GB318491A - Manufacture of organic arsenic and antimony compounds - Google Patents
Manufacture of organic arsenic and antimony compoundsInfo
- Publication number
- GB318491A GB318491A GB26444/29A GB2644429A GB318491A GB 318491 A GB318491 A GB 318491A GB 26444/29 A GB26444/29 A GB 26444/29A GB 2644429 A GB2644429 A GB 2644429A GB 318491 A GB318491 A GB 318491A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amino
- glycollic
- stibinic
- arsinic
- 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
Links
- 150000001463 antimony compounds Chemical class 0.000 title abstract 3
- 229910052785 arsenic Inorganic materials 0.000 title abstract 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 title abstract 3
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 title abstract 2
- 229940093920 gynecological arsenic compound Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 11
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 9
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 8
- 238000006722 reduction reaction Methods 0.000 abstract 6
- MWZAMPYHMUSARJ-UHFFFAOYSA-M stibinic acid Chemical group O[SbH2]=O MWZAMPYHMUSARJ-UHFFFAOYSA-M 0.000 abstract 6
- GOLCXWYRSKYTSP-UHFFFAOYSA-N Arsenious Acid Chemical compound O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 abstract 4
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical compound O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 3
- -1 aromatic amino-substituted arsenic Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 3
- KRCJWINQZNOCJR-UHFFFAOYSA-N (3-amino-4-hydroxyphenyl)arsinic acid Chemical compound NC1=C(O)C=CC(=C1)[AsH](O)=O KRCJWINQZNOCJR-UHFFFAOYSA-N 0.000 abstract 2
- JRIGVWDKYXCHMG-UHFFFAOYSA-N (5-arsoroso-2-hydroxyphenyl)azanium;chloride Chemical compound Cl.NC1=CC([As]=O)=CC=C1O JRIGVWDKYXCHMG-UHFFFAOYSA-N 0.000 abstract 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 229940000488 arsenic acid Drugs 0.000 abstract 2
- 238000006193 diazotization reaction Methods 0.000 abstract 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229950008475 oxophenarsine Drugs 0.000 abstract 2
- CBMUTWVWANYBAM-UHFFFAOYSA-N (5-amino-2-methylphenyl)arsinic acid Chemical compound CC1=C(C=C(C=C1)N)[AsH](O)=O CBMUTWVWANYBAM-UHFFFAOYSA-N 0.000 abstract 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- QDIRPKMUFLNREG-UHFFFAOYSA-N C(C(O)C)(=O)NC=1C=C(C=CC=1O)[AsH](O)=O Chemical compound C(C(O)C)(=O)NC=1C=C(C=CC=1O)[AsH](O)=O QDIRPKMUFLNREG-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- OLKLRWGOTQJBQN-UHFFFAOYSA-M NC=1C=C(C=CC1)[SbH](O)=O Chemical compound NC=1C=C(C=CC1)[SbH](O)=O OLKLRWGOTQJBQN-UHFFFAOYSA-M 0.000 abstract 1
- MMGPTTXANZRJMN-UHFFFAOYSA-N NC=1C=C(C=CC=1Cl)[AsH](O)=O Chemical compound NC=1C=C(C=CC=1Cl)[AsH](O)=O MMGPTTXANZRJMN-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- XKNKHVGWJDPIRJ-UHFFFAOYSA-N arsanilic acid Chemical compound NC1=CC=C([As](O)(O)=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- AWYSLGMLVOSVIS-UHFFFAOYSA-N phenyl(phenylarsanylidene)arsane Chemical compound C1=CC=CC=C1[As]=[As]C1=CC=CC=C1 AWYSLGMLVOSVIS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
318,491. I. G. Farbenindnstrie Akt.- Ges. Sept. 3, 1928, [Convention date]. Organic arsenic and antimony compounds are prepared by (1) introducing an hydroxy-acyl residue into an aromatic amino-substituted arsenic or antimony compound, or (2) introducing an arsenic acid or stibinic acid residue with an hydroxy-acylamino compound of the benzene series, followed if desired by conversion of the product into an arsenoxide or stibinoxide, or into a symmetrical or unsymmetrical arseno- or stibino-benzene, or with an arsenostibincbenzene. According to the examples, (1) 2-methoxy-5- glycollylaminophenylarsinic acid is prepared by introducing arsenic into 2-methoxy-5-nitraniline by Bart's method, reducing the nitro group and heating with glycollic acid; the product may be reduced by known methods into the corresponding arsenoxide and arsenobenzene: (2) m-aminophenylstibinic acid is heated with glycollic acid and the product reduced with sodium hydrosulphite; the resulting stibinobenzene may be converted into the corresponding stibinic acid by oxidation with hydrogen peroxide in ammoniacal solution; (3) p-glycollylaminophenylarsinic acid results when the p-arsanilic acid is heated with glycollic acid; the reduction with sodium hydrosulphite of a mixture of the said arsinic acid with 3-amino-4-hydroxyphenylarsinic acid yields 4- glycollyamino-3<1>-amino-4<1>- hydroxyarsenobenzene; (4) 5-amino-2-glycollyl-anisol, obtained by interaction of 5-nitro-2-amino-anisol with glycollic acid and reduction of the product, is diazotized and treated with antimony trioxide in the presence of glycerine and copper powder; the ammonium salt of the 3-methoxy-4-glycollylaminophenylstibinic acid so obtained is reduced with sodium hydrosulphite in the presence of 3- amino-4-hydroxyphenylarsinic acid and forms 3- amino-4-hydroxy- 3<1> -methoxy- 4<1> -glycollylaminoarsenostibinobenzene. The Specification as open to inspection under Sect. 91 (3) (a) includes also the following examples, (1) p-nitraniline is heated with glycollic acid, the nitro group of the resulting p-glycollylaminonitrobenzene is reduced to the amino group by treatment with hydrogen under pressure in the presence of nickel, and the amino group is then transformed into either the arsinic acid or stibinic acid group by diazotization and treatment with arsenious acid or antimony trioxide, giving p-glycollylaminophenylarsinic or stibinic acid respectively ; (2) marsanilic acid is heated with glycollic acid to form m-glycollylaminophenylarsinic acid; (3) 2-glycollylamino-4-aminophenol, prepared by inter. action of 2-amino-4-nitrophenol with glycollic acid followed by catalytic reduction with hydrogen under pressure, is diazotized and treated with arsenious acid or antimony trioxide, yielding 3- glycollylamino-4-hydroxyphenyl-arsinic acid or - stibinic acid; the arsenic acid can also be prepared by heating 3-amino-4-hydroxyphenyl with glycollic acid; (4) 3-lactylamino-4-hydroxyphenylarsinic acid is obtained from 2-amino-4-nitrophenol by heating with lactic acid, reducing with hydrohulphite to the amino body, and treating the diazotized product with arsenious acid; (5) the amino group of 3-chloro-4-glycollylaminoaniline, prepared by chlorinating p-nitroglycollic acid anilide and catalytically reducing the product, is replaced by the arsinic or stibinic acid group by diazotization and treatment with arsenious acid or antimony trioxide; (6) interaction of 3-amino-4-chlorophenylarsinic acid, 2- methyl-5-aminophenylarsinic acid, or 2-chloro-4- aminophenyl arsinic acid with glycollic acid forms the corresponding glycollylamino compound; (7) p : p<1>-diglycollylaminoarsenobenzene is prepared by hydrosulphite reduction of p-glycollylaminophenylarsinic acid ; similar reduction of 4-glycollylamino-3-methoxyphenylstibinic acid gives 3: 3<1>- methoxy 4: 4<1>-diglycollylaminostibinobenzene; (8) 4 : 3<1> - diglycollylamino - 4<1> - hydroxyarsenobenzene is obtained by reduction with hydrosulphite of p-glycollylaminophenylarsinic acid and 3-glycollylamino-4-hydroxyphenylarsinic acid; (9) 4-hydroxy - 3 - glycollylaminophenylarsenoxide is formed by the reduction of the corresponding arsinic acid with hydriodic and sulphurous acids. In the case of arsinic and stibinic acids, they may be converted into water-soluble salts by treatment with an alkali, ammonia, or an organic base such as ethanolamine, piperidine and diethylamine. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE318491X | 1928-09-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB318491A true GB318491A (en) | 1931-03-12 |
Family
ID=6151046
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26444/29A Expired GB318491A (en) | 1928-09-03 | 1929-08-30 | Manufacture of organic arsenic and antimony compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB318491A (en) |
-
1929
- 1929-08-30 GB GB26444/29A patent/GB318491A/en not_active Expired
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