KR20170102530A - 테트라히드로푸란, 1,4-부탄디올 또는 감마-부티로락톤의 제조 방법 - Google Patents
테트라히드로푸란, 1,4-부탄디올 또는 감마-부티로락톤의 제조 방법 Download PDFInfo
- Publication number
- KR20170102530A KR20170102530A KR1020177021861A KR20177021861A KR20170102530A KR 20170102530 A KR20170102530 A KR 20170102530A KR 1020177021861 A KR1020177021861 A KR 1020177021861A KR 20177021861 A KR20177021861 A KR 20177021861A KR 20170102530 A KR20170102530 A KR 20170102530A
- Authority
- KR
- South Korea
- Prior art keywords
- water
- process according
- succinic anhydride
- catalyst
- tetrahydrofuran
- 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.)
- Ceased
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 120
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 59
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 42
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims abstract description 32
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 114
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 64
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 64
- 239000001384 succinic acid Substances 0.000 claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
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- 230000004151 fermentation Effects 0.000 claims description 35
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- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 6
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- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
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- 239000012263 liquid product Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229940085127 phytase Drugs 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000701 toxic element Toxicity 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/207—1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| KR20170102530A true KR20170102530A (ko) | 2017-09-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177021861A Ceased KR20170102530A (ko) | 2015-01-09 | 2016-01-08 | 테트라히드로푸란, 1,4-부탄디올 또는 감마-부티로락톤의 제조 방법 |
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 |
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| 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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016110556A1 (de) | 2016-07-14 |
| EP3242870A1 (de) | 2017-11-15 |
| CN107108538B (zh) | 2020-10-27 |
| JP2018502857A (ja) | 2018-02-01 |
| BR112017014623A2 (pt) | 2018-02-06 |
| US10308623B2 (en) | 2019-06-04 |
| BR112017014623B1 (pt) | 2021-06-22 |
| CN107108538A (zh) | 2017-08-29 |
| CA2972303C (en) | 2023-06-20 |
| US20180002303A1 (en) | 2018-01-04 |
| ES2730109T3 (es) | 2019-11-08 |
| JP6716574B2 (ja) | 2020-07-01 |
| CA2972303A1 (en) | 2016-07-14 |
| EP3242870B1 (de) | 2019-03-13 |
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