JPS6148509B2 - - Google Patents
Info
- Publication number
- JPS6148509B2 JPS6148509B2 JP53096115A JP9611578A JPS6148509B2 JP S6148509 B2 JPS6148509 B2 JP S6148509B2 JP 53096115 A JP53096115 A JP 53096115A JP 9611578 A JP9611578 A JP 9611578A JP S6148509 B2 JPS6148509 B2 JP S6148509B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- present
- oxygen
- palladium
- primary alcohol
- 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 10
- 239000003054 catalyst Substances 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 150000003138 primary alcohols Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- -1 R′: H Chemical group 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 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
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- ACOQOLIJGGKILA-UHFFFAOYSA-N 2-methylpentane-1,1-diol Chemical compound CCCC(C)C(O)O ACOQOLIJGGKILA-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000013462 industrial intermediate Substances 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 本発明はラクトンの製法に関する。[Detailed description of the invention] The present invention relates to a method for producing lactones.
さらに詳しく云えば本発明は緩和な条件下で酸
化的にラクトンを製造する方法に関する。 More particularly, the present invention relates to a process for producing lactones oxidatively under mild conditions.
有用な工業用中間体や溶剤等に使用されるラク
トンの製法は、従来まで、二塩基カルボン酸また
はその無水物等を水素で還元する方法が工業的に
実施されている。ところでかかるカルボン酸無水
物等の還元は反応が進行しすぎるとジオールにま
で還元されるので上手く途中で止める工夫を要す
るし、さらには分子量の大きい化合物から高価な
水素により分子量の小さい化合物を合成すること
は経済的にみて大きな不利を伴う方法であるとい
える。 BACKGROUND ART Conventionally, lactones used as useful industrial intermediates and solvents have been produced industrially by reducing dibasic carboxylic acids or their anhydrides with hydrogen. However, if the reaction progresses too much, it will be reduced to a diol, so it is necessary to find a way to stop the reaction midway through, and furthermore, it is necessary to synthesize a compound with a small molecular weight from a compound with a large molecular weight using expensive hydrogen. This can be said to be a method that is economically disadvantageous.
そこで本発明者らは、かかる不利益をなくすた
め酸化的にラクトンを製造する方法について検討
したところ、少なくとも４ケの直鎖炭素原子を有
するα・ωジオールや、α炭素を除く骨格炭素の
誘導体等をパラジウムまたは白金触媒を用いて酸
化することで選択的に対応するラクトンが緩和な
条件下で生成することを見出し本発明をなすに至
つたのである。 Therefore, the present inventors investigated methods for producing lactones oxidatively in order to eliminate such disadvantages, and found that α/ω diols having at least 4 linear carbon atoms and derivatives of skeletal carbons excluding α carbons They discovered that the corresponding lactones can be selectively produced under mild conditions by oxidizing them using palladium or platinum catalysts, leading to the present invention.
本発明の一例を一般式で示すと次の如くにな
る。 An example of the present invention is expressed by the following general formula.
ただし、
（R1R2：Ｈ、アルキル基、
R′：Ｈ、アルキル基、
ｎ：２以上）
ここで出発原料となる化合物は２個のOH基を
有し、そのOH基の間が４個以上の炭素原子によ
つて結ばれ、かつそのうちの１個が第一級アルコ
ールであつて、まず、上記R1・R2及びR′がＨ
で、かつｎが２以上のα・ωジオールであり、こ
の例としては、１・４ブタンジオール、１・５ペ
ンタンジオール、１・６ヘキサンジオールの如き
飽和α・ω二価アルコールがあり、さらには置換
基を有するジオール類、たとえば１・４ペンタン
ジオール、２メチルペンタンジオール２・４等の
ジオール類が挙げられる。 However, (R 1 R 2 : H, alkyl group, R′: H, alkyl group, n: 2 or more) The compound serving as the starting material has two OH groups, and the space between the OH groups is 4. R 1 , R 2 and R' are connected by more than 1 carbon atoms, and one of them is a primary alcohol, and R 1 , R 2 and R' are H
and n is an α·ω diol of 2 or more, examples of which include saturated α·ω dihydric alcohols such as 1,4 butanediol, 1,5 pentanediol, 1,6 hexanediol, and Examples of diols include substituent-containing diols, such as 1,4-pentanediol, 2-methylpentanediol, and 2,4-diol.
さらに本発明の出発原料としては、上記一般式
以外のたとえば１・４ブテンジオール−２、１・
５ペンテンジオール−３、１・８オクテンジオー
ル−２の如き不飽和α・ω二価アルコールも使用
出来る。 Furthermore, as a starting material of the present invention, other than the above general formula, such as 1,4-butenediol-2,1,
Unsaturated alpha-omega dihydric alcohols such as 5-pentenediol-3 and 1.8-octenediol-2 can also be used.
本発明で使用する酸素は分子状酸素、すなわち
酸素ガス自体又は酸素ガスを反応に不活性な希釈
剤、例えば窒素、炭酸ガスなどで希釈した混合ガ
スの形とすることができ、空気を用いることもで
きる。反応系に存在させる酸素の量は、反応に必
要な化学量論量以上、好ましくは化学量論量の
1.5倍以上あれば充分である。 The oxygen used in the present invention can be in the form of molecular oxygen, that is, oxygen gas itself or a mixed gas obtained by diluting oxygen gas with a diluent inert to the reaction, such as nitrogen or carbon dioxide gas, and air can be used. You can also do it. The amount of oxygen present in the reaction system is greater than or equal to the stoichiometric amount required for the reaction, preferably less than the stoichiometric amount.
1.5 times or more is sufficient.
次に本発明を実施するにあたり、用いる触媒は
パラジウムまたは白金であるが、これらは金属そ
のものでもよいが担体に担持させて用いる方が好
ましい。その際、用いる担体としては活性炭、シ
リカ、アルミナ等通常のもので差支えない。かか
る担体に対し、パラジウムまたは白金の担持量は
重量で0.2〜20wt％の範囲で使用出来るが、好ま
しくは0.5〜10wt％の範囲がよい。これら触媒の
調製は通常行なわれている方法でよいが、一つの
例として、パラジウムまたは白金の塩の水溶液に
担体を浸漬させ、乾燥後、水素、ヒドラジン、ホ
ルマリン等で還元し金属体として使用に供するこ
とが出来る。 Next, in carrying out the present invention, the catalyst used is palladium or platinum, and although these metals themselves may be used, it is preferable to use them supported on a carrier. In this case, the carrier used may be any ordinary carrier such as activated carbon, silica, alumina, etc. The amount of palladium or platinum supported on such a carrier can range from 0.2 to 20 wt%, preferably from 0.5 to 10 wt%. These catalysts may be prepared by any conventional method, but one example is to immerse the carrier in an aqueous solution of palladium or platinum salt, dry it, and then reduce it with hydrogen, hydrazine, formalin, etc. to prepare it for use as a metal body. can be provided.
本発明は多価アルコールに触媒を懸濁させ反応
させることで実施出来るが、反応に無関係な溶剤
を使用することは好適である。その際用いうる溶
剤としては、テトラヒドロフラン、ジオキサンの
如きエーテル類、アセトニトリルの如きニトリル
類、アルコール類、さらには炭化水素系溶剤等を
用いることができる。 Although the present invention can be carried out by suspending a catalyst in a polyhydric alcohol and causing the reaction, it is preferable to use a solvent unrelated to the reaction. Examples of solvents that can be used in this case include ethers such as tetrahydrofuran and dioxane, nitriles such as acetonitrile, alcohols, and hydrocarbon solvents.
本発明に於ける反応温度は０〜250℃が好まし
く、常温〜200℃が使用される。また圧力は減圧
下、大気圧下、及び加圧下どの状態でも差支えな
いが、反応速度を上げ、生産性を向上させるため
には加圧系が望ましい。なお本発明による反応は
回分式または連続式のいずれでも実施することが
できる。 The reaction temperature in the present invention is preferably 0 to 250°C, and room temperature to 200°C. Further, the pressure may be under reduced pressure, atmospheric pressure, or pressurized, but a pressurized system is preferable in order to increase the reaction rate and improve productivity. The reaction according to the present invention can be carried out either batchwise or continuously.
以下に本発明の実施例を挙げる。 Examples of the present invention are listed below.
実施例 １
１・４ブタンジオール10gr、ジオキサン50c.c.、
及び触媒として市販の５％パラジウム−カーボン
（エンゲルハルド社製）5grを、ガス吹込口、還流
冷却器、撹拌器及び温度計を備えた４つ口フラス
コに入れ、フラスコ内温度を80℃にして、反応液
を充分撹拌しながら、ガス吹込口より空気を10
/Hrで３時間通して反応させた。Example 1 1,4-butanediol 10gr, dioxane 50c.c.,
and 5g of commercially available 5% palladium-carbon (manufactured by Engelhard) as a catalyst were placed in a four-necked flask equipped with a gas inlet, a reflux condenser, a stirrer, and a thermometer, and the temperature inside the flask was raised to 80°C. , While stirring the reaction solution thoroughly, blow in air from the gas inlet for 10 minutes.
/Hr for 3 hours.
反応後の液を分析したところ、１・４ブタンジ
オールの転化率は57％であり、γブチロラクトン
が仕込み１・４ブタンジオールに対して48％の収
率で生成した。 Analysis of the liquid after the reaction revealed that the conversion rate of 1,4-butanediol was 57%, and γ-butyrolactone was produced at a yield of 48% based on the 1,4-butanediol charged.
実施例 ２
１・６ヘキサンジオール15gr、テトラヒドロフ
ラン100c.c.、及び触媒として市販の５％パラジウ
ム−アルミナ（エンゲルハルド社製）5grを、ガ
ス吹込口、撹拌器を付設した容器200c.c.のオート
クレーブに入れ、反応温度を60℃に設定して撹拌
しながら全圧20Kg/cm2、酸素圧４Kg/cm2で酸素の減
量だけ加える方式で反応を行なつた。Example 2 15 gr of 1.6 hexanediol, 100 c.c. of tetrahydrofuran, and 5 gr of commercially available 5% palladium-alumina (manufactured by Engelhard) as a catalyst were placed in a 200 c.c. container equipped with a gas inlet and a stirrer. The mixture was placed in an autoclave, the reaction temperature was set at 60° C., and the reaction was carried out by adding only a reduced amount of oxygen at a total pressure of 20 Kg/cm 2 and an oxygen pressure of 4 Kg/cm 2 while stirring.
反応開始後５時間目で分析したところ、１・６
ヘキサンジオールの転化率は43％、εカプロラク
トンの仕込みヘキサンジオールに対する収率は34
％であつた。 When analyzed 5 hours after the start of the reaction, 1.6
The conversion rate of hexanediol is 43%, and the yield of ε-caprolactone to the charged hexanediol is 34%.
It was %.
実施例 ３
１・５ペンタンジオール5gr、トルエン100c.c.、
及び触媒として５％白金−カーボン（エンゲルハ
ルド社製）5grを実施例１と同じ装置に入れ、温
度60℃、空気10/Hrで５時間反応させた。Example 3 1.5 pentanediol 5gr, toluene 100c.c.,
and 5gr of 5% platinum-carbon (manufactured by Engelhard) as a catalyst were placed in the same apparatus as in Example 1, and reacted for 5 hours at a temperature of 60°C and 10/hr of air.
反応後の液を分析したところ、１・５ペンタン
ジオールの転化率は73％、δバレロラクトンの収
率は61％であつた。 Analysis of the liquid after the reaction revealed that the conversion rate of 1.5 pentanediol was 73% and the yield of δ valerolactone was 61%.
Claims (1)
以上の炭素原子によつて結ばれ、かつそのうちの
１個が第一級アルコールである化合物を、分子状
酸素含有ガスとともにパラジウムまたは白金触媒
に接触させ、上記第一級アルコールのOH基を有
する炭素ともう一方のOH基との間でラクトン化
することを特徴とするラクトンの製造方法。 ２ 出発化合物が、少なくとも４個の直鎖炭素原
子を有するα・ωジオールである特許請求の範囲
第１項記載のラクトンの製造方法。[Claims] 1. A compound having two OH groups, in which the OH groups are connected by four or more carbon atoms, and one of which is a primary alcohol, is defined as a molecule. A method for producing a lactone, which comprises bringing the primary alcohol into contact with a palladium or platinum catalyst together with an oxygen-containing gas, and lactonizing the primary alcohol between a carbon having an OH group and the other OH group. 2. The method for producing lactones according to claim 1, wherein the starting compound is an α-ω diol having at least 4 straight-chain carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9611578A JPS5524107A (en) | 1978-08-09 | 1978-08-09 | Preparation of lactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9611578A JPS5524107A (en) | 1978-08-09 | 1978-08-09 | Preparation of lactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5524107A JPS5524107A (en) | 1980-02-21 |
| JPS6148509B2 true JPS6148509B2 (en) | 1986-10-24 |
Family
ID=14156378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9611578A Granted JPS5524107A (en) | 1978-08-09 | 1978-08-09 | Preparation of lactone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5524107A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2390247A1 (en) | 2010-05-26 | 2011-11-30 | Netherlands Organisation for Scientific Research (Advanced Chemical Technologies for Sustainability) | Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1045174C (en) * | 1994-05-05 | 1999-09-22 | 化学工业部北京化工研究院 | Catalyst for preparing gamma-butyrolactone from 1,4-butanediol by dehydrogenation |
| CN1044866C (en) * | 1994-05-05 | 1999-09-01 | 化学工业部北京化工研究院 | Catalyst for the production of γ-butyrolactone by gas-phase hydrogenation of maleic anhydride |
-
1978
- 1978-08-09 JP JP9611578A patent/JPS5524107A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2390247A1 (en) | 2010-05-26 | 2011-11-30 | Netherlands Organisation for Scientific Research (Advanced Chemical Technologies for Sustainability) | Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde |
| WO2011149339A1 (en) | 2010-05-26 | 2011-12-01 | Netherlands Organisation For Scientific Research (Advanced Chemical Technologies For Sustainability) | Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5524107A (en) | 1980-02-21 |
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