DE3133308C2 - - Google Patents
Info
- Publication number
- DE3133308C2 DE3133308C2 DE19813133308 DE3133308A DE3133308C2 DE 3133308 C2 DE3133308 C2 DE 3133308C2 DE 19813133308 DE19813133308 DE 19813133308 DE 3133308 A DE3133308 A DE 3133308A DE 3133308 C2 DE3133308 C2 DE 3133308C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- temperature
- phosphorous acid
- acetic anhydride
- reaction
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
- 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 description 14
- 239000002253 acid Substances 0.000 claims description 8
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 6
- 239000012346 acetyl chloride Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003948 formamides Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- -1 N, N-dimethylaminomethane diphosphonic acid N, N-dimethylformamide Chemical compound 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 229960000583 acetic acid Drugs 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 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 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
- 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
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
- 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 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
- 238000001816 cooling Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 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
- 229940082150 encore Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 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
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical group CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 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 DE3133308A1 (de) | 1983-03-17 |
| DE3133308C2 true 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) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102018119835A1 (de) | 2018-08-15 | 2020-02-20 | Chemische Fabrik Budenheim Kg | Polymerzusammensetzung mit Phosphonatflammschutzmittel |
| EP3860956B1 (en) | 2018-10-03 | 2024-11-27 | Italmatch Chemicals S.p.A. | Process for manufacturing n-alkyl-diphosphonate amino aminoacids |
| 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL280424A (enExample) * | 1961-07-03 | |||
| US3366677A (en) * | 1965-05-13 | 1968-01-30 | Procter & Gamble | Low temperature preparation of ethane-1-hydroxy-1, 1-diphosphonic acid |
| DE1958123C3 (de) * | 1969-11-19 | 1978-09-28 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur Herstellung von 1 -Aminoalkan-1,1 -diphosphonsäuren oder deren Salzen |
| DE2048912C3 (de) * | 1970-10-06 | 1980-07-31 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur Herstellung von l-Aminoalkan-l.l-diphosphonsäuren |
| US3899496A (en) * | 1970-10-06 | 1975-08-12 | Henkel & Cie Gmbh | Production of 1-aminoalkane-1,1-diphosphonic acids |
| DE2504724C3 (de) * | 1975-02-05 | 1979-08-09 | Benckiser-Knapsack Gmbh, 6802 Ladenburg | N-Hydroxyalkan-aminoalkan-diphosphonsäuren und deren Alkalisalze |
| DE2530139C3 (de) * | 1975-04-30 | 1979-06-21 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | N-Acyl-1 -aminoalkan-1,1 -diphosphonsäuren, deren Herstellung und Verwendung |
| DE2651904C2 (de) * | 1976-11-13 | 1983-01-05 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Verfahren zur Herstellung von N-Acyl-N-alkylaminomethandiphosphonsäuren |
| DE2722539C3 (de) * | 1977-05-18 | 1981-11-19 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Verfahren zur Herstellung der N,N-Dimethylaminomethan-diphosphonsäure |
| DE2738763C3 (de) * | 1977-08-27 | 1981-06-19 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Verfahren zur Herstellung von 1-Aminoäthan-1,1-diphosphonsäure sowie am Stickstoff substituierte Derivate davon |
-
1981
- 1981-08-22 DE DE19813133308 patent/DE3133308A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3133308A1 (de) | 1983-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AG | Has addition no. |
Ref country code: DE Ref document number: 3232754 Format of ref document f/p: P |
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| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| 8181 | Inventor (new situation) |
Free format text: ANTRAG AUF TEILNICHTNENNUNG |
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| AG | Has addition no. |
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| 8110 | Request for examination paragraph 44 | ||
| 8181 | Inventor (new situation) |
Free format text: SOMMER, KLAUS, PROF. DR., 6900 HEIDELBERG, DE SCHEUER, GERHARD F., DR., 6941 LAUDENBACH, DE BRODT, RAINER, 6204 TAUNUSSTEIN, DE |
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| AG | Has addition no. |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| AG | Has addition no. |
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| 8339 | Ceased/non-payment of the annual fee |