JP5916506B2 - オレフィンの製造方法 - Google Patents
オレフィンの製造方法 Download PDFInfo
- Publication number
- JP5916506B2 JP5916506B2 JP2012106828A JP2012106828A JP5916506B2 JP 5916506 B2 JP5916506 B2 JP 5916506B2 JP 2012106828 A JP2012106828 A JP 2012106828A JP 2012106828 A JP2012106828 A JP 2012106828A JP 5916506 B2 JP5916506 B2 JP 5916506B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- mol
- secondary alcohol
- catalyst
- olefin
- 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.)
- Active
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 37
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 150000003333 secondary alcohols Chemical class 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000006297 dehydration reaction Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 10
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 10
- 239000011949 solid catalyst Substances 0.000 claims description 10
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical group CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 239000012895 dilution Substances 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000003054 catalyst Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 11
- 239000007789 gas Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 230000000737 periodic effect Effects 0.000 description 6
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229910052696 pnictogen Inorganic materials 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 1
- ACUZDYFTRHEKOS-SNVBAGLBSA-N 2-Decanol Natural products CCCCCCCC[C@@H](C)O ACUZDYFTRHEKOS-SNVBAGLBSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- GUHWHNUGIGOSCN-UHFFFAOYSA-N 4-Methyl-2-heptanol Chemical compound CCCC(C)CC(C)O GUHWHNUGIGOSCN-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- KZUBXUKRWLMPIO-UHFFFAOYSA-N 4-methylhexan-2-ol Chemical compound CCC(C)CC(C)O KZUBXUKRWLMPIO-UHFFFAOYSA-N 0.000 description 1
- GENRWSDYODERST-UHFFFAOYSA-N 4-methylnonan-2-ol Chemical compound CCCCCC(C)CC(C)O GENRWSDYODERST-UHFFFAOYSA-N 0.000 description 1
- FYMBAYNKBWGEIK-UHFFFAOYSA-N 5-methylheptan-2-ol Chemical compound CCC(C)CCC(C)O FYMBAYNKBWGEIK-UHFFFAOYSA-N 0.000 description 1
- ZDVJGWXFXGJSIU-UHFFFAOYSA-N 5-methylhexan-2-ol Chemical compound CC(C)CCC(C)O ZDVJGWXFXGJSIU-UHFFFAOYSA-N 0.000 description 1
- KZTLXVUOEODDMR-UHFFFAOYSA-N 5-methylnonan-2-ol Chemical compound CCCCC(C)CCC(C)O KZTLXVUOEODDMR-UHFFFAOYSA-N 0.000 description 1
- OYTRLQQQIHEJFE-UHFFFAOYSA-N 6-methylnonan-2-ol Chemical compound CCCC(C)CCCC(C)O OYTRLQQQIHEJFE-UHFFFAOYSA-N 0.000 description 1
- IBCSSJYUKOBWLB-UHFFFAOYSA-N 6-methyloctan-2-ol Chemical compound CCC(C)CCCC(C)O IBCSSJYUKOBWLB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LPTWGVWNFGQDPV-UHFFFAOYSA-N CC(CCC(C)O)CCC.CC(CC(C)O)CCCC Chemical compound CC(CCC(C)O)CCC.CC(CC(C)O)CCCC LPTWGVWNFGQDPV-UHFFFAOYSA-N 0.000 description 1
- -1 Ta 2 O 5 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012106828A JP5916506B2 (ja) | 2012-05-08 | 2012-05-08 | オレフィンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012106828A JP5916506B2 (ja) | 2012-05-08 | 2012-05-08 | オレフィンの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013234139A JP2013234139A (ja) | 2013-11-21 |
| JP2013234139A5 JP2013234139A5 (enExample) | 2015-06-18 |
| JP5916506B2 true JP5916506B2 (ja) | 2016-05-11 |
Family
ID=49760542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012106828A Active JP5916506B2 (ja) | 2012-05-08 | 2012-05-08 | オレフィンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5916506B2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014103898A1 (ja) * | 2012-12-26 | 2014-07-03 | 花王株式会社 | オレフィンの製造方法 |
| CN111530444B (zh) * | 2020-06-01 | 2023-10-27 | 四川泸天化股份有限公司 | 一种合成长链α-烯烃的催化剂及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1225559A (enExample) * | 1968-12-19 | 1971-03-17 | ||
| JPH07132225A (ja) * | 1993-11-10 | 1995-05-23 | Nissan Gaadoraa Shokubai Kk | 各種脱水反応用酸化ジルコニウム触媒の製造方法 |
| JPH09100244A (ja) * | 1995-10-03 | 1997-04-15 | Maruzen Petrochem Co Ltd | オレフィン類の製造方法およびこれに用いる脱水反応触媒 |
| EP1790627A1 (en) * | 2005-11-29 | 2007-05-30 | BP Chemicals Limited | Process for producing olefins |
| EP2585422B1 (en) * | 2010-06-23 | 2018-01-10 | Total Research & Technology Feluy | Dehydration of alcohols on poisoned acidic catalysts |
-
2012
- 2012-05-08 JP JP2012106828A patent/JP5916506B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013234139A (ja) | 2013-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6084963B2 (ja) | １，３−ブタジエンの製造方法 | |
| JP6082035B2 (ja) | 酢酸とジメチルエーテルを製造するプロセス | |
| RU2630675C2 (ru) | Катализатор и способ получения уксусной кислоты и диметилового эфира | |
| JP6909225B2 (ja) | オリゴシランの製造方法 | |
| US11136276B2 (en) | Single-stage method of butadiene production | |
| JP5820818B2 (ja) | オレフィン製造用触媒及びオレフィンの製造方法 | |
| WO2014199349A2 (en) | Metal impregnated amorphous silicates for the selective conversion of ethanol to butadiene | |
| JP6191696B2 (ja) | イソブチレンの製造方法、メタクリル酸の製造方法、およびメタクリル酸メチルの製造方法 | |
| JP5895705B2 (ja) | プロピレンの製造方法 | |
| EP2539304B1 (en) | Process for preparing an alkene | |
| JP5916506B2 (ja) | オレフィンの製造方法 | |
| JP6076477B2 (ja) | オレフィンの製造方法、およびこれに用いられる脱水触媒 | |
| JPWO2014129248A1 (ja) | エタノールから１，３−ブタジエンを選択的に製造する方法 | |
| AU2012220218B2 (en) | Method for producing ethylene glycol through fluidized bed catalytic reaction of oxalate | |
| JP2017530150A (ja) | ２，５−ジクロロフェノールの合成方法 | |
| US11717807B2 (en) | Method for producing conjugated diene | |
| TW201542512A (zh) | 不飽和烴之製造方法 | |
| US20120302810A1 (en) | Process for preparing an alkene | |
| KR20150058325A (ko) | 아이소뷰틸렌 제조용 촉매, 및 그것을 이용한 아이소뷰틸렌의 제조 방법 | |
| JP2017014133A (ja) | ホモアリルアルコールの製造方法 | |
| JP2020143017A (ja) | 末端二重結合含有化合物の製造方法 | |
| JP2010155183A (ja) | アクロレインの製造方法 | |
| KR102325331B1 (ko) | 터트-부탄올로부터 이소부틸렌의 제조방법 | |
| JP5724615B2 (ja) | エポキシ化合物の製造方法 | |
| TW202500541A (zh) | 半導體液體藥劑及半導體液體藥劑的製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20140812 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150423 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150423 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150907 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150929 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151127 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160322 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160405 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5916506 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |