CH557795A - Verfahren zur nitrierung von anthrachinonen. - Google Patents

Verfahren zur nitrierung von anthrachinonen.

Info

Publication number: CH557795A
Authority: CH; Switzerland
Prior art keywords: nitration; nitroanthraquinone; anthraquinone; nitric acid; optionally substituted
Prior art date: 1971-10-26

Application number

CH1554271A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1971-10-26

Filing date

1971-10-26

Publication date

1975-01-15

Priority to BE790534D priority Critical patent/BE790534A/xx

1971-10-26 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1971-10-26 Priority to CH1554271A priority patent/CH557795A/de

1972-10-20 Priority to CS7200007081A priority patent/CS179973B2/cs

1972-10-23 Priority to PL1972158429A priority patent/PL89041B1/pl

1972-10-23 Priority to FR7237497A priority patent/FR2158918A5/fr

1972-10-24 Priority to IT53566/72A priority patent/IT972390B/it

1972-10-24 Priority to DE2252013A priority patent/DE2252013A1/de

1972-10-24 Priority to GB4902172A priority patent/GB1407700A/en

1972-10-24 Priority to DD166460A priority patent/DD99775A5/xx

1972-10-25 Priority to ES407942A priority patent/ES407942A1/es

1972-10-25 Priority to US05/300,689 priority patent/US3968130A/en

1972-10-25 Priority to NL7214440A priority patent/NL7214440A/xx

1972-10-26 Priority to JP47106707A priority patent/JPS5833218B2/ja

1975-01-15 Publication of CH557795A publication Critical patent/CH557795A/de

Links

NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 title claims description 20
YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 title claims description 19
238000006396 nitration reaction Methods 0.000 claims abstract description 45
150000004056 anthraquinones Chemical class 0.000 claims abstract description 40
239000000203 mixture Substances 0.000 claims abstract description 35
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 34
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 34
238000001816 cooling Methods 0.000 claims abstract description 10
239000011541 reaction mixture Substances 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims description 36
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 claims description 35
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 25
239000000047 product Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
239000013078 crystal Substances 0.000 claims description 8
239000012452 mother liquor Substances 0.000 claims description 4
239000002244 precipitate Substances 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
230000003134 recirculating effect Effects 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 5
230000035484 reaction time Effects 0.000 abstract description 7
238000004519 manufacturing process Methods 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 3
230000000802 nitrating effect Effects 0.000 abstract description 3
238000000926 separation method Methods 0.000 abstract description 2
ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 abstract 1
QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
239000007788 liquid Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000001226 reprecipitation Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
239000002699 waste material Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
DSTKZMAZXOPPAI-UHFFFAOYSA-N 1,5-dichloro-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] DSTKZMAZXOPPAI-UHFFFAOYSA-N 0.000 description 1
MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
XXUOKOYLVBHBCG-UHFFFAOYSA-N 1-hydroxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O XXUOKOYLVBHBCG-UHFFFAOYSA-N 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000009533 lab test Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
238000004886 process control Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000012795 verification Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1554271A 1971-10-26 1971-10-26 Verfahren zur nitrierung von anthrachinonen. CH557795A (de)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
BE790534D BE790534A (fr)	1971-10-26		Procede de nitration d'anthraquinones
CH1554271A CH557795A (de)	1971-10-26	1971-10-26	Verfahren zur nitrierung von anthrachinonen.
CS7200007081A CS179973B2 (en)	1971-10-26	1972-10-20	Method of producing anthraquinones
PL1972158429A PL89041B1 (cs)	1971-10-26	1972-10-23
FR7237497A FR2158918A5 (cs)	1971-10-26	1972-10-23
IT53566/72A IT972390B (it)	1971-10-26	1972-10-24	Procedimento per la nitrazione di atrachinoni
DE2252013A DE2252013A1 (de)	1971-10-26	1972-10-24	Verfahren zur nitrierung von anthrachinonen
GB4902172A GB1407700A (en)	1971-10-26	1972-10-24	Process for the nitration of anthraquinones
DD166460A DD99775A5 (cs)	1971-10-26	1972-10-24
ES407942A ES407942A1 (es)	1971-10-26	1972-10-25	Procedimiento para la preparacion de antraquinonas mononi- tradas en la posicion alfa.
US05/300,689 US3968130A (en)	1971-10-26	1972-10-25	Process for the nitration of anthraquinones
NL7214440A NL7214440A (cs)	1971-10-26	1972-10-25
JP47106707A JPS5833218B2 (ja)	1971-10-26	1972-10-26	アルフア − イチデモノニトロカサレタアントラキノンノセイホウ

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1554271A CH557795A (de)	1971-10-26	1971-10-26	Verfahren zur nitrierung von anthrachinonen.

Publications (1)

Publication Number	Publication Date
CH557795A true CH557795A (de)	1975-01-15

Family

ID=4409938

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1554271A CH557795A (de)	1971-10-26	1971-10-26	Verfahren zur nitrierung von anthrachinonen.

Country Status (2)

Country	Link
CH (1)	CH557795A (cs)
CS (1)	CS179973B2 (cs)

1971
- 1971-10-26 CH CH1554271A patent/CH557795A/de not_active IP Right Cessation
1972
- 1972-10-20 CS CS7200007081A patent/CS179973B2/cs unknown

Also Published As

Publication number	Publication date
CS179973B2 (en)	1977-12-30

Legal Events

Date	Code	Title	Description
1987-06-30	PL	Patent ceased

Publication	Publication Date	Title
CH434238A (de)	1967-04-30	Verfahren zur Herstellung neuer Tetracyclinverbindungen
DE2524747C3 (de)	1980-12-18	Verfahren zur Isolierung von 1,5-/1,8-Dinitroanthrachinon mit einem hohen Gehalt an a , a '-Duutroverbindungen
DE2162538A1 (de)	1972-07-06	Verfahren zur Herstellung von 1-Nitroanthrachinon
CH557795A (de)	1975-01-15	Verfahren zur nitrierung von anthrachinonen.
DE2248704C3 (de)	1985-04-04	Verfahren zur Herstellung von 1,5- und 1,8-Dinitroanthrachinonen und gegebenenfalls Trennung dieses Gemisches
DE2252013A1 (de)	1973-05-03	Verfahren zur nitrierung von anthrachinonen
DE2228660A1 (de)	1972-12-21	Verfahren zur Herstellung von ein heithchen alpha Monohydroxylamino oder alpha, alpha Dihydroxylaminoanthrachinon verbindungen
DE649165C (de)	1937-08-17	Verfahren zur Herstellung von Estern der Methacrylsaeure mit einwertigen Alkoholen
DE2346317C3 (de)	1980-06-19	Verfahren zur Herstellung von Dinitroanthrachinonen
CH619203A5 (en)	1980-09-15	Process for the concentration of haloanthraquinones
DE2646649C3 (de)	1982-01-28	Verfahren zur Mononitrierung von Anthrachinon
CH629176A5 (de)	1982-04-15	Verfahren zur herstellung von dinitroanthrachinon-gemischen mit hohem 1,5- und 1,8-dinitroanthrachinon-gehalt.
EP0009094B1 (de)	1982-04-14	Verfahren zur Herstellung von Methylenbrücken aufweisenden Polyarylaminen
DE2705106C3 (de)	1979-07-26	Verfahren zur Herstellung von 2-Amino-3-bromanthrachinon
DE2740403C2 (cs)	1987-07-23
DE2103360C (cs)	1973-06-20
CH640216A5 (de)	1983-12-30	Verfahren zur herstellung von 4-acylamido-2-nitro-1-alkoxybenzol-verbindungen.
DE2459164C3 (de)	1985-01-24	Verfahren zur Herstellung von Dinitroanthrachinongemischen, die einen hohen Gehalt an 1,5- und 1,8-Dinitroverbindungen aufweisen
EP0038777A1 (de)	1981-10-28	Verfahren zur Herstellung von in 5- und 8-Stellung bisubstituierten OH- oder Chlorderivaten des Chinizarins
DE562897C (de)	1932-11-01	Verfahren zur Herstellung von Derivaten der Benzol-, Naphthalin- und Acenaphthenreihen
DE337734C (de)	1921-06-04	Verfahren zur Darstellung von Nitroderivaten der ss-Azide der Anthrachinonreihe
DE2438210A1 (de)	1975-02-20	Verfahren zur nitrierung von anthrachinon und dessen derivaten
DE724760C (de)	1942-09-08	Verfahren zum Reiningen von 2íñ4íñ6-Trinitrophenyl-N-methylnitramin
EP0015486B1 (de)	1984-01-04	Verfahren zur Herstellung von 4,5-Dinitro-1,8-dihydroxyanthrachinon
DE2103360A1 (de)	1971-08-05	Verfahren zur Herstellung von I -Nitro anthrachinonen