SE446739B - SET TO MAKE SALTS OF (-) CIS-1,2-EPOXYPROPYLPHOSPHONIC ACID - Google Patents
SET TO MAKE SALTS OF (-) CIS-1,2-EPOXYPROPYLPHOSPHONIC ACIDInfo
- Publication number
- SE446739B SE446739B SE7905874A SE7905874A SE446739B SE 446739 B SE446739 B SE 446739B SE 7905874 A SE7905874 A SE 7905874A SE 7905874 A SE7905874 A SE 7905874A SE 446739 B SE446739 B SE 446739B
- Authority
- SE
- Sweden
- Prior art keywords
- cis
- acid
- epoxypropylphosphonic
- solution
- salt
- Prior art date
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- -1 hydrogen epoxide Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 1
- 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 1
- QHFQAJHNDKBRBO-UHFFFAOYSA-L calcium chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ca+2] QHFQAJHNDKBRBO-UHFFFAOYSA-L 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- C07F9/02—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Description
15' 20 25 30 '35 e44e 139 2 t en nästan fullständig återvinning av det använda Thiomi- caminet (mer än 93%). 15 '20 25 30' 35 e44e 139 2 t an almost complete recovery of the Thiomicamine used (more than 93%).
Enligt sättet för föreliggande uppfinning vars kän- .netecken framgår av patentkravet oxideras cis-l-prope- nylfosfonsyran (II) till den racemiska epoxisyran (I) med användning av vätepefoxid och i närvaro av natrium- I volframatdihydrat. Efter att fullständigt ha sönderdelat den väteperoxid som fortfarande förefinnes i reaktions- .blandningen tillsätts lhiomicamine. Den erhållna suspen- sionen alkaliniseras med natriumhydroxid för att ge lös- ningen av natriumsaltet av (-)cis-l,2-epoxipropylfosfon- syra, som omvandlas till saltet av den önskade basen ge- nom.lämplig behandling. Oxidationen av cis-l-propenylfos~ fonsyran till den motsvarande racemiska epoxisyran genom- föres medelst känd teknik med användning av väteperoxid som oxidationsmedel och i närvaro av natriumvolframatdi- hydrat¿ Efter avslutning av oxidationsreaktionen är det nödvändigt att sönderdela den väteperoxid som fortfa- rande förefinnes i reaktionslösningen innan Thiomicamine tillsätts, för att förhindra oxidation därav. Sedan oxi- dationen avslutats behandlas reaktionslösningen med hydrazinhydrat och en katalytisk mängd av reducerad kop- par vid en temperatur mellan 45°C och 50°C, varvid väte- peroxid snabbt sönderdelas. Tillsättningen av Thiomica- mine till reaktionslösningen, som innehåller den race- miska epoxisyran (I), genomföres gradvis genom att hålla pH-värdet vid 5-6 genom surgöring.According to the process of the present invention, the characteristics of which are claimed in the claim, the cis-1-propenylphosphonic acid (II) is oxidized to the racemic epoxy acid (I) using hydrogen epoxide and in the presence of sodium I tungstate dihydrate. After completely decomposing the hydrogen peroxide still present in the reaction mixture, lhiomicamine is added. The resulting suspension is alkalinized with sodium hydroxide to give the solution of the sodium salt of (-) cis-1,2-epoxypropylphosphonic acid, which is converted to the salt of the desired base by appropriate treatment. The oxidation of the cis-1-propenylphosphonic acid to the corresponding racemic epoxy acid is carried out by known techniques using hydrogen peroxide as the oxidizing agent and in the presence of sodium tungstate dihydrate. in the reaction solution before adding Thiomicamine, to prevent oxidation thereof. After the oxidation is completed, the reaction solution is treated with hydrazine hydrate and a catalytic amount of reduced copper at a temperature between 45 ° C and 50 ° C, whereby hydrogen peroxide decomposes rapidly. The addition of Thiomicamine to the reaction solution, which contains the racemic epoxy acid (I), is carried out gradually by maintaining the pH at 5-6 by acidification.
Följande utföringsexempel ges för att belysa sättet enligt uppfinningen. Exemplen är avsedda att belysa upp- finningen och inte att begränsa densamma.The following working examples are given to illustrate the method according to the invention. The examples are intended to illustrate the invention and not to limit it.
EXEMPEL l Framställning av kalciumsaltet av (-)cis-l,2-epoxipropyl- fosfonsyramonohvdrat. ' .l e _ 600 g (4,91 moler) cis-l-propenylfosfonsyra löstes i 3500 ml vatten och den sålunda erhållna lösningen justerades till pH 5,9 med 30_% natriumhydroxid. En lös- ning, som innehöll 11,2 g natriumvolframatdihydrat, 4,8 g dinatriumedetat och 53 ml vatten, sattes till den Mfl* 10 15 20 25 .3O 35 446 739 3 ovan beredda lösningen under omröring,varvidnwu1arbetade vid rumstemperatur.EXAMPLE 1 Preparation of the calcium salt of (-) cis-1,2-epoxypropylphosphonic acid monohydrate. 600 g (4.91 moles) of cis-1-propenylphosphonic acid were dissolved in 3500 ml of water and the solution thus obtained was adjusted to pH 5.9 with 30% sodium hydroxide. A solution containing 11.2 g of sodium tungstate dihydrate, 4.8 g of disodium edetate and 53 ml of water was added to the above-prepared solution with stirring, stirring at room temperature.
Den erhållna lösningen upphettades till 45-50°C och 620 g (7,3 moler) 40 % väteperoxid tillsattes lång- samt under omröring. Sedan tillsättningen avslutats fick lösningen stå under dessa betingelser i 1,5 h. _3,2 g (0,064 mol) hydrazinhydrat och 0,32 g redu- cerat koppar hälldes därefter i lösningen..The resulting solution was heated to 45-50 ° C and 620 g (7.3 moles) of 40% hydrogen peroxide was added slowly with stirring. After the addition was complete, the solution was allowed to stand under these conditions for 1.5 hours. 3.2 g (0.064 mol) of hydrazine hydrate and 0.32 g of reduced copper were then poured into the solution.
Lösningen, som var fri från oxidationsmedlet, kyl- des till 20°C, avfärgades, avfiltrerades och behandlades med 1045 g (4,9l moler) L(+)-treo-l-(p-metylmerkapto- fenyl)-2-amino-1,3-propandiol (Thiomicamine) och kon- centrerad väteklorid vid rumstemperatur och under om- röring. Thiomicamine tillsattes gradvis och omväxlande med tillsatts av väteklorid för att hålla blandningens pH-värde mellan 5 och 6. Vid slutet av tillsatsen var pH-värdet5,8.The oxidant-free solution was cooled to 20 ° C, decolorized, filtered and treated with 1045 g (4.91 moles) of L (+) - threo-1- (p-methylmercaptophenyl) -2-amino -1,3-propanediol (Thiomicamine) and concentrated hydrogen chloride at room temperature and while stirring. Thiomicamine was added gradually and alternately with the addition of hydrogen chloride to keep the pH of the mixture between 5 and 6. At the end of the addition, the pH was 5.8.
Det hela omrördes under l h vid rumstemperatur, kyldes till 0°C och efter 2 h avfiltrerades den bildade fällningen och tvättades med vatten. Från modervätskorna återvanns 265 g Thiomicamine genom alkalinisering.The whole was stirred for 1 hour at room temperature, cooled to 0 ° C and after 2 hours the precipitate formed was filtered off and washed with water. 265 g of Thiomicamine were recovered from the mother liquors by alkalinization.
»Fällningen, som erhållits såsom beskrivits ovan och som bestod av Thiomicamine-saltet av f-)cis-l,2-epoxipropyl- fosfonsyra, kristalliserades från isopropylalkohol och suspenderades i 2700 ml vatten. Blandningen omrördes vid rumstemperatur och alkaliniserades med lO % natrium- hydroxid. Efter l h under omröring avfiltrerades det Thiomicamine som fortfarande förelåg. Det torkade Thiomi- caminet vägde 570 g.The precipitate obtained as described above, consisting of the thiomicamine salt of f-) cis-1,2-epoxypropylphosphonic acid, was crystallized from isopropyl alcohol and suspended in 2700 ml of water. The mixture was stirred at room temperature and alkalized with 10% sodium hydroxide. After 1 hour with stirring, the thiomicamine still present was filtered off. The dried Thiomicamine weighed 570 g.
Från-vattenlösningen, som innehöll natriumsaltet av (-)cis-l,2-epoxipropylfosfonsyra, utfälldes genom behandling med 760 g (3,47 moler) av enlösning av kalcium- kloridhexahydrat i 760 ml vatten kalciumsaltet av (-)cis-1,2-epoxipropylfosfonsyramonohydrat, som sedan avfiltrerades, tvättades med vatten och torkades. 250 g produkt erhölls. [afi°=-æ°(m3%15m': lalšgs = -1s° (0,3 2 ago) 10 15 g44e7s9 4.The aqueous solution, which contained the sodium salt of (-) cis-1,2-epoxypropylphosphonic acid, was precipitated by treatment with 760 g (3.47 moles) of a solution of calcium chloride hexahydrate in 760 ml of water, the calcium salt of (-) cis-1, 2-Epoxypropylphosphonic acid monohydrate, which was then filtered off, washed with water and dried. 250 g of product were obtained. [a fi ° = - æ ° (m3% 15m ': lalšgs = -1s ° (0,3 2 ago) 10 15 g44e7s9 4.
Genom att avdestillera isopropylalšoholen i iso- propanolmodervätskorna, som erhölls genom att kristal- lisera Thiomicamine-saltet av (-)cis-l,2-epoxipropyl- fosfonsyra, återvanns 141 g Thiomicamine genom alkali- nisering. ;xEMPEL 2 Framställning av dinatriumsalt av (-)cis-l,2-epoxipropyl- Éosfonsxra _ I n Man förfor i enligt med exempel l till dess att vattenlösningen, som innehöll natriumsaltet av (-)cis- _-1,2-epoxipropylfosfonšyra erhöllsq Löšningens_pH-värde justerades till 8,8 genom tillsats av ättiksyra, varpå förångning under vakuum företogs för erhållande av en sirap, från vilken man erhöll dinatriumsaltet av (-)cis- -1,2-epokipropylfosfonsyra genom behandling med etylalko- hol. Produkten vägde 285 g_ I ' ' 20 _ _ o - -_ 20 _ _..o -V [a]D - 5 - (5 % H20) , [a]365 - 17 (5 % H20).By distilling off the isopropyl alcohol in the isopropanol mother liquors obtained by crystallizing the thiomicamine salt of (-) cis-1,2-epoxypropylphosphonic acid, 141 g of thiomicamine were recovered by alkalization. EXAMPLE 2 Preparation of disodium salt of (-) cis-1,2-epoxypropyl-Ephosphonic acid The procedure was carried out according to Example 1 until the aqueous solution containing the sodium salt of (-) cis-1,2-epoxypropylphosphonic acid The pH value of the solution was adjusted to 8.8 by the addition of acetic acid, then evaporation in vacuo to give a syrup from which the disodium salt of (-) cis--1,2-epocipropylphosphonic acid was obtained by treatment with ethyl alcohol. The product weighed 285 g.
»Kf»Kf
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25389/78A IT1097477B (en) | 1978-07-06 | 1978-07-06 | METHOD FOR THE PREPARATION OF SALTS OF (-) CIS-1,2-EPOXYPROPYLPHOSPHONIC ACID |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7905874L SE7905874L (en) | 1980-01-07 |
| SE446739B true SE446739B (en) | 1986-10-06 |
Family
ID=11216556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7905874A SE446739B (en) | 1978-07-06 | 1979-07-05 | SET TO MAKE SALTS OF (-) CIS-1,2-EPOXYPROPYLPHOSPHONIC ACID |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5511575A (en) |
| AT (1) | AT373264B (en) |
| CA (1) | CA1131648A (en) |
| CH (1) | CH640863A5 (en) |
| DE (1) | DE2925359C3 (en) |
| DK (1) | DK284679A (en) |
| ES (1) | ES482227A1 (en) |
| FR (1) | FR2430424A1 (en) |
| GB (1) | GB2024826B (en) |
| GR (1) | GR69597B (en) |
| IE (1) | IE48590B1 (en) |
| IT (1) | IT1097477B (en) |
| NL (1) | NL7905313A (en) |
| SE (1) | SE446739B (en) |
-
1978
- 1978-07-06 IT IT25389/78A patent/IT1097477B/en active
-
1979
- 1979-06-09 JP JP7185879A patent/JPS5511575A/en active Pending
- 1979-06-12 CH CH549079A patent/CH640863A5/en not_active IP Right Cessation
- 1979-06-22 DE DE2925359A patent/DE2925359C3/en not_active Expired
- 1979-06-22 FR FR7916110A patent/FR2430424A1/en active Granted
- 1979-06-27 GB GB7922413A patent/GB2024826B/en not_active Expired
- 1979-06-28 AT AT0455279A patent/AT373264B/en not_active IP Right Cessation
- 1979-07-03 GR GR59500A patent/GR69597B/el unknown
- 1979-07-05 SE SE7905874A patent/SE446739B/en not_active IP Right Cessation
- 1979-07-05 ES ES482227A patent/ES482227A1/en not_active Expired
- 1979-07-05 DK DK284679A patent/DK284679A/en not_active Application Discontinuation
- 1979-07-06 NL NL7905313A patent/NL7905313A/en not_active Application Discontinuation
- 1979-07-06 CA CA331,340A patent/CA1131648A/en not_active Expired
- 1979-08-08 IE IE1272/79A patent/IE48590B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5511575A (en) | 1980-01-26 |
| NL7905313A (en) | 1980-01-08 |
| CA1131648A (en) | 1982-09-14 |
| FR2430424B1 (en) | 1985-04-12 |
| DE2925359A1 (en) | 1980-01-24 |
| IT7825389A0 (en) | 1978-07-06 |
| GR69597B (en) | 1982-07-05 |
| GB2024826A (en) | 1980-01-16 |
| ATA455279A (en) | 1983-05-15 |
| DE2925359C3 (en) | 1981-08-06 |
| DK284679A (en) | 1980-01-07 |
| IE48590B1 (en) | 1985-03-20 |
| IE791272L (en) | 1980-01-06 |
| SE7905874L (en) | 1980-01-07 |
| CH640863A5 (en) | 1984-01-31 |
| AT373264B (en) | 1984-01-10 |
| GB2024826B (en) | 1982-12-01 |
| IT1097477B (en) | 1985-08-31 |
| FR2430424A1 (en) | 1980-02-01 |
| ES482227A1 (en) | 1980-04-01 |
| DE2925359B2 (en) | 1980-09-04 |
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| Date | Code | Title | Description |
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| NUG | Patent has lapsed |
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