US2033203A - Process of manufacturing aminoguanidine - Google Patents
Process of manufacturing aminoguanidine Download PDFInfo
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- US2033203A US2033203A US609043A US60904332A US2033203A US 2033203 A US2033203 A US 2033203A US 609043 A US609043 A US 609043A US 60904332 A US60904332 A US 60904332A US 2033203 A US2033203 A US 2033203A
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- US
- United States
- Prior art keywords
- aminoguanidine
- hydrogen
- nitroguanidine
- catalyst
- grams
- Prior art date
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- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 25
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000003139 buffering effect Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 3
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- -1 diphenylnitroguanidine Chemical compound 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- PRLAIRZQCMHFDC-UHFFFAOYSA-N 1-butyl-1-nitroguanidine Chemical compound CCCCN(C(N)=N)[N+]([O-])=O PRLAIRZQCMHFDC-UHFFFAOYSA-N 0.000 description 1
- VSQSLZDISBWTSD-UHFFFAOYSA-N 1-ethyl-1-nitroguanidine Chemical compound CCN(C(N)=N)[N+]([O-])=O VSQSLZDISBWTSD-UHFFFAOYSA-N 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
Definitions
- An object of this invention is an improved process of making substituted and unsubstituted aminoguanidines.
- a further object is to improve generally upon the manufacture of substituted and unsubstituted guanidines.
- these aminoguanidines can be produced very satisfactorily by the catalytic reduction of nitroguanidines.
- nitroguanidine is described in detail, the invention is applicable to substituted nitroguanidines in general, e. g. ditolylnitroguanidine, unsymmetrical diphenylnitroguanidine, xylylnitroguanidine, naphthylnitroguanidine, ethylnitroguanidine, butylnitroguanidine, triphenylnitroguanidine and like compounds.
- the reduction should be carried out with hydrogen in the presence of a catalyst at a relatively low temperature. It is advantageous to operate the process at temperatures such that the aminoguanidine will not be pyrolytically decomposed. It has been found also that if the hydrogenation is carried too far decomposition of the aminoguanidine results with consequent formation of urea and ammonia.
- a nickel catalyst and hydrogen are preferred for the reduction of the nitroguanidine.
- Other hydrogenating catalysts may, however, be used, for example metallic catalysts prepared in a finely divided condition.
- Suitable catalysts may be selected from the group of metals known as the hydrogenating metals, comprising the elements copper, nickel, iron and cobalt and the noble metals of the 8th group of the periodic table such as platinum and palladium, rhodium, or alloys of two or more of these metals.
- the temperature e. g., below 125 C. Temperatures between 25 C. and 85 C. are satisfactory and preferably the temperatures should be between and 85 C.
- aminoguanidine For the reason that acids and bases catalyze the decomposition of aminoguanidine it has been found that this may be "overcome by the addition of a buffering matriaLsuch as magnesium sulfate, mixtures of alkaline phosphates, or mixtures of borax with boric acid and sodium chloride, which serves to reduce'the decomposition. While carbondioxide neutralizes the aminoguanidine it is sufficiently acid in reaction to decompose it.
- a buffering matriaL such as magnesium sulfate, mixtures of alkaline phosphates, or mixtures of borax with boric acid and sodium chloride
- Example 1 A hydrogenation catalyst is prepared by suspending kieselguhr in a solution of nickel nitrate. Basic nickel carbonate is precipitated on the kieselguhr by adding sodium carbonate solution. The mass of kieselguhr and basic nickel carbonate is washed several times by decantation and filtered. The catalyst is then activated by reducing the basic nickel carbonate by means of hydrogen.
- nitroguanidine Ten and four tenths grams of nitroguanidine, 5 grams of the above catalyst, and 200 grams of water are placed in a steel reaction vessel capable of being heated.
- the reaction vessel is sealed, attached to a source of hydrogen, and heated to C. with good agitation under a hydrogen pressure of 1200 lbs. per sq. in. until the calculated amount of hydrogen has been absorbed.
- the reaction vessel is then unloaded.
- the aminoguanidine is recovered by filtering off the catalyst, evaporating the neutralized solution and precipitating the aminoguanidine as amino-- guanidine bicarbonate by addition of sodium bicarbonate.
- Example 2 Ten and four tenths grams of nitroguanidine and 5 grams of the catalyst described in Example 1 are suspended in 200 grams of water solution containing 7 grams of magnesium sulfate. The mixture is placed in a steel reaction vessel capable of being heated. The reaction vessel is sealed, attached to a supply of hydrogen, and heated to C. with good agitation under a hydrogen pressure of 800 lbs/sq. in. After the calculated amount of hydrogen has been absorbed, the reaction vessel is unloaded and the aminoguanidine isolated as described in Example 1.
- Example 3 Ten and four tenths grams of nitroguanidine and 5 grams of the catalyst described in Example 1 are suspended in 200 grams of ethyl acetate. The mixture is placed in a steel reaction vessel capable of being heated. The reaction vessel is sealed, attached to a supply of hydrogen,
- reaction vessel is unloaded and'the aminoguanidine isolated as described in Example 1.
- the resulting aminoguanidine may be isolated by filtration and neutralizing with dilute sulfuric acid. To the solution, after evaporation, is added potassium bicarbonate to precipitate the aminoguanidine. The solution may then be cooled, filtered, and the product dried.
- aminoguanidine which comprises the reduction of unsubstituted 10 nitroguanidine with hydrogen at a temperature between 25 C. and 125 C. in the presence of a hydrogenation metal catalyst and in the absence of any substantial amount of acids.
- aminoguanidine 15 which comprises reducing nitroguanidine by means of hydrogen in the presence of a hydrogenation metal catalyst and in the absence of any substantial amount of acids, operating the process at a pressure above 400 pounds per square 20 inch, and maintaining the temperature of the reaction between 25 C. and 125 C.
- the buffering material is a mixture of phosphates of the alkali metals.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Mar. 10, 1936 STATES PATENT or es PROCESS OF MANUFACTURING AMINOGUANIDINE No Drawing. Application May 3, 1932,
Serial No. 609,043
13 Claims.
dine by reducing nitroguanidine by means of zinc.
dust and. acetic acid. (Thiele Ann. 270, 20 (1898) 302, 333 (1898)). In such a method a large excess of zinc dust is used and for the reason that only 50% yields are obtainable this method has been regarded as unsatisfactory. Aminoguanidine has also been prepared from hydrazine and methylisothiourea but this method is also unsatisfactory because of the expensive reagents that are used.
An object of this invention is an improved process of making substituted and unsubstituted aminoguanidines. A further object is to improve generally upon the manufacture of substituted and unsubstituted guanidines. Other objects will appear hereinafter, as the description proceeds.
According to this invention these aminoguanidines can be produced very satisfactorily by the catalytic reduction of nitroguanidines. Although in the following discussion nitroguanidine is described in detail, the invention is applicable to substituted nitroguanidines in general, e. g. ditolylnitroguanidine, unsymmetrical diphenylnitroguanidine, xylylnitroguanidine, naphthylnitroguanidine, ethylnitroguanidine, butylnitroguanidine, triphenylnitroguanidine and like compounds.
According to this invention the reduction should be carried out with hydrogen in the presence of a catalyst at a relatively low temperature. It is advantageous to operate the process at temperatures such that the aminoguanidine will not be pyrolytically decomposed. It has been found also that if the hydrogenation is carried too far decomposition of the aminoguanidine results with consequent formation of urea and ammonia.
For the purpose of this invention a nickel catalyst and hydrogen are preferred for the reduction of the nitroguanidine. Other hydrogenating catalysts may, however, be used, for example metallic catalysts prepared in a finely divided condition. Suitable catalysts may be selected from the group of metals known as the hydrogenating metals, comprising the elements copper, nickel, iron and cobalt and the noble metals of the 8th group of the periodic table such as platinum and palladium, rhodium, or alloys of two or more of these metals. In this process it has been found desirable to keep the temperature as low as possible to prevent decomposition, e. g., below 125 C. Temperatures between 25 C. and 85 C. are satisfactory and preferably the temperatures should be between and 85 C. Also it is preferred to operate the process at such pressures as will permit the hydrogenation to proceed at a rate in excess of the rate of decomposition of the products. Suitable results may be obtained at a hydrogen pressure above 400 lbs. per sq. in. Lower pressures lead to incomplete conversion and the excessive formation of by-products. Good. results have been obtained when operating the process at a pressure of about 1100 lbs. per sq. in., although higher pressures even as high as 3000 lbs. /-sq. in. may be used in some cases. For the reason that acids and bases catalyze the decomposition of aminoguanidine it has been found that this may be "overcome by the addition of a buffering matriaLsuch as magnesium sulfate, mixtures of alkaline phosphates, or mixtures of borax with boric acid and sodium chloride, which serves to reduce'the decomposition. While carbondioxide neutralizes the aminoguanidine it is sufficiently acid in reaction to decompose it.
The following examples are given as specific embodiments which further illustrate my invention:
Example 1 A hydrogenation catalyst is prepared by suspending kieselguhr in a solution of nickel nitrate. Basic nickel carbonate is precipitated on the kieselguhr by adding sodium carbonate solution. The mass of kieselguhr and basic nickel carbonate is washed several times by decantation and filtered. The catalyst is then activated by reducing the basic nickel carbonate by means of hydrogen.
Ten and four tenths grams of nitroguanidine, 5 grams of the above catalyst, and 200 grams of water are placed in a steel reaction vessel capable of being heated. The reaction vessel is sealed, attached to a source of hydrogen, and heated to C. with good agitation under a hydrogen pressure of 1200 lbs. per sq. in. until the calculated amount of hydrogen has been absorbed. The reaction vessel is then unloaded. The aminoguanidine is recovered by filtering off the catalyst, evaporating the neutralized solution and precipitating the aminoguanidine as amino-- guanidine bicarbonate by addition of sodium bicarbonate.
Example 2 Ten and four tenths grams of nitroguanidine and 5 grams of the catalyst described in Example 1 are suspended in 200 grams of water solution containing 7 grams of magnesium sulfate. The mixture is placed in a steel reaction vessel capable of being heated. The reaction vessel is sealed, attached to a supply of hydrogen, and heated to C. with good agitation under a hydrogen pressure of 800 lbs/sq. in. After the calculated amount of hydrogen has been absorbed, the reaction vessel is unloaded and the aminoguanidine isolated as described in Example 1.
Example 3 Ten and four tenths grams of nitroguanidine and 5 grams of the catalyst described in Example 1 are suspended in 200 grams of ethyl acetate. The mixture is placed in a steel reaction vessel capable of being heated. The reaction vessel is sealed, attached to a supply of hydrogen,
and heated to 80 C. with good agitation under a hydrogen pressure of 800 lbs/sq. in. After the calculated amount of hydrogen has been absorbed, the reaction vessel is unloaded and'the aminoguanidine isolated as described in Example 1.
The resulting aminoguanidine may be isolated by filtration and neutralizing with dilute sulfuric acid. To the solution, after evaporation, is added potassium bicarbonate to precipitate the aminoguanidine. The solution may then be cooled, filtered, and the product dried.
The statements inserted in the claims in the substantial absence of acids" and in the absence of any substantial amount of acids are used to define the invention yet not limiting it as to the presence of small amounts of acidinadvertently present as impurities in the nitroguanidine. The presence of some acid would be expected, at least in some instances, since the nitroguanidine used is separated from a solution high in sulphuric acid.
I claim:
l. The process of producing an aminoguanidine which comprises the reduction of nitroguanidine with hydrogen at a temperature between 25 C. and 125 C. in the presence of a hydrogenation metal catalyst, and in the absenceof any substantial amount of acids.
2. The process of claim 1, in which the metal catalyst is a nickel catalyst.
3. The process of claim 1, in which the metal catalyst is taken from a group consisting 01' copper, nickel, iron, and cobalt. 5
4. The process of claim 1, in which the catalyst is taken from the eighth group of the periodic table.
5. The process of producing aminoguanidine which comprises the reduction of unsubstituted 10 nitroguanidine with hydrogen at a temperature between 25 C. and 125 C. in the presence of a hydrogenation metal catalyst and in the absence of any substantial amount of acids.
6. The process of producing aminoguanidine 15 which comprises reducing nitroguanidine by means of hydrogen in the presence of a hydrogenation metal catalyst and in the absence of any substantial amount of acids, operating the process at a pressure above 400 pounds per square 20 inch, and maintaining the temperature of the reaction between 25 C. and 125 C.
7 The process of claim 6, in which the pressure is maintained between 400 pounds and 1200 pounds per square inch. 25
8. The process of claim 6, in which the pressure is maintained between 400 pounds and 3000 pounds per square inch.
' 9. The process of producing an aminoguanidine which comprises reducing nitroguanidine by 30 means of hydrogen in the presence of a hydrogenation metal catalyst, and in the absence of any substantial amount of acids, operating the process in the presence of a buffering material and at a pressure above 400 pounds per square inch.
10. The process of claim 9, in which the bufferingmaterial is an alkaline material.
11. The process of claim 9, in which the buffering material is magnesium sulfate. -30
12. The process of claim 9, in which the buffering material is a mixture of phosphates of the alkali metals.
13. The process of claim 9, in which the buffering material is a mixture of borax with boric acid 45,
and sodium chloride.
RUSSELL McGILL;
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US609043A US2033203A (en) | 1932-05-03 | 1932-05-03 | Process of manufacturing aminoguanidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US609043A US2033203A (en) | 1932-05-03 | 1932-05-03 | Process of manufacturing aminoguanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2033203A true US2033203A (en) | 1936-03-10 |
Family
ID=24439131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US609043A Expired - Lifetime US2033203A (en) | 1932-05-03 | 1932-05-03 | Process of manufacturing aminoguanidine |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2033203A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2559085A (en) * | 1948-10-22 | 1951-07-03 | Honorary Advisory Council Sci | Preparation of n-substituted-n'-nitroguanidines |
| US2584784A (en) * | 1949-05-21 | 1952-02-05 | Du Pont | Salts of 1-salicylalaminoguanidine |
-
1932
- 1932-05-03 US US609043A patent/US2033203A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2559085A (en) * | 1948-10-22 | 1951-07-03 | Honorary Advisory Council Sci | Preparation of n-substituted-n'-nitroguanidines |
| US2584784A (en) * | 1949-05-21 | 1952-02-05 | Du Pont | Salts of 1-salicylalaminoguanidine |
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