JPH0459742A - Production of 2,2-bis(4-oxocyclohexyl)propane - Google Patents
Production of 2,2-bis(4-oxocyclohexyl)propaneInfo
- Publication number
- JPH0459742A JPH0459742A JP16672590A JP16672590A JPH0459742A JP H0459742 A JPH0459742 A JP H0459742A JP 16672590 A JP16672590 A JP 16672590A JP 16672590 A JP16672590 A JP 16672590A JP H0459742 A JPH0459742 A JP H0459742A
- Authority
- JP
- Japan
- Prior art keywords
- propane
- bis
- raw material
- solvent
- oxidizing agent
- 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
- HAWVCXABNZBPED-UHFFFAOYSA-N 4-[2-(4-oxocyclohexyl)propan-2-yl]cyclohexan-1-one Chemical compound C1CC(=O)CCC1C(C)(C)C1CCC(=O)CC1 HAWVCXABNZBPED-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000001294 propane Substances 0.000 claims description 10
- -1 4-hydroxycyclohexyl Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 24
- 239000002994 raw material Substances 0.000 abstract description 13
- 239000007800 oxidant agent Substances 0.000 abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- 238000003756 stirring Methods 0.000 abstract description 7
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 150000007524 organic acids Chemical class 0.000 abstract description 4
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 230000003078 antioxidant effect Effects 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000047 product Substances 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229940090961 chromium dioxide Drugs 0.000 description 5
- IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 5
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は２，２−ビス（４−オキソシクロヘキシル）プ
ロパンの製造法に間するものである。詳しくは、２．２
−ビス（４−ヒドロキシシクロヘキシル）プロパンを酸
化することにより２，２−ビス（４−オキソシクロヘキ
シル）プロパンを製造する方法の改良に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing 2,2-bis(4-oxocyclohexyl)propane. For details, see 2.2
The present invention relates to an improvement in a method for producing 2,2-bis(4-oxocyclohexyl)propane by oxidizing -bis(4-hydroxycyclohexyl)propane.
（従来の技術）
２．２−ビス（４−オキソシクロヘキシル）プロパンは
、ポリマーの原料、酸化防止剤、熱安定化剤等の中間体
として有用であり、従来その製造法としては二酸化クロ
ムを用いて２．２−ビス（４−ヒドロキシシクロヘキシ
ル）プロパンを酸化する方法が一般的である［ Ｂｕｔ
１．Ｃｈｅｗ、Ｓｏｃ、Ｊａｐａｎ、３９（１０）、
２１９４（１９６６）］。(Prior art) 2.2-Bis(4-oxocyclohexyl)propane is useful as a raw material for polymers, an antioxidant, a heat stabilizer, etc., and the conventional method for producing it has been to use chromium dioxide. A common method is to oxidize 2,2-bis(4-hydroxycyclohexyl)propane [But
1. Chew, Soc, Japan, 39(10),
2194 (1966)].
しかしこの方法では、目的物の収率、純度ともに充分満
足し得るものでなく、また酸化剤の二酸化クロムは有害
であるため、作業環境の管理や、残留二酸化クロム無害
化の適切な措置を講する等の充分な配慮が必要である。However, this method does not fully satisfy both the yield and purity of the target product, and the oxidizing agent chromium dioxide is harmful, so appropriate measures must be taken to manage the working environment and make residual chromium dioxide harmless. It is necessary to take sufficient consideration such as
（発明が解決しようとする課題）
本発明は上記従来、法による問題点を解決し、高純度の
目的物を収率よく製造し得ると共に、作業環境に格別の
留意を払うことなく、工業的に有利に２，２−ビス（４
−オキソシクロヘキシル）プロパンを製造することを目
的とするものである。(Problems to be Solved by the Invention) The present invention solves the above-mentioned problems with the conventional methods, enables the production of high-purity target products with good yield, and enables industrial use without paying special attention to the working environment. 2,2-bis(4
-Oxocyclohexyl)propane.
（課題を解決するための手段）
本□発明者等は上記の目的を達成するために検討を重ね
た結果、２，２−ビス（４−ヒドロキシシクロヘキシル
）プロパンを酸化することにより２，２−ビス（４−オ
キソシクロヘキシル）プロパンを製造する際に、ある種
の酸化剤を使用するときは、極めて高純度の目的物が収
率よく得られることを見い出し、本発明を達成した。即
ち本発明の要旨は、２，２−ビス（４−ヒドロキシシク
ロヘキシル）プロパンを溶媒の存在下において、次亜ハ
ロゲン酸もしくはその塩又はハロゲンにより酸化するこ
とを特徴とする２゜２−ビス（４−オキソシクロヘキシ
ル）プロパンの製造法に存する。(Means for Solving the Problems) As a result of repeated studies to achieve the above object, the inventors have found that by oxidizing 2,2-bis(4-hydroxycyclohexyl)propane, 2,2- The present invention has been achieved by discovering that when a certain type of oxidizing agent is used in the production of bis(4-oxocyclohexyl)propane, a target product of extremely high purity can be obtained in good yield. That is, the gist of the present invention is to oxidize 2,2-bis(4-hydroxycyclohexyl)propane with hypohalous acid or a salt thereof or a halogen in the presence of a solvent. -oxocyclohexyl)propane.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の原料として使用される２、２−ビス（４−ヒド
ロキシシクロヘキシル）プロパンは、水素化ビスフェノ
ールＡの名で慣用され、一般にビスフェノールＡ ［２
，２−ビス（４−ヒドロキシフェニル）プロパン］を核
水素化することによって得られる。本物質には３種類の
立体異性体が存在するが、本発明においては、それらを
単独で、あるいは混合物のままで原料に使用す・ること
かできる。2,2-bis(4-hydroxycyclohexyl)propane used as a raw material in the present invention is commonly used as hydrogenated bisphenol A, and is generally referred to as bisphenol A [2
, 2-bis(4-hydroxyphenyl)propane] by nuclear hydrogenation. There are three stereoisomers of this substance, and in the present invention, they can be used alone or as a mixture as a raw material.
本発明における酸化剤としては、次亜塩素酸、次亜臭素
酸のような次亜ハロゲン酸、又はこれらの塩類、例えば
ナトリウム塩、カリウム塩、カルシウム塩等が挙げられ
、これらは水溶液又は粉末で使用される。その他塩素の
ようなハロゲンを使用することもてきる。酸化剤の使用
量は、原料物質に対して２〜３倍モル程度が好適であり
、酸化剤の使用量が過大であると副生物が生成し易く、
また過小であると目的物の収率の低下を招く。特に好ま
しい酸化剤の量は２．１〜２．３倍モルである。Examples of the oxidizing agent in the present invention include hypohalous acids such as hypochlorous acid and hypobromous acid, and salts thereof such as sodium salts, potassium salts, and calcium salts, which can be used in aqueous solution or powder form. used. Other halogens such as chlorine can also be used. The amount of oxidizing agent used is preferably about 2 to 3 times the mole of the raw material, and if the amount of oxidizing agent used is excessive, by-products are likely to be generated.
Moreover, if it is too small, the yield of the target product will decrease. A particularly preferred amount of the oxidizing agent is 2.1 to 2.3 times the mole.
なお、次亜ハロゲン酸の塩類を使用する場合には、酢酸
、蓚酸等の有機酸又は塩酸、硫酸等の鉱酸を、原料の２
，２−ビス（４−ヒドロキシシクロヘキシル）プロパン
に対して通常２倍当量以上の量で併用することが必要で
あり、中でも有機酸を使用するのが、目的の収率、純度
を向上させる上で特に好ましい、また、酢酸のような有
機酸は溶媒を兼ねることができる。In addition, when using salts of hypohalous acid, organic acids such as acetic acid and oxalic acid or mineral acids such as hydrochloric acid and sulfuric acid are added to the raw materials.
, 2-bis(4-hydroxycyclohexyl)propane, it is necessary to use them together in an amount of 2 times or more equivalents, and in particular, it is recommended to use organic acids in order to improve the desired yield and purity. Particularly preferred, organic acids such as acetic acid can also serve as a solvent.
本発明に使用される溶媒としては、上記の酸化剤と反応
し難いものであって、−船釣には、原料物質の溶解性が
高いものが望ましい。具体的には例えば、メタノール、
酢酸、トルエン、クロロベンゼン、ジオキサンや、これ
らを含む混合溶媒が挙げられる。この際、水が溶媒中に
存在してもよいが、水は原料物質及び目的物を溶解しな
いので、多量に存在させることは好ましくない。The solvent used in the present invention is preferably one that does not easily react with the above-mentioned oxidizing agent and, for boat fishing, has a high solubility for the raw material. Specifically, for example, methanol,
Examples include acetic acid, toluene, chlorobenzene, dioxane, and mixed solvents containing these. At this time, water may be present in the solvent, but since water does not dissolve the raw material and the target substance, it is not preferable to have it present in a large amount.
なお、酢酸やメタノールのような目的物の溶解性が小さ
い溶媒を使用すると、反応中に攪拌が困難となることが
あるが、この場合にはクロロベンゼンのような目的物の
溶解性の大きい溶媒を併用し、かつ周知の相間移動触媒
例えばテトラブチルアンモニウムブロマイドを使用すれ
ば、２層系の溶解した状態となり、攪拌を容易にし、か
つ相間移動触媒の効果により反応を良好に行うことがで
きる。Note that if a solvent with a low solubility of the target product, such as acetic acid or methanol, is used, stirring may become difficult during the reaction, but in this case, a solvent with a high solubility of the target product, such as chlorobenzene, may be used. When used in combination with a well-known phase transfer catalyst such as tetrabutylammonium bromide, a two-layer system is formed in a dissolved state, which facilitates stirring and allows the reaction to be carried out favorably due to the effect of the phase transfer catalyst.
酸化反応は、上記の原料物質を溶媒中に溶解もしくは懸
濁させ、次いで０℃乃至溶媒の沸点以下の温度、好まし
くは１０〜４０℃程度で攪拌しながら、所要量の酸化剤
を添加することにより実施される。The oxidation reaction is carried out by dissolving or suspending the above raw material in a solvent, and then adding the required amount of oxidizing agent while stirring at a temperature of 0°C to below the boiling point of the solvent, preferably about 10 to 40°C. Implemented by
反応終了後、析出した生成物を濾取すれば高純度の目的
とする２、２−ビス（４−オキソシクロヘキシル）プロ
パンを収率よく得ることができる。なお生成物が溶媒中
に溶解しているときは濃縮して析出させ、濾過すればよ
い。After the reaction is completed, the precipitated product is collected by filtration to obtain highly purified target 2,2-bis(4-oxocyclohexyl)propane in good yield. Note that when the product is dissolved in the solvent, it may be concentrated to precipitate it and then filtered.
（実施例）
以下に本発明を実施例により更に詳細に説明するが、本
発明はその要旨を超えない限り、以下の実施例に限定さ
れるものではない。(Examples) The present invention will be explained in more detail by Examples below, but the present invention is not limited to the following Examples unless it exceeds the gist thereof.
実施例１
２．２−ビス（４−ヒドロキシシクロヘキシル）プロパ
ン２４ ｇ（０，１モル）を酢酸９６ ｇに溶解し、次
いで攪拌しながら温度を２０〜３０℃に保持しつつ、１
３％の次亜塩素酸ナトリウム水溶液１２０ ｇ（０，２
２モル）を徐々に添加して酸化反応を行った。反応終了
後、析出した結晶を濾取し、水洗、乾燥して融点１６３
℃の２．２−ビス（４−オキソシクロヘキシル）プロパ
ン２０ ｇを得た。収率は８５％であり、本物質のガス
クロマトグラフィーによる純度は９８％であった。Example 1 24 g (0.1 mol) of 2.2-bis(4-hydroxycyclohexyl)propane was dissolved in 96 g of acetic acid, and then 1 was added while stirring and maintaining the temperature at 20-30°C.
120 g of 3% sodium hypochlorite aqueous solution (0,2
2 mol) was gradually added to carry out the oxidation reaction. After the reaction, the precipitated crystals were collected by filtration, washed with water, and dried to a melting point of 163.
20 g of 2.2-bis(4-oxocyclohexyl)propane at a temperature of 2.0°C was obtained. The yield was 85%, and the purity of this material by gas chromatography was 98%.
実施例２
２．２−ビス（４−ヒドロキシシクロヘキシル）プロパ
ン２４ ｇ（０，１％ ル）ラメ９ ／ −ル１２０
ｍｌ及び酢［１８ｇ（０，３モル）の混合液に溶解し、
以下実施例１におけると同様に１３％次亜塩素酸ナトリ
ウム水溶液１２０ ｇを添加して酸化反応を行った０反
応終了後、析出した結晶を濾取し、水洗、乾燥して２．
２−ビス（４−オキソシクロヘキシル）プロパン２０
ｇを得た。Example 2 2.2-bis(4-hydroxycyclohexyl)propane 24 g (0.1%) 9/120
ml and vinegar [18 g (0.3 mol) dissolved in a mixture of
Thereafter, in the same manner as in Example 1, 120 g of a 13% sodium hypochlorite aqueous solution was added to perform an oxidation reaction. After the reaction was completed, the precipitated crystals were collected by filtration, washed with water, and dried.
2-bis(4-oxocyclohexyl)propane 20
I got g.
収率は８５％であり、純度は９８％であった。The yield was 85% and the purity was 98%.
実施例３
実施例２で使用した１３％次亜塩素酸ナトリウム水溶液
の代りに、３５％次亜塩素酸カルシウム（高度サラシ粉
）５０ ｇ（０−１モル）を使用した以外は実施例２と
同様にして酸化反応を行って２，２−ビス（４−オキソ
シクロヘキシル）プロパン１８ ｇを得た。収率は７７
％であり、純度は９７．８％であった。Example 3 Same as Example 2 except that 50 g (0-1 mol) of 35% calcium hypochlorite (advanced white powder) was used instead of the 13% aqueous sodium hypochlorite solution used in Example 2. An oxidation reaction was carried out in the same manner to obtain 18 g of 2,2-bis(4-oxocyclohexyl)propane. Yield is 77
%, and the purity was 97.8%.
実施例４
２．２−ビス（４−ヒドロキシシクロヘキシル）プロパ
ン２４ ｇ（０，１モル）及び０．８ ｇ（１，８８ミ
リモル）のテトラブチルアンモニウムブロマイド（相間
移動触媒）を、酢酸２４ ｇ（０，４モル）及びクロロ
ベンゼン１００■１の混合液に添加し、攪拌しながら温
度を約３０℃に保持しつつ、１３％の次亜塩＊＊ナトリ
ウム水溶液１２０ ｇ（０，２２モル）を徐々に添加し
て酸化反応を行つた０反応終了後、分液して油層（クロ
ロベンゼン層）を採取し、中和、水洗して濃縮し、析出
した結晶を濾取し乾燥して２，２−ビス（４−オキソシ
クロヘキシル）プロパン１９．５ ｇを得た。この場合
攪拌が順調に行われた。収率は８３％であり、純度は９
８％であった。Example 4 24 g (0.1 mol) of 2.2-bis(4-hydroxycyclohexyl)propane and 0.8 g (1.88 mmol) of tetrabutylammonium bromide (phase transfer catalyst) are mixed with 24 g of acetic acid ( 0.4 mol) and 100 x 1 chlorobenzene, and while stirring and maintaining the temperature at about 30°C, gradually added 120 g (0.22 mol) of a 13% sodium hypochlorite solution (0.22 mol). After the completion of the oxidation reaction, the oil layer (chlorobenzene layer) was separated, neutralized, washed with water and concentrated, and the precipitated crystals were collected by filtration and dried to give 2,2- 19.5 g of bis(4-oxocyclohexyl)propane was obtained. In this case, stirring was performed smoothly. The yield is 83% and the purity is 9
It was 8%.
（発明の効果）
本発明の方法によれば、極めて高純度の目的物を収率よ
く得ることができる。しかも、従来の有害な二酸化クロ
ムを使用する場合に伴う作業環境の管理や、残留二酸化
クロム無言化の配慮などを必要としないので、工業的実
施上極めて有利である。(Effects of the Invention) According to the method of the present invention, a target product of extremely high purity can be obtained in good yield. In addition, it is extremely advantageous in industrial practice because it does not require the management of the working environment or the consideration to eliminate residual chromium dioxide, which is required when using conventional harmful chromium dioxide.
Claims (1)
プロパンを溶媒の存在下において、次亜ハロゲン酸もし
くはその塩又はハロゲンにより酸化することを特徴とす
る２，２−ビス（４−オキソシクロヘキシル）プロパン
の製造法。(1) 2,2-bis(4-hydroxycyclohexyl)
A method for producing 2,2-bis(4-oxocyclohexyl)propane, which comprises oxidizing propane with hypohalous acid, a salt thereof, or a halogen in the presence of a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16672590A JPH0459742A (en) | 1990-06-27 | 1990-06-27 | Production of 2,2-bis(4-oxocyclohexyl)propane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16672590A JPH0459742A (en) | 1990-06-27 | 1990-06-27 | Production of 2,2-bis(4-oxocyclohexyl)propane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0459742A true JPH0459742A (en) | 1992-02-26 |
Family
ID=15836597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16672590A Pending JPH0459742A (en) | 1990-06-27 | 1990-06-27 | Production of 2,2-bis(4-oxocyclohexyl)propane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0459742A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0697389A1 (en) | 1994-08-09 | 1996-02-21 | New Japan Chemical Co.,Ltd. | Process for producing alicyclic diketone compounds |
| WO1998000382A1 (en) * | 1996-07-02 | 1998-01-08 | Toray Industries, Inc. | Processes for the preparation of optically active ketones |
| US6313351B1 (en) | 1999-07-15 | 2001-11-06 | Honshu Chemical Industry Co., Ltd. | Process for producing alicyclic monoketones and process for producing alicyclic diketones |
-
1990
- 1990-06-27 JP JP16672590A patent/JPH0459742A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0697389A1 (en) | 1994-08-09 | 1996-02-21 | New Japan Chemical Co.,Ltd. | Process for producing alicyclic diketone compounds |
| WO1998000382A1 (en) * | 1996-07-02 | 1998-01-08 | Toray Industries, Inc. | Processes for the preparation of optically active ketones |
| US6320069B1 (en) * | 1996-07-02 | 2001-11-20 | Toray Industries, Inc. | Production of optically active ketone |
| US6313351B1 (en) | 1999-07-15 | 2001-11-06 | Honshu Chemical Industry Co., Ltd. | Process for producing alicyclic monoketones and process for producing alicyclic diketones |
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