DE2156810A1 - Photochemisches Verfahren zur Herstellung von Dihalogepenphosphinen - Google Patents
Photochemisches Verfahren zur Herstellung von DihalogepenphosphinenInfo
- Publication number
- DE2156810A1 DE2156810A1 DE19712156810 DE2156810A DE2156810A1 DE 2156810 A1 DE2156810 A1 DE 2156810A1 DE 19712156810 DE19712156810 DE 19712156810 DE 2156810 A DE2156810 A DE 2156810A DE 2156810 A1 DE2156810 A1 DE 2156810A1
- Authority
- DE
- Germany
- Prior art keywords
- phosphorus
- molar ratio
- reaction
- phosphorus halide
- irradiation
- 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 24
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 phosphorus halide Chemical class 0.000 claims description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims description 18
- 239000011574 phosphorus Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 20
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- MJEQIIGWDHUZJW-UHFFFAOYSA-N dichloro(cyclohexyl)phosphane Chemical compound ClP(Cl)C1CCCCC1 MJEQIIGWDHUZJW-UHFFFAOYSA-N 0.000 description 5
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical class ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000009189 diving Effects 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229940094933 n-dodecane Drugs 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000003608 radiolysis reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 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
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 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
- 230000001419 dependent effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- PUDFIJVVIPLMQS-UHFFFAOYSA-N dichloro(2-methylpropyl)phosphane Chemical compound CC(C)CP(Cl)Cl PUDFIJVVIPLMQS-UHFFFAOYSA-N 0.000 description 1
- KGQGBXLQFDXCDB-UHFFFAOYSA-N dichloro(heptyl)phosphane Chemical compound CCCCCCCP(Cl)Cl KGQGBXLQFDXCDB-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NMJASRUOIRRDSX-UHFFFAOYSA-N tert-butyl(dichloro)phosphane Chemical compound CC(C)(C)P(Cl)Cl NMJASRUOIRRDSX-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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/123—Ultraviolet light
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7041139A FR2114129A5 (it) | 1970-11-17 | 1970-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2156810A1 true DE2156810A1 (de) | 1972-05-25 |
Family
ID=9064260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712156810 Pending DE2156810A1 (de) | 1970-11-17 | 1971-11-16 | Photochemisches Verfahren zur Herstellung von Dihalogepenphosphinen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE775336A (it) |
| CH (1) | CH536324A (it) |
| DE (1) | DE2156810A1 (it) |
| FR (1) | FR2114129A5 (it) |
| GB (1) | GB1309214A (it) |
| IT (1) | IT940642B (it) |
| LU (1) | LU64268A1 (it) |
| NL (1) | NL7115813A (it) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1016456A2 (de) * | 1998-12-15 | 2000-07-05 | Aventis Research & Technologies GmbH & Co. KG | Optische Anordnung für kontinuierlich betriebene Photoinitierungen in Strömungsreaktoren, insbesondere für die Photoinitiierung der Umsetzung von Methan und Phosphortrichlorid zu Methyldichlorphosphan |
| AT504301B1 (de) * | 2006-09-20 | 2013-10-15 | Polymer Competence Ct Leoben Gmbh | Verfahren zur modifizierung von kunststoffen sowie damit hergestellte formkörper |
-
1970
- 1970-11-17 FR FR7041139A patent/FR2114129A5/fr not_active Expired
-
1971
- 1971-11-16 BE BE775336A patent/BE775336A/xx unknown
- 1971-11-16 LU LU64268D patent/LU64268A1/xx unknown
- 1971-11-16 GB GB5321471A patent/GB1309214A/en not_active Expired
- 1971-11-16 CH CH1666071A patent/CH536324A/fr not_active IP Right Cessation
- 1971-11-16 DE DE19712156810 patent/DE2156810A1/de active Pending
- 1971-11-17 IT IT3119271A patent/IT940642B/it active
- 1971-11-17 NL NL7115813A patent/NL7115813A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1016456A2 (de) * | 1998-12-15 | 2000-07-05 | Aventis Research & Technologies GmbH & Co. KG | Optische Anordnung für kontinuierlich betriebene Photoinitierungen in Strömungsreaktoren, insbesondere für die Photoinitiierung der Umsetzung von Methan und Phosphortrichlorid zu Methyldichlorphosphan |
| EP1016456A3 (de) * | 1998-12-15 | 2000-10-18 | Aventis Research & Technologies GmbH & Co. KG | Optische Anordnung für kontinuierlich betriebene Photoinitierungen in Strömungsreaktoren, insbesondere für die Photoinitiierung der Umsetzung von Methan und Phosphortrichlorid zu Methyldichlorphosphan |
| AT504301B1 (de) * | 2006-09-20 | 2013-10-15 | Polymer Competence Ct Leoben Gmbh | Verfahren zur modifizierung von kunststoffen sowie damit hergestellte formkörper |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1309214A (en) | 1973-03-07 |
| NL7115813A (it) | 1972-05-19 |
| FR2114129A5 (it) | 1972-06-30 |
| IT940642B (it) | 1973-02-20 |
| CH536324A (fr) | 1973-04-30 |
| BE775336A (fr) | 1972-03-16 |
| LU64268A1 (it) | 1972-06-02 |
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