JP3270562B2 - Method for producing acicular isopropylmethylphenol - Google Patents
Method for producing acicular isopropylmethylphenolInfo
- Publication number
- JP3270562B2 JP3270562B2 JP05789993A JP5789993A JP3270562B2 JP 3270562 B2 JP3270562 B2 JP 3270562B2 JP 05789993 A JP05789993 A JP 05789993A JP 5789993 A JP5789993 A JP 5789993A JP 3270562 B2 JP3270562 B2 JP 3270562B2
- Authority
- JP
- Japan
- Prior art keywords
- 4i5mp
- carbon dioxide
- tank
- solvent
- extraction
- 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 - Fee Related
Links
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 title claims description 8
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 54
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 27
- 239000001569 carbon dioxide Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 description 22
- 238000004090 dissolution Methods 0.000 description 18
- 238000000605 extraction Methods 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000005844 Thymol Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、針状イソプロピルメチ
ルフェノールの製造方法に関するものであり、詳しく
は、針状４−イソプロピル−５−メチルフェノール（以
下、「４Ｉ５ＭＰ」と略記する。）の工業的に有利な製
造方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing acicular isopropylmethylphenol, and more particularly, to the production of acicular 4-isopropyl-5-methylphenol (hereinafter abbreviated as "4I5MP"). The present invention relates to an economically advantageous production method.
【０００２】[0002]
【従来の技術】４Ｉ５ＭＰは、殺菌性、抗酸化性などの
特性を有し、医薬品、化粧品に広く使用されている。４
Ｉ５ＭＰは、２−イソプロピル−５−メチルフェノール
（所謂チモール）の異性体である。そして、両者は、例
えば、メタ−クレゾールと塩化イソプロピルとを原料と
するアルキル化反応によって得られ、蒸留により成分分
離して回収される。2. Description of the Related Art 4I5MP has properties such as bactericidal properties and antioxidant properties, and is widely used in pharmaceuticals and cosmetics. 4
I5MP is an isomer of 2-isopropyl-5-methylphenol (so-called thymol). Both are obtained, for example, by an alkylation reaction using meta-cresol and isopropyl chloride as raw materials, and are separated and recovered by distillation.
【０００３】チモールは融点５１．５℃であるが、４Ｉ
５ＭＰは、融点１１１〜１１３°Ｃの無色または白色の
結晶性固体である。４Ｉ５ＭＰの結晶形としては、塊
状、柱状、粒状、針状、綿状などが知られているが、高
純度の４Ｉ５ＭＰの結晶形は針状である。そして、取扱
いの容易さや純度の観点から、長さ３〜１０ｍｍ程度の
針状４Ｉ５ＭＰが好まれている。Thymol has a melting point of 51.5 ° C.
5MP is a colorless or white crystalline solid with a melting point of 111-113 ° C. As the crystal form of 4I5MP, lumps, columns, grains, needles, cotton, and the like are known, but the crystal form of high-purity 4I5MP is acicular. From the viewpoint of ease of handling and purity, acicular 4I5MP having a length of about 3 to 10 mm is preferred.
【０００４】従来、４Ｉ５ＭＰの高純度化としては、溶
媒として、ｎ−ヘキサン、石油ベンジン、リグロイン等
を使用した晶析法が知られているが、斯かる晶析法で
は、強引火性の溶媒を使用するために安全上問題があ
る。一方、引火点が比較的高い高沸点の石油系溶媒を使
用する晶析法では、得られる針状４Ｉ５ＭＰ中に溶媒が
残留して純度が低下すると言う問題がある。Conventionally, as a method for purifying 4I5MP, a crystallization method using n-hexane, petroleum benzene, ligroin, or the like as a solvent is known. In such a crystallization method, a strongly flammable solvent is used. There are safety issues to use. On the other hand, in the crystallization method using a high boiling point petroleum solvent having a relatively high flash point, there is a problem that the solvent remains in the obtained acicular 4I5MP and the purity is reduced.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、上記実情に
鑑みなされたものであり、その目的は、針状４Ｉ５ＭＰ
の製造方法であって、引火性の溶媒を使用せず且つ溶媒
の残留問題がない工業的有利な製造方法を提供すること
にある。SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned circumstances, and has as its object a needle-like 4I5MP
It is an object of the present invention to provide an industrially advantageous production method which does not use a flammable solvent and has no problem of residual solvent.
【０００６】[0006]
【課題を解決するための手段】本発明者等は、上記の目
的を達成すべく種々検討を重ねた結果、晶析溶媒とし
て、超臨界または液体状態の二酸化炭素を使用するなら
ば、意外にも、針状に十分発達した４Ｉ５ＭＰの結晶が
得られることを知見し、本発明の完成に至った。The present inventors have made various studies to achieve the above object, and as a result, if carbon dioxide in a supercritical or liquid state is used as a crystallization solvent, surprisingly, Also found that 4I5MP crystals sufficiently developed in the form of needles were obtained, and the present invention was completed.
【０００７】すなわち、本発明の要旨は、溶媒として超
臨界または液体状態の二酸化炭素を使用して４−イソプ
ロピル−５−メチルフェノールを晶析処理することを特
徴とする針状イソプロピルメチルフェノールの製造方法
に存する。That is, the gist of the present invention is to produce acicular isopropylmethylphenol by crystallizing 4-isopropyl-5-methylphenol using supercritical or liquid carbon dioxide as a solvent. Be in the way.
【０００８】以下、本発明を詳細に説明する。図１は本
発明の実施に使用される晶析プロセスの一例を示す説明
図である。晶析プロセスは、通常、回分方式によって行
われる。原料の粗製４Ｉ５ＭＰは、抽出溶解槽（５）に
仕込まれる。通常、純度が９８〜９９％程度の粗製４Ｉ
５ＭＰが使用される。斯かる粗製４Ｉ５ＭＰの結晶形は
粉状または粒状である。Hereinafter, the present invention will be described in detail. FIG. 1 is an explanatory view showing an example of a crystallization process used for carrying out the present invention. The crystallization process is usually performed in a batch mode. The raw 4I5MP raw material is charged into the extraction dissolution tank (5). Normally, crude 4I with a purity of about 98-99%
5MP is used. The crystalline form of such crude 4I5MP is powdery or granular.
【０００９】二酸化炭素は、液化炭酸ガスボンベ（１）
から、バルブ（９）、フィルター（１０）を経た後、液
化炭酸ガスポンプ（３）により、加温器（４）、逆止弁
（１１）、バルブ（１２）を経て抽出溶解槽（５）に供
給される。この供給ラインの途中には、冷却機（２）が
設けられている。Carbon dioxide is liquefied carbon dioxide gas cylinder (1)
After passing through a valve (9) and a filter (10), the liquefied carbon dioxide gas pump (3) passes through a heater (4), a check valve (11) and a valve (12) to an extraction dissolution tank (5). Supplied. A cooler (2) is provided in the middle of the supply line.
【００１０】抽出溶解槽（５）に供給された二酸化炭素
は、抽出溶解槽（５）に付属した加温器（４）及び圧力
調整弁（１３）を調節することにより、超臨界状態また
は液体状態に維持される。以下、斯かる状態の二酸化炭
素を「二酸化炭素溶媒」と略記する。The carbon dioxide supplied to the extraction / dissolution tank (5) is supplied to the extraction / dissolution tank (5) by adjusting a heater (4) and a pressure regulating valve (13) attached thereto so as to be in a supercritical state or a liquid state. Maintained in state. Hereinafter, carbon dioxide in such a state is abbreviated as “carbon dioxide solvent”.
【００１１】二酸化炭素溶媒を得るための条件は、通
常、圧力５０〜５００ｋｇ／ｃｍ2 、温度１０〜１００
℃の範囲から選択されるが、溶解効率の点から、圧力７
０〜５００ｋｇ／ｃｍ2 、好ましくは２００〜４００ｋ
ｇ／ｃｍ2 、温度３５〜６０℃の範囲から選択するのが
好ましい。The conditions for obtaining the carbon dioxide solvent are usually a pressure of 50 to 500 kg / cm 2 and a temperature of 10 to 100 kg / cm 2 .
° C range, but from the viewpoint of dissolution efficiency, pressure 7
0 to 500 kg / cm 2 , preferably 200 to 400 k
g / cm 2 and a temperature in the range of 35 to 60 ° C. are preferred.
【００１２】抽出溶解槽（５）の後に順次連結された第
１分離槽（６）及び第２分離槽（７）は、必要に応じて
設けられる。そして、各付属の加温器と圧力調整弁（１
３）及び（１４）を調節し、必要な条件が設定される。
二酸化炭素溶媒に溶解した４Ｉ５ＭＰは、溶解時の温度
及び／又は圧力を低下または減少させて超臨界乃至は液
体状態を解除することにより、抽出溶解槽（５）又は第
１分離槽（６）及び第２分離槽（７）の中で析出させら
れる。何れの槽で析出を行うかは、工程上の要望によ
り、任意に決定することが出来る。そして、分離槽を並
列に設置した場合は、各分離槽を交互に系列から遮断し
て析出物を取り出すことにより、効率化を図ることが出
来る。A first separation tank (6) and a second separation tank (7), which are sequentially connected after the extraction / dissolution tank (5), are provided as needed. Then, each attached heater and pressure regulating valve (1
3) and (14) are adjusted, and necessary conditions are set.
4I5MP dissolved in a carbon dioxide solvent reduces or reduces the temperature and / or pressure during dissolution to release the supercritical or liquid state, thereby allowing the extraction dissolution tank (5) or the first separation tank (6) and It is precipitated in a second separation tank (7). Which tank is used for precipitation can be arbitrarily determined according to the demands of the process. When the separation tanks are installed in parallel, the efficiency can be improved by alternately shutting off the respective separation tanks from the series and extracting the precipitate.
【００１３】上記の温度及び／又は圧力の低下または減
少操作は、徐々に行うことが重要であり、温度または圧
力を急激に低下または減少させた場合は、粉状または粒
状の４Ｉ５ＭＰが折出し、針状の４Ｉ５ＭＰが得られな
い。そして、実際の析出条件は、適用温度や圧力、４Ｉ
５ＭＰの溶解量などによって異なるために一概には決定
し得ないが、予備実験によって容易に求めることが出来
る。It is important that the above-mentioned operation of lowering or reducing the temperature and / or pressure is performed gradually. When the temperature or pressure is rapidly reduced or reduced, powdery or granular 4I5MP is deposited, Needle-like 4I5MP cannot be obtained. The actual deposition conditions include the application temperature and pressure,
Since it depends on the amount of 5MP dissolved, it cannot be unconditionally determined, but can be easily determined by preliminary experiments.
【００１４】二酸化炭素溶媒に対して４Ｉ５ＭＰより溶
解性が高い不純物が含まれている粗製４Ｉ５ＭＰを使用
した場合は、４Ｉ５ＭＰの折出に先立ち、濃縮された上
記の不純物を除去することにより、針状４Ｉ５ＭＰの純
度を高めることが出来る。また、二酸化炭素溶媒に対し
て４Ｉ５ＭＰより溶解性が低い不純物が含まれている場
合は、例えば、多段晶析を行い、上記の不純物を濃縮し
た初期抽出分を除去することにより、針状４Ｉ５ＭＰの
純度を高めることが出来る。When crude 4I5MP containing impurities more soluble in carbon dioxide solvent than 4I5MP is used, prior to the 4I5MP separation, the above-mentioned concentrated impurities are removed to obtain a needle-like shape. The purity of 4I5MP can be increased. In addition, when impurities having lower solubility than 4I5MP are contained in the carbon dioxide solvent, for example, multistage crystallization is performed, and the initial extract obtained by concentrating the above impurities is removed. Purity can be increased.
【００１５】二酸化炭素溶媒は、使用後、ガスとして流
量計（８）を経たのち系外へ放出させられるが、その放
出に伴って流出する４Ｉ５ＭＰは、適当なトラップ（図
示せず）にて回収することが出来る。また、二酸化炭素
は、回収して加圧することにより、循環して使用するこ
とが出来る。After use, the carbon dioxide solvent is released as a gas after passing through a flow meter (8), and the 4I5MP flowing out with the release is collected by an appropriate trap (not shown). You can do it. The carbon dioxide can be circulated and used by collecting and pressurizing.
【００１６】[0016]
【実施例】以下、本発明を実施例によって更に詳細に説
明するが、本発明はその要旨を超えない限り、以下の実
施例に制約されるものではない。なお、以下の実施例に
おいては、図１に示した晶析プロセスを使用したが、抽
出溶解槽（５）、第１分離槽（６）及び第２分離槽
（７）の容量はいずれも０．５リットルである。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. In the following examples, the crystallization process shown in FIG. 1 was used, but the volumes of the extraction dissolution tank (5), the first separation tank (6) and the second separation tank (7) were all 0. 0.5 liters.
【００１７】実施例１ 抽出溶解槽（５）に１０ｇの粉状粗製４Ｉ５ＭＰ（純度
９９．２％）を仕込んだ。次いで、バルブ（９）及び
（１２）を開とし、液化炭酸ガスポンプ（３）を駆動さ
せ、各槽に付属の加温器と圧力調整弁（１３）〜（１
５）を調節して表１に示す条件に設定した。Example 1 10 g of powdery crude 4I5MP (purity: 99.2%) was charged into an extraction dissolution tank (5). Next, the valves (9) and (12) are opened, the liquefied carbon dioxide gas pump (3) is driven, and the heaters and pressure regulating valves (13) to (1) attached to each tank are provided.
5) was adjusted to set the conditions shown in Table 1.
【００１８】[0018]
【表１】 ──────────────────────────── 圧力（Ｋｇ／ｃｍ2 ） 温度（℃） 抽出溶解層（５） ３００ ４０ 第１分離層（６） ３００ ４０ 第２分離層（７） １５０ ３０ トラップ（図示せず） 大気圧 ── ────────────────────────────Table 1 Pressure (Kg / cm 2 ) Temperature (° C) Extraction and dissolution layer (5) 300 40 First separation layer (6) 300 40 Second separation layer (7) 150 30 Trap (not shown) Atmospheric pressure {} ───────
【００１９】設定条件到達後、二酸化炭素の供給を停止
し、その状態を維持して１時間放置した。二酸化炭素の
供給量は５７０リットルであった。次いで、約６リット
ル／ｍｉｎの速度で系内の二酸化炭素を放出させて各槽
の溶解物を晶析させた。各槽で得られた結晶の重量を計
量し、その結果を表２に示した。After the set conditions were reached, the supply of carbon dioxide was stopped, and the state was maintained for one hour. The supply of carbon dioxide was 570 liters. Next, carbon dioxide in the system was released at a rate of about 6 liters / min to crystallize the melt in each tank. The weight of the crystals obtained in each tank was weighed, and the results are shown in Table 2.
【００２０】抽出溶解槽（５）の下部には、粉状と針状
の混在した４Ｉ５ＭＰが析出し、上部には、針状の４Ｉ
５ＭＰが析出した。第１分離槽（６）と第２分離槽
（７）には白色針状の４Ｉ５ＭＰが析出した。その長さ
は約５〜１５ｍｍであり、純度は９９．８％であった。At the lower part of the extraction dissolution tank (5), powdery and needle-like 4I5MP are deposited, and at the upper part, needle-like 4I5MP is precipitated.
5MP precipitated. White needle-like 4I5MP was deposited in the first separation tank (6) and the second separation tank (7). Its length was about 5 to 15 mm and the purity was 99.8%.
【００２１】実施例２ 抽出溶解槽（５）への粉状粗製４Ｉ５ＭＰの仕込み量を
５ｇに変更した意外は、実施例１と同様に行った。各槽
で得られた結晶の重量を計量し、その結果を表２に示し
た。抽出溶解槽（５）の下部には、粉状と針状の混在し
た４Ｉ５ＭＰが析出し、上部には、針状の４Ｉ５ＭＰが
析出した。第１分離槽（６）と第２分離槽（７）には白
色針状の４Ｉ５ＭＰが析出した。その長さは約５〜１５
ｍｍであり、純度は９９．７％であった。Example 2 The procedure of Example 1 was repeated, except that the amount of the powdery crude 4I5MP charged into the extraction dissolution tank (5) was changed to 5 g. The weight of the crystals obtained in each tank was weighed, and the results are shown in Table 2. At the lower part of the extraction dissolution tank (5), powdery and needle-like 4I5MP were deposited, and at the upper part, needle-like 4I5MP was deposited. White needle-like 4I5MP was deposited in the first separation tank (6) and the second separation tank (7). Its length is about 5-15
mm and the purity was 99.7%.
【００２２】実施例３ 抽出溶解槽（５）に３０ｇの粉状粗製４Ｉ５ＭＰ（純度
９９．２％）を仕込んだ後、各槽の条件を実施例１と同
一条件に設定した。設定条件到達後、その状態で二酸化
炭素の供給を停止し１時間放置した。その後、上記の条
件を維持して５リットル／ｍｉｎの速度で二酸化炭素を
供給し、４Ｉ５ＭＰを溶解した二酸化炭素流体を第１分
離槽に移行させた。Example 3 After charging 30 g of powdery crude 4I5MP (purity 99.2%) into the extraction dissolution tank (5), the conditions of each tank were set to the same conditions as in Example 1. After the set conditions were reached, the supply of carbon dioxide was stopped in that state and left for 1 hour. Thereafter, while maintaining the above conditions, carbon dioxide was supplied at a rate of 5 liter / min, and the carbon dioxide fluid in which 4I5MP was dissolved was transferred to the first separation tank.
【００２３】二酸化炭素の総量が７５０リットルに達し
た時、二酸化炭素の供給を止め、約６リットル／ｍｉｎ
の速度で系内の二酸化炭素を放出させて各槽の溶解物を
晶析させた。各槽で得られた結晶の重量を計量し、その
結果を表２に示した。抽出溶解槽（５）の下部には、粉
状と針状の混在した４Ｉ５ＭＰが析出し、上部には、針
状の４Ｉ５ＭＰが析出した。第１分離槽（６）と第２分
離槽（７）には白色針状の４Ｉ５ＭＰが析出した。その
長さは約５〜１５ｍｍであり、純度は９９．８％であっ
た。When the total amount of carbon dioxide reaches 750 liters, the supply of carbon dioxide is stopped and about 6 liters / min
The carbon dioxide in the system was released at the speed of and the melt in each tank was crystallized. The weight of the crystals obtained in each tank was weighed, and the results are shown in Table 2. At the lower part of the extraction dissolution tank (5), powdery and needle-like 4I5MP were deposited, and at the upper part, needle-like 4I5MP was deposited. White needle-like 4I5MP was deposited in the first separation tank (6) and the second separation tank (7). Its length was about 5 to 15 mm and the purity was 99.8%.
【００２４】[0024]
【表２】 ─────────────────────────────── 実施例１ 実施例２ 実施例３ 抽出溶解層（５） 下部（ｇ） ３．８ ０．５ ２０．６ 上部（ｇ） ２．４ ２．５ ２．６ 第１分離層(6) （ｇ） ０．６ ０．７ １．６ 第２分離層(7) （ｇ） ０．２ ０．１ ０．４ 未回収量分（ｇ） ３．０ １．２ ４．８ ───────────────────────────────Table 2 Example 1 Example 2 Example 3 Extraction dissolution layer (5) Lower (g) 3.8 0.5 20.6 Upper (g) 2.4 2.5 2.6 First separation layer (6) (g) 0.6 0.7 1.6 Second separation layer ( 7) (g) 0.2 0.1 0.4 Uncollected amount (g) 3.0 1.2 4.8 ──────────────────── ───────────
【００２５】[0025]
【発明の効果】以上説明した本発明の製造方法によれ
ば、引火性の溶媒を使用せず且つ溶媒の残留問題がない
工業的有利な製造方法により、針状に十分発達して高純
度な４−イソプロピル−５−メチルフェノールが得られ
る。According to the production method of the present invention described above, an industrially advantageous production method that does not use a flammable solvent and has no problem of residual solvent is sufficiently developed into a needle-like shape and high purity. 4-Isopropyl-5-methylphenol is obtained.
【図１】本発明の実施に使用される晶析プロセスの一例
を示す説明図である。FIG. 1 is an explanatory diagram showing an example of a crystallization process used for carrying out the present invention.
１：液化炭酸ガスボンベ ２：冷却機 ３：液化炭酸ガスポンプ ４：加温器 ５：抽出溶解槽 ６：第１分離槽 ７：第２分離槽 ８：流量計 1: Liquefied carbon dioxide gas cylinder 2: Cooler 3: Liquefied carbon dioxide gas pump 4: Heater 5: Extraction dissolution tank 6: First separation tank 7: Second separation tank 8: Flow meter
───────────────────────────────────────────────────── フロントページの続き (72)発明者 田中 爲彦 大阪市西淀川区中島二丁目６番11号 大 阪化成株式会社 本社工場内 (72)発明者 田波 久紀夫 大阪市西淀川区中島二丁目６番11号 大 阪化成株式会社 本社工場内 (56)参考文献 特開 平３−287550（ＪＰ，Ａ) 特開 平２−277505（ＪＰ，Ａ) 特開 平２−214503（ＪＰ，Ａ) 特開 平１−266804（ＪＰ，Ａ) 特開 昭52−131536（ＪＰ，Ａ) 特開 昭49−56936（ＪＰ，Ａ) 特公 昭39−19789（ＪＰ，Ｂ１) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 39/06 C07C 37/84 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Tamehiko Tanaka 2-6-111 Nakashima, Nishiyodogawa-ku, Osaka-shi In the head office plant of Osaka Chemicals Co., Ltd. No. 11 Osaka Chemical Co., Ltd. Headquarters factory (56) References JP-A-3-287550 (JP, A) JP-A-2-277505 (JP, A) JP-A-2-214503 (JP, A) JP-A-1-266804 (JP, A) JP-A-52-131536 (JP, A) JP-A-49-56936 (JP, A) JP-B-39-19789 (JP, B1) (58) Int.Cl. 7 , DB name) C07C 39/06 C07C 37/84
Claims (1)
化炭素を使用して４−イソプロピル−５−メチルフェノ
ールを晶析処理することを特徴とする針状イソプロピル
メチルフェノールの製造方法。1. A process for producing needle-like isopropylmethylphenol, comprising crystallizing 4-isopropyl-5-methylphenol using carbon dioxide in a supercritical or liquid state as a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05789993A JP3270562B2 (en) | 1993-02-23 | 1993-02-23 | Method for producing acicular isopropylmethylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05789993A JP3270562B2 (en) | 1993-02-23 | 1993-02-23 | Method for producing acicular isopropylmethylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06247887A JPH06247887A (en) | 1994-09-06 |
| JP3270562B2 true JP3270562B2 (en) | 2002-04-02 |
Family
ID=13068846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05789993A Expired - Fee Related JP3270562B2 (en) | 1993-02-23 | 1993-02-23 | Method for producing acicular isopropylmethylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3270562B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6754733B2 (en) | 2001-08-23 | 2004-06-22 | Texas Instruments Incorporated | Shared memory architecture for increased bandwidth in a printer controller |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5000095B2 (en) * | 2005-03-11 | 2012-08-15 | 花王株式会社 | Method for producing organic crystal particles |
| DE102007035515A1 (en) * | 2007-07-28 | 2009-01-29 | Lanxess Deutschland Gmbh | dialkylphenols |
| CN114522640B (en) * | 2022-02-16 | 2022-09-23 | 安徽海华科技集团有限公司 | A start preheating device for phenol methylation reaction |
-
1993
- 1993-02-23 JP JP05789993A patent/JP3270562B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6754733B2 (en) | 2001-08-23 | 2004-06-22 | Texas Instruments Incorporated | Shared memory architecture for increased bandwidth in a printer controller |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06247887A (en) | 1994-09-06 |
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