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Publication numberUS1211413 A
Publication typeGrant
Publication dateJan 9, 1917
Filing dateJun 21, 1916
Priority dateJun 21, 1916
Publication numberUS 1211413 A, US 1211413A, US-A-1211413, US1211413 A, US1211413A
InventorsLee E H Cone
Original AssigneeDow Chemical Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Method of making indoxyl and derivatives.
US 1211413 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

UNITED STATES PATENT orFroE.

LEE E. H. CONE, OF MIDLAND, MICHIGAN, ASSIGNOR TO THE DOW CHEMICAL COMPANY, OF MIDLAND, MICHIGAN, A CORPORATION OF JMIIICI'IIGI-AN'. j

METHOD OF MAKING INDOX ,YL AND DERIVATIVES,

No Drawing.

To all whom it may concern:

Be it known that I, LEE E. H. Conn, a citizen of the United States, and a resident of Midland, county of Midland, and State 5 of Michigan, have-invented a new and useful Improvement in Methods of Making Indoxyl and Derivatives, of which the following is aspecification, the principle of the mvention being herein explained and the best mode in which I have contemplated applying that principle, from other inventions.

Heumannhimself developed an improvement in vhis original process for making indoxyl from phenyl-gly'cin orphenylglycocol, such improvement consisting in the use, insteadof caustic soda or caustic potash alone or mixed with one another, of either or both of these alkalis admixed with quicklime (see U. S. Patent 617 ,652). The expected effect of such addition of the quicklime was apparently to secure a higher yield of the desired indoxyl. With this same object in view, it has also been proposed to admix with the caustic alkalis used in treating the phenyl-glycin, a small proportion of metallic sodium or an equivalent proportion of another alkali metal (see British Patent No. 26,061 of 1901). Still another method for accomplishing this result is to add an alkaline oxid, specifically sodium oxid, to the melt (see U. S. Patents Nos. 727,270 and 756,l7l).

I have found upon attempting to utilize .35 the foregoing alleged improved processes,

that none gives satisfactory results, and that the yield of indoxyl, even under the most careful manipulation, still falls short of that theoretically possible. I have discovered,

40 however, that much more satisfactory results are obtained, where instead of adding either quicklime alone or such metallic alkali alone, to the melt of caustic alkalis, both of these'ingredients are added.

My improved process, characterized by the feature just explained, consists of the steps hereinafter fully ticularly pointed out in the claims, the following description setting forth only one method of carrying out my improved proc ess and-it being understood that various changes may be made therein, all within the scope of the invention.

carryin out my improved process as i tindicated, I rst prepare a so-called melt specification of Letters Patent.

V both potassium so as to distinguish it described and par- 4 Patented Jan. 9, 1917.

Application filed J nine 21, 1916. Serial No. 105,078.

of caustic alkalis consisting preferably of hydroxid and sodium 'hydroxid, and then add thereto a quantity of quicklime, together Witha smaller-quantity of metallic sodium. These admixed ingre clients are fused together under' conditions which leave the metallic sodium present as such, and in this condition-of the ,melt' I a quantity of a suitable phenyl-glycin body,

as for example, phenyl-glycin potassium as salt, is added thereto. The whole is maintained at a temperature of 250' C. fora half-hour or so, or until the reaction is complete. The mass while still fusedor molten is then poured or run into wa,t'e1', 'out of f contact with air, whereupon ,;the indoxyl goes into solution. I

a specific example for, he carrying out of the foregoing describ' process, I take 60 parts of potassium hy r'oxid, and 40 parts of sodium hydroxid, which gives a low melting point mixture, adding thereto 15 parts of the quicklime, and 3 parts of metallic sodium. The mixture thus produced is adapted'to react with 15 parts of the phenylso glycin potassium salt.

It will be understood that in place of the specified quicklime, other alkaline earth oxids, for example, strontium oxid or barium oxid, may be employed with sat sfactory results. It is essential, however, according to my process that the metallic sodium be present as such in the .fused mass,

' or melt, to which the phenyl-glycin body is p i added. It will, however, entirely disappear 9o during the reaction-with the latter, none iemaining in'the resultant product, if the proportion of eachmetal be properly chosen.

The foregoing improved process has been found in practice to give an entirely satisfactory yield of indoxyl, namely, from 65'. to 75 per cent. of that which should be secured according to the theory of the reaction.

of my invention may be employed instead of .the'one explained, change being made as regards the process herein disclosed,-provided the step or steps stated by any one of. the

following claims or the equivalent of such 1'05 derivatives, the istep which consists in heat- Other modes of applying the principle loo ing a phenyl-glycin body with a mixture derivatives, the step which consists in heat-- ing a phenyl-glycin body with a mixture of sodium and potassium hydroxids, lime and metallic sodium present as such, substantially as set forth.

4. In a method of making indoxyl and its derivatives, the steps which consist in first fusing together caustic alkali, alkaline-earth oxid andmetallic sodium, the latter remaining present as such; and then adding a phen l-glycin body to such mixture.

5. in a method of makingindox'yl derivatives, the steps which consist in fusing together a phenyl-glycin body with a mix and itsture of caustic alkali, alkaline-earth oxid and metallicsodium present as such; and then passing the resulting product, while still in fused state, into water. v

6. In a method of making indoxyl and its derivatives, the steps which consist in fusing together a phenyl-glycin body with a mixture of caustic alkali, alkaline-earth oxid and metallic sodium present as such; and then passing the resulting product, while still in fused state, into water, out of contact with air.

7 In a method'of making indoxyl and its derivatives, the steps which consist in first fusing together caustic alkali, alkaline-earth oxid and metallic sodium, the latter remaining present as such; adding a phenyl-glycinbody to such mixture; and then passing the resulting product, while still in used state, into water out of .contact with air.

Signed by me, this 19th da of June, 1916.

. LEE H. CONE. Attested by WM. W. Ross, Jr., ARTHUR N. Parnmnonn an at. potentmay be obtained for five cents each, by entrancing the "consioner e2 Patents,

' Washington, a. Q.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US6864210Feb 6, 2003Mar 8, 2005Equistar Chemicals, LpBimetallic olefin polymerization catalysts containing indigoid ligands
US20040157730 *Feb 6, 2003Aug 12, 2004Hlatky Gregory GBimetallic olefin polymerization catalysts containing indigoid ligands
Classifications
U.S. Classification548/489
Cooperative ClassificationC07D209/08