CA2329817A1 - Method for the reduction of iodine compounds from a process stream - Google Patents
Method for the reduction of iodine compounds from a process stream Download PDFInfo
- Publication number
- CA2329817A1 CA2329817A1 CA002329817A CA2329817A CA2329817A1 CA 2329817 A1 CA2329817 A1 CA 2329817A1 CA 002329817 A CA002329817 A CA 002329817A CA 2329817 A CA2329817 A CA 2329817A CA 2329817 A1 CA2329817 A1 CA 2329817A1
- Authority
- CA
- Canada
- Prior art keywords
- salt
- mixture
- iodide
- metal
- metal salt
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000008569 process Effects 0.000 title claims abstract description 8
- 150000002497 iodine compounds Chemical class 0.000 title description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- 150000001351 alkyl iodides Chemical class 0.000 claims abstract description 13
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 10
- 239000011630 iodine Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- -1 carboxylate salt Chemical class 0.000 claims abstract description 9
- 239000011701 zinc Substances 0.000 claims abstract description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052768 actinide Inorganic materials 0.000 claims abstract 3
- 150000001255 actinides Chemical class 0.000 claims abstract 3
- 229910052802 copper Inorganic materials 0.000 claims abstract 3
- 239000010949 copper Substances 0.000 claims abstract 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract 3
- 150000002602 lanthanoids Chemical class 0.000 claims abstract 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract 2
- 229910052729 chemical element Inorganic materials 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 70
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 6
- 229910001505 inorganic iodide Inorganic materials 0.000 abstract 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 32
- 235000011054 acetic acid Nutrition 0.000 description 23
- 229960000583 acetic acid Drugs 0.000 description 23
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 23
- 239000002250 absorbent Substances 0.000 description 22
- 230000002745 absorbent Effects 0.000 description 22
- 239000000243 solution Substances 0.000 description 15
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 14
- 229940023032 activated charcoal Drugs 0.000 description 11
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 10
- 235000011056 potassium acetate Nutrition 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229940022663 acetate Drugs 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 3
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 3
- 230000006315 carbonylation Effects 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 1
- 229910013594 LiOAc Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229910007339 Zn(OAc)2 Inorganic materials 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- ZOAIGCHJWKDIPJ-UHFFFAOYSA-M caesium acetate Chemical group [Cs+].CC([O-])=O ZOAIGCHJWKDIPJ-UHFFFAOYSA-M 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical group [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229940071257 lithium acetate Drugs 0.000 description 1
- 229940097364 magnesium acetate tetrahydrate Drugs 0.000 description 1
- XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical group O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012629 purifying agent Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical group OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17347299P | 1999-12-29 | 1999-12-29 | |
| US60/173,472 | 1999-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2329817A1 true CA2329817A1 (en) | 2001-06-29 |
Family
ID=22632187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002329817A Abandoned CA2329817A1 (en) | 1999-12-29 | 2000-12-28 | Method for the reduction of iodine compounds from a process stream |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20020010363A1 (enExample) |
| EP (1) | EP1114814A3 (enExample) |
| JP (1) | JP2001187342A (enExample) |
| KR (1) | KR20010070379A (enExample) |
| CN (1) | CN1302792A (enExample) |
| CA (1) | CA2329817A1 (enExample) |
| RU (1) | RU2268873C2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1423847E (pt) * | 2001-11-29 | 2005-05-31 | Coding Tech Ab | Reconstrucao de componentes de frequencia elevada |
| JP4409226B2 (ja) * | 2003-07-02 | 2010-02-03 | 日宝化学株式会社 | ヨウ化アルキルの回収方法およびヨウ化アルキル回収装置 |
| US7915470B2 (en) | 2006-09-08 | 2011-03-29 | Board Of Regents, The University Of Texas System | Coupled electrochemical method for reduction of polyols to hydrocarbons |
| CN100581646C (zh) * | 2006-12-28 | 2010-01-20 | 中国科学院化学研究所 | 一种载银高分子衍生碳除碘吸附剂及制法和应用 |
| CN102249190B (zh) * | 2011-07-25 | 2013-03-13 | 国药集团化学试剂有限公司 | 一种氢碘酸的纯化方法 |
| CN103071457B (zh) * | 2013-01-15 | 2014-12-24 | 中国科学院青海盐湖研究所 | 凝胶型碘离子吸附剂、其制备方法及应用 |
| CN103214361B (zh) * | 2013-04-28 | 2015-07-15 | 天津渤海化工有限责任公司天津碱厂 | 一种低负荷下含碘甲醇再生循环利用方法 |
| CN106782504B (zh) * | 2016-12-29 | 2019-01-22 | 百度在线网络技术（北京）有限公司 | 语音识别方法和装置 |
| CN110732352A (zh) * | 2019-09-23 | 2020-01-31 | 江苏大学 | 一种过渡金属离子交换树脂脱碘剂的制备方法 |
| CN110743493A (zh) * | 2019-11-07 | 2020-02-04 | 江苏索普化工股份有限公司 | 一种分子筛脱碘剂的制备方法及分子筛脱碘剂 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791577A (fr) * | 1971-11-19 | 1973-05-17 | Monsanto Co | Purification de courants d'acide carboxylique |
| US4246195A (en) * | 1978-10-06 | 1981-01-20 | Halcon Research And Development Corporation | Purification of carbonylation products |
| DE2901359A1 (de) * | 1979-01-15 | 1980-07-24 | Basf Ag | Verfahren zur entfernung von jod aus organischen verbindungen |
| GB8822661D0 (en) * | 1988-09-27 | 1988-11-02 | Bp Chem Int Ltd | Removal of iodine/iodide impurities |
| GB9022787D0 (en) * | 1990-10-19 | 1990-12-05 | British Petroleum Co Plc | Process |
| US5300685A (en) * | 1991-11-25 | 1994-04-05 | Hoechst Celanese Corporation | Removal of halide impurities from organic liquids |
| KR950013467B1 (ko) * | 1993-03-31 | 1995-11-08 | 포항종합제철주식회사 | 초산중의 요오드 화합물의 제거방법 |
-
2000
- 2000-12-18 EP EP00127663A patent/EP1114814A3/en not_active Withdrawn
- 2000-12-21 US US09/740,822 patent/US20020010363A1/en not_active Abandoned
- 2000-12-27 JP JP2000397943A patent/JP2001187342A/ja not_active Withdrawn
- 2000-12-28 RU RU2000132899/04A patent/RU2268873C2/ru not_active IP Right Cessation
- 2000-12-28 CA CA002329817A patent/CA2329817A1/en not_active Abandoned
- 2000-12-29 KR KR1020000085714A patent/KR20010070379A/ko not_active Ceased
- 2000-12-29 CN CN00137385A patent/CN1302792A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001187342A (ja) | 2001-07-10 |
| EP1114814A2 (en) | 2001-07-11 |
| CN1302792A (zh) | 2001-07-11 |
| US20020010363A1 (en) | 2002-01-24 |
| KR20010070379A (ko) | 2001-07-25 |
| EP1114814A3 (en) | 2003-01-22 |
| RU2268873C2 (ru) | 2006-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |