JPS6281338A - Improvement of production of 2-tert-butylhydroquinone - Google Patents
Improvement of production of 2-tert-butylhydroquinoneInfo
- Publication number
- JPS6281338A JPS6281338A JP60220196A JP22019685A JPS6281338A JP S6281338 A JPS6281338 A JP S6281338A JP 60220196 A JP60220196 A JP 60220196A JP 22019685 A JP22019685 A JP 22019685A JP S6281338 A JPS6281338 A JP S6281338A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- tert
- butylhydroquinone
- hydroquinone
- phosphoric acid
- 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
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229940044119 2-tert-butylhydroquinone Drugs 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 44
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 20
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 17
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000004250 tert-Butylhydroquinone Substances 0.000 claims 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 45
- 239000002253 acid Substances 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 3
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 230000003078 antioxidant effect Effects 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 11
- 230000007423 decrease Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- LJSAJMXWXGSVNA-UHFFFAOYSA-N a805044 Chemical compound OC1=CC=C(O)C=C1.OC1=CC=C(O)C=C1 LJSAJMXWXGSVNA-UHFFFAOYSA-N 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003981 vehicle 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は食用油脂類の酸化防止剤として有用な２− ｔ
ｅｒｔ −ブチルヒドロキノンの改良された製造方法に
関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides 2-t useful as an antioxidant for edible oils and fats.
The present invention relates to an improved method for producing ert-butylhydroquinone.
一般Ｋ ２− ｔｌｒｔ −ブチルヒドロキノンはヒ
ドロキノンをイソブテンまだはｔｅｒｔ −ブチルア
ルコールでアルキル化することによって得られるが（例
えば米国特許第２７８１４０４号、第３９２９９１２号
および第４３２３７１４号参照）、２− ｔａｒｔ−ブ
チルヒドロキノンは（１）式で示される遂次反応の中間
生成物であるので、その選択的合成は比較的困難であり
、該化合物が高収率で得られる方法は少ない。The general K 2-tlrt-butylhydroquinone is obtained by alkylating hydroquinone with isobutene or tert-butyl alcohol (see e.g. U.S. Pat. Since hydroquinone is an intermediate product of the sequential reaction represented by formula (1), its selective synthesis is relatively difficult, and there are few methods by which this compound can be obtained in high yield.
ヒドロキノン ヒドロキノン
触媒としてリン酸を使用する液−液２相系による製造方
法（米国特許第２７２２５５６号）はその中でも最も優
れたものの一つである。すなわちこの方法では、リン酸
水溶液を触媒として使用し、トルエンまたはキシレンと
の２液相系においてヒドロキノンとイソブテンまたはｔ
ｅｒｔ −ブチルアルコールとを反応させて２− ｔｅ
ｒｔ −ブチルヒドロキノンを製造しており、例えば８
５チリン酸を多量に使用し反応混合物を激しく攪拌する
ことＫよって約８０チの収率で目的化合物を得ている。Hydroquinone Hydroquinone The production method using phosphoric acid as a catalyst using a liquid-liquid two-phase system (US Pat. No. 2,722,556) is one of the best among them. That is, in this method, an aqueous phosphoric acid solution is used as a catalyst, and hydroquinone and isobutene or t-
React with ert-butyl alcohol to form 2-te
rt-butylhydroquinone is produced, e.g. 8
By using a large amount of 5-thiphosphoric acid and vigorously stirring the reaction mixture, the target compound was obtained in a yield of about 80 thi.
しかしながら米国特許第２７２２５５６号の製造方法に
は次のような欠点がある：（ａ）目的化合物を約８０％
の高収率で得るためには反応系を激しく攪拌しなければ
ならないが、通常使用されるステンレス製反応器はリン
酸触媒の腐食作用を防止するために比較的機械強度の低
いグラスライニングが施こされているので、実際の反応
装置で激しい攪拌を行うことは困難である；（ｂ）高収
率を達成するためにはまた多量の高濃度（８５％ ）
ＩＪン酸水溶液が必要である。例えば８５チリン酸／ヒ
Ｐロキノンの仕込み重量比が１．７（反応液中のヒドロ
キノン濃度は１７重ｔ％）のときに２− ｔｅｒｔ−プ
チルヒドロキノンの収率は７０％以下であるが、リン酸
の量を増してこの比を６．１（反応液中のヒドロキノン
濃度は９重量％）にすると収率は８０チ近くまで上昇す
る。ここで一定容量の反応器を使用するときにはリン酸
量を増加した分だけ有機溶媒量を減少させなければなら
ないが、有機溶媒量を減少させ未ときには反応完了時の
固体析出を防止するためにヒドロキノンの仕込量を減少
させなければならない。従って１ノぐツチ当りの生産量
が低くなるので、反応速度を大きくして・々ンチ数を多
くすることにより生産量の低下を防止することが考えら
れる。しかしながら短時間の反応を繰返すことは反応前
後の時間損失が大きいので充分な生産性が得られない。However, the manufacturing method of U.S. Pat.
In order to obtain a high yield of phosphoric acid, the reaction system must be vigorously stirred, but the commonly used stainless steel reactor is lined with glass, which has relatively low mechanical strength, to prevent the corrosive effects of the phosphoric acid catalyst. (b) To achieve a high yield, a large amount of high concentration (85%) is also required.
An aqueous IJ acid solution is required. For example, when the charged weight ratio of 85 tyrinic acid/hyperquinone is 1.7 (hydroquinone concentration in the reaction solution is 17% by weight), the yield of 2-tert-butylhydroquinone is less than 70%, but the When the amount of acid is increased to make this ratio 6.1 (hydroquinone concentration in the reaction solution is 9% by weight), the yield increases to nearly 80%. When using a reactor with a fixed capacity, the amount of organic solvent must be decreased by the amount of phosphoric acid increased, but if the amount of organic solvent is decreased and the amount of organic solvent is not increased, hydroquinone is added to prevent solid precipitation upon completion of the reaction. The amount of preparation must be reduced. Therefore, since the production amount per punch is low, it is possible to prevent the decrease in the production amount by increasing the reaction rate and increasing the number of punches. However, repeating short-term reactions causes a large loss of time before and after the reaction, making it impossible to obtain sufficient productivity.
一方、特殊な液−液二相系反応器を用いて反応を連続的
に行うことにより生産性を高めることもできるが、この
ような反応器は中小規模の生産には適当ではないっまた
一般に完全混合型連続反応器は２− ｔｅｒｔ −ブチ
ルヒドロキノンのような遂次反応の中間生成物の選択性
がノ々ツチ反応器よりも劣っていることが知られている
５（ｃ）（１）式の反応は発熱反応であり、反応速度が
著しく大きいので、この反応熱のために反応の制御が困
難である。従って反応の中間生成物である２ −ｔｅｒ
ｔ −ブチルヒドロキノンを高収率で得るために、ノ
々ンチ反応の場合には中間生成物の段階で正確に反応を
停止すること、また連続反応の場合には運転を定常的に
実施することが困難である：（ｄ）Ｃ４−アルキル化剤
としてｔａｒｔ −ブチルアルコールを使用するときに
は１）一般にｔｓｒｔ −ブチルアルコールはイソブテ
ンよりも相当に高価である、ｉｉ）反応中は酸の濃度を
所望の値に維持するために生成する水を共沸して除去し
なければならないので操作が煩雑である、ｍ ＞ 共沸
温度が存在するので反応温度に制限を受ける等の不利益
がある。On the other hand, it is possible to increase productivity by conducting the reaction continuously using a special liquid-liquid two-phase reactor, but such a reactor is not suitable for medium- to small-scale production and is generally 5(c)(1) It is known that the complete mixing type continuous reactor has inferior selectivity for intermediate products of sequential reactions such as 2-tert-butylhydroquinone than the Nototsuchi reactor. The reaction of the formula is an exothermic reaction and the reaction rate is extremely high, making it difficult to control the reaction due to the reaction heat. Therefore, the intermediate product of the reaction, 2-ter
In order to obtain t-butylhydroquinone in high yield, the reaction must be stopped accurately at the intermediate product stage in the case of a multiple reaction, and the operation must be carried out regularly in the case of a continuous reaction. (d) When using tart-butyl alcohol as the C4-alkylating agent, 1) tsrt-butyl alcohol is generally much more expensive than isobutene; ii) adjusting the acid concentration to the desired level during the reaction is difficult; There are disadvantages such as the operation is complicated because the produced water must be azeotropically removed in order to maintain the same value, and the reaction temperature is limited because m > azeotropic temperature exists.
〔問題点を解決するための手段・作用〕本発明者等は、
ヒドロキノンを触媒としてのリン酸の存在下で有機溶媒
中においてイソブテンまたはｔｅｒｔ −ブチルアルコ
ールと反応させて２−ｔｅｒｔ−ブチルヒドロキノンを
製造する際に、濃度６０チのリン酸を使用するときに前
記の問題点が解決されることを見出して本発明を完成し
た。[Means and effects for solving the problem] The present inventors
When using phosphoric acid at a concentration of 60% in the preparation of 2-tert-butylhydroquinone by reacting hydroquinone with isobutene or tert-butyl alcohol in an organic solvent in the presence of phosphoric acid as a catalyst, The present invention was completed after discovering that the problems were solved.
８５チリン酸を使用する従来の２− ｔｅｒｔ −ブチ
ルヒドロキノンの製造方法においては、目的化合物の収
率が反応器の攪拌榮件に大きく影響され、攪拌が悪くな
ると反応選択性が急速に低下する。In the conventional method for producing 2-tert-butylhydroquinone using 85-thiphosphoric acid, the yield of the target compound is greatly affected by the stirring conditions of the reactor, and when the stirring becomes poor, the reaction selectivity decreases rapidly.
しかしながら本発明によれば、６０％リン酸の使用によ
り攪拌条件、例えば攪拌翼の回転数を４０゜ｒｐｍから
１７０Ｏｒｐｍ に変動させても高い選択性を維持し
て２− ｔｅｒｔ −ブチルヒドロキノンが得られる
。本発明においてリン酸濃度を６０係にしたのは、６０
チリン酸を使用したときには８５チリン酸を使用したと
きよりも攪拌状態の良し悪しに拘らず反応の選択性が高
い。すなわち８５チリン酸では攪拌が悪くなると目的化
合物の生成反応の選択性が大きく下がるが、６０ｃ４リ
ン酸では選択性の低下が極めて少ないからである。However, according to the present invention, by using 60% phosphoric acid, 2-tert-butylhydroquinone can be obtained while maintaining high selectivity even when the stirring conditions, for example, the rotation speed of the stirring blade is varied from 40° rpm to 170 rpm. . In the present invention, the phosphoric acid concentration is set to 60%.
When tyrinic acid is used, the selectivity of the reaction is higher than when 85 tyrinic acid is used, regardless of whether the stirring conditions are good or bad. That is, with 85 thiphosphoric acid, the selectivity of the reaction for producing the target compound decreases significantly when stirring becomes poor, but with 60c4 phosphoric acid, the decrease in selectivity is extremely small.
本発明の製造方法によれば、６０％リン酸を使用するの
で、２−ｔｅｒｔ −ブチルヒドロキノンか０２．５−
ジーｔａｒｔ−プチルヒＰロキノンへのアルキル化の進
行速度が抑制されて選択性が向上する。壕だ、本発明方
法においては、ヒドロキノン仕込濃度が比較的高くても
（２０％）、目的化合物が高収率で得られ、一方、反応
速度は８５多リン酸を使用する従来法の１〜１．５時間
と比較して５〜６時間に延長されたので、反応熱の発生
が温和であり反応の制御が容易である。一般に反応温度
が高い程２− ｔａｒｔ −ブチルヒドロキノンの生
成に有利であるとされているが、６０チリン酸を使用す
る本発明方法においては反応速度が適度に遅くなったの
で１０５〜１２５℃の高温で反応を行い目的化合物の収
率を高めろことができる。According to the production method of the present invention, since 60% phosphoric acid is used, 2-tert-butylhydroquinone or 02.5-
The rate of alkylation to di-tart-butylhyP-quinone is suppressed, improving selectivity. However, in the method of the present invention, the target compound can be obtained in high yield even if the concentration of hydroquinone is relatively high (20%), while the reaction rate is 1 to 1 in the conventional method using 85 polyphosphoric acid. Since the time is extended to 5 to 6 hours compared to 1.5 hours, the reaction heat is generated mildly and the reaction can be easily controlled. Generally, it is said that the higher the reaction temperature, the more advantageous it is to produce 2-tart-butylhydroquinone, but in the method of the present invention using 60-thiphosphoric acid, the reaction rate was moderately slow, so a high temperature of 105 to 125°C was used. The yield of the target compound can be increased by carrying out the reaction.
本発明においてはＮｊ（媒として使用するリン酸の濃度
が極めて重要である。リンｆ’！２濃度７０％のときに
２− ｔｅｒｔ −ブチルヒドロキノンの収率は上昇
するが６０優リン酸と比較して劣っている。また５０％
リン酸では６０チリン酷を使用したときよりも若干収率
が低下するだけであるが１反応速度が著しく低下して実
用的でない。従って本発明においては５５〜６５チリン
酸を使用することが必須的に重要である。以下の実施例
によって本発明を更に具体的に説明する。In the present invention, the concentration of phosphoric acid used as Nj (vehicle) is extremely important.When the phosphorus f'!2 concentration is 70%, the yield of 2-tert-butylhydroquinone increases, but compared to 60 euphosphoric acid and is inferior.Also 50%
When using phosphoric acid, the yield is only slightly lower than when using 60 liters of phosphoric acid, but the reaction rate is significantly lowered, making it impractical. Therefore, in the present invention, it is essential to use 55-65 tyrinic acid. The present invention will be explained in more detail with reference to the following examples.
実施例１
温度計は１１ガラスオートクレーブにヒドロキノン７３
５ｇ、トルエフ２５０ｒｒｔ１．６０多リン酸水溶ｉ２
６．４＆を入れ、反応系内を窒素置換した後、１０５℃
まで昇温する。攪拌翼回転数４００ｒｐｍで攪拌しなが
らイソブチ／４８．６Ｆを５時間かかつて添加する。イ
ソブテンの添加を終了した後、室温まで冷却し、反応液
が均一な相になるまでメタノールを加える。均一になっ
た液の一部を取り、炭酸水素ナトＩＪウムで中和後、反
応生成物をガスクロマトグラフィーで定量する、反応液
の組成はヒドロキノン６モルチ、２− ｔｅｒｔ −ブ
チルヒドロキノン７フ
ルヒドロキノン１２モルチであり、ヒドロキノンの転化
率は８９％、２−ｔｅｒｔ −ブチルヒドロキノンの
選択性は８７チであった。Example 1 Hydroquinone 73 in a thermometer 11 glass autoclave
5g, Toluev 250rrt1.60 polyphosphoric acid water soluble i2
6. After adding 4& and purging the reaction system with nitrogen, heat to 105°C.
Increase the temperature to. Isobutylene/48.6F was added once for 5 hours while stirring at a stirring blade rotation speed of 400 rpm. After the addition of isobutene is completed, the mixture is cooled to room temperature and methanol is added until the reaction mixture becomes a homogeneous phase. Take a portion of the homogeneous solution, neutralize it with sodium bicarbonate, and quantify the reaction product by gas chromatography. The composition of the reaction solution is 6 moles of hydroquinone, 7 moles of 2-tert-butylhydroquinone, and 7 moles of 2-tert-butylhydroquinone. The conversion rate of hydroquinone was 89%, and the selectivity for 2-tert-butylhydroquinone was 87 mol.
実施例２
反応時の攪拌翼回転数を１ ７ ０ ０ ｒｐｍにした
以外は実施例１と同様に操作した。反応液の組成はヒド
ロキノン９モル％、２ − ｔｅｒｔ − ’；’チル
ヒドロキノン７９モルチ、ジーｔｅｒｔ −ブチルヒド
ロキノン１２モルチであり、ヒドロキノン転化率は９１
ｑ６、２ − ｔｃｒｔ −ブチルヒドロキノンの選
択性は８７チであった、
比較例１
８５％リン酸を使用する以外は実施例１と同様に操作し
た。反応時間は１．５時間であり、反応液ノ組成はヒド
ロキノン６モルチ、２ーｔｅｒｔーブチルヒドロキノン
６４モルチ，ジーｔｅｒｔーブチルヒドロキノン２３モ
ルチでアリ、ヒドロキノン転化率は８７チ、２− ｔｅ
ｒｔ −ブチルヒドロキノンの選択性は７３％であった
。Example 2 The same procedure as in Example 1 was carried out except that the stirring blade rotation speed during the reaction was set to 1700 rpm. The composition of the reaction solution was 9 mol % of hydroquinone, 79 mol of 2-tert-';'-tylhydroquinone, and 12 mol of di-tert-butylhydroquinone, and the conversion rate of hydroquinone was 91 mol.
The selectivity for q6,2-tcrt-butylhydroquinone was 87%. Comparative Example 1 The same procedure as Example 1 was performed except that 85% phosphoric acid was used. The reaction time was 1.5 hours, and the composition of the reaction solution was 6 moles of hydroquinone, 64 moles of 2-tert-butylhydroquinone, and 23 moles of di-tert-butylhydroquinone, and the conversion rate of hydroquinone was 87 moles, 2-tert-butylhydroquinone.
Selectivity for rt-butylhydroquinone was 73%.
比敦例２
８５チリン酸を使用する以外は実施例２と同様に操作し
た。反応時間は１時間、反応液の組成はヒドロキノン６
モル％、２ − ｔｅｒｔ −ブチルヒドロキノン７０
モルチ、ジーｔｅｒｔ −プチルヒ１０キノン２４モル
チであり、ヒドロキノン転化率は９４％、２− ｔｅｒ
ｔ −ブチルヒドロキノンの選択性は７５％であった
。Specification Example 2 The procedure of Example 2 was repeated except that 85 tyrinic acid was used. The reaction time was 1 hour, and the composition of the reaction solution was hydroquinone 6.
Mol%, 2-tert-butylhydroquinone 70
10 quinone 24 molti, hydroquinone conversion rate is 94%, 2-tert
Selectivity for t-butylhydroquinone was 75%.
本発明によれば、ヒドロキノンの２− ｊｅｒｔ −グ
チル化による２ − ｔｅｒｔ −ブチルヒドロキノ
ンが高い選択性でかつ攪拌条件に影響を受けることなく
高収率で得られ、ヒドロキノンの仕込量を多くしても目
的化合物の生産性が低下せず、かつ反応を温和に行わせ
ることができるので製造装置の運転を安定化させること
ができる効果がある。According to the present invention, 2-tert-butylhydroquinone can be obtained by 2-jet-gtylation of hydroquinone with high selectivity and in a high yield without being affected by stirring conditions, and it can be obtained by increasing the amount of hydroquinone charged. However, since the productivity of the target compound does not decrease and the reaction can be carried out mildly, the operation of the production equipment can be stabilized.
Claims (1)
ソブテンまたはｔｅｒｔ−ブチルアルコールと反応させ
て２−ｔｅｒｔ−ブチルヒドロキノンを製造する方法に
おいて、５５〜６５％リン酸を使用することを特徴とす
る２−ｔｅｒｔ−ブチルヒドロキノンの改良された製造
方法。A method for producing 2-tert-butylhydroquinone by reacting hydroquinone with isobutene or tert-butyl alcohol in an organic solvent in the presence of phosphoric acid, characterized in that 55-65% phosphoric acid is used. An improved method for producing tert-butylhydroquinone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60220196A JPS6281338A (en) | 1985-10-04 | 1985-10-04 | Improvement of production of 2-tert-butylhydroquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60220196A JPS6281338A (en) | 1985-10-04 | 1985-10-04 | Improvement of production of 2-tert-butylhydroquinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6281338A true JPS6281338A (en) | 1987-04-14 |
Family
ID=16747391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60220196A Pending JPS6281338A (en) | 1985-10-04 | 1985-10-04 | Improvement of production of 2-tert-butylhydroquinone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6281338A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1312098C (en) * | 2005-09-23 | 2007-04-25 | 复旦大学 | Environment friendly 2-tertiary-butyl hydroquinone preparation method |
| CN103864579A (en) * | 2014-04-04 | 2014-06-18 | 广州泰邦食品科技有限公司 | Synthesis process for TBHQ (Tertiary Butyl Hydroquinone) crude product |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55115835A (en) * | 1979-02-28 | 1980-09-06 | Sumitomo Chem Co Ltd | Preparation of monoalkylresorcinol |
-
1985
- 1985-10-04 JP JP60220196A patent/JPS6281338A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55115835A (en) * | 1979-02-28 | 1980-09-06 | Sumitomo Chem Co Ltd | Preparation of monoalkylresorcinol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1312098C (en) * | 2005-09-23 | 2007-04-25 | 复旦大学 | Environment friendly 2-tertiary-butyl hydroquinone preparation method |
| CN103864579A (en) * | 2014-04-04 | 2014-06-18 | 广州泰邦食品科技有限公司 | Synthesis process for TBHQ (Tertiary Butyl Hydroquinone) crude product |
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