DE1251759B - Verfahren zur kontinuierlichen Herstellung von Athan 1 hydroxy - 1 1-diphosphonsaure - Google Patents
Verfahren zur kontinuierlichen Herstellung von Athan 1 hydroxy - 1 1-diphosphonsaureInfo
- Publication number
- DE1251759B DE1251759B DENDAT1251759D DE1251759DA DE1251759B DE 1251759 B DE1251759 B DE 1251759B DE NDAT1251759 D DENDAT1251759 D DE NDAT1251759D DE 1251759D A DE1251759D A DE 1251759DA DE 1251759 B DE1251759 B DE 1251759B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- reaction
- continuously
- phosphorous
- hydroxy
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000010924 continuous production Methods 0.000 title claims description 12
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 151
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 150
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 93
- 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 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 238000002156 mixing Methods 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 6
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 description 49
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JUEYKTPAPHITRJ-UHFFFAOYSA-N acetic acid;phosphorous acid Chemical compound CC(O)=O.OP(O)O JUEYKTPAPHITRJ-UHFFFAOYSA-N 0.000 description 4
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- TYVWLCJTWHVKRD-UHFFFAOYSA-N acetylphosphonic acid Chemical class CC(=O)P(O)(O)=O TYVWLCJTWHVKRD-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000003381 stabilizer 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
- C07F9/28—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US443844A US3400147A (en) | 1965-03-30 | 1965-03-30 | Process for preparation of organophosphorous compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1251759B true DE1251759B (de) | 1967-10-12 |
Family
ID=23762404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1251759D Pending DE1251759B (de) | 1965-03-30 | Verfahren zur kontinuierlichen Herstellung von Athan 1 hydroxy - 1 1-diphosphonsaure |
Country Status (6)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496222A (en) * | 1967-12-28 | 1970-02-17 | Procter & Gamble | Diacetylated cyclic dimer of ethane-1-hydroxy - 1,1 - diphosphonic acid and salts thereof |
| US4088675A (en) * | 1976-03-15 | 1978-05-09 | Massachusetts Institute Of Technology | Production of acyl phosphate salts |
| DE3622786A1 (de) * | 1986-07-07 | 1988-02-04 | Benckiser Knapsack Gmbh | Verfahren zur herstellung von vinyldiphosphonsaeure und ihren salzen |
| EP2050785A1 (en) | 1997-10-31 | 2009-04-22 | Metabolix, Inc. | Use of organic phosphonic or phosphinic acids, or of oxides, hydroxides or carboxylic acid salts of metals as thermal stabilizers for plasticized polyhydroxyalcanoates |
| ES2530791T3 (es) | 2002-12-20 | 2015-03-05 | Hoffmann La Roche | Formulación de ibandronato de altas dosis |
| WO2015059288A1 (en) | 2013-10-25 | 2015-04-30 | Straitmark Holding Ag | Method for the synthesis of ethane-1-hydroxy-1,1-diphosphonic acid |
| CN110642887B (zh) * | 2019-10-17 | 2021-05-07 | 山东泰和水处理科技股份有限公司 | 一种羟基亚乙基二膦酸晶体的连续化生产方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2790837A (en) * | 1954-06-08 | 1957-04-30 | Celanese Corp | Continuous production of trimethylolethane |
| NL130828C (US08063081-20111122-C00044.png) * | 1959-06-03 | |||
| NL280424A (US08063081-20111122-C00044.png) * | 1961-07-03 | |||
| DE1202441B (de) * | 1963-03-02 | 1965-10-07 | Therachemie Chem Therapeut | Mittel zur Verminderung der Schaedigung von Haaren beim Bleichen und Faerben |
-
0
- DE DENDAT1251759D patent/DE1251759B/de active Pending
-
1965
- 1965-03-30 US US443844A patent/US3400147A/en not_active Expired - Lifetime
-
1966
- 1966-03-29 BE BE678616D patent/BE678616A/xx unknown
- 1966-03-29 CH CH454066A patent/CH487937A/de not_active IP Right Cessation
- 1966-03-30 GB GB14087/66A patent/GB1088587A/en not_active Expired
- 1966-03-30 NL NL6604221A patent/NL6604221A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3400147A (en) | 1968-09-03 |
| CH487937A (de) | 1970-03-31 |
| NL6604221A (US08063081-20111122-C00044.png) | 1966-10-03 |
| GB1088587A (en) | 1967-10-25 |
| BE678616A (US08063081-20111122-C00044.png) | 1966-09-29 |
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