GB1036265A - Process for the production of triaryl-phosphino-propionic acid betaines - Google Patents
Process for the production of triaryl-phosphino-propionic acid betainesInfo
- Publication number
- GB1036265A GB1036265A GB908265A GB908265A GB1036265A GB 1036265 A GB1036265 A GB 1036265A GB 908265 A GB908265 A GB 908265A GB 908265 A GB908265 A GB 908265A GB 1036265 A GB1036265 A GB 1036265A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphine
- acid
- phosphino
- triaryl
- acrylic acid
- 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YHDQREIQZMNEIG-UHFFFAOYSA-M (3-ethoxy-3-oxopropyl)-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC(=O)OCC)C1=CC=CC=C1 YHDQREIQZMNEIG-UHFFFAOYSA-M 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 abstract 1
- XSYRNUSGWCMYSP-UHFFFAOYSA-N 2-phosphanylpropanoic acid Chemical compound CC(P)C(O)=O XSYRNUSGWCMYSP-UHFFFAOYSA-N 0.000 abstract 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract 1
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229960003237 betaine Drugs 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- -1 phosphino betaine Chemical compound 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 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 abstract 1
- 229920006337 unsaturated polyester resin Polymers 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 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)
Abstract
Triaryl phosphino-propionic acid betaines are prepared by mixing acrylic acid or an a -alkyl or a -aryl derivative thereof with a triaryl phosphine optionally at an elevated temperature of up to about 80 DEG C. and/or in the presence of a solvent and then optionally heating the reaction mixture up to about 140 DEG C. and subsequently separating the reaction product. Acids specified acrylic acid a -methacrylic acid and a -phenylacrylic acid, specified triazyl phosphines are triphenyl phosphine, tritolyl phosphine and trio-chlorophenyl phosphine and suitable solvents are dioxan, tetrahydrofuran, ethyl acetate, acetonitrile and acetone. BETA-Carbethoxyethyl - triphenyl phosphoniumchloride and -iodide are obtained by boiling the reaction product of acrylic acid and triphenyl phosphine with ethanolic hydrochloric acid and alcoholic ethyl iodide respectively. The phosphino betaine products may be applied as accelerators in the hardening of unsaturated polyester resins, as flame protection agents and pest control agents for wood, textiles and synthetic resins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF42214A DE1200295B (en) | 1964-03-05 | 1964-03-05 | Process for the preparation of Triarylphosphinopropionsaeurebetainen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1036265A true GB1036265A (en) | 1966-07-20 |
Family
ID=7098990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB908265A Expired GB1036265A (en) | 1964-03-05 | 1965-03-03 | Process for the production of triaryl-phosphino-propionic acid betaines |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT250989B (en) |
| BE (1) | BE660600A (en) |
| CH (1) | CH437279A (en) |
| DE (1) | DE1200295B (en) |
| FR (1) | FR1434364A (en) |
| GB (1) | GB1036265A (en) |
| NL (1) | NL6501547A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2540260C2 (en) * | 1975-09-10 | 1984-03-01 | Hoechst Ag, 6230 Frankfurt | Phosphor betaines and processes for their preparation |
| DE2540232C2 (en) * | 1975-09-10 | 1983-12-08 | Hoechst Ag, 6230 Frankfurt | Phosphor betaines and processes for their preparation |
-
1964
- 1964-03-05 DE DEF42214A patent/DE1200295B/en active Pending
-
1965
- 1965-01-18 CH CH64565A patent/CH437279A/en unknown
- 1965-02-08 NL NL6501547A patent/NL6501547A/xx unknown
- 1965-02-15 AT AT130465A patent/AT250989B/en active
- 1965-02-25 FR FR7042A patent/FR1434364A/en not_active Expired
- 1965-03-03 GB GB908265A patent/GB1036265A/en not_active Expired
- 1965-03-04 BE BE660600D patent/BE660600A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6501547A (en) | 1965-09-06 |
| CH437279A (en) | 1967-06-15 |
| AT250989B (en) | 1966-12-12 |
| DE1200295B (en) | 1965-09-09 |
| FR1434364A (en) | 1966-04-08 |
| BE660600A (en) | 1965-07-01 |
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