JP2017532318A5 - - Google Patents
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- Publication number
- JP2017532318A5 JP2017532318A5 JP2017515814A JP2017515814A JP2017532318A5 JP 2017532318 A5 JP2017532318 A5 JP 2017532318A5 JP 2017515814 A JP2017515814 A JP 2017515814A JP 2017515814 A JP2017515814 A JP 2017515814A JP 2017532318 A5 JP2017532318 A5 JP 2017532318A5
- Authority
- JP
- Japan
- Prior art keywords
- effluent
- section
- ethanol
- fed
- scrubbing
- 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.)
- Granted
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 96
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 54
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 52
- 239000007788 liquid Substances 0.000 claims description 31
- 238000005201 scrubbing Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 230000006835 compression Effects 0.000 claims description 8
- 238000007906 compression Methods 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 8
- 239000003921 oil Substances 0.000 claims 8
- 239000004215 Carbon black (E152) Substances 0.000 claims 5
- 229930195733 hydrocarbon Natural products 0.000 claims 5
- 230000002745 absorbent Effects 0.000 claims 4
- 239000002250 absorbent Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000000895 extractive distillation Methods 0.000 claims 1
- 239000000295 fuel oil Substances 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- 238000000622 liquid--liquid extraction Methods 0.000 claims 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 claims 1
- 229940099427 potassium bisulfite Drugs 0.000 claims 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 239000012498 ultrapure water Substances 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1458859A FR3026100B1 (fr) | 2014-09-19 | 2014-09-19 | Procede de production de butadiene et d'hydrogene a partir d'ethanol en deux etapes reactionnelles a faible consommation en eau et en energie |
| FR1458859 | 2014-09-19 | ||
| PCT/EP2015/071361 WO2016042095A1 (fr) | 2014-09-19 | 2015-09-17 | Procede de production de butadiene et d'hydrogene a partir d'ethanol en deux etapes reactionnelles a faible consommation en eau et en energie |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017532318A JP2017532318A (ja) | 2017-11-02 |
| JP2017532318A5 true JP2017532318A5 (enExample) | 2018-10-25 |
| JP6594416B2 JP6594416B2 (ja) | 2019-10-23 |
Family
ID=51932466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017515814A Active JP6594416B2 (ja) | 2014-09-19 | 2015-09-17 | 低水かつ低エネルギー消費の２反応工程におけるエタノールからのブタジエンおよび水素の製造方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10358396B2 (enExample) |
| EP (1) | EP3194349B1 (enExample) |
| JP (1) | JP6594416B2 (enExample) |
| KR (1) | KR102411988B1 (enExample) |
| CN (1) | CN106715365B (enExample) |
| BR (1) | BR112017004046B1 (enExample) |
| CA (1) | CA2960715C (enExample) |
| FR (1) | FR3026100B1 (enExample) |
| MY (1) | MY182714A (enExample) |
| PL (1) | PL3194349T3 (enExample) |
| RU (1) | RU2672877C2 (enExample) |
| TW (1) | TWI718996B (enExample) |
| UA (1) | UA121317C2 (enExample) |
| WO (1) | WO2016042095A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3051124B1 (fr) * | 2016-05-12 | 2018-06-01 | IFP Energies Nouvelles | Utilisation d'un solvant donneur de lewis pour la purification d'une charge comprenant de l'ethanol, de l'acetaldehyde, et des impuretes |
| FR3053331B1 (fr) * | 2016-06-29 | 2018-08-03 | IFP Energies Nouvelles | Procede de production de butadiene a partir d'ethanol integre avec distillation extractive |
| FR3053332B1 (fr) * | 2016-06-29 | 2018-08-03 | IFP Energies Nouvelles | Procede de production de butadiene a partir d'ethanol comprenant une purification d'un effluent riche en butadiene par distillation extractive |
| FR3057467B1 (fr) * | 2016-10-17 | 2018-12-07 | IFP Energies Nouvelles | Procede de purification d'une solution aqueuse comprenant du diethylacetal |
| FR3058720B1 (fr) | 2016-11-17 | 2018-12-07 | IFP Energies Nouvelles | Hydrogenation des effluents liquides d'une unite de production de butadiene a partir d'ethanol |
| FR3060559A1 (fr) | 2016-12-21 | 2018-06-22 | IFP Energies Nouvelles | Procede de traitement d'une solution aqueuse comprenant de l'ethanol utilisant une colonne a cloison |
| FR3060558B1 (fr) * | 2016-12-21 | 2019-05-24 | IFP Energies Nouvelles | Procede de production de butadiene comprenant des etapes de separation ameliorees |
| JP7160604B2 (ja) * | 2017-08-30 | 2022-10-25 | 積水化学工業株式会社 | １，３－ブタジエン及びアセトアルデヒドジエチルアセタールの製造方法 |
| FR3077994B1 (fr) | 2018-02-22 | 2020-02-28 | IFP Energies Nouvelles | Separation selective des impuretes presentes dans une coupe hydroalcoolique par recyclage dans une colonne d'extraction liquide-liquide |
| FR3081726B1 (fr) | 2018-06-01 | 2020-05-29 | IFP Energies Nouvelles | Methode d'extraction partielle de butanol d'une solution aqueuse comprenant de l'ethanol et du butanol |
| FR3086548B1 (fr) | 2018-09-28 | 2020-10-30 | Ifp Energies Now | Procede de purification d'une charge hydroalcoolique comprenant de l'ethanol, de l'acetaldehyde et des impuretes |
| FR3090632B1 (fr) | 2018-12-21 | 2020-12-25 | Ifp Energies Now | Procédé de production de butadiène à partir d’éthanol avec régénération in situ optimisée du catalyseur de la deuxième étape réactionnelle |
| FR3090631B1 (fr) | 2018-12-21 | 2020-12-25 | Ifp Energies Now | Procédé de production de butadiène à partir d’éthanol avec régénération in situ du catalyseur de la deuxième étape réactionnelle |
| FR3095441B1 (fr) | 2019-04-25 | 2022-12-23 | Ifp Energies Now | Procede de purification d’une charge hydroalcoolique comprenant de l’ethanol, de l’acetaldehyde |
| CN114364650A (zh) * | 2019-07-05 | 2022-04-15 | 积水化学工业株式会社 | 1,3-丁二烯的制造方法 |
| US11472753B2 (en) * | 2019-07-05 | 2022-10-18 | Sekisui Chemical Co., Ltd. | Method for producing 1,3-butadiene |
| EP4100382B1 (en) | 2020-02-06 | 2025-11-12 | SABIC Global Technologies B.V. | Systems and methods for enhancing the extractive section operability and modifying solvent heat recovery cycle in the separation of c4 mixtures |
| JP7546245B2 (ja) * | 2020-06-09 | 2024-09-06 | 横浜ゴム株式会社 | ブタジエンの製造方法およびブタジエンの製造装置 |
| FR3114590B1 (fr) * | 2020-09-25 | 2022-09-09 | Ifp Energies Now | Procédé de deshydrogenation de l’éthanol en reacteur multitubulaire |
| WO2022271796A2 (en) * | 2021-06-22 | 2022-12-29 | Battelle Memorial Institute | Systems and methods for preparing butenes |
| JP2023031584A (ja) * | 2021-08-25 | 2023-03-09 | 積水化学工業株式会社 | １，３－ブタジエンの製造方法及び１，３－ブタジエンの製造装置 |
| EP4444681A1 (en) * | 2021-12-08 | 2024-10-16 | Bridgestone Americas Tire Operations, LLC | Butadiene production from used tires |
| FR3131307A1 (fr) | 2021-12-23 | 2023-06-30 | IFP Energies Nouvelles | Procédé de deshydrogenation de l’éthanol en presence d’oxygene |
| FR3131306A1 (fr) | 2021-12-23 | 2023-06-30 | IFP Energies Nouvelles | Procédé de deshydrogenation de l’éthanol avec élimination de l’hydrogene et intégration thermique |
| FR3143602B1 (fr) | 2022-12-20 | 2024-11-15 | Ifp Energies Now | Conversion d’une charge hydrocarbonée issue de la biomasse pour produire de l’acide adipique |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1948777A (en) * | 1931-07-15 | 1934-02-27 | Carbide & Carbon Chem Corp | Process of separating hydrocarbons |
| US1977750A (en) * | 1931-12-07 | 1934-10-23 | Carbide & Carbon Chem Corp | Process for making acetaldehyde and a catalyst therefor |
| US2249847A (en) * | 1938-05-27 | 1941-07-22 | Carbide & Carbon Chem Corp | Recovery method for cyclic vapor phase reaction products |
| US2404743A (en) * | 1938-06-10 | 1946-07-23 | Prause Robert | Device for adjusting the pitch of air propellers |
| US2403742A (en) * | 1943-09-09 | 1946-07-09 | Carbide & Carbon Chem Corp | Process for making butadiene |
| US2403741A (en) * | 1943-09-09 | 1946-07-09 | Carbide & Carbon Chem Corp | Process for making butadiene |
| US2403743A (en) * | 1944-03-16 | 1946-07-09 | Carbide & Carbon Chem Corp | Cyclic butadiene process |
| US2393381A (en) * | 1944-04-27 | 1946-01-22 | Carbide & Carbon Chem Corp | Cyclic process for making butadiene |
| US2395057A (en) * | 1944-05-02 | 1946-02-19 | Carbide & Carbon Chem Corp | Recovery method in process for making butadiene |
| US2409250A (en) * | 1944-11-07 | 1946-10-15 | Carbide & Carbon Chem Corp | Separation of butadiene |
| US2439587A (en) * | 1945-05-17 | 1948-04-13 | Koppers Co Inc | Manufacture of dienes |
| KR101152768B1 (ko) * | 2010-04-22 | 2012-06-18 | 금호석유화학 주식회사 | 에탄올로부터 1,3-부타디엔 제조를 위한 나노 실리카계 촉매 및 이를 이용한 1,3-부타디엔의 제조방법 |
| RU2440962C1 (ru) * | 2010-07-29 | 2012-01-27 | Общество с ограниченной ответственностью "УНИСИТ" (ООО "УНИСИТ") | Одностадийный способ получения бутадиена |
| JP2013121939A (ja) * | 2011-12-12 | 2013-06-20 | Ichikawa Office Inc | ブタジエンの製造方法 |
| CN103172504B (zh) * | 2011-12-26 | 2014-10-08 | 南京工业大学 | 2,7-二甲基-2,4,6-辛三烯-1,8-二醛的合成方法 |
| RU2503650C1 (ru) * | 2012-11-16 | 2014-01-10 | Открытое акционерное общество Научно-исследовательский институт "Ярсинтез" (ОАО НИИ "Ярсинтез") | Способ получения бутадиена превращением этанола (варианты) |
-
2014
- 2014-09-19 FR FR1458859A patent/FR3026100B1/fr not_active Expired - Fee Related
-
2015
- 2015-09-17 EP EP15763370.2A patent/EP3194349B1/fr active Active
- 2015-09-17 RU RU2017113365A patent/RU2672877C2/ru active
- 2015-09-17 CA CA2960715A patent/CA2960715C/fr active Active
- 2015-09-17 JP JP2017515814A patent/JP6594416B2/ja active Active
- 2015-09-17 BR BR112017004046-8A patent/BR112017004046B1/pt active IP Right Grant
- 2015-09-17 PL PL15763370T patent/PL3194349T3/pl unknown
- 2015-09-17 KR KR1020177010427A patent/KR102411988B1/ko active Active
- 2015-09-17 UA UAA201703715A patent/UA121317C2/uk unknown
- 2015-09-17 MY MYPI2017700858A patent/MY182714A/en unknown
- 2015-09-17 CN CN201580050259.XA patent/CN106715365B/zh active Active
- 2015-09-17 WO PCT/EP2015/071361 patent/WO2016042095A1/fr not_active Ceased
- 2015-09-17 US US15/511,924 patent/US10358396B2/en active Active
- 2015-09-18 TW TW104131003A patent/TWI718996B/zh active
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