JPS6358188B2 - - Google Patents
Info
- Publication number
- JPS6358188B2 JPS6358188B2 JP55009127A JP912780A JPS6358188B2 JP S6358188 B2 JPS6358188 B2 JP S6358188B2 JP 55009127 A JP55009127 A JP 55009127A JP 912780 A JP912780 A JP 912780A JP S6358188 B2 JPS6358188 B2 JP S6358188B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- formula
- present
- mixture
- general formula
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 8
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- -1 anthraquinone compound Chemical class 0.000 claims description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000002994 raw material Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000835 fiber Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000001045 blue dye Substances 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 2
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 2
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- IYHIKYZDSVTAPF-UHFFFAOYSA-N 1,2-diamino-3,4-dihydroxyanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(N)C(O)=C2O IYHIKYZDSVTAPF-UHFFFAOYSA-N 0.000 description 1
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- CEVLPYIIUNVBAT-UHFFFAOYSA-N anthracene-9,10-dione;hydron;bromide Chemical compound Br.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 CEVLPYIIUNVBAT-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明はアントラキノン系化合物の製造法に関
するものである。
下記一般式〔〕又は〔〕
The present invention relates to a method for producing anthraquinone compounds. The following general formula [] or []
【式】【formula】
【式】
（式中、ｍは０〜２の整数であり、混合物の平
均値としては0.7〜1.5である）で表わされるジア
ミノジヒドロキシアントラキノンの臭素化物はポ
リエステル繊維を染色するための青色染料として
広く利用されており、従来、アントラキノンジス
ルホン酸を出発原料として製造されてきた。しか
し、近年、アントラキノンジスルホン酸の製造に
水銀触媒を使用する必要があるため、環境問題の
面からその製造が中止され、代りにジニトロアン
トラキノンを出発原料として使用する方向にあ
る。
ジニトロアントラキノンを出発原料とした場合
には、先ず、ニトロ基を還元したのち、臭素化
し、次いで、これを加水分解することにより、前
示一般式〔〕又は〔〕のジアミノヒドロキシ
アントラキノン臭素化物を得ることができるが、
この方法は未だ工業的に確立されておらず、採用
する条件によつて得られる製品の染料としての効
果が大きく左右される。例えば、上記の加水分解
反応を濃硫酸又はオリウム中にて硼酸触媒の存在
下、加熱処理することにより行なう方法が知られ
ているが、この方法では、得られる生成物中の臭
素含有量が高くなる。すなわち、前示一般式
〔〕又は〔〕中のｍの平均値が例えば、1.7以
上と高い混合物が得られるのである。このよう
に、生成物中の臭素含有量が高くなると、これを
ポリエステル繊維用の染料として使用した場合に
は、染着性が著しく低下すると言う欠点を有す
る。
本発明者等は上記実情に鑑み、ジアミノアント
ラキノン臭素化物をオリウム中で加水分解して前
示一般式〔〕又は〔〕の化合物を製造する場
合、生成物中の臭素含有量が高くならないような
製造法を得ることを目的として種々検討した結
果、反応中にある特定の処理を施すことにより、
本発明の目的が達成されることを見い出し本発明
を完成した。
すなわち、本発明の要旨は、下記一般式〔〕
及び／又は〔〕[Formula] (where m is an integer of 0 to 2, and the average value of the mixture is 0.7 to 1.5) Brominated diamino dihydroxy anthraquinone is widely used as a blue dye for dyeing polyester fibers. Conventionally, it has been produced using anthraquinone disulfonic acid as a starting material. However, in recent years, since the production of anthraquinone disulfonic acid requires the use of a mercury catalyst, its production has been discontinued due to environmental concerns, and the trend is to use dinitroanthraquinone as a starting material instead. When dinitroanthraquinone is used as a starting material, the nitro group is first reduced, then brominated, and then hydrolyzed to obtain the diaminohydroxyanthraquinone bromide of the general formula [] or []. You can, but
This method has not yet been established industrially, and the effectiveness of the resulting product as a dye is greatly influenced by the conditions used. For example, a method is known in which the above hydrolysis reaction is carried out by heat treatment in concentrated sulfuric acid or olium in the presence of a boric acid catalyst, but this method results in a high bromine content in the resulting product. Become. That is, a mixture can be obtained in which the average value of m in the general formula [] or [] is as high as, for example, 1.7 or more. As described above, when the bromine content in the product is high, it has the disadvantage that the dyeing properties are significantly reduced when the product is used as a dye for polyester fibers. In view of the above circumstances, the present inventors have determined that when producing the compound of the general formula [] or [] by hydrolyzing diaminoanthraquinone bromide in olium, the bromine content in the product will not be high. As a result of various studies aimed at obtaining a manufacturing method, we found that by performing a certain treatment during the reaction,
The present invention was completed after discovering that the object of the present invention can be achieved. That is, the gist of the present invention is the following general formula []
and/or []
【式】【formula】
【式】
（式中、ｎは０〜２の整数である）で表わされ
る化合物を濃硫酸又はオリウム中にて硼酸又は三
酸化硼素触媒の存在下、加熱処理して加水分解す
ることにより下記一般式〔〕及び／又は〔〕[Formula] (wherein n is an integer of 0 to 2) is heated in concentrated sulfuric acid or olium in the presence of a boric acid or boron trioxide catalyst to hydrolyze the following compounds. expression [] and/or []
【式】【formula】
【式】
（式中、ｍは０〜２の整数であり、混合物の平
均値としては0.7〜1.5である）で表わされる化合
物を製造する方法において、密閉された反応器を
用い、反応器の気相部又は反応液中に不活性ガス
を流通させながら反応を行なうことを特徴とする
アントラキノン系化合物の製造法に存する。
以下、本発明を詳細に説明する。
本発明の反応原料である前示一般式〔〕及
び／又は〔〕で表わされる化合物は通常、１，
５―又は１，８―ジニトロアントラキノンを還元
して得たジアミノアントラキノンを臭素化して得
られるが、生成物は臭素含有量の異なる混合物で
あり、その混合物の平均臭素含有量は例えば、
2.1〜3.5である。また、本発明では臭素化反応で
得た混合物をそのまま原料として使用するので、
通常、副生物などのその他の成分が10重量％以下
で含有されていても差し支えない。
上記臭素化反応は通常、ジアミノアントラキノ
ンを原料に対して４〜10重量倍の98％以上の濃硫
酸又はSO3濃度10％以下のオリウム中に溶解し、
撹拌下、所定量の分子状臭素を添加することによ
り行なわれる。反応温度は通常、50〜100℃、好
ましくは60〜70℃で、反応時間は30〜60時間、好
ましくは35〜45時間である。この反応では必要に
応じて、例えば、反応原料に対して0.5〜２重量
％の沃化カリウム又は分子状沃素などの触媒を使
用すると反応速度が速くなるので好ましい。
臭素化反応を終了した後の混合物は通常、混合
物に対して１〜10重量倍の水と混合し生成した臭
素化物を析出させ、常法により分離、洗浄し回収
されるが、本発明では反応後の混合物をそのまま
次の加水分解反応に使用してもよい。
上記のようにして得た前示一般式〔〕及び／
又は〔〕で表わされる化合物を濃硫酸又はオリ
ウム中にて硼酸又は三酸化硼素触媒の存在下、加
熱処理して加水分解し、前示一般式〔〕及び／
又は〔〕で表わされる化合物を製造する。濃硫
酸又はオリウムの使用量は例えば、原料に対して
４〜10重量倍であり、通常、SO3濃度15重量％以
下、好ましくは２〜８重量％のオリウムを使用す
るのが望ましい。また、触媒の使用量は通常、原
料に対して30〜100重量％、好ましくは40〜70重
量％である。
反応温度は通常、120〜160℃、好ましくは140
〜150℃であり、あまり低いと反応が良好に進行
せず、逆に、あまり高くても副生物の生成が多く
なるので好ましくない。反応時間は通常、５〜15
時間程度である。本発明の反応は通常、溶媒中に
原料及び触媒を完溶させたのち、撹拌下、所定の
条件で実施される。
本発明では密閉された反応器を用い、反応器の
気相部又は反応液中に不活性ガスを流通させるこ
とを必須の要件とするものである。通常、不活性
ガスを反応液中に直接、吹き込む方法を採用した
方が、Brの除去効率が高いので好ましい。不活
性ガスの流通量は装置の形式、反応温度及び吹き
込み方法などにより異なるが、例えば、反応液１
Kg当り0.1／分以上、好ましくは0.5〜５／分
である。不活性ガスの種類は通常、窒素ガス、炭
酸ガス、脱湿空気などが挙げられる。
この不活性ガスの流通処理により、得られる生
成物中の臭素含有量を低く抑えることができるの
である。この加水分解反応は原料化合物のα位の
臭素原子がはずれ、代りに、ヒドロキシル基が導
入される反応であるが、遊離した臭素原子が再び
β位に導入される可能性があり、不活性ガスの流
通処理をしない場合には、臭素含有量の低い生成
物は得られない。本発明では生成物中のβ位の臭
素原子数は０〜２個であり、全生成物の平均臭素
含有量は0.7〜1.5個である。臭素含有量が本発明
の範囲以上に多くなると、ポリエステル繊維用の
染料として用いた場合の染着率が著しく低下する
ので好ましくない。
加水分解後の混合物は通常、混合物に対して１
〜10重量倍の水と混合し、前示一般式〔〕及
び／又は〔〕の化合物を析出させ、次いで、常
法に従つて、ケーキを分離、洗浄することにより
目的とする青色染料を回収することができる。
本発明によれば、不活性ガス処理をしながら加
水分解反応を行なうことにより、生成物中の臭素
含有量を低く抑えることができる。したがつて、
本発明で得た青色染料はポリエステル繊維に対す
る染着率が極めて高く好ましいものである。
次に、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。
実施例 １
構造式[Formula] (In the formula, m is an integer of 0 to 2, and the average value of the mixture is 0.7 to 1.5). The present invention relates to a method for producing an anthraquinone compound, characterized in that the reaction is carried out while passing an inert gas through a gas phase or a reaction solution. The present invention will be explained in detail below. The compound represented by the general formula [] and/or [], which is a reaction raw material of the present invention, is usually 1,
It is obtained by brominating diaminoanthraquinone obtained by reducing 5- or 1,8-dinitroanthraquinone, but the product is a mixture with different bromine contents, and the average bromine content of the mixture is, for example,
It is between 2.1 and 3.5. In addition, in the present invention, the mixture obtained in the bromination reaction is used as a raw material, so
Generally, it is acceptable even if other components such as by-products are contained in an amount of 10% by weight or less. The above bromination reaction usually involves dissolving diaminoanthraquinone in concentrated sulfuric acid of 98% or more or olium with an SO 3 concentration of 10% or less, which is 4 to 10 times the weight of the raw material.
This is done by adding a predetermined amount of molecular bromine under stirring. The reaction temperature is usually 50-100°C, preferably 60-70°C, and the reaction time is 30-60 hours, preferably 35-45 hours. In this reaction, it is preferable to use a catalyst such as potassium iodide or molecular iodine in an amount of 0.5 to 2% by weight based on the reaction raw materials, as the reaction rate becomes faster. The mixture after the bromination reaction is usually mixed with water in an amount of 1 to 10 times the weight of the mixture to precipitate the produced brominated product, which is then separated and washed by conventional methods to be recovered. The latter mixture may be used as it is in the next hydrolysis reaction. The general formula [] and/or obtained as above
Or, the compound represented by [] is hydrolyzed by heat treatment in concentrated sulfuric acid or olium in the presence of a boric acid or boron trioxide catalyst, and the compound represented by the general formula [] and/or
Or produce a compound represented by [ ]. The amount of concentrated sulfuric acid or olium used is, for example, 4 to 10 times the weight of the raw material, and it is usually desirable to use olium with an SO 3 concentration of 15% by weight or less, preferably 2 to 8% by weight. Further, the amount of catalyst used is usually 30 to 100% by weight, preferably 40 to 70% by weight based on the raw material. The reaction temperature is usually 120-160℃, preferably 140℃
-150°C. If the temperature is too low, the reaction will not proceed well, and if it is too high, by-products will be produced in large quantities, which is not preferable. Reaction time is usually 5-15
It takes about an hour. The reaction of the present invention is usually carried out under predetermined conditions with stirring after completely dissolving the raw materials and catalyst in a solvent. In the present invention, a sealed reactor is used, and it is essential to circulate an inert gas into the gas phase of the reactor or into the reaction liquid. Generally, it is preferable to adopt a method in which an inert gas is directly blown into the reaction liquid because the removal efficiency of Br is higher. The flow rate of inert gas varies depending on the type of apparatus, reaction temperature, blowing method, etc., but for example,
The rate is 0.1/min or more, preferably 0.5 to 5/min per kg. Types of inert gas typically include nitrogen gas, carbon dioxide gas, and dehumidified air. This inert gas flow treatment makes it possible to keep the bromine content in the resulting product low. This hydrolysis reaction is a reaction in which the bromine atom at the α position of the raw material compound is removed and a hydroxyl group is introduced in its place, but there is a possibility that the free bromine atom is reintroduced to the β position, If the flow treatment is not carried out, a product with a low bromine content cannot be obtained. In the present invention, the number of bromine atoms at the β position in the product is 0 to 2, and the average bromine content of all products is 0.7 to 1.5. If the bromine content exceeds the range of the present invention, the dyeing rate will drop significantly when used as a dye for polyester fibers, which is not preferable. The mixture after hydrolysis is usually 1
Mix with ~10 times the weight of water to precipitate the compound of the general formula [] and/or [], then separate and wash the cake according to a conventional method to recover the desired blue dye. can do. According to the present invention, the bromine content in the product can be kept low by performing the hydrolysis reaction while treating with an inert gas. Therefore,
The blue dye obtained in the present invention has an extremely high dyeing rate on polyester fibers and is therefore preferable. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 Structural formula
【式】
上記構造式のアントラキノン臭素化物（ｎは０
〜２で、混合物の平均値としては0.5である）10
ｇ、硼酸5.0ｇ及びSO3濃度5wt％のオリウム80ｇ
をコンデンサー、撹拌機および加熱装置を備えた
反応器に仕込み、50〜60℃で１時間撹拌して均一
溶液とした後、140℃に昇温して撹拌下、反応混
合物に300ml／分の割合で窒素ガスを吹込みなが
ら10時間反応を行つた。反応終了後、反応混合物
を別の撹拌容器に張られた水120ｇ中に排出し、
次いで、これを過、水洗、乾燥して染料ケーキ
7.9ｇを得た。この染料ケーキを分析した結果、
平均臭素含有率は1.2個／分子であつた。
比較のため同一原料を用いて、窒素ガスを通気
することなく他は実施例１と同一条件で行つたと
ころ染料ケーキの平均臭素含有率は1.9個／分子
であつた。
このようにして得た各染料ケーキを用いてポリ
エステル布を染色し染着率のテストを行つたとこ
ろ、第１表に示す結果を得た。
実施例 ２
実施例１において反応原料として下記構造式
[Formula] Anthraquinone bromide of the above structural formula (n is 0
~2 and the average value of the mixture is 0.5) 10
g, boric acid 5.0 g and SO 3 concentration 5 wt% olium 80 g
was charged into a reactor equipped with a condenser, a stirrer, and a heating device, stirred at 50-60℃ for 1 hour to make a homogeneous solution, and then heated to 140℃ and added to the reaction mixture at a rate of 300ml/min under stirring. The reaction was carried out for 10 hours while blowing nitrogen gas. After the reaction was completed, the reaction mixture was discharged into 120 g of water placed in another stirring container.
Next, this is filtered, washed with water, and dried to form a dye cake.
7.9g was obtained. As a result of analyzing this dye cake,
The average bromine content was 1.2 bromine/molecule. For comparison, a test was carried out under the same conditions as in Example 1, using the same raw materials and without passing nitrogen gas, and the average bromine content of the dye cake was 1.9 bromine/molecule. When polyester cloth was dyed using each of the dye cakes obtained in this manner and the dyeing rate was tested, the results shown in Table 1 were obtained. Example 2 In Example 1, the following structural formula was used as a reaction raw material.
【式】
（ｎは０〜２で、混合物の平均値としては0.3
である）の化合物を用いて、実施例１の方法と同
様の反応及びテストを行ない第２表に示す結果を
得た。
比較のため窒素通気を行うことなく、同一原料
を使用して実施例２と同じ条件で反応及びテスト
した結果を第２表に示す。[Formula] (n is 0 to 2, and the average value of the mixture is 0.3
The same reactions and tests as in Example 1 were carried out using the compound (which is ), and the results shown in Table 2 were obtained. For comparison, a reaction and test was conducted under the same conditions as in Example 2 using the same raw materials without nitrogen aeration, and the results are shown in Table 2.
【表】【table】
Claims (1)
る化合物を濃硫酸又はオリウム中にて硼酸又は三
酸化硼素触媒の存在下、加熱処理して加水分解す
ることにより下記一般式〔〕及び／又は〔〕 【式】 【式】 （式中、ｍは０〜２の整数であり、混合物の平
均値としては0.7〜1.5である）で表わされる化合
物を製造する方法において、密閉された反応器を
用い、反応器の気相部又は反応液中に不活性ガス
を流通させながら反応を行なうことを特徴とする
アントラキノン系化合物の製造法。[Scope of Claims] 1. A compound represented by the following general formula [] and/or [] [Formula] [Formula] (wherein n is an integer of 0 to 2) is dissolved in boric acid in concentrated sulfuric acid or olium. Or, in the presence of a boron trioxide catalyst, by heat treatment and hydrolysis, the following general formula [] and/or [] [Formula] [Formula] (where m is an integer from 0 to 2, (average value is 0.7 to 1.5), the reaction is carried out using a closed reactor while circulating an inert gas in the gas phase of the reactor or in the reaction liquid. A method for producing an anthraquinone compound characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP912780A JPS56108745A (en) | 1980-01-29 | 1980-01-29 | Preparation of anthraquinone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP912780A JPS56108745A (en) | 1980-01-29 | 1980-01-29 | Preparation of anthraquinone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56108745A JPS56108745A (en) | 1981-08-28 |
| JPS6358188B2 true JPS6358188B2 (en) | 1988-11-15 |
Family
ID=11711960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP912780A Granted JPS56108745A (en) | 1980-01-29 | 1980-01-29 | Preparation of anthraquinone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56108745A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53133231A (en) * | 1977-04-26 | 1978-11-20 | Sumitomo Chem Co Ltd | Preparation of anthraquinone intermediate |
-
1980
- 1980-01-29 JP JP912780A patent/JPS56108745A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53133231A (en) * | 1977-04-26 | 1978-11-20 | Sumitomo Chem Co Ltd | Preparation of anthraquinone intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56108745A (en) | 1981-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2943088A (en) | Production of cyanuric acid from urea | |
| US2549842A (en) | Method for producing polyhalophthalocyanine pigments | |
| US2522939A (en) | Process for the production of phenolphthalein | |
| US2109952A (en) | Method of preparing aminosulphonic acid | |
| JPS6358188B2 (en) | ||
| US2058911A (en) | Process for the purification of naphthylamine sulphonic acid | |
| CN108623442A (en) | A kind of tetrachloroquinone reduces bioxin method in preparing | |
| US2947781A (en) | Reduction process for preparing aromatic p-amino compounds | |
| US3185709A (en) | Process for obtaining crystal violet lactone | |
| US3267116A (en) | Process for preparing pigmentary copper phthalocyanine | |
| US2681347A (en) | Preparation of leuco metal phthalocyanines | |
| JPS6245903B2 (en) | ||
| US4067881A (en) | Manufacture of polychloro-copper phthalocyanines | |
| US2333672A (en) | Process of producing alkaline sulphates from ferrous sulphate | |
| US4259248A (en) | Process for the preparation of mixtures of dinitroanthraquinones with a high content of 1,5- and 1,8- dinitroanthraquinone | |
| US4235789A (en) | Process for the preparation of 1-amino-2-bromo-4-hydroxyanthraquinone | |
| US2013790A (en) | Bromination of pyranthrone | |
| US4645626A (en) | Process for the production of quinizarine derivatives which are disubstituted in the 5- and 8-positions by hydroxyl or chlorine | |
| US2764586A (en) | Manufacture of n, n'-dihydroanthraquinone-azine | |
| US3222377A (en) | Halogenation of phthalocyanines | |
| US3153099A (en) | Production of 1, 4-dinitro-2, 3, 5, 6-tetraalkylbenzenes | |
| JPS61204272A (en) | Production of vat dye | |
| CN115057767A (en) | Preparation method of phthalic acid | |
| JPS61118378A (en) | Production of tetrachlorophthalic anhydride | |
| JPS5833218B2 (en) | Alpha - Anthraquinone |