JP2002361086A5 - - Google Patents
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- JP2002361086A5 JP2002361086A5 JP2001167740A JP2001167740A JP2002361086A5 JP 2002361086 A5 JP2002361086 A5 JP 2002361086A5 JP 2001167740 A JP2001167740 A JP 2001167740A JP 2001167740 A JP2001167740 A JP 2001167740A JP 2002361086 A5 JP2002361086 A5 JP 2002361086A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- acid ester
- aldehydes
- producing
- inorganic oxide
- 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.)
- Pending
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- 150000001733 carboxylic acid esters Chemical class 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052809 inorganic oxide Inorganic materials 0.000 description 4
- -1 aliphatic aldehydes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atoms Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000002194 synthesizing Effects 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 229910052803 cobalt Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N 4-Anisaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N 4-Methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N Glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 229940015043 Glyoxal Drugs 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N Phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Description
【特許請求の範囲】
【請求項１】
平均粒子径６ｎｍ以下の金超微粒子が無機酸化物担体上に担持されているカルボン酸エステル合成用触媒と酸素の存在下に、アルデヒドとアルコールを反応させることを特徴とするカルボン酸エステルの製造方法であって、
（１）該無機酸化物担体が、Ｍｇ、Ｃａ、Ｓｒ、Ｂａ、Ａｌ、Ｓｉ、Ｔｉ、Ｖ、Ｃｒ、Ｍｎ、Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ、Ｚｎ、Ｚｒ、Ｎｂ、Ｓｎ、Ｐｂ、Ｌａ及びＣｅの少なくとも１種の元素を含む酸化物からなり、
（２）該反応が、液相反応である、
カルボン酸エステルの製造方法。
【請求項２】
無機酸化物担体が、Ｍｇ、Ｃａ、Ｓｒ、Ｂａ、Ａｌ、Ｔｉ、Ｖ、Ｃｒ、Ｍｎ、Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ、Ｚｎ、Ｚｒ、Ｎｂ、Ｓｎ、Ｐｂ、Ｌａ及びＣｅの少なくとも１種とＳｉとを含む酸化物からなる請求項１記載のカルボン酸エステルの製造方法。
【請求項３】
カルボン酸エステル合成用触媒が、金を含む水溶性化合物の水溶液と無機酸化物担体とを混合した後、回収された固形分を焼成することによって得られるものである、請求項１又は２に記載のカルボン酸エステルの製造方法。
【請求項４】
アルデヒドが脂肪族アルデヒドおよびα、β−不飽和アルデヒドから選ばれる少なくとも一種であり、アルコールが炭素数１〜１０の脂肪族アルコールである、請求項１〜３のいずれかに記載のカルボン酸エステルの製造方法。
【請求項５】
請求項１〜４のいずれかに記載のカルボン酸エステルの製造方法に用いるカルボン酸エステル合成用触媒。
[Claims]
[Claim 1 ]
A method for producing a carboxylic acid ester, comprising reacting an aldehyde with an alcohol in the presence of oxygen and a carboxylic acid ester synthesis catalyst in which ultrafine gold particles having an average particle diameter of 6 nm or less are supported on an inorganic oxide carrier. And
(1) The inorganic oxide carrier is composed of Mg, Ca, Sr, Ba, Al, Si, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Zr, Nb, Sn, Pb, La and An oxide containing at least one element of Ce,
(2) the reaction is a liquid phase reaction;
A method for producing a carboxylic acid ester .
[Claim 2 ]
The inorganic oxide carrier is composed of at least one of Mg, Ca, Sr, Ba, Al, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Zr, Nb, Sn, Pb, La and Ce. 2. The method for producing a carboxylic acid ester according to claim 1, comprising an oxide containing Si.
[Claim 3 ]
Catalyst for carboxylic acid ester synthesis, after mixing the aqueous solution and an inorganic oxide support of a water-soluble compound containing gold, is obtained by firing the solid recovered, according to claim 1 or 2 A method for producing a carboxylic acid ester .
(4)
The carboxylic acid ester according to any one of claims 1 to 3, wherein the aldehyde is at least one selected from aliphatic aldehydes and α, β-unsaturated aldehydes, and the alcohol is an aliphatic alcohol having 1 to 10 carbon atoms. Production method.
(5)
A catalyst for carboxylic acid ester synthesis used in the method for producing a carboxylic acid ester according to claim 1.
上記アルデヒドとしては、例えばホルムアルデヒド、アセトアルデヒド、プロピオンアルデヒド、イソブチルアルデヒド、グリオキザール、ピルバルデヒド等の炭素数１〜１０の脂肪族アルデヒド；アクロレイン、メタクロレイン、クロトンアルデヒド等の炭素数３〜１０のα、β−不飽和アルデヒド；ベンズアルデヒド、ｐ−メトキシベンズアルデヒド、トルアルデヒド、フタルアルデヒド等の炭素数６〜２０の芳香族アルデヒド等のほか、これらアルデヒドの誘導体が挙げられる。好ましくは、脂肪族アルデヒド、α、β−不飽和アルデヒド等が使用できる。これらアルデヒドは、１種又は２種以上で用いることができる。 Examples of the aldehyde include aliphatic aldehydes having 1 to 10 carbon atoms, such as formaldehyde, acetaldehyde, propionaldehyde, isobutyraldehyde, glyoxal, and pyruvalaldehyde; Unsaturated aldehydes; examples thereof include aromatic aldehydes having 6 to 20 carbon atoms such as benzaldehyde , p -methoxybenzaldehyde, tolualdehyde, and phthalaldehyde, and derivatives of these aldehydes. Preferably, aliphatic aldehydes, α, β-unsaturated aldehydes and the like can be used. These aldehydes can be used alone or in combination of two or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001167740A JP2002361086A (en) | 2001-06-04 | 2001-06-04 | Carboxylic acid ester synthesis catalyst and method for producing carboxylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001167740A JP2002361086A (en) | 2001-06-04 | 2001-06-04 | Carboxylic acid ester synthesis catalyst and method for producing carboxylic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002361086A JP2002361086A (en) | 2002-12-17 |
| JP2002361086A5 true JP2002361086A5 (en) | 2008-03-21 |
Family
ID=19010082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001167740A Pending JP2002361086A (en) | 2001-06-04 | 2001-06-04 | Carboxylic acid ester synthesis catalyst and method for producing carboxylic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002361086A (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4513372B2 (en) * | 2004-03-23 | 2010-07-28 | 日産自動車株式会社 | Exhaust gas purification catalyst and exhaust gas purification catalyst |
| JP4513384B2 (en) | 2004-03-31 | 2010-07-28 | 日産自動車株式会社 | High heat-resistant exhaust gas purification catalyst and method for producing the same |
| JP2007275854A (en) * | 2006-04-12 | 2007-10-25 | Asahi Kasei Chemicals Corp | Carboxylate production catalyst excellent in reaction stability and method for producing carboxylate |
| BRPI0815166A8 (en) | 2007-08-13 | 2016-12-20 | Asahi Kasei Chemicals Corp | CATALYST FOR USE IN THE PRODUCTION OF CARBOXYL ACID ESTER, PROCESSES FOR PRODUCING THE SAME, AND, FOR PRODUCING CARBOXYL ACID ESTER |
| WO2009054462A1 (en) | 2007-10-26 | 2009-04-30 | Asahi Kasei Chemicals Corporation | Composite particle-loaded article, method for producing the composite particle-loaded article, and method for producing compound using the composite particle-loaded article as chemical synthesis catalyst |
| JP5580613B2 (en) * | 2010-02-05 | 2014-08-27 | 独立行政法人科学技術振興機構 | Production of asymmetric esters using polymer-supported gold cluster catalysts |
| WO2016113106A1 (en) * | 2015-01-16 | 2016-07-21 | Evonik Röhm Gmbh | Gold-based catalyst for the oxidative esterification of aldehydes to obtain carboxylic esters |
| WO2019022885A1 (en) * | 2017-07-28 | 2019-01-31 | Dow Global Technologies Llc | Method for preparation of heterogeneous catalysts |
| CN109821530B (en) * | 2017-11-23 | 2022-01-04 | 中国科学院大连化学物理研究所 | Cobalt-based catalyst and method for applying cobalt-based catalyst to propylene epoxidation reaction |
| CN109821529B (en) * | 2017-11-23 | 2022-02-01 | 中国科学院大连化学物理研究所 | Cobalt-based catalyst and method for preparing unsaturated carboxylic ester by using cobalt-based catalyst |
| US11111204B2 (en) | 2018-01-10 | 2021-09-07 | Dow Global Technologies Llc | Method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst |
| CN112165987B (en) * | 2018-06-28 | 2024-05-17 | 陶氏环球技术有限责任公司 | Heterogeneous catalyst |
| CN109772345B (en) * | 2019-01-05 | 2022-03-04 | 山东理工大学 | Preparation of nickel catalyst for synthesizing ester by aldehyde oxidation esterification and application of nickel catalyst and ionic liquid co-catalysis system |
| KR20210139189A (en) | 2020-05-13 | 2021-11-22 | 주식회사 엘지화학 | Catalyst for oxidative esterification reaction and method for manufacturing thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3818783B2 (en) * | 1998-11-19 | 2006-09-06 | 三井化学株式会社 | Method for producing carboxylic acid ester |
-
2001
- 2001-06-04 JP JP2001167740A patent/JP2002361086A/en active Pending
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