CN100425588C - 从甲烷经非合成气过程制备醋酸、甲醇和二甲醚的新流程 - Google Patents
从甲烷经非合成气过程制备醋酸、甲醇和二甲醚的新流程 Download PDFInfo
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- CN100425588C CN100425588C CNB2004100228508A CN200410022850A CN100425588C CN 100425588 C CN100425588 C CN 100425588C CN B2004100228508 A CNB2004100228508 A CN B2004100228508A CN 200410022850 A CN200410022850 A CN 200410022850A CN 100425588 C CN100425588 C CN 100425588C
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- reaction
- flow process
- process according
- acetic acid
- methane
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 126
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 121
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 44
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title abstract 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 80
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001301 oxygen Substances 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 229940099204 ritalin Drugs 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052742 iron Inorganic materials 0.000 claims 3
- 229910052759 nickel Inorganic materials 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 229910052707 ruthenium Inorganic materials 0.000 claims 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 2
- 229940107816 ammonium iodide Drugs 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 229910052741 iridium Inorganic materials 0.000 claims 2
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 238000000975 co-precipitation Methods 0.000 claims 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 229910001511 metal iodide Inorganic materials 0.000 claims 1
- 229910052758 niobium Inorganic materials 0.000 claims 1
- 238000005554 pickling Methods 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000003980 solgel method Methods 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 14
- 230000002194 synthesizing effect Effects 0.000 abstract description 12
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract description 6
- 238000005893 bromination reaction Methods 0.000 abstract description 2
- 239000012495 reaction gas Substances 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000003345 natural gas Substances 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
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- HJCMMOODWZOXML-UHFFFAOYSA-N bromo hypobromite Chemical compound BrOBr HJCMMOODWZOXML-UHFFFAOYSA-N 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 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
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 229910017119 AlPO Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 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
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000435 bromine oxide Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 vinyl acetate ester Chemical class 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (12)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100228508A CN100425588C (zh) | 2004-01-17 | 2004-01-17 | 从甲烷经非合成气过程制备醋酸、甲醇和二甲醚的新流程 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2004100228508A CN100425588C (zh) | 2004-01-17 | 2004-01-17 | 从甲烷经非合成气过程制备醋酸、甲醇和二甲醚的新流程 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1640864A CN1640864A (zh) | 2005-07-20 |
CN100425588C true CN100425588C (zh) | 2008-10-15 |
Family
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CNB2004100228508A Expired - Fee Related CN100425588C (zh) | 2004-01-17 | 2004-01-17 | 从甲烷经非合成气过程制备醋酸、甲醇和二甲醚的新流程 |
Country Status (1)
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CN (1) | CN100425588C (zh) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100582064C (zh) * | 2006-03-20 | 2010-01-20 | 微宏科技(湖州)有限公司 | 从甲烷经过非合成气方法合成碳三至碳十三高碳烃的流程 |
CN101284232B (zh) * | 2007-04-13 | 2013-01-16 | 微宏动力***(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 |
CN101723795A (zh) * | 2008-10-13 | 2010-06-09 | 微宏动力***(湖州)有限公司 | 甲烷制备溴甲烷、高碳烃、甲醇和二甲醚的方法 |
CN101723794A (zh) * | 2008-10-13 | 2010-06-09 | 微宏动力***(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 |
RU2490246C2 (ru) * | 2008-10-27 | 2013-08-20 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Окислительное моногалогенирование метана |
CN105709751B (zh) * | 2014-12-04 | 2018-02-09 | 中国石油化工股份有限公司 | 一种溴甲烷制二甲醚催化剂及其制备方法和应用 |
CN105709750B (zh) * | 2014-12-04 | 2018-01-16 | 中国石油化工股份有限公司 | 一种铜柱撑蒙脱石催化剂及其制备方法和应用 |
CN110508300A (zh) * | 2019-08-29 | 2019-11-29 | 华南农业大学 | 沼气全组分转化生物甲醇催化剂NdNiO3/SiC-SiO2-Foam及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5659077A (en) * | 1996-03-22 | 1997-08-19 | Natural Resources Canada | Production of acetic acid from methane |
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 |
US6462243B1 (en) * | 2001-06-20 | 2002-10-08 | Grt, Inc. | Integrated process for synthesizing alcohols and ethers from alkanes |
-
2004
- 2004-01-17 CN CNB2004100228508A patent/CN100425588C/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5659077A (en) * | 1996-03-22 | 1997-08-19 | Natural Resources Canada | Production of acetic acid from methane |
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 |
US6462243B1 (en) * | 2001-06-20 | 2002-10-08 | Grt, Inc. | Integrated process for synthesizing alcohols and ethers from alkanes |
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Publication number | Publication date |
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CN1640864A (zh) | 2005-07-20 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20090306 Address after: Zhejiang province Huzhou City Road sunny industry science and Technology Park building B Patentee after: Microvast Technologies, Ltd. Address before: Mount Yuelu, Changsha, Hunan, Hunan University Patentee before: Hunan University |
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Owner name: SHERCON TECHNOLOGY (HUZHOU) CO., LTD. Free format text: FORMER OWNER: HUNAN UNIVERSITY Effective date: 20090306 |
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Address after: 313000 Zhejiang Province, Huzhou City Road, sunny Industrial Science and Technology Park building B Patentee after: MICROVAST POWER SYSTEMS Co.,Ltd. Address before: 313000 Zhejiang Province, Huzhou City Road, sunny Industrial Science and Technology Park building B Patentee before: Microvast Technologies, Ltd. |
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CP02 | Change in the address of a patent holder |
Address after: 313000 Huzhou economic and Technological Development Zone, Zhejiang, Hung Fung Road, No. 2198 Patentee after: MICROVAST POWER SYSTEMS Co.,Ltd. Address before: 313000 Zhejiang Province, Huzhou City Road, sunny Industrial Science and Technology Park building B Patentee before: MICROVAST POWER SYSTEMS Co.,Ltd. |
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