IL126197A - Preparation of 2, 3, 4, 5 - tetrafluorobenzene derivatives - Google Patents

Preparation of 2, 3, 4, 5 - tetrafluorobenzene derivatives

Info

Publication number: IL126197A
Authority: IL; Israel
Prior art keywords: formula; compound; temperature; pressure; trifluoro
Prior art date: 1997-09-16

Application number

IL12619798A

Other languages

English (en)

Other versions

IL126197A0 (en

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1997-09-16

Filing date

1998-09-14

Publication date

2001-05-20

1998-09-14 Application filed by Bayer Ag filed Critical Bayer Ag

1999-05-09 Publication of IL126197A0 publication Critical patent/IL126197A0/xx

2001-05-20 Publication of IL126197A publication Critical patent/IL126197A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 11
SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical class FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 25
238000000034 method Methods 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 14
239000012025 fluorinating agent Substances 0.000 claims abstract description 8
239000002904 solvent Substances 0.000 claims abstract description 8
239000003054 catalyst Substances 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
150000008422 chlorobenzenes Chemical class 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
239000003444 phase transfer catalyst Substances 0.000 claims description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 14
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 11
239000011698 potassium fluoride Substances 0.000 description 7
235000003270 potassium fluoride Nutrition 0.000 description 7
PVRJKVZQZVDIQH-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl PVRJKVZQZVDIQH-UHFFFAOYSA-N 0.000 description 6
ZWVOHERGWLDGFT-UHFFFAOYSA-N 1,2,3,4-tetrafluoro-5-(trifluoromethyl)benzene Chemical compound FC1=CC(C(F)(F)F)=C(F)C(F)=C1F ZWVOHERGWLDGFT-UHFFFAOYSA-N 0.000 description 5
OMFROCCDPJZNAL-UHFFFAOYSA-N 1-chloro-2,3,4-trifluoro-5-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(Cl)=CC(C(F)(F)F)=C1F OMFROCCDPJZNAL-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 5
238000003682 fluorination reaction Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 3
238000004508 fractional distillation Methods 0.000 description 3
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical class FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000007789 sealing Methods 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 1
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical class ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical class FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
OTCQGJASYOVVCB-UHFFFAOYSA-M 1-(2,2-dimethylpropyl)-n,n-dimethylpyridin-1-ium-4-amine;chloride Chemical compound [Cl-].CN(C)C1=CC=[N+](CC(C)(C)C)C=C1 OTCQGJASYOVVCB-UHFFFAOYSA-M 0.000 description 1
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
IDOFZVGHXAVYEZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzonitrile Chemical compound ClC1=CC(C#N)=C(Cl)C(Cl)=C1Cl IDOFZVGHXAVYEZ-UHFFFAOYSA-N 0.000 description 1
ZFZHCAIFWXGSNS-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzoyl fluoride Chemical compound FC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl ZFZHCAIFWXGSNS-UHFFFAOYSA-N 0.000 description 1
ZYEWNAMVVRPNJX-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl fluoride Chemical compound FC(=O)C1=CC(F)=C(F)C(F)=C1F ZYEWNAMVVRPNJX-UHFFFAOYSA-N 0.000 description 1
VWNMVYACOKCDLR-UHFFFAOYSA-N 3,5-dichloro-2,4-difluorobenzoyl fluoride Chemical compound FC(=O)C1=CC(Cl)=C(F)C(Cl)=C1F VWNMVYACOKCDLR-UHFFFAOYSA-N 0.000 description 1
HDPODBQAFOAFJY-UHFFFAOYSA-N 5-chloro-2,3,4-trifluorobenzoyl fluoride Chemical compound FC(=O)C1=CC(Cl)=C(F)C(F)=C1F HDPODBQAFOAFJY-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
150000003983 crown ethers Chemical group 0.000 description 1
230000006837 decompression Effects 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004714 phosphonium salts Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL12619798A 1997-09-16 1998-09-14 Preparation of 2, 3, 4, 5 - tetrafluorobenzene derivatives IL126197A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19740632A DE19740632A1 (de)	1997-09-16	1997-09-16	Verfahren zur Herstellung von 2,3,4,5-Tetrafluorbenzolderivaten

Publications (2)

Publication Number	Publication Date
IL126197A0 IL126197A0 (en)	1999-05-09
IL126197A true IL126197A (en)	2001-05-20

Family

ID=7842474

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12619798A IL126197A (en)	1997-09-16	1998-09-14	Preparation of 2, 3, 4, 5 - tetrafluorobenzene derivatives

Country Status (10)

Country	Link
US (1)	US6613948B1 (cs)
EP (1)	EP0908438B1 (cs)
JP (1)	JPH11246450A (cs)
KR (1)	KR19990029811A (cs)
CA (1)	CA2247231A1 (cs)
CZ (1)	CZ295298A3 (cs)
DE (2)	DE19740632A1 (cs)
ES (1)	ES2212184T3 (cs)
HU (1)	HUP9802105A3 (cs)
IL (1)	IL126197A (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102009049419B4 (de) *	2009-10-14	2012-03-08	Saltigo Gmbh	Verbessertes Verfahren zur Herstellung von 3-Chlor-4,5-difluorbenzotrifluorid
CN105061260A (zh) *	2015-08-25	2015-11-18	苏州飞翔新材料研究院有限公司	一种芳香类或吡啶类间位氟代化合物的制备方法
US10717690B2 (en) *	2017-06-22	2020-07-21	Zeon Corporation	Method of manufacturing octafluorocyclopentene
JP7381912B2 (ja) *	2021-10-13	2023-11-16	ダイキン工業株式会社	フッ素含有芳香族化合物の製造方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5530158A (en)	1984-06-04	1996-06-25	Bayer Aktiengesellschaft	2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives
DE3420796A1 (de) *	1984-06-04	1985-12-05	Bayer Ag, 5090 Leverkusen	2,4,5-trihalogen- bzw. 2,3,4,5-tetrahalogenbenzolderivate und verfahren zu ihrer herstellung
US4937396A (en) *	1988-11-28	1990-06-26	The Dow Chemical Company	Preparation of 3,4-difluorobenzotrifluoride
JPH0449263A (ja) *	1990-06-19	1992-02-18	Asahi Glass Co Ltd	２，３，４，５―テトラフルオロ安息香酸の新規製造法
DE4301247A1 (de)	1993-01-19	1994-07-21	Bayer Ag	Verfahren zur Herstellung mehrfach halogenierter Benzotrichloride und Benzoylchloride sowie neue Trihalogenbenzotrichloride und -benzoylchloride

1997
- 1997-09-16 DE DE19740632A patent/DE19740632A1/de not_active Withdrawn
1998
- 1998-09-03 EP EP98116713A patent/EP0908438B1/de not_active Expired - Lifetime
- 1998-09-03 ES ES98116713T patent/ES2212184T3/es not_active Expired - Lifetime
- 1998-09-03 DE DE59810251T patent/DE59810251D1/de not_active Expired - Lifetime
- 1998-09-11 CA CA002247231A patent/CA2247231A1/en not_active Abandoned
- 1998-09-14 IL IL12619798A patent/IL126197A/en not_active IP Right Cessation
- 1998-09-14 JP JP10276386A patent/JPH11246450A/ja not_active Withdrawn
- 1998-09-14 US US09/152,595 patent/US6613948B1/en not_active Expired - Fee Related
- 1998-09-15 KR KR1019980037993A patent/KR19990029811A/ko not_active Withdrawn
- 1998-09-16 HU HU9802105A patent/HUP9802105A3/hu unknown
- 1998-09-16 CZ CZ982952A patent/CZ295298A3/cs unknown

Also Published As

Publication number	Publication date
HUP9802105A3 (en)	2002-03-28
JPH11246450A (ja)	1999-09-14
HUP9802105A2 (hu)	1999-05-28
HU9802105D0 (en)	1998-11-30
EP0908438A2 (de)	1999-04-14
US6613948B1 (en)	2003-09-02
DE19740632A1 (de)	1999-03-18
KR19990029811A (ko)	1999-04-26
DE59810251D1 (de)	2004-01-08
IL126197A0 (en)	1999-05-09
EP0908438A3 (de)	2001-11-14
CA2247231A1 (en)	1999-03-16
ES2212184T3 (es)	2004-07-16
CZ295298A3 (cs)	1999-03-17
EP0908438B1 (de)	2003-11-26

Legal Events

Date	Code	Title
2001-10-31	FF	Patent granted
2001-11-25	KB	Patent renewed
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
DE68907783T2 (de)	1993-11-04	Verfahren zur herstellung von fluorierten aethern.
EP0180057B1 (en)	1989-08-09	Process for the preparation of halo aromatic compounds
KR920009790B1 (ko)	1992-10-22	1,1,1-클로로디플루오로에탄의 제조방법
US5045634A (en)	1991-09-03	Fluorination of haloolefins
US4966988A (en)	1990-10-30	Process for preparing acetonitrile 3-trifluoromethyl benzene
EP0372621B1 (en)	1994-08-17	Preparation of difluorobenzenes containing electron withdrawing substituents
US6613948B1 (en)	2003-09-02	Process for the preparation of 2,3,4,5-tetrafluorobenzene derivatives
GB2219292A (en)	1989-12-06	Process of preparing 1,2,2,2-tetrafluoroethyl-difluoromethyl ether
US4324930A (en)	1982-04-13	2,3-Dichloro-2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoropentane and process for its manufacture
US5440051A (en)	1995-08-08	Process for the α-chlorination of aryl ethers
US4769503A (en)	1988-09-06	Preparation of 3,4-dichlorobenzotrihalides
US5055624A (en)	1991-10-08	Synthesis of 1,1-dichloro-1,2,2,2-tetrafluoroethane
US7595426B2 (en)	2009-09-29	Method for the production of 1,3,5-trifluoro-2,4,6-trichlorobenzene from fluorobenzene derivatives
US4937396A (en)	1990-06-26	Preparation of 3,4-difluorobenzotrifluoride
US4377713A (en)	1983-03-22	Chemical process for preparing 3-phenoxybenzyl chloride
JP2865421B2 (ja)	1999-03-08	塩化３―トリフルオロメチルベンジルの製造方法
GB2194235A (en)	1988-03-02	Dichlorotrifluoromethyl toluenes
US5233104A (en)	1993-08-03	Process for trifluoromethylation of aromatic compounds
EP0289036A1 (en)	1988-11-02	Preparation of 3-chloro-4,5-difluorobenzotrifluoride
WO2001030728A1 (en)	2001-05-03	A method of making high purity 2,4-and 3,4- dichlorotoluene
EP0716644A1 (en)	1996-06-19	Production of difluoromethane
JPH0257530B2 (cs)	1990-12-05