DE2518144A1 - Verfahren zur herstellung von carboxyalkan-phosphonsaeuren und carboxy-alkylphosphinsaeuren - Google Patents
Verfahren zur herstellung von carboxyalkan-phosphonsaeuren und carboxy-alkylphosphinsaeurenInfo
- Publication number
- DE2518144A1 DE2518144A1 DE19752518144 DE2518144A DE2518144A1 DE 2518144 A1 DE2518144 A1 DE 2518144A1 DE 19752518144 DE19752518144 DE 19752518144 DE 2518144 A DE2518144 A DE 2518144A DE 2518144 A1 DE2518144 A1 DE 2518144A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formic acid
- acid
- phosphonic
- acids
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims description 26
- 150000007513 acids Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 title claims description 5
- 150000003009 phosphonic acids Chemical class 0.000 title 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 64
- 235000019253 formic acid Nutrition 0.000 claims description 32
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 21
- -1 R = H Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000002976 peresters Chemical group 0.000 claims 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 14
- 125000004185 ester group Chemical group 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- NLBSQHGCGGFVJW-UHFFFAOYSA-N 2-carboxyethylphosphonic acid Chemical compound OC(=O)CCP(O)(O)=O NLBSQHGCGGFVJW-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- KMDMOMDSEVTJTI-UHFFFAOYSA-N 2-phosphonobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)P(O)(O)=O KMDMOMDSEVTJTI-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- NFNJSHKCMHAXJJ-UHFFFAOYSA-N 2-methyl-3-phosphonopropanoic acid Chemical compound OC(=O)C(C)CP(O)(O)=O NFNJSHKCMHAXJJ-UHFFFAOYSA-N 0.000 description 2
- ZQKIEZGLXJMDRQ-UHFFFAOYSA-N 3-phosphonobutanoic acid Chemical compound OP(=O)(O)C(C)CC(O)=O ZQKIEZGLXJMDRQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- QXFUBAAEKCHBQY-UHFFFAOYSA-N 3-[hydroxy(methyl)phosphoryl]propanoic acid Chemical compound CP(O)(=O)CCC(O)=O QXFUBAAEKCHBQY-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012897 dilution medium Substances 0.000 description 1
- LGAMILCIMHCDPT-UHFFFAOYSA-N dimethyl 2-dimethoxyphosphorylbutanedioate Chemical compound COC(=O)CC(C(=O)OC)P(=O)(OC)OC LGAMILCIMHCDPT-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 231100000317 environmental toxin Toxicity 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JKEOPDKWEMKLKI-UHFFFAOYSA-N methyl 3-diethoxyphosphoryl-2-methylpropanoate Chemical compound CCOP(=O)(OCC)CC(C)C(=O)OC JKEOPDKWEMKLKI-UHFFFAOYSA-N 0.000 description 1
- YAZPRBJVHXOTIE-UHFFFAOYSA-N methyl 3-dimethoxyphosphorylbutanoate Chemical compound COC(=O)CC(C)P(=O)(OC)OC YAZPRBJVHXOTIE-UHFFFAOYSA-N 0.000 description 1
- DUCGXDQPWFCMNZ-UHFFFAOYSA-N methyl 3-dimethoxyphosphorylpropanoate Chemical compound COC(=O)CCP(=O)(OC)OC DUCGXDQPWFCMNZ-UHFFFAOYSA-N 0.000 description 1
- XMWIUJOPBMXLOQ-UHFFFAOYSA-N methyl 3-dipropoxyphosphorylpropanoate Chemical compound CCCOP(=O)(OCCC)CCC(=O)OC XMWIUJOPBMXLOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002699 waste material 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752518144 DE2518144A1 (de) | 1975-04-24 | 1975-04-24 | Verfahren zur herstellung von carboxyalkan-phosphonsaeuren und carboxy-alkylphosphinsaeuren |
| CH204876A CH597247A5 (xx) | 1975-04-24 | 1976-02-19 | |
| SE7601948A SE419090B (sv) | 1975-04-24 | 1976-02-19 | Sett att framstella karboxi-alkan-fosfonsyror och karboxi-alkyl-fosfinsyror |
| GB1024776A GB1497992A (en) | 1975-04-24 | 1976-03-15 | Production of carboxy-alkane-phosphonic acids and carboxy-alkyl-phosphinic acids |
| CA248,537A CA1036173A (en) | 1975-04-24 | 1976-03-23 | Production of carboxy-alkane-phosphonic acids and carboxy-alkyl-phosphinic acids |
| IT4908776A IT1058162B (it) | 1975-04-24 | 1976-04-20 | Procedimento per produrre acidi carbossialcan fosfonici ed acidi carbossialchil fosfonici |
| BE166317A BE840944A (fr) | 1975-04-24 | 1976-04-21 | Procede de preparation d'acides carboxy-alcane-phosphoniques et d'acides carboxy-alkyl-phosphiniques |
| NL7604372A NL7604372A (nl) | 1975-04-24 | 1976-04-23 | Werkwijze voor de bereiding van carboxyalkaan- fosfonzuren en carboxyalkylfosfienzuren. |
| FR7612162A FR2308634A1 (fr) | 1975-04-24 | 1976-04-23 | Procede de preparation d'acides carboxy-alcane-phosphoniques et d'acides carboxy-alkyl-phosphiniques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752518144 DE2518144A1 (de) | 1975-04-24 | 1975-04-24 | Verfahren zur herstellung von carboxyalkan-phosphonsaeuren und carboxy-alkylphosphinsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2518144A1 true DE2518144A1 (de) | 1976-11-04 |
Family
ID=5944849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752518144 Withdrawn DE2518144A1 (de) | 1975-04-24 | 1975-04-24 | Verfahren zur herstellung von carboxyalkan-phosphonsaeuren und carboxy-alkylphosphinsaeuren |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE840944A (xx) |
| CA (1) | CA1036173A (xx) |
| CH (1) | CH597247A5 (xx) |
| DE (1) | DE2518144A1 (xx) |
| FR (1) | FR2308634A1 (xx) |
| GB (1) | GB1497992A (xx) |
| IT (1) | IT1058162B (xx) |
| NL (1) | NL7604372A (xx) |
| SE (1) | SE419090B (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19613066A1 (de) * | 1996-04-01 | 1997-10-02 | Hoechst Ag | Verfahren zur Herstellung phosphormodifizierter Epoxidharze |
| US5773533A (en) * | 1996-04-01 | 1998-06-30 | Hoechst Aktiengesellschaft | Epoxy resin reacted with carboxy-functional phosphinic or phosphonic acid and hardener |
| WO2009113702A1 (en) * | 2008-03-14 | 2009-09-17 | Canon Kabushiki Kaisha | Ink jet recording medium and production process thereof, and fine particle dispersion |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977090A (en) * | 1996-09-27 | 1999-11-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating compulsive disorders using NAALADase inhibitors |
| US6054444A (en) | 1997-04-24 | 2000-04-25 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2229087B2 (de) * | 1972-06-15 | 1977-02-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von phosphon- und phosphinsaeuren durch verseifung von phosphon- und phosphinsaeureestern |
-
1975
- 1975-04-24 DE DE19752518144 patent/DE2518144A1/de not_active Withdrawn
-
1976
- 1976-02-19 CH CH204876A patent/CH597247A5/xx not_active IP Right Cessation
- 1976-02-19 SE SE7601948A patent/SE419090B/xx not_active IP Right Cessation
- 1976-03-15 GB GB1024776A patent/GB1497992A/en not_active Expired
- 1976-03-23 CA CA248,537A patent/CA1036173A/en not_active Expired
- 1976-04-20 IT IT4908776A patent/IT1058162B/it active
- 1976-04-21 BE BE166317A patent/BE840944A/xx not_active IP Right Cessation
- 1976-04-23 FR FR7612162A patent/FR2308634A1/fr active Granted
- 1976-04-23 NL NL7604372A patent/NL7604372A/xx not_active Application Discontinuation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19613066A1 (de) * | 1996-04-01 | 1997-10-02 | Hoechst Ag | Verfahren zur Herstellung phosphormodifizierter Epoxidharze |
| US5773533A (en) * | 1996-04-01 | 1998-06-30 | Hoechst Aktiengesellschaft | Epoxy resin reacted with carboxy-functional phosphinic or phosphonic acid and hardener |
| DE19613066C2 (de) * | 1996-04-01 | 1998-09-10 | Clariant Gmbh | Verfahren zur Herstellung phosphormodifizierter Epoxidharze |
| US5854361A (en) * | 1996-04-01 | 1998-12-29 | Hoechst Aktiengesellschaft | Process for preparing phosphorus-modified epoxy resins |
| WO2009113702A1 (en) * | 2008-03-14 | 2009-09-17 | Canon Kabushiki Kaisha | Ink jet recording medium and production process thereof, and fine particle dispersion |
| US8158223B2 (en) | 2008-03-14 | 2012-04-17 | Canon Kabushiki Kaisha | Ink jet recording medium and production process thereof, and fine particle dispersion |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1058162B (it) | 1982-04-10 |
| FR2308634B1 (xx) | 1980-12-26 |
| SE419090B (sv) | 1981-07-13 |
| BE840944A (fr) | 1976-10-21 |
| FR2308634A1 (fr) | 1976-11-19 |
| SE7601948L (sv) | 1976-10-25 |
| NL7604372A (nl) | 1976-10-26 |
| CH597247A5 (xx) | 1978-03-31 |
| GB1497992A (en) | 1978-01-12 |
| CA1036173A (en) | 1978-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |