GB1236955A - Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts thereof - Google Patents
Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts thereofInfo
- Publication number
- GB1236955A GB1236955A GB23137/68A GB2313768A GB1236955A GB 1236955 A GB1236955 A GB 1236955A GB 23137/68 A GB23137/68 A GB 23137/68A GB 2313768 A GB2313768 A GB 2313768A GB 1236955 A GB1236955 A GB 1236955A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- acid
- epoxypropyl
- formula
- ester
- 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 15
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title abstract 7
- -1 1,2-epoxypropyl Chemical group 0.000 abstract 17
- 239000002253 acid Substances 0.000 abstract 11
- 238000006243 chemical reaction Methods 0.000 abstract 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 239000002585 base Substances 0.000 abstract 6
- 239000003795 chemical substances by application Substances 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- 230000007062 hydrolysis Effects 0.000 abstract 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 5
- 239000005864 Sulphur Substances 0.000 abstract 5
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 4
- 125000004185 ester group Chemical group 0.000 abstract 4
- 239000007800 oxidant agent Substances 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract 3
- 230000002378 acidificating effect Effects 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical class OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 3
- 239000011707 mineral Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 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 abstract 2
- 241001465754 Metazoa Species 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 abstract 2
- 238000006073 displacement reaction Methods 0.000 abstract 2
- 238000006735 epoxidation reaction Methods 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000003456 ion exchange resin Substances 0.000 abstract 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- 229910000077 silane Inorganic materials 0.000 abstract 2
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 abstract 2
- 229940071536 silver acetate Drugs 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- 125000006724 (C1-C5) alkyl ester group Chemical group 0.000 abstract 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 abstract 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 1
- WUEAMTVQNGYLRI-UHFFFAOYSA-N 2-dichlorophosphoryl-1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=C(P(Cl)(Cl)=O)C(C(C)C)=C1 WUEAMTVQNGYLRI-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 102000013563 Acid Phosphatase Human genes 0.000 abstract 1
- 108010051457 Acid Phosphatase Proteins 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 102000013392 Carboxylesterase Human genes 0.000 abstract 1
- 108010051152 Carboxylesterase Proteins 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007945 N-acyl ureas Chemical class 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- BSKZDJXVMPWPRA-UHFFFAOYSA-N O.[Br] Chemical compound O.[Br] BSKZDJXVMPWPRA-UHFFFAOYSA-N 0.000 abstract 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
- 102000004203 Phosphoric Triester Hydrolases Human genes 0.000 abstract 1
- 108090000754 Phosphoric Triester Hydrolases Proteins 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 241000256250 Spodoptera littoralis Species 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000006159 dianhydride group Chemical group 0.000 abstract 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- BTJRKNUKPQBLAL-UHFFFAOYSA-N hydron;4-methylmorpholine;chloride Chemical compound Cl.CN1CCOCC1 BTJRKNUKPQBLAL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000009884 interesterification Methods 0.000 abstract 1
- 229960004873 levomenthol Drugs 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 abstract 1
- 150000003008 phosphonic acid esters Chemical class 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 150000003140 primary amides Chemical class 0.000 abstract 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 150000007970 thio esters Chemical class 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- 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
-
- 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
-
- 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02J—CIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
- H02J3/00—Circuit arrangements for ac mains or ac distribution networks
- H02J3/38—Arrangements for parallely feeding a single network by two or more generators, converters or transformers
- H02J3/381—Dispersed generators
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02J—CIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
- H02J2300/00—Systems for supplying or distributing electric power characterised by decentralized, dispersed, or local generation
- H02J2300/20—The dispersed energy generation being of renewable origin
- H02J2300/28—The renewable source being wind energy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Power Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23137/68A GB1236955A (en) | 1968-05-15 | 1968-05-15 | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts thereof |
| NL6814982A NL6814982A (de) | 1968-05-15 | 1968-10-18 | |
| IL6830914A IL30914A0 (en) | 1968-05-15 | 1968-10-21 | Processes for the preparation of phosphonic acids and salts thereof |
| BR203535/68A BR6803535D0 (pt) | 1968-05-15 | 1968-10-29 | Processo para a producao de antibioticos |
| LU57190D LU57190A1 (de) | 1968-05-15 | 1968-10-29 | |
| ZM141/68A ZM14168A1 (en) | 1968-05-15 | 1968-10-30 | Process for production of antibiotics |
| OA53406A OA02916A (fr) | 1968-05-15 | 1968-10-30 | Procédé de fabrication d'antibiotiques plus particulièrement l'acide (cis-1,2-époxypropyl) phosphonique et de ses sels. |
| MT588A MTP588B (en) | 1968-05-15 | 1968-11-22 | Chemical process (process for production of intibiotics |
| IE59769A IE32881B1 (en) | 1968-05-15 | 1969-04-29 | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts thereof |
| IL32112A IL32112A0 (en) | 1968-05-15 | 1969-04-30 | Methods for making phosphonates |
| BE732673D BE732673A (de) | 1968-05-15 | 1969-05-07 | |
| DE19691923544 DE1923544A1 (de) | 1968-05-15 | 1969-05-08 | Verfahren zum Herstellen von Phosphonaten |
| CH743169A CH554378A (de) | 1968-05-15 | 1969-05-14 | Verfahren zur herstellung von (cis-1,2-epoxypropyl)phosphonsaeure bzw.- phosphonsaeure sowie deren salze. |
| BR208793/69A BR6908793D0 (pt) | 1968-05-15 | 1969-05-14 | Processo para a producao de fosfanatos |
| NL6907461A NL6907461A (de) | 1968-05-15 | 1969-05-14 | |
| AT463869A AT309464B (de) | 1968-05-15 | 1969-05-14 | Verfahren zur Herstellung der neuen (cis-1,2-Epoxypropyl)-phosphosäure oder eines Salzes dieser Säure |
| ES367268A ES367268A1 (es) | 1968-05-15 | 1969-05-14 | Un procedimiento para la obtencion de acidos fosfonicos o sus sales. |
| HUME1078A HU163585B (de) | 1968-05-15 | 1969-05-15 | |
| FR6915926A FR2011837A1 (de) | 1968-05-15 | 1969-05-16 | |
| ES395160A ES395160A1 (es) | 1968-05-15 | 1971-09-16 | Un procedimiento para la obtencion de acidos fosfonicos o sus sales. |
| ES71395159A ES395159A1 (es) | 1968-05-15 | 1971-09-16 | Un procedimiento para la obtencion de acidos fosfonicos o sus sales. |
| ES395154A ES395154A1 (es) | 1968-05-15 | 1971-09-16 | Un procedimiento para la obtencion de acidos fosfonicos o sus sales. |
| ES395156A ES395156A1 (es) | 1968-05-15 | 1971-09-16 | Un procedimiento para la obtencion de acidos fosfonicos o sus sales. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23137/68A GB1236955A (en) | 1968-05-15 | 1968-05-15 | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1236955A true GB1236955A (en) | 1971-06-23 |
Family
ID=10190752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23137/68A Expired GB1236955A (en) | 1968-05-15 | 1968-05-15 | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and salts thereof |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT309464B (de) |
| BE (1) | BE732673A (de) |
| BR (2) | BR6803535D0 (de) |
| CH (1) | CH554378A (de) |
| DE (1) | DE1923544A1 (de) |
| ES (5) | ES367268A1 (de) |
| FR (1) | FR2011837A1 (de) |
| GB (1) | GB1236955A (de) |
| HU (1) | HU163585B (de) |
| IL (2) | IL30914A0 (de) |
| LU (1) | LU57190A1 (de) |
| MT (1) | MTP588B (de) |
| NL (2) | NL6814982A (de) |
| OA (1) | OA02916A (de) |
| ZM (1) | ZM14168A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117964661A (zh) * | 2024-04-01 | 2024-05-03 | 深圳创元生物医药科技有限公司 | 一种磷霉素基因毒杂质c的制备方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635795A (en) * | 1968-12-27 | 1972-01-18 | Merck & Co Inc | Enzymatic resolution of racemic (cis-1,2-epoxypropyl) phosphonic acid compounds |
| IT1042192B (it) * | 1975-08-29 | 1980-01-30 | Italchemi Spa | Sintesi di acidi epossialchilfo sfonici |
| US20230219817A1 (en) * | 2020-06-16 | 2023-07-13 | Yara International Asa | Process for the removal of heavy metals from a phosphoric acid containing composition |
-
1968
- 1968-05-15 GB GB23137/68A patent/GB1236955A/en not_active Expired
- 1968-10-18 NL NL6814982A patent/NL6814982A/xx unknown
- 1968-10-21 IL IL6830914A patent/IL30914A0/xx unknown
- 1968-10-29 BR BR203535/68A patent/BR6803535D0/pt unknown
- 1968-10-29 LU LU57190D patent/LU57190A1/xx unknown
- 1968-10-30 ZM ZM141/68A patent/ZM14168A1/xx unknown
- 1968-10-30 OA OA53406A patent/OA02916A/xx unknown
- 1968-11-22 MT MT588A patent/MTP588B/xx unknown
-
1969
- 1969-04-30 IL IL32112A patent/IL32112A0/xx unknown
- 1969-05-07 BE BE732673D patent/BE732673A/xx unknown
- 1969-05-08 DE DE19691923544 patent/DE1923544A1/de active Pending
- 1969-05-14 AT AT463869A patent/AT309464B/de not_active IP Right Cessation
- 1969-05-14 BR BR208793/69A patent/BR6908793D0/pt unknown
- 1969-05-14 CH CH743169A patent/CH554378A/de not_active IP Right Cessation
- 1969-05-14 NL NL6907461A patent/NL6907461A/xx unknown
- 1969-05-14 ES ES367268A patent/ES367268A1/es not_active Expired
- 1969-05-15 HU HUME1078A patent/HU163585B/hu unknown
- 1969-05-16 FR FR6915926A patent/FR2011837A1/fr not_active Withdrawn
-
1971
- 1971-09-16 ES ES71395159A patent/ES395159A1/es not_active Expired
- 1971-09-16 ES ES395154A patent/ES395154A1/es not_active Expired
- 1971-09-16 ES ES395160A patent/ES395160A1/es not_active Expired
- 1971-09-16 ES ES395156A patent/ES395156A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117964661A (zh) * | 2024-04-01 | 2024-05-03 | 深圳创元生物医药科技有限公司 | 一种磷霉素基因毒杂质c的制备方法 |
| CN117964661B (zh) * | 2024-04-01 | 2024-06-07 | 深圳创元生物医药科技有限公司 | 一种磷霉素基因毒杂质c的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES367268A1 (es) | 1972-03-16 |
| DE1923544A1 (de) | 1970-08-27 |
| IL32112A0 (en) | 1969-06-25 |
| NL6814982A (de) | 1969-11-18 |
| IL30914A0 (en) | 1968-12-26 |
| BR6803535D0 (pt) | 1973-02-22 |
| ES395154A1 (es) | 1973-12-16 |
| NL6907461A (de) | 1969-11-18 |
| AT309464B (de) | 1973-08-27 |
| ES395159A1 (es) | 1974-01-01 |
| FR2011837A1 (de) | 1970-03-13 |
| ES395156A1 (es) | 1974-01-01 |
| ES395160A1 (es) | 1974-01-01 |
| HU163585B (de) | 1973-09-27 |
| ZM14168A1 (en) | 1970-06-18 |
| LU57190A1 (de) | 1969-05-16 |
| BR6908793D0 (pt) | 1973-05-10 |
| CH554378A (de) | 1974-09-30 |
| OA02916A (fr) | 1970-12-15 |
| MTP588B (en) | 1970-10-23 |
| BE732673A (de) | 1969-11-07 |
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