DE3133308A1 - Verfahren zur herstellung von n-alkyl-aminomethandiphosphonsaeuren - Google Patents
Verfahren zur herstellung von n-alkyl-aminomethandiphosphonsaeurenInfo
- Publication number
- DE3133308A1 DE3133308A1 DE19813133308 DE3133308A DE3133308A1 DE 3133308 A1 DE3133308 A1 DE 3133308A1 DE 19813133308 DE19813133308 DE 19813133308 DE 3133308 A DE3133308 A DE 3133308A DE 3133308 A1 DE3133308 A1 DE 3133308A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acetic anhydride
- reaction
- phosphorous acid
- acetyl chloride
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 12
- 150000007513 acids Chemical class 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 48
- 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 claims abstract description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012346 acetyl chloride Substances 0.000 claims abstract description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000019253 formic acid Nutrition 0.000 claims abstract description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 239000011541 reaction mixture Substances 0.000 claims description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 150000003948 formamides Chemical class 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- -1 alkyl formamides Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical compound OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- BFDMEODWJJUORJ-UHFFFAOYSA-N [dimethylamino(phosphono)methyl]phosphonic acid Chemical compound CN(C)C(P(O)(O)=O)P(O)(O)=O BFDMEODWJJUORJ-UHFFFAOYSA-N 0.000 description 2
- KVUUQMDVROTSNI-UHFFFAOYSA-N [morpholin-4-yl(phosphono)methyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)N1CCOCC1 KVUUQMDVROTSNI-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- SRBATDDRZARFDZ-VKHMYHEASA-N (2s)-2-formamidopropanoic acid Chemical compound OC(=O)[C@H](C)NC=O SRBATDDRZARFDZ-VKHMYHEASA-N 0.000 description 1
- CGENPBMSAIVDAP-UHFFFAOYSA-N 2-[formyl(methyl)amino]acetic acid Chemical compound O=CN(C)CC(O)=O CGENPBMSAIVDAP-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ADZLWSMFHHHOBV-BYPYZUCNSA-N N-formyl-L-glutamic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC=O ADZLWSMFHHHOBV-BYPYZUCNSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
- AGQSGSYOSSBGLI-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)formamide Chemical compound OCCN(C=O)CCO AGQSGSYOSSBGLI-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 239000000725 suspension Substances 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
-
- 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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813133308 DE3133308A1 (de) | 1981-08-22 | 1981-08-22 | Verfahren zur herstellung von n-alkyl-aminomethandiphosphonsaeuren |
| DE19823232754 DE3232754A1 (de) | 1981-08-22 | 1982-09-03 | Verfahren zur herstellung von n-alkyl-aminomethan-diphosphonsaeuren |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813133308 DE3133308A1 (de) | 1981-08-22 | 1981-08-22 | Verfahren zur herstellung von n-alkyl-aminomethandiphosphonsaeuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3133308A1 true DE3133308A1 (de) | 1983-03-17 |
| DE3133308C2 DE3133308C2 (enExample) | 1989-08-10 |
Family
ID=6139919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813133308 Granted DE3133308A1 (de) | 1981-08-22 | 1981-08-22 | Verfahren zur herstellung von n-alkyl-aminomethandiphosphonsaeuren |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3133308A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109651584A (zh) * | 2018-11-20 | 2019-04-19 | 黎明化工研究设计院有限责任公司 | 一种反应型磷酸酯类阻燃剂及其制备方法和在聚氨酯泡沫中的应用 |
| WO2020035458A1 (de) | 2018-08-15 | 2020-02-20 | Chemische Fabrik Budenheim Kg | Polymerzusammensetzung mit phosphonatflammschutzmittel |
| WO2020070543A1 (en) | 2018-10-03 | 2020-04-09 | Italmatch Chemicals S.P.A. | Process for manufacturing n-alkyl-diphosphonate amino aminoacids |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148551B (de) * | 1961-07-03 | 1963-05-16 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Phosphonsaeuren bzw. deren Salzen mit mindestens 2 Phosphoratomen im Molekuel |
| US3366677A (en) * | 1965-05-13 | 1968-01-30 | Procter & Gamble | Low temperature preparation of ethane-1-hydroxy-1, 1-diphosphonic acid |
| DE1958123A1 (de) * | 1969-11-19 | 1971-05-19 | Henkel & Cie Gmbh | Verfahren zur Herstellung von 1-Aminoalkan-1,1-diphosphonsaeuren oder deren Salzen |
| DE2048912A1 (de) * | 1970-10-06 | 1972-04-13 | Henkel & Cie GmbH, 4000 Dusseldorf | Verfahren zur Herstellung von 1 Ami no alkan 1,1 diphosphonsauren |
| US3899496A (en) * | 1970-10-06 | 1975-08-12 | Henkel & Cie Gmbh | Production of 1-aminoalkane-1,1-diphosphonic acids |
| DE2439355A1 (de) * | 1974-08-16 | 1976-02-26 | Benckiser Gmbh Joh A | N-(diphosphonomethyl)-formamidine und verfahren zur herstellung |
| DE2504724A1 (de) * | 1975-02-05 | 1976-08-19 | Benckiser Knapsack Gmbh | N-hydroxyalkan-aminoalkan-diphosphonsaeuren und deren alkalisalze |
| DE2530139A1 (de) * | 1975-04-30 | 1977-01-20 | Benckiser Gmbh Joh A | N-acyl-1-aminoalkan-1,1-diphosphonsaeuren, deren herstellung und verwendung |
| DE2651904A1 (de) * | 1976-11-13 | 1978-05-18 | Benckiser Gmbh Joh A | Verfahren zur herstellung von n-acyl-n-alkylaminomethandiphosphonsaeuren |
| DE2722539A1 (de) * | 1977-05-18 | 1978-11-23 | Benckiser Gmbh Joh A | Verfahren zur herstellung der n,n-dimethylamino-methan-diphosphonsaeure |
| DE2738763A1 (de) * | 1977-08-27 | 1979-03-08 | Benckiser Gmbh Joh A | Verfahren zur herstellung von 1-aminoaethan-1,1-diphosphonsaeure sowie am stickstoff substituierte derivate davon |
-
1981
- 1981-08-22 DE DE19813133308 patent/DE3133308A1/de active Granted
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148551B (de) * | 1961-07-03 | 1963-05-16 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Phosphonsaeuren bzw. deren Salzen mit mindestens 2 Phosphoratomen im Molekuel |
| US3366677A (en) * | 1965-05-13 | 1968-01-30 | Procter & Gamble | Low temperature preparation of ethane-1-hydroxy-1, 1-diphosphonic acid |
| DE1958123A1 (de) * | 1969-11-19 | 1971-05-19 | Henkel & Cie Gmbh | Verfahren zur Herstellung von 1-Aminoalkan-1,1-diphosphonsaeuren oder deren Salzen |
| DE2048912A1 (de) * | 1970-10-06 | 1972-04-13 | Henkel & Cie GmbH, 4000 Dusseldorf | Verfahren zur Herstellung von 1 Ami no alkan 1,1 diphosphonsauren |
| US3899496A (en) * | 1970-10-06 | 1975-08-12 | Henkel & Cie Gmbh | Production of 1-aminoalkane-1,1-diphosphonic acids |
| DE2439355A1 (de) * | 1974-08-16 | 1976-02-26 | Benckiser Gmbh Joh A | N-(diphosphonomethyl)-formamidine und verfahren zur herstellung |
| DE2504724A1 (de) * | 1975-02-05 | 1976-08-19 | Benckiser Knapsack Gmbh | N-hydroxyalkan-aminoalkan-diphosphonsaeuren und deren alkalisalze |
| FR2344565A1 (fr) * | 1975-02-05 | 1977-10-14 | Benckiser Knapsack Gmbh | Acides diphosphoniques et leurs sels alcalins, procede de preparation et utilisation comme complexants adoucisseurs d'eau |
| DE2530139A1 (de) * | 1975-04-30 | 1977-01-20 | Benckiser Gmbh Joh A | N-acyl-1-aminoalkan-1,1-diphosphonsaeuren, deren herstellung und verwendung |
| DE2651904A1 (de) * | 1976-11-13 | 1978-05-18 | Benckiser Gmbh Joh A | Verfahren zur herstellung von n-acyl-n-alkylaminomethandiphosphonsaeuren |
| DE2722539A1 (de) * | 1977-05-18 | 1978-11-23 | Benckiser Gmbh Joh A | Verfahren zur herstellung der n,n-dimethylamino-methan-diphosphonsaeure |
| DE2738763A1 (de) * | 1977-08-27 | 1979-03-08 | Benckiser Gmbh Joh A | Verfahren zur herstellung von 1-aminoaethan-1,1-diphosphonsaeure sowie am stickstoff substituierte derivate davon |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020035458A1 (de) | 2018-08-15 | 2020-02-20 | Chemische Fabrik Budenheim Kg | Polymerzusammensetzung mit phosphonatflammschutzmittel |
| WO2021028496A1 (de) | 2018-08-15 | 2021-02-18 | Chemische Fabrik Budenheim Kg | Polymerzusammensetzung mit phosphonatflammschutzmittel |
| US11692077B2 (en) | 2018-08-15 | 2023-07-04 | Chemische Fabrik Budenheim Kg | Polymer composition containing a phosphonate flame retardant |
| WO2020070543A1 (en) | 2018-10-03 | 2020-04-09 | Italmatch Chemicals S.P.A. | Process for manufacturing n-alkyl-diphosphonate amino aminoacids |
| CN109651584A (zh) * | 2018-11-20 | 2019-04-19 | 黎明化工研究设计院有限责任公司 | 一种反应型磷酸酯类阻燃剂及其制备方法和在聚氨酯泡沫中的应用 |
| CN109651584B (zh) * | 2018-11-20 | 2021-10-08 | 黎明化工研究设计院有限责任公司 | 一种反应型含磷类阻燃剂及其制备方法和在聚氨酯泡沫中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3133308C2 (enExample) | 1989-08-10 |
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