JPH07119182B2 - Method for producing aryl ethylene glycol - Google Patents
Method for producing aryl ethylene glycolInfo
- Publication number
- JPH07119182B2 JPH07119182B2 JP5112073A JP11207393A JPH07119182B2 JP H07119182 B2 JPH07119182 B2 JP H07119182B2 JP 5112073 A JP5112073 A JP 5112073A JP 11207393 A JP11207393 A JP 11207393A JP H07119182 B2 JPH07119182 B2 JP H07119182B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- arylethylene
- catalyst
- glycol
- 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.)
- Expired - Lifetime
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 aryl ethylene glycol Chemical compound 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940100595 phenylacetaldehyde Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 125000003545 alkoxy 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 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
- 238000010304 firing Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C37/00—Component parts, details, accessories or auxiliary operations, not covered by group B29C33/00 or B29C35/00
- B29C37/0003—Discharging moulded articles from the mould
- B29C37/0017—Discharging moulded articles from the mould by stripping articles from mould cores
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C53/00—Shaping by bending, folding, twisting, straightening or flattening; Apparatus therefor
- B29C53/80—Component parts, details or accessories; Auxiliary operations
- B29C53/82—Cores or mandrels
- B29C53/821—Mandrels especially adapted for winding and joining
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はニオブ酸を触媒として利
用する加水分解反応により、アリールエチレンオキサイ
ドを出発原料としてアリールエチレングリコールを製造
する方法に関するものである。本発明によって製造され
るアリールエチレングリコールはフェニルアラニン等の
アミノ酸や香料等を製造するための中間体として有用で
ある。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing arylethylene glycol using arylethylene oxide as a starting material by a hydrolysis reaction using niobate as a catalyst. The aryl ethylene glycol produced by the present invention is useful as an intermediate for producing amino acids such as phenylalanine and perfumes.
【０００２】[0002]
【従来の技術】アリールエチレンオキサイドを相当する
アリールエチレングリコールに変換するためのエポキシ
環の開環加水分解反応は、様々な酸触媒によって進行す
ることが知られており、現在まで主として硫酸を触媒と
して行われているが、生成物の単離や硫酸の処理に問題
が残されている。この点を克服するために、最近では固
体酸触媒を用いる反応についての報告が多い。しかしな
がら、触媒の扱い易さや安定性等の点で多くの問題が残
されている。また、シリカ・アルミナやゼオライト等の
酸化物固体酸触媒は、一般には加水分解反応等の進行す
るような、水の多い反応条件下では活性の低下が大き
く、また加水分解反応以外に異性化や重合等の副反応が
起きやすくなることが知られている。2. Description of the Related Art The ring-opening hydrolysis reaction of an epoxy ring for converting aryl ethylene oxide into a corresponding aryl ethylene glycol is known to proceed with various acid catalysts, and until now, mainly sulfuric acid has been used as a catalyst. However, problems remain with the isolation of the product and the treatment of sulfuric acid. In order to overcome this point, many reports have recently been made on reactions using a solid acid catalyst. However, many problems remain in terms of ease of handling and stability of the catalyst. In addition, an oxide solid acid catalyst such as silica / alumina or zeolite generally has a large decrease in activity under a reaction condition with a large amount of water, such as a hydrolysis reaction, and also causes an isomerization or a reaction other than the hydrolysis reaction. It is known that side reactions such as polymerization easily occur.
【０００３】しかしながら、これら従来の触媒を利用す
る方法は一般的に副反応を充分抑制することが困難であ
り、それらの中で比較的反応成績が良好とされているイ
オン交換樹脂の場合は耐熱性及び耐溶媒性の点で触媒自
体の安定性に問題があった。However, it is generally difficult to sufficiently suppress side reactions in the methods utilizing these conventional catalysts, and in the case of the ion exchange resins which have relatively good reaction results among them, heat resistance is high. There is a problem in the stability of the catalyst itself in terms of the properties and solvent resistance.
【０００４】[0004]
【発明が解決しようとする課題】本発明に於いて、出発
原料及び取得目的物はいずれも反応性に富む物質である
ため、従来の触媒を利用する方法では副反応を抑制する
ことが困難であるか又はある程度抑制し得る場合でも使
用する触媒自体の安定性が劣る等種々の問題があった。In the present invention, since both the starting material and the target substance to be obtained are highly reactive substances, it is difficult to suppress side reactions by the conventional method utilizing a catalyst. There are various problems such as inferior stability of the catalyst itself to be used even if it is present or can be suppressed to some extent.
【０００５】本発明者等は、これら従来の問題を解決
し、緩和な条件で副生物が少なく且つ収率良く目的物を
取得することが出来るような新規な触媒反応を見出すこ
とを目的として種々研究を重ねた結果、ニオブ酸がアリ
ールエチレンオキサイドのエポキシ環に対して非常に選
択特異的な作用を示し、その開環加水分解反応に対して
優れた触媒作用を発揮すると共に、長時間使用しても活
性低下が少なく、取扱の容易な触媒であることを見出
し、本発明を完成した。The inventors of the present invention have variously aimed at solving these conventional problems and finding a novel catalytic reaction which can obtain a target product with a small amount of by-products and a good yield under mild conditions. As a result of repeated research, niobate showed a very selective and specific action on the epoxy ring of arylethylene oxide, and exerted an excellent catalytic action on the ring-opening hydrolysis reaction, and was used for a long time. However, the present invention has been completed by finding that the activity of the catalyst is low and the handling is easy.
【０００６】[0006]
【課題を解決するための手段】本発明は、 (１) アリールエチレンオキサイドを水又は含水溶媒中
でニオブ酸で処理してアリールエチレングリコールを製
造することを特徴とするアリールエチレングリコールの
製造方法。The present invention provides: (1) A method for producing arylethylene glycol, which comprises treating arylethylene oxide with niobic acid in water or a water-containing solvent to produce arylethylene glycol.
【０００７】(２) ニオブ酸が 100〜500℃で焼成処理さ
れたものであることを特徴とする上記 (１) 記載の製造
方法。 に関するものである。本発明の方法は次の化学式で示す
ことが出来る。(2) The production method according to (1) above, wherein the niobic acid is calcined at 100 to 500 ° C. It is about. The method of the present invention can be represented by the following chemical formula.
【０００８】[0008]
【化１】 [Chemical 1]
【０００９】〔但し、式中 R1 , R2 , R3 , R4 及び
R5 はそれぞれ同一又は相異なって、水素原子、ハロゲ
ン原子、アルキル基、アルコキシ基等のような反応に不
活性な置換基を示す。〕本発明に於けるニオブ酸は一般
式 Nb2O5・nH2O (但し、ｎは１〜５の整数を示す) で示
される化合物であり、市販品をそのまま利用することも
出来るが、通常100〜500℃、好ましくは 250〜350℃の
温度で焼成処理して利用する方が良好な結果をもたら
す。ニオブ酸の使用量は反応条件によっても異なるが、
出発原料に対して通常0.001〜１倍モル、好ましくは0.0
5〜0.５倍モルが適当である。[Wherein R 1 , R 2 , R 3 , R 4 and
R 5 s are the same or different and each represents a substituent inert to the reaction, such as a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. The niobic acid in the present invention is a compound represented by the general formula Nb 2 O 5 .nH 2 O (where n represents an integer of 1 to 5), and a commercially available product can be used as it is, Better results are obtained by firing at a temperature of usually 100 to 500 ° C, preferably 250 to 350 ° C. The amount of niobate used varies depending on the reaction conditions,
It is usually 0.001 to 1 times mol, preferably 0.0, relative to the starting material.
A molar amount of 5 to 0.5 is suitable.
【００１０】加水分解反応によりアリールエチレングリ
コールを生成させる場合の溶媒としては水又は含水溶媒
が利用される。含水溶媒を調整する際に水と混合される
溶媒は、均一相の溶液を形成するか否かを問わず、少な
くとも混合された状態で反応温度に於いて液体であるよ
うな不活性液体であればいずれでも使用することが出来
る。Water or a water-containing solvent is used as the solvent when the arylethylene glycol is produced by the hydrolysis reaction. The solvent that is mixed with water when preparing the water-containing solvent should be an inert liquid that is liquid at the reaction temperature at least in the mixed state, regardless of whether or not it forms a homogeneous phase solution. Any of them can be used.
【００１１】例えば、水と混合して均一相を形成する有
機溶媒としてはジオキサンなどの環状エーテル及びアセ
トニトリルが推賞され、水と混合して不均一相を形成す
る有機溶媒としては、ヘキサン等の脂肪族炭化水素及び
ベンゼン、トルエン等の芳香族炭化水素が代表的なもの
として例示される。本発明に於けるアリールエチレング
リコールの取得を目的とする加水分解反応は水中で好適
に進行し、工業的にほぼ満足できる高純度、高収率で進
行するが、適切な含水溶媒 (含水量は通常 10Vol％以
上、好ましくは 50Vol％以上) を利用することによっ
て、この収率を更に向上させ得ることが分った。For example, as an organic solvent which is mixed with water to form a homogeneous phase, cyclic ether such as dioxane and acetonitrile are recommended, and as an organic solvent which is mixed with water to form a heterogeneous phase, a fat such as hexane is used. Typical examples include group hydrocarbons and aromatic hydrocarbons such as benzene and toluene. The hydrolysis reaction for the purpose of obtaining arylethylene glycol in the present invention suitably proceeds in water, and it proceeds with industrially satisfactory high purity and high yield, but a suitable water-containing solvent (water content is It has been found that the yield can be further improved by using 10 vol% or more, preferably 50 vol% or more.
【００１２】含水溶媒中の水含量を低下させれば、目的
とするアリールエチレングリコールの他にアリールアセ
トアルデヒドが副生するようになり、水を全く含まない
有機溶媒を利用すれば、アリールアセトアルデヒドのみ
が高純度、高収率で生成することが分った。本発明に於
いて、溶媒の使用量は出発原料に対し、容量比で通常10
〜1000倍量の範囲で適宜選択され、反応温度は通常溶媒
の沸点に設定するのが好ましい。When the water content in the water-containing solvent is lowered, arylacetaldehyde is produced as a by-product in addition to the intended arylethylene glycol. When an organic solvent containing no water is used, only arylacetaldehyde is produced. It was found that the product was produced in high purity and high yield. In the present invention, the amount of solvent used is usually 10 by volume ratio with respect to the starting material.
The reaction temperature is usually set to the boiling point of the solvent.
【００１３】次にニオブ酸が、従来の触媒に比較して優
れた触媒作用を示すことを説明するために試験例を示
す。 （試験例）容積 300cm3 を反応容器を３ケ使用し、それ
ぞれに水10cm3 、1,４−ジオキサン90cm3 及びスチレン
オキサイド８mmolを添加し、第１の容器にニオブ酸触媒
250mg を添加し、第２の容器にシリカ・アルミナ触媒を
添加し、第３の容器は触媒無添加とした。それぞれの容
器内容物を３時間還流させた後、生成物をガスクロマト
グラフィーにより分析した。Next, test examples will be shown in order to explain that niobic acid exhibits an excellent catalytic action as compared with conventional catalysts. (Test Example) volume 300 cm 3 reaction vessel 3 Ke use, water 10 cm 3, 1,4-dioxane 90cm 3 and styrene oxide 8mmol added to each niobate catalyst in a first container
250 mg was added, a silica-alumina catalyst was added to the second container, and no catalyst was added to the third container. After refluxing the contents of each container for 3 hours, the products were analyzed by gas chromatography.
【００１４】本試験の結果は表１に示す。The results of this test are shown in Table 1.
【００１５】[0015]
【表１】 [Table 1]
【００１６】(*ニオブ酸及びシリカ・アルミナ触媒は、
いずれも 500℃で空気焼成したものを使用した。)表１
の成績から明らかなように、含水溶媒中でスチレンオキ
サイドを加水分解する場合の触媒作用はニオブ酸の方が
シリカ・アルミナよりはるかに優れている。(* Niobate and silica-alumina catalysts are
All were air-baked at 500 ° C. ) Table 1
As is clear from the above results, niobate is far superior to silica-alumina in the catalytic action when hydrolyzing styrene oxide in a water-containing solvent.
【００１７】[0017]
【発明の効果】本発明のニオブ酸を触媒として利用する
方法によれば、アリールエチレンオキサイドのエポキシ
環部位を非常に効率良く加水分解することが出来る。EFFECTS OF THE INVENTION According to the method of using niobic acid as a catalyst of the present invention, the epoxy ring moiety of arylethylene oxide can be hydrolyzed very efficiently.
【００１８】[0018]
【実施例】以下、実施例により本発明を具体的に説明す
る。 （実施例１）100cm3の水及びスチレンオキサイド８mmol
を容積 300cm3 の反応容器にいれ、300℃で空気焼成し
たニオブ酸触媒 250mgとともに２時間還流させた。生成
物をガスクロマトグラフにより分析したところ、7.76mm
olのスチレングリコールが生成していた。 (収率97.0
％) またこの際、副生成物のフェニルアセトアルデヒド
の生成は認められなかった。EXAMPLES The present invention will be specifically described below with reference to examples. (Example 1) 100 cm 3 of water and 8 mmol of styrene oxide
Was placed in a reaction vessel having a volume of 300 cm 3, and the mixture was refluxed for 2 hours together with 250 mg of a niobic acid catalyst calcined in air at 300 ° C. When the product was analyzed by gas chromatography, it was 7.76 mm.
ol styrene glycol was produced. (Yield 97.0
%) Further, at this time, formation of phenylacetaldehyde as a by-product was not observed.
【００１９】（実施例２）50cm3の水、50cm3の１,4−ジ
オキサン及びスチレンオキサイド８mmolを容積 300cm3
の反応容器にいれ、300℃で空気焼成したニオブ酸触媒
250mgとともに２時間還流させた。生成物をガスクロマ
トグラフにより分析したところ、7.95mmolのスチレング
リコールが生成していた。 (収率99％) この際フェニル
アセトアルデヒドは検出されなかった。Example 2 50 cm 3 of water, 50 cm 3 of 1,4-dioxane and 8 mmol of styrene oxide were added to a volume of 300 cm 3
Niobate catalyst placed in a reaction vessel and baked in air at 300 ° C
Reflux with 250 mg for 2 hours. When the product was analyzed by gas chromatography, 7.95 mmol of styrene glycol was formed. (Yield 99%) At this time, phenylacetaldehyde was not detected.
【００２０】上記実施例に於いて、出発原料のアリール
エチレンオキサイドとして、スチレンオキサイドを利用
する例を示したが、本発明はスチレンオキサイドのベン
ゼン環に反応に不活性な置換基が結合している化合物の
場合も同様に実施し得るものである。In the above-mentioned Examples, an example in which styrene oxide was used as the starting arylethylene oxide was shown. In the present invention, a substituent inert to the reaction is bonded to the benzene ring of styrene oxide. The same can be applied to compounds.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 竹内 和彦 茨城県つくば市東１丁目１番地 工業技術 院化学技術研究所内 (72)発明者 荒川 裕則 茨城県つくば市東１丁目１番地 工業技術 院化学技術研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazuhiko Takeuchi, 1-1, Higashi, Tsukuba-shi, Ibaraki Industrial Technology Institute, Institute of Chemical Technology (72) Inventor, Hironori Arakawa, 1-1, East, Tsukuba-shi, Ibaraki Industrial Technology In the laboratory
Claims (2)
水溶媒中でニオブ酸で処理してアリールエチレングリコ
ールを製造することを特徴とするアリールエチレングリ
コールの製造方法。1. A method for producing arylethylene glycol, which comprises treating arylethylene oxide with niobic acid in water or a water-containing solvent to produce arylethylene glycol.
たものであることを特徴とする請求項１記載の製造方
法。2. The manufacturing method according to claim 1, wherein the niobic acid is calcined at 100 to 500 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5112073A JPH07119182B2 (en) | 1993-04-15 | 1993-04-15 | Method for producing aryl ethylene glycol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5112073A JPH07119182B2 (en) | 1993-04-15 | 1993-04-15 | Method for producing aryl ethylene glycol |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1225085A Division JPH0390042A (en) | 1989-08-31 | 1989-08-31 | Method for treating arylethylene oxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06179633A JPH06179633A (en) | 1994-06-28 |
| JPH07119182B2 true JPH07119182B2 (en) | 1995-12-20 |
Family
ID=14577400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5112073A Expired - Lifetime JPH07119182B2 (en) | 1993-04-15 | 1993-04-15 | Method for producing aryl ethylene glycol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07119182B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100413578C (en) * | 2004-09-24 | 2008-08-27 | 中国石油化工股份有限公司 | Niobium Oxide Catalyst for Preparation of Ethylene Glycol by Hydration of Ethylene Oxide |
| CN100413579C (en) * | 2004-09-24 | 2008-08-27 | 中国石油化工股份有限公司 | Catalyst for hydration of ethylene oxide to prepare ethylene glycol |
| CN1318365C (en) * | 2004-10-29 | 2007-05-30 | 中国石油化工股份有限公司 | Aryl dihydroxy alcohol preparation method |
| JP4961722B2 (en) * | 2004-12-13 | 2012-06-27 | 住友化学株式会社 | Method for producing alcohols |
-
1993
- 1993-04-15 JP JP5112073A patent/JPH07119182B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06179633A (en) | 1994-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |