DE1196195B - Verfahren zur Herstellung von Phosphonsaeureestern - Google Patents
Verfahren zur Herstellung von PhosphonsaeureesternInfo
- Publication number
- DE1196195B DE1196195B DEG37059A DEG0037059A DE1196195B DE 1196195 B DE1196195 B DE 1196195B DE G37059 A DEG37059 A DE G37059A DE G0037059 A DEG0037059 A DE G0037059A DE 1196195 B DE1196195 B DE 1196195B
- Authority
- DE
- Germany
- Prior art keywords
- phosphonic acid
- esters
- reaction
- acid esters
- added
- 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 10
- 150000003008 phosphonic acid esters Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- -1 hydrocarbon radical Chemical class 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NJLHHACGWKAWKL-UHFFFAOYSA-N ClP(Cl)=O Chemical class ClP(Cl)=O NJLHHACGWKAWKL-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- MRRAOBIIOMSKQB-UHFFFAOYSA-N dichlorophosphorylcyclohexane Chemical compound ClP(Cl)(=O)C1CCCCC1 MRRAOBIIOMSKQB-UHFFFAOYSA-N 0.000 description 1
- ZXYCEKFYEXXLHT-UHFFFAOYSA-N dichlorophosphorylcyclopentane Chemical compound ClP(Cl)(=O)C1CCCC1 ZXYCEKFYEXXLHT-UHFFFAOYSA-N 0.000 description 1
- KYCIUIVANPKXLW-UHFFFAOYSA-N dimethyl-(2-phenoxyethyl)-(thiophen-2-ylmethyl)azanium Chemical compound C=1C=CSC=1C[N+](C)(C)CCOC1=CC=CC=C1 KYCIUIVANPKXLW-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007127 saponification reaction Methods 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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
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)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG37059A DE1196195B (de) | 1963-02-14 | 1963-02-14 | Verfahren zur Herstellung von Phosphonsaeureestern |
| AT44564A AT248702B (de) | 1963-02-14 | 1964-01-21 | Verfahren zur Herstellung flammwidriger Polyester |
| AT44464A AT248456B (de) | 1963-02-14 | 1964-01-21 | Verfahern zur Herstellung von Phosphonsäureestern |
| BE643161A BE643161A (US20110009641A1-20110113-C00256.png) | 1963-02-14 | 1964-01-30 | |
| BE643328A BE643328A (US20110009641A1-20110113-C00256.png) | 1963-02-14 | 1964-02-04 | |
| NL6401071A NL6401071A (US20110009641A1-20110113-C00256.png) | 1963-02-14 | 1964-02-10 | |
| NL6401072A NL6401072A (US20110009641A1-20110113-C00256.png) | 1963-02-14 | 1964-02-10 | |
| GB564464A GB1048097A (en) | 1963-02-14 | 1964-02-11 | Production of phosphorus-containing polyesters and copolyesters |
| CH159364A CH431519A (de) | 1963-02-14 | 1964-02-11 | Verfahren zur Herstellung von Phosphonatverbindungen |
| FR963833A FR1382647A (fr) | 1963-02-14 | 1964-02-14 | Polyesters contenant du phosphore |
| FR963832A FR1382646A (fr) | 1963-02-14 | 1964-02-14 | Procédé de préparation de composés phosphoniques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG37059A DE1196195B (de) | 1963-02-14 | 1963-02-14 | Verfahren zur Herstellung von Phosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1196195B true DE1196195B (de) | 1965-07-08 |
Family
ID=7125543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG37059A Pending DE1196195B (de) | 1963-02-14 | 1963-02-14 | Verfahren zur Herstellung von Phosphonsaeureestern |
Country Status (6)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7101666B2 (ja) * | 2016-10-14 | 2022-07-15 | パフォーマンス・ポリアミデス，エスアエス | ポリアミド用リン含有コモノマー |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE814152C (de) * | 1951-07-26 | I arbenfabriken Bayer | everkusen I Verfahren zur Herstellung von Estern der Phosphorsaure und Thiophosphor saure | |
| DE949230C (de) * | 1955-04-03 | 1956-09-13 | Bayer Ag | Verfahren zur Herstellung von Thiolphosphorsaeure-S-alkyl-O, O-di-(carbalkoxyphenyl)-estern |
| US2945052A (en) * | 1955-03-10 | 1960-07-12 | Us Rubber Co | Preparation of dialkenyl phenyl phosphonates |
| DE1089376B (de) * | 1958-02-12 | 1960-09-22 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern bzw. Thiophosphonsaeureestern |
-
1963
- 1963-02-14 DE DEG37059A patent/DE1196195B/de active Pending
-
1964
- 1964-01-21 AT AT44564A patent/AT248702B/de active
- 1964-01-21 AT AT44464A patent/AT248456B/de active
- 1964-01-30 BE BE643161A patent/BE643161A/xx unknown
- 1964-02-04 BE BE643328A patent/BE643328A/xx unknown
- 1964-02-10 NL NL6401072A patent/NL6401072A/xx unknown
- 1964-02-10 NL NL6401071A patent/NL6401071A/xx unknown
- 1964-02-11 CH CH159364A patent/CH431519A/de unknown
- 1964-02-11 GB GB564464A patent/GB1048097A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE814152C (de) * | 1951-07-26 | I arbenfabriken Bayer | everkusen I Verfahren zur Herstellung von Estern der Phosphorsaure und Thiophosphor saure | |
| US2945052A (en) * | 1955-03-10 | 1960-07-12 | Us Rubber Co | Preparation of dialkenyl phenyl phosphonates |
| DE949230C (de) * | 1955-04-03 | 1956-09-13 | Bayer Ag | Verfahren zur Herstellung von Thiolphosphorsaeure-S-alkyl-O, O-di-(carbalkoxyphenyl)-estern |
| DE1089376B (de) * | 1958-02-12 | 1960-09-22 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern bzw. Thiophosphonsaeureestern |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6401071A (US20110009641A1-20110113-C00256.png) | 1964-08-17 |
| AT248456B (de) | 1966-07-25 |
| GB1048097A (en) | 1966-11-09 |
| NL6401072A (US20110009641A1-20110113-C00256.png) | 1964-08-17 |
| BE643328A (US20110009641A1-20110113-C00256.png) | 1964-05-29 |
| AT248702B (de) | 1966-08-10 |
| CH431519A (de) | 1967-03-15 |
| BE643161A (US20110009641A1-20110113-C00256.png) | 1964-05-15 |
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