AT30253B - Process for the preparation of 1-aminoanthraquinone and its alkyl or aryl derivatives substituted in the amino group. - Google Patents
Process for the preparation of 1-aminoanthraquinone and its alkyl or aryl derivatives substituted in the amino group.Info
- Publication number
- AT30253B AT30253B AT30253DA AT30253B AT 30253 B AT30253 B AT 30253B AT 30253D A AT30253D A AT 30253DA AT 30253 B AT30253 B AT 30253B
- Authority
- AT
- Austria
- Prior art keywords
- aminoanthraquinone
- alkyl
- preparation
- amino group
- derivatives substituted
- Prior art date
Links
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 title claims description 3
- 125000003277 amino group Chemical group 0.000 title claims description 3
- 125000003118 aryl group Chemical group 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LMJVMVCQHQVJDB-UHFFFAOYSA-N 1-(4-methylanilino)anthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O LMJVMVCQHQVJDB-UHFFFAOYSA-N 0.000 description 1
- COYPMBJUGCYPGT-UHFFFAOYSA-N 2-aminooxy-9,10-dioxoanthracene-1-sulfonic acid Chemical compound NOC1=C(C=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O)S(=O)(=O)O COYPMBJUGCYPGT-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von 1-Aminoanthrachinon und dessen in der Aminogruppe 8ubstituierten Alkyl- oder Arylderivaten.
EMI1.1
x-1l1onosulfosäuro die Sulfogruppe leicht durch den betreffenden stickstoffhaltigen Rest ersetzt werden kann.
EMI1.2
namlich z. B. neben der Substitution einer Sulfogruppe durch Ammoniak in einem an sich ganz analogen Fall die Bildung einer Aminooxyanthrachinonsulfosäurc ein (vgl. ssourcart, Bull. d. L Soc. Chim. d. Paris o3, 2 (U : Berichte 12, 141K). Bei der Einwirkung von Anilin auf Anthrachinon-ss-monosulfosäure (vgl. deutsches Reichs-Patent nr. 136872 der
EMI1.3
erhitzt.
Nach dem Erkalten hat sich das gebildete 1-Aminoanthrachinon in schonen Kristallen unmittelbar rein abgeschieden und kann durch Auswaschen mit heissem Wasser von etwa
EMI1.4
Beispiel 3 : 40 kg anthrachinon-α-monosulfosaures Kalium werden in einem emaillierten Rührwerksautoklaven mit 150 kg p-toluidin und 250 l Wasser während etwa
EMI1.5
in Natronlauge unlösliche Anteil liefert beim Umkristallisieren aus Pyridin und Methyl- alkohol das bekannte 1-p-Tolylaminoanthrachinon (deutsches Reichs-Patent Nr. 115048 li'. aux
<Desc / Clms Page number 1>
Process for the preparation of 1-aminoanthraquinone and its alkyl or aryl derivatives substituted in the amino group.
EMI1.1
x-1l1onosulfosäuro the sulfo group can easily be replaced by the nitrogen-containing radical in question.
EMI1.2
namely z. For example, in addition to the substitution of a sulfo group by ammonia, in a very analogous case, the formation of an aminooxyanthraquinone sulfonic acid (cf. ssourcart, Bull. In the case of the action of aniline on anthraquinone-ss-monosulphonic acid (see German Reich patent no. 136872 of
EMI1.3
heated.
After cooling down, the 1-aminoanthraquinone formed is deposited immediately in pure crystals in beautiful crystals and can be washed out with hot water for about
EMI1.4
Example 3: 40 kg of anthraquinone-α-monosulfonic acid potassium are in an enamelled stirred autoclave with 150 kg p-toluidine and 250 l of water for about
EMI1.5
When recrystallizing from pyridine and methyl alcohol, portions which are insoluble in sodium hydroxide solution produce the well-known 1-p-tolylaminoanthraquinone (German Reich patent no
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1902175024D DE175024C (en) | 1902-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT30253B true AT30253B (en) | 1907-10-10 |
Family
ID=5691720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT30253D AT30253B (en) | 1902-12-27 | 1906-07-13 | Process for the preparation of 1-aminoanthraquinone and its alkyl or aryl derivatives substituted in the amino group. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT30253B (en) |
-
1906
- 1906-07-13 AT AT30253D patent/AT30253B/en active
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