JPS634816B2 - - Google Patents
Info
- Publication number
- JPS634816B2 JPS634816B2 JP56086886A JP8688681A JPS634816B2 JP S634816 B2 JPS634816 B2 JP S634816B2 JP 56086886 A JP56086886 A JP 56086886A JP 8688681 A JP8688681 A JP 8688681A JP S634816 B2 JPS634816 B2 JP S634816B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- aldehyde
- alcohol
- reaction
- carrier
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 claims description 20
- 229910052709 silver Inorganic materials 0.000 claims description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 9
- 239000004332 silver Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 16
- 150000001299 aldehydes Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JOFJLDMQBUWNGH-UHFFFAOYSA-N 2-propan-2-yloxyacetaldehyde Chemical group CC(C)OCC=O JOFJLDMQBUWNGH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- DNQCEHKIRWFQKJ-UHFFFAOYSA-N butanedial Chemical compound O=CCCC=O.O=CCCC=O DNQCEHKIRWFQKJ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は、アルデヒドの製造方法、より詳細に
は、分子内にエーテル結合を持つアルデヒド、ま
たは、内子内に２ケのアルデヒド基を持つジアル
デヒドの製造法の改良に関する。
従来、アルコールの脱水素反応によりアルデヒ
ドを得るには銅系の触媒が多用されている。例え
ば、エチルアルコールの脱水素によりアセトアル
デヒドを得るプロセスでは銅クロマイト触媒が工
業的にも使用されていた。アルコールからアルデ
ヒドを得る他の触媒系としては、メチルアルコー
ルの酸化脱水素によるホルムアルデヒドの製造に
用いられている銀触媒がある。このホルムアルデ
ヒド製造に用いられる触媒は、担体を用いない金
属単味の銀の粒状触媒である。
本発明の方法における分子内にエーテル結合を
持つアルコールまたはグリコールを酸化脱水素し
て、分子内にエーテル結合を持つアルデヒドまた
はジアルデヒドを得る目的には、前記の触媒を用
いるプロセスによつて高収率で目的アルデヒドを
得ることは出来ない。
本発明の目的とするところは、分子内のエーテ
ル結合を持つアルコールまたはグリコールを酸化
脱水素して、高収率で目的とするアルデヒドを得
る方法を提供することにある。
本発明者は、分子内にエーテル結合を持つアル
コールまたはグリコールの酸化脱水素に関して
種々研究した結果、銀を担持する担体を適当に選
ぶことにより、かつ、より調製した銀触媒を用い
ることにより、目的とするアルデヒドが高収率で
得られることを見出して、本発明を完成するに至
つた。
すなわち、本発明は、分子内にエーテル結合を
持つアルコールまたはグリコールを酸化脱水素し
て、分子内にエーテル結合を持つアルデヒドまた
はジアルデヒドを製造するに際し、表面積が２
m2／ｇに満たない担体に担持した銀触媒を用いて
反応せしめることを特徴とするアルデヒドの製造
方法である。
この本発明の方法によれば、目的とする分子内
にエーテル結合を持つアルデヒドまたはジアルデ
ヒドを収率良く製造することが出来る。
本発明の方法において出発物質として用いるア
ルコールは、RO−CH2CH2OH（Ｒは炭素数１〜
４のアルキル基を示す）またはHO−（CH2）o−
OH（ｎは２〜４の整数である）で表わされるエ
ーテル結合を持つアルコールまたはグリコールで
あつて、得られるアルデヒドはRO−CH2CHO
（Ｒは炭素数１〜４のアルキル基を示す）または
OHC−（CH2）o-2−CHO（ｎは２〜６の数整であ
る）で表わされるジアルデヒドである。例えば、
原料アルコールのＲがメチル基であるエチレング
リコールモノメチルエーテルを用いれば、得られ
るアルデヒドはメトキシ−アセトアルデヒドであ
り、Ｒがイソプロピル基であれば、イソプロポキ
シ−アセトアルデヒドが得られる。また、原料ア
ルコールがエチレングリコールであれば、得られ
るジアルデヒドはグリオキザールであり、１・４
−ブタンジオールからは１・４−ブタンジアール
（１・２−ジホルミルエタン）が得られる。
本発明の方法における触媒は、銀を特定な表面
積を持つた担体に担持したものである。好ましい
担体の表面積は、窒素ガスの沸点温度における担
体への吸着等温線にBETの吸着等温式を適用し
て算出した表面積が、２m2／ｇ未満のものであ
る。担体が反応に対して不活性であればその表面
積が２m2／ｇ未満であれば、その種類は問はな
い。すなわち、熔融アルミナ、熔融シリカ、シリ
コンカーバイドまたは陶磁器の細片等を担体とし
て用いることが出来る。
表面積が、上記の値以上であつても目的とする
アルデヒドは得られるが、その収率は低い。
担体上への銀の担持量は、１〜30wt％、特に
５〜10wt％の範囲が多用されるが、一般的には
銀の担持量は低い方が触媒コストを低減するうえ
で好ましい。触媒の調製方法は、常法、例えば、
硝酸銀等の銀塩を水に溶かし、担体に浸漬、乾
燥、焼成後還元処理することによる。
本発明の方法は、高温、気相で反応を実施する
が、反応温度は、300〜600℃、特に350〜450℃の
範囲が多用される。反応時の圧力は常圧近傍であ
つて、通常、原料となるアルコールの分圧は0.5
気圧以下が多用される。反応に際しては、原料ア
ルコールの分圧を0.5気圧以下にするのに、スチ
ーム、窒素、炭酸ガスまたはこれらの混合ガスを
原料アルコールと共に反応系に供給する場合が多
い。
酸化脱水素反応の酸化剤は酸素が用いられるが
酸素源としては、酸素ガスまたは空気が多用され
る。酸素の原料アルコールに対する割合は通常、
化学量論量より過剰の酸素を用いる。酸素の過剰
量は、化学量論量の1.5〜３倍量が多用される。
反応物質と触媒床との接触時間は、0.1〜３秒
の範囲が用いられる。本発明の方法を実施するの
に用いる触媒床は固定床が適しているが、流動床
を用いることも出来る。
本発明の方法によつて得られる分子内にエーテ
ル結合を持つアルデヒドまたはジアルデヒドは、
アミノ酸等の合成原料、または繊維および紙加工
剤の合成原料等に広範な用途を持つ有用な化合物
である。
以下、実施例により本発明の方法を説明する。
実施例 １
内径12ｍ／ｍのステンレススチール製の円筒を
反応管に用い、粒径１〜1.6ｍ／ｍの触媒を２ml
充填した。供給原料として、エチレングリコール
モノメチルエーテルを0.85ｇ／Hr.窒素ガス100
ml／min、空気20ml／minの混合物を400℃に加
熱した触媒床に予熱気化させてから供給した。反
応器を流出した反応物をドライアイスで冷却した
トラツプに捕集した。トラツプに捕集した液体の
重量および、その組成をガスクロマトグラフで分
析して、エチレングリコールモノメチルエーテル
の転化率およびメトキシアセトアルデヒドへの選
択率を算出した。
用いる触媒の種類をかえて得られた結果を表−
１に示した。
The present invention relates to a method for producing an aldehyde, and more particularly, to an improved method for producing an aldehyde having an ether bond in the molecule or a dialdehyde having two aldehyde groups in the inner molecule. Conventionally, copper-based catalysts have been frequently used to obtain aldehydes through the dehydrogenation reaction of alcohols. For example, copper chromite catalysts have been used industrially in the process of obtaining acetaldehyde by dehydrogenating ethyl alcohol. Other catalyst systems for obtaining aldehydes from alcohols include silver catalysts used in the production of formaldehyde by oxidative dehydrogenation of methyl alcohol. The catalyst used for this formaldehyde production is a granular metal catalyst of silver without using a carrier. In order to obtain an aldehyde or dialdehyde having an ether bond in the molecule by oxidative dehydrogenation of an alcohol or glycol having an ether bond in the molecule in the method of the present invention, a process using the above-mentioned catalyst can be used in high yield. It is not possible to obtain the desired aldehyde at this rate. An object of the present invention is to provide a method for obtaining a desired aldehyde in high yield by oxidatively dehydrogenating an alcohol or glycol having an ether bond in the molecule. As a result of various studies on the oxidative dehydrogenation of alcohols or glycols having an ether bond in the molecule, the present inventor has determined that the desired purpose can be achieved by appropriately selecting a carrier supporting silver and using a more prepared silver catalyst. The present invention was completed by discovering that the aldehyde can be obtained in high yield. That is, in the present invention, when an aldehyde or dialdehyde having an ether bond in the molecule is produced by oxidative dehydrogenation of an alcohol or glycol having an ether bond in the molecule, the surface area is 2.
This is a method for producing aldehydes, characterized in that the reaction is carried out using a silver catalyst supported on a carrier of less than m 2 /g. According to the method of the present invention, the desired aldehyde or dialdehyde having an ether bond in the molecule can be produced with good yield. The alcohol used as a starting material in the method of the present invention is RO-CH 2 CH 2 OH (R has 1 to 1 carbon atoms).
4) or HO-( CH2 ) o-
An alcohol or glycol with an ether bond represented by OH (n is an integer from 2 to 4), and the resulting aldehyde is RO-CH 2 CHO
(R represents an alkyl group having 1 to 4 carbon atoms) or
It is a dialdehyde represented by OHC-( CH2 ) o-2 -CHO (n is an integer from 2 to 6). for example,
If ethylene glycol monomethyl ether in which R of the raw alcohol is a methyl group is used, the resulting aldehyde will be methoxy-acetaldehyde, and if R is an isopropyl group, isopropoxy-acetaldehyde will be obtained. In addition, if the raw alcohol is ethylene glycol, the dialdehyde obtained is glyoxal, which is 1.4
-Butanediol yields 1,4-butanedial (1,2-diformylethane). The catalyst used in the method of the present invention is one in which silver is supported on a carrier having a specific surface area. A preferable carrier has a surface area of less than 2 m 2 /g, which is calculated by applying the BET adsorption isotherm to the adsorption isotherm to the carrier at the boiling point temperature of nitrogen gas. The type of carrier does not matter as long as it is inert to the reaction and has a surface area of less than 2 m 2 /g. That is, fused alumina, fused silica, silicon carbide, ceramic strips, etc. can be used as the carrier. Even if the surface area is greater than the above value, the desired aldehyde can be obtained, but the yield is low. The amount of silver supported on the carrier is often in the range of 1 to 30 wt%, particularly 5 to 10 wt%, but generally a lower amount of silver supported is preferable in terms of reducing catalyst cost. The catalyst can be prepared by a conventional method, for example,
This is done by dissolving a silver salt such as silver nitrate in water, immersing it in a carrier, drying it, firing it, and then subjecting it to a reduction treatment. In the method of the present invention, the reaction is carried out at high temperature in the gas phase, and the reaction temperature is often in the range of 300 to 600°C, particularly 350 to 450°C. The pressure during the reaction is near normal pressure, and the partial pressure of the raw alcohol is usually 0.5.
Below atmospheric pressure is often used. During the reaction, steam, nitrogen, carbon dioxide, or a mixed gas thereof is often supplied to the reaction system together with the raw alcohol in order to reduce the partial pressure of the raw alcohol to 0.5 atm or less. Oxygen is used as the oxidizing agent in the oxidative dehydrogenation reaction, and oxygen gas or air is often used as the oxygen source. The ratio of oxygen to raw alcohol is usually
An excess of oxygen over the stoichiometric amount is used. The excess amount of oxygen is often 1.5 to 3 times the stoichiometric amount. The contact time between the reactants and the catalyst bed is in the range of 0.1 to 3 seconds. The catalyst bed used to carry out the process of the invention is suitably a fixed bed, but a fluidized bed can also be used. The aldehyde or dialdehyde having an ether bond in the molecule obtained by the method of the present invention is
It is a useful compound that has a wide range of uses, including as a raw material for the synthesis of amino acids, fibers, and paper processing agents. The method of the present invention will be explained below with reference to Examples. Example 1 A stainless steel cylinder with an inner diameter of 12 m/m was used as a reaction tube, and 2 ml of catalyst with a particle size of 1 to 1.6 m/m was charged.
Filled. As feed material, ethylene glycol monomethyl ether 0.85g/Hr.Nitrogen gas 100
ml/min and air at 20 ml/min, which was preheated and vaporized before being fed to the catalyst bed heated to 400°C. The reactants flowing out of the reactor were collected in a trap cooled with dry ice. The weight and composition of the liquid collected in the trap were analyzed by gas chromatography to calculate the conversion rate of ethylene glycol monomethyl ether and the selectivity to methoxyacetaldehyde. The table shows the results obtained by changing the type of catalyst used.
Shown in 1.
【表】
実施例 ２
実施例１と同様の反応器と触媒を用い、供給原
料をエチレングリコール0.40ｇ／Hr.水0.60ｇ／
Hr.窒素100ml／min、空気30ml／minにかえて反
応させた。
捕集物の重さを測定し、その組成を高速液体ク
ロマトグラフイーで分析し、エチレングリコール
の転化率およびグリオキザールの選択率を算出し
た。結果を表−２に示す。[Table] Example 2 Using the same reactor and catalyst as in Example 1, the feedstock was ethylene glycol 0.40g/Hr.water 0.60g/Hr.
The reaction was performed by changing the nitrogen flow to 100 ml/min and the air to 30 ml/min. The weight of the collected material was measured, its composition was analyzed by high performance liquid chromatography, and the ethylene glycol conversion rate and glyoxal selectivity were calculated. The results are shown in Table-2.
【表】【table】
【表】
実施例 ３
実施例１と同様の装置に10wt％Ag／熔融アル
ミナ（0.07m2／ｇ）触媒２mlを充填し、反応温度
を400℃で用いる原料アルコールをかえて反応さ
せた。結果を表−３に示す。[Table] Example 3 The same apparatus as in Example 1 was filled with 2 ml of 10 wt% Ag/fused alumina (0.07 m 2 /g) catalyst, and the reaction was carried out at a reaction temperature of 400° C. by changing the raw material alcohol used. The results are shown in Table-3.
Claims (1)
のアルキル基を示す）またはHO−（CH2）o−OH
（ｎは２〜６の整数である）で表わされるアルコ
ールを酸化脱水素して、一般式RO−CH2CHO
（Ｒは前記に同じ）またはOHC−（CH2）o-2−
CHO、（ｎは前記に同じ）で表わされるアルデヒ
ドを製造するに際し、表面積が２m2／ｇに満たな
い担体に担持した銀触媒を用いることを特徴とす
るアルデヒドの製造方法。1 General formula RO-CH 2 CH 2 OH (R has 1 to 4 carbon atoms
) or HO−(CH 2 ) o −OH
(n is an integer from 2 to 6) is oxidized and dehydrogenated to form the general formula RO-CH 2 CHO
(R is the same as above) or OHC-( CH2 ) o-2-
1. A method for producing an aldehyde, which comprises using a silver catalyst supported on a carrier having a surface area of less than 2 m 2 /g when producing an aldehyde represented by CHO (n is the same as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56086886A JPS57203024A (en) | 1981-06-08 | 1981-06-08 | Preparation of aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56086886A JPS57203024A (en) | 1981-06-08 | 1981-06-08 | Preparation of aldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57203024A JPS57203024A (en) | 1982-12-13 |
| JPS634816B2 true JPS634816B2 (en) | 1988-02-01 |
Family
ID=13899309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56086886A Granted JPS57203024A (en) | 1981-06-08 | 1981-06-08 | Preparation of aldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57203024A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0388910U (en) * | 1989-12-28 | 1991-09-11 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5241122A (en) * | 1990-06-13 | 1993-08-31 | Union Camp Corporation | Catalysts comprising group IB metals |
-
1981
- 1981-06-08 JP JP56086886A patent/JPS57203024A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0388910U (en) * | 1989-12-28 | 1991-09-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57203024A (en) | 1982-12-13 |
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