallviolottlaefcon durch Filtrieren entfernt und πIt k<cn Vfasffor alkalifrei gewaschen. Die rohp Paste (30 Tel 3e)t die 5(j Teile KristallvJolettlacton entijflltr k&nn in üblicher V/eise durch Unkrintallisation aus canorn arornitißtilien Lösungsmittel gereinigt werden, wobr-i 13,5 Teile Kristallviolettlacton mit einem Schmelzpunkt von 175 bis l'J'c C erhalten xferden. Charcoal is poured out, the scent is cooled to 20 ° C, the crude crystal violet bottle is removed by filtering and washed in cold water for alkali-free. The ROHP paste (30 Tel 3e) t 5 (j parts KristallvJolettlacton entijfllt r k nn in a conventional V / else be purified by Unkrintallisation from canorn arornitißtilien solvent WOBr-i 13.5 parts of crystal violet lactone having a melting point of 175 to l 'J' c C get xferden.
20 98 'ΠΙ 107 T20 98 'ΠΙ 107 T
6AD ORIGINAL6AD ORIGINAL
Claims (1)
Wasserstoffperoxyd zwischen 1:1 und 1:1,5 wählt.5. The method according to claim 1, characterized in that the molar ratio between the benzoate and the
Selects hydrogen peroxide between 1: 1 and 1: 1.5.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5481970 | 1970-11-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2156662A1 true DE2156662A1 (en) | 1972-05-25 |
| DE2156662B2 DE2156662B2 (en) | 1981-04-30 |
| DE2156662C3 DE2156662C3 (en) | 1982-04-15 |
Family
ID=10472172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712156662 Expired DE2156662C3 (en) | 1970-11-18 | 1971-11-15 | Process for the preparation of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide (crystal violet lactone) |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5628940B1 (en) |
| CH (1) | CH557403A (en) |
| DE (1) | DE2156662C3 (en) |
| FR (1) | FR2114819A5 (en) |
| GB (1) | GB1347467A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629937A1 (en) * | 1975-07-03 | 1977-02-03 | Kanzaki Paper Mfg Co Ltd | PROCESS FOR MANUFACTURING TRIARYL METHANE DERIVATIVES |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2835450C3 (en) * | 1978-08-12 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of 3,3-bis- (4-dimethylaminophenyl) -6-dimethylaminophthalide (crystal violet lactone) |
| JPS5919548B2 (en) * | 1979-02-14 | 1984-05-07 | 保土谷化学工業株式会社 | Improved production method of 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalide |
| JP2591618B2 (en) * | 1987-05-18 | 1997-03-19 | 山田化学工業株式会社 | Process for producing 3,3-bis- (4-dimethylaminophenyl) -6-dimethylaminophthalide |
| JPH0524531U (en) * | 1991-08-02 | 1993-03-30 | 富士特殊紙業株式会社 | Rice bag |
| CA2693892A1 (en) | 2007-07-18 | 2009-01-22 | Jonathan Campbell | Laser-sensitive coating formulation |
| KR101691898B1 (en) | 2008-10-23 | 2017-01-02 | 데이터레이즈 리미티드 | Heat absorbing additives |
| US9267042B2 (en) | 2008-10-27 | 2016-02-23 | Datalase Ltd. | Coating composition for marking substrates |
| MX354358B (en) | 2011-05-25 | 2018-02-28 | Tetra Laval Holdings & Finance | Improved near infrared absorbers. |
| WO2013098076A1 (en) | 2011-12-30 | 2013-07-04 | Tetra Laval Holdings & Finance S.A. | Laminated color forming composition |
-
1970
- 1970-11-18 GB GB1347467D patent/GB1347467A/en not_active Expired
-
1971
- 1971-11-11 CH CH1637871A patent/CH557403A/en not_active IP Right Cessation
- 1971-11-15 DE DE19712156662 patent/DE2156662C3/en not_active Expired
- 1971-11-17 FR FR7141193A patent/FR2114819A5/fr not_active Expired
- 1971-11-18 JP JP9201971A patent/JPS5628940B1/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts Bd. 63, (1965), S. 3091 d-e * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629937A1 (en) * | 1975-07-03 | 1977-02-03 | Kanzaki Paper Mfg Co Ltd | PROCESS FOR MANUFACTURING TRIARYL METHANE DERIVATIVES |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1347467A (en) | 1974-02-27 |
| FR2114819A5 (en) | 1972-06-30 |
| DE2156662C3 (en) | 1982-04-15 |
| CH557403A (en) | 1974-12-31 |
| DE2156662B2 (en) | 1981-04-30 |
| JPS5628940B1 (en) | 1981-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |