DD206380A5 - Verfahren zur herstellung von 1-amino-alkan-1,1-diphosphonsaeuren - Google Patents
Verfahren zur herstellung von 1-amino-alkan-1,1-diphosphonsaeuren Download PDFInfo
- Publication number
- DD206380A5 DD206380A5 DD81235680A DD23568081A DD206380A5 DD 206380 A5 DD206380 A5 DD 206380A5 DD 81235680 A DD81235680 A DD 81235680A DD 23568081 A DD23568081 A DD 23568081A DD 206380 A5 DD206380 A5 DD 206380A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- general formula
- item
- water
- onh
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 238000002425 crystallisation Methods 0.000 claims abstract description 3
- 230000008025 crystallization Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 9
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- GPCTYPSWRBUGFH-UHFFFAOYSA-N (1-amino-1-phosphonoethyl)phosphonic acid Chemical compound OP(=O)(O)C(N)(C)P(O)(O)=O GPCTYPSWRBUGFH-UHFFFAOYSA-N 0.000 description 10
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 101000697856 Rattus norvegicus Bile acid-CoA:amino acid N-acyltransferase Proteins 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- RQBBFKINEJYDOB-UHFFFAOYSA-N acetic acid;acetonitrile Chemical compound CC#N.CC(O)=O RQBBFKINEJYDOB-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 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
- C07F9/28—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
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803047107 DE3047107A1 (de) | 1980-12-13 | 1980-12-13 | Verfahren zur hertellung von 1-amino-alkan-1,1-diphosphonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD206380A5 true DD206380A5 (de) | 1984-01-25 |
Family
ID=6119144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81235680A DD206380A5 (de) | 1980-12-13 | 1981-12-11 | Verfahren zur herstellung von 1-amino-alkan-1,1-diphosphonsaeuren |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4418019A (fr) |
| EP (1) | EP0054195B1 (fr) |
| JP (1) | JPS57123197A (fr) |
| CA (1) | CA1169091A (fr) |
| DD (1) | DD206380A5 (fr) |
| DE (2) | DE3047107A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440738A (en) * | 1982-06-10 | 1984-04-03 | Mallinckrodt, Inc. | Stable radiographic imaging agents |
| US4504463A (en) * | 1982-06-10 | 1985-03-12 | Mallinckrodt, Inc. | Process for making a lyophilized product for use in skeletal imaging |
| US4504462A (en) * | 1982-06-10 | 1985-03-12 | Mallinckrodt, Inc. | Process for making a lyophilized product for use in skeletal imaging |
| DE3370156D1 (en) * | 1982-08-25 | 1987-04-16 | Minemet Rech Sa | Process for producing derivatives of hydroxy-methylene diphosphonic acid |
| US5019651A (en) * | 1990-06-20 | 1991-05-28 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
| SE9604414D0 (sv) * | 1996-11-29 | 1996-11-29 | Eka Chemicals Ab | Chemical composition |
| US6907245B2 (en) | 2000-12-04 | 2005-06-14 | Telefonaktiebolaget Lm Ericsson (Publ) | Dynamic offset threshold for diversity handover in telecommunications system |
| EP2225175B1 (fr) * | 2007-12-13 | 2012-12-12 | Akzo Nobel N.V. | Solutions stabilisées de peroxyde d'hydrogène |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060546A (en) * | 1961-07-03 | 1977-11-29 | Henkel Kommanditgesellschaft Auf Aktien | Process for the manufacture of acylation products of phosphorous acid |
| US3361528A (en) * | 1964-09-08 | 1968-01-02 | Monsanto Co | Purification of orthophosphorous acid |
| DE1261850B (de) * | 1965-03-30 | 1968-02-29 | Procter & Gamble | Verfahren zur Herstellung von AEthan-1-hydroxy-1,1-diphosphonsaeure |
| US3532461A (en) * | 1966-07-20 | 1970-10-06 | Procter & Gamble | Process for preparing chemical compounds containing trivalent phosphorus |
| US3504018A (en) * | 1966-12-19 | 1970-03-31 | Monsanto Co | Process for preparing phosphonic acids |
| US3870750A (en) * | 1969-11-19 | 1975-03-11 | Henkel & Cie Gmbh | Process for the production of aminomethane-diphosphonic acid and its salts |
| DE2203340C3 (de) * | 1972-01-25 | 1974-06-12 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Verfahren zur Herstellung von 1-Aminoäthan-l.l-diphosphonsäure sowie am Stickstoff substituierte Derivate davon |
| DE2543349C2 (de) * | 1975-09-29 | 1984-05-10 | Henkel KGaA, 4000 Düsseldorf | Preaparate zur herstellung von99m technetium-radiagnostica |
| DE2625767C3 (de) * | 1976-06-09 | 1980-06-04 | Benckiser-Knapsack Gmbh, 6802 Ladenburg | Verfahren zur Herstellung von 1-Aminoalkan-1,1 -diphosphonsäuren |
| US4163733A (en) * | 1977-10-25 | 1979-08-07 | Buckman Laboratories, Inc. | Synergistic compositions for corrosion and scale control |
| DE2722539C3 (de) * | 1977-05-18 | 1981-11-19 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Verfahren zur Herstellung der N,N-Dimethylaminomethan-diphosphonsäure |
| DE2846835A1 (de) * | 1978-10-27 | 1980-05-08 | Benckiser Knapsack Gmbh | Verfahren zur herstellung von carboxylalkan-aminoalkan-diphosphonsaeuren und -aminoarylalkan-diphosphonsaeuren |
-
1980
- 1980-12-13 DE DE19803047107 patent/DE3047107A1/de not_active Withdrawn
-
1981
- 1981-11-19 EP EP81109762A patent/EP0054195B1/fr not_active Expired
- 1981-11-19 DE DE8181109762T patent/DE3163672D1/de not_active Expired
- 1981-11-27 CA CA000391084A patent/CA1169091A/fr not_active Expired
- 1981-12-07 US US06/327,888 patent/US4418019A/en not_active Expired - Fee Related
- 1981-12-11 DD DD81235680A patent/DD206380A5/de unknown
- 1981-12-14 JP JP56200236A patent/JPS57123197A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1169091A (fr) | 1984-06-12 |
| JPS57123197A (en) | 1982-07-31 |
| EP0054195B1 (fr) | 1984-05-16 |
| DE3163672D1 (en) | 1984-06-20 |
| US4418019A (en) | 1983-11-29 |
| EP0054195A3 (en) | 1982-08-11 |
| EP0054195A2 (fr) | 1982-06-23 |
| DE3047107A1 (de) | 1982-07-29 |
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