JPH08502469A - ヨウ素化された有機化合物からヨウ素を回収する方法 - Google Patents
ヨウ素化された有機化合物からヨウ素を回収する方法Info
- Publication number
- JPH08502469A JPH08502469A JP6510620A JP51062094A JPH08502469A JP H08502469 A JPH08502469 A JP H08502469A JP 6510620 A JP6510620 A JP 6510620A JP 51062094 A JP51062094 A JP 51062094A JP H08502469 A JPH08502469 A JP H08502469A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- iodine
- organic
- catalyst
- filtered
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000011630 iodine Substances 0.000 title claims abstract description 39
- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 39
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000706 filtrate Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000007800 oxidant agent Substances 0.000 claims abstract description 8
- 150000007524 organic acids Chemical class 0.000 claims abstract description 7
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000007530 organic bases Chemical class 0.000 claims abstract description 5
- 238000005831 deiodination reaction Methods 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012452 mother liquor Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLJAKJSGUDBOHG-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I YLJAKJSGUDBOHG-UHFFFAOYSA-N 0.000 description 1
- IPHVGAPABXWWLO-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(I)C=C(I)C(C(O)=O)=C1I IPHVGAPABXWWLO-UHFFFAOYSA-N 0.000 description 1
- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical compound OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GOQCZMZLABPEME-UHFFFAOYSA-N 3,5-diamino-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C(N)=C(I)C(C(O)=O)=C1I GOQCZMZLABPEME-UHFFFAOYSA-N 0.000 description 1
- QMQFFHSJUJDRPG-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C=C(I)C(C(O)=O)=C1I QMQFFHSJUJDRPG-UHFFFAOYSA-N 0.000 description 1
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001089 mineralizing effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000005527 organic iodine compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/13—Iodine; Hydrogen iodide
- C01B7/14—Iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
- C07B35/06—Decomposition, e.g. elimination of halogens, water or hydrogen halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4236724.7 | 1992-10-30 | ||
| DE19924236724 DE4236724A1 (de) | 1992-10-30 | 1992-10-30 | Verfahren zur Rückgewinnung von Jod aus jodierten organischen Verbindungen |
| PCT/EP1993/002822 WO1994010083A1 (de) | 1992-10-30 | 1993-10-13 | Verfahren zur rückgewinnung von jod aus jodierten organischen verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08502469A true JPH08502469A (ja) | 1996-03-19 |
Family
ID=6471762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6510620A Pending JPH08502469A (ja) | 1992-10-30 | 1993-10-13 | ヨウ素化された有機化合物からヨウ素を回収する方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0666830A1 (de) |
| JP (1) | JPH08502469A (de) |
| CA (1) | CA2147373A1 (de) |
| DE (1) | DE4236724A1 (de) |
| WO (1) | WO1994010083A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020522456A (ja) * | 2017-06-07 | 2020-07-30 | ブラッコ・イメージング・ソシエタ・ペル・アチオニBracco Imaging S.P.A. | 水溶液からのヨウ素の回収方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19635531C2 (de) * | 1996-08-20 | 2002-02-28 | Schering Ag | Verfahren zum Abbau von Triiodbenzolderivaten in wäßrigen Medien |
| DE19806001A1 (de) * | 1998-02-16 | 1999-08-19 | Berger Johann | Verfahren zur Dehalogenierung von in Wasser gelösten Halogenkohlenwasserstoffen (HKW) mit Hilfe von vernickeltem Zink |
| CN112919678B (zh) * | 2021-01-29 | 2023-04-18 | 江苏集萃托普索清洁能源研发有限公司 | 醋酸生产废水处理工艺 |
| CN113265703B (zh) * | 2021-04-28 | 2022-03-25 | 中南大学 | 一种金属砷晶体脱碘方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1152493B (it) * | 1982-08-09 | 1986-12-31 | Bracco Ind Chimica Spa | Metodo per il recupero dello iodio da acque madri ed effluenti contenenti iodio organico |
| JP2569104B2 (ja) * | 1988-02-06 | 1997-01-08 | 三井東圧化学株式会社 | 有機沃素化合物を含有する廃液からの沃素回収方法 |
| JP2569111B2 (ja) * | 1988-03-03 | 1997-01-08 | 三井東圧化学株式会社 | 有機沃素化合物を含有する廃液から沃素を回収する方法 |
-
1992
- 1992-10-30 DE DE19924236724 patent/DE4236724A1/de not_active Ceased
-
1993
- 1993-10-13 JP JP6510620A patent/JPH08502469A/ja active Pending
- 1993-10-13 WO PCT/EP1993/002822 patent/WO1994010083A1/de not_active Ceased
- 1993-10-13 EP EP93922560A patent/EP0666830A1/de not_active Withdrawn
- 1993-10-13 CA CA002147373A patent/CA2147373A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020522456A (ja) * | 2017-06-07 | 2020-07-30 | ブラッコ・イメージング・ソシエタ・ペル・アチオニBracco Imaging S.P.A. | 水溶液からのヨウ素の回収方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0666830A1 (de) | 1995-08-16 |
| WO1994010083A1 (de) | 1994-05-11 |
| DE4236724A1 (de) | 1994-05-05 |
| CA2147373A1 (en) | 1994-05-11 |
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