US2485564A - Reaction product of naphthylamine and aldonic acids - Google Patents
Reaction product of naphthylamine and aldonic acids Download PDFInfo
- Publication number
- US2485564A US2485564A US546438A US54643844A US2485564A US 2485564 A US2485564 A US 2485564A US 546438 A US546438 A US 546438A US 54643844 A US54643844 A US 54643844A US 2485564 A US2485564 A US 2485564A
- Authority
- US
- United States
- Prior art keywords
- naphthylamine
- aldonic
- aldonic acids
- acid
- product
- 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
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 title description 31
- 239000002253 acid Substances 0.000 title description 25
- 150000007513 acids Chemical class 0.000 title description 13
- 239000007795 chemical reaction product Substances 0.000 title description 8
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 14
- 235000012208 gluconic acid Nutrition 0.000 description 14
- 239000000174 gluconic acid Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000007747 plating Methods 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229910052793 cadmium Inorganic materials 0.000 description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 naphthylamine gluconates Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003180 beta-lactone group Chemical group 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- NHMJUOSYSOOPDM-UHFFFAOYSA-N cadmium cyanide Chemical compound [Cd+2].N#[C-].N#[C-] NHMJUOSYSOOPDM-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Definitions
- This invention relates to new and useful organic compounds, and more particularly reaction products of aldonic acids and amines and a method for the preparation thereof.
- One of the objects of the invention is to produce complex organic compounds which are soluble in alkaline solutions.
- Another object of the invention is to produce new and useful reaction products of amines and aldonic acids.
- a more specific object of the invention is the preparation of new and improved reaction products of aromatic amines and gluconic acid.
- Another specific object of the invention is the preparation of naphthylamine gluconates.
- Another object of the invention is the provision of a new and improved method for preparing compounds of the type referred to above. Other objects will appear hereinafter.
- new and useful products are obtained by reacting aldonic acids with amines, preferably aromatic amines, and particularly naphthylamines.
- the preferred products are alkalisoluble and are especially suitable for use in electroplating baths, that is, baths for the electrodeposition of metals, as, for example, zinc and cadmium.
- Our co-pending application Serial No. 546,439, filed of even date herewith describes alkaline cyanide cadmium plating baths containing products prepared in accordance with the present invention. It will be understood, however, that the products may be employed for many other purposes.
- Example A mixture was prepared by mixing together Parts Alpha naphthylamine 20 and 50% gluconic acid 120 The mixture was refluxed for two hours and. thereafter cooled. The resultant reaction product solidified on cooling.
- reaction products of amines with aldonic acids may be prepared by substituting other amines for the alpha naphthylamine in the foregoing example, and by substituting other aldonic acids for the gluconic acid.
- amines there may be mentioned other aromatic amines including beta naphthylamine and the various naphthalene di-amines.
- aldonic acids examples include mannonic, galactonic, and arabonic acids.
- the aldonic acids are derived from aldoses by oxidation.
- the products of the invention may be used as such, or they may be incorporated in organic solvents, as for example, monobutyl Carbitol, methyl Cellosolve Formal, and other similar water miscible organic solvents.
- aldonic acid In general, it is preferable to employ approximately equi-molecular proportions of aldonic acid and amine, or approximately 1 mole of aldonic acid for each primary or secondary amino group present in the amine. If desired, an excess of the aldonic acid may be employed.
- the temperature of reaction will vary with different types of amines, but good results have been obtained by employing temperatures at which concentrated aqueous solutions of the aldonic acid will reflux.
- Aldonic acids such as gluconic acid, are not obtained ordinarily in pure form but are usually prepared commercially as aqueous solutions containing around 50% of the acid, the concentration depending upon the maximum solubility of the aldonic acid in water.
- aldonic acids exist in alpha and beta lactone forms. Gluconic acid is preferred for the practice of this invention because it is more cheaply and readily available than the other aldonic acids.
- a method of preparing newv and useful chemical substances which comprises reacting' together an aldonic acid and alpha naphthylamine containing at least one amino group selected from the class consisting of primary :and secondary amino groups under the influence of heat, the quantity of the aldonic acid corresponding to at least one mol for each of said primary and secondary amino groups in said naphthylamine.
- a process of preparing new and useful. substances which comprises refluxing alpha naphthylamine with an aqueous solution of gluconic acid containing approximately 50% gluconic acid, the. quantities. of alpha naphthylamine and gluconic acid being approximately equi-molecular, and the resultant product on cooling being a solid.
- a process of preparing reaction products of alpha naphthylamine .and gluconic acid which comprises refluxing an aqueous solution'of gluconic acidwith alpha naphthylamine .for ap- 4 proximately 2 hours, the quantities of alpha naphthylamine and gluconic acid being approximately equi-molecular quantities, and the resultant product on cooling being a solid.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Oct. 25, 1949 REACTION PRODUCT OF NAPHTHYLAMIN E AND ALDONIC ACIDS Allan E. Chester, Highland Park, and Frederick F. Reisinger, Waukegan, Ill., assignors to Poor & Company, Chicago, 111., a corporation of Delaware No Drawing. Application July 24, 1944, Serial No. 546,438
8 Claims. (Cl. 260-501) This invention relates to new and useful organic compounds, and more particularly reaction products of aldonic acids and amines and a method for the preparation thereof.
One of the objects of the invention is to produce complex organic compounds which are soluble in alkaline solutions.
Another object of the invention is to produce new and useful reaction products of amines and aldonic acids.
A more specific object of the invention is the preparation of new and improved reaction products of aromatic amines and gluconic acid.
Another specific object of the invention is the preparation of naphthylamine gluconates.
Another object of the invention is the provision of a new and improved method for preparing compounds of the type referred to above. Other objects will appear hereinafter.
In accordance with the invention, it has been found that new and useful products are obtained by reacting aldonic acids with amines, preferably aromatic amines, and particularly naphthylamines. The preferred products are alkalisoluble and are especially suitable for use in electroplating baths, that is, baths for the electrodeposition of metals, as, for example, zinc and cadmium. Our co-pending application Serial No. 546,439, filed of even date herewith, describes alkaline cyanide cadmium plating baths containing products prepared in accordance with the present invention. It will be understood, however, that the products may be employed for many other purposes.
The invention will be further illustrated, but is not limited, by the following example in which the quantities are stated in parts by weight unless otherwise indicated:
Example A mixture was prepared by mixing together Parts Alpha naphthylamine 20 and 50% gluconic acid 120 The mixture was refluxed for two hours and. thereafter cooled. The resultant reaction product solidified on cooling.
When small amounts of this product were added to a cadmium plating bath in proportions within the range of 0.25 gram to 1 gram per gallon of bath, a considerable increase in brightness of the electrodeposited cadmium was noted. Furthermore, it was observed that this brighten ing effect could be obtained at current densities up to about 40 amperes per square foot without burning the electrodeposited metal. The alpha naphthylamine gluconate was soluble in the plating bath and did not tend to coagulate, decompose or otherwise deteriorate during the plating operation. Good results were also obtained when this product was incorporated with electrolytes used in barrel plating operations.
Other reaction products of amines with aldonic acids may be prepared by substituting other amines for the alpha naphthylamine in the foregoing example, and by substituting other aldonic acids for the gluconic acid. As examples of amines there may be mentioned other aromatic amines including beta naphthylamine and the various naphthalene di-amines.
Examples of other suitable aldonic acids, in addition to gluconic acid, are mannonic, galactonic, and arabonic acids. The aldonic acids are derived from aldoses by oxidation.
The products of the invention may be used as such, or they may be incorporated in organic solvents, as for example, monobutyl Carbitol, methyl Cellosolve Formal, and other similar water miscible organic solvents.
In general, it is preferable to employ approximately equi-molecular proportions of aldonic acid and amine, or approximately 1 mole of aldonic acid for each primary or secondary amino group present in the amine. If desired, an excess of the aldonic acid may be employed.
The temperature of reaction will vary with different types of amines, but good results have been obtained by employing temperatures at which concentrated aqueous solutions of the aldonic acid will reflux. Aldonic acids, such as gluconic acid, are not obtained ordinarily in pure form but are usually prepared commercially as aqueous solutions containing around 50% of the acid, the concentration depending upon the maximum solubility of the aldonic acid in water.
All of the aldonic acids exist in alpha and beta lactone forms. Gluconic acid is preferred for the practice of this invention because it is more cheaply and readily available than the other aldonic acids.
The invention is hereby claimed as follows:
1. The product of the reaction of approximately equimolecular proportions of alpha naphthylamine and an aqueous solution of an aldonic acid under refluxing conditions, which product upon cooling is a solid.
2. The product of the reaction of alpha naphthylamine and an aqueous solution of gluconic acid under reflux conditions, the quantity or the class consisting of primary and secondary amino groups under the influence of heat, the quantity of the aldonic acid correspondingxto at least one mol for each of said primary and-secondary amino groups in said naphthylamine.
4. A method of preparing newv and useful chemical substances which comprises reacting' together an aldonic acid and alpha naphthylamine containing at least one amino group selected from the class consisting of primary :and secondary amino groups under the influence of heat, the quantity of the aldonic acid corresponding to at least one mol for each of said primary and secondary amino groups in said naphthylamine.
5. A process of preparing new and useful. substances which comprises refluxing alpha naphthylamine with an aqueous solution of gluconic acid containing approximately 50% gluconic acid, the. quantities. of alpha naphthylamine and gluconic acid being approximately equi-molecular, and the resultant product on cooling being a solid.
6. The product of the reaction of alpha naphthylamine with gluconic acid in the presence of wateriunder. refluxing conditions, the quantities of. alpha naphthylamine and gluconic acid being approximately equi-molecular quantities, and the resultant product on cooling being a solid.
7. A process of preparing reaction products of alpha naphthylamine .and gluconic acid which comprises refluxing an aqueous solution'of gluconic acidwith alpha naphthylamine .for ap- 4 proximately 2 hours, the quantities of alpha naphthylamine and gluconic acid being approximately equi-molecular quantities, and the resultant product on cooling being a solid.
8. The product of the reaction of a naphthylamine containing amino groups from'the class consisting of primary and secondary amino groups and an aldonic acid in the presence of water under the influence of heat, the quantity .ofthe aldonic acid corresponding to at least one mol'for each of said amino groups in said naphthylamine andthe said product on cooling being a-solid.
ALLAN E. CHESTER. FREDERICK F. REISINGER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number. Name Date 1,901,565 Pasternack Mar. 14, 1933 2,114,122 Bruson. Apr. 12,1938 2,131,127. Ter Horst Sept. 27,1938 2,170,273 Morgan Aug. 22, 1939 2,211,630 Stuart Aug. 13,1940 2,212,831 Hoffmann Aug. 27, 1940 OTHER REFERENCES Chem. Abstracts, Vol.31, 7529, (1937) ibid:, vol. 32, 1402-1403 (1938).
Mathers et al.: Transactions of the'American Electrochemical Society, vol. 76(1939), pp. 371- 377.
Ching et al.: Transactions of the American Electrochemical Society, vol. 20 (1911), pp. 124- 125.
Beilstein, 4th ed, vol. XII, pp. 1220- and-11272.-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US546438A US2485564A (en) | 1944-07-24 | 1944-07-24 | Reaction product of naphthylamine and aldonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US546438A US2485564A (en) | 1944-07-24 | 1944-07-24 | Reaction product of naphthylamine and aldonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2485564A true US2485564A (en) | 1949-10-25 |
Family
ID=24180424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US546438A Expired - Lifetime US2485564A (en) | 1944-07-24 | 1944-07-24 | Reaction product of naphthylamine and aldonic acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2485564A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2725395A (en) * | 1951-12-21 | 1955-11-29 | Poor & Co | Oxyalkylated fatty amine salts of trifluoroacetic acid |
| US2739980A (en) * | 1951-12-19 | 1956-03-27 | Poor & Co | Salts of oxyalkylated fatty amines |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1901565A (en) * | 1930-07-19 | 1933-03-14 | Pfizer Charles & Co | Amides of d-gluconic acid |
| US2114122A (en) * | 1938-04-12 | Alcohols and process fob making | ||
| US2131127A (en) * | 1933-09-18 | 1938-09-27 | Us Rubber Co | Vulcanization of rubber |
| US2170273A (en) * | 1937-12-14 | 1939-08-22 | American Maize Prod Co | Adhesive composition |
| US2211630A (en) * | 1939-02-11 | 1940-08-13 | Lilly Co Eli | Ephedrine gluconate and process of producing it |
| US2212831A (en) * | 1938-04-25 | 1940-08-27 | Byk Guldenwerke Chem Fab A G | Manufacture of stable derivative of adrenaline |
-
1944
- 1944-07-24 US US546438A patent/US2485564A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2114122A (en) * | 1938-04-12 | Alcohols and process fob making | ||
| US1901565A (en) * | 1930-07-19 | 1933-03-14 | Pfizer Charles & Co | Amides of d-gluconic acid |
| US2131127A (en) * | 1933-09-18 | 1938-09-27 | Us Rubber Co | Vulcanization of rubber |
| US2170273A (en) * | 1937-12-14 | 1939-08-22 | American Maize Prod Co | Adhesive composition |
| US2212831A (en) * | 1938-04-25 | 1940-08-27 | Byk Guldenwerke Chem Fab A G | Manufacture of stable derivative of adrenaline |
| US2211630A (en) * | 1939-02-11 | 1940-08-13 | Lilly Co Eli | Ephedrine gluconate and process of producing it |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2739980A (en) * | 1951-12-19 | 1956-03-27 | Poor & Co | Salts of oxyalkylated fatty amines |
| US2725395A (en) * | 1951-12-21 | 1955-11-29 | Poor & Co | Oxyalkylated fatty amine salts of trifluoroacetic acid |
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