CN1724503A - 从甲烷合成乙酰溴、醋酸、醋酸酯的新流程 - Google Patents
从甲烷合成乙酰溴、醋酸、醋酸酯的新流程 Download PDFInfo
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- CN1724503A CN1724503A CN 200510031734 CN200510031734A CN1724503A CN 1724503 A CN1724503 A CN 1724503A CN 200510031734 CN200510031734 CN 200510031734 CN 200510031734 A CN200510031734 A CN 200510031734A CN 1724503 A CN1724503 A CN 1724503A
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- CN
- China
- Prior art keywords
- methane
- reaction
- bromide
- hbr
- acetyl bromide
- 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.)
- Granted
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 92
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 46
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 26
- 230000002194 synthesizing effect Effects 0.000 title claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 235000019439 ethyl acetate Nutrition 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 239000012429 reaction media Substances 0.000 claims abstract description 7
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims description 10
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 8
- ZMVAWNCSXGFEDX-UHFFFAOYSA-N methane hydrobromide Chemical compound Br.C[H] ZMVAWNCSXGFEDX-UHFFFAOYSA-N 0.000 claims 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052693 Europium Inorganic materials 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052688 Gadolinium Inorganic materials 0.000 claims 1
- 229910052779 Neodymium Inorganic materials 0.000 claims 1
- 229910052777 Praseodymium Inorganic materials 0.000 claims 1
- 229910052772 Samarium Inorganic materials 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 229910052787 antimony Inorganic materials 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 229910052793 cadmium Inorganic materials 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- 229910052745 lead Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052758 niobium Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052755 nonmetal Inorganic materials 0.000 claims 1
- 150000007524 organic acids Chemical group 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 229910052712 strontium Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229910052714 tellurium Inorganic materials 0.000 claims 1
- 229910052716 thallium Inorganic materials 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010948 rhodium Substances 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 3
- 238000005810 carbonylation reaction Methods 0.000 abstract description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 15
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 230000009466 transformation Effects 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004159 Potassium persulphate Substances 0.000 description 2
- 229910019891 RuCl3 Inorganic materials 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 235000019394 potassium persulphate Nutrition 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910021581 Cobalt(III) chloride Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
例 | 压力(atm) | 时间(小时) | 温度(℃) | 转化率(%) |
1234 | 26262626 | 4444 | 100120140150 | 41.5068.0081.20100.00 |
例 | 压力(atm) | 时间(小时) | 温度(℃) | 转化率(%) |
5674 | 17202326 | 4444 | 150150150150 | 43.9078.2091.90100.00 |
例 | 压力(atm) | 时间(小时) | 温度(℃) | 转化率(%) |
891011124 | 262626262626 | 14/35/3234 | 150150150150150150 | 7.2022.9038.5064.6091.60100.00 |
例 | 催化剂(12mg) | KI(mg) | PPh3(mg) | 时间(小时) | 转化率(%) |
41312118141516171819202122232425 | RhCl3RuCl3RhCl3RhCl3RhCl3RhCl3RuCl3RhCl3RhCl3RhCl3RhCl3RhCl3RhCl3RhCl3RhCl3RhCl3RhCl3 | 11011011011011000000000005050 | 0000002020202040608060602060 | 44321443211111.5211 | 100.0014.5091.6064.607.2025.0020.80100.0094.0025.9060.4065.3027.4082.60100.0031.8052.20 |
Claims (10)
Priority Applications (1)
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CNB2005100317347A CN100457706C (zh) | 2005-06-22 | 2005-06-22 | 从甲烷合成乙酰溴、醋酸、醋酸酯的新流程 |
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CNB2005100317347A CN100457706C (zh) | 2005-06-22 | 2005-06-22 | 从甲烷合成乙酰溴、醋酸、醋酸酯的新流程 |
Publications (2)
Publication Number | Publication Date |
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CN1724503A true CN1724503A (zh) | 2006-01-25 |
CN100457706C CN100457706C (zh) | 2009-02-04 |
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CNB2005100317347A Expired - Fee Related CN100457706C (zh) | 2005-06-22 | 2005-06-22 | 从甲烷合成乙酰溴、醋酸、醋酸酯的新流程 |
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Country | Link |
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CN (1) | CN100457706C (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010043162A1 (zh) * | 2008-10-13 | 2010-04-22 | 微宏动力系统(湖州)有限公司 | 甲烷制备溴甲烷、乙酰溴、醋酸和醋酸酯的方法 |
CN102631943A (zh) * | 2012-03-21 | 2012-08-15 | 中国科学院大连化学物理研究所 | 一种用于甲烷溴氧化制备溴代甲烷的铁磷基催化剂和制备方法及其应用 |
CN101284232B (zh) * | 2007-04-13 | 2013-01-16 | 微宏动力系统(湖州)有限公司 | 甲烷溴氧化制溴甲烷及其转化制碳氢化合物的催化剂 |
CN101723820B (zh) * | 2008-10-10 | 2013-07-24 | 中国科学院大连化学物理研究所 | 一种由氯甲烷羰基化制备乙酸的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6452058B1 (en) * | 2001-05-21 | 2002-09-17 | Dow Global Technologies Inc. | Oxidative halogenation of C1 hydrocarbons to halogenated C1 hydrocarbons and integrated processes related thereto |
-
2005
- 2005-06-22 CN CNB2005100317347A patent/CN100457706C/zh not_active Expired - Fee Related
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101284232B (zh) * | 2007-04-13 | 2013-01-16 | 微宏动力系统(湖州)有限公司 | 甲烷溴氧化制溴甲烷及其转化制碳氢化合物的催化剂 |
CN101723820B (zh) * | 2008-10-10 | 2013-07-24 | 中国科学院大连化学物理研究所 | 一种由氯甲烷羰基化制备乙酸的方法 |
WO2010043162A1 (zh) * | 2008-10-13 | 2010-04-22 | 微宏动力系统(湖州)有限公司 | 甲烷制备溴甲烷、乙酰溴、醋酸和醋酸酯的方法 |
CN102631943A (zh) * | 2012-03-21 | 2012-08-15 | 中国科学院大连化学物理研究所 | 一种用于甲烷溴氧化制备溴代甲烷的铁磷基催化剂和制备方法及其应用 |
CN102631943B (zh) * | 2012-03-21 | 2016-12-14 | 中国科学院大连化学物理研究所 | 一种用于甲烷溴氧化制备溴代甲烷的铁磷基催化剂和制备方法及其应用 |
Also Published As
Publication number | Publication date |
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CN100457706C (zh) | 2009-02-04 |
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