DE1200295B - Verfahren zur Herstellung von Triarylphosphinopropionsaeurebetainen - Google Patents
Verfahren zur Herstellung von TriarylphosphinopropionsaeurebetainenInfo
- Publication number
- DE1200295B DE1200295B DEF42214A DEF0042214A DE1200295B DE 1200295 B DE1200295 B DE 1200295B DE F42214 A DEF42214 A DE F42214A DE F0042214 A DEF0042214 A DE F0042214A DE 1200295 B DE1200295 B DE 1200295B
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- reaction
- acid
- triphenylphosphine
- heated
- 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 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 7
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 7
- 229960003237 betaine Drugs 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- ASLOMEPLDWVVRG-UHFFFAOYSA-N 3-phenylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=CC1=CC=CC=C1 ASLOMEPLDWVVRG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- RIZPLDXMQXJTTJ-UHFFFAOYSA-N phosphane;prop-2-enoic acid Chemical compound [PH4+].[O-]C(=O)C=C RIZPLDXMQXJTTJ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- -1 β -carboxyethyl-triphenylphosphonium halides Chemical class 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- 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
- C08K5/50—Phosphorus bound to carbon only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF42214A DE1200295B (de) | 1964-03-05 | 1964-03-05 | Verfahren zur Herstellung von Triarylphosphinopropionsaeurebetainen |
CH64565A CH437279A (de) | 1964-03-05 | 1965-01-18 | Verfahren zur Herstellung von Triarylphosphinopropionsäurebetainen |
NL6501547A NL6501547A (US07118763-20061010-C00002.png) | 1964-03-05 | 1965-02-08 | |
AT130465A AT250989B (de) | 1964-03-05 | 1965-02-15 | Verfahren zur Herstellung von Triphenylphosphinopropionsäurebetain |
FR7042A FR1434364A (fr) | 1964-03-05 | 1965-02-25 | Procédé de préparation de bétaïnes d'acides triarylphosphinopropioniques |
GB908265A GB1036265A (en) | 1964-03-05 | 1965-03-03 | Process for the production of triaryl-phosphino-propionic acid betaines |
BE660600D BE660600A (US07118763-20061010-C00002.png) | 1964-03-05 | 1965-03-04 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF42214A DE1200295B (de) | 1964-03-05 | 1964-03-05 | Verfahren zur Herstellung von Triarylphosphinopropionsaeurebetainen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1200295B true DE1200295B (de) | 1965-09-09 |
Family
ID=7098990
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF42214A Pending DE1200295B (de) | 1964-03-05 | 1964-03-05 | Verfahren zur Herstellung von Triarylphosphinopropionsaeurebetainen |
Country Status (7)
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2540260A1 (de) * | 1975-09-10 | 1977-03-17 | Hoechst Ag | Phosphorbetaine und verfahren zu deren herstellung |
DE2540232A1 (de) * | 1975-09-10 | 1977-03-24 | Hoechst Ag | Phosphorbetaine und verfahren zu deren herstellung |
-
1964
- 1964-03-05 DE DEF42214A patent/DE1200295B/de active Pending
-
1965
- 1965-01-18 CH CH64565A patent/CH437279A/de unknown
- 1965-02-08 NL NL6501547A patent/NL6501547A/xx unknown
- 1965-02-15 AT AT130465A patent/AT250989B/de active
- 1965-02-25 FR FR7042A patent/FR1434364A/fr not_active Expired
- 1965-03-03 GB GB908265A patent/GB1036265A/en not_active Expired
- 1965-03-04 BE BE660600D patent/BE660600A/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2540260A1 (de) * | 1975-09-10 | 1977-03-17 | Hoechst Ag | Phosphorbetaine und verfahren zu deren herstellung |
DE2540232A1 (de) * | 1975-09-10 | 1977-03-24 | Hoechst Ag | Phosphorbetaine und verfahren zu deren herstellung |
Also Published As
Publication number | Publication date |
---|---|
NL6501547A (US07118763-20061010-C00002.png) | 1965-09-06 |
GB1036265A (en) | 1966-07-20 |
BE660600A (US07118763-20061010-C00002.png) | 1965-07-01 |
AT250989B (de) | 1966-12-12 |
FR1434364A (fr) | 1966-04-08 |
CH437279A (de) | 1967-06-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE1201839B (de) | Verfahren zur Herstellung aliphatischer Cyansaeureester, die durch elektronen-anziehende Atome oder Gruppen substituiert sind | |
DE2236036C3 (de) | Diphosphinsäureester | |
DE1248654B (de) | Verfahren zur Herstellung von Phosphonsäuren und deren Salzen | |
DE1200295B (de) | Verfahren zur Herstellung von Triarylphosphinopropionsaeurebetainen | |
DE2324390A1 (de) | Verfahren zur herstellung von derivaten des cyclopropans | |
DE1768943B2 (de) | Verfahren zur herstellung eines kobalt-chelatkomplexes | |
DE2264413A1 (de) | 2,4-diamino-5-(acyloxymethyl)pyrimidine | |
DE2238221A1 (de) | Dialkyl-phosphinyl-alkansulfonate und verfahren zu ihrer herstellung | |
DE2508188A1 (de) | Bis-(guanidinium)-tetrabromdian und verfahren zu dessen herstellung | |
EP0144743B1 (de) | Verfahren zur Herstellung organischer Chlorphosphane | |
EP0022546A2 (de) | Verfahren zur Herstellung von 1-Oxophospholan-chlorhydrinen sowie einige spezielle dieser Verbindungen | |
DE3605882A1 (de) | Verfahren zur herstellung von (alpha)-ketosaeuren | |
EP0202492B1 (de) | Phenyl-tetralindiphosphonsäuren sowie ein Verfahren zu ihrer Herstellung | |
CH616689A5 (US07118763-20061010-C00002.png) | ||
DE1184758B (de) | Verfahren zur Herstellung von Azo-bis-alkylphosphonaten und den entsprechenden Saeuren | |
DE1194852B (de) | Verfahren zur Herstellung von Phosphonsaeuren oder deren Salzen mit mindestens zwei Phosphoratomen im Molekuel | |
DE1237106B (de) | Verfahren zur Herstellung von Reaktionsprodukten von Decachloroctahydro-1, 3, 4-metheno-2H-cyclobuta(cd)pentalen-2-on mit Ketonen | |
EP0205820B1 (de) | Carboxytetralinphosphonsäuren sowie ein Verfahren zu ihrer Herstellung | |
DE2003860A1 (de) | Verfahren zur Herstellung von Benztriazolen | |
DE19955741C2 (de) | Verfahren zur Herstellung von Phosphinsäuren | |
DE1518060C (de) | 0.0-Dialkyl-S- eckige Klammer auf 2-(acetamido)-äthyl eckige Klammer zu -dithiophosphate und Verfahren zur Herstellung dieser Verbindungen | |
DE1207381B (de) | Verfahren zur Herstellung von 2-Hydroxy-2-methylmercapto-indandion-(1, 3) | |
DE1252680B (de) | Verfahren zur Herstellung von Phosphinsäureestern | |
DE1277254B (de) | Verfahren zur Herstellung von Diorganoantimon(ó¾)-acylaten | |
DE1148234B (de) | Verfahren zur gleichzeitigen Herstellung von substituierten dimeren und polymeren quaternaeren Phosphoniumsalzen |