DE2440239A1 - Innere ammoniumsalze von phosphinsaeuren - Google Patents
Innere ammoniumsalze von phosphinsaeurenInfo
- Publication number
- DE2440239A1 DE2440239A1 DE2440239A DE2440239A DE2440239A1 DE 2440239 A1 DE2440239 A1 DE 2440239A1 DE 2440239 A DE2440239 A DE 2440239A DE 2440239 A DE2440239 A DE 2440239A DE 2440239 A1 DE2440239 A1 DE 2440239A1
- Authority
- DE
- Germany
- Prior art keywords
- ammonium salts
- compounds
- methyl
- oxaphospholane
- alkyl
- 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- Withdrawn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 description 4
- 150000007513 acids Chemical class 0.000 title description 3
- 150000003863 ammonium salts Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OSNNATVBPNXCAF-UHFFFAOYSA-N 2-methyl-1,2$l^{5}-oxaphospholane 2-oxide Chemical compound CP1(=O)CCCO1 OSNNATVBPNXCAF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- -1 cyclic phosphinic acid esters Chemical class 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000004850 phospholanes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012619 stoichiometric conversion Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 239000008096 xylene 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
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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2440239A DE2440239A1 (de) | 1974-08-22 | 1974-08-22 | Innere ammoniumsalze von phosphinsaeuren |
| NL7509753A NL7509753A (nl) | 1974-08-22 | 1975-08-15 | Inwendige ammoniumzouten van fosfienzuren. |
| IT26470/75A IT1041954B (it) | 1974-08-22 | 1975-08-20 | Sali interni ammonici di acidi fosfinici |
| JP50100238A JPS5143726A (xx) | 1974-08-22 | 1975-08-20 | |
| AT649675A AT332884B (de) | 1974-08-22 | 1975-08-21 | Verfahren zur herstellung neuer innerer ammoniumsalze von phosphinsauren |
| CA234,011A CA1051920A (en) | 1974-08-22 | 1975-08-21 | Inner ammonium salts of phosphinic acids |
| ZA00755366A ZA755366B (en) | 1974-08-22 | 1975-08-21 | Inner ammonium salts of phosphinic acids |
| FR7525875A FR2282431A1 (fr) | 1974-08-22 | 1975-08-21 | Sels d'ammonium internes de l'acide phosphinique |
| GB34977/75A GB1525262A (en) | 1974-08-22 | 1975-08-22 | Zwitterionic compounds of phosphinic acids |
| BE159411A BE832681A (fr) | 1974-08-22 | 1975-08-22 | Sels d'ammonium internes de l'acide phosphinique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2440239A DE2440239A1 (de) | 1974-08-22 | 1974-08-22 | Innere ammoniumsalze von phosphinsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2440239A1 true DE2440239A1 (de) | 1976-03-04 |
Family
ID=5923804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2440239A Withdrawn DE2440239A1 (de) | 1974-08-22 | 1974-08-22 | Innere ammoniumsalze von phosphinsaeuren |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5143726A (xx) |
| AT (1) | AT332884B (xx) |
| BE (1) | BE832681A (xx) |
| CA (1) | CA1051920A (xx) |
| DE (1) | DE2440239A1 (xx) |
| FR (1) | FR2282431A1 (xx) |
| GB (1) | GB1525262A (xx) |
| IT (1) | IT1041954B (xx) |
| NL (1) | NL7509753A (xx) |
| ZA (1) | ZA755366B (xx) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2723137C3 (de) * | 1977-05-23 | 1980-06-26 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Methyl- [2-<2,4,6tribromphenylcarbamoyl-)äthyl-] phosphinsäure |
| US5243062A (en) * | 1984-10-12 | 1993-09-07 | Ciba-Geigy Corporation | Substituted propane-phosphonous acid compounds |
| US5457095A (en) * | 1984-10-12 | 1995-10-10 | Ciba-Geigy Corporation | Substituted propane-phosponous acid compounds |
| US5190933A (en) * | 1987-12-04 | 1993-03-02 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| GB8728483D0 (en) * | 1987-12-04 | 1988-01-13 | Ciba Geigy Ag | Chemical compounds |
| US5300679A (en) * | 1987-12-04 | 1994-04-05 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| US5281747A (en) * | 1989-05-13 | 1994-01-25 | Ciba-Geigy Corporation | Substituted aminoalkylphosphinic acids |
| US5190934A (en) * | 1989-06-03 | 1993-03-02 | Ciba-Geigy Corporation | P-subsituted propane-phosphinic acid compounds |
| IL98502A (en) * | 1990-06-22 | 1998-04-05 | Ciba Geigy Ag | History of Aminoalkene Phosphine Acid, Process for Their Preparation and Pharmaceutical Preparations Containing Them |
| EP0543780A3 (en) * | 1991-11-21 | 1993-09-01 | Ciba-Geigy Ag | Novel aminoalkanephosphinic acids and their salts |
| AU662404B2 (en) * | 1992-05-08 | 1995-08-31 | Novartis Ag | Novel N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
| CN103127876B (zh) * | 2011-11-22 | 2015-01-07 | 中国科学院大连化学物理研究所 | 一种季胺化有机膦表面活性剂及其合成方法 |
-
1974
- 1974-08-22 DE DE2440239A patent/DE2440239A1/de not_active Withdrawn
-
1975
- 1975-08-15 NL NL7509753A patent/NL7509753A/xx not_active Application Discontinuation
- 1975-08-20 JP JP50100238A patent/JPS5143726A/ja active Pending
- 1975-08-20 IT IT26470/75A patent/IT1041954B/it active
- 1975-08-21 ZA ZA00755366A patent/ZA755366B/xx unknown
- 1975-08-21 AT AT649675A patent/AT332884B/de not_active IP Right Cessation
- 1975-08-21 CA CA234,011A patent/CA1051920A/en not_active Expired
- 1975-08-21 FR FR7525875A patent/FR2282431A1/fr active Granted
- 1975-08-22 GB GB34977/75A patent/GB1525262A/en not_active Expired
- 1975-08-22 BE BE159411A patent/BE832681A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1525262A (en) | 1978-09-20 |
| ZA755366B (en) | 1976-08-25 |
| JPS5143726A (xx) | 1976-04-14 |
| NL7509753A (nl) | 1976-02-24 |
| FR2282431A1 (fr) | 1976-03-19 |
| AT332884B (de) | 1976-10-25 |
| ATA649675A (de) | 1976-02-15 |
| BE832681A (fr) | 1976-02-23 |
| FR2282431B1 (xx) | 1978-12-08 |
| IT1041954B (it) | 1980-01-10 |
| CA1051920A (en) | 1979-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |