DE2110769C3 - Perfluoralkyl-phosphorjodide - Google Patents
Perfluoralkyl-phosphorjodideInfo
- Publication number
- DE2110769C3 DE2110769C3 DE19712110769 DE2110769A DE2110769C3 DE 2110769 C3 DE2110769 C3 DE 2110769C3 DE 19712110769 DE19712110769 DE 19712110769 DE 2110769 A DE2110769 A DE 2110769A DE 2110769 C3 DE2110769 C3 DE 2110769C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- perfluoroalkyl
- iodides
- phosphorus
- conversions
- 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
- -1 Perfluoroalkyl phosphoriodides Chemical class 0.000 title claims description 22
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004817 gas chromatography Methods 0.000 claims description 3
- 150000004694 iodide salts Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical class IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 claims description 2
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- BULLJMKUVKYZDJ-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-iodohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I BULLJMKUVKYZDJ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PGRFXXCKHGIFSV-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-iodobutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)I PGRFXXCKHGIFSV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JRJHYWMITKGGTN-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,20,20,21,21,22,22,23,23,24,24-nonatetracontafluoro-24-iodotetracosane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I JRJHYWMITKGGTN-UHFFFAOYSA-N 0.000 description 1
- XEPZXQWMUFPPFO-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,20,20,21,21,22,22-pentatetracontafluoro-22-iododocosane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I XEPZXQWMUFPPFO-UHFFFAOYSA-N 0.000 description 1
- AQDHOJSLSYFQND-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,19,19,20,20-hentetracontafluoro-20-iodoicosane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I AQDHOJSLSYFQND-UHFFFAOYSA-N 0.000 description 1
- LEILRZKFWLKYCT-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16-tritriacontafluoro-16-iodohexadecane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I LEILRZKFWLKYCT-UHFFFAOYSA-N 0.000 description 1
- UDWBMXSQHOHKOI-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10-henicosafluoro-10-iododecane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I UDWBMXSQHOHKOI-UHFFFAOYSA-N 0.000 description 1
- KWXGJTSJUKTDQU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I KWXGJTSJUKTDQU-UHFFFAOYSA-N 0.000 description 1
- UKSMDBFLQBBGPT-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-hexatriacontafluorooctadec-1-ene Chemical group FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UKSMDBFLQBBGPT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BWGUYVSJNOGULH-UHFFFAOYSA-N FC(C(C(C(C(C(F)(F)P(I)I)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F Chemical compound FC(C(C(C(C(C(F)(F)P(I)I)(F)F)(F)F)(F)F)(F)F)(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)F BWGUYVSJNOGULH-UHFFFAOYSA-N 0.000 description 1
- 101710181452 Retinal guanylyl cyclase 1 Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 description 1
- XHTJLMYQJHCUPE-UHFFFAOYSA-N phosphanylphosphonic acid Chemical class OP(O)(P)=O XHTJLMYQJHCUPE-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Lubricants (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712110769 DE2110769C3 (de) | 1971-03-06 | 1971-03-06 | Perfluoralkyl-phosphorjodide |
| NL7202695A NL172747C (nl) | 1971-03-06 | 1972-03-01 | Werkwijze voor het bereiden van als smeerolie-toeslagstoffen toepasbare verbindingen. |
| CH306972A CH564561A5 (enrdf_load_stackoverflow) | 1971-03-06 | 1972-03-02 | |
| CA136,163A CA982143A (en) | 1971-03-06 | 1972-03-03 | Perfluoroalkyl phosphorus iodides |
| JP2162472A JPS5535399B1 (enrdf_load_stackoverflow) | 1971-03-06 | 1972-03-03 | |
| GB999172A GB1363365A (en) | 1971-03-06 | 1972-03-03 | Perfluoroalkyl phosphorus iodides and process for their preparation |
| IT2145572A IT953470B (it) | 1971-03-06 | 1972-03-04 | Perfluoraoalchil fosforoioduri |
| BE780272A BE780272A (fr) | 1971-03-06 | 1972-03-06 | Iodures de perfluoroalkyl-phosphores |
| SU1758809A SU470963A3 (ru) | 1971-03-06 | 1972-03-06 | Способ получени перфторалкилдийодфосфинов и бис(перфторалкил)иодфосфинов |
| FR7207678A FR2128654B1 (enrdf_load_stackoverflow) | 1971-03-06 | 1972-03-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712110769 DE2110769C3 (de) | 1971-03-06 | 1971-03-06 | Perfluoralkyl-phosphorjodide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2110769A1 DE2110769A1 (de) | 1972-09-28 |
| DE2110769B2 DE2110769B2 (de) | 1973-10-04 |
| DE2110769C3 true DE2110769C3 (de) | 1974-05-16 |
Family
ID=5800733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712110769 Expired DE2110769C3 (de) | 1971-03-06 | 1971-03-06 | Perfluoralkyl-phosphorjodide |
Country Status (10)
-
1971
- 1971-03-06 DE DE19712110769 patent/DE2110769C3/de not_active Expired
-
1972
- 1972-03-01 NL NL7202695A patent/NL172747C/xx not_active IP Right Cessation
- 1972-03-02 CH CH306972A patent/CH564561A5/xx not_active IP Right Cessation
- 1972-03-03 JP JP2162472A patent/JPS5535399B1/ja active Pending
- 1972-03-03 GB GB999172A patent/GB1363365A/en not_active Expired
- 1972-03-03 CA CA136,163A patent/CA982143A/en not_active Expired
- 1972-03-04 IT IT2145572A patent/IT953470B/it active
- 1972-03-06 BE BE780272A patent/BE780272A/xx not_active IP Right Cessation
- 1972-03-06 FR FR7207678A patent/FR2128654B1/fr not_active Expired
- 1972-03-06 SU SU1758809A patent/SU470963A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BE780272A (fr) | 1972-09-06 |
| DE2110769B2 (de) | 1973-10-04 |
| NL172747B (nl) | 1983-05-16 |
| NL7202695A (enrdf_load_stackoverflow) | 1972-09-08 |
| DE2110769A1 (de) | 1972-09-28 |
| IT953470B (it) | 1973-08-10 |
| CH564561A5 (enrdf_load_stackoverflow) | 1975-07-31 |
| SU470963A3 (ru) | 1975-05-15 |
| CA982143A (en) | 1976-01-20 |
| FR2128654B1 (enrdf_load_stackoverflow) | 1976-07-09 |
| NL172747C (nl) | 1983-10-17 |
| GB1363365A (en) | 1974-08-14 |
| JPS5535399B1 (enrdf_load_stackoverflow) | 1980-09-12 |
| FR2128654A1 (enrdf_load_stackoverflow) | 1972-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |