SU509240A3 - Способ получени -оксибензил-фосфонатов - Google Patents
Способ получени -оксибензил-фосфонатовInfo
- Publication number
- SU509240A3 SU509240A3 SU1749596A SU1749596A SU509240A3 SU 509240 A3 SU509240 A3 SU 509240A3 SU 1749596 A SU1749596 A SU 1749596A SU 1749596 A SU1749596 A SU 1749596A SU 509240 A3 SU509240 A3 SU 509240A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- hydroxy
- mixture
- tert
- heated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- -1 alkyloxalkyl Chemical group 0.000 claims description 12
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003385 sodium Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- ZHBRSHSRMYZHLS-UHFFFAOYSA-N (4-hydroxyphenyl)methylphosphonic acid Chemical class OC1=CC=C(CP(O)(O)=O)C=C1 ZHBRSHSRMYZHLS-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- ITOCRZXQUJQDPI-UHFFFAOYSA-N 1-[2,3-bis(2,4,4-trimethylpentan-2-yl)phenoxy]-2,3-bis(2,4,4-trimethylpentan-2-yl)benzene Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC(OC=2C(=C(C=CC=2)C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C)=C1C(C)(C)CC(C)(C)C ITOCRZXQUJQDPI-UHFFFAOYSA-N 0.000 description 1
- YJKXQPLKEYFHKG-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethylaminomethyl)phenol Chemical compound CCN(CC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YJKXQPLKEYFHKG-UHFFFAOYSA-N 0.000 description 1
- KWGUJRCPGGSTKB-UHFFFAOYSA-N 2,6-ditert-butyl-4-(morpholin-4-ylmethyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2CCOCC2)=C1 KWGUJRCPGGSTKB-UHFFFAOYSA-N 0.000 description 1
- ZGSGBCBFJJASJA-UHFFFAOYSA-N 2-[3-(methylamino)propylamino]ethylsulfanylphosphonic acid Chemical compound CNCCCNCCSP(O)(O)=O ZGSGBCBFJJASJA-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- LCWKIAHCEIHHJE-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2,6-dimethylphenol Chemical compound CN(C)CC1=CC(C)=C(O)C(C)=C1 LCWKIAHCEIHHJE-UHFFFAOYSA-N 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- BAKDLAFAVHBXHW-UHFFFAOYSA-N dioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP([O-])OCCCCCCCCCCCCCCCCCC BAKDLAFAVHBXHW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
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)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH231571A CH542248A (de) | 1971-02-17 | 1971-02-17 | Verfahren zur Herstellung von Benzylphosphonaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU509240A3 true SU509240A3 (ru) | 1976-03-30 |
Family
ID=4230916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1749596A SU509240A3 (ru) | 1971-02-17 | 1972-02-16 | Способ получени -оксибензил-фосфонатов |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3790648A (enExample) |
| AT (1) | AT309466B (enExample) |
| BE (1) | BE779422A (enExample) |
| CA (1) | CA926871A (enExample) |
| CH (1) | CH542248A (enExample) |
| DE (1) | DE2203837C3 (enExample) |
| FR (1) | FR2125515B1 (enExample) |
| GB (1) | GB1365622A (enExample) |
| IT (1) | IT950550B (enExample) |
| NL (1) | NL7202041A (enExample) |
| SU (1) | SU509240A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4131951A1 (de) * | 1991-09-25 | 1993-04-08 | Boehme Chem Fab Kg | Wasserloesliche bzw. dispergierbare mittel zur stabilisierung thermooxidativ labiler verbindungen |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3962377A (en) * | 1973-09-25 | 1976-06-08 | Ciba-Geigy Corporation | 2,3,5-Trialkyl-4-hydroxybenzylphosphonates and phosphinates |
| US3962376A (en) * | 1973-09-25 | 1976-06-08 | Ciba-Geigy Corporation | 2,4,6-Trialkyl-3-hydroxyphenylalkane phosphonates and phosphinates |
| USB512373I5 (enExample) * | 1974-10-07 | 1976-02-10 | ||
| US4008199A (en) * | 1975-06-09 | 1977-02-15 | Celanese Corporation | Heat stabilized polyalkylene terephthalate resin composition |
| JPS5379935A (en) * | 1976-12-24 | 1978-07-14 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
| US4263232A (en) * | 1979-07-09 | 1981-04-21 | Ciba-Geigy Corporation | Process for the manufacture of selected phosphonates |
| US5258540A (en) * | 1989-11-29 | 1993-11-02 | Ciba-Geigy Corporation | Cyclohexyl substituted hydroxybenyzlphosphonates |
| DE59009533D1 (de) * | 1989-11-29 | 1995-09-21 | Ciba Geigy Ag | Hydroxybenzylphosphonate und Verfahren zu ihrer Herstellung. |
| DE59206764D1 (de) * | 1991-04-05 | 1996-08-22 | Ciba Geigy Ag | Verfahren zur Herstellung von sterisch gehinderten Hydroxybenzylphosphonaten |
| DE4128509A1 (de) * | 1991-08-28 | 1993-03-04 | Basf Ag | Thermooxidationsbestaendige thermoplastische formmassen |
| US5756596A (en) * | 1993-12-16 | 1998-05-26 | Ciba Specialty Chemicals Corporation | Increasing the molecular weight of polyamides |
| TW283707B (enExample) | 1994-06-28 | 1996-08-21 | Ciba Geigy Ag | |
| EP0816354A1 (de) * | 1996-06-25 | 1998-01-07 | Bayer Ag | Verfahren zur Herstellung und Stabilisierung von aliphatischen Sechsringcarbonaten |
| WO2003026632A2 (en) * | 2001-09-26 | 2003-04-03 | Theravance, Inc. | Substituted phenol compounds useful for anesthesia and sedation |
| CN119708054A (zh) * | 2024-12-12 | 2025-03-28 | 中国科学院兰州化学物理研究所 | 一种抗氧抗磨双功能润滑添加剂、制备方法及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1917512A1 (de) * | 1969-04-05 | 1970-10-15 | Advance Prod Gmbh | phosphonessigsaeureester |
-
1971
- 1971-02-17 CH CH231571A patent/CH542248A/de not_active IP Right Cessation
-
1972
- 1972-01-27 DE DE2203837A patent/DE2203837C3/de not_active Expired
- 1972-02-11 CA CA134496A patent/CA926871A/en not_active Expired
- 1972-02-11 US US00225615A patent/US3790648A/en not_active Expired - Lifetime
- 1972-02-16 FR FR7205189A patent/FR2125515B1/fr not_active Expired
- 1972-02-16 IT IT20636/72A patent/IT950550B/it active
- 1972-02-16 NL NL7202041A patent/NL7202041A/xx unknown
- 1972-02-16 BE BE779422A patent/BE779422A/xx unknown
- 1972-02-16 AT AT124872A patent/AT309466B/de not_active IP Right Cessation
- 1972-02-16 SU SU1749596A patent/SU509240A3/ru active
- 1972-02-17 GB GB736672A patent/GB1365622A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4131951A1 (de) * | 1991-09-25 | 1993-04-08 | Boehme Chem Fab Kg | Wasserloesliche bzw. dispergierbare mittel zur stabilisierung thermooxidativ labiler verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2203837C3 (de) | 1981-07-23 |
| GB1365622A (en) | 1974-09-04 |
| FR2125515B1 (enExample) | 1974-09-13 |
| BE779422A (fr) | 1972-08-16 |
| US3790648A (en) | 1974-02-05 |
| CA926871A (en) | 1973-05-22 |
| NL7202041A (enExample) | 1972-08-21 |
| DE2203837B2 (de) | 1980-06-26 |
| AT309466B (de) | 1973-08-27 |
| CH542248A (de) | 1973-09-30 |
| FR2125515A1 (enExample) | 1972-09-29 |
| DE2203837A1 (de) | 1972-08-31 |
| IT950550B (it) | 1973-06-20 |
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