JPH04182444A - Method for purifying 3,5-xylenol - Google Patents
Method for purifying 3,5-xylenolInfo
- Publication number
- JPH04182444A JPH04182444A JP31140190A JP31140190A JPH04182444A JP H04182444 A JPH04182444 A JP H04182444A JP 31140190 A JP31140190 A JP 31140190A JP 31140190 A JP31140190 A JP 31140190A JP H04182444 A JPH04182444 A JP H04182444A
- Authority
- JP
- Japan
- Prior art keywords
- xylenol
- fraction
- heptane
- purity
- crystals
- 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
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 239000013078 crystal Substances 0.000 abstract description 20
- 238000011084 recovery Methods 0.000 abstract description 17
- 238000004821 distillation Methods 0.000 abstract description 6
- 238000005406 washing Methods 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 4
- 239000011369 resultant mixture Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002994 raw material Substances 0.000 description 19
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 12
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 8
- 239000011269 tar Substances 0.000 description 7
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 6
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 6
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 150000003739 xylenols Chemical class 0.000 description 4
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011289 tar acid Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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〕
この発明はタール留分から３，５−キシレノールを高純
度、かつ高収率で取得する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] This invention relates to a method for obtaining 3,5-xylenol from a tar fraction with high purity and high yield.
コールタール留分にはフェノール、クレゾール等の各種
有用物質が含まれており、これらが分離されて有効利用
されている。３，５−キシレノールもタール留分に含ま
れており、この化合物は９８％以上の高純度品にして農
薬の原料等に利用されている。タール留分から３，５−
キシレノールを分離精製する場合に、最終段階で問題と
なる不純物は３，４−キシレノール、メタエチルフェノ
ール、パラエチルフェノール等である。従来、これらの
分離は蒸留とか溶剤を使用しない冷却晶析によって行な
われていた。The coal tar fraction contains various useful substances such as phenol and cresol, which are separated and used effectively. 3,5-xylenol is also included in the tar fraction, and this compound is made into a highly purified product of 98% or more and is used as a raw material for agricultural chemicals. 3,5- from tar fraction
When separating and purifying xylenol, impurities that pose problems in the final stage include 3,4-xylenol, metaethylphenol, paraethylphenol, and the like. Traditionally, these separations have been carried out by distillation or cooling crystallization without using a solvent.
キシレノール類の分離方法についてはいくつか特許出願
がある。例えば、特公昭６２−１９３３号公報には、ｍ
−クレゾールのメタノールによるオルソメチル化反応に
て２．３．６− トリメチルフェノールを合成する際の
副産物である２、５−キシレノールを中間留分から冷却
晶析して、高純度で取得する方法が開示されている。析
出した結晶は遠心分離し、遠心分離機内の結晶をシクロ
ヘキサン等で洗浄している。特開昭６３−２２２１３７
号公報には、タール留分から抽出されたタール酸を蒸留
してジメチルフェノール留分を得、これを更に精留して
得た３、４−ジメチルフェノール留分あるいは３，５−
ジメチルフェノール留分を溶融晶析して、３．４−ジメ
チルフェノール又は３．５−ジメチルフェノールを高純
度で取得する方法が開示されている。この方法において
も、濾別した結晶をｎ−ヘキサン等で洗浄している。特
開昭６３−３０３９３８号公報には、コールタール系タ
ール酸から蒸留により得た２、４−ジメチルフェノール
と、２，５−ジメチルフェノールを含む留分にパラフィ
ン系またはナフテン系の炭化水素溶媒を添加し、２．５
−ジメチルフェノールを結晶として分離し、ついで該結
晶にパラフィン系またはナフテン系炭化水素溶媒を添加
して再結晶することを特徴とする２、５−ジメチルフェ
ノールの回収方法が開示されている。パラフィン系炭化
水素溶媒は、例えばｎ−ヘキサンである。There are several patent applications regarding methods for separating xylenols. For example, in Japanese Patent Publication No. 62-1933, m
Disclosed is a method for obtaining high purity 2,5-xylenol, which is a byproduct when synthesizing 2.3.6-trimethylphenol through the orthomethylation reaction of -cresol with methanol, by cooling and crystallizing it from the middle distillate. ing. The precipitated crystals are centrifuged, and the crystals inside the centrifuge are washed with cyclohexane or the like. Japanese Patent Publication No. 63-222137
In the publication, tar acid extracted from the tar fraction is distilled to obtain a dimethylphenol fraction, and this is further rectified to obtain a 3,4-dimethylphenol fraction or a 3,5-dimethylphenol fraction.
A method for obtaining highly purified 3,4-dimethylphenol or 3,5-dimethylphenol by melt-crystallizing a dimethylphenol fraction is disclosed. In this method as well, the filtered crystals are washed with n-hexane or the like. JP-A-63-303938 discloses that a paraffinic or naphthenic hydrocarbon solvent is added to a fraction containing 2,4-dimethylphenol and 2,5-dimethylphenol obtained by distillation from coal tar tar acid. Add, 2.5
- A method for recovering 2,5-dimethylphenol is disclosed, which is characterized in that dimethylphenol is separated as crystals, and then a paraffinic or naphthenic hydrocarbon solvent is added to the crystals for recrystallization. The paraffinic hydrocarbon solvent is, for example, n-hexane.
従来の冷却晶析法は、純度向上効果が充分でなく、多段
晶析で高純度品を得る場合には手間と収率の低下が問題
であった。また、窒素不純物及び硫黄不純物が精製結晶
中に残存し、経時着色及び臭いの原因となって製品品質
に悪影響を及ぼしていた。The conventional cooling crystallization method does not have a sufficient effect of improving purity, and when obtaining a high purity product by multi-stage crystallization, there are problems of labor and a decrease in yield. In addition, nitrogen impurities and sulfur impurities remained in the purified crystals, causing coloration and odor over time and adversely affecting product quality.
この発明はこれらの問題を解決して高回収率で、高純度
の３，５−キシレノールを得ることを目的としている。The object of the present invention is to solve these problems and obtain highly purified 3,5-xylenol with a high recovery rate.
（課題を解決するための手段〕
本発明は、上記課題を解決するべくなされたものであり
、タール留分から分離された３、５−キシレノール画分
にｎ−ヘプタンを加え、０〜−２０℃に冷却した後固液
分離することによってかかる目的を達成したものである
。(Means for Solving the Problems) The present invention has been made to solve the above problems.N-heptane is added to the 3,5-xylenol fraction separated from the tar fraction, and the This objective was achieved by performing solid-liquid separation after cooling.
３．５−キシレノール画分は、タール留分から蒸留等の
手段によって得られたものであり、３，５−キシレノー
ルの純度が６０〜９２重量％程度、好ましくは７３〜８
８重量％程度で、主たる不純物として３，４−キシレノ
ール、メタエチルフェノール、パラエチルフェノール等
を含み、さらに硫黄分を１００〜３０００ｐｐｍ程度及
び窒素骨を１０〜５０００ｐｐｍ程度含んでいるもので
ある。The 3,5-xylenol fraction is obtained from a tar fraction by means such as distillation, and has a purity of 3,5-xylenol of about 60 to 92% by weight, preferably 73 to 8%.
It contains 3,4-xylenol, metaethylphenol, paraethylphenol, etc. as main impurities, and further contains about 100 to 3000 ppm of sulfur and about 10 to 5000 ppm of nitrogen bones.
ｎ−ヘプタンの添加量は、３，５−キシレノール画分１
００重量部に対し１００〜１０００重量部程度、特に１
００〜３００重量部程度が好ましい。添加時期は３，５
−キシレノール画分の溶融状態であってもよいが５０〜
２０℃程度、好ましくは３０〜２０℃程度までまず冷却
して３．５−キシレノールを一部品析させてからｎ−ヘ
プタンを加えることが好ましい。ｎ−ヘプタンの添加中
は適宜撹拌する。添加方法には特に困難はなく、通常は
一度に添加すればよい。添加後はさらに冷却して晶析率
を高めることが好ましい。冷却温度としては０〜−２０
℃程度が適当である。The amount of n-heptane added is 3,5-xylenol fraction 1
About 100 to 1000 parts by weight, especially 1
The amount is preferably about 00 to 300 parts by weight. Addition time is 3,5
- The xylenol fraction may be in a molten state, but the
It is preferable to first cool the mixture to about 20°C, preferably about 30 to 20°C to partially separate 3,5-xylenol, and then add n-heptane. Stir appropriately during addition of n-heptane. There is no particular difficulty in adding it, and it is usually sufficient to add it all at once. After addition, it is preferable to further cool the mixture to increase the crystallization rate. Cooling temperature: 0 to -20
Approximately ℃ is appropriate.
この添加による３、５−キシレノールを含む結晶の精製
方法における回収率は、洗浄時および固液分離時に冷却
をすることにより高まる。第１図は、実施例に掲げた種
々の濃度の原料を原料に対して約３倍量のｎ−ヘプタン
で洗浄したときの温度と回収率の関係である。図中Ａは
原料純度が８５％の場合を、Ｂは８２％の場合をそして
Ｃは７３％の場合をそれぞれ示している。得られた結晶
の純度は９８％以上で、およそ一定であるので冷却によ
り回収率が高まる効果は大きいと言える。The recovery rate in the method for purifying crystals containing 3,5-xylenol by this addition is increased by cooling during washing and solid-liquid separation. FIG. 1 shows the relationship between temperature and recovery rate when raw materials of various concentrations listed in Examples were washed with n-heptane in an amount approximately three times the amount of the raw materials. In the figure, A shows the case where the raw material purity is 85%, B shows the case where it is 82%, and C shows the case where the raw material purity is 73%. Since the purity of the obtained crystals is 98% or more and approximately constant, it can be said that cooling has a great effect of increasing the recovery rate.
冷却後は遠心分離、濾過等の手段で固液分離する。結晶
はさらにｎ−ヘプタン等で洗浄することが好ましい。洗
浄液はｎ−ヘプタン以外にはｎ−ヘキサン、２，２−ジ
メチルブタン、シクロヘキサン等を挙げることができる
。After cooling, solid-liquid separation is performed by centrifugation, filtration, or other means. Preferably, the crystals are further washed with n-heptane or the like. In addition to n-heptane, the cleaning liquid may include n-hexane, 2,2-dimethylbutane, cyclohexane, and the like.
分離した結晶は、通常は純度が９８％以上、特に９９．
５％以上であり、乾燥してそのまま製品結晶とすること
ができる。しかしながら、原料の純度が低い場合には９
８％未満になることもあり、その場合には本発明の方法
を繰返すなどしてさらに精製する。一方、母液及び結晶
洗浄液は蒸留等によりｎ−ヘプタンを回収し、残余を原
料を製造する蒸留工程へ循環すれば３，５−キシレノー
ルの収率をさらに高めることができる。The separated crystals usually have a purity of 98% or higher, especially 99% purity.
The content is 5% or more, and it can be dried to form product crystals as it is. However, if the purity of the raw material is low, 9
In some cases, it may be less than 8%, in which case the method of the present invention is repeated for further purification. On the other hand, the yield of 3,5-xylenol can be further increased by recovering n-heptane from the mother liquor and crystal washing solution by distillation or the like, and circulating the remainder to the distillation process for producing raw materials.
〔作用〕
ｎ−ヘプタンは３，５−キシレノールをほとんど溶解せ
ず、一方、メタエチルフェノールやバラエチルフェノー
ルを溶解するところがらｎ−ヘプタンの存在下で晶析を
行なうことにより、これら不純物の結晶への取込みをな
くし、また結晶に付着する母液のこれらの濃度を低下さ
せて結晶純度の向上に付与している。[Function] n-heptane hardly dissolves 3,5-xylenol, but on the other hand, it dissolves metaethylphenol and paraethylphenol, but by crystallizing in the presence of n-heptane, the crystals of these impurities are removed. This improves the purity of the crystals by eliminating their incorporation into the crystals and reducing the concentration of these in the mother liquor adhering to the crystals.
（実施例〕
実施例１
タール留分から抽出により得たタール酸を蒸留して、表
−１に記載の組成の３．５−キシレノールの濃度を高め
た原料を作成した。この原料１００部を完全に融解し、
常温で冷却して一部を結晶化させた。その後、ｎ−ヘプ
タン１００部を加え一１０℃で撹拌をした。吸引濾過器
により固液分離し、−１０℃に予冷した２００部のｎ−
ヘプタン溶剤で結晶を洗浄した。固相の溶媒を除いた重
量は７３部であり、その分析結果を表−１に掲げた。こ
のように簡単な操作で、高純度でＮ−３含有量が低く、
しかも経時着色も無い３，５−キシレノールが高回収率
で得られた。(Example) Example 1 A raw material with an increased concentration of 3,5-xylenol having the composition shown in Table 1 was prepared by distilling tar acid obtained by extraction from a tar fraction.100 parts of this raw material was completely melts into
It was cooled to room temperature to partially crystallize it. Then, 100 parts of n-heptane was added and stirred at -10°C. Solid-liquid separation was performed using a suction filter, and 200 parts of n-
The crystals were washed with heptane solvent. The weight of the solid phase excluding the solvent was 73 parts, and the analysis results are listed in Table 1. With this simple operation, high purity and low N-3 content can be obtained.
Furthermore, 3,5-xylenol was obtained with a high recovery rate and was free from coloration over time.
表−１
（単位は４％）
原料 結晶
３．５−キシレノール ８５．０ ９９．
６３．４−キシレノール １．０ ０．
３メタエチルフエノール ６．Ｏｔｒａｃｅパラエ
チルフェノール ４．３ ｔｒａｃｅＳ ｐｐ
ｍ １１７．０ ２３．０（
単位は智ｔ％）
原料 結晶
Ｎ ｐｐｍ １８．０ ３．
０経時着色 なし３．５−
キシレノール回収率 −８５，７比較例１
実施例１と同じ原料１００部を溶解後、徐冷し４０℃で
固液分離を行なった。その固相を融解後徐冷し、４５℃
で固液分離を行なった。さらに、その固相を融解後徐冷
し、５０℃で固液分劇を行なって固相４２部を得た。処
理前後の分析結果を表−２に掲げた。Table-1 (Unit: 4%) Raw material Crystalline 3.5-xylenol 85.0 99.
63.4-xylenol 1.0 0.
3 metaethylphenol 6. Otrace paraethylphenol 4.3 traceS pp
m 117.0 23.0 (
(Unit: t%) Raw material Crystal N ppm 18.0 3.
0 No coloration over time 3.5-
Xylenol recovery rate -85.7 Comparative Example 1 After dissolving 100 parts of the same raw material as in Example 1, it was slowly cooled and solid-liquid separation was performed at 40°C. After melting the solid phase, it was slowly cooled to 45°C.
Solid-liquid separation was performed. Further, the solid phase was melted and slowly cooled, and solid-liquid separation was performed at 50°C to obtain 42 parts of the solid phase. The analysis results before and after treatment are listed in Table 2.
このように、溶剤を使用しない晶析による精製方法では
多段で行っても純度や回収率、その他の品質において十
分なものが得られなかった。As described above, purification methods using crystallization that do not use solvents have not been able to obtain sufficient purity, recovery rate, and other qualities even when performed in multiple stages.
表−２
（単位は−ｔ％）
原料 結晶
３．５−キシレノール ８５．０ ９２．
２３．４−キシレノール １．６ ０．
５メタエチルフエノール ６．０ ４．０パラ
エチルフエノール ４．３ ２．６Ｓ ｐｐｍ
１１７．０ ６３．ＯＮ
ｐｐｍ １Ｂ、０ １４．０
（単位は讐ｔ％）
原料 結晶
経時着色 −あり
３．５−キシレノール回収率 −４５，６実施例２
実施例１と同様な操作で、処理温度を１０″Ｃおよび２
６℃で行った結果を表−３に掲げた。２６℃のものは１
０℃や一１０℃で行ったものより回収率が低い。Table 2 (Unit: -t%) Raw material Crystalline 3.5-xylenol 85.0 92.
23.4-xylenol 1.6 0.
5 Metaethylphenol 6.0 4.0 Paraethylphenol 4.3 2.6S ppm
117.0 63. ON
ppm 1B, 0 14.0
(Units are t%) Raw materials Crystal coloring over time - Present 3.5-xylenol recovery rate - 45,6 Example 2 The same procedure as in Example 1 was carried out, with the treatment temperature being 10"C and 2
The results obtained at 6°C are listed in Table 3. 26℃ is 1
The recovery rate is lower than those conducted at 0°C or -10°C.
表−３
原 料 １０℃処理 ２６℃処理
実施例３
実施例１と同様な操作で３，５−キシレノール純度が８
２．１％のものを原料に、処理温度を一１０″Ｃ１１２
℃および２１℃でｎ−ヘプタンによる洗浄を行った結果
を表−４に掲げた。２１℃のものは、−１０″Ｃや１２
℃で行ったものより回収率が低い。このように、Ｎ−３
が高い試料を用いても十分な精製効果がある。Table-3 Raw material 10℃ treatment 26℃ treatment Example 3 3,5-xylenol purity was 8 by the same operation as Example 1.
Using 2.1% as raw material, the processing temperature was -10"C112
Table 4 lists the results of washing with n-heptane at 21°C and 21°C. 21℃ is -10''C or 12
The recovery rate is lower than that performed at °C. In this way, N-3
A sufficient purification effect can be obtained even when using a sample with a high
表−４
（単位はｗｔ％）
３．５−キシレノール ８２．１ １００．
０ ９９．８ １００．０３・４−キシレノール
１．３ ｔｒａｃｅ ｔｒａｃｅ
ｔｒａｃｅメタエチルフェノール ８．９
ｔｒａｃｅ Ｏ，２ｔｒａｃｅ実施例４
実施例１と同様な操作で、３，５−キシレノール純度が
７２．９％のものを原料に、処理温度を一１０’ｃ。Table 4 (Units are wt%) 3.5-xylenol 82.1 100.
0 99.8 100.03・4-xylenol 1.3 trace trace
trace metaethylphenol 8.9
trace O, 2trace Example 4 In the same manner as in Example 1, 3,5-xylenol with a purity of 72.9% was used as a raw material, and the treatment temperature was -10'C.
１ ”Ｃおよび２１”Ｃでｎ−ヘプタンによる洗浄を行
った結果を表−５に掲げた。２１”Ｃのものは、−１０
″Ｃや１℃で行ったものより回収率が低い。The results of cleaning with n-heptane at 1"C and 21"C are listed in Table 5. 21”C is -10
The recovery rate is lower than that conducted at 1°C or 1°C.
（以下余白）
表−５
（単位はｗｔ％）
実施例５及び比較例２．３
実施例１と同様の方法で３，５−キシレノール濃度が８
２．１％のものを原料に、処理温度を２１℃で溶剤をｎ
−ヘキサン、ｎ−ヘプタン及び２，２−ジメチルブタン
で試験を行った結果とそれぞれのアニリン点を表−６に
掲げた。アニリン点が高くなるほど回収率が高まる。(Margins below) Table 5 (Units are wt%) Example 5 and Comparative Example 2.3 The 3,5-xylenol concentration was reduced to 8 in the same manner as in Example 1.
Using 2.1% as raw material, the treatment temperature was 21℃ and the solvent was
Table 6 lists the results of tests conducted with -hexane, n-heptane and 2,2-dimethylbutane and the respective aniline points. The higher the aniline point, the higher the recovery rate.
／ＩＮＩ□人□＼
表−６
（単位は−ｔ％
実施例６及び比較例４〜６
実施例１と同様の方法で３，５−キシレノール濃度が７
２．９％のものを原料に、処理温度を１℃で溶剤をｎ−
ヘキサン、ｎ−ヘプタンおよび２，２−ジメチルブタン
およびシクロヘキサンで試験を行った結果とそれぞれの
アニリン点を表−７に掲げた。実施例５と同様にアニリ
ン点が高くなるほど回収率が高まる。/INI□人□＼ Table 6 (Unit: -t%) Example 6 and Comparative Examples 4 to 6 The concentration of 3,5-xylenol was 7 in the same manner as in Example 1.
Using 2.9% as raw material, the treatment temperature was 1℃ and the solvent was n-
Table 7 lists the results of tests with hexane, n-heptane, 2,2-dimethylbutane, and cyclohexane, and the aniline points of each. As in Example 5, the higher the aniline point, the higher the recovery rate.
表−７
３，５−キシレノール ７２．９ ９８．
１ ９９．６ ９９．３ ９９．０３．４−キ
シレノール ０．３ １．８ ｔｒ
ａｃｅ Ｏ，２ｔｒａｃｅメタエチル７ｘノール１
３．９ ｔｒａｃｅ ｔｒａｃｅ ｔｒａｃ
ｅ ｔｒａｃｅパラエチルフェノール １０
．６ ｔｒａｃｅ Ｏ，２０，３０，４経時
着色 −なし なし なし
なし３．５−キシレノール回収率 −６０，２５
５，８４９，４３７，６溶剤のアニリン点（’Ｃ）
−８１，２７０，６６３，６３１，０〔発明の効果
〕
以上のように、この発明によれば３．５−キシレノール
を含む結晶をｎ−ヘプタンで洗浄することにより、従来
の晶析法では得られなかった高回収率で高純度の３，５
−キシレノールを得ることができる。Table-7 3,5-xylenol 72.9 98.
1 99.6 99.3 99.03.4-xylenol 0.3 1.8 tr
ace O, 2trace metaethyl 7x norl 1
3.9 trace trace trac
e trace paraethylphenol 10
．． 6 trace O, 20, 30, 4 Coloring over time - None None None
None 3.5-xylenol recovery rate -60,25
Aniline point ('C) of 5,849,437,6 solvent
-81,270,663,631,0 [Effects of the Invention] As described above, according to the present invention, by washing crystals containing 3,5-xylenol with n-heptane, it is possible to obtain High recovery rate and high purity 3,5
- xylenol can be obtained.
第１図は各種純度の原料について、処理温度と３．５−
キシレノールの回収率の関係を測定した結果を示すグラ
フである。
特許出願人 アドケムコ株式会社
代 理 人 弁理士 日中 政情
第１図
温度（’Ｃ）Figure 1 shows the processing temperature and 3.5-
It is a graph showing the results of measuring the relationship between the recovery rates of xylenol. Patent Applicant Adchemco Co., Ltd. Agent Patent Attorney Japan-China Political Situation Figure 1 Temperature ('C)
Claims (1)
ｎ−ヘプタンを加え、０〜−２０℃に冷却した後固液分
離することを特徴とする３，５−キシレノールの精製方
法A method for purifying 3,5-xylenol, which comprises adding n-heptane to a 3,5-xylenol fraction separated from a tar fraction, cooling it to 0 to -20°C, and then performing solid-liquid separation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31140190A JPH04182444A (en) | 1990-11-19 | 1990-11-19 | Method for purifying 3,5-xylenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31140190A JPH04182444A (en) | 1990-11-19 | 1990-11-19 | Method for purifying 3,5-xylenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04182444A true JPH04182444A (en) | 1992-06-30 |
Family
ID=18016754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31140190A Pending JPH04182444A (en) | 1990-11-19 | 1990-11-19 | Method for purifying 3,5-xylenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04182444A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9361907B2 (en) | 2011-01-18 | 2016-06-07 | Sony Corporation | Sound signal processing apparatus, sound signal processing method, and program |
-
1990
- 1990-11-19 JP JP31140190A patent/JPH04182444A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9361907B2 (en) | 2011-01-18 | 2016-06-07 | Sony Corporation | Sound signal processing apparatus, sound signal processing method, and program |
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