WO2012015340A1 - One-step method for butadiene production - Google Patents
One-step method for butadiene production Download PDFInfo
- Publication number
- WO2012015340A1 WO2012015340A1 PCT/RU2011/000565 RU2011000565W WO2012015340A1 WO 2012015340 A1 WO2012015340 A1 WO 2012015340A1 RU 2011000565 W RU2011000565 W RU 2011000565W WO 2012015340 A1 WO2012015340 A1 WO 2012015340A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethanol
- catalyst
- butadiene
- differs
- acetaldehyde
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/16—Alkadienes with four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/16—Alkadienes with four carbon atoms
- C07C11/167—1, 3-Butadiene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2072—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/48—Silver or gold
- C07C2523/50—Silver
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/48—Silver or gold
- C07C2523/52—Gold
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/56—Platinum group metals
- C07C2523/63—Platinum group metals with rare earths or actinides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/56—Platinum group metals
- C07C2523/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tatalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/56—Platinum group metals
- C07C2523/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tatalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/644—Arsenic, antimony or bismuth
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/72—Copper
Definitions
- This invention relates to the gas-phase method of butadiene production, particularly, to formation of butadiene from ethanol or from the mixture of ethanol and acetaldehyde.
- butadiene is essentially used as a monomer in the production of synthetic rubbers, such as butadiene rubber, butadiene-nitrile rubber, butadiene-styrene rubber etc.
- butadiene is obtained by catalytic dehydrogenation of n-butane and butylenes contained in refining and casing-head gases; this process is carried out in one or two steps.
- butadiene is extracted from the products of oil pyrolysis. Because of the uplift in oil prices, alternative methods of obtaining butadiene are of major interest.
- the closest analog of the method proposed is the one, which includes ethanol conversion on the catalyst, which contains magnesium oxide (US 2,374,433 1945).
- the aim of this invention is the development of one-step process, which allows to synthesize butadiene in milder conditions with high yield and high stability of catalyst activity in time.
- the catalyst in which oxides, chosen from the group of magnesium, titanium, zirconium or tantalum, are modified with alkali metals and/or cerium, tin or antimony oxides.
- process is carried out under gas-phase conditions at 200-400°C, under atmospheric pressure, with weight hourly space velocity (WHSV) in the range of 0.1 - 15 g/(g*h).
- WHSV weight hourly space velocity
- weight ratio of acetaldehyde to ethanol in mixture is (1-3): 10, respectively.
- the process is carried out under the conditions of continuous flow in the fixed bed reactor.
- the technical result of method realization as indicated in item 1 is high yield and selectivity of butadiene formation at high stability of catalytic activity in time.
- the result obtained is due to considerable decrease of highly active acetaldehyde content in the gas phase, as it is formed directly on the surface of the catalyst, which contains a metal with dehydrogenation function. This results in the decrease of the rate of deep condensation accompanied by formation of by-products and coke.
- the proposed method of butadiene production comprises in general:
- the catalyst pre-treatment includes heating in inert gas (nitrogen) flow up to 500°C during 1 hour and calcination at this temperature during 30 minutes, then reactor is cooled down to the reaction temperature, the catalyst is reduced in hydrogen flow during 30 minutes and then the flow is switched to inert gas. Ethanol and acetaldehyde are fed into the continuous flow fixed bed reactor. At the reactor outlet the products obtained are divided in liquid and gas products. The products composition is analyzed by chromatographic method.
- inert gas nitrogen
- Catalyst which composition is lAg-10ZrO 2 -500SiO 2 , and which has silica as a support, is placed in the continuous flow reactor, purged with nitrogen at 500°C during 1 hour, then the temperature is decreased to 325°C and the catalyst is blown off with hydrogen during 30 minutes. Then it is switched to nitrogen flow (lOml/min) and ethanol is supplied at a rate of 1.2 g/h. The reaction is carried out during 3 hours. The conversion of ethanol at the reactor outlet is 34%, the yield of butadiene per converted ethanol is 72%.
- Example 1 The process is carried out as in Example 1. The difference is that the measurement of process parameters is carried out in 45 hours after the beginning of the reaction. The results are presented in Table 1.
- Example 1 The process is carried out as in Example 1. The difference is that the catalyst used is magnesium oxide (as in the prototype US 2,374,433), deposited on silica gel. The results are presented in Table 1.
- Example 1 The process is carried out as in Example 1. The difference is that the catalyst used is based on zirconium oxide, deposited on silica gel (analog - US 2,436,125) (The catalyst is obtained by silica gel impregnation with zirconile nitrate). The results are presented in Table 1.
- Example 1 The process is carried out as in Example 1. The difference is that the catalyst contains copper instead of silver, and process is carried out with the addition of acetaldehyde with acetaldehyde/ethanol ratio 1 :10. The results are presented in Table 1.
- Example 6 The process is carried out as in Example 6. The difference is that the catalyst contains gold instead of copper. The results are presented in Table 1.
- Example 1 The process is carried out as in Example 1. The difference is that magnesium oxide is used instead of zirconium oxide, and the process is carried out with the addition of acetaldehyde with acetaldehyde/ethanol ratio 1 :10. The results are presented in Table 1.
- Example 8 The process is carried out as in Example 8. The difference is that titanium oxide is used instead of magnesium oxide. The results are presented in Table 1.
- Example 8 The process is carried out as in Example 8. The difference is that tantalum oxide is used instead of magnesium oxide. The results are presented in Table 1.
- Example 8 The process is carried out as in Example 8. The difference is that niobium oxide is used instead of magnesium oxide. The results are presented in Table 1.
- Example 13 The process is carried out as in Example 1. The difference is that the catalyst contains tin oxide in addition
- the composition of the used catalyst is lAg-10ZrO 2 -3SnO 2 -500SiO 2 .
- the process is carried out with the addition of acetaldehyde with acetaldehyde/ethanol ratio 1 :10. The results are presented in Table 1.
- Example 13 The results are presented in Table 1.
- Example 12 The process is carried out as in Example 12. The difference is that antimony oxide is added instead of tin oxide. The results are presented in Table 1.
- Example 12 The process is carried out as in Example 12. The difference is that catalyst contains cerium oxide instead of tin oxide. The results are presented in Table 1.
- Example 1 The process is carried out as in Example 1. The difference is that the composition of the used catalyst is lAg-10ZrO 2 -3Na 2 O-500SiO 2 . The process is carried out with the addition of acetaldehyde with acetaldehyde/ethanol ratio 1 :10. The results are presented in Table 1.
- Examples 12-15 illustrate a possibility to use in the butadiene process solid catalysts with modifying additives announced.
- Example 14 The process is carried out as in Example 14. The difference is that aluminum oxide is used instead of silica as a support. The results are presented in Table 1.
- Example 14 The process is carried out as in Example 14. The difference is that aluminosilicate is used instead of silica gel as a supporter. The results are presented in Table 1.
- Example 14 The process is carried out as in Example 14. The difference is that the catalyst is used without support. The results are presented in Table 1.
- Example 14 The process is carried out as in Example 14. The difference is that the reaction temperature is 200°C. The results are presented in Table 1.
- Example 14 The process is carried out as in Example 14. The difference is that the reaction temperature is 400°C. The results are presented in Table 1.
- Example 23 The process is carried out as in Example 14. The difference is that weight hourly space velocity is 0,1 g/g-h. The results are presented in Table 1. Example 23.
- Example 14 The process is carried out as in Example 14. The difference is that the weight hourly space velocity is 15 g/g-h. The results are presented in Table 1.
- Examples 19-23 illustrate a possibility to realize the method of butadiene production in a broad range of process parameters' variation.
- the invention can be used in chemical industry, in particular for manufacture of butadiene which can be further used in production of synthetic rubbers, such as butadiene rubber, butadiene-nitrile rubber, butadiene-styrene rubber etc.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
UAA201302090A UA104257C2 (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
EP11776035.5A EP2598465B1 (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
AU2011283229A AU2011283229B2 (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
KR1020137004644A KR101904163B1 (en) | 2010-07-29 | 2011-07-27 | Onestep method for butadiene production |
BR112013002225A BR112013002225A2 (en) | 2010-07-29 | 2011-07-27 | "one-step method for butadiene production" |
CA2804371A CA2804371C (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
CN201180037102.5A CN103038196B (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
MX2013000974A MX2013000974A (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production. |
US13/812,310 US8921635B2 (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
JP2013521736A JP5864572B2 (en) | 2010-07-29 | 2011-07-27 | One-step process for producing butadiene |
ZA2013/01531A ZA201301531B (en) | 2010-07-29 | 2013-02-28 | One-step method for butadiene production |
HK13111368.6A HK1183860A1 (en) | 2010-07-29 | 2013-10-09 | One-step method for butadiene production |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU2010131711 | 2010-07-29 | ||
RU2010131711/04A RU2440962C1 (en) | 2010-07-29 | 2010-07-29 | Single-step method of producing butadiene |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012015340A1 true WO2012015340A1 (en) | 2012-02-02 |
Family
ID=44872577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/RU2011/000565 WO2012015340A1 (en) | 2010-07-29 | 2011-07-27 | One-step method for butadiene production |
Country Status (17)
Country | Link |
---|---|
US (1) | US8921635B2 (en) |
EP (1) | EP2598465B1 (en) |
JP (1) | JP5864572B2 (en) |
KR (1) | KR101904163B1 (en) |
CN (1) | CN103038196B (en) |
AU (1) | AU2011283229B2 (en) |
BR (1) | BR112013002225A2 (en) |
CA (1) | CA2804371C (en) |
HK (1) | HK1183860A1 (en) |
MX (1) | MX2013000974A (en) |
MY (1) | MY162490A (en) |
PE (1) | PE20131061A1 (en) |
PL (1) | PL2598465T3 (en) |
RU (1) | RU2440962C1 (en) |
UA (1) | UA104257C2 (en) |
WO (1) | WO2012015340A1 (en) |
ZA (1) | ZA201301531B (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2712673A1 (en) | 2012-09-28 | 2014-04-02 | LANXESS Deutschland GmbH | Method for manufacturing 1,3-butadiene |
WO2014061917A1 (en) * | 2012-10-19 | 2014-04-24 | 한국화학연구원 | Regular mesoporous silica-based catalyst for preparing 1,3-butadiene from ethanol, and method for preparing 1,3-butadiene using same |
RU2514425C1 (en) * | 2012-11-16 | 2014-04-27 | Открытое акционерное общество Научно-исследовательский институт "Ярсинтез" (ОАО НИИ "Ярсинтез") | Catalyst for producing butadiene by converting ethanol |
KR101440002B1 (en) * | 2012-10-12 | 2014-09-12 | 한국화학연구원 | Tantala-based complex metal oxide supported on silica-based catalysts for the production of 1,3-butadiene from ethanol and production method of 1,3-butadiene using thereof |
WO2014180778A1 (en) * | 2013-05-07 | 2014-11-13 | Synthos S.A. | Process for the production of 1,3-butadiene |
JP2014210755A (en) * | 2013-04-22 | 2014-11-13 | 昭和電工株式会社 | Method for producing butadiene |
KR101621796B1 (en) * | 2014-04-10 | 2016-05-19 | 한국화학연구원 | A process preparing butadiene and apparatus for preparing the same |
EP2949456A4 (en) * | 2013-01-23 | 2016-09-28 | Sekisui Chemical Co Ltd | Method for producing recycled material, and tire and method for producing tire |
EP3090801A1 (en) | 2015-05-08 | 2016-11-09 | The Siam Cement Public Company Limited | Catalyst for 1,3-butadiene production from ethanol |
WO2017009105A1 (en) | 2015-07-13 | 2017-01-19 | IFP Energies Nouvelles | Mesoporous mixed-oxide catalyst including silicon |
WO2017009108A1 (en) | 2015-07-13 | 2017-01-19 | IFP Energies Nouvelles | Ta-nb catalyst for the production of 1,3-butadiene |
US9878965B2 (en) | 2013-06-13 | 2018-01-30 | Basf Se | Process for the preparation of butadiene |
WO2018147934A1 (en) * | 2017-02-07 | 2018-08-16 | Battelle Memorial Institute | Single step conversion of ethanol to butadiene |
US10300459B2 (en) * | 2016-06-07 | 2019-05-28 | Fina Technology, Inc. | Metal oxide catalyst systems for conversion of ethanol to butadiene |
WO2021052968A1 (en) | 2019-09-16 | 2021-03-25 | Synthos Dwory 7 Spolka Z Ograniczona Odpowiedzialnoscia Spolka Jawna | Supported tantalum catalyst for the production of 1,3-butadiene |
WO2022207896A1 (en) | 2021-04-01 | 2022-10-06 | Synthos S.A. | Use of a catalyst system in the production of 1,3-butadiene from ethanol in two stages |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9689615B2 (en) | 2012-08-21 | 2017-06-27 | Uop Llc | Steady state high temperature reactor |
US9023255B2 (en) | 2012-08-21 | 2015-05-05 | Uop Llc | Production of nitrogen compounds from a methane conversion process |
US9656229B2 (en) | 2012-08-21 | 2017-05-23 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
US8927769B2 (en) | 2012-08-21 | 2015-01-06 | Uop Llc | Production of acrylic acid from a methane conversion process |
US9707530B2 (en) | 2012-08-21 | 2017-07-18 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
US9370757B2 (en) | 2012-08-21 | 2016-06-21 | Uop Llc | Pyrolytic reactor |
US8937186B2 (en) | 2012-08-21 | 2015-01-20 | Uop Llc | Acids removal and methane conversion process using a supersonic flow reactor |
US9308513B2 (en) | 2012-08-21 | 2016-04-12 | Uop Llc | Production of vinyl chloride from a methane conversion process |
US9327265B2 (en) | 2012-08-21 | 2016-05-03 | Uop Llc | Production of aromatics from a methane conversion process |
US20140058146A1 (en) * | 2012-08-21 | 2014-02-27 | Uop Llc | Production of butadiene from a methane conversion process |
US9434663B2 (en) | 2012-08-21 | 2016-09-06 | Uop Llc | Glycols removal and methane conversion process using a supersonic flow reactor |
US8933275B2 (en) | 2012-08-21 | 2015-01-13 | Uop Llc | Production of oxygenates from a methane conversion process |
US9205398B2 (en) | 2012-08-21 | 2015-12-08 | Uop Llc | Production of butanediol from a methane conversion process |
RU2503650C1 (en) * | 2012-11-16 | 2014-01-10 | Открытое акционерное общество Научно-исследовательский институт "Ярсинтез" (ОАО НИИ "Ярсинтез") | Method of producing butadiene by converting ethanol (versions) |
WO2014199348A2 (en) * | 2013-06-13 | 2014-12-18 | Basf Se | Metal doped silicate catalysts for the selective conversion of ethanol to butadiene |
FR3026101B1 (en) * | 2014-09-19 | 2017-05-26 | Ifp Energies Now | PROCESS FOR PRODUCING BUTADIENE FROM ETHANOL IN A REACTIONAL STEP WITH LOW WATER AND ENERGY CONSUMPTION |
FR3026100B1 (en) * | 2014-09-19 | 2016-12-09 | Ifp Energies Now | PROCESS FOR PRODUCING BUTADIENE AND HYDROGEN FROM ETHANOL IN TWO REACTIONAL STEPS WITH LOW WATER AND ENERGY CONSUMPTION |
WO2016066873A1 (en) | 2014-10-30 | 2016-05-06 | Abengoa Research, S.L. | Mixed oxides comprising magnesium and boron, and use thereof as catalysts for producing butadiene precursors |
RU2571831C1 (en) * | 2014-12-26 | 2015-12-20 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт нефтехимического синтеза им. А.В. Топчиева Российской академии наук (ИНХС РАН) | Catalyst for obtaining alkadienes (versions) and method for obtaining alkadienes with thereof application (versions) |
JP6627219B2 (en) * | 2015-01-05 | 2020-01-08 | 株式会社Ihi | Olefin production method |
WO2016111203A1 (en) * | 2015-01-05 | 2016-07-14 | 日揮株式会社 | Method for producing 1,3-butadiene |
FR3038851B1 (en) * | 2015-07-13 | 2019-11-08 | IFP Energies Nouvelles | CATALYST BASED ON TANTALUM BASED ON SILICA FOR THE TRANSFORMATION OF ETHANOL TO BUTADIENE |
FR3038852B1 (en) * | 2015-07-13 | 2019-11-29 | IFP Energies Nouvelles | STABILIZED PRODUCTION OF 1,3-BUTADIENE IN THE PRESENCE OF A TANTALIUM OXIDE DOPED BY AN ALDOLIZING ELEMENT |
RU2603198C1 (en) * | 2015-08-10 | 2016-11-27 | Открытое акционерное общество Научно-исследовательский институт "Ярсинтез" (ОАО НИИ "Ярсинтез") | Method of producing butadiene |
JP6652364B2 (en) * | 2015-10-14 | 2020-02-19 | 株式会社ダイセル | Method for producing 1,3-butadiene |
CN105251507B (en) * | 2015-10-16 | 2019-03-29 | 安徽工业大学 | Use AgO/CuO-MgO-SiO2The method of four component composite oxide catalysts catalysis ethanol butadiene |
CN105237321B (en) * | 2015-10-16 | 2018-11-13 | 安徽工业大学 | Use AgO/Cr2O3-MgO-SiO2The method of four component composite oxide catalysts catalysis ethanol butadiene |
CN105413695B (en) * | 2015-12-22 | 2018-09-25 | 中国科学院山西煤炭化学研究所 | A kind of ethanol condensed catalyst and preparation method and application for preparing 1,3- butadiene |
FR3053331B1 (en) * | 2016-06-29 | 2018-08-03 | IFP Energies Nouvelles | PROCESS FOR PRODUCING BUTADIENE FROM INTEGRATED ETHANOL WITH EXTRACTIVE DISTILLATION |
CN106861752A (en) * | 2017-01-09 | 2017-06-20 | 北京化工大学 | Solid catalyst and its preparation and application for ethanol synthesis butadiene |
RU2656602C1 (en) | 2017-03-31 | 2018-06-06 | Общество с ограниченной ответственностью "ЭТБ каталитические технологии" (ООО "ЭТБ КаТ") | One-step method of obtaining butadiene |
EP3476479A1 (en) * | 2017-10-25 | 2019-05-01 | Centre National De La Recherche Scientifique | New metallic catalysts |
RU2680828C1 (en) * | 2017-12-15 | 2019-02-28 | Общество с ограниченной ответственностью "ЭТБ каталитические технологии" (ООО "ЭТБ КаТ") | One-step method of obtaining butadiene |
CN112275270A (en) * | 2019-07-25 | 2021-01-29 | 中国科学院大连化学物理研究所 | Supported catalyst and preparation method thereof |
CN112295556A (en) * | 2019-07-29 | 2021-02-02 | 中国科学院大连化学物理研究所 | Supported catalyst and preparation method thereof |
JP7500015B2 (en) * | 2020-06-09 | 2024-06-17 | 横浜ゴム株式会社 | Solid catalyst and method for producing butadiene |
CN115518670B (en) * | 2021-06-24 | 2023-10-31 | 中国石油化工股份有限公司 | Olefination catalyst, its preparation method and application |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2357855A (en) | 1941-12-15 | 1944-09-12 | Szukiewicz Waclaw | Method for producing butadiene |
US2374433A (en) | 1942-06-08 | 1945-04-24 | Universal Oil Prod Co | Production of butadiene |
GB573631A (en) | 1941-12-15 | 1945-11-29 | Waclaw Szukiewicz | Manufacture of butadiene |
FR925617A (en) * | 1942-09-29 | 1947-09-09 | Carbide & Carbon Chem Corp | Process for preparing olefins |
US2436125A (en) | 1944-08-30 | 1948-02-17 | Rohm & Haas | Silica-zirconia catalysts and method of preparation |
US2438464A (en) | 1944-08-30 | 1948-03-23 | Rohm & Haas | Catalytic process for producing butadiene |
US2477181A (en) | 1942-07-06 | 1949-07-26 | Turco Products Inc | Composition and method for cleaning aluminum preparatory to spot welding |
US2548883A (en) * | 1946-09-07 | 1951-04-17 | Koppers Co Inc | Process of removing carbon from catalyst |
JPS57102822A (en) | 1980-12-16 | 1982-06-26 | Takeda Chem Ind Ltd | Preparation of butadiene |
JPS5859928A (en) | 1981-10-02 | 1983-04-09 | Takeda Chem Ind Ltd | Preparation of butadiene |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU68428A1 (en) | 1940-05-03 | 1946-11-30 | В.А. Покровский | The method of producing divinyl |
US2421361A (en) * | 1942-09-29 | 1947-05-27 | Carbide & Carbon Chem Corp | Process for making diolefins |
US2403743A (en) * | 1944-03-16 | 1946-07-09 | Carbide & Carbon Chem Corp | Cyclic butadiene process |
US2423681A (en) * | 1944-08-30 | 1947-07-08 | Rohm & Haas | Use of magnesia catalysts in the production of butadiene |
US2800517A (en) * | 1953-06-26 | 1957-07-23 | Publicker Ind Inc | Process for manufacturing butadiene |
-
2010
- 2010-07-29 RU RU2010131711/04A patent/RU2440962C1/en active
-
2011
- 2011-07-27 MY MYPI2013700145A patent/MY162490A/en unknown
- 2011-07-27 AU AU2011283229A patent/AU2011283229B2/en not_active Ceased
- 2011-07-27 MX MX2013000974A patent/MX2013000974A/en active IP Right Grant
- 2011-07-27 KR KR1020137004644A patent/KR101904163B1/en active IP Right Grant
- 2011-07-27 UA UAA201302090A patent/UA104257C2/en unknown
- 2011-07-27 CN CN201180037102.5A patent/CN103038196B/en active Active
- 2011-07-27 WO PCT/RU2011/000565 patent/WO2012015340A1/en active Application Filing
- 2011-07-27 US US13/812,310 patent/US8921635B2/en active Active
- 2011-07-27 EP EP11776035.5A patent/EP2598465B1/en active Active
- 2011-07-27 CA CA2804371A patent/CA2804371C/en not_active Expired - Fee Related
- 2011-07-27 PE PE2013000127A patent/PE20131061A1/en active IP Right Grant
- 2011-07-27 BR BR112013002225A patent/BR112013002225A2/en not_active IP Right Cessation
- 2011-07-27 JP JP2013521736A patent/JP5864572B2/en active Active
- 2011-07-27 PL PL11776035.5T patent/PL2598465T3/en unknown
-
2013
- 2013-02-28 ZA ZA2013/01531A patent/ZA201301531B/en unknown
- 2013-10-09 HK HK13111368.6A patent/HK1183860A1/en not_active IP Right Cessation
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2357855A (en) | 1941-12-15 | 1944-09-12 | Szukiewicz Waclaw | Method for producing butadiene |
GB573631A (en) | 1941-12-15 | 1945-11-29 | Waclaw Szukiewicz | Manufacture of butadiene |
US2374433A (en) | 1942-06-08 | 1945-04-24 | Universal Oil Prod Co | Production of butadiene |
US2477181A (en) | 1942-07-06 | 1949-07-26 | Turco Products Inc | Composition and method for cleaning aluminum preparatory to spot welding |
FR925617A (en) * | 1942-09-29 | 1947-09-09 | Carbide & Carbon Chem Corp | Process for preparing olefins |
US2436125A (en) | 1944-08-30 | 1948-02-17 | Rohm & Haas | Silica-zirconia catalysts and method of preparation |
US2438464A (en) | 1944-08-30 | 1948-03-23 | Rohm & Haas | Catalytic process for producing butadiene |
US2548883A (en) * | 1946-09-07 | 1951-04-17 | Koppers Co Inc | Process of removing carbon from catalyst |
JPS57102822A (en) | 1980-12-16 | 1982-06-26 | Takeda Chem Ind Ltd | Preparation of butadiene |
JPS5859928A (en) | 1981-10-02 | 1983-04-09 | Takeda Chem Ind Ltd | Preparation of butadiene |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2712673A1 (en) | 2012-09-28 | 2014-04-02 | LANXESS Deutschland GmbH | Method for manufacturing 1,3-butadiene |
WO2014049158A1 (en) | 2012-09-28 | 2014-04-03 | Lanxess Deutschland Gmbh | Method for producing 1,3-butadiene |
KR101440002B1 (en) * | 2012-10-12 | 2014-09-12 | 한국화학연구원 | Tantala-based complex metal oxide supported on silica-based catalysts for the production of 1,3-butadiene from ethanol and production method of 1,3-butadiene using thereof |
WO2014061917A1 (en) * | 2012-10-19 | 2014-04-24 | 한국화학연구원 | Regular mesoporous silica-based catalyst for preparing 1,3-butadiene from ethanol, and method for preparing 1,3-butadiene using same |
RU2514425C1 (en) * | 2012-11-16 | 2014-04-27 | Открытое акционерное общество Научно-исследовательский институт "Ярсинтез" (ОАО НИИ "Ярсинтез") | Catalyst for producing butadiene by converting ethanol |
EP2949456A4 (en) * | 2013-01-23 | 2016-09-28 | Sekisui Chemical Co Ltd | Method for producing recycled material, and tire and method for producing tire |
EP3763518A1 (en) * | 2013-01-23 | 2021-01-13 | Sekisui Chemical Co., Ltd. | Method for producing a tire |
US10899968B2 (en) | 2013-01-23 | 2021-01-26 | Sekisui Chemical Co., Ltd. | Method for producing recycled material, and tire and method for producing tire |
US11492554B2 (en) | 2013-01-23 | 2022-11-08 | Sekisui Chemical Co., Ltd. | Method for producing recycled material, and tire and method for producing tire |
JP2014210755A (en) * | 2013-04-22 | 2014-11-13 | 昭和電工株式会社 | Method for producing butadiene |
JP2016518395A (en) * | 2013-05-07 | 2016-06-23 | シントス エス.アー.Synthos S.A. | Process for producing 1,3-butadiene |
CN105263621A (en) * | 2013-05-07 | 2016-01-20 | 西索斯公司 | Process for the production of 1,3-butadiene |
RU2612975C1 (en) * | 2013-05-07 | 2017-03-14 | Синтос С.А. | Method of producing 1,3-butadiene |
US9656244B2 (en) | 2013-05-07 | 2017-05-23 | Synthos S.A. | Process for the production of 1,3-butadiene |
WO2014180778A1 (en) * | 2013-05-07 | 2014-11-13 | Synthos S.A. | Process for the production of 1,3-butadiene |
US9878965B2 (en) | 2013-06-13 | 2018-01-30 | Basf Se | Process for the preparation of butadiene |
KR101621796B1 (en) * | 2014-04-10 | 2016-05-19 | 한국화학연구원 | A process preparing butadiene and apparatus for preparing the same |
EP3090801A1 (en) | 2015-05-08 | 2016-11-09 | The Siam Cement Public Company Limited | Catalyst for 1,3-butadiene production from ethanol |
WO2017009105A1 (en) | 2015-07-13 | 2017-01-19 | IFP Energies Nouvelles | Mesoporous mixed-oxide catalyst including silicon |
US10792644B2 (en) * | 2015-07-13 | 2020-10-06 | IFP Energies Nouvelles | Catalyst Ta-Nb for the production of 1,3-butadiene |
WO2017009108A1 (en) | 2015-07-13 | 2017-01-19 | IFP Energies Nouvelles | Ta-nb catalyst for the production of 1,3-butadiene |
US10300459B2 (en) * | 2016-06-07 | 2019-05-28 | Fina Technology, Inc. | Metal oxide catalyst systems for conversion of ethanol to butadiene |
US10647625B2 (en) | 2017-02-07 | 2020-05-12 | Battelle Memorial Institute | Single step conversion of ethanol to butadiene |
WO2018147934A1 (en) * | 2017-02-07 | 2018-08-16 | Battelle Memorial Institute | Single step conversion of ethanol to butadiene |
WO2021052968A1 (en) | 2019-09-16 | 2021-03-25 | Synthos Dwory 7 Spolka Z Ograniczona Odpowiedzialnoscia Spolka Jawna | Supported tantalum catalyst for the production of 1,3-butadiene |
WO2022207896A1 (en) | 2021-04-01 | 2022-10-06 | Synthos S.A. | Use of a catalyst system in the production of 1,3-butadiene from ethanol in two stages |
Also Published As
Publication number | Publication date |
---|---|
US8921635B2 (en) | 2014-12-30 |
CA2804371A1 (en) | 2012-02-02 |
MY162490A (en) | 2017-06-15 |
ZA201301531B (en) | 2014-04-30 |
CA2804371C (en) | 2016-09-06 |
CN103038196B (en) | 2016-04-27 |
PE20131061A1 (en) | 2013-09-23 |
PL2598465T3 (en) | 2016-09-30 |
CN103038196A (en) | 2013-04-10 |
EP2598465A1 (en) | 2013-06-05 |
JP2013535465A (en) | 2013-09-12 |
EP2598465B1 (en) | 2016-01-20 |
AU2011283229B2 (en) | 2016-05-12 |
KR20140004621A (en) | 2014-01-13 |
BR112013002225A2 (en) | 2016-05-24 |
RU2440962C1 (en) | 2012-01-27 |
MX2013000974A (en) | 2013-05-17 |
HK1183860A1 (en) | 2014-01-10 |
US20130123554A1 (en) | 2013-05-16 |
UA104257C2 (en) | 2014-01-10 |
JP5864572B2 (en) | 2016-02-17 |
AU2011283229A1 (en) | 2013-02-21 |
KR101904163B1 (en) | 2018-10-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2011283229B2 (en) | One-step method for butadiene production | |
US7091155B2 (en) | Catalyst for ester production and process for producing ester | |
JP2013535465A5 (en) | ||
WO2014199349A2 (en) | Metal impregnated amorphous silicates for the selective conversion of ethanol to butadiene | |
WO2007126421A1 (en) | Hydrogenation of aromatic compounds | |
US20140194649A1 (en) | Process for the acetoxylation of olefins in the gas phase | |
TWI577658B (en) | Method for preparation of dimethyl 1,4-cyclohexanedicarboxylate and method for preparation of 1,4-cyclohexanedimethanol | |
WO2007099111A1 (en) | A hydrogenation process for the conversion of a carboxylic acid or an ester having a carbonyl group | |
CN103420776B (en) | A kind of method preparing methyl cyclopentene | |
US7465816B2 (en) | Production of tetrahydrofuran from 1,4-butanediol | |
TWI547478B (en) | Method for producing n-propyl acetate and method for producing allyl acetate | |
RU2412148C1 (en) | Single-step method of producing isoprene | |
EP3696172A1 (en) | Method for producing 2,5-bis (aminomethyl) tetrahydrofuran | |
US4619947A (en) | Chemical process | |
JP7109018B2 (en) | Solid catalyst and method for producing butadiene | |
JP3795974B2 (en) | Process for producing α, β-cyclic unsaturated ether | |
JPH11158102A (en) | Production of dibutyl ether | |
JPH11171811A (en) | Production of dibutyl ether | |
ZA200107560B (en) | Catalyst for ester production and process for producing ester. | |
JPH0148270B2 (en) | ||
JPH10316620A (en) | Production of diacetoxybutene | |
ZA200210054B (en) | Intergrated process for the production of vinyl ecetate. | |
JPS6185343A (en) | Selective production of methyl isobutyl ketone | |
WO2011104738A2 (en) | Process for the production of ethyl-acetate from ethanol | |
JPH10226659A (en) | Production of 7-octen-1-al |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201180037102.5 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11776035 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2804371 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 000127-2013 Country of ref document: PE |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/A/2013/000974 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13812310 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2013521736 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: A201302090 Country of ref document: UA |
|
ENP | Entry into the national phase |
Ref document number: 2011283229 Country of ref document: AU Date of ref document: 20110727 Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011776035 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 20137004644 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: A20130253 Country of ref document: BY |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112013002225 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112013002225 Country of ref document: BR Kind code of ref document: A2 Effective date: 20130129 |