JPH02196778A - Method for preventing discoloration of maleic anhydride - Google Patents
Method for preventing discoloration of maleic anhydrideInfo
- Publication number
- JPH02196778A JPH02196778A JP1013985A JP1398589A JPH02196778A JP H02196778 A JPH02196778 A JP H02196778A JP 1013985 A JP1013985 A JP 1013985A JP 1398589 A JP1398589 A JP 1398589A JP H02196778 A JPH02196778 A JP H02196778A
- Authority
- JP
- Japan
- Prior art keywords
- maleic anhydride
- color
- synthetic
- compound
- zinc chloride
- 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.)
- Granted
Links
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002845 discoloration Methods 0.000 title claims abstract description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 18
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 11
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 11
- 229940045803 cuprous chloride Drugs 0.000 claims abstract description 11
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 9
- 239000011592 zinc chloride Substances 0.000 claims abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 230000006866 deterioration Effects 0.000 abstract description 2
- 239000002649 leather substitute Substances 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 229920003051 synthetic elastomer Polymers 0.000 abstract description 2
- 239000012209 synthetic fiber Substances 0.000 abstract description 2
- 229920002994 synthetic fiber Polymers 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 239000005061 synthetic rubber Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract 2
- 235000010388 propyl gallate Nutrition 0.000 abstract 2
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000003381 stabilizer Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は無水マレイン酸の加熱溶融時に於ける熱安定性
を向上し着色を防止する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for improving the thermal stability and preventing discoloration of maleic anhydride during heating and melting.
無水マレイン酸はベンゼン又は炭素数４の炭化水素留分
（以下Ｃ４留分と記す）を接触酸化して得られる代表的
な不飽和二塩基酸であり、２個のカルボキシル基を酸無
水物の形で有し、他に反応性の大きい二重結合を有して
いるので化学的に様々の反応を行うことが出来、合成ゴ
ム、可塑剤、合成樹脂、接着剤、合成繊維、合成皮革、
農薬等の原料として広く使用される有用な物質である、
この無水マレイン酸の一般的な製造方法は、ベンゼン又
はＣ４留分を触媒を用いて接触気相酸化し、得られた粗
生成物を蒸留によって精製し無水マレイン酸を得るもの
である。Maleic anhydride is a typical unsaturated dibasic acid obtained by catalytic oxidation of benzene or a hydrocarbon fraction with 4 carbon atoms (hereinafter referred to as C4 fraction), and two carboxyl groups are replaced by the acid anhydride. In addition, it has highly reactive double bonds, so it can undergo various chemical reactions, such as synthetic rubber, plasticizers, synthetic resins, adhesives, synthetic fibers, synthetic leather,
It is a useful substance widely used as a raw material for agricultural chemicals, etc.
A common method for producing maleic anhydride is to subject benzene or a C4 fraction to catalytic gas phase oxidation using a catalyst, and refine the resulting crude product by distillation to obtain maleic anhydride.
しかしながら精製した無水マレイン酸においても酸化副
生成物等の除去困難な不純物を微量含んでおり、そのた
め熱安定性に欠は加熱溶融時に着色すると言う傾向があ
り、特に長期間保存した場合に於いてこの傾向が著しい
、そしてこの加熱溶融時の着色性は、無水マレイン酸を
原料とする各種二次製品の品質と大いに関係しこれらの
商品価値を著しく損なう結果となる。However, even purified maleic anhydride contains small amounts of impurities such as oxidation by-products that are difficult to remove, and as a result, it lacks thermal stability and tends to become colored when heated and melted, especially when stored for a long period of time. This tendency is remarkable, and the coloring property upon heating and melting is closely related to the quality of various secondary products made from maleic anhydride as a raw material, resulting in a significant loss of their commercial value.
従って、工業原料としての無水マレイン酸には加熱溶融
による着色現象を起こさない事が厳しく要求されている
。Therefore, maleic anhydride as an industrial raw material is strictly required not to cause any coloring phenomenon due to heating and melting.
この様な状況に於いて、着色防止のために従来から種々
の方法が提案されてきている、例えば特公昭４１−１９
４０５号に於いては、無水マレイン酸に対して一般式
０Ｈ
（式中Ｒ，は■又はＯＨ，Ｒｔは
ｚ
で表される化合物を添加し、更にこれに亜鉛、銅、アル
ミニウム或いはその酸化物又はその塩類を添加して熱安
定性を改善する方法が示されている、叉、特公昭４７−
２６７６６号では無水マレイン酸に対し、ハイドロキノ
ンと銅もしくはモリブデンの単体もしくは化合物又はこ
れらの混合物を添加して加熱溶融色を安定化する方法が
示されている。Under these circumstances, various methods have been proposed to prevent coloring, such as the Japanese Patent Publication No. 41-19
In No. 405, a compound represented by the general formula 0H (in the formula R, Or, a method of improving thermal stability by adding salts thereof is shown, and Japanese Patent Publication No. 47-
No. 26766 discloses a method of stabilizing the heat-melted color by adding hydroquinone, copper or molybdenum alone or a compound, or a mixture thereof to maleic anhydride.
更に、特公昭５７−５１３９３号では精製マレイン酸に
有機リン酸ポリエステル類とフルオホウ酸金属塩類、金
属銅及び銅化合物を添加する色安定化法が示されている
、その他、特開昭４９−１１６０２３号の無水マレイン
酸に対して亜リン酸エステル又は、亜リン酸エステルと
金属ハロゲン化物とを共に添加することにより無水マレ
イン酸の熱安定性を改善せしめる方法、特開昭４８−２
３７１９号の無水マレイン酸に対してチオ燐酸ハイドロ
カーピノールを添加することにより高温における無水マ
レイン酸の着色度を安定化する方法、等が知られている
。Furthermore, Japanese Patent Publication No. 57-51393 discloses a color stabilization method in which organic phosphoric acid polyesters, fluoboric acid metal salts, metallic copper, and copper compounds are added to purified maleic acid. A method for improving the thermal stability of maleic anhydride by adding a phosphite or a phosphite and a metal halide to maleic anhydride, JP-A-48-2
No. 3719, a method of stabilizing the degree of coloration of maleic anhydride at high temperatures by adding hydrocarpinol thiophosphate to maleic anhydride is known.
〔発明が解決しようとする課題］
しかしながら、これらの従来技術による方法では昨今の
厳しい品質要求に対しては何れも充分な結果を得る事が
出来ない。[Problems to be Solved by the Invention] However, none of these conventional methods can provide sufficient results to meet the recent strict quality requirements.
無水マレイン酸の色安定化の機構はまだ充分に解明され
ておらず、いまも優れた色安定化方法の探索が行われて
おり、加熱溶融色の良好な、然も無水マレイン酸を熔融
状悪文は固化して長期間ストックしておいた場合でも色
安定性を良好に保つ方法が求められている。The color stabilization mechanism of maleic anhydride has not yet been fully elucidated, and the search for an excellent color stabilization method is still ongoing. There is a need for a method to maintain good color stability even when bad writing is solidified and stored for a long period of time.
〔課題を解決するための手段］
本発明者らは上記問題点につき鋭意研究を行った結果本
発明に到達したものである。[Means for Solving the Problems] The present inventors have arrived at the present invention as a result of intensive research into the above-mentioned problems.
即ち、本発明の無水マレイン酸の着色防止方法は無水マ
レイン酸に対して重量比で没食子酸ｎ−プロピルエステ
ルを１〜１１００ｐｐ、塩化第一銅を０．１〜５ｐｐｍ
、更に塩化亜鉛を０．１〜５ｐｐｍ添加することを特徴
とするものである０本発明に於ける安定剤の添加方法は
、特に限定はされないが例えば蒸留工程から留出した精
製無水マレイン酸或いは溶融状態で貯蔵している無水マ
レイン酸に添加混合攪拌することにより実施される。添
加方法は、没食子酸ｎ−プロピルエステルと塩化第一銅
を各々単独に何れを先に添加しても良く、叉予め混合し
て添加しても良い、次いで塩化亜鉛をそのまま直接添加
しても良く、水、有機溶媒例えばエタノール等に溶解し
て添加しても良い、その何れの方法においても目的とす
る効果が確実に得られる。安定剤の添加量は、重量比で
無水マレイン酸に対して、没食子酸ｎ−プロピルエステ
ルは１〜１００ｐｔｎの範囲と塩化第一銅は０．１〜５
ｐｐｍの範囲が適当であり、更に塩化亜鉛を０．１〜ｓ
ｐｐｍの範囲で適量を選択すれば良い。That is, the method for preventing discoloration of maleic anhydride of the present invention uses gallic acid n-propyl ester in a weight ratio of 1 to 1100 ppm and cuprous chloride in a weight ratio of 0.1 to 5 ppm to maleic anhydride.
The method of adding the stabilizer in the present invention is not particularly limited, but for example, purified maleic anhydride distilled from a distillation process or This is carried out by adding to maleic anhydride stored in a molten state and stirring. As for the addition method, gallic acid n-propyl ester and cuprous chloride may be added individually first, or they may be mixed in advance, or zinc chloride may be added directly as is. Alternatively, it may be added after being dissolved in water or an organic solvent such as ethanol. Either method will ensure that the desired effect will be obtained. The amount of stabilizer added is in the range of 1 to 100 ptn for gallic acid n-propyl ester and 0.1 to 5 ptn for cuprous chloride to maleic anhydride in terms of weight ratio.
ppm is appropriate, and zinc chloride is added in a range of 0.1 to s.
An appropriate amount may be selected within the ppm range.
没食子酸ｎ−プロピルエステルと塩化第一銅を組み合わ
せる色安定剤は特公昭４１−１９４０５に於いて既に提
案されているが、前述の如くこの組み合わせでは現在要
求されている加熱溶融時に於ける熱安定性と着色防止に
は未だ不充分であり、本発明者らは種々実験の結果、没
食子酸ｎ−プロピルエステルと塩化第一銅にさらに塩化
亜鉛を組み合わせることにより驚くべきことに極めて顕
著な熱安定性を得ることが出来たものである。没食子酸
ｎ−プロピルエステルと塩化第一銅の組み合わせの場合
、後述の比較例で示すように添加量を増加しても本発明
の水準よりもはるかに劣り、塩化亜鉛単独でみても同様
である。しかも多量の安定剤を使用することは無水マレ
イン酸の品質、特に化学的性質上不純物として好ましく
ない。A color stabilizer combining gallic acid n-propyl ester and cuprous chloride has already been proposed in Japanese Patent Publication No. 41-19405, but as mentioned above, this combination does not provide the currently required thermal stability during heating and melting. However, as a result of various experiments, the present inventors surprisingly achieved extremely remarkable thermal stability by combining gallic acid n-propyl ester, cuprous chloride, and zinc chloride. I was able to obtain my sexuality. In the case of the combination of gallic acid n-propyl ester and cuprous chloride, as shown in the comparative example below, even if the amount added is increased, it is far inferior to the level of the present invention, and the same is true when looking at zinc chloride alone. . Furthermore, it is not preferable to use a large amount of stabilizer because it may cause impurities due to the quality of maleic anhydride, especially its chemical properties.
本発明による色安定化剤の添加量は微量で充分な効果を
得るものであり、無水マレイン酸の品質上何らの悪影響
も及ぼすことは無く、従ってこの無水マレイン酸を原料
とした２次加工製品に対しても何らの障害も与えること
は無い。The color stabilizer according to the present invention can be added in a small amount to achieve a sufficient effect, and will not have any adverse effect on the quality of maleic anhydride. Therefore, secondary processed products using this maleic anhydride as a raw material It does not pose any hindrance to the.
以下、実施例により本発明の方法を更に具体的に説明す
る。Hereinafter, the method of the present invention will be explained in more detail with reference to Examples.
尚実施例に示すｐｐｍは重量単位により示したものであ
る。Note that the ppm shown in the examples is expressed in weight units.
叉、「溶融色ＪとはＪＩＳＫ−１３５９により溶融時の
色相をＡＰＩ！Ａ表示したものであり、「加熱溶融色」
とは無水マレイン酸を入れた直径約２０＋ａｍ、高さ１
５０ｗ−の石英製試験管（ＪＩＳＫ−１３５９溶融色測
定に用いたものと同型）を１８１°Ｃに調節された油浴
に６０分間浸漬加熱した後の色相をＡＰ）ＩＡにより表
示したものである。``Melting color J'' is an API!A representation of the hue at the time of melting according to JISK-1359, and is ``heat melting color.''
is about 20+ am in diameter and 1 in height containing maleic anhydride.
The hue after immersing and heating a 50W quartz test tube (same type as the one used in JISK-1359 melt color measurement) in an oil bath adjusted to 181°C for 60 minutes is displayed by AP)IA. .
実施例Ｉ
Ｃ４留分の接触酸化反応で得られた粗無水マレイン酸を
蒸留により精製して得られた溶融無水マレイン酸に、没
食子酸ｎ−プロピルエステルと塩化第一銅さらに塩化亜
鉛をそれぞれ所定量添加し均一に撹拌混合した後、石英
試験管に採り溶融色及び加熱溶融色を測定した。添加量
の一部を変化させた結果を第１表に示す。Example I Gallic acid n-propyl ester, cuprous chloride, and zinc chloride were added to molten maleic anhydride obtained by purifying crude maleic anhydride obtained by catalytic oxidation reaction of C4 fraction by distillation. After adding a fixed amount and stirring and mixing uniformly, the mixture was taken into a quartz test tube and the melting color and heating melting color were measured. Table 1 shows the results obtained by partially changing the amount added.
比較例１
他の安定剤の組み合わせにより実施例１と同様の方法で
溶融色及び加熱溶融色を測定して得た結果を第２表に示
す。Comparative Example 1 Table 2 shows the results obtained by measuring the melting color and heating melting color in the same manner as in Example 1 using a combination of other stabilizers.
実施例２
実施例１と同様の方法で安定剤を添加し、経口変化を知
るために各安定剤を添加した試料を液状（６５°Ｃ）及
び固体状で３０日間ストンクした場合について、それぞ
れ溶融色と加熱溶融色とを測定した結果を第３表に示す
。Example 2 Stabilizers were added in the same manner as in Example 1, and samples to which each stabilizer was added were stonked in liquid (65°C) and solid form for 30 days in order to determine oral changes. Table 3 shows the results of measuring the color and heat melting color.
（発明の効果〕
本発明の方法に於いては、従来知られていた没食子酸ｎ
−プロピルエステルと塩化第一銅の組み合わせに更に塩
化亜鉛を組み合わせる事により無水マレイン酸の高温溶
融色の色相を従来者えられなかった程度に低下させるこ
とが出来る、叉、溶融ストック時における経時的色相劣
化をも大幅に抑制することができる。然もこれら添加剤
の添加量も少量で充分その効果を得ることが出来るため
、製品への不純物的影響は皆無であり、無水マレイン酸
の高品質化に寄与すること大である。(Effects of the Invention) In the method of the present invention, the conventionally known gallic acid n
-By further combining zinc chloride with the combination of propyl ester and cuprous chloride, it is possible to reduce the hue of the high temperature melting color of maleic anhydride to a degree that was previously unachievable, and also to reduce the hue over time during melt stocking. Hue deterioration can also be significantly suppressed. However, since the effects of these additives can be sufficiently obtained even in small amounts, there is no impurity effect on the product, and they greatly contribute to improving the quality of maleic anhydride.
特許出願人 三井東圧化学株式会社Patent applicant: Mitsui Toatsu Chemical Co., Ltd.
Claims (1)
ルエステルを１〜１００ｐｐｍ、塩化第一銅を０．１〜
５ｐｐｍ、更に塩化亜鉛を０．１〜５ｐｐｍ添加するこ
とを特徴とする無水マレイン酸の着色防止方法The weight ratio of gallic acid n-propyl ester to maleic anhydride is 1 to 100 ppm, and cuprous chloride is 0.1 to 100 ppm.
A method for preventing discoloration of maleic anhydride, characterized by adding 5 ppm and further 0.1 to 5 ppm of zinc chloride.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1013985A JP2767851B2 (en) | 1989-01-25 | 1989-01-25 | Method for preventing discoloration of maleic anhydride |
| CA002008178A CA2008178C (en) | 1989-01-25 | 1990-01-19 | Process for producing maleic anhydride |
| US07/467,377 US5026876A (en) | 1989-01-25 | 1990-01-19 | Process for producing maleic anhydride |
| EP90300725A EP0381362B1 (en) | 1989-01-25 | 1990-01-23 | Process for producing maleic anhydride |
| AT90300725T ATE99665T1 (en) | 1989-01-25 | 1990-01-23 | PROCESS FOR THE PREPARATION OF MALEIC ACID ANHYDRIDE. |
| DE69005655T DE69005655T2 (en) | 1989-01-25 | 1990-01-23 | Process for the preparation of maleic anhydride. |
| ES90300725T ES2049413T3 (en) | 1989-01-25 | 1990-01-23 | PROCEDURE FOR THE PRODUCTION OF MALEIC ANHYDRIDE. |
| KR1019900000789A KR920001790B1 (en) | 1989-01-25 | 1990-01-24 | Process for producing maleic antihydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1013985A JP2767851B2 (en) | 1989-01-25 | 1989-01-25 | Method for preventing discoloration of maleic anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02196778A true JPH02196778A (en) | 1990-08-03 |
| JP2767851B2 JP2767851B2 (en) | 1998-06-18 |
Family
ID=11848521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1013985A Expired - Fee Related JP2767851B2 (en) | 1989-01-25 | 1989-01-25 | Method for preventing discoloration of maleic anhydride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2767851B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534489A (en) * | 1999-01-13 | 2002-10-15 | ハンツマン・ペトロケミカル・コーポレーシヨン | Stabilization of anhydride |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49110624A (en) * | 1973-03-10 | 1974-10-22 |
-
1989
- 1989-01-25 JP JP1013985A patent/JP2767851B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49110624A (en) * | 1973-03-10 | 1974-10-22 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534489A (en) * | 1999-01-13 | 2002-10-15 | ハンツマン・ペトロケミカル・コーポレーシヨン | Stabilization of anhydride |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2767851B2 (en) | 1998-06-18 |
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