ES367112A1 - A PROCEDURE FOR THE PREPARATION OF A 1-PROPINYLPHOSPHONIC ACID SALT. - Google Patents
A PROCEDURE FOR THE PREPARATION OF A 1-PROPINYLPHOSPHONIC ACID SALT.Info
- Publication number
- ES367112A1 ES367112A1 ES367112A ES367112A ES367112A1 ES 367112 A1 ES367112 A1 ES 367112A1 ES 367112 A ES367112 A ES 367112A ES 367112 A ES367112 A ES 367112A ES 367112 A1 ES367112 A1 ES 367112A1
- Authority
- ES
- Spain
- Prior art keywords
- phosphonic acid
- cis
- salt
- base
- epoxypropyl
- 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
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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3826—Acyclic unsaturated acids
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A salt of 1-propynyl phosphonic acid is prepared by treating a mono- or diester of the formula or mixture thereof with a base, R being a straight or branched chain alkenyl or alkynyl group having 2 to 7 carbon atoms or a substituted or unsubstituted monocyclic aryl group and R1 is hydrogen or is a group as defined for R. Preferably R and R1 are 2-propynyl groups. The treatment is usually effected by contacting the ester in a solvent with the base for sufficient time to cleave the ester. The base used may be a strong inorganic or organic base, e.g. an alkali or alkaline earth metal oxide or hydroxide, a basic quaternary ammonium type anion exchange resin, triethylamine, trimethylamine, triethanolamine, an N-alkylpiperidine or tetramethyl ammonium hydroxide. The salts may be converted to the free 1-propynyl phosphonic acid by treating with a mineral acid, e.g. HCl or H 2 SO 4 . Suitable solvents for the main reaction include water, alcohols, dimethylsulphoxide, N,N1-dimethyl formamide and sulpholane or an excess of the base (when appropriate) may be used as solvent. The sodium salt of 1-propynyl phosphonic acid may be converted to the sodium salt of cispropenyl phosphonic acid by hydrogenation and the cis-propenylp hosphonicac id may be oxidized with H 2 O 2 to form racemic cis-1,2-epoxypropyl phosphonic acid which may be recovered as the sodium salt and the latter treated with quinine in methanol to yield the quinine salt of (-) (cis- 1,2-epoxypropyl) phosphonic acid which is then converted to the ammonium salt by treating with NH 4 OH in water, details being given for each step of the process. The (-) (cis- 1,2-epoxypropyl) phosphonic acid is an antimicrobial agent and may be administered orally e.g. in the form of its Na, K or Ca salt, or parenterally. Also, salts of (+) (cis-1,2-epoxypropyl) phosphonic acid inhibit undesirable bacterial growth in the white water used in paper mills, or in paints e.g. polyvinyl acetate latex paint.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72945468A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES367112A1 true ES367112A1 (en) | 1971-04-01 |
Family
ID=24931106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES367112A Expired ES367112A1 (en) | 1968-05-15 | 1969-05-12 | A PROCEDURE FOR THE PREPARATION OF A 1-PROPINYLPHOSPHONIC ACID SALT. |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT297022B (en) |
| BE (1) | BE733054A (en) |
| CH (1) | CH515280A (en) |
| DE (1) | DE1924148A1 (en) |
| ES (1) | ES367112A1 (en) |
| GB (1) | GB1221738A (en) |
| IL (1) | IL32134A0 (en) |
| NL (1) | NL6904672A (en) |
-
1969
- 1969-03-26 NL NL6904672A patent/NL6904672A/xx unknown
- 1969-05-01 IL IL32134A patent/IL32134A0/en unknown
- 1969-05-08 CH CH709369A patent/CH515280A/en not_active IP Right Cessation
- 1969-05-09 AT AT448769A patent/AT297022B/en not_active IP Right Cessation
- 1969-05-12 DE DE19691924148 patent/DE1924148A1/en active Pending
- 1969-05-12 GB GB23964/69A patent/GB1221738A/en not_active Expired
- 1969-05-12 ES ES367112A patent/ES367112A1/en not_active Expired
- 1969-05-14 BE BE733054D patent/BE733054A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1221738A (en) | 1971-02-10 |
| IL32134A0 (en) | 1969-07-30 |
| NL6904672A (en) | 1969-11-18 |
| CH515280A (en) | 1971-11-15 |
| DE1924148A1 (en) | 1970-04-16 |
| BE733054A (en) | 1969-11-11 |
| AT297022B (en) | 1972-03-10 |
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