JP6478287B2 - 酸化脱水素反応を通じたブタジエンの製造方法 - Google Patents
酸化脱水素反応を通じたブタジエンの製造方法 Download PDFInfo
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- JP6478287B2 JP6478287B2 JP2016547551A JP2016547551A JP6478287B2 JP 6478287 B2 JP6478287 B2 JP 6478287B2 JP 2016547551 A JP2016547551 A JP 2016547551A JP 2016547551 A JP2016547551 A JP 2016547551A JP 6478287 B2 JP6478287 B2 JP 6478287B2
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- butadiene
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 182
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000002904 solvent Substances 0.000 claims description 59
- 239000007789 gas Substances 0.000 claims description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 238000010521 absorption reaction Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000001569 carbon dioxide Substances 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000010926 purge Methods 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 description 23
- 238000000746 purification Methods 0.000 description 21
- 238000000926 separation method Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000011084 recovery Methods 0.000 description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 238000010791 quenching Methods 0.000 description 9
- 238000006297 dehydration reaction Methods 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 8
- 208000005156 Dehydration Diseases 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- DKUYEPUUXLQPPX-UHFFFAOYSA-N dibismuth;molybdenum;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mo].[Mo].[Bi+3].[Bi+3] DKUYEPUUXLQPPX-UHFFFAOYSA-N 0.000 description 6
- 238000007872 degassing Methods 0.000 description 5
- 238000009434 installation Methods 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000001273 butane Substances 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3332—Catalytic processes with metal oxides or metal sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- 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
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/18—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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/28—Molybdenum
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/31—Chromium, molybdenum or tungsten combined with bismuth
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本出願は、2014年6月11日付韓国特許出願第10−2014−0071050号に基づいた優先権の利益を主張し、当該韓国特許出願の文献に開示されている全ての内容は本明細書の一部として含まれる。
本発明は、酸化脱水素反応を通じたブタジエンの製造方法に関する。
前述した酸化脱水素反応を通じたブタジエンの製造方法を実施するためのブタジエン製造装置は、C4留分、スチーム(steam)、酸素(O2)及び窒素(N2)を含む第1流れ30の各成分を反応器10内にそれぞれ流入させるための個別パイプラインを含むか、または反応器10と直接連結された一つのパイプラインから分岐され、前記第1流れに含まれる成分が個別的に投入される複数の個別パイプラインを含むことができる(図1を参照)。
先ず、C4留分、スチーム(steam)、酸素(O2)及び窒素(N2)を含む第1流れを反応器内に流入させて酸化脱水素反応を進めさせる(段階a)。
本発明の一実施形態において、前記反応器から得られる反応生成物は急冷段階を経ることができる。
本発明の一実施形態において、前記反応器から得られた反応生成物は水分を除去する脱水段階をさらに含むことができる。
本発明の一実施形態では、従来の技術とは異なり、反応器から得られる反応生成物のうちブタジエンを吸収溶媒に選択的に吸収させ、それ以外のC4混合物及びガス生成物は分離/除去する(段階b)。
本発明の一実施形態において、前記ブタジエンを溶解している吸収溶媒は、前記吸収溶媒を分離/回収するための溶媒回収塔23へ伝えられる。
以下、実施例を介して本発明をさらに詳しく説明する。これらの実施例はただ本発明を例示するためのものであって、本発明の範囲がこれらの実施例によって制限されるものと解釈されないのは、当業界で通常の知識を有する者において自明なはずである。
本発明に基づいてモリブデン酸ビスマス系触媒が充填された反応器でブタジエンを製造した。一方、前記反応器から得られる反応生成物のうちブタジエンを選択的に吸収させるためにジメチルホルムアミド(DMF)を吸収溶媒として用いて、1回の溶媒使用/除去の過程だけでブタジエンのみを得ることができた。
前記実施例1と同一の方法でブタジエンを製造し、但し、ガス分離及び精製段階のそれぞれで相違する溶媒を用いた。
21 吸収塔
22 脱気塔
23 溶媒回収塔
27 蒸溜塔
26 ブタジエン精製塔
30 第1流れ
40 第2流れ
50 第3流れ
60 急冷塔
Claims (4)
- a)C4留分、スチーム(steam)、酸素(O2)及び窒素(N2)を含む第1流れを、触媒が充填された反応器内に流入させて酸化脱水素反応を進めさせる段階;
b)前記反応器から得られた反応物でブタジエンを吸収溶媒に選択的に吸収させ、前記ブタジエンを除いたC4混合物及びガス生成物(light gas)を分離/除去する段階;
c)前記ブタジエンを回収して精製する段階;及び
d)前記b)段階で分離されたブタジエンを除いたC4混合物及びガス生成物(light gas)のうち、窒素及び二酸化炭素(CO 2 )からなる群より選択される一つ以上を含む第2流れは、循環させて反応器に再投入し、パージ(purge)を含む第3流れは系外部に排出させる段階;を含み、
前記段階b)は、吸収塔内で1回の吸収溶媒の使用で行われ、
前記ブタジエンを除いたC4混合物及びガス生成物は吸収塔で分離/除去されるものである
酸化脱水素反応を通じたブタジエンの製造方法。 - 前記吸収溶媒は、極性非プロトン性溶媒(polar aprotic solvent)である
請求項1に記載の酸化脱水素反応を通じたブタジエンの製造方法。 - 前記吸収溶媒は、ジメチルホルムアミド(dimethylformamide(DMF))、メチルピロリドン(methylpyrrolidone(NMP))、アセトニトリル(acetonitrile(ACN))、ジメチルアセトアミド(dimethylacetamide(DMA))及びジメチルスルホキシド(dimethyl sulfoxide(DMSO))からなる群より選択される一つまたは2以上の混合物である
請求項1または2に記載の酸化脱水素反応を通じたブタジエンの製造方法。 - 前記C4留分は、n−ブタン(n−butane)、トランス−2−ブテン(trans−2−butene)、シス−2−ブテン(cis−2−butene)及び1−ブテン(1−butene)からなる群より選択される一つ以上を含む単一化合物または混合物である
請求項1から3のいずれか一項に記載の酸化脱水素反応を通じたブタジエンの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR10-2014-0071050 | 2014-06-11 | ||
KR1020140071050A KR101717817B1 (ko) | 2014-06-11 | 2014-06-11 | 산화탈수소 반응을 통한 부타디엔 제조방법 |
PCT/KR2015/005770 WO2015190801A1 (ko) | 2014-06-11 | 2015-06-09 | 산화탈수소 반응을 통한 부타디엔 제조방법 |
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JP2017521355A JP2017521355A (ja) | 2017-08-03 |
JP6478287B2 true JP6478287B2 (ja) | 2019-03-06 |
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US (1) | US20160326071A1 (ja) |
EP (1) | EP3156386A4 (ja) |
JP (1) | JP6478287B2 (ja) |
KR (1) | KR101717817B1 (ja) |
CN (1) | CN105960388B (ja) |
WO (1) | WO2015190801A1 (ja) |
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KR102050834B1 (ko) * | 2016-03-17 | 2019-12-02 | 주식회사 엘지화학 | 부타디엔의 제조 방법 |
KR101902108B1 (ko) * | 2016-03-30 | 2018-09-28 | 주식회사 엘지화학 | 페라이트계 촉매, 이의 제조방법 및 이를 이용한 부타디엔의 제조방법 |
WO2018005162A1 (en) * | 2016-06-30 | 2018-01-04 | Uop Llc | Process for butadiene production via oxidative dehydrogenation followed by direct dehydrogenation |
WO2021059834A1 (ja) * | 2019-09-26 | 2021-04-01 | Jsr株式会社 | 1,3-ブタジエンの製造方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2382473A (en) * | 1941-03-13 | 1945-08-14 | Phillips Petroleum Co | Production of butadiene |
JPS57140730A (en) * | 1981-02-24 | 1982-08-31 | Nippon Zeon Co Ltd | Preparation of 1,3-butadiene |
JPS59167525A (ja) * | 1983-03-14 | 1984-09-21 | Japan Synthetic Rubber Co Ltd | 1,3−ブタジエンの製造方法 |
JPS60193931A (ja) * | 1984-03-13 | 1985-10-02 | Nippon Zeon Co Ltd | ブタジエンの回収法 |
DE102004061514A1 (de) * | 2004-12-21 | 2006-07-06 | Basf Ag | Verfahren zur Herstellung von Butadien aus n-Butan |
DE102005002127A1 (de) * | 2005-01-17 | 2006-07-20 | Basf Ag | Verfahren zur Herstellung von Butadien aus n-Butan |
JP5648319B2 (ja) * | 2009-05-29 | 2015-01-07 | 三菱化学株式会社 | 共役ジエンの製造方法 |
US8420879B2 (en) * | 2011-03-03 | 2013-04-16 | Basf Se | Process for workup of a stream comprising butene and/or butadiene |
US20140163290A1 (en) * | 2012-12-06 | 2014-06-12 | Basf Se | Process for the Oxidative Dehydrogenation of N-Butenes to Butadiene |
WO2015055613A1 (de) * | 2013-10-18 | 2015-04-23 | Basf Se | Verfahren zur herstellung von 1,3-butadien durch dehydrierung von n-butenen aus dem c4-schnitt eines steam-crackers |
WO2015076624A1 (ko) * | 2013-11-22 | 2015-05-28 | 주식회사 엘지화학 | 산화탈수소 반응을 통한 부타디엔 제조 공정 내 흡수 용매 회수방법 |
JP2016533319A (ja) * | 2013-11-22 | 2016-10-27 | エルジー・ケム・リミテッド | 酸化脱水素反応を介したブタジエン製造工程内の吸収溶媒の回収方法 |
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- 2015-06-09 JP JP2016547551A patent/JP6478287B2/ja active Active
- 2015-06-09 US US15/110,666 patent/US20160326071A1/en not_active Abandoned
- 2015-06-09 CN CN201580006690.4A patent/CN105960388B/zh active Active
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Publication number | Publication date |
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CN105960388A (zh) | 2016-09-21 |
CN105960388B (zh) | 2018-05-29 |
EP3156386A1 (en) | 2017-04-19 |
JP2017521355A (ja) | 2017-08-03 |
KR101717817B1 (ko) | 2017-03-17 |
WO2015190801A1 (ko) | 2015-12-17 |
US20160326071A1 (en) | 2016-11-10 |
EP3156386A4 (en) | 2017-05-17 |
KR20150142371A (ko) | 2015-12-22 |
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