NO300967B1 - Fremstilling av faste perfluoralkylbromider - Google Patents
Fremstilling av faste perfluoralkylbromider Download PDFInfo
- Publication number
- NO300967B1 NO300967B1 NO943302A NO943302A NO300967B1 NO 300967 B1 NO300967 B1 NO 300967B1 NO 943302 A NO943302 A NO 943302A NO 943302 A NO943302 A NO 943302A NO 300967 B1 NO300967 B1 NO 300967B1
- Authority
- NO
- Norway
- Prior art keywords
- bromide
- perfluoroalkyl
- liquid
- iodide
- normal conditions
- Prior art date
Links
- -1 perfluoroalkyl bromides Chemical class 0.000 title claims description 27
- 239000007787 solid Substances 0.000 title claims description 10
- 239000007788 liquid Substances 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 238000005893 bromination reaction Methods 0.000 claims description 11
- WTWWXOGTJWMJHI-UHFFFAOYSA-N perflubron 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)Br WTWWXOGTJWMJHI-UHFFFAOYSA-N 0.000 claims description 11
- 230000031709 bromination Effects 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 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 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229960001217 perflubron Drugs 0.000 claims description 5
- JTYRBFORUCBNHJ-UHFFFAOYSA-N 1-bromo-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)Br JTYRBFORUCBNHJ-UHFFFAOYSA-N 0.000 claims description 3
- JCAULFRGWRHHIG-UHFFFAOYSA-N 1-bromo-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-henicosafluorodecane 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)Br JCAULFRGWRHHIG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001649 bromium compounds Chemical class 0.000 claims description 2
- 239000008240 homogeneous mixture Substances 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003633 blood substitute Substances 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/204—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being a halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9311045A FR2710053B1 (fr) | 1993-09-16 | 1993-09-16 | Fabrication des bromures de perfluoroalkyle solides. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO943302D0 NO943302D0 (no) | 1994-09-07 |
| NO943302L NO943302L (no) | 1995-03-17 |
| NO300967B1 true NO300967B1 (no) | 1997-08-25 |
Family
ID=9450934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO943302A NO300967B1 (no) | 1993-09-16 | 1994-09-07 | Fremstilling av faste perfluoralkylbromider |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5532420A (ko) |
| EP (1) | EP0644170B1 (ko) |
| JP (1) | JP2543669B2 (ko) |
| KR (1) | KR0146024B1 (ko) |
| CN (1) | CN1038743C (ko) |
| AT (1) | ATE185544T1 (ko) |
| AU (1) | AU668834B2 (ko) |
| CA (1) | CA2132029C (ko) |
| DE (1) | DE69421145T2 (ko) |
| FI (1) | FI944285A (ko) |
| FR (1) | FR2710053B1 (ko) |
| HU (1) | HU213042B (ko) |
| IL (1) | IL110642A (ko) |
| NO (1) | NO300967B1 (ko) |
| ZA (1) | ZA947196B (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014110284A1 (en) * | 2013-01-09 | 2014-07-17 | Bacterin International, Inc. | Bone graft substitute containing a temporary contrast agent and a method of generating such and a method of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2797626B2 (ja) * | 1990-04-03 | 1998-09-17 | 旭硝子株式会社 | パーフルオロアルキルブロマイドの製造方法 |
| DE4116361A1 (de) * | 1990-06-23 | 1992-01-02 | Hoechst Ag | Verfahren zur herstellung von perfluoralkylmonobromiden |
| FR2676731A1 (fr) * | 1991-05-21 | 1992-11-27 | Atochem | Synthese de bromures de perfluoroalkyle. |
| FR2677979B1 (fr) * | 1991-06-21 | 1993-09-17 | Atochem | Synthese d'un bromure de perfluoroalkyle par photobromation de l'iodure correspondant. |
| FR2685319B1 (fr) * | 1991-12-20 | 1995-02-24 | Atochem | Synthese du bromure de n.perfluorooctyle. |
-
1993
- 1993-09-16 FR FR9311045A patent/FR2710053B1/fr not_active Expired - Fee Related
-
1994
- 1994-08-12 IL IL11064294A patent/IL110642A/en not_active IP Right Cessation
- 1994-08-30 EP EP94401914A patent/EP0644170B1/fr not_active Expired - Lifetime
- 1994-08-30 AT AT94401914T patent/ATE185544T1/de not_active IP Right Cessation
- 1994-08-30 DE DE69421145T patent/DE69421145T2/de not_active Expired - Fee Related
- 1994-09-01 AU AU71623/94A patent/AU668834B2/en not_active Ceased
- 1994-09-07 NO NO943302A patent/NO300967B1/no unknown
- 1994-09-12 US US08/304,457 patent/US5532420A/en not_active Expired - Lifetime
- 1994-09-14 JP JP6219730A patent/JP2543669B2/ja not_active Expired - Fee Related
- 1994-09-14 CA CA002132029A patent/CA2132029C/fr not_active Expired - Fee Related
- 1994-09-15 HU HU9402645A patent/HU213042B/hu not_active IP Right Cessation
- 1994-09-15 FI FI944285A patent/FI944285A/fi not_active Application Discontinuation
- 1994-09-16 KR KR1019940023735A patent/KR0146024B1/ko not_active IP Right Cessation
- 1994-09-16 ZA ZA947196A patent/ZA947196B/xx unknown
- 1994-09-16 CN CN94116319A patent/CN1038743C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0644170A1 (fr) | 1995-03-22 |
| US5532420A (en) | 1996-07-02 |
| NO943302D0 (no) | 1994-09-07 |
| FI944285A0 (fi) | 1994-09-15 |
| IL110642A0 (en) | 1994-11-11 |
| HUT68266A (en) | 1995-06-28 |
| FR2710053B1 (fr) | 1995-11-03 |
| KR0146024B1 (ko) | 1998-08-17 |
| ZA947196B (en) | 1995-05-11 |
| NO943302L (no) | 1995-03-17 |
| AU668834B2 (en) | 1996-05-16 |
| EP0644170B1 (fr) | 1999-10-13 |
| JP2543669B2 (ja) | 1996-10-16 |
| AU7162394A (en) | 1995-04-13 |
| CA2132029A1 (fr) | 1995-03-17 |
| HU213042B (en) | 1997-01-28 |
| FR2710053A1 (fr) | 1995-03-24 |
| KR950008449A (ko) | 1995-04-17 |
| ATE185544T1 (de) | 1999-10-15 |
| DE69421145D1 (de) | 1999-11-18 |
| FI944285A (fi) | 1995-03-17 |
| CN1038743C (zh) | 1998-06-17 |
| CA2132029C (fr) | 1998-07-14 |
| CN1106782A (zh) | 1995-08-16 |
| JPH07149679A (ja) | 1995-06-13 |
| IL110642A (en) | 1998-08-16 |
| DE69421145T2 (de) | 2000-05-25 |
| HU9402645D0 (en) | 1994-11-28 |
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