SG11201903003QA - Process for producing dienes - Google Patents
Process for producing dienesInfo
- Publication number
- SG11201903003QA SG11201903003QA SG11201903003QA SG11201903003QA SG11201903003QA SG 11201903003Q A SG11201903003Q A SG 11201903003QA SG 11201903003Q A SG11201903003Q A SG 11201903003QA SG 11201903003Q A SG11201903003Q A SG 11201903003QA SG 11201903003Q A SG11201903003Q A SG 11201903003QA
- Authority
- SG
- Singapore
- Prior art keywords
- butanediol
- international
- alkenol
- butadiene
- bio
- Prior art date
Links
- 150000001993 dienes Chemical class 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 3
- 229910021536 Zeolite Inorganic materials 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 2
- 238000006297 dehydration reaction Methods 0.000 abstract 2
- 150000002009 diols Chemical class 0.000 abstract 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract 2
- 239000010457 zeolite Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 abstract 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
Classifications
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- 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
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
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- 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
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/084—Y-type faujasite
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7007—Zeolite Beta
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7034—MTW-type, e.g. ZSM-12, NU-13, TPZ-12 or Theta-3
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/643—Pore diameter less than 2 nm
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/651—50-500 nm
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
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- 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
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
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- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/37—Acid treatment
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- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/42—Addition of matrix or binder particles
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/66—Pore distribution
- B01J35/69—Pore distribution bimodal
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nanotechnology (AREA)
Abstract
International Patent Classification: C07C 1/24 (2006.01) C07C 33/03 C07C 11/167 (2006.01) B01J 23/10 C07C 29/60 (2006.01) B01J 29/08 C07C 33/025 (2006.01) B01J 29/70 EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). (2006.01) (2006.01) (2006.01) (2006.01) co N O co O C (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 26 April 2018 (26.04.2018) WIP0 I PCT omit VIII °nolo olomll monoloino oimIE (10) International Publication Number WO 2018/073282 Al (21) International Application Number: (22) International Filing Date: PCT/EP2017/076554 Published: — with international search report (Art. 21(3)) 18 October 2017 (18.10.2017) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 102016000105178 19 October 2016 (19.10.2016) IT (71) Applicant: VERSALIS S.P.A. [IT/IT]; P.zza Boldrini, 1, 1-20097 San Donato Milanese (MI) (IT). (72) Inventors: DELLEDONNE, Daniele; Via Romana, 56, 1-28047 Oleggio (NO) (IT). CESANA, Alberto; Vicolo Del Castagno 13, 1-28066 Galliate (NO) (IT). MATTACHINI, Marco; Via Castello 1, 1-28040 Mezzomerico (NO) (IT). PASTORI, Monica Vittoria; Via Bellotti, 6,1-20012 Cug- giono (MI) (IT). (74) Agent: MAURO, Marina Eliana; C/O MURGITROYD & COMPANY, Piazza Borromeo, 12, 1-20123 Milano (IT). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (54) Title: PROCESS FOR PRODUCING DIENES (57) : The present invention relates to a process for producing a diene, preferably a conjugated diene, more preferably 1,3- butadiene, comprising the dehydration of at least one alkenol having a number of carbon atoms greater than or equal to 4, in the presence of a catalytic material comprising at least one crystalline metalosilicate in acid form, preferably a macroporous zeolite, more preferably a zeolite with a FAU, BEA or MTW structure. Preferably, said alkenol having a number of carbon atoms greater than or equal to 4 may be obtained directly through biosynthetic processes, or through catalytic dehydration processes of at least one diol. When said alkenol is a butenol, said diol is preferably a butanediol, more preferably 1,3-butanediol, even more preferably bio-1,3-butanediol, i.e. 1,3- butanediol deriving from biosynthetic processes. When said alkenol is 1,3-butanediol, or bio-1,3-butanediol, the diene obtained with the process according to the present invention is, respectively, 1,3-butadiene, or bio-1,3-butadiene.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT102016000105178A IT201600105178A1 (en) | 2016-10-19 | 2016-10-19 | Process for the production of dienes |
PCT/EP2017/076554 WO2018073282A1 (en) | 2016-10-19 | 2017-10-18 | Process for producing dienes |
Publications (1)
Publication Number | Publication Date |
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SG11201903003QA true SG11201903003QA (en) | 2019-05-30 |
Family
ID=58159387
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SG11201903003QA SG11201903003QA (en) | 2016-10-19 | 2017-10-18 | Process for producing dienes |
Country Status (20)
Country | Link |
---|---|
US (1) | US11498887B2 (en) |
EP (1) | EP3529227B1 (en) |
JP (1) | JP7033127B2 (en) |
KR (1) | KR102503689B1 (en) |
CN (1) | CN109982989B (en) |
BR (1) | BR112019007826B1 (en) |
CA (1) | CA3039337A1 (en) |
CL (1) | CL2019000930A1 (en) |
DK (1) | DK3529227T3 (en) |
EA (1) | EA037338B1 (en) |
ES (1) | ES2914251T3 (en) |
HU (1) | HUE058302T2 (en) |
IL (1) | IL265894B (en) |
IT (1) | IT201600105178A1 (en) |
MX (1) | MX2019003924A (en) |
PL (1) | PL3529227T3 (en) |
SA (1) | SA519401572B1 (en) |
SG (1) | SG11201903003QA (en) |
TN (1) | TN2019000104A1 (en) |
WO (1) | WO2018073282A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018064604A1 (en) | 2016-09-30 | 2018-04-05 | Hong Je Cho | Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene |
KR20210068049A (en) * | 2018-09-21 | 2021-06-08 | 베르살리스 에스.피.에이. | Purification process of bio-1,3-butanediol from fermentation broth |
US11472753B2 (en) | 2019-07-05 | 2022-10-18 | Sekisui Chemical Co., Ltd. | Method for producing 1,3-butadiene |
WO2021006250A1 (en) * | 2019-07-05 | 2021-01-14 | 積水化学工業株式会社 | Method for producing 1,3-butadiene |
IT201900015069A1 (en) * | 2019-08-27 | 2021-02-27 | Versalis Spa | CATALYST INCLUDING COKE AND PROCEDURE FOR THE PRODUCTION OF DIENES. |
CN112958146B (en) * | 2019-12-12 | 2022-04-19 | 中国科学院大连化学物理研究所 | MFI molecular sieve nanosheet-loaded zirconium-based catalyst and application thereof in butadiene preparation reaction |
IT201900025000A1 (en) | 2019-12-20 | 2021-06-20 | Versalis Spa | PROCEDURE FOR THE PRODUCTION OF DIENES. |
CN115364844A (en) * | 2021-05-21 | 2022-11-22 | 中国石油化工股份有限公司 | Regenerated deoxidation catalyst and preparation method and application thereof |
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ITMI20132069A1 (en) | 2013-12-11 | 2015-06-12 | Versalis Spa | PROCEDURE FOR THE PRODUCTION OF BIOMASS SUGARS |
JP6081949B2 (en) * | 2014-03-25 | 2017-02-15 | Jxエネルギー株式会社 | Dehydration catalyst and method for producing conjugated diene |
JP6081950B2 (en) * | 2014-03-25 | 2017-02-15 | Jxエネルギー株式会社 | Dehydration catalyst and method for producing conjugated diene |
WO2015146789A1 (en) * | 2014-03-25 | 2015-10-01 | Jx日鉱日石エネルギー株式会社 | Dehydration catalyst and method for producing conjugated diene |
RU2695786C2 (en) * | 2014-05-16 | 2019-07-26 | ВЕРСАЛИС С.п.А. | Method of producing alkenols and use thereof for producing 1,3-butadiene |
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KR102287828B1 (en) * | 2014-12-17 | 2021-08-10 | 에스케이이노베이션 주식회사 | Method for Recovering 1,3-Butadiene and Methylethylketone from Dehydration Products of 2,3-Butanediol |
CN105712819B (en) * | 2014-12-17 | 2020-08-07 | Sk新技术株式会社 | Method for recovering 1, 3-butadiene and methyl ethyl ketone from 2,3-butanediol dehydration product |
JP6672325B2 (en) | 2015-02-23 | 2020-03-25 | ヴェルサリス ソシエタ ペル アチオニ | Diene production method |
US10179323B2 (en) * | 2016-06-07 | 2019-01-15 | Fina Technology, Inc. | Metal oxide catalyst systems for conversion of ethanol to butadiene |
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2016
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2017
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JP2019532065A (en) | 2019-11-07 |
BR112019007826B1 (en) | 2022-05-24 |
KR102503689B1 (en) | 2023-02-23 |
IT201600105178A1 (en) | 2018-04-19 |
EA037338B1 (en) | 2021-03-15 |
IL265894B (en) | 2021-09-30 |
CN109982989B (en) | 2023-05-12 |
CL2019000930A1 (en) | 2019-08-02 |
US20190241481A1 (en) | 2019-08-08 |
ES2914251T3 (en) | 2022-06-08 |
EA201990649A1 (en) | 2019-09-30 |
MX2019003924A (en) | 2019-08-12 |
JP7033127B2 (en) | 2022-03-09 |
TN2019000104A1 (en) | 2020-10-05 |
HUE058302T2 (en) | 2022-07-28 |
WO2018073282A1 (en) | 2018-04-26 |
DK3529227T3 (en) | 2022-05-02 |
PL3529227T3 (en) | 2022-06-20 |
US11498887B2 (en) | 2022-11-15 |
EP3529227B1 (en) | 2022-04-06 |
CA3039337A1 (en) | 2018-04-26 |
BR112019007826A2 (en) | 2019-07-16 |
KR20190078594A (en) | 2019-07-04 |
SA519401572B1 (en) | 2022-12-27 |
CN109982989A (en) | 2019-07-05 |
IL265894A (en) | 2019-06-30 |
EP3529227A1 (en) | 2019-08-28 |
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