CN111039763A - Process for preparing saturated homopolyethers from unsaturated carbonyl compounds - Google Patents
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- CN111039763A CN111039763A CN201910720934.5A CN201910720934A CN111039763A CN 111039763 A CN111039763 A CN 111039763A CN 201910720934 A CN201910720934 A CN 201910720934A CN 111039763 A CN111039763 A CN 111039763A
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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
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The present invention provides a method for efficiently producing a saturated homopolyether from an unsaturated carbonyl compound. The process for producing a saturated homopolyether uses an unsaturated carbonyl compound and hydrogen as raw materials, and uses a catalyst in which a metal is supported on an acidic catalyst carrier. Here, the metal of the catalyst is, for example, palladium, and the carrier of the catalyst is alumina, silica-alumina, or the like. The unsaturated carbonyl compound as a raw material is 2-butenal, 2-ethyl-2-hexenal, 2-ethyl-2-butenal, 2-hexenal or the like, and the saturated homopolyether produced is dibutyl ether, bis (2-ethylhexyl) ether, bis (2-ethylbutyl) ether, dihexyl ether or the like.
Description
Technical Field
The present invention relates to a method for preparing saturated polyether from unsaturated carbonyl compound, and the unsaturated carbonyl compound and hydrogen are reacted under the condition of double-function catalyst which has metal catalyst function and acid catalyst function.
Background
The higher saturated homopolyether has special physical properties that are not present in alkanes such as low viscosity, high flash point, and low pour point, and is used as a base oil for hydraulic working oil by utilizing the characteristic that the penetration into a sealing rubber used for a seal is small (non-patent document 1). The saturated homopolyether is usually produced by two-stage reactions, i.e., dehydration dimerization of an alcohol with an acid catalyst or a two-stage reaction from an aldehyde via a (hemi) acetal. The dehydration dimerization of alcohols by an acid catalyst is generally a reaction carried out by an inorganic acid such as sulfuric acid or hydrochloric acid as a protonic acid or a solid acid catalyst such as silica-alumina or Nafion (non-patent document 2), and although the reaction is simple, there is a problem that an increase in the selectivity of a target substance is prevented because a large amount of olefin is produced as a by-product by intramolecular dehydration. On the other hand, since two raw materials, aldehyde and alcohol, are used in the method via acetal, in the case of producing ether having different both ends, the method via (hemi) acetal is a preferable method, but even if polyether having the same group at both ends is produced, after the (hemi) acetal is formed and vinyl ether is produced, vinyl group must be reacted under pressure in the presence of hydrogen and a hydrogenation catalyst, and in addition to the complicated steps, two raw materials, aldehyde and alcohol, must be prepared, which causes a problem of an increase in equipment investment. For example, patent document 1 discloses a method for producing an ether compound, which is characterized in that: a specific carbonyl compound and a specific hydroxyl compound are reacted in a hydrogen atmosphere using a palladium catalyst supported on carbon powder. Examples of the above documents disclose the use of 5% Pd-zeolite (example 5), 5% Pd-silica alumina (example 6) and 5% Pd-alumina (example 7) as catalysts, but they do not disclose polyether compounds at all and are not satisfactory in terms of the separation yield. Patent document 2 discloses a method for producing an ether compound, which includes a step of reacting a hydroxyl compound and/or a carbonyl compound with a catalyst in a hydrogen atmosphere to obtain a reaction product containing an ether compound.
Regarding chemicals produced by so-called mass production, since the production steps and the amount of the raw material species are directly reacted in terms of cost, it is required to shorten the reaction steps as much as possible. That is, it was found that, when a product is produced through a multi-stage process, it is extremely effective to use a compound in a previous stage as a raw material and produce the product in fewer raw material species and in shorter steps in order to reduce production costs. For example, when bis (2-ethylhexyl) ether, which is a saturated homopolyether, is produced, a general production method is to use 2-ethylhexanol, which is a saturated alcohol and 2-ethylhexanal (2-Ethyl hexonal), which is a saturated aldehyde, which are industrially produced in large quantities, as raw materials, and to produce the polyether by the following reaction.
(1) 2-ethylhexanol + 2-ethylhexanol → hemiacetal
(2) Hemiacetal → vinyl ether + water
(3) Vinyl Ether + Hydrogen → bis (2-ethylhexyl) Ether (saturated homopolyether)
Here, 2-ethylhexanol is produced by hydrogenating 2-ethylhexenal produced by aldol condensation of butylaldehyde, which is a raw material in the previous stage.
(4) Butyraldehyde → butyl aldol
(5) Butyl hydroxyaldehyde → 2-ethyl-2-hexenal + water
(6) 2-Ethyl-2-hexenal + Hydrogen → 2-ethylhexanol
Here, if di (2-ethylhexyl) ether can be produced using only 2-ethylhexenal, which is a compound in the previous stage of 2-ethylhexanol, as a raw material, the production steps of saturated ether can be shortened to achieve an extremely efficient production method of saturated homopolyether, but the above-mentioned document does not disclose such an efficient production method.
In addition to this, there are also disclosed: a method for producing an ether compound (patent document 3), characterized by reacting a hydroxyl compound with a carbonyl compound in a hydrogen atmosphere in the presence of a Lewis acid using a catalyst; a process for producing an ether (patent document 4) in which a cyclic acetal is reacted with hydrogen in the presence of a palladium catalyst supported on a mesoporous aluminosilicate; a method for producing an ether (patent document 5) or the like, in which a palladium catalyst supported on a mesoporous aluminosilicate is used as a catalyst in producing an ether by reacting a hydroxyl compound with a carbonyl compound in the presence of a catalyst in a hydrogen atmosphere; however, in either production method, even when homopolyethers having the same group at both ends are produced, the aldehyde and the alcohol are used as raw materials, and it is inevitable to make the supply of the raw materials complicated.
[ Prior art documents ]
[ patent document ]
[ patent document 1] Japanese patent laid-open No. 09-087223
[ patent document 2] Japanese patent laid-open No. 2000-038364
[ patent document 3] Japanese patent laid-open No. 09-040593
[ patent document 4] Japanese patent laid-open No. 2001-190954
[ patent document 5] Japanese patent laid-open No. 2000-281610
[ non-patent document ]
[ non-patent document 1] journal of Petroleum institute, vol.31, page 448 (1988)
[ non-patent document 2] Catalysis Letters 46(1997)1 to 4
Disclosure of Invention
[ problems to be solved by the invention ]
The present invention has been made to solve the above-mentioned conventional technical problems, and an object of the present invention is to provide a method for efficiently producing a saturated homopolyether from an unsaturated carbonyl compound.
[ means for solving the problems ]
The present inventors have made extensive studies and as a result, have found that a saturated homopolyether is efficiently produced from an unsaturated carbonyl compound and hydrogen by using a catalyst in which a metal is supported on an acidic catalyst support, and have completed the present invention.
The present invention encompasses a process for the production of saturated homopolyethers.
The process for producing a saturated homopolyether of the present invention is defined by the following items [1] to [9 ].
[1] A process for producing a saturated homopolyether, which comprises using an unsaturated carbonyl compound and hydrogen as raw materials and using a catalyst comprising a metal supported on an acidic catalyst carrier.
[2] The process for producing a saturated homopolyether according to item [1], wherein the unsaturated carbonyl compound is an aldehyde represented by formula (1), and a compound represented by formula (2) is produced;
in the formulae (1) and (2), R1、R2And R3Independently hydrogen, alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkynyl with 2-20 carbon atoms, cycloalkyl with 5-20 membered ring, aryl with 5-20 membered ring or heterocycle with 5-20 membered ring, wherein at least one carbon in the groups can be replaced by oxygen or sulfur, at least one-CH can be replaced by-N, and at least one > CH2May be substituted by > C ═ O, and further at least one hydrogen may be substituted by fluorine, chlorine, iodine or hydroxyl.
[3]According to item [2]The saturated homopolyether is produced by a process wherein R is represented by the following formulae (1) and (2)1、R2And R3Independently hydrogen, a C1-20 linear alkyl group, a C3-20 branched alkyl group, a C2-20 linear alkenyl group, or a C4-20 branched alkenyl group, wherein at least one carbon in these groups may be substituted with oxygen or sulfur, at least one-CH < may be substituted with-N < and at least one > CH2May be substituted by > C ═ O, and further at least one hydrogen may be substituted by fluorine, chlorine, iodine or hydroxyl.
[4]According to item [2]The saturated homopolyether is produced by a process wherein R is represented by the following formulae (1) and (2)1、R2And R3Independently hydrogen, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a linear alkenyl group having 2 to 20 carbon atoms, or a branched alkenyl group having 4 to 20 carbon atoms.
[5] The process for producing a saturated homopolyether according to item [1], wherein the unsaturated carbonyl compound is 2-ethylhexenal, and bis- (2-ethylhexyl) ether is produced.
[6] The process for producing a saturated homopolyether according to the item [1], wherein the unsaturated carbonyl compound is 2-butenal, to produce a dibutyl ether.
[7] The process for producing a saturated homopolyether according to the item [1], wherein the unsaturated carbonyl compound is 2-ethyl-2-butenal to produce bis- (2-ethylbutyl) ether.
[8] The process for producing a saturated homopolyether according to any one of the items [1] to [7], wherein the metal of the catalyst is palladium.
[9] The process for producing a saturated homopolyether according to any one of the items [1] to [8], wherein the carrier of the catalyst is one or more selected from the group consisting of alumina, silica and silica-alumina.
Detailed Description
The invention is a process for obtaining saturated homopolyethers from unsaturated carbonyl compounds in the presence of an unsaturated carbonyl compound and hydrogen.
(catalyst carrier)
The acidic catalyst carrier used in the process for producing a saturated homopolyether of the present invention is a so-called solid acid, and examples of the solid acid include: metal oxides such as alumina, silica-alumina, titania, silica-titania, zeolite, and cation exchange resins. The solid acid may be used as an acidic catalyst support in any form such as a commercially available product, a product obtained by calcining a commercially available product, and a product obtained by thermally decomposing a metal hydroxide or an organic metal compound.
(catalyst)
The catalyst of the present invention may be a catalyst in which a metal is supported on an acidic catalyst carrier, and the metal is preferably palladium, platinum, ruthenium, or the like, more preferably palladium. The catalyst used in the present invention can be prepared by supporting these metals on an acidic catalyst support by a known method, for example, impregnation, coprecipitation, or the like.
(production method, reaction form)
The method for producing a saturated homopolyether from an unsaturated carbonyl compound of the present invention is characterized in that: an unsaturated carbonyl compound as a raw material is reacted in the presence of hydrogen using a catalyst in which a metal is supported on an acidic catalyst support.
(reaction apparatus)
The reaction apparatus used for producing the saturated homopolyether of the present invention is not particularly limited. For example, a saturated homopolyether can be produced by charging an unsaturated carbonyl compound and a catalyst as raw materials into a batch reactor and reacting them under hydrogen pressure. In addition, saturated homopolyether can be produced by setting a catalyst layer in a fixed bed reactor, setting a reaction temperature, and then passing an unsaturated carbonyl compound and hydrogen as raw materials.
(raw materials to be processed)
The unsaturated carbonyl compound as a raw material is not particularly limited, and is preferably an aldehyde represented by formula (1).
In the formula (1), R1、R2And R3Independently hydrogen, alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkynyl with 2-20 carbon atoms, cycloalkyl with 5-20 membered ring, aryl with 5-20 membered ring or heterocycle with 5-20 membered ring, wherein at least one carbon in the groups can be replaced by oxygen or sulfur, at least one-CH can be replaced by-N, and at least one > CH2May be substituted by > C ═ O, and further at least one hydrogen may be substituted by fluorine, chlorine, iodine or hydroxyl.
R1、R2And R3Examples thereof include a linear saturated alkyl group having 1 to 20 carbon atoms, a branched saturated alkyl group having 3 to 20 carbon atoms, an unsaturated alkyl group having 2 to 20 carbon atoms, a saturated alicyclic hydrocarbon group having 3 to 20 carbon atoms, an unsaturated alicyclic hydrocarbon group having 2 to 20 carbon atoms, and the like. In addition, in these radicals, at least one carbon may be substituted by oxygen or sulfur, at least one-CH < may be substituted by-N < and at least one > CH2May be substituted by > C ═ O. Further, at least one hydrogen of these groups may be substituted by fluorine, chlorine, iodine or a hydroxyl group.
Examples of the linear saturated alkyl group having 1 to 20 carbon atoms include: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, and n-eicosyl, and the like.
Examples of the branched saturated alkyl group having 3 to 20 carbon atoms include: isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl and the like.
Examples of the unsaturated alkyl group having 2 to 20 carbon atoms include: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, and the like.
Examples of the saturated alicyclic hydrocarbon group having 3 to 20 carbon atoms include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, norbornyl, and the like.
Examples of the unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms include: cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, phenyl, naphthyl, and the like.
Examples of the unsaturated carbonyl compound as a raw material include: 2-butenal, 2-ethyl-2-hexenal, 2-ethyl-2-butenal, 2-hexenal, and the like.
(product of object)
The saturated homopolyether obtained from these raw materials is preferably an ether represented by the formula (2).
In the formula (2), R1、R2And R3With R in formula (1) as a starting material1、R2And R3And (7) corresponding. Further, R of the formula (1)1、R2Or R3R of formula (2) when unsaturated1、R2Or R3Sometimes also saturated.
The saturated homopolyether is dibutyl ether, bis (2-ethylhexyl) ether, bis (2-ethylbutyl) ether, dihexyl ether, etc.
(temperature of reaction conditions)
The reaction temperature in the method for producing a saturated homopolyether of the present invention is preferably in the range of 100 to 250 ℃. The temperature is preferably 100 ℃ or higher for sufficiently carrying out the reaction, and 250 ℃ or lower for maintaining good product selectivity. A more preferable temperature range is 120 to 200 ℃.
[ examples ]
The effects of the present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.
(reaction apparatus)
The reactor used an autoclave (start-200) made at high pressure in the east of Japan. A pipe into which hydrogen is introduced is provided in the reactor, and hydrogen gas is introduced into the reactor therefrom.
(catalyst)
As the catalyst, commercially available 5% palladium-supported alumina (palladium-alumina manufactured by n.e. kaika (n.e. chemcat)), 10% palladium carbon (Pd 10% palladium-activated carbon manufactured by Wako pure chemical industries), and developed sponge nickel (sponge nickel manufactured by tokyo chemical synthesis) were used.
(raw materials)
2-ethylhexenal as a raw material was used as it is without purification of a special reagent (and a special reagent produced by Wako pure chemical industries).
[ example 1]
10g of 5% palladium-supported alumina (palladium-alumina manufactured by n.e. chemcat) and 60g of 2-ethylhexenal (and a special reagent manufactured by Wako pure chemical industries, Ltd.) were weighed in a stainless steel autoclave having an internal volume of 200 ml. The pressure in the autoclave was increased to 4MPa in hydrogen, and then the temperature was increased to 150 ℃ to start the reaction. The time at which the reaction temperature was reached was set to 0 hour, and the reaction was carried out for 6 hours. Thereafter, the reaction mixture was cooled to room temperature and then depressurized to atmospheric pressure, and the reaction mixture was collected and analyzed.
The identification of the reaction product was performed by using a Gas Chromatography-Mass spectrometer (Gas Chromatography/Mass Spectroscopy, GC/MS) -TQ8040 manufactured by shimadzu corporation) and a nuclear magnetic resonance apparatus (warian nuclear magnetic resonance System (VARIAN NMR System)500MHz manufactured by Agilent Technologies), and the quantification of the reaction product was performed by using a Gas chromatograph (GC 2014 Flame ion detector (film IonizationDetector, FID manufactured by shimadzu corporation) provided with a capillary column (DB-160 m manufactured by Agilent Technologies). The analysis by gas chromatography was performed to determine the conversion of 2-ethylhexenal (hereinafter abbreviated as 2EH) and the selectivity of bis (2-ethylhexyl) ether (hereinafter abbreviated as DOE), 2-ethylhexanol (hereinafter abbreviated as OA), 2-ethylhexanal (hereinafter abbreviated as 2EHA), 3- (bis (2-ethylhexyloxy) methyl) heptane (hereinafter abbreviated as acetal), 2-ethyl-2-hexenyl-2-ethylhexyl ether (hereinafter abbreviated as vinyl ether) and the like after correcting the calibration curve.
The results are shown in table 1.
[ example 2]
Example 1 was used as a standard, except that the reaction time was changed to 12 hours. The results are shown in table 1.
[ example 3]
Example 1 was used as a standard, except that the reaction pressure was changed to 2.6 MPa. The results are shown in table 1.
[ example 4]
Example 1 was used as a standard, except that the reaction temperature was changed to 135 ℃. The results are shown in table 1.
Comparative example 1
Example 1 was used as a standard except that 10% palladium on carbon (Pd 10% of palladium-activated carbon produced by Wako pure chemical industries, Ltd.) was used as a catalyst. The results are shown in table 1.
Comparative example 2
The procedure of example 1 was repeated, except that sponge nickel (sponge nickel manufactured by Tokyo chemical conversion) was used as the catalyst, and the reaction was carried out at a reaction temperature of 100 ℃ and a reaction pressure of 1 MPa. The results are shown in table 1.
TABLE 1
[ example 5]
Example 1 was used as a standard except that 60g of 2-butenal (and a reagent of special grade produced by Wako pure chemical industries, Ltd.) was weighed in a reaction substrate and used for the reaction. The analysis by gas chromatography was performed to determine the conversion of 2-butenal (hereinafter abbreviated as CA) and the selectivity of dibutyl ether (hereinafter abbreviated as DBE), 1-butyraldehyde (hereinafter abbreviated as BA), 1-butanol (hereinafter abbreviated as BO), 1-dibutoxybutane (hereinafter abbreviated as acetal B), 2-butenyl-butyl ether (hereinafter abbreviated as vinyl ether B) and the like after correcting the calibration curve. The results are shown in table 2.
TABLE 2
[ example 6]
Example 1 was used as a standard except that 60g of 2-ethyl-2-butenal (and a special reagent manufactured by Wako pure chemical industries, Ltd.) was weighed in a reaction substrate and used for the reaction. The analysis by gas chromatography was performed to determine the conversion of 2-ethyl-2-butenal (hereinafter abbreviated as 2ECA) and the selectivity of bis (2-ethylbutyl) ether (hereinafter abbreviated as DEBE), 2-ethylbutylaldehyde (hereinafter abbreviated as 2EBA), 2-ethyl-1-butanol (hereinafter abbreviated as 2EBO), 1-bis (2-ethylbutoxy) -2-ethylbutane (hereinafter abbreviated as acetal C), 2-ethyl-2-butenyl-2-ethyl-butyl ether (hereinafter abbreviated as vinyl ether C) and the like after correcting the calibration curve. The results are shown in table 3.
TABLE 3
In each of the examples and comparative examples, the conversion of unsaturated aldehyde in the substrate was approximately 100%, and it was found that the selectivity for saturated ether in the examples was higher than that in the comparative example.
[ industrial applicability ]
The method for producing a saturated ether in the present invention is a very industrially effective method, since it uses only an unsaturated aldehyde as a raw material, and thus contributes to shortening the steps in the step of producing the corresponding ether.
Claims (9)
1. A process for producing a saturated homopolyether, characterized by using an unsaturated carbonyl compound and hydrogen as raw materials and using a catalyst in which a metal is supported on an acidic catalyst carrier.
2. The process for producing a saturated homopolyether according to claim 1, wherein the unsaturated carbonyl compound is an aldehyde represented by formula (1) to produce a compound represented by formula (2);
in the formulae (1) and (2), R1、R2And R3Independently hydrogen, alkyl with 1-20 carbon atoms, alkenyl with 2-20 carbon atoms, alkynyl with 2-20 carbon atoms, cycloalkyl with 5-20 membered ring, aryl with 5-20 membered ring or heterocycle with 5-20 membered ring, wherein at least one carbon in the groups can be replaced by oxygen or sulfur, at least one-CH can be replaced by-N, and at least one > CH2May be substituted by > C ═ O, and further at least one hydrogen may be substituted by fluorine, chlorine, iodine or hydroxyl.
3. The process for producing a saturated homopolyether according to claim 2, wherein R in the formulae (1) and (2)1、R2And R3Independently hydrogen, a C1-20 linear alkyl group, a C3-20 branched alkyl group, a C2-20 linear alkenyl group, or a C4-20 branched alkenyl group, wherein at least one carbon in these groups may be substituted with oxygen or sulfur, at least one-CH < may be substituted with-N < and at least one > CH2May be substituted by > C ═ O, and further at least one hydrogen may be substituted by fluorine, chlorine, iodine or hydroxyl.
4. The process for producing a saturated homopolyether according to claim 2, wherein R in the formulae (1) and (2)1、R2And R3Independently hydrogen, C1-20 linear alkyl group, C3A branched alkyl group having 20 carbon atoms, a linear alkenyl group having 2 to 20 carbon atoms or a branched alkenyl group having 4 to 20 carbon atoms.
5. The method for producing a saturated homopolyether according to claim 1, wherein the unsaturated carbonyl compound is 2-ethylhexenal, and bis- (2-ethylhexyl) ether is produced.
6. The method for producing a saturated homopolyether according to claim 1, wherein the unsaturated carbonyl compound is 2-butenal, and the dibutyl ether is produced.
7. The method for producing a saturated homopolyether according to claim 1, wherein the unsaturated carbonyl compound is 2-ethyl-2-butenal to produce bis- (2-ethylbutyl) ether.
8. The method of claim 1, wherein the metal of the catalyst is palladium.
9. The process for producing a saturated homopolyether according to claim 1, wherein the carrier of the catalyst is at least one member selected from the group consisting of alumina, silica and silica-alumina.
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| JP2018-192584 | 2018-10-11 | ||
| JP2018192584A JP7131279B2 (en) | 2018-10-11 | 2018-10-11 | Method for producing saturated homoethers from unsaturated carbonyl compounds |
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| WO2023061971A1 (en) | 2021-10-11 | 2023-04-20 | Organofuel Sweden Ab | A new fuel composition comprising a symmetric branched c12-c18 ether, or 3-(((2-ethylhexyl)oxy)methyl)heptane |
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| US2573678A (en) * | 1951-11-06 | Preparation and pyrolysis of satu | ||
| JPS496290B1 (en) * | 1968-11-25 | 1974-02-13 | ||
| DE2945050A1 (en) * | 1979-11-08 | 1981-05-21 | Basf Ag, 6700 Ludwigshafen | Bis:2-ethyl:hexyl-ether prepn. - by reacting 1-ethyl:hexen-2-al with 2-ethyl:hexanol and hydrogenating resulting diene over transition or noble metal catalyst |
| JPH0995461A (en) * | 1995-07-27 | 1997-04-08 | Kao Corp | Production of ether compound |
| US5756856A (en) * | 1995-07-08 | 1998-05-26 | Huels Aktiengesellschaft | Process for the preparation of 2-ethylhexanal |
| JP2013023460A (en) * | 2011-07-20 | 2013-02-04 | Jnc Corp | Method of producing reaction product of substrate and hydrogen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3014631B2 (en) * | 1995-05-17 | 2000-02-28 | 花王株式会社 | Novel ether compound and method for producing the same |
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2018
- 2018-10-11 JP JP2018192584A patent/JP7131279B2/en active Active
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2019
- 2019-08-06 CN CN201910720934.5A patent/CN111039763A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573678A (en) * | 1951-11-06 | Preparation and pyrolysis of satu | ||
| JPS496290B1 (en) * | 1968-11-25 | 1974-02-13 | ||
| DE2945050A1 (en) * | 1979-11-08 | 1981-05-21 | Basf Ag, 6700 Ludwigshafen | Bis:2-ethyl:hexyl-ether prepn. - by reacting 1-ethyl:hexen-2-al with 2-ethyl:hexanol and hydrogenating resulting diene over transition or noble metal catalyst |
| US5756856A (en) * | 1995-07-08 | 1998-05-26 | Huels Aktiengesellschaft | Process for the preparation of 2-ethylhexanal |
| JPH0995461A (en) * | 1995-07-27 | 1997-04-08 | Kao Corp | Production of ether compound |
| JP2013023460A (en) * | 2011-07-20 | 2013-02-04 | Jnc Corp | Method of producing reaction product of substrate and hydrogen |
Non-Patent Citations (1)
| Title |
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| NOBUHIRO IWASA等: ""Palladium-based alloy and monometallic catalysts for gas phase hydrogenation of crotonaldehyde: effects of alloying and alloy crystallite size"", 《APPLIED CATALYSIS A: GENERAL》 * |
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