US1669542A - Manufacture of basic bismuth salts of aryl-arsinic acids - Google Patents
Manufacture of basic bismuth salts of aryl-arsinic acids Download PDFInfo
- Publication number
- US1669542A US1669542A US152307A US15230726A US1669542A US 1669542 A US1669542 A US 1669542A US 152307 A US152307 A US 152307A US 15230726 A US15230726 A US 15230726A US 1669542 A US1669542 A US 1669542A
- Authority
- US
- United States
- Prior art keywords
- salt
- aryl
- arsinic
- solution
- manufacture
- 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
- 150000001621 bismuth Chemical class 0.000 title description 36
- 239000002253 acid Substances 0.000 title description 24
- 238000004519 manufacturing process Methods 0.000 title description 23
- 150000007513 acids Chemical class 0.000 title description 17
- 239000000243 solution Substances 0.000 description 39
- 150000003839 salts Chemical class 0.000 description 33
- 230000001376 precipitating effect Effects 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YPQBHUDKOKUINZ-OLXYHTOASA-L bismuth;sodium;(2r,3r)-2,3-dioxidobutanedioate Chemical compound [Na+].[Bi+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O YPQBHUDKOKUINZ-OLXYHTOASA-L 0.000 description 6
- 229940095064 tartrate Drugs 0.000 description 6
- 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 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052797 bismuth Inorganic materials 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- 150000007519 polyprotic acids Polymers 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical compound O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 101150118507 WASL gene Proteins 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- RBWHSJWBPWWFKV-UHFFFAOYSA-L bismuth;potassium;sodium;2,3-dihydroxybutanedioate Chemical compound [Na+].[K+].[Bi+3].[O-]C(=O)C(O)C(O)C([O-])=O RBWHSJWBPWWFKV-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- SULICOHAQXOMED-YDXPQRMKSA-H dibismuth;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Bi+3].[Bi+3].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O SULICOHAQXOMED-YDXPQRMKSA-H 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- -1 or sodiumpotassium- Chemical compound 0.000 description 1
- YKQNYRADBBHWOK-UHFFFAOYSA-N phenylarsonamidic acid Chemical compound N[As](O)(=O)C1=CC=CC=C1 YKQNYRADBBHWOK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Definitions
- the present invention is for the manufacture of basic bismuth salts of aryl-arsinic acids, and has particular reference to the manufacture of the bismuth salt of N- phenyl-glycinamide-p-arsinic acid.
- the basic bismuth salts of aryl-arsinic acids possess therapeutic properties, and, appropriately prepared, are suitable for injection; and it has been found that in such salts the therapeutic properties of both bismuth and arsenic are advantageously combined, the toxicity of the products being generally of a low order.
- the method has a number of disadvantages. If solutions of equimolecular' proportions of the aforesaid type of reagents be mixed together at ordinary temperature, precipitation of the new compound is slow and incomplete, and the yield poor. With application of heat, precipitation is expedited, but without the production of a satisfactory yield. If the attempt be made to correct incomplete precipitation by leavingthe reaction mixture to stand, the precipitate frequently appears in the form of a gel, which is difficult to wash, and even in these circumstances, an' unsatisfactory yield of the new salt is obtained.
- the process of the present invention consists in an adaptation of the aforesaid process to the manufacture of basic bismuth salts of the type described, whereby the salts are obtained in substantial yield, and in a form readily adaptable to purification and to the preparation of therapeutic solutions.
- the manufacture of basic bismuth salts of arylarsinic acids is characterized by precipitating the solution of a bismuth salt with the solution of a salt of an aryl-arsinic acid un der application of heat in presence of a con siderable excess of the aryl-arsinic acid salt.
- the preferred type of bismuth salts with which to effect precipitation are salts of hydroxy-polybasic acids, of which tartaric acid is an example, such salts being conveniently employed in the form ofthe soluble double salts with such acids of bismuth and alkaline bases, as, for example, sodium-, or sodiumpotassium-, bismuth tartrate.
- the solution of a soluble bismuthyl salt of a hydroxy-polybasic acid such as tartaric acid
- a soluble bismuthyl salt of an aryl-arsinic acid may be added to the solution containing a substantial excess over the molecular equivalent of a soluble salt of an aryl-arsinic acid.
- an aqueous solution of an alkali bismuthyl tartrate such as sodium bismuthyl tartrate
- an aqueous solution of the sodium derivative of the aryl-arsinic acid in considerable excess over the quantity theoretically equivalent to the bismuthyl salt.
- the precipitated bismuth oxy-saltof the arsinie acid is washed and dried, preferably at a low temperature. It is advisable in most cases to separate the precipitate from the reaction liquor without undue delay in order to avoid undesirable change in condition of the product.
- the excess should not be below about 25 per cent, and may be as high as 80 per cent.
- the PHI' As in the case of the temperature factor, the PHI'.
- the reacting substances may be mixed together at the ordinary temperature, and the temperature then appropriately raisedand maintained as may be necessary to promote the reaction and the separation of a fine washable precipitate. If the temperature be too low, the precipitate tends to assume the form of avgel, while if the temperature at least 30 C.
- the precipitate may separate in too line a condition for satisfactory handlingf
- a temperature of 100 C. produces a precipitate so finely sub-divided as tomake Washing diflicult and protracted.
- the generally )referred temperature is one about C.
- Tendency to gel formation is generally observable up to a temperature of As Will be appreciated, a definite rule to meet all cases cannot be laid down as to'the degree of excess and the temperature; but the necessary adjustn'ient of these factors is attainable when it is borne in mind that the object in View is to produce a fine precipitate, which is yet sul'liciently. susceptible with reasonable facility to purification by Wash-- ing; and the limits given in illustration of the variation which may be made in the factors in question are those which have been found to be generally applicable with satis-. factory results.
- the precipitate should be separated Without delay, for a greater or less tendency to gel formation is displayed according to the length of time the reactionmixture is allowed to stand.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1669542X | 1925-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1669542A true US1669542A (en) | 1928-05-15 |
Family
ID=10888031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US152307A Expired - Lifetime US1669542A (en) | 1925-12-05 | 1926-12-02 | Manufacture of basic bismuth salts of aryl-arsinic acids |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US1669542A (enrdf_load_stackoverflow) |
| BE (1) | BE338406A (enrdf_load_stackoverflow) |
| FR (1) | FR632834A (enrdf_load_stackoverflow) |
-
0
- FR FR632834D patent/FR632834A/fr not_active Expired
- BE BE338406D patent/BE338406A/xx unknown
-
1926
- 1926-12-02 US US152307A patent/US1669542A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE338406A (enrdf_load_stackoverflow) | 1900-01-01 |
| FR632834A (enrdf_load_stackoverflow) | 1928-01-16 |
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