CN1861554A - Production tech, of 3,4,5 trifluorophenol - Google Patents

Production tech, of 3,4,5 trifluorophenol Download PDF

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CN1861554A
CN1861554A CN 200510049766 CN200510049766A CN1861554A CN 1861554 A CN1861554 A CN 1861554A CN 200510049766 CN200510049766 CN 200510049766 CN 200510049766 A CN200510049766 A CN 200510049766A CN 1861554 A CN1861554 A CN 1861554A
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trifluorophenol
trifluoroaniline
production process
reaction
halo
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CN100488930C (en
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何人宝
钟建新
王莺妹
章正秋
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Inner Mongolia Yongtai Chemical Co ltd
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YONGTAI CHEMICAL CO Ltd LINHAI
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Abstract

本发明提供了一种3，4，5－三氟苯酚的生产工艺。它以1－卤代－3，4，5－三氟苯为起始原料，并依次经以下步骤：(1)使1－卤代－3，4，5－三氟苯与氨水进行反应温度为100～200℃的高压反应，以亚铜盐、铜盐或铜氧化物为催化剂，合成3，4，5－三氟苯胺，(2)将3，4，5－三氟苯胺进行重氮化反应，(3)将“步骤(2)”产物水解生成3，4，5－三氟苯酚。采用本发明所提供的生产方法，原料易得，后处理简单，无需特别设备，产物收率可达到74％～77％，远高于以往的工艺所能得到的收率。The invention provides a production process of 3,4,5-trifluorophenol. It uses 1-halo-3,4,5-trifluorobenzene as the starting material, and undergoes the following steps in sequence: (1) reacting 1-halo-3,4,5-trifluorobenzene with ammonia water It is a high-pressure reaction at 100-200 °C, using cuprous salt, copper salt or copper oxide as a catalyst to synthesize 3,4,5-trifluoroaniline, (2) 3,4,5-trifluoroaniline is subjected to diazonium (3) hydrolyze the product of "step (2)" to generate 3,4,5-trifluorophenol. By adopting the production method provided by the invention, the raw materials are easy to obtain, the aftertreatment is simple, no special equipment is needed, and the product yield can reach 74%-77%, which is much higher than the yield obtained by the prior art.

Description

A kind of 3,4, the production technique of 5-trifluoromethyl phenol
Technical field
The present invention relates to chemical field, relate in particular to and produce 3,4, the method for 5-trifluoromethyl phenol.
Background technology
3,4, the 5-trifluoromethyl phenol is a kind of important chemical intermediate, is mainly used in preparation liquid crystal, medicine intermediate.Its English name: 3,4,5-Trifluoro phenol, molecular formula is: C 6H 3F 3Be for OCAS number: the 99627-05-1 structural formula is:
Figure A20051004976600041
At present, seen bibliographical information preparation 3,4,5-trifluoromethyl phenol technology is, adopt 3,4, the 5-trifluorobromobenzene makes Grignard reagent and generates 3 with the boric acid ester reaction again, 4,5-trifluorophenyl boric acid is then with hydroperoxidation preparation 3,4, the 5-trifluoromethyl phenol, this processing method need use a large amount of organic solvents during its synthetic production, and grignard reaction needs to react under anhydrous state, so there are a plurality of shortcomings in this technology, 1, a large amount of solvent aftertreatment difficulties of in suitability for industrialized production, using, 2, the Grignard reaction conditions harshness, 3, overall yield of reaction is low, its yield has only≤and 50%, the unit consumption height.
Summary of the invention
It is new 3,4 that technical problem to be solved by this invention provides that a kind of yield improves, the production technique of 5-trifluoromethyl phenol.For this reason, the present invention is by the following technical solutions: it is with 1-halo-3,4, and the 5-trifluoro-benzene is a starting raw material, and successively through following steps:
(1), make 1-halo-3,4,5-trifluoro-benzene and ammoniacal liquor carry out temperature of reaction to be 100～200 ℃ reaction under high pressure, to be catalyzer with cuprous salt, mantoquita or copper oxide, synthetic 3,4, the 5-trifluoromethyl aniline,
(2), with 3,4, the 5-trifluoromethyl aniline carries out diazotization reaction,
(3), " step (2) " product hydrolysis is generated 3,4, the 5-trifluoromethyl phenol.
In starting raw material, with 1-bromo-3,4, the 5-trifluoro-benzene is preferred.
In " step (1) ", the concentration of ammoniacal liquor is big more to add fast response more, generally serving as preferred greater than 20%, and with 28% for most preferably, 1-halo-3,4, the mol ratio of 5-trifluoro-benzene and ammoniacal liquor is preferably 1: 5～15mol, and better scope is 8～10mol.
The add-on of catalyzer is a 1-halo-3,4 in " step (1) ", 1%～5% of 5-trifluoro-benzene weight, and catalyzer is preferably cuprous salt or Red copper oxide.
In " step (1) ", reacting to 1-halo-3,4,5-trifluoro-benzene content reduces to＜and below 1%, reaction is finished.
In " step (1) ", when temperature surpassed 170 ℃, pressure increased the afterreaction excessive velocities and causes by product to increase, and from the angle of economy, serves as preferred with 150～160 ℃.
In " step (2) ", 3,4, the reactant of 5-trifluoromethyl aniline diazotization reaction is the vitriol oil, Sodium Nitrite, 3,4, the 5-trifluoromethyl aniline.3,4,5 trifluoromethyl anilines and sulfuric acid mol ratio be preferably 1: 4～and 8,3,4,5 trifluoromethyl anilines and Sodium Nitrite mol ratio be preferably 1: 0.9～and 1.2.In " step (2) ", add 98%H in the diazotization still 2SO 4, be warming up to 45～50 ℃, add 3,4, the 5-trifluoromethyl aniline rises to 60～70 ℃ of insulations, is incubated after 20～30 minutes, is cooled to-5 ℃, drips sodium nitrite in aqueous solution, drips and finishes, and drips water at≤10 ℃ in still, then≤10 ℃ of heat preservation for standby use.
In " step (3) ", in hydrolysis kettle, add the vitriol oil, copper sulfate, splash into " step (2) " product at 100～150 ℃, collect distillate simultaneously.3,4,5-trifluoromethyl aniline and sulfuric acid mol ratio be preferably 1: 1.3～and 1.6,3,4,5-trifluoromethyl aniline and copper sulfate mol ratio are preferably: 1: 0.4～1.2.When dripping " step (2) " product, can control its rate of addition according to practical situation, the temperature of reaction solution is remained in the setting range, to guarantee in reaction, constantly producing and collect distillate, so, can reduce the generation of by product and tar, significantly improve the yield of product.
For the product of " step (3) ", the oil reservoir of rectifying distillate is collected 103～105 ℃/80mmHg fraction, gets 3,4,5-trifluoromethyl phenol product.
Adopt production method provided by the present invention, raw material is easy to get, and aftertreatment is simple, need not special equipment, and product yield can reach 74%～77%, far above the getable yield of technology in the past.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Embodiment 1
With 1-bromo-3,4, the 5-trifluoro-benzene is a starting raw material, carries out following steps successively:
(1), add Red copper oxide 6kg in the 3000L autoclave, 1-bromo-3,4,5-trifluoro-benzene 600kg pumps into 28% ammoniacal liquor 2000L again.Airtight autoclave stirs down and is warming up to 150～160 ℃, and pressure 3.0MPa reacts sampling analysis behind the 8h, and 1-bromo-3,4,5-trifluoro-benzene content reduce to＜and 1%, reaction is finished.Be cooled to 50 ℃, material N 2Be pressed into crystallizing pan, stir and be cooled to 0 ℃, filter, obtain 3,4,5-trifluoromethyl aniline product, yield 95%, content＞99.5%.Reaction equation:
Figure A20051004976600071
(2), add 98%H in the 1000L diazotization still 2SO 4300kg is warming up to 45～50 ℃, adds 3,4 under this temperature in still, 5-trifluoromethyl aniline 75kg; Finish, rise to 65 ℃ of insulation 25min, be cooled to-5 ℃, drip and to be dissolved in the solution that 120kg water is made into, temperature-5～0 ℃ by the 36kg Sodium Nitrite; Drip and finish, in still, dripping water 450kg below 10 ℃, stand-by at＜10 ℃ of insulation 20min then.Reaction equation:
(3), in hydrolysis kettle, add water 75kg, add 98%H again 2SO 475kg, copper sulfate 100kg is warming up to 130 ℃ then, and, splashes into " step (2) " product at 125～135 ℃, and about 12h of dropping time collects distillate simultaneously, tells lower floor's oil reservoir from distillate.103～105 ℃/80mmHg fraction is collected in oil reservoir rectifying, gets 3,4,5-trifluoromethyl phenol product, yield 77%, content＞99.5%.Reaction equation:
Figure A20051004976600073
Embodiment 2
With 1-bromo-3,4, the 5-trifluoro-benzene is a starting raw material, carries out following steps successively:
(1), add cuprous sulfate 5g in the 3L autoclave, 1-bromo-3,4,5-trifluoro-benzene 600g pumps into 28% ammoniacal liquor 1800ml again.Airtight autoclave stirs down and is warming up to 150～160 ℃, and pressure 3.0MPa reacts sampling analysis behind the 8h, and 1-bromo-3,4,5-trifluoro-benzene content reduce to＜and 1%, reaction is finished.Be cooled to 50 ℃, material N 2Be pressed into crystallizing pan, stir and be cooled to 0 ℃, filter, obtain 3,4,5-trifluoromethyl aniline product, yield 94%, content＞99.5%.
(2), add 98%H in the 1000ml diazotization still 2SO 4300g is warming up to 45～50 ℃, adds 3,4 under this temperature in still, 5-trifluoromethyl aniline 75g; Finish, rise to 65 ℃ of insulation 30min, be cooled to-5 ℃, drip and to be dissolved in the solution that 115g water is made into, temperature-5～0 ℃ by the 35g Sodium Nitrite; Drip and finish, in still, dripping water 400g below 10 ℃, stand-by at＜10 ℃ of insulation 20min then.
(3), in hydrolysis kettle, add water 70g, add 98%H again 2SO 475g, copper sulfate 100g is warming up to 130 ℃ then, and, splashes into " step (2) " product at 125～135 ℃, and about 11h of dropping time collects distillate simultaneously, tells lower floor's oil reservoir from distillate.103～105 ℃/80mmHg fraction is collected in oil reservoir rectifying, gets 3,4,5-trifluoromethyl phenol product, yield 77.5%, content＞99.5%.
Embodiment 3～11
With 1-bromo-3,4, the 5-trifluoro-benzene is a starting raw material, and step and operation be with embodiment 2, each processing parameter and the results are shown in following cartogram.
Step (1)
Temperature (℃) Catalyzer and add-on Ammoniacal liquor add-on (mol) Reaction times (hour) Average yield
Embodiment 3 105～135 Cupric chloride 0.01～0.02 5 13 91.3％
Embodiment 4 155～165 Cuprous sulfate 0.02～0.04 10 8 95.8％
Embodiment 5 165～180 Cuprous chloride 0.04～0.05 15 6.5 90.9％
Embodiment 6 140～155 Red copper oxide 0.02～0.04 10 8.3 94.3％
Embodiment 7 155～165 Red copper oxide 0.04～0.05 8 7 95.5％
Embodiment 8 165～180 Cupric nitrate 0.01～0.02 5 9.5 92.0％
Embodiment 9 140～155 Copper sulfate 0.04～0.05 15 7.5 92.0％
Embodiment 10 155～165 Cupric oxide 0.01～0.02 5 10.2 92.8％
Embodiment 11 170～195 Red copper oxide 0.02～0.04 10 7 93.6％
Step (2) Step (3)
98% sulfuric acid add-on The Sodium Nitrite add-on 98% sulfuric acid add-on The copper sulfate add-on Temperature of reaction Yield
Embodiment 3 4.1 1.18 1.58 0.7 100～150℃ 73.5％
Embodiment 4 4.9 1.07 1.32 0.9 110～130℃ 74.0％
Embodiment 5 5.0 1.10 1.38 1.0 120～130℃ 75.2％
Embodiment 6 6 1.0 1.4 0.8 120～130℃ 77.1％
Embodiment 7 5.5 1.08 1.42 0.9 120～140℃ 77.7％
Embodiment 8 7 0.95 1.45 0.6 120～130℃ 76.9％
Embodiment 9 6.4 1.05 1.5 1.2 120～150℃ 76.5％
Embodiment 10 7 1.15 1.55 1.1 100～130℃ 75.3％
Embodiment 11 7.8 1.12 1.35 0.5 120～130℃ 75.9％
In the last table, the catalyzer add-on is every 1kg1-bromo-3,4,5-trifluoro-benzene, the add-on of catalyzer (kg); The concentration of ammoniacal liquor is 28%, and its add-on is per 1 mole of 1-bromo-3,4,5-trifluoro-benzene, the mole number that ammoniacal liquor adds; 98% sulfuric acid add-on, Sodium Nitrite add-on, copper sulfate add-on are per 1 mole of 1-bromo-3,4,5-trifluoro-benzene, the added separately mole number of mentioned reagent.
As can be seen from the above table, when temperature surpassed 170 ℃, pressure increased the afterreaction excessive velocities and causes by product to increase, and from the angle of economy, was the preferred of step (1) with 150～160 ℃.In step (2), trifluoromethyl aniline and vitriolic mol ratio are about 6, specifically be 5.5～7, the mol ratio of trifluoromethyl aniline and Sodium Nitrite is 0.95～1.05, trifluoromethyl aniline and vitriolic mol ratio are 1.4～1.45 in the step (3), the mol ratio of trifluoromethyl aniline and copper sulfate is 0.6～0.9, and hydrolysising reacting temperature is in the time of 120～130 ℃, and reaction process is more economical, yield is higher.
Embodiment 12-13
Embodiment 12 adopts 1-chloro-3,4, and the 5-trifluoro-benzene substitutes the 1-bromo-3,4 of the foregoing description, the 5-trifluoro-benzene, and embodiment 13 adopts 1-iodo-3,4, and the 5-trifluoro-benzene substitutes the 1-bromo-3,4 of the foregoing description, 5-trifluoro-benzene.
Embodiment 12 adopts the processing condition of embodiment 2, and 3,4,5-trifluoromethyl phenol yield is 57%, embodiment 13 also adopts step and the parameter of embodiment 2, and 3,4,5-trifluoromethyl phenol yield is 55%.

Claims (10)

1、一种3，4，5-三氟苯酚的生产工艺，其特征在于它以1-卤代-3，4，5-三氟苯为起始原料，并依次经以下步骤：1, a kind of 3,4, the production technology of 5-trifluorophenol, it is characterized in that it is starting raw material with 1-halo-3,4,5-trifluorobenzene, and successively through following steps: (1)、使1-卤代-3，4，5-三氟苯与氨水进行反应温度为100～200℃的高压反应，以亚铜盐、铜盐或铜氧化物为催化剂，合成3，4，5-三氟苯胺，(1), making 1-halogenated-3,4,5-trifluorobenzene and ammonia water carry out a high-pressure reaction at a reaction temperature of 100 to 200° C., using cuprous salts, copper salts or copper oxides as catalysts to synthesize 3, 4,5-Trifluoroaniline, (2)、将3，4，5-三氟苯胺进行重氮化反应，(2), 3,4,5-trifluoroaniline is carried out diazotization reaction, (3)、将“步骤(2)”产物水解生成3，4，5-三氟苯酚。(3) Hydrolyze the product of "step (2)" to generate 3,4,5-trifluorophenol. 2、如权利要求1所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(1)”中，氨水的浓度以大于20％为优选，1-卤代-3，4，5-三氟苯与氨水的摩尔比优选为1∶5～15mol。2. A production process of 3,4,5-trifluorophenol as claimed in claim 1, characterized in that in "step (1)", the concentration of ammonia water is preferably greater than 20%, and 1-halo- The molar ratio of 3,4,5-trifluorobenzene to ammonia water is preferably 1:5-15 mol. 3、如权利要求1所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(1)”中催化剂的加入量为1-卤代-3，4，5-三氟苯重量的1％～5％，催化剂优选为亚铜盐或氧化亚铜。3. A production process of 3,4,5-trifluorophenol as claimed in claim 1, characterized in that the amount of catalyst added in "step (1)" is 1-halo-3,4,5- 1% to 5% by weight of trifluorobenzene, the catalyst is preferably cuprous salt or cuprous oxide. 4、如权利要求1所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(1)”中，反应至1-卤代-3，4，5-三氟苯含量降至＜1％以下，反应完成。4. A production process of 3,4,5-trifluorophenol as claimed in claim 1, characterized in that in "step (1)", the reaction to 1-halo-3,4,5-trifluorophenol When the benzene content drops below <1%, the reaction is complete. 5、如权利要求1所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(1)”中，反应温度以150～160℃为优选。5. A production process of 3,4,5-trifluorophenol as claimed in claim 1, characterized in that in "step (1)", the reaction temperature is preferably 150-160°C. 6、如权利要求1所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(2)”中，3，4，5-三氟苯胺重氮化反应的反应物为浓硫酸、亚硝酸钠、3，4，5-三氟苯胺。3，4，5-三氟苯胺与硫酸摩尔比优选为：1∶4～8，3，4，5-三氟苯胺与亚硝酸钠摩尔比优选为1∶0.9～1.2。6. A production process of 3,4,5-trifluorophenol as claimed in claim 1, characterized in that in "step (2)", the reaction of 3,4,5-trifluoroaniline diazotization reaction The substances are concentrated sulfuric acid, sodium nitrite, 3,4,5-trifluoroaniline. The molar ratio of 3,4,5-trifluoroaniline to sulfuric acid is preferably 1:4-8, and the molar ratio of 3,4,5-trifluoroaniline to sodium nitrite is preferably 1:0.9-1.2. 7、如权利要求6所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(2)”中，重氮化釜中加入98％H2SO4，升温至45～50℃，加入3，4，5-三氟苯胺，升至60～70℃，保温20～30分钟后，降温至-5℃，滴加亚硝酸钠水溶液，滴毕，在≤10℃时向釜内滴加水，然后在≤10℃保温待用。7. A production process of 3,4,5-trifluorophenol as claimed in claim 6, characterized in that in "step (2)", 98% H 2 SO 4 is added to the diazotization kettle, and the temperature is raised to 45～50℃, add 3,4,5-trifluoroaniline, rise to 60～70℃, keep warm for 20～30 minutes, then cool down to -5℃, add sodium nitrite aqueous solution dropwise, dropwise, at ≤10℃ Add water dropwise to the kettle from time to time, and then keep it warm at ≤10°C for later use. 8、如权利要求1所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(3)”中，在水解釜中加入浓硫酸、硫酸铜，在100～150℃滴入“步骤(2)”产物，同时收集馏出液。8. A production process of 3,4,5-trifluorophenol as claimed in claim 1, characterized in that in "step (3)", concentrated sulfuric acid and copper sulfate are added to the hydrolysis kettle, and the temperature is 100-150 The product of "step (2)" was added dropwise at ℃, while the distillate was collected. 9、如权利要求8所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于“步骤(3)”中，3，4，5-三氟苯胺与硫酸摩尔比优选为1∶1.3～1.6，3，4，5-三氟苯胺与硫酸铜摩尔比优选为：1∶0.4～1.2。9. A production process of 3,4,5-trifluorophenol as claimed in claim 8, characterized in that in "step (3)", the molar ratio of 3,4,5-trifluoroaniline to sulfuric acid is preferably 1:1.3-1.6, the molar ratio of 3,4,5-trifluoroaniline to copper sulfate is preferably: 1:0.4-1.2. 10、如权利要求8所述的一种3，4，5-三氟苯酚的生产工艺，其特征在于精馏馏出液的油层，收集103～105℃/80mmHg馏份，得3，4，5-三氟苯酚产物。10. A production process of 3,4,5-trifluorophenol as claimed in claim 8, characterized in that the oil layer of the distillate is rectified, and the 103-105°C/80mmHg fraction is collected to obtain 3,4, 5-Trifluorophenol product.
CNB200510049766XA 2005-05-09 2005-05-09 Production technology of 3,4,5 trifluorophenol Expired - Lifetime CN100488930C (en)

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CN102108044A (en) * 2011-01-28 2011-06-29 常州吉恩化工有限公司 Purification method of liquid crystal intermediate 3,4,5-trifluoro phenol
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CN102887817A (en) * 2012-09-11 2013-01-23 浙江永太科技股份有限公司 Novel method for synthesizing 2,3,4,5,6-pentafluorophenol
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CN101445431B (en) * 2008-12-30 2012-02-29 衢州康鹏化学有限公司 Method for preparing fluorophenol
CN102086147B (en) * 2009-12-04 2014-04-09 联化科技股份有限公司 Preparation method of substituted phenol
CN102086147A (en) * 2009-12-04 2011-06-08 联化科技股份有限公司 Preparation method of substituted phenol
CN102108044B (en) * 2011-01-28 2013-09-25 常州吉恩化工有限公司 Purification method of liquid crystal intermediate 3,4,5-trifluoro phenol
CN102108044A (en) * 2011-01-28 2011-06-29 常州吉恩化工有限公司 Purification method of liquid crystal intermediate 3,4,5-trifluoro phenol
CN102260143A (en) * 2011-05-18 2011-11-30 郓城县世炬化工有限公司 Production process for 3-fluorophenol
CN102503779A (en) * 2011-11-18 2012-06-20 江苏联化科技有限公司 Preparation method of 3, 4, 5-trifluoromethylphenol
CN102887817A (en) * 2012-09-11 2013-01-23 浙江永太科技股份有限公司 Novel method for synthesizing 2,3,4,5,6-pentafluorophenol
CN102887817B (en) * 2012-09-11 2015-04-01 浙江永太科技股份有限公司 Novel method for synthesizing 2,3,4,5,6-pentafluorophenol
CN103497111A (en) * 2013-09-09 2014-01-08 江苏德峰药业有限公司 Synthetic method for 2, 3, 4-trifluoroaniline
CN103497111B (en) * 2013-09-09 2015-10-21 江苏德峰药业有限公司 A kind of synthetic method of 2,3,4-trifluoromethyl aniline
CN106946659A (en) * 2017-03-03 2017-07-14 上海康鹏科技有限公司 A kind of preparation method of Pentafluorophenol
CN106946659B (en) * 2017-03-03 2020-08-25 上海康鹏科技股份有限公司 Preparation method of pentafluorophenol
CN109456150A (en) * 2018-10-25 2019-03-12 浙江林江化工股份有限公司 A kind of synthetic method of 3,4,5-Trifluoro phenol

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