JPH0733699A - Production of 1,4-decahydronaphthalenediol - Google Patents
Production of 1,4-decahydronaphthalenediolInfo
- Publication number
- JPH0733699A JPH0733699A JP5201033A JP20103393A JPH0733699A JP H0733699 A JPH0733699 A JP H0733699A JP 5201033 A JP5201033 A JP 5201033A JP 20103393 A JP20103393 A JP 20103393A JP H0733699 A JPH0733699 A JP H0733699A
- Authority
- JP
- Japan
- Prior art keywords
- decahydronaphthalenediol
- naphthoquinone
- hydrogenation
- present
- reaction
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 abstract description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 Glycol ethers Chemical class 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- RDAFFINKUCJOJK-UYIJSCIWSA-N (1z,5e)-cyclodeca-1,5-diene Chemical compound C1CC\C=C/CC\C=C\C1 RDAFFINKUCJOJK-UYIJSCIWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 208000012839 conversion disease Diseases 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
- 150000002009 diols Chemical class 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
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)
- Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は１，４−デカヒドロナフ
タレンジオールの製造方法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing 1,4-decahydronaphthalenediol.
【０００２】[0002]
【従来の技術】１，４−デカヒドロナフタレンジオール
はポリエステル、ポリウレタン、ポリカーボネート等を
構成するジオール成分等として使用されうる有用な化合
物である。BACKGROUND OF THE INVENTION 1,4-decahydronaphthalene diol is a useful compound which can be used as a diol component constituting polyester, polyurethane, polycarbonate and the like.
【０００３】該化合物を製造する方法としては、α−ナ
フトキノンを種々の方法により還元（たとえば、パラジ
ウム・カーボンの存在下に、６０〜７０℃、１０ｋｇ／
ｃｍ2 程度の条件下で水素化する方法、ハイドロサルフ
ァイトで還元する方法等）して得られる１，４−ジヒド
ロキシナフタレンを、さらにラネーニッケル存在下で水
素化する方法が知られている。しかし、該方法は水素化
反応工程を２度経由するといった製造上の不利がある。As a method for producing the compound, α-naphthoquinone is reduced by various methods (for example, in the presence of palladium-carbon, 60 to 70 ° C., 10 kg / kg).
Known is a method of hydrogenating 1,4-dihydroxynaphthalene obtained by hydrogenation under a condition of about cm 2 or reduction with hydrosulfite) in the presence of Raney nickel. However, this method has a manufacturing disadvantage that the hydrogenation reaction step is performed twice.
【０００４】また、ＵＳＰ（米国特許公報）３４７４１
４９号には、１，５−シクロデカジエンに有機過酸化物
を作用させた後、酸またはアルカリ条件下で加水分解す
る方法が記載されている。該方法は１，４−デカヒドロ
ナフタレンジオールを立体特異的に製造しうる点で優れ
るが、工業的な製造には適さない。USP (US Patent Publication) 34741
No. 49 describes a method in which 1,5-cyclodecadiene is reacted with an organic peroxide and then hydrolyzed under acidic or alkaline conditions. The method is excellent in that it can stereospecifically produce 1,4-decahydronaphthalenediol, but is not suitable for industrial production.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、α−ナフト
キノンから１，４−デカヒドロナフタレンジオールを直
接的に、しかも効率よく製造する方法を提供することを
目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for directly and efficiently producing 1,4-decahydronaphthalenediol from α-naphthoquinone.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、前記従来
技術の課題を解決すべく、鋭意検討を重ねた結果、以下
に示す特定の条件下で、α−ナフトキノンを水素化した
場合には１，４−デカヒドロナフタレンジオールを直接
的に、しかも効率よく製造しうることを見出した。本発
明はかかる新しい知見に基づいて完成されたものであ
る。The inventors of the present invention have conducted extensive studies to solve the above-mentioned problems of the prior art, and as a result, when α-naphthoquinone was hydrogenated under the following specific conditions: Found that 1,4-decahydronaphthalenediol can be produced directly and efficiently. The present invention has been completed based on this new finding.
【０００７】すなわち本発明は、α−ナフトキノンを、
極性の有機溶媒中、水素化触媒の存在下に、温度３０〜
２００℃、水素圧３０ｋｇ／ｃｍ2 以上の条件で、水素
化することを特徴とする１，４−デカヒドロナフタレン
ジオールの製造方法に関する。That is, the present invention provides α-naphthoquinone
In a polar organic solvent, in the presence of a hydrogenation catalyst, a temperature of 30-
The present invention relates to a method for producing 1,4-decahydronaphthalenediol, which comprises hydrogenating at 200 ° C. and a hydrogen pressure of 30 kg / cm 2 or more.
【０００８】本発明の水素化は極性の有機溶媒中で行
う。かかる極性の有機溶媒としては、メタノール、エタ
ノール、プロパノール等の低級アルコール類；エチレン
グリコール、プロピレングリコール等のグリコール類；
エチレングリコールのモノエーテル、ジエーテル等のグ
リコールエーテル類；酢酸、プロピオン酸等の有機酸
類；酢酸エチル等の有機酸エステル類；テトラヒドロフ
ラン、ジオキサン等のエーテル類；アセトン、メチルエ
チルケトン等のケトン類；ピリジン、キノリン、ピペリ
ジン、ジメチルホルムアミド等の有機塩基類等の反応時
に安定で、α−ナフトキノンが溶解し易い溶媒があげら
れる。これらの溶媒は１種を単独でまたは２種以上を組
み合わせて使用できる。これら極性の有機溶媒のなかで
も、α−ナフトキノンの溶解度が常温で１０〜２００ｇ
／１００ｇ程度のものがよく、特に低級アルコール類が
回収のし易さおよび安価であるので好ましい。The hydrogenation of the present invention is carried out in a polar organic solvent. Such polar organic solvents include lower alcohols such as methanol, ethanol and propanol; glycols such as ethylene glycol and propylene glycol;
Glycol ethers such as ethylene glycol monoether and diether; organic acids such as acetic acid and propionic acid; organic acid esters such as ethyl acetate; ethers such as tetrahydrofuran and dioxane; ketones such as acetone and methyl ethyl ketone; pyridine and quinoline Examples include solvents that are stable during the reaction of organic bases such as piperidine and dimethylformamide, and in which α-naphthoquinone is easily dissolved. These solvents may be used alone or in combination of two or more. Among these polar organic solvents, the solubility of α-naphthoquinone is 10 to 200 g at room temperature.
/ 100 g is preferable, and lower alcohols are particularly preferable because they are easily recovered and are inexpensive.
【０００９】極性の有機溶媒の使用量は特に限定されな
いが、α−ナフトキノンが溶解しうる量以上であるのが
よい。通常はα−ナフトキノン１重量部に対し１〜３０
重量部程度、好ましくは１〜１０重量部とされる。な
お、α−ナフトキノンは溶媒に溶解していてもよく、懸
濁していてもよい。The amount of the polar organic solvent used is not particularly limited, but it is preferably at least an amount capable of dissolving α-naphthoquinone. Usually 1 to 30 per 1 part by weight of α-naphthoquinone
The amount is about 1 part by weight, preferably 1 to 10 parts by weight. The α-naphthoquinone may be dissolved or suspended in the solvent.
【００１０】本発明で用いる水素化触媒としては、一般
に水素化に使用される白金、パラジウム、ルテニウム、
ニッケル、銅等の各種金属触媒があげられる。具体的に
は酸化白金、白金コロイド、銅クロマイト、パラジウム
・カーボン、ルテニウム・カーボン、ラネーニッケル等
があげられる。これらのなかでも芳香環の水素化に適す
ることからルテニウム・カーボンが好ましい。The hydrogenation catalyst used in the present invention includes platinum, palladium, ruthenium, which are generally used for hydrogenation.
Examples include various metal catalysts such as nickel and copper. Specific examples thereof include platinum oxide, platinum colloid, copper chromite, palladium carbon, ruthenium carbon and Raney nickel. Of these, ruthenium carbon is preferable because it is suitable for hydrogenation of aromatic rings.
【００１１】水素化触媒の使用量は、通常α−ナフトキ
ノン１００重量部に対し０．１〜５重量部程度、好まし
くは０．１〜２重量部である。０．１重量部より少ない
と水素化反応が進みにくく、また５重量部より多いと水
素化分解が生じ易くなりいずれの場合も好ましくない。The amount of hydrogenation catalyst used is usually about 0.1 to 5 parts by weight, preferably 0.1 to 2 parts by weight, based on 100 parts by weight of α-naphthoquinone. If it is less than 0.1 parts by weight, the hydrogenation reaction is difficult to proceed, and if it is more than 5 parts by weight, hydrogenolysis is likely to occur, which is not preferable in any case.
【００１２】水素化する際の、温度条件は３０〜２００
℃、好ましくは５０〜１５０℃である。３０℃より低い
場合は反応速度が遅くなり、また２００℃を越える場合
には水素化分解が生じ易くなりいずれの場合も好ましく
ない。また、水素圧は３０ｋｇ／ｃｍ2 以上、好ましく
は５０〜２００ｋｇ／ｃｍ2 である。３０ｋｇ／ｃｍ2
に満たない場合は芳香環の水素化が不十分なため目的物
である１，４−デカヒドロナフタレンジオールが得られ
ない。また、水素化時間は、通常１〜５時間程度であ
る。The temperature condition for hydrogenation is 30 to 200.
C, preferably 50 to 150C. When it is lower than 30 ° C, the reaction rate becomes slow, and when it exceeds 200 ° C, hydrogenolysis is likely to occur, which is not preferable. The hydrogen pressure is 30kg / cm 2 or more, preferably 50 to 200 kg / cm 2. 30 kg / cm 2
If the amount is less than 1, the target 1,4-decahydronaphthalenediol cannot be obtained because the hydrogenation of the aromatic ring is insufficient. The hydrogenation time is usually about 1 to 5 hours.
【００１３】反応終了後は、水素化触媒を濾過分離し、
次いで有機溶媒を減圧留去して１，４−デカヒドロナフ
タレンジオールを単離する。また、得られた１，４−デ
カヒドロナフタレンジオールはヘキサン、トルエン、ク
ロロベンゼン、水等の溶媒を単独でまたは混合して使用
することにより晶析してもよい。After completion of the reaction, the hydrogenation catalyst is separated by filtration,
Then, the organic solvent is distilled off under reduced pressure to isolate 1,4-decahydronaphthalenediol. Further, the obtained 1,4-decahydronaphthalenediol may be crystallized by using a solvent such as hexane, toluene, chlorobenzene, and water alone or in combination.
【００１４】[0014]
【発明の効果】本発明によれば、α−ナフトキノンから
１，４−デカヒドロナフタレンジオールを直接的に、し
かも高収率（収率９０％以上）で製造しうる方法を提供
することができる。According to the present invention, it is possible to provide a method capable of directly producing 1,4-decahydronaphthalenediol from α-naphthoquinone in a high yield (yield of 90% or more). .
【００１５】[0015]
【実施例】以下に、実施例及び比較例をあげて本発明を
さらに詳細に説明するが、本発明はこれら実施例に限定
されるものではない。EXAMPLES The present invention will be described in more detail below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
【００１６】実施例１ 撹拌機付きのステンレス製１リットル容のオートクレー
ブに、α−ナフトキノン１５０ｇ、メタノール３５０ｇ
および触媒として５０重量％含水ルテニウム・カーボン
（ルテニウム担持量５重量％）１．５ｇを仕込み、水素
圧５０ｋｇ／ｃｍ2 の一定圧力下に１５０℃で水素化反
応を行った。２時間反応後、所定量の水素吸収が認めら
れたので反応を停止した。次いで、触媒を濾過し、反応
液をエバポレーターで減圧濃縮した後、トルエンにて再
結晶し１，４−デカヒドロナフタレンジオールを得た。
ガスクロマトグラフィー分析の結果、α−ナフトキノン
の反応転化率は９９．６モル％であり、１，４−デカヒ
ドロナフタレンジオールの選択率は９８モル％であっ
た。なお、１，４−デカヒドロナフタレンジオールはマ
ススペクトル、ＮＭＲスペクトルおよび元素分析により
確認をした。Example 1 In a stainless steel 1 liter autoclave equipped with a stirrer, 150 g of α-naphthoquinone and 350 g of methanol
Then, 1.5 g of 50 wt% hydrous ruthenium-carbon (ruthenium supported amount: 5 wt%) was charged as a catalyst, and the hydrogenation reaction was carried out at 150 ° C. under a constant hydrogen pressure of 50 kg / cm 2 . After reacting for 2 hours, a predetermined amount of hydrogen absorption was observed, so the reaction was stopped. Then, the catalyst was filtered, the reaction solution was concentrated under reduced pressure by an evaporator, and recrystallized from toluene to obtain 1,4-decahydronaphthalenediol.
As a result of gas chromatography analysis, the reaction conversion rate of α-naphthoquinone was 99.6 mol%, and the selectivity of 1,4-decahydronaphthalene diol was 98 mol%. The 1,4-decahydronaphthalenediol was confirmed by mass spectrum, NMR spectrum and elemental analysis.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｂ０１Ｊ 27/122 9342−4Ｇ Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location B01J 27/122 9342-4G C07B 61/00 300
Claims (1)
中、水素化触媒の存在下に、温度３０〜２００℃、水素
圧３０ｋｇ／ｃｍ2 以上の条件で、水素化することを特
徴とする１，４−デカヒドロナフタレンジオールの製造
方法。1. An α-naphthoquinone is hydrogenated in a polar organic solvent in the presence of a hydrogenation catalyst at a temperature of 30 to 200 ° C. and a hydrogen pressure of 30 kg / cm 2 or more. For producing 1,4-decahydronaphthalenediol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5201033A JPH0733699A (en) | 1993-07-20 | 1993-07-20 | Production of 1,4-decahydronaphthalenediol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5201033A JPH0733699A (en) | 1993-07-20 | 1993-07-20 | Production of 1,4-decahydronaphthalenediol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0733699A true JPH0733699A (en) | 1995-02-03 |
Family
ID=16434329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5201033A Pending JPH0733699A (en) | 1993-07-20 | 1993-07-20 | Production of 1,4-decahydronaphthalenediol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0733699A (en) |
-
1993
- 1993-07-20 JP JP5201033A patent/JPH0733699A/en active Pending
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