CN102471189B - 制备低气味正丁烷的方法 - Google Patents
制备低气味正丁烷的方法 Download PDFInfo
- Publication number
- CN102471189B CN102471189B CN201080029592.XA CN201080029592A CN102471189B CN 102471189 B CN102471189 B CN 102471189B CN 201080029592 A CN201080029592 A CN 201080029592A CN 102471189 B CN102471189 B CN 102471189B
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- Prior art keywords
- quality
- mixture
- normal butane
- hydrogenation
- raw mixture
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- 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.)
- Expired - Fee Related
Links
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 38
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 37
- 235000019253 formic acid Nutrition 0.000 claims abstract description 37
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 27
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical class CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 17
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 62
- 238000005984 hydrogenation reaction Methods 0.000 claims description 37
- 238000000605 extraction Methods 0.000 claims description 36
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 238000004821 distillation Methods 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 239000007791 liquid phase Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 238000005194 fractionation Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 4
- 238000004904 shortening Methods 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 27
- 239000012071 phase Substances 0.000 description 23
- 239000003513 alkali Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000008346 aqueous phase Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 239000000306 component Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 230000008676 import Effects 0.000 description 7
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 230000005484 gravity Effects 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000005882 aldol condensation reaction Methods 0.000 description 4
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006668 aldol addition reaction Methods 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/02—Aliphatic saturated hydrocarbons with one to four carbon atoms
- C07C9/10—Aliphatic saturated hydrocarbons with one to four carbon atoms with four carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
实验编号 | 1 | 2 | 3 | 4 | |
单位 | |||||
原料: | |||||
正丁烷/丁烯 | ml/h | 650 | 650 | 650 | 650 |
C4-烃中的HCOOH | ppm | 500 | 500 | 500 | 500 |
CO | ml/h | 500 | 500 | 500 | 500 |
NaOH (25%) | ml/h | 70 | 70 | 70 | 70 |
温度 | °C | 42 | 60 | 70 | 80 |
压力 | bar | 20 | 20 | 20 | 20 |
循环速度 | l/h | 150 | 150 | 150 | 150 |
分析 | |||||
HCOOH | ppm | < 5 ppm | < 5 ppm | < 5 ppm | < 10 ppm |
pH 前 | 13.0 | 13.0 | 13.0 | 13.0 | |
pH 后 | 12.9 | 13.0 | 13.0 | 13.0 | |
C4-烃中的H2O | ppm | 50 | 45 | 55 | 60。 |
Claims (15)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009027406.5 | 2009-07-01 | ||
DE102009027406A DE102009027406A1 (de) | 2009-07-01 | 2009-07-01 | Verfahren zur Herstellung von geruchsarmen n-Butan |
PCT/EP2010/057031 WO2011000633A1 (de) | 2009-07-01 | 2010-05-21 | Verfahren zur herstellung von geruchsarmem n-butan |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102471189A CN102471189A (zh) | 2012-05-23 |
CN102471189B true CN102471189B (zh) | 2015-01-28 |
Family
ID=42313691
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201080029592.XA Expired - Fee Related CN102471189B (zh) | 2009-07-01 | 2010-05-21 | 制备低气味正丁烷的方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US8846994B2 (zh) |
EP (1) | EP2448892B1 (zh) |
JP (1) | JP5661761B2 (zh) |
KR (1) | KR20120099181A (zh) |
CN (1) | CN102471189B (zh) |
DE (1) | DE102009027406A1 (zh) |
ES (1) | ES2429496T3 (zh) |
MY (1) | MY159383A (zh) |
PL (1) | PL2448892T3 (zh) |
SG (1) | SG177429A1 (zh) |
WO (1) | WO2011000633A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2950884B1 (fr) * | 2009-10-01 | 2011-11-11 | Oreal | Utilisation de derives de vanilline comme conservateur, procede de conservation, composes et composition |
DE102010030990A1 (de) | 2010-07-06 | 2012-01-12 | Evonik Oxeno Gmbh | Verfahren zur selektiven Hydrierung von mehrfach ungesättigten Kohlenwasserstoffen in olefinhaltigen Kohlenwasserstoffgemischen |
EP2906572B1 (de) | 2012-10-12 | 2016-11-23 | Evonik Degussa GmbH | Gemische konstitutionsisomerer bisphosphite |
EP3204468B1 (en) * | 2014-10-09 | 2020-07-29 | Basf Se | Process for adsorber regeneration |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6037516A (en) * | 1997-11-20 | 2000-03-14 | Huntsman Ici Chemicals Llc | Method for removal of oxygenate impurities from organic chemical streams |
DE102008002187A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von C5-Aldehydgemischen mit hohem n-Pentanalanteil |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57177090A (en) * | 1981-04-24 | 1982-10-30 | Sumitomo Chem Co Ltd | Hydrogenation |
JPS60202191A (ja) * | 1984-03-26 | 1985-10-12 | Nippon Steel Chem Co Ltd | 軽油の精製法 |
US5122236A (en) * | 1990-05-21 | 1992-06-16 | Smith Jr Lawrence A | Method for removal of dimethyl ether and methanol from c4 hydrocarbon streams |
US5191149A (en) * | 1991-07-12 | 1993-03-02 | Kulkarni Rajendra D | Method of refining liquified petroleum gases into aerosol propellants |
DE10031520A1 (de) | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Hydroformylierung von Olefinen mit 2 bis 8 Kohlenstoffatomen |
DE10062448A1 (de) | 2000-12-14 | 2002-06-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Hydroformylierungsgemischen |
DE10225565A1 (de) | 2002-06-10 | 2003-12-18 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
DE10232868A1 (de) | 2002-07-19 | 2004-02-05 | Oxeno Olefinchemie Gmbh | Feinporiger Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
WO2005058782A1 (en) * | 2003-12-18 | 2005-06-30 | Exxonmobil Chemical Patents Inc. | Improvements in or relating to hydrogenation |
DE102004033410A1 (de) | 2004-02-14 | 2005-09-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Olefinen mit 8 bis 12 Kohlenstoffatomen |
DE102005035816A1 (de) | 2005-07-30 | 2007-02-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Oxo-Aldehyden mit hohen Estergehalten |
DE102005062700A1 (de) * | 2005-12-28 | 2007-07-05 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Buten aus technischen Mischungen von C4-Kohlenwasserstoffen |
US20090023882A1 (en) * | 2006-02-23 | 2009-01-22 | Basf Se | Process for preparation of polyisobutylene whose content of terminal double bonds is more than 50% from an industrial c4 hydrocarbon stream comprising 1-butene, 2-butene and isobutene |
DE102006031964A1 (de) | 2006-07-11 | 2008-01-17 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 3-Methylbut-1-en |
DE102007041380A1 (de) | 2007-08-31 | 2009-03-05 | Evonik Oxeno Gmbh | Hydrierkatalysator und Verfahren zur Herstellung von Alkoholen durch Hydrierung von Carbonylverbindungen |
DE102007061649A1 (de) | 2007-12-20 | 2009-07-02 | Evonik Oxeno Gmbh | Einstufiges kontinuierliches Verfahren zur Hydroformylierung von höheren Olefinen oder Olefingemischen |
DE102009045718A1 (de) | 2009-10-15 | 2011-04-21 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Decanolen durch Hydrierung von Decenalen |
-
2009
- 2009-07-01 DE DE102009027406A patent/DE102009027406A1/de not_active Withdrawn
-
2010
- 2010-05-21 SG SG2011097300A patent/SG177429A1/en unknown
- 2010-05-21 WO PCT/EP2010/057031 patent/WO2011000633A1/de active Application Filing
- 2010-05-21 ES ES10720622T patent/ES2429496T3/es active Active
- 2010-05-21 EP EP10720622.9A patent/EP2448892B1/de active Active
- 2010-05-21 MY MYPI2011006388A patent/MY159383A/en unknown
- 2010-05-21 US US13/381,735 patent/US8846994B2/en not_active Expired - Fee Related
- 2010-05-21 KR KR1020117031614A patent/KR20120099181A/ko not_active Application Discontinuation
- 2010-05-21 CN CN201080029592.XA patent/CN102471189B/zh not_active Expired - Fee Related
- 2010-05-21 PL PL10720622T patent/PL2448892T3/pl unknown
- 2010-05-21 JP JP2012518843A patent/JP5661761B2/ja not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6037516A (en) * | 1997-11-20 | 2000-03-14 | Huntsman Ici Chemicals Llc | Method for removal of oxygenate impurities from organic chemical streams |
DE102008002187A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von C5-Aldehydgemischen mit hohem n-Pentanalanteil |
Non-Patent Citations (1)
Title |
---|
Ni/Al2O3-SiO2催化剂对C4单烯烃加氢的催化性能;徐泽辉等;《燃料化学学报》;20060228;第34卷(第1期);第42-46页 * |
Also Published As
Publication number | Publication date |
---|---|
PL2448892T3 (pl) | 2013-11-29 |
EP2448892B1 (de) | 2013-07-10 |
SG177429A1 (en) | 2012-02-28 |
EP2448892A1 (de) | 2012-05-09 |
CN102471189A (zh) | 2012-05-23 |
US20120136186A1 (en) | 2012-05-31 |
KR20120099181A (ko) | 2012-09-07 |
US8846994B2 (en) | 2014-09-30 |
DE102009027406A1 (de) | 2011-01-05 |
JP2012531474A (ja) | 2012-12-10 |
JP5661761B2 (ja) | 2015-01-28 |
ES2429496T3 (es) | 2013-11-15 |
WO2011000633A1 (de) | 2011-01-06 |
MY159383A (en) | 2016-12-29 |
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