JP6553084B2 - エタノールの酸触媒脱水方法 - Google Patents
エタノールの酸触媒脱水方法 Download PDFInfo
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- JP6553084B2 JP6553084B2 JP2016561075A JP2016561075A JP6553084B2 JP 6553084 B2 JP6553084 B2 JP 6553084B2 JP 2016561075 A JP2016561075 A JP 2016561075A JP 2016561075 A JP2016561075 A JP 2016561075A JP 6553084 B2 JP6553084 B2 JP 6553084B2
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- ethanol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/04—Ethylene
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
-
- 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
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/08—Ethanol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/46—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/06—Diethyl ether
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- 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
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
(a)少なくとも1種の窒素含有汚染物質を含むエタノール原料(101)を蒸留して、塔頂流(102)、及びエタノールを含む塔底流(103)を形成するステップであって、蒸留の還流比が少なくとも20:1であるステップと、
(b)酸触媒の存在下で塔底流を反応させて、エチレン及び/又はジエチルエーテルを含む、生成物流を形成するステップと
を含む、エタノールの酸触媒脱水方法に関する。記載される別法として、本発明は、
(i)少なくとも1種の窒素含有汚染物質を含むエタノール原料(101)を蒸留し、塔頂流(102)、及びエタノールを含む塔底流(103)を形成するステップと、
(ii)塔頂流を凝縮し、凝縮流(104)及び気体流(105)を形成するステップと、
(iii)凝縮流の第一の部分をステップ(i)に還流液流(106)として戻し、かつ凝縮流の第二の部分を蒸留物流(107)として取り除くステップであって、取り除かれる蒸留物流の速度に対する戻される還流液流の速度の比である還流比が、少なくとも20:1であるステップと、
(iv)酸触媒の存在下で塔底流を反応させ、エチレン及び/又はジエチルエーテルを含む、生成物流を形成するステップと
を含む、エタノールの酸触媒脱水方法に関する。
・供給流101を予熱するための予備熱源、例えば蒸留ステップよりも上流又は下流プロセスからの予備熱の利用
・リボイラ用途としての予備熱源の利用
・供給流101などの別の流れとの熱交換における、生成物流109の熱源としての利用
・リボイラ用途としての、(高圧凝縮物から生じる)フラッシュ流の利用
が挙げられるが、これらに制限されない。
Claims (15)
- エタノールの酸触媒脱水方法であって、
(a)少なくとも1種の窒素含有汚染物質を含むエタノール原料(101)を蒸留して、塔頂流(102)、及びエタノールを含む塔底流(103)を形成するステップであって、前記蒸留の還流比が100:1〜2000:1の範囲であるステップと、
(b)酸触媒の存在下で前記塔底流を反応させて、エチレン及び/又はジエチルエーテルを含む、生成物流を形成するステップと
を含み、前記窒素含有汚染物質が、アセトニトリルを含むか、又はアセトニトリルであり、前記エタノール原料が、50ppmw以下の窒素を含有する、前記方法。 - エタノール原料を蒸留するステップが、500:1〜1500:1の還流比で行われる、請求項1に記載の方法。
- エタノール原料を蒸留するステップが、0.02bara〜2bara未満の圧力で行われる、請求項1又は2に記載の方法。
- エタノール原料を蒸留するステップが、0.2bara〜0.6baraの圧力で行われる、請求項3に記載の方法。
- 塔底流をリボイラ(203)に移して、蒸発流(108)及び生成物流(109)を形成するステップをさらに含み、前記生成物流がステップ(b)中の前記塔底流と置き換わる、請求項1〜4のいずれかに記載の方法。
- 蒸発流の少なくとも一部がステップ(a)に再循環される、請求項5に記載の方法。
- エタノール原料が、塔頂流及び塔底流がステップ(a)を出る位置の中間の位置でステップ(a)に導入される、請求項1〜6のいずれかに記載の方法。
- ステップ(a)の前に、エタノール原料に水を添加するステップをさらに含む、請求項1〜7のいずれかに記載の方法。
- 添加される水の量が、エタノール原料の0.01重量%〜5重量%である、請求項8に記載の方法。
- 酸触媒が、ヘテロポリ酸を含む、請求項1〜9のいずれかに記載の方法。
- 酸触媒が、ケイ酸塩を含む、請求項1〜10のいずれかに記載の方法。
- エタノール原料がバイオエタノールを含むか、又はエタノール原料がバイオエタノール原料である、請求項1〜11のいずれかに記載の方法。
- エタノール原料を吸着剤に接触させるステップをさらに含み、前記エタノール原料が液相又は気相にある、請求項1〜12のいずれかに記載の方法。
- エタノールからエチレンに酸触媒脱水するためのエタノール原料の調製方法であって、前記方法が、少なくとも1種の窒素含有汚染物質を含むエタノール原料(101)を蒸留するステップを含み、前記蒸留の還流比が100:1〜2000:1の範囲であり、前記エタノール原料が前記蒸留ステップから塔底流で流出し、前記窒素含有汚染物質が、アセトニトリルを含むか又はアセトニトリルであり、前記エタノール原料が、50ppmw以下の窒素を含有する、前記方法。
- 窒素含有汚染物質が枯渇したエタノール原料を、酸触媒の存在下で脱水して、エチレン及び/又はジエチルエーテルを生成するための、請求項1〜13のいずれかに記載の方法の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13199602.7 | 2013-12-24 | ||
EP13199602 | 2013-12-24 | ||
PCT/EP2014/078853 WO2015097100A2 (en) | 2013-12-24 | 2014-12-19 | Process for the acid-catalysed dehydration of ethanol |
Publications (2)
Publication Number | Publication Date |
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JP2017507167A JP2017507167A (ja) | 2017-03-16 |
JP6553084B2 true JP6553084B2 (ja) | 2019-07-31 |
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Application Number | Title | Priority Date | Filing Date |
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JP2016561075A Active JP6553084B2 (ja) | 2013-12-24 | 2014-12-19 | エタノールの酸触媒脱水方法 |
Country Status (19)
Country | Link |
---|---|
US (1) | US9828319B2 (ja) |
EP (1) | EP3087047B1 (ja) |
JP (1) | JP6553084B2 (ja) |
KR (1) | KR102371111B1 (ja) |
CN (1) | CN106132911B (ja) |
AR (1) | AR098923A1 (ja) |
AU (1) | AU2014372702B2 (ja) |
BR (1) | BR112016014938B1 (ja) |
CA (1) | CA2935000C (ja) |
DK (1) | DK3087047T3 (ja) |
ES (1) | ES2672006T3 (ja) |
MX (1) | MX368632B (ja) |
MY (1) | MY171559A (ja) |
RU (1) | RU2016130011A (ja) |
SG (1) | SG11201605227WA (ja) |
TR (1) | TR201806937T4 (ja) |
TW (1) | TWI647212B (ja) |
WO (1) | WO2015097100A2 (ja) |
ZA (1) | ZA201604268B (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111774051A (zh) * | 2020-06-02 | 2020-10-16 | 贵州理工学院 | 光热催化醇类脱水制乙烯和有机产物的催化剂及制备方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4018562A (en) | 1975-10-24 | 1977-04-19 | Antek Instruments, Inc. | Chemiluminescent nitrogen detection apparatus and method |
EP0001681A1 (en) * | 1977-10-06 | 1979-05-02 | BP Chemicals Limited | Dehydration of alcohols, preferably ethanol, using a cyclohexane entrainer |
DE53917T1 (de) * | 1980-12-06 | 1983-07-21 | Bp Chemicals Ltd., London | Verfahren zur herstellung eines aethanol-wasser-azeotrops aus rohaethanol. |
US5415741A (en) * | 1994-10-18 | 1995-05-16 | Lloyd Berg | Separation of ethanol from isopropanol by azeotropic distillation |
AU3143797A (en) | 1996-05-30 | 1998-01-05 | Phillips Petroleum Company | Process for removing nitrile in etherification process |
FR2812289B1 (fr) | 2000-07-26 | 2003-08-22 | Total Raffinage Distribution | Procede et dispositif d'etherification d'olefines d'une charge d'hydrocarbures et leur utilisation |
US6503956B2 (en) | 2001-01-11 | 2003-01-07 | Chevron U.S.A. Inc. | Determination of heteroatom content in Fischer-Tropsch wax |
US6770790B1 (en) | 2003-10-17 | 2004-08-03 | Arco Chemical Technology, L.P. | Purification of tertiary butyl alcohol |
EP1792885A1 (en) * | 2005-11-29 | 2007-06-06 | BP Chemicals Limited | Process for producing ethylene |
EP2089156B1 (en) | 2006-11-22 | 2022-01-05 | Technip E&C Limited | Process for producing alkenes from oxygenates by using supported heteropolyacid catalysts |
EP1992601A1 (en) * | 2007-05-11 | 2008-11-19 | Ineos Europe Limited | Dehydration of alcohols over supported heteropolyacids |
CN104761427A (zh) | 2008-02-07 | 2015-07-08 | 道达尔研究技术弗吕公司 | 醇在结晶硅酸盐上的脱水 |
WO2010060981A1 (en) * | 2008-11-28 | 2010-06-03 | Total Petrochemicals Research Feluy | Purification of alcohols prior to their use in the presence of an acid catalyst |
US9139929B2 (en) | 2010-01-22 | 2015-09-22 | Total Research & Technology Feluy | Dehydration of alcohols on a crystalline silicate of low Si/Al ratio |
-
2014
- 2014-12-11 TW TW103143284A patent/TWI647212B/zh active
- 2014-12-19 KR KR1020167018669A patent/KR102371111B1/ko active IP Right Grant
- 2014-12-19 AU AU2014372702A patent/AU2014372702B2/en active Active
- 2014-12-19 BR BR112016014938A patent/BR112016014938B1/pt active IP Right Grant
- 2014-12-19 ES ES14816268.8T patent/ES2672006T3/es active Active
- 2014-12-19 MX MX2016008450A patent/MX368632B/es active IP Right Grant
- 2014-12-19 WO PCT/EP2014/078853 patent/WO2015097100A2/en active Application Filing
- 2014-12-19 RU RU2016130011A patent/RU2016130011A/ru unknown
- 2014-12-19 DK DK14816268.8T patent/DK3087047T3/en active
- 2014-12-19 CN CN201480076222.XA patent/CN106132911B/zh active Active
- 2014-12-19 TR TR2018/06937T patent/TR201806937T4/tr unknown
- 2014-12-19 EP EP14816268.8A patent/EP3087047B1/en active Active
- 2014-12-19 JP JP2016561075A patent/JP6553084B2/ja active Active
- 2014-12-19 SG SG11201605227WA patent/SG11201605227WA/en unknown
- 2014-12-19 CA CA2935000A patent/CA2935000C/en active Active
- 2014-12-19 US US15/108,234 patent/US9828319B2/en active Active
- 2014-12-19 MY MYPI2016001175A patent/MY171559A/en unknown
- 2014-12-22 AR ARP140104867A patent/AR098923A1/es unknown
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2016
- 2016-06-23 ZA ZA2016/04268A patent/ZA201604268B/en unknown
Also Published As
Publication number | Publication date |
---|---|
KR20160124081A (ko) | 2016-10-26 |
AU2014372702B2 (en) | 2019-03-07 |
CA2935000A1 (en) | 2015-07-02 |
US9828319B2 (en) | 2017-11-28 |
CN106132911A (zh) | 2016-11-16 |
AR098923A1 (es) | 2016-06-22 |
EP3087047B1 (en) | 2018-04-25 |
BR112016014938B1 (pt) | 2020-04-14 |
RU2016130011A (ru) | 2018-01-30 |
MX2016008450A (es) | 2017-01-11 |
BR112016014938A2 (pt) | 2018-01-23 |
KR102371111B1 (ko) | 2022-03-07 |
TWI647212B (zh) | 2019-01-11 |
EP3087047A2 (en) | 2016-11-02 |
AU2014372702A1 (en) | 2016-07-14 |
JP2017507167A (ja) | 2017-03-16 |
WO2015097100A2 (en) | 2015-07-02 |
US20160326080A1 (en) | 2016-11-10 |
TW201529552A (zh) | 2015-08-01 |
ES2672006T3 (es) | 2018-06-12 |
MX368632B (es) | 2019-10-09 |
SG11201605227WA (en) | 2016-08-30 |
ZA201604268B (en) | 2017-07-26 |
CN106132911B (zh) | 2019-06-18 |
CA2935000C (en) | 2021-08-03 |
DK3087047T3 (en) | 2018-06-18 |
WO2015097100A3 (en) | 2015-11-26 |
MY171559A (en) | 2019-10-18 |
TR201806937T4 (tr) | 2018-06-21 |
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