DE3142517A1 - Verfahren zur herstellung eines phosphonsaeuregemisches - Google Patents
Verfahren zur herstellung eines phosphonsaeuregemischesInfo
- Publication number
- DE3142517A1 DE3142517A1 DE19813142517 DE3142517A DE3142517A1 DE 3142517 A1 DE3142517 A1 DE 3142517A1 DE 19813142517 DE19813142517 DE 19813142517 DE 3142517 A DE3142517 A DE 3142517A DE 3142517 A1 DE3142517 A1 DE 3142517A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- alkenoic
- acids
- phosphorus trichloride
- preparation
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims abstract description 25
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 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 13
- 150000001805 chlorine compounds Chemical class 0.000 claims abstract description 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract description 3
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 abstract description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract description 2
- -1 for example Chemical class 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 abstract 1
- JJYWRQLLQAKNAD-UHFFFAOYSA-N 2-Methyl-2-pentenoic acid Natural products CCC=C(C)C(O)=O JJYWRQLLQAKNAD-UHFFFAOYSA-N 0.000 abstract 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 abstract 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000007792 addition Methods 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DOAAIMWVMVKYJZ-UHFFFAOYSA-N (1-hydroxy-1,3-diphosphonopropyl)phosphonic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CCP(O)(O)=O DOAAIMWVMVKYJZ-UHFFFAOYSA-N 0.000 description 1
- RWMGBQSQSUINCC-UHFFFAOYSA-N (1-hydroxy-2-methyl-1,3-diphosphonopropyl)phosphonic acid Chemical compound CC(C(P(O)(=O)O)(P(O)(=O)O)O)CP(O)(=O)O RWMGBQSQSUINCC-UHFFFAOYSA-N 0.000 description 1
- PRGRZSBNGHPEKD-UHFFFAOYSA-N (4-hydroxy-4,4-diphosphonobutan-2-yl)phosphonic acid Chemical compound OC(CC(C)P(O)(=O)O)(P(O)(=O)O)P(O)(=O)O PRGRZSBNGHPEKD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NLBSQHGCGGFVJW-UHFFFAOYSA-N 2-carboxyethylphosphonic acid Chemical compound OC(=O)CCP(O)(O)=O NLBSQHGCGGFVJW-UHFFFAOYSA-N 0.000 description 1
- XQYRPBCOMLASMG-UHFFFAOYSA-N 2-methyl-2-phosphonopropanoic acid Chemical compound OC(=O)C(C)(C)P(O)(O)=O XQYRPBCOMLASMG-UHFFFAOYSA-N 0.000 description 1
- GUXRZQZCNOHHDO-UHFFFAOYSA-N 2-phosphonopropanoic acid Chemical compound OC(=O)C(C)P(O)(O)=O GUXRZQZCNOHHDO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 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
- C07F9/3882—Arylalkanephosphonic 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
- C07F9/28—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
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813142517 DE3142517A1 (de) | 1981-10-27 | 1981-10-27 | Verfahren zur herstellung eines phosphonsaeuregemisches |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813142517 DE3142517A1 (de) | 1981-10-27 | 1981-10-27 | Verfahren zur herstellung eines phosphonsaeuregemisches |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3142517A1 true DE3142517A1 (de) | 1983-05-05 |
| DE3142517C2 DE3142517C2 (enExample) | 1990-12-13 |
Family
ID=6144902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813142517 Granted DE3142517A1 (de) | 1981-10-27 | 1981-10-27 | Verfahren zur herstellung eines phosphonsaeuregemisches |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3142517A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0451596A1 (en) * | 1990-04-12 | 1991-10-16 | ALBRIGHT & WILSON LIMITED | Phosphonylation process |
| EP0491391A1 (en) * | 1990-12-18 | 1992-06-24 | ALBRIGHT & WILSON UK LIMITED | Water treatment agent |
| EP0569731A3 (en) * | 1992-04-16 | 1994-05-25 | Albright & Wilson | Water treatment agent |
| US5386038A (en) * | 1990-12-18 | 1995-01-31 | Albright & Wilson Limited | Water treatment agent |
| WO1998047906A1 (en) * | 1997-04-24 | 1998-10-29 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
| US5977090A (en) * | 1996-09-27 | 1999-11-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating compulsive disorders using NAALADase inhibitors |
| US9730795B2 (en) | 2000-11-20 | 2017-08-15 | Universite De Geneve | Endosseous implant |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148235B (de) * | 1961-07-03 | 1963-05-09 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Acylierungsprodukten der phosphorigen Saeure mit mindestens 2 Phosphoratomen im Molekuel |
| DE2130794A1 (de) * | 1971-06-22 | 1973-01-11 | Benckiser Gmbh Joh A | 1-hydroxy-3-amino-propan-1,1-diphosphonsaeure und verfahren zu deren herstellung |
| DE2745083A1 (de) * | 1977-10-07 | 1979-04-12 | Henkel Kgaa | Hydroxydiphosphonsaeuren |
-
1981
- 1981-10-27 DE DE19813142517 patent/DE3142517A1/de active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1148235B (de) * | 1961-07-03 | 1963-05-09 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Acylierungsprodukten der phosphorigen Saeure mit mindestens 2 Phosphoratomen im Molekuel |
| DE2130794A1 (de) * | 1971-06-22 | 1973-01-11 | Benckiser Gmbh Joh A | 1-hydroxy-3-amino-propan-1,1-diphosphonsaeure und verfahren zu deren herstellung |
| DE2745083A1 (de) * | 1977-10-07 | 1979-04-12 | Henkel Kgaa | Hydroxydiphosphonsaeuren |
Non-Patent Citations (4)
| Title |
|---|
| HOUBEN-WEYL: Methoden der organischen Chemie, 1963, 360, 361 * |
| Mh. Chem. 99, 1968, 2016 * |
| Z. anorg. allg. Chem. 381, 1971, 247 * |
| Zhurn. obse. Khim. 28, 1968, 377 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2242902A (en) * | 1990-04-12 | 1991-10-16 | Albright & Wilson | Phosphonylation processes |
| GB2242902B (en) * | 1990-04-12 | 1993-10-06 | Albright & Wilson | Phosphonylation processes |
| EP0451596A1 (en) * | 1990-04-12 | 1991-10-16 | ALBRIGHT & WILSON LIMITED | Phosphonylation process |
| JP3225213B2 (ja) | 1990-12-18 | 2001-11-05 | ローディア・コンスーマー・スペシャルティーズ・リミテッド | マレイン酸のホスホン化オリゴマー |
| EP0491391A1 (en) * | 1990-12-18 | 1992-06-24 | ALBRIGHT & WILSON UK LIMITED | Water treatment agent |
| US5386038A (en) * | 1990-12-18 | 1995-01-31 | Albright & Wilson Limited | Water treatment agent |
| EP0569731A3 (en) * | 1992-04-16 | 1994-05-25 | Albright & Wilson | Water treatment agent |
| US5977090A (en) * | 1996-09-27 | 1999-11-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating compulsive disorders using NAALADase inhibitors |
| WO1998047906A1 (en) * | 1997-04-24 | 1998-10-29 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
| US6288046B1 (en) | 1997-04-24 | 2001-09-11 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
| US6054444A (en) * | 1997-04-24 | 2000-04-25 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
| US9730795B2 (en) | 2000-11-20 | 2017-08-15 | Universite De Geneve | Endosseous implant |
| EP1698357B1 (en) * | 2000-11-20 | 2019-06-26 | Universite De Geneve | Polyphosphonic acids and derivatives thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3142517C2 (enExample) | 1990-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |