US885577A - Process of making alizarin. - Google Patents
Process of making alizarin. Download PDFInfo
- Publication number
- US885577A US885577A US22392204A US1904223922A US885577A US 885577 A US885577 A US 885577A US 22392204 A US22392204 A US 22392204A US 1904223922 A US1904223922 A US 1904223922A US 885577 A US885577 A US 885577A
- Authority
- US
- United States
- Prior art keywords
- alizarin
- making
- anthraquinone
- caustic
- dissolve
- 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 - Lifetime
Links
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 title description 20
- 238000000034 method Methods 0.000 title description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 241000125205 Anethum Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 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 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
Definitions
- TonZZ whom it may concern:
- Alizarin of which the following is a specifi cation.
- My invention consists in the manufacture and production of alizarin in a very pure condition by the direct oxidation of anthra- 'quinone which has hitherto been considered impossible, the only process for the manufacture of alizarin hitherto practiced being to convert the anthraquinone into anthraquinone monosulfoacid and to pnri'y this, and then melt it with caustic alkali in the presence of an oxidizing agent.
- anthracpiinonc can be directly converted into alizarin by direct oxidation, by heating it with a highly concentrated aqueous solution of caustic alkali in the presence of an oxidizing agent.
- oxidizing agents I mention alkaline chlorates, alkaline nitrates,- sodium chro mate, the superoxids of sodium, barium,
- filtrate contains small quantities of benzoic a'cid. Decompose the recipitate by means of hydrochloric acid, lilter oil the residue from the solution of calcium chlorid and then dissolve the alizarin by means of dilute caustic soda solution, which leaves any anthraquinone undissolved.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
J'OHANN HEINRICH BONER, Ulr LITDWIUE Milt; SILK FE Unrrnn satires Parana ornrcn.
ANILIN AND SODA FABRIK, OF H PROCEsFi OF MAKING ALIZARIN.
Specification of Letters Patent.
Patented April 21, 1908.
Application filed September 9, 1904. Serial No. 223,922.
TonZZ whom it may concern:
I from by-products, which is obtained ac- Be itknown that l, JOiIANN llnmiucn cording to my invention.
BONER, doctorof philosophy and chemist, l
citizen of the Swiss Republic, residing at Ludwigslralen-on-thc-lthme, Bavaria, in the German Empire, have invented new and useful Improvements in Processes oi" Making;
Alizarin, of which the following is a specifi cation. I
My invention consists in the manufacture and production of alizarin in a very pure condition by the direct oxidation of anthra- 'quinone which has hitherto been considered impossible, the only process for the manufacture of alizarin hitherto practiced being to convert the anthraquinone into anthraquinone monosulfoacid and to pnri'y this, and then melt it with caustic alkali in the presence of an oxidizing agent.
I have now discovered that anthracpiinonc can be directly converted into alizarin by direct oxidation, by heating it with a highly concentrated aqueous solution of caustic alkali in the presence of an oxidizing agent. As examples of substances which can be used as oxidizing agents, I mention alkaline chlorates, alkaline nitrates,- sodium chro mate, the superoxids of sodium, barium,
- manganese, and lead and further ferric oxid;
lead oxid and mercury oxid or even atmospheric oxygen.
' The improvements which my invention shows ever the 'old method are twofold. In the first place, I have only to make use of one process to convert the anthraquinone into alizarin, Whereas according to the old method it is necessary to produce and-isolate an in-' ,termediate compound viz. anthraquinone l l r l latter when treated in the above manner yield in the filtrates coloring matters dyein shades of red dill'crcnt from those obtained on dyeing: with the precipitates. Alizarin, as dill'crcntiated from the product of the present invention is not herein claimed.
The following example illustrates the manner in which I prefer to carry out my invention, but I do not limit myself to this exampie. The parts are by weight.
Dissolve from twenty, to thirty, parts of p tassium chlorate in one hundred parts of water, and add three hundred parts of mixed caustic soda and caustic potash and then stir into the mixture one hundred parts of anthraquinonc. Heat and stir the whole (either in an o )en, or in a closed vessel, placed-in an oil about two hundred degrees centigrade, and
continue the heating until the oxidizing ma terial is used up. Dissolve the melt in water and blow an t irough the solution in order to reconvert to anthraquinone the oxanthranolv formed. Precipit-ate the alazarin by the addition of milk ol lime and filter it oil. The
bath) at a temperature ofv El[AFEN-(lN-THE-RIIINE, Gl lltlil'ANY, ASSIGNOR TO BADISCHE .\'-()N-'l\lllC-RIHNE, GERMANY, A CORPORATION.
filtrate contains small quantities of benzoic a'cid. Decompose the recipitate by means of hydrochloric acid, lilter oil the residue from the solution of calcium chlorid and then dissolve the alizarin by means of dilute caustic soda solution, which leaves any anthraquinone undissolved.
I claim:
1. The process of producing alizarin which consists in heating anthraquinon'e with caustic alkali in the presence of an oxidizing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22392204A US885577A (en) | 1904-09-09 | 1904-09-09 | Process of making alizarin. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22392204A US885577A (en) | 1904-09-09 | 1904-09-09 | Process of making alizarin. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US885577A true US885577A (en) | 1908-04-21 |
Family
ID=2954012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US22392204A Expired - Lifetime US885577A (en) | 1904-09-09 | 1904-09-09 | Process of making alizarin. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US885577A (en) |
-
1904
- 1904-09-09 US US22392204A patent/US885577A/en not_active Expired - Lifetime
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