JPS6260374B2 - - Google Patents
Info
- Publication number
- JPS6260374B2 JPS6260374B2 JP55188777A JP18877780A JPS6260374B2 JP S6260374 B2 JPS6260374 B2 JP S6260374B2 JP 55188777 A JP55188777 A JP 55188777A JP 18877780 A JP18877780 A JP 18877780A JP S6260374 B2 JPS6260374 B2 JP S6260374B2
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- octylaldehyde
- reaction
- octanol
- dienol
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 27
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- YHYGSIBXYYKYFB-VOTSOKGWSA-N (2e)-octa-2,7-dien-1-ol Chemical compound OC\C=C\CCCC=C YHYGSIBXYYKYFB-VOTSOKGWSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 25
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 150000002941 palladium compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XULHFMYCBKQGEE-MRXNPFEDSA-N 2-Hexyl-1-decanol Natural products CCCCCCCC[C@H](CO)CCCCCC XULHFMYCBKQGEE-MRXNPFEDSA-N 0.000 description 1
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- NFDFQCUYFHCNBW-SCGPFSFSSA-N dienestrol Chemical compound C=1C=C(O)C=CC=1\C(=C/C)\C(=C\C)\C1=CC=C(O)C=C1 NFDFQCUYFHCNBW-SCGPFSFSSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 1
- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 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
【発明の詳細な説明】
本発明は水素およびパラジウムおよび／または
その化合物の存在下に１−オクタ−２・７−ジエ
ノールを水添異性化することによるｎ−オクチル
アルデヒドの製造法に関する。
ｎ−オクチルアルデヒドは香料成分として、あ
るいはｎ−オクタン酸、ｎ−オクチルアミン、ジ
−ｎ−オクチルアミン、トリ−ｎ−オクチルアミ
ン、２−ヘキシル−１−デカノール、２−ヘキシ
ルデカン酸、ｎ−オクタノールなどの出発原料と
して重要な化合物であるが、今日に至るまで工業
的に有利な製造法が確立されていない。現在、ｎ
−オクチルアルデヒドは天然グリセライド中に微
量含まれるｎ−オクタン酸エステルを高圧下で水
素還元してｎ−オクタノールとし、次いでこれを
脱水素するという極めて煩雑な方法により製造さ
れており、量的にも価格的にも大きな制約を受け
ているため、上記の各種工業用途の原料とはなり
得ていないのが現状である。１−ヘプテンをヒド
ロホルミル化してｎ−オクチルアルデヒドを製造
する方法も考えられるが、１−ヘプテンの安価な
入手が困難な事情を考慮するとこの方法は工業的
には採用し得ない。
次に本発明者らはパラジウム錯化合物を主触媒
とするブタジエンと水との反応により１−オクタ
−２・７−ジエノールを工業的に有利に製造しう
ることを見出した（特願昭55−40989号）。本発明
者らはかかる背景から１−オクタ−２・７−ジエ
ノールの化学的反応性について種々検討を行なつ
た結果、パラジウムおよび／またはその化合物お
よび水素の存在下液相で１−オクタ−２・７−ジ
エノールを反応させると意外にも部分水添異性化
物であるｎ−オクチルアルデヒドが生成すること
を見出し、本発明を完成するに至つた。本発明に
従う１−オクタ−２・７−ジエノールの水添異性
化反応においては、通常一般に、目的とするｎ−
オクチルアルデヒドのほかに完全水添物であるｎ
−オクタノールが生成する。ｎ−オクタノールと
ｎ−オクチルアルデヒドの生成比は反応混合液中
の１−オクタ−２・７−ジエノール濃度、溶存水
素濃度（水素圧ならびに撹拌効率と関連）、反応
温度および触媒濃度などによつて変化させること
ができる。水添異性化反応の収率を向上させるた
めにはｎ−オクタノールの生成をできる限り抑制
することが望ましいが、ｎ−オクタノールもまた
工業的に有用な化合物であり、かつｎ−オクタノ
ールとｎ−オクチルアルデヒドとはそれらの沸点
差が大きいので容易に蒸留分離することができ
る。したがつてｎ−オクタノールとｎ−オクチル
アルデヒドとの生成比は工業的にはそれぞれの化
合物の需要に応じて調節すればよい。
本発明の方法において触媒として用いるパラジ
ウムおよびパラジウム化合物としてはパラジウム
黒、パラジウム粉末、臭化パラジウム、塩化パラ
ジウム、シアン化パラジウム、硝酸パラジウム、
酸化パラジウム、硫酸パラジウム、ナトリウムク
ロロパラデートなどを挙げることができる。パラ
ジウムおよびパラジウム化合物は反応系内におい
て一般に微細に分散された状態で存在する。パラ
ジウムおよびパラジウム化合物は活性炭、硫酸バ
リウム、シリカ、アルミナ、ゼオライトなどの担
体に担持させて用いてもよい。担体に担持された
パラジウム触媒はたとえばテルル、セレン、アン
チモンなどの金属またはその化合物で部分的に変
性されていてもよい。反応混合液中におけるパラ
ジウムおよび／またはパラジウム化合物の濃度は
パラジウム金属換算で0.005〜５重量％が好適で
ある。
本発明の方法においては原料である１−オクタ
−２・７−ジエノールに溶媒としての機能を兼ね
させることもできるし、反応条件下で不活性な有
機溶媒、たとえばジエチルエーテル、ジオキサ
ン、テトラヒドロフラン、エタノール、ｎ−ブタ
ノール、ｎ−オクタノール、ｎ−ヘキサン、ｎ−
ヘプタン、ｎ−オクタン、シクロヘキサン、ベン
ゼン、トルエン、キシレンなどを反応溶媒として
用いることもできる。本発明の方法を実施するに
あたり反応温度は約30〜150℃の範囲から選ばれ
る。水素圧には厳密な意味での限界値はないが、
通常一般に１〜50気圧の範囲から選ぶのが有利で
ある。
本発明の方法において反応温度および水素圧は
ｎ−オクタノールとｎ−オクチルアルデヒドの生
成比を支配し、これらを前述の範囲内で高温およ
び低水素圧に保つほどｎ−オクチルアルデヒドの
生成割合は増大する。またｎ−オクタノールとｎ
−オクチルアルデヒドの生成比は触媒濃度および
１−オクタ−２・７−ジエノール濃度によつても
変化し、これらを高い濃度に保つほどｎ−オクチ
ルアルデヒドの生成割合は増大する。
本発明の方法に従う反応は撹拌型反応槽中また
はパラジウムおよびパラジウム化合物を担体に担
持させて用いる場合は充填塔型反応槽中で連続方
式またはバツチ方式によつて実施することができ
る。本発明の方法により生成するｎ−オクチルア
ルデヒドは反応後の反応混合液から必要に応じて
触媒を分離したのち、常法に従つて分留を行なう
ことにより高純度で取得することができる。後留
分として併産品であるｎ−オクタノールが取得さ
れる。
以下に実施例によつて本発明を具体的に説明す
るが、本発明はこれら実施例によつて制限される
ものではない。
実施例 １
温度計、水素吹込み口を備えた内容積300mlの
電磁撹拌式オートクレーブに１−オクタ−２・７
−ジエノール5.0ｇ（39.7ミリモル）、ｎ−ブタノ
ール50mlおよびパラジウム黒（日本エンゲルハル
ト社製）36mg（反応混合液の0.08重量％に相当）
を仕込んだ。オートクレーブ内を水素ガスで８気
圧に加圧した後、内容物を300rpmの回転速度で
撹拌しながら80℃の条件下で３時間反応を行なつ
た。反応混合液をガスクロマトグラフイーで分析
した結果、ｎ−オクチルアルデヒド1.8ｇ（仕込
み１−オクタ−２・７−ジエノール基準で36％の
収率）およびｎ−オクタノール3.3ｇが生成して
いることがわかつた。
実施例２〜実施例７
実施例１で用いたのと同一の反応装置を用い、
１−オクタ−２・７−ジエノール濃度、水素圧、
溶媒の種類、反応温度、撹拌速度および触媒の種
類と量を表１に示す如く種々変化させた以外は実
施例１と同様にして反応を行なつた。結果を表１
に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for the production of n-octylaldehyde by hydrogenoisomerizing 1-octa-2,7-dienol in the presence of hydrogen and palladium and/or compounds thereof. n-Octylaldehyde is used as a fragrance ingredient, or as a fragrance ingredient, n-octanoic acid, n-octylamine, di-n-octylamine, tri-n-octylamine, 2-hexyl-1-decanol, 2-hexyldecanoic acid, n-octanol. Although it is an important compound as a starting material, no industrially advantageous production method has been established to date. Currently, n
-Octylaldehyde is produced by an extremely complicated method in which n-octanoic acid ester, which is present in trace amounts in natural glycerides, is reduced with hydrogen under high pressure to form n-octanol, which is then dehydrogenated. Currently, it cannot be used as a raw material for the various industrial uses mentioned above because it is subject to significant price constraints. Although it is possible to produce n-octylaldehyde by hydroformylating 1-heptene, this method cannot be adopted industrially considering the difficulty in obtaining 1-heptene at a low price. Next, the present inventors discovered that 1-octa-2,7-dienol can be industrially advantageously produced by the reaction of butadiene and water using a palladium complex compound as the main catalyst (Japanese Patent Application No. No. 40989). The present inventors conducted various studies on the chemical reactivity of 1-octa-2,7-dienol based on this background, and found that 1-octa-2 - It was unexpectedly discovered that a partially hydrogenated isomerized product, n-octylaldehyde, is produced when 7-dienol is reacted, leading to the completion of the present invention. In the hydroisomerization reaction of 1-octa-2,7-dienol according to the present invention, the target n-
In addition to octylaldehyde, fully hydrogenated n
- Octanol is produced. The production ratio of n-octanol and n-octylaldehyde depends on the 1-octa-2,7-dienol concentration in the reaction mixture, dissolved hydrogen concentration (related to hydrogen pressure and stirring efficiency), reaction temperature, catalyst concentration, etc. It can be changed. In order to improve the yield of the hydroisomerization reaction, it is desirable to suppress the production of n-octanol as much as possible, but n-octanol is also an industrially useful compound, and n-octanol and n- Since there is a large difference in boiling point from octylaldehyde, it can be easily separated by distillation. Therefore, the production ratio of n-octanol and n-octylaldehyde may be adjusted industrially depending on the demand for each compound. Palladium and palladium compounds used as catalysts in the method of the present invention include palladium black, palladium powder, palladium bromide, palladium chloride, palladium cyanide, palladium nitrate,
Examples include palladium oxide, palladium sulfate, and sodium chloroparadate. Palladium and palladium compounds generally exist in a finely dispersed state within the reaction system. Palladium and palladium compounds may be supported on a carrier such as activated carbon, barium sulfate, silica, alumina, or zeolite. The palladium catalyst supported on a carrier may be partially modified with a metal such as tellurium, selenium, antimony or a compound thereof. The concentration of palladium and/or palladium compound in the reaction mixture is preferably 0.005 to 5% by weight in terms of palladium metal. In the method of the present invention, the raw material 1-octa-2,7-dienol can also function as a solvent, or organic solvents that are inert under the reaction conditions, such as diethyl ether, dioxane, tetrahydrofuran, ethanol, etc. , n-butanol, n-octanol, n-hexane, n-
Heptane, n-octane, cyclohexane, benzene, toluene, xylene, etc. can also be used as a reaction solvent. In carrying out the method of the present invention, the reaction temperature is selected from the range of about 30-150°C. Although there is no strict limit to hydrogen pressure,
It is generally advantageous to choose from a range of 1 to 50 atmospheres. In the method of the present invention, the reaction temperature and hydrogen pressure control the production ratio of n-octanol and n-octylaldehyde, and the more the temperature and hydrogen pressure are kept within the above-mentioned ranges, the more the production ratio of n-octylaldehyde increases. do. Also, n-octanol and n
The production ratio of -octylaldehyde also changes depending on the catalyst concentration and 1-octa-2,7-dienol concentration, and the higher these concentrations are maintained, the greater the production ratio of n-octylaldehyde. The reaction according to the method of the present invention can be carried out in a continuous or batchwise manner in a stirred reactor or in a packed column reactor when palladium and palladium compounds are supported on a carrier. The n-octylaldehyde produced by the method of the present invention can be obtained in high purity by separating the catalyst from the reaction mixture after the reaction, if necessary, and then performing fractional distillation according to a conventional method. The co-product n-octanol is obtained as an after-distillate. The present invention will be specifically explained below with reference to Examples, but the present invention is not limited to these Examples. Example 1 A 1-octa-2.7 autoclave with an internal volume of 300 ml was equipped with a thermometer and a hydrogen inlet.
- 5.0 g (39.7 mmol) of dienol, 50 ml of n-butanol and 36 mg of palladium black (manufactured by Engelhard Japan) (equivalent to 0.08% by weight of the reaction mixture)
I prepared it. After pressurizing the inside of the autoclave to 8 atmospheres with hydrogen gas, the reaction was carried out at 80° C. for 3 hours while stirring the contents at a rotational speed of 300 rpm. Analysis of the reaction mixture by gas chromatography revealed that 1.8 g of n-octylaldehyde (36% yield based on the 1-octa-2,7-dienol used) and 3.3 g of n-octanol were produced. I understand. Examples 2 to 7 Using the same reaction apparatus as used in Example 1,
1-octa-2,7-dienol concentration, hydrogen pressure,
The reaction was carried out in the same manner as in Example 1, except that the type of solvent, reaction temperature, stirring speed, and type and amount of catalyst were varied as shown in Table 1. Table 1 shows the results.
Shown below. 【table】
Claims (1)
に水素の存在下に液相で１−オクタ−２・７−ジ
エノールを水添異性化することを特徴とするｎ−
オクチルアルデヒドの製造法。1 n- characterized by hydrogenoisomerizing 1-octa-2,7-dienol in the liquid phase in the presence of palladium and/or its compound and hydrogen
Method for producing octylaldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55188777A JPS57112345A (en) | 1980-12-29 | 1980-12-29 | Preparation of n-octylaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55188777A JPS57112345A (en) | 1980-12-29 | 1980-12-29 | Preparation of n-octylaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57112345A JPS57112345A (en) | 1982-07-13 |
| JPS6260374B2 true JPS6260374B2 (en) | 1987-12-16 |
Family
ID=16229600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55188777A Granted JPS57112345A (en) | 1980-12-29 | 1980-12-29 | Preparation of n-octylaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57112345A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6442176U (en) * | 1987-09-08 | 1989-03-14 |
-
1980
- 1980-12-29 JP JP55188777A patent/JPS57112345A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6442176U (en) * | 1987-09-08 | 1989-03-14 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57112345A (en) | 1982-07-13 |
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