CA1328117C - Liquid phase catalytic hydrogenation process - Google Patents
Liquid phase catalytic hydrogenation processInfo
- Publication number
- CA1328117C CA1328117C CA000584688A CA584688A CA1328117C CA 1328117 C CA1328117 C CA 1328117C CA 000584688 A CA000584688 A CA 000584688A CA 584688 A CA584688 A CA 584688A CA 1328117 C CA1328117 C CA 1328117C
- Authority
- CA
- Canada
- Prior art keywords
- hydrogenation
- bed
- hydrogen
- catalyst
- liquid
- 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.)
- Expired - Fee Related
Links
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- 230000008569 process Effects 0.000 title claims abstract description 62
- 239000007791 liquid phase Substances 0.000 title claims abstract description 29
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 251
- 239000003054 catalyst Substances 0.000 claims abstract description 185
- 239000007789 gas Substances 0.000 claims abstract description 141
- 239000001257 hydrogen Substances 0.000 claims abstract description 136
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 136
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- 150000001299 aldehydes Chemical class 0.000 description 80
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- 238000006243 chemical reaction Methods 0.000 description 34
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- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
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- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
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- 238000005192 partition Methods 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
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- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 1
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- 239000013638 trimer Substances 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00026—Controlling or regulating the heat exchange system
- B01J2208/00035—Controlling or regulating the heat exchange system involving measured parameters
- B01J2208/00044—Temperature measurement
- B01J2208/00061—Temperature measurement of the reactants
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00115—Controlling the temperature by indirect heat exchange with heat exchange elements inside the bed of solid particles
- B01J2208/00141—Coils
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00212—Plates; Jackets; Cylinders
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00256—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles in a heat exchanger for the heat exchange medium separate from the reactor
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00477—Controlling the temperature by thermal insulation means
- B01J2208/00495—Controlling the temperature by thermal insulation means using insulating materials or refractories
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/0053—Controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00539—Pressure
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00548—Flow
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/0061—Controlling the level
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Devices And Processes Conducted In The Presence Of Fluids And Solid Particles (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Lock And Its Accessories (AREA)
- Valve-Gear Or Valve Arrangements (AREA)
- Valve Device For Special Equipments (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878728156A GB8728156D0 (en) | 1987-12-02 | 1987-12-02 | Process |
| GB8728156 | 1987-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1328117C true CA1328117C (en) | 1994-03-29 |
Family
ID=10627851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000584688A Expired - Fee Related CA1328117C (en) | 1987-12-02 | 1988-12-01 | Liquid phase catalytic hydrogenation process |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5093535A (en, 2012) |
| EP (2) | EP0393093A1 (en, 2012) |
| JP (1) | JP2675171B2 (en, 2012) |
| KR (1) | KR960004878B1 (en, 2012) |
| CN (1) | CN1024535C (en, 2012) |
| AT (1) | ATE74898T1 (en, 2012) |
| AU (1) | AU2725688A (en, 2012) |
| CA (1) | CA1328117C (en, 2012) |
| DE (1) | DE3870171D1 (en, 2012) |
| ES (1) | ES2032023T3 (en, 2012) |
| GB (1) | GB8728156D0 (en, 2012) |
| IN (1) | IN172818B (en, 2012) |
| MX (1) | MX170124B (en, 2012) |
| WO (1) | WO1989005286A1 (en, 2012) |
| ZA (1) | ZA889062B (en, 2012) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8917862D0 (en) * | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
| US5360920A (en) * | 1992-08-07 | 1994-11-01 | The Procter & Gamble Company | Hydrogenation in a plate heat exchanger |
| WO1994006738A1 (en) * | 1992-09-14 | 1994-03-31 | Unichema Chemie B.V. | Process for the production of alcohols |
| JP2526404B2 (ja) * | 1993-10-15 | 1996-08-21 | 工業技術院長 | 触媒反応方法 |
| US5744655A (en) * | 1996-06-19 | 1998-04-28 | The Dow Chemical Company | Process to make 2,3-dihalopropanols |
| US5877358A (en) * | 1996-09-23 | 1999-03-02 | Exxon Chemical Patents Inc. | Alcohol hydrogenation with intermediate recycle |
| DE19641707A1 (de) | 1996-10-10 | 1998-04-16 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol durch katalytische Hydrierung von 1,4-Butindiol |
| DE19844325A1 (de) | 1998-09-28 | 2000-03-30 | Degussa | Verfahren zur Herstellung von Alkoholen durch katalytische Hydrierung von Aldehyden oder Ketonen |
| FR2789683B1 (fr) | 1999-02-17 | 2002-02-15 | Roquette Freres | Procede continu de preparation d'un ose hydrogene de haute purete par hydrogenation catalytique |
| DE19933348B4 (de) * | 1999-07-16 | 2005-11-17 | Oxeno Olefinchemie Gmbh | Verfahren zur Reduzierung oxidischer Hydrierkontakte |
| US6632414B2 (en) * | 2001-03-30 | 2003-10-14 | Corning Incorporated | Mini-structured catalyst beds for three-phase chemical processing |
| US6716339B2 (en) | 2001-03-30 | 2004-04-06 | Corning Incorporated | Hydrotreating process with monolithic catalyst |
| ES2318049T3 (es) | 2001-09-25 | 2009-05-01 | Exxonmobil Chemical Patents Inc. | Poli(cloruro de vinilo) plastificado. |
| US7279018B2 (en) | 2002-09-06 | 2007-10-09 | Fortum Oyj | Fuel composition for a diesel engine |
| EP1566372B1 (en) * | 2002-11-27 | 2018-01-10 | New Japan Chemical Co., Ltd. | Method of hydrogenation reaction |
| CN1849383B (zh) * | 2003-09-13 | 2010-11-24 | 埃克森美孚化学专利公司 | 用于机动车齿轮的润滑组合物 |
| US7473811B2 (en) * | 2003-11-13 | 2009-01-06 | Neste Oil Oyj | Process for the hydrogenation of olefins |
| US7422904B2 (en) * | 2005-02-04 | 2008-09-09 | Exxonmobil Chemical Patents Inc. | Method of operating a fixed bed reactor under predetermined hydraulic conditions |
| US8022258B2 (en) | 2005-07-05 | 2011-09-20 | Neste Oil Oyj | Process for the manufacture of diesel range hydrocarbons |
| US12203035B2 (en) | 2005-07-05 | 2025-01-21 | Neste Oyj | Process for the manufacture of diesel range hydrocarbons |
| DE102005042185A1 (de) | 2005-09-06 | 2007-03-08 | Basf Ag | Verfahren zur Abtrennung von polymeren Nebenprodukten aus 1,4-Butindiol |
| DE102005042184A1 (de) | 2005-09-06 | 2007-03-08 | Basf Ag | Verfahren zur Abtrennung von polymeren Nebenprodukten aus 1,4-Butindiol |
| US7649099B2 (en) * | 2006-01-26 | 2010-01-19 | Battelle Memorial Institute | Method of forming a dianhydrosugar alcohol |
| US7615652B2 (en) * | 2006-01-26 | 2009-11-10 | Battelle Memorial Institute | Two-stage dehydration of sugars |
| US7772412B2 (en) * | 2006-01-26 | 2010-08-10 | Battelle Memorial Institute | Methods for dehydration of sugars and sugar alcohols |
| US7728156B2 (en) * | 2006-01-26 | 2010-06-01 | Battelle Memorial Institute | Method of performing sugar dehydration and catalyst treatment |
| CN101495428B (zh) * | 2006-07-25 | 2012-12-12 | 巴斯夫欧洲公司 | 含溶剂的氢化产物混合物的后处理方法 |
| US7759531B2 (en) | 2007-02-15 | 2010-07-20 | Basf Aktiengesellschaft | Process for preparing 1,4-butanediol |
| DE102007011483A1 (de) * | 2007-03-07 | 2008-09-18 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin |
| WO2009009322A1 (en) * | 2007-07-06 | 2009-01-15 | Best Energies, Inc. | Integrated facility for producing alcohol using homoacidogenic fermentation |
| US7811447B2 (en) * | 2007-08-01 | 2010-10-12 | Uop Llc | Method of transferring particles from one pressure zone to another pressure zone |
| US8003834B2 (en) * | 2007-09-20 | 2011-08-23 | Uop Llc | Integrated process for oil extraction and production of diesel fuel from biorenewable feedstocks |
| US8575409B2 (en) | 2007-12-20 | 2013-11-05 | Syntroleum Corporation | Method for the removal of phosphorus |
| US20090300971A1 (en) | 2008-06-04 | 2009-12-10 | Ramin Abhari | Biorenewable naphtha |
| US8581013B2 (en) | 2008-06-04 | 2013-11-12 | Syntroleum Corporation | Biorenewable naphtha composition and methods of making same |
| US7982079B2 (en) * | 2008-09-11 | 2011-07-19 | Uop Llc | Integrated process for production of diesel fuel from renewable feedstocks and ethanol denaturizing |
| US8231804B2 (en) | 2008-12-10 | 2012-07-31 | Syntroleum Corporation | Even carbon number paraffin composition and method of manufacturing same |
| CN101787305B (zh) * | 2009-01-23 | 2013-03-20 | 中国石油化工股份有限公司 | 一种液相循环加氢处理方法和反应系统 |
| WO2011115695A1 (en) | 2010-03-15 | 2011-09-22 | Exxonmobil Chemical Patents Inc. | Processes for the production of alcohols |
| US8394900B2 (en) | 2010-03-18 | 2013-03-12 | Syntroleum Corporation | Profitable method for carbon capture and storage |
| EP2489720A1 (en) | 2011-02-15 | 2012-08-22 | Neste Oil Oyj | Renewable oil with low iron content and its use in hydrotreatment process |
| NL2008611C2 (nl) * | 2012-04-05 | 2013-10-09 | Mooij Agro B V | Inrichting voor het aan een gasstroom onderwerpen van producten, bijvoorbeeld ten behoeve van een droog- of vries-procédé. |
| CN103506125A (zh) * | 2012-06-21 | 2014-01-15 | 中国石油化工股份有限公司 | 用于丙醛气相加氢制丙醇的催化剂及其制备方法 |
| CN103773471B (zh) * | 2012-10-24 | 2015-08-12 | 中国石油化工股份有限公司 | 一种气相、液相联合加氢工艺方法 |
| CN103773475B (zh) * | 2012-10-24 | 2015-09-02 | 中国石油化工股份有限公司 | 一种气相、液相组合加氢工艺方法 |
| HUE030188T2 (en) * | 2013-01-22 | 2017-04-28 | Covestro Deutschland Ag | Process for the preparation of aromatic amines |
| CN103965953B (zh) * | 2013-01-30 | 2015-07-22 | 中国石油天然气股份有限公司 | 一种馏分油两相加氢反应器和加氢工艺方法 |
| US9328303B2 (en) | 2013-03-13 | 2016-05-03 | Reg Synthetic Fuels, Llc | Reducing pressure drop buildup in bio-oil hydroprocessing reactors |
| US8969259B2 (en) | 2013-04-05 | 2015-03-03 | Reg Synthetic Fuels, Llc | Bio-based synthetic fluids |
| CN105555752A (zh) * | 2013-09-13 | 2016-05-04 | 因温斯特技术公司 | 使二腈氢化以便制备二胺 |
| CN104557456A (zh) * | 2013-10-22 | 2015-04-29 | 中国石油化工股份有限公司 | 一种丁醛液相加氢生成丁醇的方法 |
| CN103566837B (zh) * | 2013-11-13 | 2015-09-30 | 山西大学 | 一种适用于加氢放热反应的外循环反应装置 |
| WO2015120250A1 (en) * | 2014-02-07 | 2015-08-13 | E. I. Du Pont De Nemours And Company | Integrated process for the production of z-1,1,1,4,4,4-hexafluoro-2-butene |
| WO2015128202A1 (en) * | 2014-02-25 | 2015-09-03 | Biochemtex S.P.A. | Continuous process for producing an ethylene glycol stream |
| KR101612099B1 (ko) * | 2014-06-25 | 2016-04-14 | (주)테크윈 | 전기분해장치 |
| KR101600037B1 (ko) * | 2014-06-26 | 2016-03-07 | (주)테크윈 | 선박평형수 처리시스템 |
| DE102014223427A1 (de) | 2014-11-17 | 2016-05-19 | Hydrogenious Technologies Gmbh | Verfahren und Anlage zum Erzeugen und Speichern von Wasserstoff |
| CN104492445A (zh) * | 2014-12-18 | 2015-04-08 | 复旦大学 | 一种用于草酸二甲酯气相催化加氢合成乙二醇及乙醇酸甲酯的催化剂及其制备方法 |
| MX369759B (es) | 2015-01-19 | 2019-11-20 | Evonik Operations Gmbh | Preparación combinada de buteno y octeno a partir de eteno. |
| MY194991A (en) * | 2015-06-30 | 2022-12-29 | Takeda Pharmaceuticals Co | Method for producing pyrrole compound |
| KR102743230B1 (ko) | 2015-11-10 | 2024-12-17 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 알데하이드를 생산하는 방법 |
| WO2017139543A1 (en) | 2016-02-11 | 2017-08-17 | Dow Technology Investments Llc | Processes for converting olefins to alcohols, ethers, or combinations thereof |
| WO2017221261A1 (en) * | 2016-06-23 | 2017-12-28 | Natco Pharma Limited | Process for the preparation of pomalidomide and its purification |
| WO2018041754A1 (en) * | 2016-08-30 | 2018-03-08 | Plastic Omnium Advanced Innovation And Research | System and method for increasing the urea concentration of an aqueous solution on-board a vehicle |
| EP3658272A1 (de) * | 2017-07-28 | 2020-06-03 | HTE GmbH The High Throughput Experimentation Company | Vorrichtung und verfahren zur katalytischen umsetzung von chemischen stoffen bei verweilzeiten im bereich von 0,1 - 10 sekunden |
| US20210284962A1 (en) * | 2018-06-21 | 2021-09-16 | The Regents Of The University Of California | Generation of a population of hindbrain cells and hindbrain-like organoids from pluripotent stem cells |
| US11772082B1 (en) | 2018-06-21 | 2023-10-03 | Avn Corporation | Catalyst supports—composition and process of manufacture |
| CN109225073B (zh) * | 2018-09-17 | 2021-01-15 | 清华大学 | 一种微填充床内加氢反应装置及其进行加氢反应的方法 |
| CN111099965B (zh) * | 2018-10-25 | 2024-03-12 | 中国石油化工股份有限公司 | 一种1,5-戊二醇的液相加氢精制方法 |
| CN109908843B (zh) * | 2019-04-23 | 2019-12-31 | 宁波巨化新材料有限公司 | 丙醛加氢反应器 |
| CN112920015B (zh) * | 2019-12-06 | 2025-02-21 | 陶氏技术投资有限责任公司 | 用于精炼由醛的氢化衍生的醇的方法 |
| CN114929660A (zh) | 2019-12-19 | 2022-08-19 | 陶氏技术投资有限责任公司 | 用于制备异戊二烯和包含至少六个碳原子的单烯烃的方法 |
| KR102322998B1 (ko) * | 2019-12-19 | 2021-11-10 | 한국과학기술연구원 | 액상유기수소운반체를 이용한 고순도 수소 정제/저장 장치 및 수소 정제/저장 방법 |
| WO2022066160A1 (en) * | 2020-09-24 | 2022-03-31 | Iowa Corn Promotion Board | Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst |
| US11319269B2 (en) | 2020-09-24 | 2022-05-03 | Iowa Corn Promotion Board | Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst |
| US11884614B2 (en) | 2022-05-26 | 2024-01-30 | Chevron Phillips Chemical Company Lp | Normal alpha olefin synthesis using decarbonylative olefination |
| WO2024026285A1 (en) | 2022-07-27 | 2024-02-01 | Chevron Phillips Chemical Company Lp | SYNTHESIS OF n-HEPTANE FROM OLEFINS AND RELATED PRODUCTION SYSTEMS |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1002372A (en) * | 1961-04-25 | 1965-08-25 | Chisso Corp | Process for continuously hydrogenating higher aldehydes in liquid phase |
| BE754868A (fr) * | 1969-08-16 | 1971-02-15 | Basf Ag | Procede pour la mise en oeuvre de reactions exothermiques entreun gaz et un liquide |
| DE2040501C3 (de) * | 1970-08-14 | 1984-01-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Durchführung von exothermen Reaktionen zwischen einem Gas und einer Flüssigkeit |
| DE2257673B1 (de) * | 1972-11-24 | 1974-03-28 | Verfahren zur herstellung von aliphatischen alkoholen | |
| JPS5812053A (ja) * | 1981-07-15 | 1983-01-24 | Nec Corp | 情報処理装置 |
| US4451677A (en) * | 1981-08-20 | 1984-05-29 | Davy Mckee (London) Limited | Multistage aldehyde hydrogenation |
| US4510092A (en) * | 1982-03-19 | 1985-04-09 | Uop Inc. | Continuous reduction of edible oils |
| US4626604A (en) * | 1985-09-11 | 1986-12-02 | Davy Mckee (London) Limited | Hydrogenation process |
| GB8613354D0 (en) * | 1986-06-03 | 1986-07-09 | Davy Mckee Ltd | Process |
| GB8702654D0 (en) * | 1987-02-06 | 1987-03-11 | Davy Mckee Ltd | Process |
-
1987
- 1987-12-02 GB GB878728156A patent/GB8728156D0/en active Pending
-
1988
- 1988-11-25 KR KR1019890701448A patent/KR960004878B1/ko not_active Expired - Lifetime
- 1988-11-25 US US07/476,453 patent/US5093535A/en not_active Expired - Lifetime
- 1988-11-25 ES ES198888311188T patent/ES2032023T3/es not_active Expired - Lifetime
- 1988-11-25 AU AU27256/88A patent/AU2725688A/en not_active Abandoned
- 1988-11-25 EP EP88910086A patent/EP0393093A1/en active Pending
- 1988-11-25 AT AT88311188T patent/ATE74898T1/de not_active IP Right Cessation
- 1988-11-25 DE DE8888311188T patent/DE3870171D1/de not_active Expired - Lifetime
- 1988-11-25 JP JP1505574A patent/JP2675171B2/ja not_active Expired - Fee Related
- 1988-11-25 EP EP88311188A patent/EP0319208B1/en not_active Expired - Lifetime
- 1988-11-25 WO PCT/GB1988/001027 patent/WO1989005286A1/en not_active Application Discontinuation
- 1988-11-30 IN IN853MA1988 patent/IN172818B/en unknown
- 1988-11-30 MX MX013998A patent/MX170124B/es unknown
- 1988-12-01 CA CA000584688A patent/CA1328117C/en not_active Expired - Fee Related
- 1988-12-02 ZA ZA889062A patent/ZA889062B/xx unknown
- 1988-12-02 CN CN88108327A patent/CN1024535C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0319208B1 (en) | 1992-04-15 |
| JPH03501483A (ja) | 1991-04-04 |
| KR900700422A (ko) | 1990-08-13 |
| EP0393093A1 (en) | 1990-10-24 |
| US5093535A (en) | 1992-03-03 |
| WO1989005286A1 (en) | 1989-06-15 |
| ATE74898T1 (de) | 1992-05-15 |
| EP0319208A1 (en) | 1989-06-07 |
| CN1024535C (zh) | 1994-05-18 |
| MX170124B (es) | 1993-08-09 |
| IN172818B (en, 2012) | 1993-12-04 |
| JP2675171B2 (ja) | 1997-11-12 |
| AU2725688A (en) | 1989-07-05 |
| DE3870171D1 (de) | 1992-05-21 |
| GB8728156D0 (en) | 1988-01-06 |
| KR960004878B1 (ko) | 1996-04-16 |
| CN1033377A (zh) | 1989-06-14 |
| ZA889062B (en) | 1989-08-30 |
| ES2032023T3 (es) | 1993-01-01 |
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