JPH0615483B2 - Method for producing trifluoromethyltoluene - Google Patents
Method for producing trifluoromethyltolueneInfo
- Publication number
- JPH0615483B2 JPH0615483B2 JP62114714A JP11471487A JPH0615483B2 JP H0615483 B2 JPH0615483 B2 JP H0615483B2 JP 62114714 A JP62114714 A JP 62114714A JP 11471487 A JP11471487 A JP 11471487A JP H0615483 B2 JPH0615483 B2 JP H0615483B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyltoluene
- reaction
- trifluoromethyl
- producing
- purity
- 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
- DVFVNJHIVAPTMS-UHFFFAOYSA-N 1-methyl-2-(trifluoromethyl)benzene Chemical compound CC1=CC=CC=C1C(F)(F)F DVFVNJHIVAPTMS-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LRLRAYMYEXQKID-UHFFFAOYSA-N 1-methyl-4-(trifluoromethyl)benzene Chemical compound CC1=CC=C(C(F)(F)F)C=C1 LRLRAYMYEXQKID-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VJYXZJGDFJJDGF-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)benzene Chemical compound CC1=CC=CC(C(F)(F)F)=C1 VJYXZJGDFJJDGF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- -1 oxides Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BBXDMCQDLOCXRA-UHFFFAOYSA-N 1-(chloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CCl BBXDMCQDLOCXRA-UHFFFAOYSA-N 0.000 description 1
- XGASTRVQNVVYIZ-UHFFFAOYSA-N 1-(chloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CCl)=C1 XGASTRVQNVVYIZ-UHFFFAOYSA-N 0.000 description 1
- JIJFXGFHPXLJME-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)Cl JIJFXGFHPXLJME-UHFFFAOYSA-N 0.000 description 1
- LYADDKODNUCIMF-UHFFFAOYSA-N 1-(difluoromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)C1=CC=CC=C1C(F)(F)F LYADDKODNUCIMF-UHFFFAOYSA-N 0.000 description 1
- DPOABIVSXFUIJB-UHFFFAOYSA-N 1-(fluoromethyl)-4-(trifluoromethyl)benzene Chemical compound FCC1=CC=C(C(F)(F)F)C=C1 DPOABIVSXFUIJB-UHFFFAOYSA-N 0.000 description 1
- AVSVJSGDSPDFLH-UHFFFAOYSA-N 2,2,2-trifluoroethylbenzene Chemical class FC(F)(F)CC1=CC=CC=C1 AVSVJSGDSPDFLH-UHFFFAOYSA-N 0.000 description 1
- QARORTABMNEDCY-UHFFFAOYSA-N 2-chloro-1-(fluoromethyl)-3-(trifluoromethyl)benzene Chemical compound FCC1=CC=CC(C(F)(F)F)=C1Cl QARORTABMNEDCY-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 239000008096 xylene 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、医・農薬の中間体として有用なトリフルオロ
メチルトルエンの製造法に関する。TECHNICAL FIELD The present invention relates to a method for producing trifluoromethyltoluene useful as an intermediate for medicines and agricultural chemicals.
［従来技術とその問題点］ 従来、トリフルオロメチルトルエンの製造法としては以
下のものが知られている。[Prior Art and Problems Thereof] The following are known as conventional methods for producing trifluoromethyltoluene.
(1) (2) (3) (4) （１）の製造法は高価なトリフルオロメチルーベンジル
アルコールを出発物質としていること、（２）の製造法
で使用している弗素化剤としてのＳＦ４は大量には入手
困難であり高価かつ毒性が高く、高温・高圧下の条件が
必要であり、（３）の方法も高価なトリフルオロメチル
ヨードを使用しており工業的な方法でない、（４）の製
造法はトリフルオロメチルトルエンの３種類の異性体が
生成するために分離・精製が困難である等の問題点を有
していた。(1) (2) (3) (Four) The production method of (1) uses expensive trifluoromethyl-benzyl alcohol as a starting material, and SF 4 as a fluorinating agent used in the production method of (2) is difficult to obtain in a large amount and is expensive and toxic. High temperature, high temperature and high pressure conditions are required, and the method (3) uses expensive trifluoromethyl iodide and is not an industrial method. It has a problem that it is difficult to separate and purify because various kinds of isomers are generated.
［問題点を解決するための手段］ 本発明者らは、鋭意検討した結果、安価なキシレンを出
発物質として側鎖のメチル基を塩素化、弗素化すること
によりハロゲン化メチルベンゾトリフルオリド類（以下
ＨＭＢＴＦという）を生成し、水素化することにより高
収率で経済的なトリフルオロメチルトルエン類（以下Ｔ
ＦＴという）の製造法を見い出した。[Means for Solving the Problems] As a result of intensive studies, the inventors of the present invention conducted halogenated methylbenzotrifluorides () by chlorinating or fluorinating a side chain methyl group using inexpensive xylene as a starting material. By generating HMBTF and hydrogenating it, trifluoromethyltoluenes (hereinafter T
FT) manufacturing method.
ＨＭＢＴＦの水素化は一般に、ＨＭＢＴＦを最初にオー
トクレーブ中に加え、酸受容体、水素化触媒、水及び場
合によっては溶媒を加え撹拌しながら加熱し、そしてこ
れら反応混合物中に反応圧力下及び反応温度においても
はや水素が吸収されなくなるまで水素を通すことにより
下式のように実施される。The hydrogenation of HMBTF is generally carried out by first adding the HMBTF into the autoclave, adding the acid acceptor, hydrogenation catalyst, water and optionally solvent and heating with stirring, and then into these reaction mixtures under reaction pressure and reaction temperature. Is carried out by passing hydrogen until no more hydrogen is absorbed at.
水素化反応は中性または塩基性媒体中のいずれかで実施
できる。使用される酸受容体は本発明による方法では厳
密なものではない。適当な例えばアルカリ金属水酸化
物、炭酸塩または酢酸塩、およびアルカリ土類金属水酸
化物、酸化物、、炭酸塩または酢酸塩、たとえば水酸化
ナトリウム、炭酸ナトリウム、水酸化カリウム、炭酸カ
リウム、炭酸リチウム、酸化カルシウム、および酸化マ
グネシウムである。原則として、製造しようとする１モ
ルのＴＦＴ当たり少なくともＨＭＢＴＦの１個のトリフ
ルオロメチル基以外のハロゲン化メチル基に含まれるハ
ロゲンの数以上のモル数の酸受容体を使用すべきであ
る。 The hydrogenation reaction can be carried out in either neutral or basic media. The acid acceptor used is not critical in the method according to the invention. Suitable, such as alkali metal hydroxides, carbonates or acetates, and alkaline earth metal hydroxides, oxides, carbonates or acetates, such as sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, carbonic acid. Lithium, calcium oxide, and magnesium oxide. As a general rule, at least one mole of acid acceptor should be used per mole of TFT to be produced, at least as high as the number of halogens contained in the halogenated methyl group other than one trifluoromethyl group of HMBTF.
本発明に従う方法では、水素化は水の存在下に行われる
が、反応物に対して不活性である溶媒の存在下において
もできる。不活性溶媒は例えば炭素数が好適には１〜６
のアルコール類、例えばメタノール、エタノール、イソ
プロパノール、２−ブタノール等である。使用できる不
活性溶媒の他の例は、エーテル類、炭化水素類、酢酸な
どである。本発明による方法で使用できる溶媒を混合物
の形で用いることも可能である。ＨＭＢＴＦと溶媒の比
率は広く変化できる。In the process according to the invention, the hydrogenation is carried out in the presence of water, but it can also be carried out in the presence of a solvent which is inert towards the reactants. The inert solvent preferably has 1 to 6 carbon atoms, for example.
Alcohols such as methanol, ethanol, isopropanol, 2-butanol and the like. Other examples of inert solvents that can be used are ethers, hydrocarbons, acetic acid and the like. It is also possible to use the solvents which can be used in the process according to the invention in the form of mixtures. The ratio of HMBTF to solvent can vary widely.
本発明の水素化触媒としては通常使用される触媒、たと
えばパラジウム、ニッケル、白金等が好ましく特に好ま
しくは、パラジウム担持活性炭である。水素化触媒の濃
度は、ＨＭＢＴＦに対して１〜３０ｗｔ％が好ましい。
特に、好ましくは５〜２０ｗｔ％である。反応温度及び
反応圧力は、各々４０〜１５０℃、５〜５０kg／cm2が
好ましい。特に好ましくは、各々７０〜１２０℃、８〜
１５kg／cm2である。As the hydrogenation catalyst of the present invention, a catalyst usually used, for example, palladium, nickel, platinum or the like is preferable, and palladium-supported activated carbon is particularly preferable. The concentration of the hydrogenation catalyst is preferably 1 to 30 wt% with respect to HMBTF.
Particularly, it is preferably 5 to 20 wt%. The reaction temperature and reaction pressure are preferably 40 to 150 ° C. and 5 to 50 kg / cm 2 , respectively. Particularly preferably, each is 70 to 120 ° C., 8 to
It is 15 kg / cm 2 .
以下、実施例をもって本発明を明示するが、それらは本
発明を限定するものではない。Hereinafter, the present invention will be described with reference to examples, but they do not limit the present invention.
実施例１ ５００mlの攪拌機付きオートクレーブに、２−トリフル
オロメチル−ベンジルクロライド１００ｇ（０．５１４
モル）、酸受容体として１５ｗｔ％の水酸化ナトリウム
水溶液１６４ｇ、水素化触媒として５ｗｔ％パラジウム
カーボン５ｇを入れた。水素ガスでオートクレーブ内部
の空気を置換した後、反応温度７５℃、反応圧力８kg／
cm2で撹拌しながら３時間反応を行った。反応終了後、
ロ紙でパラジウムカーボンを除去しロ液を二層分離して
有機層を無水硫酸ナトリウムで乾燥し、純度９９．７％
の２−トリフルオロメチルトルエン７７．０ｇ（収率９
３．３％）を得た。Example 1 In a 500 ml autoclave equipped with a stirrer, 100 g (0.514) of 2-trifluoromethyl-benzyl chloride was added.
Mol), 164 g of a 15 wt% aqueous sodium hydroxide solution as an acid acceptor, and 5 g of 5 wt% palladium carbon as a hydrogenation catalyst. After replacing the air inside the autoclave with hydrogen gas, the reaction temperature was 75 ° C and the reaction pressure was 8 kg /
The reaction was carried out for 3 hours with stirring at cm 2 . After the reaction,
Palladium carbon was removed with paper, the liquid was separated into two layers, and the organic layer was dried over anhydrous sodium sulfate, and the purity was 99.7%.
2-Trifluoromethyltoluene 77.0 g (yield 9
3.3%) was obtained.
実施例２ 原料を３−トリフルオロメチル−ベンジルクロライドと
する以外は実施例１と同様に反応を行い純度９９．２％
の３−トリフルオロメチルトルエン７６．１ｇ（収率９
１．８％）を得た。Example 2 The reaction was performed in the same manner as in Example 1 except that the starting material was 3-trifluoromethyl-benzyl chloride, and the purity was 99.2%.
36.1 g of 3-trifluoromethyltoluene (yield 9
1.8%) was obtained.
実施例３ 原料を４−トリフルオロメチル−ベンジルフルオリド１
００ｇ（０．５６２モル）とし、１５ｗｔ％水酸化ナト
リウム水溶液を１８０ｇとする以外は実施例１と同様に
反応を行い純度９９．３％の４−トリフルオロメチルト
ルエン８３．７ｇ（収率９２．５％）を得た。Example 3 Starting material was 4-trifluoromethyl-benzyl fluoride 1
The reaction was carried out in the same manner as in Example 1 except that the amount of the solution was 00 g (0.562 mol) and the amount of the 15 wt% sodium hydroxide aqueous solution was 180 g, and 83.7 g of 4-trifluoromethyltoluene having a purity of 99.3% (yield 92. 5%) was obtained.
実施例４ 原料を２−トリフルオロメチル−ベンザルクロライド１
００ｇ（０．４３７モル）とし、１５ｗｔ％水酸化ナト
リウム水溶液を２８０ｇとする以外は実施例１と同様に
反応を行い純度９９．８％の２−トリフルオロメチルト
ルエン６４．５ｇ（収率９２．１％）を得た。Example 4 Starting material was 2-trifluoromethyl-benzal chloride 1
The reaction was performed in the same manner as in Example 1 except that the amount of the sodium hydroxide aqueous solution was 00 g (0.437 mol) and the 15 wt% sodium hydroxide aqueous solution was 280 g, and 64.5 g of 2-trifluoromethyltoluene having a purity of 99.8% (yield 92. 1%) was obtained.
実施例５ 原料を２−トリフルオロメチル−ベンザルフルオリド１
００ｇ（０．５１０モル）とし、１５ｗｔ％水酸化ナト
リウム水溶液を３２７ｇとする以外は実施例１と同様に
反応を行い純度９９．５％の２−トリフルオロメチルト
ルエン７７．６ｇ（収率９１．７％）を得た。Example 5 Starting material was 2-trifluoromethyl-benzal fluoride 1
00 g (0.510 mol) and 15 wt% sodium hydroxide aqueous solution was 327 g, except that the reaction was performed in the same manner as in Example 1 to obtain 77.6 g of 2-trifluoromethyltoluene having a purity of 99.5% (yield 91. 7%).
実施例６ 原料を２−モノクロロモノフルオロメチル−ベンゾトリ
フルオリド１００ｇ（０．４７１モル）とし、１５ｗｔ
％水酸化ナトリウム水溶液を３０１ｇとする以外は実施
例１と同様に反応を行い純度９９．３％の２−トリフル
オロメチルトルエン７０．０ｇ（収率９２．２％）を得
た。Example 6 The starting material was 2-monochloromonofluoromethyl-benzotrifluoride 100 g (0.471 mol), and 15 wt
The reaction was performed in the same manner as in Example 1 except that the amount of the sodium hydroxide aqueous solution was 301 g to obtain 70.0 g of 2-trifluoromethyltoluene having a purity of 99.3% (yield 92.2%).
実施例７ 原料を２−モノクロロジフルオロメチル−ベンゾトリフ
ルオリド１００ｇ（０．４３３モル）とし、２０ｗｔ％
水酸化ナトリウム水溶液を３１２ｇとする以外は実施例
１と同様に反応を行い純度９９．６％の４−トリフルオ
ロメチルトルエン６４．３ｇ（収率９２．３％）を得
た。Example 7 The starting material was 100 g (0.433 mol) of 2-monochlorodifluoromethyl-benzotrifluoride, and 20 wt%
The reaction was performed in the same manner as in Example 1 except that the amount of the aqueous sodium hydroxide solution was changed to 312 g, to obtain 64.3 g of 4-trifluoromethyltoluene having a purity of 99.6% (yield: 92.3%).
実施例８ 原料を４−ビス（トリフルオロメチル）ベンゼン１００
ｇ（０．４６７モル）とし、２０ｗｔ％水酸化ナトリウ
ム水溶液を２８０ｇとし、反応温度１１５〜１２１℃、
反応圧力１０kg／cm2、反応時間を１２時間とする以外
は実施例１と同様に反応を行い４−トリフルオロメチル
トルエン５５．８％、４−キシレン２３．１％、未反応
４−ビス（トリフルオロメチル）ベンゼン２０．５％の
有機物を得た。この混合有機物を常圧で精密蒸留を行
い、純度９７．５％の４−トリフルオロメチルトルエン
４５．８ｇ（収率５９．８％を得た。Example 8 4-bis (trifluoromethyl) benzene 100 was used as a raw material.
g (0.467 mol), a 20 wt% sodium hydroxide aqueous solution is 280 g, and a reaction temperature is 115 to 121 ° C.
The reaction was performed in the same manner as in Example 1 except that the reaction pressure was 10 kg / cm 2 , and the reaction time was 12 hours. 4-trifluoromethyltoluene 55.8%, 4-xylene 23.1%, unreacted 4-bis ( An organic substance containing 20.5% of trifluoromethyl) benzene was obtained. This mixed organic substance was subjected to precision distillation under atmospheric pressure to obtain 45.8 g of 4-trifluoromethyltoluene having a purity of 97.5% (yield 59.8%).
実施例９ ２０ｗｔ％水酸化ナトリウム水溶液の代わりに２０ｗｔ
％水酸化カリウム水溶液３７８．４ｇを使用し、５ｗｔ
％パラジウムカーボンを１０ｇ、反応時間を７時間とす
る以外は実施例８と同様に反応を行った。その結果、純
度９７．３％の４−トリフルオロメチルトルエン４７．
９ｇを得た。Example 9 20 wt% instead of 20 wt% sodium hydroxide aqueous solution
% Potassium hydroxide aqueous solution 378.4 g is used, and 5 wt
% Palladium carbon was used, and the reaction was performed in the same manner as in Example 8 except that the reaction time was 7 hours. As a result, 4-trifluoromethyltoluene 47. with a purity of 97.3%.
9 g was obtained.
実施例１０ ４−ビス（トリフルオロメチル）ベンゼンの代わりに３
−ビス（トリフルオロメチル）ベンゼンを使用する以外
は実施例９と同様に反応を行った。その結果、純度９
７．０％の３−トリフルオロメチルトルエン４６．４％
（収率６０．２％）を得た。Example 10 3 instead of 4-bis (trifluoromethyl) benzene
The reaction was performed in the same manner as in Example 9 except that -bis (trifluoromethyl) benzene was used. As a result, purity 9
7.0% 3-trifluoromethyltoluene 46.4%
(Yield 60.2%) was obtained.
［発明の効果］ 本発明はハロゲン化メチル基を有するベンゾトリフルオ
リドから容易に医・農薬の中間体として有用なトリフル
オロメチルトルエンを得ることができるものである。EFFECTS OF THE INVENTION The present invention makes it possible to easily obtain trifluoromethyltoluene, which is useful as an intermediate for medicines and agricultural chemicals, from benzotrifluoride having a halogenated methyl group.
Claims (1)
ゾトリフルオリドを水素ガス及び水素化触媒を用いてハ
ロゲン化メチル基を水素化してメチル基とするトリフル
オロメチルトルエンの製造法において、水の存在下酸受
容体としてアルカリ金属またはアルカリ土類金属の水酸
化物、炭酸塩または酢酸塩を使用することを特徴とする
トリフルオロメチルトルエンの製造法。1. The presence of water in a process for producing trifluoromethyltoluene in which benzotrifluoride substituted with a halogenated methyl group is hydrogenated to a methyl group by hydrogenating the halogenated methyl group using hydrogen gas and a hydrogenation catalyst. A method for producing trifluoromethyltoluene, which comprises using a hydroxide, carbonate or acetate of an alkali metal or an alkaline earth metal as a lower acid acceptor.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62114714A JPH0615483B2 (en) | 1987-05-13 | 1987-05-13 | Method for producing trifluoromethyltoluene |
| GB8810557A GB2205313B (en) | 1987-05-13 | 1988-05-05 | Preparation of trifluoromethyltoluene from halomethylbenzotrifluoride |
| DE3816253A DE3816253A1 (en) | 1987-05-13 | 1988-05-11 | METHOD FOR PRODUCING TRIFLUORMETHYLTOLUOL FROM HALOGENMETHYLBENZOTRIFLUORIDE |
| FR888806407A FR2615185B1 (en) | 1987-05-13 | 1988-05-11 | PROCESS FOR THE PREPARATION OF TRIFLUOROMETHYLTOLUENE FROM HALOMETHYLBENZOTRIFLUORIDE |
| US07/193,061 US4849557A (en) | 1987-05-13 | 1988-05-12 | Preparation of trifluoromethyltoluene from halomethylbenzotrifluoride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62114714A JPH0615483B2 (en) | 1987-05-13 | 1987-05-13 | Method for producing trifluoromethyltoluene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63280035A JPS63280035A (en) | 1988-11-17 |
| JPH0615483B2 true JPH0615483B2 (en) | 1994-03-02 |
Family
ID=14644780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62114714A Expired - Fee Related JPH0615483B2 (en) | 1987-05-13 | 1987-05-13 | Method for producing trifluoromethyltoluene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0615483B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4064727B2 (en) | 2002-05-31 | 2008-03-19 | セントラル硝子株式会社 | Method for producing 1,1,1-trifluoroacetone |
| JP4641839B2 (en) * | 2005-03-23 | 2011-03-02 | セントラル硝子株式会社 | Process for producing 4-methyl-3-trifluoromethylbenzoic acid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612845B2 (en) * | 1973-05-24 | 1981-03-25 |
-
1987
- 1987-05-13 JP JP62114714A patent/JPH0615483B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63280035A (en) | 1988-11-17 |
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