JPH0464358B2 - - Google Patents
Info
- Publication number
- JPH0464358B2 JPH0464358B2 JP19019183A JP19019183A JPH0464358B2 JP H0464358 B2 JPH0464358 B2 JP H0464358B2 JP 19019183 A JP19019183 A JP 19019183A JP 19019183 A JP19019183 A JP 19019183A JP H0464358 B2 JPH0464358 B2 JP H0464358B2
- Authority
- JP
- Japan
- Prior art keywords
- tar
- boiling point
- oil
- fraction
- cut
- 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
- 238000009835 boiling Methods 0.000 claims description 28
- 239000011269 tar Substances 0.000 claims description 26
- 239000011280 coal tar Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000010521 absorption reaction Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 230000002745 absorbent Effects 0.000 description 7
- 239000002250 absorbent Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000004517 catalytic hydrocracking Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013064 chemical raw material Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011287 low-temperature tar Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011277 road tar Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
Description
この発明は、コークス炉から副生するコールタ
ールを蒸留して軽質油分を除去したカツトタール
の処理方法に関する。
コークス炉から副生するコールタールは、第１
図に示すごとく、沸点の低い順にタール軽油、カ
ルボル油、ナフタリン油、吸収油、カツトター
ル、アントラセン油、ピツチに蒸留分離される。
操作では通常、常圧蒸留により吸収油までの沸点
270℃以下の留分（軽質油分）が除去され、残部
カツトタールを減圧蒸留してアントラセン油が除
去されるが、減圧蒸留操作は蒸留残渣（ロードタ
ール、ピツチ等）の需要量に応じて適宜行なわれ
ている。カツトタールとは、コールタールを蒸留
してある特定の留分、すなわち軽質油分を除去し
たタールを指し、タール蒸留製品の大部分を占め
ている。
ところで、コールタールを蒸留して得られる沸
点範囲230〜370℃留分が吸収油と呼ばれるのは、
コークス炉ガス中に含まれる粗ベンゼンの回収に
用いられるからであり、吸収油に必要な以下に示
す性質を有しているからである。
粗ベンゼンの吸収能が高い。
粗ベンゼンとの分離が容易である。
低粘度である。
結晶を生成しない。
この沸点範囲230〜270℃留分は、メチルナフタ
リン（沸点241℃、245℃）、ジフエニル（沸点255
℃）、ジメチルナフタリン（沸点260〜270℃）、イ
ンドール（沸点253℃）、キノリン（沸点238℃）
等を主成分とし、ナフタリン（沸点218℃）、アス
ナフテン（沸点281℃）、アントラセン（沸点342
℃）等が混入している。これらの化合物は下表に
示すごとく、幅広い用途を有し、かつ今後需要増
が見込まれる化合物である。
The present invention relates to a method for treating cut tar obtained by distilling coal tar by-produced from a coke oven to remove light oil components. Coal tar produced as a by-product from coke ovens is
As shown in the figure, it is distilled and separated into tar gas oil, carbol oil, naphthalene oil, absorption oil, cut tar, anthracene oil, and pitch in order of decreasing boiling point.
In operation, the boiling point of the absorbed oil is usually reduced by atmospheric distillation.
The fraction below 270°C (light oil) is removed, and the remaining cut tar is distilled under reduced pressure to remove anthracene oil. The reduced pressure distillation operation may be carried out as appropriate depending on the demand for the distillation residue (road tar, pitch, etc.). It is. Cut tar refers to tar obtained by distilling coal tar to remove a specific fraction, that is, light oil, and accounts for the majority of tar distillation products. By the way, the boiling point range 230-370℃ fraction obtained by distilling coal tar is called absorption oil.
This is because it is used to recover crude benzene contained in coke oven gas, and it has the following properties necessary for absorption oil. High ability to absorb crude benzene. Easy to separate from crude benzene. Low viscosity. Does not produce crystals. This boiling point range 230-270°C fraction contains methylnaphthalene (boiling point 241°C, 245°C), diphenyl (boiling point 255°C),
℃), dimethylnaphthalene (boiling point 260-270℃), indole (boiling point 253℃), quinoline (boiling point 238℃)
The main components are naphthalene (boiling point 218℃), asnaphthene (boiling point 281℃), and anthracene (boiling point 342℃).
℃) etc. are mixed in. As shown in the table below, these compounds have a wide range of uses, and demand is expected to increase in the future.
【表】
しかしながら、コールタールの大部分は前記し
た通りカツトタールであり、吸収油留分は僅か数
％（コールタール当り）にすぎない。従つて、こ
のままでは今後見込まれる上記化合物回収のため
の吸収油留分の需要増に対応することができな
い。その対策として、沸点230〜270℃留分を化学
原料として利用するために、例えばコールタール
の蒸留設備を増強する方法が考えられるが、蒸留
設備を増強するだけでは、現状では使用量が限ら
れているカツトタールを過剰生産することにな
り、吸収油留分の生産コスト中にカツトタールの
処理費用が含まれることとなつて、結局コスト高
につながり好ましくない。また、吸収油に使用さ
える量を減少した場合には、循環使用中に次第に
重合化し、粘度が増して吸収能が低下する。
この発明は上記実情に鑑みてなされたものであ
り、カツトタールから吸収油代替品を製造するこ
とにより沸点230〜270℃留分を化学原料として利
用する割合を増加するとともに、カツトタールの
有効利用をはかることを目的とするものである。
この発明に係るカツトタールの処理方法は、コ
ールタルーを蒸留して沸点270℃以下の留分を除
去して得たカツトタールを水素化分解し、該反応
生成物を蒸留して得られた沸点範囲200〜350℃留
分を吸収油代替品として用いることを特徴とする
ものである。
すなわち、この発明はカツトタールを水素化分
解して生成した軽質油のうち、沸点範囲200〜350
℃留分を吸収油代替品として用いる方法である。
この発明において吸収油代替品として用いる沸
点範囲200〜350℃留分とは、沸点範囲200〜300℃
留分および沸点範囲300〜350℃留分の単独または
混合物、あるいは沸点範囲200〜300℃の間の任意
の沸点範囲の留分をいう。
以下、この発明に係るコールタールの処理方法
について詳細に説明する。
この発明におけるコールタールは、石炭乾留時
に副生する高温タールや低温タール等を蒸留して
沸点270℃以下の留分を除去したものを用いるが、
これはカツトタールの利用効率、水素化分解効率
および触媒効率を考慮したことによる。すなわ
ち、沸点270℃以下留分を予め除去しておいた方
がカツトタールの利用効率、水添分解効率および
触媒効率が良く、後の吸収油代替成品の分離に好
都合だらかである。
この発明では上記のコールタールを第２図に示
すごとく触媒の存在下で水素化分解する。この時
の反応温度としては400〜500℃、水素圧は100〜
200Kg／cm2Ｇ、あるいはそれ以上に保つ。反応温
度が400℃未満では第３図に示すごとく目的とす
る吸収油代替成品の収率が低く、500℃以上の温
度では軽質化反応やその逆の重合反応が速やかに
進行するために吸収油代替成品の収率が低下す
る。また、水素圧が100Kg／cm2Ｇ未満では芳香環
の水添反応が進行しにくいために水添反応に引き
続いて行なわれる分解反応が起こりにくく、目的
とする留分の収率が低下し、他方水素圧が必要以
上に高くなると高価な水素の消費量が増加し不経
済であるとともに、耐圧設備に要するコストが割
高となる。
なお、水素化分解に用いる触媒としては、特に
限定するものではないが、入手が容易でかつ安価
な鉄系触媒を用いることができる。鉄系触媒とし
ては、赤泥、鉄鉱石等が挙げられ、その使用量は
カツトタールに対して１〜10％程度でよい。ま
た、助触媒として硫黄化合物を鉄系触媒と同様カ
ツトタールに対して１〜10％程度使用することが
望ましい。触媒の使用量を１〜10％程度としたの
は、触媒濃度が１％未満では効果がなく、10％以
上では触媒効率が悪くなるからである。
上記の水素化分解反応生成物は、次の蒸留工程
で沸点範囲200〜300℃留分と300〜350℃留分を分
離回収する。この200〜300℃留分と300〜350℃留
分について、この発明者らがガスクロマトグラフ
イー分析、元素分析、核磁気共鳴分析等による性
状調査を行なつたところ、従来のコールタール留
分に比べ水素化生成物が多量に存在することが認
められ、結晶生の低下や低粘度化が促進されてい
ることが判明した。従つて、水素化生成物中の沸
点200〜300℃留分および300〜350℃留分は、吸収
油代替成品として十分使用可能である。
次に、この発明の実施例について説明する。
実施例
コークス炉から副生したコールタールを蒸留し
て沸点270℃以下留分を除去した第１表に示す元
素分析値を有するカツトタールを、0.5Kg／Hrの
処理能力を有する水素化分解装置により第２表に
示す操業条件で水素化分解し、該反応生成物を蒸
留して得られた吸収油代替成品の物質収支を第３
表に示す。さらに、この吸収油代替成品の性質
を、実際に使用されている通常の吸収油と比較し
て第４表に示す。
第４表の結果より明らかなごとく、粗ベンゼン
の吸収能を表わす含ベン油中の粗ベンゼン濃度は
吸収油と比べて若干多く、粗ベンゼンの脱離能を
表わす脱ベンゼン油中の粗ベンゼン濃度は著しく
少ない。さらに、運転上の容易さを表わす粘度は
小さく、ナフタリン等による結晶析出温度は低
い。また、石油系重質油を代替とした場合はスラ
ツジが生成し操業困難となるが、石炭系重質油の
場合はスラツジの生成が認められない。
これらの結果より、カツトタールを水素化分解
して得られた沸点200〜300℃留分、および300〜
350℃留分は吸収油と比べてすぐれた粗ベンゼン
吸収剤であることがわかる。[Table] However, as mentioned above, the majority of coal tar is cut tar, and the absorbed oil fraction is only a few percent (per coal tar). Therefore, if things continue as they are, it will not be possible to meet the expected future increase in demand for absorbed oil fractions for recovery of the above-mentioned compounds. As a countermeasure, for example, it is possible to increase the coal tar distillation equipment in order to use the boiling point 230-270°C fraction as a chemical raw material, but simply increasing the distillation equipment would limit the amount used at present. This results in excessive production of cut tar, and the cost of processing the cut tar is included in the production cost of the absorbed oil fraction, resulting in an undesirable increase in costs. Furthermore, if the amount used in the absorbent oil is reduced, it will gradually polymerize during cyclic use, increasing the viscosity and reducing the absorption capacity. This invention was made in view of the above-mentioned circumstances, and aims to increase the proportion of boiling point 230-270°C fractions used as chemical raw materials and to effectively utilize cut tar by producing an absorbent oil substitute from cut tar. The purpose is to The method for treating cut tar according to the present invention includes hydrocracking the cut tar obtained by distilling coal tar and removing the fraction with a boiling point of 270°C or lower, and distilling the reaction product. It is characterized by using the 350°C fraction as a substitute for absorbed oil. In other words, this invention uses light oil produced by hydrocracking cut tar with a boiling point range of 200 to 350.
This method uses the °C fraction as a substitute for absorbed oil. In this invention, the boiling point range 200-350°C fraction used as an absorption oil substitute means a boiling point range 200-300°C fraction.
It refers to fractions and fractions with a boiling point range of 300 to 350°C, singly or as a mixture, or any fraction with a boiling point range between 200 to 300°C. Hereinafter, the method for treating coal tar according to the present invention will be explained in detail. The coal tar used in this invention is obtained by distilling high-temperature tar, low-temperature tar, etc. that are by-produced during coal carbonization, and removing fractions with a boiling point of 270°C or lower.
This is due to consideration of cutting tar utilization efficiency, hydrocracking efficiency, and catalyst efficiency. That is, it is better to remove the fraction with a boiling point of 270° C. or lower in advance, which improves cut tar usage efficiency, hydrogen cracking efficiency, and catalyst efficiency, and is convenient for subsequent separation of absorbed oil substitute products. In this invention, the above-mentioned coal tar is hydrogenolyzed in the presence of a catalyst as shown in FIG. The reaction temperature at this time is 400~500℃, and the hydrogen pressure is 100~
Maintain at 200Kg/cm 2 G or higher. If the reaction temperature is less than 400℃, the yield of the target absorbent oil replacement product will be low, as shown in Figure 3, and if the reaction temperature is higher than 500℃, the lightening reaction or the reverse polymerization reaction will proceed rapidly, so the absorption oil will be reduced. Yields of substitute products are reduced. In addition, when the hydrogen pressure is less than 100 Kg/cm 2 G, the hydrogenation reaction of aromatic rings is difficult to proceed, so the decomposition reaction that follows the hydrogenation reaction is difficult to occur, and the yield of the target fraction is reduced. On the other hand, if the hydrogen pressure becomes higher than necessary, the amount of expensive hydrogen consumed increases, which is uneconomical, and the cost required for pressure-resistant equipment becomes relatively high. Note that the catalyst used for hydrogenolysis is not particularly limited, but an easily available and inexpensive iron-based catalyst can be used. Examples of iron-based catalysts include red mud and iron ore, and the amount used may be about 1 to 10% based on cut tar. Further, it is desirable to use a sulfur compound as a co-catalyst in an amount of about 1 to 10% based on cut tar, similar to the iron-based catalyst. The reason why the amount of catalyst used is about 1 to 10% is that if the catalyst concentration is less than 1%, there is no effect, and if it is more than 10%, the catalyst efficiency becomes poor. The above hydrocracking reaction product is separated and recovered into a 200-300°C boiling point fraction and a 300-350°C fraction in the next distillation step. The inventors investigated the properties of these 200-300°C and 300-350°C fractions by gas chromatography analysis, elemental analysis, nuclear magnetic resonance analysis, etc., and found that the conventional coal tar fraction It was found that a large amount of hydrogenation products were present, and that crystallization and viscosity reduction were promoted. Therefore, the 200-300°C boiling point fraction and the 300-350°C fraction in the hydrogenated product can be fully used as an absorption oil replacement product. Next, embodiments of the invention will be described. Example Coal tar produced as a by-product from a coke oven was distilled to remove the fraction with a boiling point below 270°C. Cut tar having the elemental analysis values shown in Table 1 was processed using a hydrocracker with a processing capacity of 0.5 Kg/Hr. The material balance of the absorbed oil substitute product obtained by hydrocracking under the operating conditions shown in Table 2 and distilling the reaction product is shown in Table 3.
Shown in the table. Furthermore, the properties of this absorbent oil replacement product are shown in Table 4 in comparison with ordinary absorbent oils that are actually used. As is clear from the results in Table 4, the concentration of crude benzene in the benzene-containing oil, which represents the ability to absorb crude benzene, is slightly higher than that in the absorbed oil, and the concentration of crude benzene in the debenzened oil, which represents the ability to eliminate crude benzene. are significantly less. Furthermore, the viscosity, which indicates ease of operation, is low, and the crystal precipitation temperature due to naphthalene and the like is low. Furthermore, if petroleum-based heavy oil is used as a substitute, sludge will be generated, making operation difficult, but in the case of coal-based heavy oil, no sludge will be formed. From these results, the boiling point 200~300℃ fraction obtained by hydrogenolyzing cut tar, and the 300~300~
It can be seen that the 350°C fraction is a superior crude benzene absorbent compared to absorption oil.
【表】【table】
【表】【table】
【表】【table】
【表】
上記の実施例からも明らかなごとく、この発明
によれば、すぐれた吸収生を示す吸収剤が得ら
れ、吸収油を化学原料として利用可能となり、
カツトタールの有効利用がはかられるようにな
り、吸収油留分の増産が可能となるという効果を
奏し、工業的に極めて有益な発明である。[Table] As is clear from the above examples, according to the present invention, an absorbent exhibiting excellent absorption properties can be obtained, and the absorbed oil can be used as a chemical raw material.
This invention has the effect of making it possible to effectively utilize cut tar and increasing the production of absorbed oil fractions, making it an extremely useful invention industrially.
第１図は従来のコールタール処理方法を示すブ
ロツク図、第２図はこの発明に係るコールタール
処理方法を示すブロツク図、第３図は同上におけ
るカツトタールの水素化分解反応温度と吸収油代
替成品の収率の関係を示す図表である。
Fig. 1 is a block diagram showing a conventional coal tar treatment method, Fig. 2 is a block diagram showing a coal tar processing method according to the present invention, and Fig. 3 is a diagram showing cut tar hydrolysis reaction temperature and absorption oil substitute product in the above. 2 is a chart showing the relationship between the yields of
Claims (1)
分を除去して得たカツトタールを水素化分解し、
該反応生成物を蒸留して得られた沸点範囲200〜
350℃留分を吸収油代替品として用いることを特
徴とするカツトタールの処理方法。1. Hydrogenolyze cut tar obtained by distilling coal tar and removing fractions with a boiling point of 270°C or lower,
The boiling point range obtained by distilling the reaction product is 200~
A method for treating cut tar characterized by using a 350°C fraction as an absorbed oil substitute.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19019183A JPS6081290A (en) | 1983-10-12 | 1983-10-12 | Treatment of cut tar |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19019183A JPS6081290A (en) | 1983-10-12 | 1983-10-12 | Treatment of cut tar |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6081290A JPS6081290A (en) | 1985-05-09 |
| JPH0464358B2 true JPH0464358B2 (en) | 1992-10-14 |
Family
ID=16253961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19019183A Granted JPS6081290A (en) | 1983-10-12 | 1983-10-12 | Treatment of cut tar |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6081290A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0699692B2 (en) * | 1984-05-18 | 1994-12-07 | 住友金属工業株式会社 | Cuttall processing method |
| JP2013216805A (en) * | 2012-04-10 | 2013-10-24 | Showa Denko Kk | Rubber compounding oil and method for producing the same |
-
1983
- 1983-10-12 JP JP19019183A patent/JPS6081290A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6081290A (en) | 1985-05-09 |
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