JP2018502857A5 - - Google Patents
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- Publication number
- JP2018502857A5 JP2018502857A5 JP2017536245A JP2017536245A JP2018502857A5 JP 2018502857 A5 JP2018502857 A5 JP 2018502857A5 JP 2017536245 A JP2017536245 A JP 2017536245A JP 2017536245 A JP2017536245 A JP 2017536245A JP 2018502857 A5 JP2018502857 A5 JP 2018502857A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydrofuran
- water
- column
- succinic anhydride
- boiling components
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 16
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 16
- 229940014800 succinic anhydride Drugs 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 9
- 239000001384 succinic acid Substances 0.000 claims description 8
- 238000000855 fermentation Methods 0.000 claims description 6
- 230000004151 fermentation Effects 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 150000003464 sulfur compounds Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002745 absorbent Effects 0.000 claims description 3
- 239000002250 absorbent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000002028 Biomass Substances 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 238000003795 desorption Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15150615 | 2015-01-09 | ||
| EP15150615.1 | 2015-01-09 | ||
| PCT/EP2016/050245 WO2016110556A1 (de) | 2015-01-09 | 2016-01-08 | Verfahren zur herstellung von tetrahydrofuran, 1,4-butandiol oder gamma-butyrolacton |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018502857A JP2018502857A (ja) | 2018-02-01 |
| JP2018502857A5 true JP2018502857A5 (enExample) | 2020-02-27 |
| JP6716574B2 JP6716574B2 (ja) | 2020-07-01 |
Family
ID=52444096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017536245A Expired - Fee Related JP6716574B2 (ja) | 2015-01-09 | 2016-01-08 | テトラヒドロフラン、１，４−ブタンジオール又はγ−ブチロラクトンの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10308623B2 (enExample) |
| EP (1) | EP3242870B1 (enExample) |
| JP (1) | JP6716574B2 (enExample) |
| KR (1) | KR20170102530A (enExample) |
| CN (1) | CN107108538B (enExample) |
| BR (1) | BR112017014623B1 (enExample) |
| CA (1) | CA2972303C (enExample) |
| ES (1) | ES2730109T3 (enExample) |
| WO (1) | WO2016110556A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3328820B1 (de) | 2015-07-29 | 2020-09-30 | Basf Se | Verfahren zur herstellung von monoethylenglykol |
| EP3436420B1 (de) | 2016-03-31 | 2019-12-04 | Basf Se | Verfahren zur hydrierung von carbonsäuren zu alkoholen |
| PT3512830T (pt) | 2016-09-14 | 2025-03-21 | Basf Se | Processo de hidrogenação de uma mistura na presença de uma amina incolor |
| CN107930642B (zh) * | 2017-10-23 | 2019-10-29 | 浙江大学 | 一种用于乙酰丙酸催化加氢制备γ-戊内酯的催化剂 |
| CN110862302B (zh) * | 2018-08-27 | 2022-10-28 | 中国石化扬子石油化工有限公司 | 一种浆态床加氢与固定床加氢组合制备1,4-丁二醇的方法 |
| US20240287011A1 (en) * | 2021-06-25 | 2024-08-29 | Cj Cheiljedang Corporation | Method for producing tetrahydrofuran, gamma-butyrolactone, or 1,4-butanediol |
| AU2023246326A1 (en) * | 2022-03-30 | 2024-10-24 | Cj Cheiljedang Corporation | Method of producing gamma-butyrolactone from biomass |
| CN115232059B (zh) * | 2022-08-01 | 2023-11-21 | 上海巽田科技股份有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的合成方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1141282B (de) | 1960-03-18 | 1962-12-20 | Hoechst Ag | Verfahren zur gleichzeitigen Herstellung und Gewinnung von Carbonsaeureanhydriden |
| FR1386278A (fr) | 1963-10-23 | 1965-01-22 | Distillers Co Yeast Ltd | Séparation des acides carbo-oxyliques |
| DE3726805A1 (de) | 1987-08-12 | 1989-02-23 | Basf Ag | Verfahren zur destillativen reinigung von tetrahydrofuran |
| CA1327812C (en) * | 1987-12-23 | 1994-03-15 | Thomas G. Attig | Vapor-phase hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone |
| JP2666151B2 (ja) * | 1988-12-14 | 1997-10-22 | 東燃株式会社 | １，４−ブタンジオールの製造法 |
| JP3206183B2 (ja) * | 1993-02-17 | 2001-09-04 | 三菱化学株式会社 | １，４−ブタンジオールの製造方法 |
| IT1298535B1 (it) * | 1998-02-02 | 2000-01-12 | Lonza Spa | Procedimento per la produzione di gamma-butirrolattone |
| AU1055701A (en) * | 1999-11-05 | 2001-06-06 | Asahi Kasei Kabushiki Kaisha | Process for the preparation of diol mixtures |
| DE10009817A1 (de) | 2000-03-01 | 2001-09-06 | Basf Ag | Verfahren zur Herstellung von Alkoholen an rheniumhaltigen Aktivkohle-Trägerkatalysatoren |
| DE10061556A1 (de) | 2000-12-11 | 2002-06-13 | Basf Ag | Verfahren zur Herstellung von Tetrahydrofuran |
| GB0117090D0 (en) | 2001-07-12 | 2001-09-05 | Kvaerner Process Tech Ltd | Process |
| JP2003113171A (ja) * | 2001-10-05 | 2003-04-18 | Nippon Shokubai Co Ltd | 無水コハク酸の精製方法 |
| DE10225929A1 (de) * | 2002-06-11 | 2003-12-24 | Basf Ag | Zweistufiges Verfahren zur Herstellung von Butandiol mit Zwischenabtrennung von Bernsteinsäureanhydrid |
| DE10357715A1 (de) * | 2003-12-09 | 2005-07-14 | Basf Ag | Verfahren zur Herstellung von definierten Gemischen aus THF, BDO und GBL durch Gasphasenhydierung |
| CN101195608B (zh) * | 2006-12-06 | 2011-05-11 | 上海焦化有限公司 | 一种分离四氢呋喃和1，4-丁二醇的方法和装置 |
| CN101307042B (zh) * | 2007-05-18 | 2011-04-20 | 中国石油化工股份有限公司 | 生产1,4-丁二醇并联产四氢呋喃、γ-丁内酯的方法 |
| EP2185682B1 (en) | 2007-08-17 | 2016-05-18 | Basf Se | Carboxylic acid producing member of the pasteurellaceae |
| BRPI0919388B1 (pt) * | 2008-09-29 | 2019-02-19 | Mitsubishi Chemical Corporation | Método para produzir ácido succínico derivado de recursos de biomassa |
| US8673598B2 (en) * | 2009-02-16 | 2014-03-18 | Basf Se | Microbial succinic acid producers and purification of succinic acid |
| JP5395453B2 (ja) * | 2009-02-16 | 2014-01-22 | Ｊｘ日鉱日石エネルギー株式会社 | 無段変速機油組成物 |
| KR101231615B1 (ko) | 2009-09-11 | 2013-02-08 | 한국화학연구원 | 탄소수 4 내지 6의 유기산으로부터 고리화된 화합물을 제조하는 방법 |
| US9464026B2 (en) * | 2012-12-20 | 2016-10-11 | Archer-Daniels Midland Company | Recovering and using carboxylic acids from a fermentation broth |
| AP2015008850A0 (en) * | 2013-05-17 | 2015-11-30 | Xyleco Inc | Processing biomass |
| MY182437A (en) | 2013-10-23 | 2021-01-25 | Basf Se | Method for the preparation of 1, 4-butane diol having an apha color index of less than 30 |
| WO2016008904A1 (en) | 2014-07-16 | 2016-01-21 | Basf Se | METHOD FOR PURIFYING RAW γ-BUTYROLACTONE |
| WO2016110520A1 (de) | 2015-01-09 | 2016-07-14 | Basf Se | Verfahren zur herstellung von bernsteinsäureanhydrid und hochreiner bernsteinsäure oder ihren estern oder amiden |
-
2016
- 2016-01-08 US US15/541,960 patent/US10308623B2/en active Active
- 2016-01-08 JP JP2017536245A patent/JP6716574B2/ja not_active Expired - Fee Related
- 2016-01-08 CA CA2972303A patent/CA2972303C/en active Active
- 2016-01-08 ES ES16700181T patent/ES2730109T3/es active Active
- 2016-01-08 WO PCT/EP2016/050245 patent/WO2016110556A1/de not_active Ceased
- 2016-01-08 EP EP16700181.7A patent/EP3242870B1/de active Active
- 2016-01-08 KR KR1020177021861A patent/KR20170102530A/ko not_active Ceased
- 2016-01-08 BR BR112017014623-1A patent/BR112017014623B1/pt not_active IP Right Cessation
- 2016-01-08 CN CN201680005106.8A patent/CN107108538B/zh active Active
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