ES367101A1 - Procedure for the preparation of acid () (1,2-expoxipropil) phosphonic and steres and salts of the same. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the preparation of acid () (1,2-expoxipropil) phosphonic and steres and salts of the same. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES367101A1 ES367101A1 ES367101A ES367101A ES367101A1 ES 367101 A1 ES367101 A1 ES 367101A1 ES 367101 A ES367101 A ES 367101A ES 367101 A ES367101 A ES 367101A ES 367101 A1 ES367101 A1 ES 367101A1
- Authority
- ES
- Spain
- Prior art keywords
- salt
- ester
- phosphonic acid
- salts
- mono
- 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
- 150000003839 salts Chemical class 0.000 title abstract 10
- 238000000034 method Methods 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 2
- -1 1,2-epoxypropyl Chemical group 0.000 abstract 8
- 239000003054 catalyst Substances 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 6
- 238000005984 hydrogenation reaction Methods 0.000 abstract 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 3
- 229910052751 metal Inorganic materials 0.000 abstract 3
- 239000002184 metal Substances 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- CQPJLZWBXXBTJA-UHFFFAOYSA-N prop-1-ynylphosphonic acid Chemical compound CC#CP(O)(O)=O CQPJLZWBXXBTJA-UHFFFAOYSA-N 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 abstract 2
- 238000006735 epoxidation reaction Methods 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- PNSGKNMSCJKTJV-UHFFFAOYSA-N CC1=C(OP(O)=O)O1 Chemical compound CC1=C(OP(O)=O)O1 PNSGKNMSCJKTJV-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- YMDXZJFXQJVXBF-STHAYSLISA-N fosfomycin Chemical compound C[C@@H]1O[C@@H]1P(O)(O)=O YMDXZJFXQJVXBF-STHAYSLISA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910000765 intermetallic Inorganic materials 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 abstract 1
- 235000015497 potassium bicarbonate Nutrition 0.000 abstract 1
- 239000011736 potassium bicarbonate Substances 0.000 abstract 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 abstract 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 abstract 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical class O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 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
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
(Cis 1,2-epoxypropyl) phosphonic acid or an ester or salt thereof is obtained by treating an ester or salt of 1-propynyl phosphonic acid with an epoxidizing agent and hydrogenating the reaction product in situ in the presence of a hydrogenation catalyst comprising a metal or a metallic compound. In an alternative method the reduction of the epoxidized product is carried out by means of di-imide (NH=NH) formed in situ, e.g. by oxidation of hydrazine with H 2 O 2 in the presence of copper sulphate. Suitable ester starting materials include mono- and di - (C 1 -C 8 alkyl), mono- and di (C 2 -C 8 alkenyl), mono- and di- (C 2 -C 8 alkynyl), mono - and di - (C 3 -C 8 cycloalkyl) esters and mono - and di - aryl, aralkyl or alkaryl esters of 1-propynyl phosphonic acid and suitable salts include alkaline earth metal salts, mono- and dialkali metal salts and ammonium or organic amine salts. The epoxidizing agent may be a perorganic acid or may be hydrogen peroxide in the presence of a neutral tungstic acid salt catalyst. Typical hydrogenation catalysts are copper, nickel, palladium and platinum catalysts and Raney metal catalysts e.g. Raneynickel, -cobalt, -iron and -copper catalysts. The epoxidation is generally carried out in a solvent and the resulting 1,2-epoxypropenyl phosphonic acid ester or salt is subjected directly to the hydrogenation treatment without isolation, the hydrogenation being effected, after addition of the hydrogenation catalyst, until saturation of the olefinic bond is complete. When the ester starting material is an aralkyl, alkenyl or alkynyl ester the ester group is removed during the hydrogenation and the resulting cis 1,2- epoxypropyl phosphonic acid may be isolated from the reaction medium in the form of a salt. When the products are esters they may be converted to the free phosphonic acid or salt thereof by a variety of methods according to the nature of the ester group, e.g. by U.V. irradiation, basic hydrolysis, acid hydrolysis, enzymolysis, treatment with ionic salts, reduction, or ester interchange followed by one of the above methods. Any 1,1,2,2-diepoxy propyl phosphonic acid ester or salt which might be formed in the epoxidation reaction mixture may be converted to the corresponding (1,2-epoxypropenyl) phosphonate by adding triphenyl phosphine to the reaction mixture and heating at about 150 to 170 C. for 20 to 60 minutes. The triphenyl phosphine oxide formed is then removed by filtration, and the mixture then catalytically hydrogenated to form the desired product. The ( ) (Cis, 1,2-epoxypropyl) phosphonic acid and its salts have antibiotic properties. 1 - Propynyl phosphonic acid is obtained by refluxing dibenzyl 1-propynyl phosphonate with conc. HCl and is converted to its monosodium salt by addition of aqueous sodium bicarbonate solution to a pH of 5À5 to 6 or to the di-salt by addition of further base to pH 8 to 9. Other specified bases which may be used to form salts are potassium bicarbonate, CaCO 3 , MgCO 3 , NH 4 OH and benzylamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72940568A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES367101A1 true ES367101A1 (en) | 1971-04-01 |
Family
ID=24930886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES367101A Expired ES367101A1 (en) | 1968-05-15 | 1968-05-12 | Procedure for the preparation of acid () (1,2-expoxipropil) phosphonic and steres and salts of the same. (Machine-translation by Google Translate, not legally binding) |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT292018B (en) |
| BE (1) | BE733042A (en) |
| DE (1) | DE1924149A1 (en) |
| ES (1) | ES367101A1 (en) |
| GB (1) | GB1238422A (en) |
| IL (1) | IL32122A0 (en) |
| NL (1) | NL6904505A (en) |
-
1968
- 1968-05-12 ES ES367101A patent/ES367101A1/en not_active Expired
-
1969
- 1969-03-24 NL NL6904505A patent/NL6904505A/xx unknown
- 1969-05-01 IL IL32122A patent/IL32122A0/en unknown
- 1969-05-08 AT AT441969A patent/AT292018B/en not_active IP Right Cessation
- 1969-05-12 DE DE19691924149 patent/DE1924149A1/en active Pending
- 1969-05-12 GB GB1238422D patent/GB1238422A/en not_active Expired
- 1969-05-14 BE BE733042D patent/BE733042A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1924149A1 (en) | 1970-01-15 |
| GB1238422A (en) | 1971-07-07 |
| NL6904505A (en) | 1969-11-18 |
| AT292018B (en) | 1971-08-10 |
| BE733042A (en) | 1969-11-14 |
| IL32122A0 (en) | 1969-07-30 |
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