US2701811A - Reaction product of zinc oxide and aldonic acids - Google Patents
Reaction product of zinc oxide and aldonic acids Download PDFInfo
- Publication number
- US2701811A US2701811A US180500A US18050050A US2701811A US 2701811 A US2701811 A US 2701811A US 180500 A US180500 A US 180500A US 18050050 A US18050050 A US 18050050A US 2701811 A US2701811 A US 2701811A
- Authority
- US
- United States
- Prior art keywords
- solution
- zinc oxide
- gluconic acid
- resultant
- aldonic acids
- 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 title claims description 22
- 239000002253 acid Substances 0.000 title claims description 19
- 239000011787 zinc oxide Substances 0.000 title claims description 11
- 150000007513 acids Chemical class 0.000 title description 12
- 239000007795 chemical reaction product Substances 0.000 title description 7
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 24
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 13
- 235000012208 gluconic acid Nutrition 0.000 claims description 13
- 239000000174 gluconic acid Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000006228 supernatant Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 239000011670 zinc gluconate Substances 0.000 claims description 5
- 229960000306 zinc gluconate Drugs 0.000 claims description 5
- 235000011478 zinc gluconate Nutrition 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 239000011369 resultant mixture Substances 0.000 claims description 3
- 239000012265 solid product Substances 0.000 claims description 3
- 229950006191 gluconic acid Drugs 0.000 description 11
- 239000011701 zinc Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 238000009713 electroplating Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000007747 plating Methods 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
- -1 aldose sugars Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000001323 aldoses Chemical class 0.000 description 1
- 125000003180 beta-lactone group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052572 stoneware Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/10—Polyhydroxy carboxylic acids
- C07C59/105—Polyhydroxy carboxylic acids having five or more carbon atoms, e.g. aldonic acids
Definitions
- This invention relates to new and useful organic compounds and more particularly to the reaction products of aldonic acids with zinc oxide and to a method for the preparation thereof.
- Another object of the invention is to produce new and useful reaction products of zinc oxide andaldonic acids.
- a further object of the invention is the provision of a new and improved method for preparing compounds of the type referred to above.
- aldonic acids employed in this invention are derived from aldose sugars by oxidation thereof.
- suitable aldonic acids are known, e. g., gluconic, mannonic, galactonic and arabonic acids. 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 not, however, limited to the use of gluconic acid.
- gluconic acid employed in the practice of the invention exists in several forms and the invention contemplates the use of one or more of these forms or mixtures thereof including mixtures of the lactone forms.
- Commercial gluconic acid is available as a 50% aqueous solution of approximately 99% gluconic acid and 1% glucose. The presence of the glucose is undesirable because it tends to build up in a plating bath and thereby cause gumminess and stickiness in the bath.
- the zinc gluconate prepared according to this invention is substantially free of glucose. It is prepared by heating a commercial 50% gluconicacid solution to about 120 F. for a time sufiiciently long to melt any crystalline lactone that might be present. Then one mole of lead free zinc oxide is added for every two moles of gluconic acid present. The mixture is heated to 170 F. with agitation and held for ten minutes or until solution of the ingredients is complete. The resultant product is cooled to 120 F. in the liquid phase and poured into large stoneware ves- 2,701,811 Patented Feb. 8, 1955 sels and cooled until a waxy solid forms along with some supernatant liquor. The liquor is mainly glucose and water and is removed from the solid by filtration.
- the residue is placed in drying trays where it may be washed with ice water to remove traces of residual glucose.
- the product is then dried by heating at temperatures below 250 F. until it becomes dry and hard, after which it is ground in a hammer mill or other suitable means.
- the resultant product is stable and non-sticky.
- the zinc aldonate reaction product may be added to acid zinc electroplating baths according to the method outlined in my previously identified copending application in small amounts to effect a considerable increase in the brightness of the electroplated zinc plate. No further chemical treatment of the plates is necessary to bring out the brightness thereof.
- the reaction product also has it ptilronounced anti-burn efiect when added to zinc plating a ts.
- glucose when added alone to acid zinc plating baths, will not produce bright zinc plates.
- Glucose or other aldoses therefore are in no sense the equivalent of gluconic or other aldonic acids or the reaction products thereof with zinc oxide for the purpose of the present invention.
- a process of preparing an acid soluble zinc gluconate which comprises heating a 50% by weight aqueous solution of approximately 99% gluconic acid and 1% glucose to a temperature of about F. for a time sutficiently long to melt any crystalline lactone, then adding to said solution one mole of lead free zinc oxide for every two moles of gluconic acid present in the solution, heating the resultant mixture to F. with agitation until solution of the added ingredients is complete, cooling the resultant product to about 120 F. in the liquid phase, pouring the resultant liquid into vessels and further cooling until a waxy solid forms along with some supernatant liquor, removing the supernatant liquor, washing the residual solid with water and drying the washed solid product at temperatures below 250 F.
- a process of preparing an acid soluble zinc gluconate which comprises heating an aqueous solution of gluconic acid containing minor amounts of glucose to a temperature and for a time sufiiciently long to melt any crystalline lactone, then adding to said solution approximately one mole of lead free zinc oxide for every two moles of gluconic acid present in the solution, heating the resultant mixture with agitation until solution of the added ingredients is complete, cooling the resultant product in the liquod phase, pouring the resultant liquid into vessels, further cooling until a waxy solid forms along with some supernatant liquor, removing the supernatant liquor and drying the solid product.
Description
United States Patent REACTION PRODUCT OF ZINC OXIDE AND ALDONIC ACIDS Allan E. Chester, Highland Park, Ill., assignor to Poor & Company, Chicago, 111., a corporation of Delaware No Drawing. Application August 19, 1950, Serial No. 180,500
2 Claims. (Cl. 260-429) This invention relates to new and useful organic compounds and more particularly to the reaction products of aldonic acids with zinc oxide and to a method for the preparation thereof.
This application is a continuation-in-part of my copending application, Serial No. 34,127, filed June 19, 1948, which matured into United States Patent 2,576,997.
It is an object of the invention to produce water soluble organic compounds which are substantially free from impurities.
Another object of the invention is to produce new and useful reaction products of zinc oxide andaldonic acids. A further object of the invention is the provision of a new and improved method for preparing compounds of the type referred to above.
Other objects and advantages of the invention will appear in the following disclosure.
In accordance with the invention it has been found that new and useful products are obtained by reacting zinc oxide with aldonic acids. The preferred products are acid soluble and are suitable for use in a number of ways, especially in electroplating baths and particularly in acid zinc electroplating baths. The preferred use of the products in electroplating baths is more fully described in my above-identified copending application.
The aldonic acids employed in this invention are derived from aldose sugars by oxidation thereof. A number of suitable aldonic acids are known, e. g., gluconic, mannonic, galactonic and arabonic acids. 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 not, however, limited to the use of gluconic acid.
The gluconic acid employed in the practice of the invention exists in several forms and the invention contemplates the use of one or more of these forms or mixtures thereof including mixtures of the lactone forms. Commercial gluconic acid is available as a 50% aqueous solution of approximately 99% gluconic acid and 1% glucose. The presence of the glucose is undesirable because it tends to build up in a plating bath and thereby cause gumminess and stickiness in the bath.
The zinc gluconate prepared according to this invention is substantially free of glucose. It is prepared by heating a commercial 50% gluconicacid solution to about 120 F. for a time sufiiciently long to melt any crystalline lactone that might be present. Then one mole of lead free zinc oxide is added for every two moles of gluconic acid present. The mixture is heated to 170 F. with agitation and held for ten minutes or until solution of the ingredients is complete. The resultant product is cooled to 120 F. in the liquid phase and poured into large stoneware ves- 2,701,811 Patented Feb. 8, 1955 sels and cooled until a waxy solid forms along with some supernatant liquor. The liquor is mainly glucose and water and is removed from the solid by filtration. The residue is placed in drying trays where it may be washed with ice water to remove traces of residual glucose. The product is then dried by heating at temperatures below 250 F. until it becomes dry and hard, after which it is ground in a hammer mill or other suitable means. The resultant product is stable and non-sticky.
The foregoing description of the preparation of zinc gluconate is adaptable to the preparation of zinc aldonates in general by heating together one mole of zinc oxide with approximately two moles of any of the aldonic acids.
The zinc aldonate reaction product may be added to acid zinc electroplating baths according to the method outlined in my previously identified copending application in small amounts to effect a considerable increase in the brightness of the electroplated zinc plate. No further chemical treatment of the plates is necessary to bring out the brightness thereof. The reaction product also has it ptilronounced anti-burn efiect when added to zinc plating a ts.
It should be noted that glucose, when added alone to acid zinc plating baths, will not produce bright zinc plates. Glucose or other aldoses therefore are in no sense the equivalent of gluconic or other aldonic acids or the reaction products thereof with zinc oxide for the purpose of the present invention.
The invention is hereby claimed as follows:
1. A process of preparing an acid soluble zinc gluconate which comprises heating a 50% by weight aqueous solution of approximately 99% gluconic acid and 1% glucose to a temperature of about F. for a time sutficiently long to melt any crystalline lactone, then adding to said solution one mole of lead free zinc oxide for every two moles of gluconic acid present in the solution, heating the resultant mixture to F. with agitation until solution of the added ingredients is complete, cooling the resultant product to about 120 F. in the liquid phase, pouring the resultant liquid into vessels and further cooling until a waxy solid forms along with some supernatant liquor, removing the supernatant liquor, washing the residual solid with water and drying the washed solid product at temperatures below 250 F.
2. A process of preparing an acid soluble zinc gluconate which comprises heating an aqueous solution of gluconic acid containing minor amounts of glucose to a temperature and for a time sufiiciently long to melt any crystalline lactone, then adding to said solution approximately one mole of lead free zinc oxide for every two moles of gluconic acid present in the solution, heating the resultant mixture with agitation until solution of the added ingredients is complete, cooling the resultant product in the liquod phase, pouring the resultant liquid into vessels, further cooling until a waxy solid forms along with some supernatant liquor, removing the supernatant liquor and drying the solid product.
Ben, vol. 49, pages 720-21, J our. of Chem. Soc. (London), 1880, pages 795-6.
Beilstein, vol. 3, 4th edition, 1921, page 544.
Claims (1)
- 2. A PROCESS OF PREPARING AN ACID SOLUBLE ZINC GLUCONATE WHICH COMPRISES HEATING AN AQUEOUS SOLUTION OF GLUCONIC ACID CONTAINING MINOR AMOUNTS OF GLUCOSE TO A TEMPERATURE AND FOR A TIME SUFFICIENTLY LONG TO MELT ANY CRYSTALLINE LACTONE, THEN ADDING TO SAID SOLUTION APPROXIMATELY ONE MOLE OF LEAD FREE ZINC OXIDE FOR EVERY TWO MOLES OF GLUCONIC ACID PRESENT IN THE SOLUTION, HEATING THE RESULTANT MIXTURE WITH AGITATION UNTIL SOLUTION OF THE ADDED INGREDIENTS IS COMPLETE, COOLING THE RESULTANT PRODUCT IN THE LIQUOD PHASE, POURING THE RESULTANT LIQUID INTO VESSELS, FURTHER COOLING UNTIL A WAXY SOLID FORMS ALONG WITH SOME SUPERNATANT LIQUOR, REMOVING THE SUPERNATANT LIQUOR AND DRYING THE SOLID PRODUCT.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US180500A US2701811A (en) | 1950-08-19 | 1950-08-19 | Reaction product of zinc oxide and aldonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US180500A US2701811A (en) | 1950-08-19 | 1950-08-19 | Reaction product of zinc oxide and aldonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2701811A true US2701811A (en) | 1955-02-08 |
Family
ID=22660687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US180500A Expired - Lifetime US2701811A (en) | 1950-08-19 | 1950-08-19 | Reaction product of zinc oxide and aldonic acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2701811A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053674A (en) * | 1960-06-09 | 1962-09-11 | Sonneborn Chemical And Refinin | Portland cement concrete adjuvant |
| EP0254486A1 (en) * | 1986-07-18 | 1988-01-27 | Stabra AG | Preparation of metal gluconates |
| US6448210B1 (en) | 1999-03-19 | 2002-09-10 | Johnsondiversey, Inc. | Liquid automatic dishwashing composition with glassware protection |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1893872A (en) * | 1930-06-03 | 1933-01-10 | Winthrop Chem Co Inc | Metal complex compound |
-
1950
- 1950-08-19 US US180500A patent/US2701811A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1893872A (en) * | 1930-06-03 | 1933-01-10 | Winthrop Chem Co Inc | Metal complex compound |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053674A (en) * | 1960-06-09 | 1962-09-11 | Sonneborn Chemical And Refinin | Portland cement concrete adjuvant |
| EP0254486A1 (en) * | 1986-07-18 | 1988-01-27 | Stabra AG | Preparation of metal gluconates |
| US6448210B1 (en) | 1999-03-19 | 2002-09-10 | Johnsondiversey, Inc. | Liquid automatic dishwashing composition with glassware protection |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: BRENT CHEMICALS CORPORATION, A CORP. OF DE. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:STAUFFER CHEMICAL COMPANY;REEL/FRAME:003837/0384 Effective date: 19810202 |