JP2016117678A5 - - Google Patents
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- JP2016117678A5 JP2016117678A5 JP2014257897A JP2014257897A JP2016117678A5 JP 2016117678 A5 JP2016117678 A5 JP 2016117678A5 JP 2014257897 A JP2014257897 A JP 2014257897A JP 2014257897 A JP2014257897 A JP 2014257897A JP 2016117678 A5 JP2016117678 A5 JP 2016117678A5
- Authority
- JP
- Japan
- Prior art keywords
- furfural
- compound
- composition
- furan
- producing
- 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.)
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 24
- -1 furan compound Chemical class 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-Acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Chemical group O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000006606 decarbonylation reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000011949 solid catalyst Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
Description
即ち、本発明の要旨は、以下の［１］〜［７］に存する。
［１］原料としてフルフラール化合物を主成分として含むフルフラール組成物を反応器に
供給し、触媒の存在下で脱カルボニル化反応を行うことによりフラン化合物を製造する際
、該フルフラール組成物中の２−アセチルフラン濃度が１２０重量ｐｐｍ以上２０００重
量ｐｐｍ以下であることを特徴とするフラン化合物の製造方法。
［２］ 前記原料のフルフラール組成物のフルフラール化合物の濃度が９９．００重量％
〜９９．９５重量％である［１］に記載のフラン化合物の製造方法。
［３］前記触媒が、担体がジルコニアで、且つ担持金属がパラジウムを含む固体触媒であ
ることを特徴とする［１］又は［２］に記載のフラン化合物の製造方法。
［４］前記フルフラール組成物中の前記フルフラール化合物がフルフラールであって、以
下の工程（ａ）を更に有することを特徴とする上記［１］〜［３］のいずれか１に記載の
フラン化合物の製造方法。
（ａ） 粗フルフラールと陰イオン交換樹脂及び／又は塩基性化合物を接触させた後に、
得られる粗フルフラールを蒸留塔で蒸留し、フルフラールよりも高い沸点を有する化合物
及び／又はフルフラールよりも低い沸点を有する化合物を除去して、フルフラール組成物
を製造する工程
［５］［１］〜[４]のいずれか１に記載のフラン化合物の製造方法により得られるフラン
を触媒の存在下で水素化反応を行うことによりテトラヒドロフランを製造する、テトラヒ
ドロフランの製造方法。
［６］フルフラール化合物を主成分として含むフルフラール組成物であって、該組成物中
の２−アセチルフランの濃度が１２０重量ｐｐｍ以上２０００重量ｐｐｍ以下である、フ
ルフラール組成物。
［７］前記フルフラール化合物の濃度が９９．００重量％〜９９．９５重量％である［６
］に記載のフルフラール組成物。
That is, the gist of the present invention resides in the following [1] to [7].
[1] When producing a furan compound by supplying a furfural composition containing a furfural compound as a main component as a raw material to a reactor and performing a decarbonylation reaction in the presence of a catalyst, A method for producing a furan compound, wherein the acetylfuran concentration is 120 ppm by weight or more and 2000 ppm by weight or less.
[2] The concentration of the furfural compound in the raw furfural composition is 99.00% by weight.
The manufacturing method of the furan compound as described in [1] which is -99.95 weight%.
[3] The method for producing a furan compound according to [1] or [2], wherein the catalyst is a solid catalyst in which the carrier is zirconia and the supported metal includes palladium.
[4] The furfural compound in any one of the above [1] to [3], wherein the furfural compound in the furfural composition is furfural and further includes the following step (a): Production method.
(A) After contacting the crude furfural with an anion exchange resin and / or a basic compound,
The obtained crude furfural is distilled in a distillation column, and a compound having a boiling point higher than that of furfural and / or a compound having a boiling point lower than that of furfural is removed to produce a furfural composition [5] [1] to [ 4] A method for producing tetrahydrofuran, wherein tetrahydrofuran is produced by hydrogenating a furan obtained by the method for producing a furan compound according to any one of 4) in the presence of a catalyst.
[6] A furfural composition comprising a furfural compound as a main component, wherein the concentration of 2-acetylfuran in the composition is 120 ppm to 2000 ppm by weight.
[7] The concentration of the furfural compound is 99.00 wt% to 99.95 wt% [6]
] The furfural composition as described in above.
Claims (7)
し、触媒の存在下で脱カルボニル化反応を行うことによりフラン化合物を製造する際、該
フルフラール組成物中の２−アセチルフラン濃度が１２０重量ｐｐｍ以上２０００重量ｐ
ｐｍ以下であることを特徴とするフラン化合物の製造方法。 When producing a furan compound by supplying a furfural composition containing a furfural compound as a main component as a raw material to a reactor and performing a decarbonylation reaction in the presence of a catalyst, the concentration of 2-acetylfuran in the furfural composition Is 120ppm by weight or more and 2000wtp
The manufacturing method of the furan compound characterized by being below pm.
．９５重量％である請求項１に記載のフラン化合物の製造方法。 The concentration of the furfural compound in the raw furfural composition is 99.00% by weight to 99%.
. The method for producing a furan compound according to claim 1, which is 95% by weight.
とを特徴とする請求項１又は２に記載のフラン化合物の製造方法。 The method for producing a furan compound according to claim 1 or 2, wherein the catalyst is a solid catalyst in which the carrier is zirconia and the supported metal contains palladium.
工程（ａ）を更に有することを特徴とする請求項１〜３のいずれか1項に記載のフラン化
合物の製造方法。
（ａ） 粗フルフラールと陰イオン交換樹脂及び／又は塩基性化合物を接触させた後に、
得られる粗フルフラールを蒸留塔で蒸留し、フルフラールよりも高い沸点を有する化合物
及び／又はフルフラールよりも低い沸点を有する化合物を除去して、フルフラール組成物
を製造する工程 The said furfural compound in the said furfural composition is a furfural, Comprising: It further has the following process (a), The manufacturing method of the furan compound of any one of Claims 1-3 characterized by the above-mentioned.
(A) After contacting the crude furfural with an anion exchange resin and / or a basic compound,
A step of producing a furfural composition by distilling the resulting crude furfural in a distillation column and removing a compound having a boiling point higher than that of furfural and / or a compound having a boiling point lower than that of furfural.
触媒の存在下で水素化反応を行うことによりテトラヒドロフランを製造する、テトラヒド
ロフランの製造方法。 The manufacturing method of tetrahydrofuran which manufactures tetrahydrofuran by hydrogenating the furan obtained by the manufacturing method of the furan compound of any one of Claims 1-4 in presence of a catalyst.
−アセチルフランの濃度が１２０重量ｐｐｍ以上２０００重量ｐｐｍ以下である、フルフ
ラール組成物。 A furfural composition comprising a furfural compound as a main component, wherein 2 in the composition
-The furfural composition whose concentration of acetyl furan is 120 weight ppm or more and 2000 weight ppm or less.
に記載のフルフラール組成物。 The concentration of the furfural compound is 99.00 wt% to 99.95 wt%.
A furfural composition as described in 1. above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014257897A JP2016117678A (en) | 2014-12-19 | 2014-12-19 | Manufacturing method of furan compound and manufacturing method of tetrahydrofuran |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014257897A JP2016117678A (en) | 2014-12-19 | 2014-12-19 | Manufacturing method of furan compound and manufacturing method of tetrahydrofuran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016117678A JP2016117678A (en) | 2016-06-30 |
| JP2016117678A5 true JP2016117678A5 (en) | 2017-10-19 |
Family
ID=56243719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014257897A Pending JP2016117678A (en) | 2014-12-19 | 2014-12-19 | Manufacturing method of furan compound and manufacturing method of tetrahydrofuran |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2016117678A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111548333B (en) * | 2020-05-28 | 2022-08-30 | 陕西延长石油（集团）有限责任公司 | Method for preparing delta-valerolactone |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5315679B2 (en) * | 2007-11-30 | 2013-10-16 | 三菱化学株式会社 | Method for producing furan compound |
| JP5375054B2 (en) * | 2007-11-30 | 2013-12-25 | 三菱化学株式会社 | Method for producing furan compound |
| AU2009327449B2 (en) * | 2008-12-18 | 2015-12-24 | Covation Inc. | Vapor phase decarbonylation process |
| BRPI0914400A2 (en) * | 2008-12-18 | 2015-08-04 | Du Pont | "process for the synthesis of a compound" |
| BR112012004397B1 (en) * | 2009-08-31 | 2021-03-30 | E.I. Du Pont De Nemours And Company | PROCESS TO SYNTHESIZE A COMPOUND |
| AU2010286449B2 (en) * | 2009-08-31 | 2016-06-23 | Covation Inc. | Vapor phase decarbonylation process |
| US8653287B2 (en) * | 2009-08-31 | 2014-02-18 | E I Du Pont De Nemours And Company | Decarbonylation process |
| JP5948921B2 (en) * | 2012-02-08 | 2016-07-06 | 三菱化学株式会社 | Production method of furan |
| JP6299086B2 (en) * | 2012-06-08 | 2018-03-28 | 三菱ケミカル株式会社 | Method for purifying furfural |
| JP2013253061A (en) * | 2012-06-08 | 2013-12-19 | Mitsubishi Chemicals Corp | Method for purifying furfural and method for producing furan |
| US9333493B2 (en) * | 2012-10-23 | 2016-05-10 | Shell Oil Company | Regeneration of aldehyde decarbonylation catalysts |
| US9650354B2 (en) * | 2013-06-25 | 2017-05-16 | Council Of Scientific & Industrial Research | Process for producing furan and its derivatives |
| JP2015140311A (en) * | 2014-01-28 | 2015-08-03 | 国立大学法人九州大学 | Method for producing furan compound |
| JP6575126B2 (en) * | 2014-05-08 | 2019-09-18 | 三菱ケミカル株式会社 | Method for producing furfural and method for producing furan |
-
2014
- 2014-12-19 JP JP2014257897A patent/JP2016117678A/en active Pending
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