WO2006058642A1 - Verfahren zum herstellen von 3-halophthalsäuredichloriden - Google Patents
Verfahren zum herstellen von 3-halophthalsäuredichloriden Download PDFInfo
- Publication number
- WO2006058642A1 WO2006058642A1 PCT/EP2005/012519 EP2005012519W WO2006058642A1 WO 2006058642 A1 WO2006058642 A1 WO 2006058642A1 EP 2005012519 W EP2005012519 W EP 2005012519W WO 2006058642 A1 WO2006058642 A1 WO 2006058642A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phosgene
- formula
- continuously
- metered
- dialkyl
- Prior art date
Links
- NHUCGMKXUOFJQA-UHFFFAOYSA-N Cc1c(C(Cl)=O)c(C(Cl)=O)ccc1 Chemical compound Cc1c(C(Cl)=O)c(C(Cl)=O)ccc1 NHUCGMKXUOFJQA-UHFFFAOYSA-N 0.000 description 1
- 0 Oc(cccc1C(O2)=O)c1*2=O Chemical compound Oc(cccc1C(O2)=O)c1*2=O 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
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Definitions
- the invention relates to a novel process for the preparation of 3-Halophthal Acidichloriden (3-halo-benzene-l ⁇ -dicarboxylic acid dichlorides) from the corresponding 3-Halophthal Acidanhydriden.
- phthalic acid dichloride can be prepared from phthalic anhydride by reaction with suitable chlorine introducing agents ("chlorinating agents").
- phthaloyl chloride is obtained by reacting phthalic anhydride with trichloromethane or carbon tetrachloride in the presence of zinc chloride (see US 2,051,096).
- this reaction requires very high temperatures; trichloromethane and tetrachloromethane are also very problematic reaction components for industrial purposes today.
- Phthalic acid dichloride can also be obtained by reacting phthalic anhydride with thionyl chloride in the presence of zinc chloride (see J. Am Chem Chem 1937. 59, 206-208). This reaction also requires very high temperatures. Yield and quality of the product are not quite satisfactory in this method.
- phthalic acid dichloride can also be obtained by reacting phthalic anhydride with phosphorus (V) chloride (phosphorus pentachloride) (compare Can J. Chem. 1970. 48, 3566-3571). Again, the yield of the desired product is very unsatisfactory.
- phthaloyl chloride Another possibility for preparing phthaloyl chloride is the reaction of phthalic anhydride with trichloromethyl isocyanide dichloride in the presence of iron (IH) chloride is known (see DE-A 20 36 171). However, Chlorcarbonylisocyaniddichlorid falls as by-product.
- continuous means that the respective reaction component (phosgene and / or N, N-dialkylformamide) is continuously metered into the reaction mixture uniformly over the entire reaction time.
- reaction component phosgene and / or N, N-dialkylformamide
- individual portions are preferably of equal size and individual periods of time preferably the same length.
- the present invention thus provides a process for the preparation of 3-halophthalic acid dichlorides of the formula (I)
- R 1 and R 2 are independently straight-chain or branched alkyl, and an inert diluent, at temperatures between 2O 0 C and 15O 0 C in the presence of,
- the desired product can be obtained by distillation in high yield and in very good quality.
- Hal is preferably fluorine, chlorine, bromine or iodine, particularly preferably chlorine, bromine or iodine.
- the phosgene used as a means of introducing chlorine is also known.
- R 1 and R 2 independently of one another preferably represent straight-chain or branched Ci-Cio-alkyl, more preferably C r C 6 alkyl.
- N, N-dialkylformamides of the formula (III) which may be mentioned are: N, N-dimethylformamide, N, N-diethylformamide, N, N-di-n-propylformamide, N, N- Dnsopropylformamide, N, N-di-n-butyl-formamide and N, N-diazobutyl-formamide.
- N, N-dialkyl-formamides are known organic synthesis chemistries or reagents.
- the process according to the invention is carried out in the presence of an inert diluent.
- Suitable diluents are, in particular: hydrocarbons, such as pentane, hexane, heptane, octane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, and halogenated hydrocarbons, such as dichloromethane, chloromethane, tetrachloromethane, chlorobenzene or dichlorobenzene. Toluene and chlorobenzene are particularly preferred as diluents.
- the inventive method can be carried out within a relatively wide temperature range Preferably, the reaction is carried out at temperatures between 40 0 C and 12O 0 C, preferably between 55 0 C and 100 0 C.
- the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally between 0.1 bar and 50 bar, preferably between 1 bar and 10 bar.
- 1 mol of 3-halophthalic anhydride of the formula (II) is generally employed between 1.2 mol and 2.5 mol, preferably between 1.4 mol and 2.2 mol of phosgene, and also between 0 , 01 mol and 0.20 mol, preferably between 0.02 and 0.10 mol of N, N-dialkyl-formamide of the formula (ITf).
- a 3-Halophthal- klareanhyd ⁇ d is initially charged in an inert diluent, and the mixture is heated to the reaction temperature
- the phosgene and the N, N-dialkylformamide of the formula (HI) are then either distributed continuously over the entire reaction time or distributed "semi-continuously", ie to periods of about the same length and, depending on the number of these periods, to approximately divided into equal portions, dosed in portions.
- both the phosgene and the N, N-dialkylformamide of the formula (HI) are metered in continuously.
- both the phosgene and the N, N-dialkylformamide of the formula (HI) are metered into several portions distributed "semi-continuously".
- the phosgene is continuously metered in, while the N 1 N-dialkylformamide of the formula (JS) is metered into several portions "semi-continuously".
- the phosgene is metered into several portions distributed "semi-continuously", while the N, N-dialkyl-formamide of the formula (JS) is metered in continuously
- a reaction time of from 5 to 15 hours (depending on the batch size) is particularly advantageous, wherein a metered addition of the N, N-dialkylformamide of the formula (III) takes place every 15 to 90 minutes and the phosgene is continuously or "semi- continuously "metered
- reaction mixture After the end of the addition of phosgene and N, N-dialkyl-formamide of the formula (UI), the reaction mixture is advantageously maintained for 1 to 2 hours at the indicated reaction temperature and then worked up by distillation under reduced pressure.
- reaction mixture is stirred for 1 hour at 7O 0 C again.
- Excess phosgene and diluent are removed under reduced pressure.
- the crude product obtained as residue is purified by distillation under reduced pressure.
- reaction mixture is stirred for 1 hour at 70 0 C.
- Excess phosgene and diluent are removed under reduced pressure.
- the crude product obtained as residue is purified by distillation under reduced pressure.
- reaction mixture is stirred for 1 hour at 70 0 C.
- Excess phosgene and diluent are removed under reduced pressure.
- the crude product obtained as residue is purified by distillation under reduced pressure.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007543735A JP2008521845A (ja) | 2004-12-04 | 2005-11-23 | 3−ハロフタル酸ジクロリドを調製する方法 |
EP05810884A EP1819658A1 (de) | 2004-12-04 | 2005-11-23 | Verfahren zum herstellen von 3-halophthalsäuredichloriden |
US11/792,113 US20080039663A1 (en) | 2004-12-04 | 2005-11-23 | Method For Producing 3-Halophthalic Acid Dichlorides |
BRPI0515752-8A BRPI0515752A (pt) | 2004-12-04 | 2005-11-23 | processo para a preparação de dicloretos do àcido 3-haloftálico |
IL183588A IL183588A0 (en) | 2004-12-04 | 2007-05-31 | Method for producing 3-halophthalic acid dichlorides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004058519A DE102004058519A1 (de) | 2004-12-04 | 2004-12-04 | Verfahren zum Herstellen von 3-Halophthalsäuredichloriden |
DE102004058519.9 | 2004-12-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006058642A1 true WO2006058642A1 (de) | 2006-06-08 |
Family
ID=36124024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/012519 WO2006058642A1 (de) | 2004-12-04 | 2005-11-23 | Verfahren zum herstellen von 3-halophthalsäuredichloriden |
Country Status (8)
Country | Link |
---|---|
US (1) | US20080039663A1 (de) |
EP (1) | EP1819658A1 (de) |
JP (1) | JP2008521845A (de) |
CN (1) | CN101068767A (de) |
BR (1) | BRPI0515752A (de) |
DE (1) | DE102004058519A1 (de) |
IL (1) | IL183588A0 (de) |
WO (1) | WO2006058642A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010013684A1 (ja) | 2008-07-29 | 2010-02-04 | イハラニッケイ化学工業株式会社 | フタル酸ジクロリド化合物の製造方法、これに用いられる触媒及びその調製方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5649288B2 (ja) * | 2008-07-29 | 2015-01-07 | イハラニッケイ化学工業株式会社 | フタル酸ジクロリド化合物の製造方法及びこの製造方法に用いられる触媒 |
JP5782331B2 (ja) * | 2010-12-10 | 2015-09-24 | イハラニッケイ化学工業株式会社 | イミドイルクロリド化合物の製造方法及びそれを用いた各種化合物の製造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3810940A (en) * | 1972-04-07 | 1974-05-14 | Union Carbide Corp | Process for producing acid chlorides |
WO2004022520A1 (de) * | 2002-08-16 | 2004-03-18 | Bayer Cropscience Ag | Verfahren zum herstellen von phthalsäuredichlorid |
EP1598331A1 (de) * | 2004-05-17 | 2005-11-23 | Lanxess Deutschland GmbH | Verfahren zur Herstellung von Phthalsäuredichlorid |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2051096A (en) * | 1933-11-29 | 1936-08-18 | Monsanto Chemicals | Manufacture of carboxylic acid chlorides |
DE2036171A1 (de) * | 1970-07-21 | 1972-01-27 |
-
2004
- 2004-12-04 DE DE102004058519A patent/DE102004058519A1/de not_active Withdrawn
-
2005
- 2005-11-23 BR BRPI0515752-8A patent/BRPI0515752A/pt not_active IP Right Cessation
- 2005-11-23 JP JP2007543735A patent/JP2008521845A/ja not_active Withdrawn
- 2005-11-23 CN CNA2005800410382A patent/CN101068767A/zh active Pending
- 2005-11-23 US US11/792,113 patent/US20080039663A1/en not_active Abandoned
- 2005-11-23 EP EP05810884A patent/EP1819658A1/de not_active Withdrawn
- 2005-11-23 WO PCT/EP2005/012519 patent/WO2006058642A1/de active Application Filing
-
2007
- 2007-05-31 IL IL183588A patent/IL183588A0/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3810940A (en) * | 1972-04-07 | 1974-05-14 | Union Carbide Corp | Process for producing acid chlorides |
WO2004022520A1 (de) * | 2002-08-16 | 2004-03-18 | Bayer Cropscience Ag | Verfahren zum herstellen von phthalsäuredichlorid |
EP1598331A1 (de) * | 2004-05-17 | 2005-11-23 | Lanxess Deutschland GmbH | Verfahren zur Herstellung von Phthalsäuredichlorid |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010013684A1 (ja) | 2008-07-29 | 2010-02-04 | イハラニッケイ化学工業株式会社 | フタル酸ジクロリド化合物の製造方法、これに用いられる触媒及びその調製方法 |
US8642805B2 (en) | 2008-07-29 | 2014-02-04 | Iharanikkei Chemical Industry Co., Ltd. | Method of producing phthaloyl dichloride compound, catalyst for use in the method, and method of forming the catalyst |
Also Published As
Publication number | Publication date |
---|---|
CN101068767A (zh) | 2007-11-07 |
JP2008521845A (ja) | 2008-06-26 |
EP1819658A1 (de) | 2007-08-22 |
US20080039663A1 (en) | 2008-02-14 |
IL183588A0 (en) | 2007-09-20 |
DE102004058519A1 (de) | 2006-06-14 |
BRPI0515752A (pt) | 2008-07-29 |
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