WO1997012854A1 - Process for the preparation of chloromethyl carbonyl chlorides - Google Patents
Process for the preparation of chloromethyl carbonyl chlorides Download PDFInfo
- Publication number
- WO1997012854A1 WO1997012854A1 PCT/EP1996/004137 EP9604137W WO9712854A1 WO 1997012854 A1 WO1997012854 A1 WO 1997012854A1 EP 9604137 W EP9604137 W EP 9604137W WO 9712854 A1 WO9712854 A1 WO 9712854A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- process according
- catalyst
- formula
- phosphine
- oxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical class ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 title description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 150000002596 lactones Chemical class 0.000 claims abstract description 10
- -1 aromatic lactone Chemical class 0.000 claims abstract description 8
- 239000012320 chlorinating reagent Substances 0.000 claims abstract description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- TXZFBHYDQGYOIT-UHFFFAOYSA-N 2-(chloromethyl)benzoyl chloride Chemical class ClCC1=CC=CC=C1C(Cl)=O TXZFBHYDQGYOIT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Chemical group 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims description 20
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- VDAVROFTSCFPSA-UHFFFAOYSA-N 3-chlorobenzene-1,2-dicarbonyl chloride Chemical group ClC(=O)C1=CC=CC(Cl)=C1C(Cl)=O VDAVROFTSCFPSA-UHFFFAOYSA-N 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 125000005506 phthalide group Chemical group 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ZFJMTDFOGDGPTF-UHFFFAOYSA-N phosphanium;chloride;hydrochloride Chemical compound P.Cl.Cl ZFJMTDFOGDGPTF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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 present invention relates to a process for the preparation of o-chloromethylbenzoyl chlorides of the general formula I
- R and n have the meanings stated for formula I, with a chlorinating agent in the presence of catalytic amounts of a phosphine and/or phosphine oxide.
- EP-583589 discloses the preparation of aromatic o-chloromethyl carbonyl chlorides using phosgene in the presence of an organic nitrogen compound as catalyst.
- EP- 13264 proposes the preparation of chlorocarbonyl chlorides from aliphatic lactones with phosgene in the presence of phosphine oxide.
- EP-583589 also discloses that aromatic o-chloromethyl carbonyl chlorides can be prepared from benzocondensated lactones with phosgene with the concomittant introduction of up to 100 mol % of hydrogen chloride, based on the lactone, or of such compounds which form hydrogen chloride with phosgene, in the presence of an organic nitrogen compound as catalyst.
- EP-413264 also discloses that aliphatic chlorocarbonyl chlorides can be prepared by reacting the corresponding aliphatic lactones with phosgene in the presence of a phosphine oxide as catalyst with the additional use of hydrogen chloride.
- Another advantage is that the catalyst can be reused after being isolated from the reaction mixture.
- the process of this invention can be described as follows:
- the phthalide or lactone of formula II and the arylphosphine catalyst or alkylphosphine catalyst can be placed in a reaction vessel with an inert solvent, but preferably without solvent, and can be reacted with a chlorinating agent in the temperature range from 100 to 240°C, preferably from 100 to 200°C, particularly preferably from 140 to 200°C, and at a pressure of 0.1 to 50 bar, preferably of 1 to 5 bar, particularly preferably at normal pressure.
- the process can be carried out batchwise or continuously.
- the chlorinating agent is chloro, thionyi chioride, suifuryl chloride, phthaloyl chloride, PCI 5 , PCI 3 , phosphorus oxychloride or phosgene. Phosgene is particulariy preferred.
- Suitable catalysts are arylphosphines or alkylphosphines or corresponding phosphine oxides or mixtures thereof. It is possible, for example, to use trialkylphosphines or trialkyl- phosphine oxides, whose unbranched or branched alkyl radicals contain 1 to 12, preferably 4 to 8, carbon atoms. Suitable compounds of this kind are typically trihexylphosphine, tributylphosphine oxide, trioctylphosphine and but-2-yldioctylphosphine oxide. However, it is preferred to use arylphosphines or arylphosphine oxides.
- Triphenylphosphine or triphenyl ⁇ phosphine oxide is particularly preferred. These examples are non-limiting. As can be proved, phosphine dichloride, which must be regarded as the actual reactant of lactone ring opening, is continuously formed in situ during the reaction and is then reconverted into phosphine or phosphine oxide and enters the reaction cycle again.
- the catalyst is preferably used in an amount of 0.1 to 10 mol %, preferably of 0.5 to 5 mol %, based on the amount of the phthalide or lactone of formula II.
- the molar ratio of phosgene to the phthalide or lactone of formula II is from 0.8 : 1 to 10 : 1 , preferably from 1 :1 to 3 : 1, particularly preferably from 1 : 1 to 1.5 : 1. Slightly higher or lower or identical molar ratios correspondingly apply to the other above-mentioned chlorinating agents.
- Inert solvents are suitably those solvents which do not react with the starting compounds and the reaction products under the reaction conditions.
- Typical examples are high-boiling hydrocarbons such as toluene, xylene and cumene, aromatic chlorine compounds, typically chlorobenzene and dichlorobenzene as well as ethers, typically dioxane, and also nitriles such as benzonitrile and acetonitrile.
- a solvent or diluent is usually not required.
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- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the preparation of o-chloromethylbenzoyl chlorides of formula (I), wherein R is identical or different substituents selected from the group consisting of hydrogen, C1-C6alkyl and halogen, and n = 0 to 4, preferably 0, which process comprises carrying out the reaction of an aromatic lactone of formula (II), wherein R and n have the meanings stated for formula (I), with a chlorinating agent with or without solvent in the temperature range from 100 to 240 °C in the presence of 0.1 to 10 mol % of a phosphine and/or phosphine oxide, based on the amount of lactone.
Description
Process for the preparation of chloromethyl carbonyl chlorides
The present invention relates to a process for the preparation of o-chloromethylbenzoyl chlorides of the general formula I
wherein R is identical or different substituents selected from the group consisting of hydrogen, Cι-C6alkyl and halogen, and n = 0 to 4, preferably 0, by reacting a lactone of formula II
wherein R and n have the meanings stated for formula I, with a chlorinating agent in the presence of catalytic amounts of a phosphine and/or phosphine oxide.
Compounds of formula I are important intermediates for the preparation of pesticides.
The preparation of aromatic o-chloromethyl carbonyl chlorides using phosgene in the presence of an organic nitrogen compound as catalyst is disclosed in EP-583589. EP- 13264 proposes the preparation of chlorocarbonyl chlorides from aliphatic lactones with phosgene in the presence of phosphine oxide.
EP-583589 also discloses that aromatic o-chloromethyl carbonyl chlorides can be prepared from benzocondensated lactones with phosgene with the concomittant introduction of up to 100 mol % of hydrogen chloride, based on the lactone, or of such compounds which form
hydrogen chloride with phosgene, in the presence of an organic nitrogen compound as catalyst.
EP-413264 also discloses that aliphatic chlorocarbonyl chlorides can be prepared by reacting the corresponding aliphatic lactones with phosgene in the presence of a phosphine oxide as catalyst with the additional use of hydrogen chloride.
The disadvantages of this proposed process for a technical synthesis are the additional consumption of hydrogen chloride and the resulting undesirable stripping effects, corrosion damages and exhaust air pollution, as well as the low boiling points of the catalysts which, in particular at elevated reaction temperatures (>150°C), are highly volatile and can deposit on the condensers.
Accordingly, it is the object of this invention to avoid these disadvantages and to develop an environmentally safe method of obtaining aromatic o-chloromethylphenylalkanoyl chlorides and, in particular, o-chloromethylbenzoyl chlorides in high yields. An improved and cost-favourable process for the preparation of o-chloromethylbenzoyl chlorides has now been found which comprises carrying out the reaction of an aromatic lactone of formula II and, preferably, of phthalide (n = 0), with or without solvents, with a chlorinating agent in the temperature range from 80 to 240°C in the presence of a phosphine catalyst and/or phosphine oxide catalyst.
Another advantage is that the catalyst can be reused after being isolated from the reaction mixture.
The process of this invention can be described as follows:
The phthalide or lactone of formula II and the arylphosphine catalyst or alkylphosphine catalyst can be placed in a reaction vessel with an inert solvent, but preferably without solvent, and can be reacted with a chlorinating agent in the temperature range from 100 to 240°C, preferably from 100 to 200°C, particularly preferably from 140 to 200°C, and at a pressure of 0.1 to 50 bar, preferably of 1 to 5 bar, particularly preferably at normal pressure. The process can be carried out batchwise or continuously.
The o-chloromethylbenzoyl chlorides are obtained in high yield and high purity.
The chlorinating agent is chloro, thionyi chioride, suifuryl chloride, phthaloyl chloride, PCI5, PCI3, phosphorus oxychloride or phosgene. Phosgene is particulariy preferred.
Suitable catalysts are arylphosphines or alkylphosphines or corresponding phosphine oxides or mixtures thereof. It is possible, for example, to use trialkylphosphines or trialkyl- phosphine oxides, whose unbranched or branched alkyl radicals contain 1 to 12, preferably 4 to 8, carbon atoms. Suitable compounds of this kind are typically trihexylphosphine, tributylphosphine oxide, trioctylphosphine and but-2-yldioctylphosphine oxide. However, it is preferred to use arylphosphines or arylphosphine oxides. Triphenylphosphine or triphenyl¬ phosphine oxide is particularly preferred. These examples are non-limiting. As can be proved, phosphine dichloride, which must be regarded as the actual reactant of lactone ring opening, is continuously formed in situ during the reaction and is then reconverted into phosphine or phosphine oxide and enters the reaction cycle again. The catalyst is preferably used in an amount of 0.1 to 10 mol %, preferably of 0.5 to 5 mol %, based on the amount of the phthalide or lactone of formula II.
The molar ratio of phosgene to the phthalide or lactone of formula II is from 0.8 : 1 to 10 : 1 , preferably from 1 :1 to 3 : 1, particularly preferably from 1 : 1 to 1.5 : 1. Slightly higher or lower or identical molar ratios correspondingly apply to the other above-mentioned chlorinating agents.
Inert solvents are suitably those solvents which do not react with the starting compounds and the reaction products under the reaction conditions. Typical examples are high-boiling hydrocarbons such as toluene, xylene and cumene, aromatic chlorine compounds, typically
chlorobenzene and dichlorobenzene as well as ethers, typically dioxane, and also nitriles such as benzonitrile and acetonitrile.
Where phthalide (m.p. 73°C) or another low-melting lactone of formula II is used, a solvent or diluent is usually not required.
Working Examples
Example 1
268.2 g of phthalide (2 mol) are placed in a sulfonation flask together with 5 mol % or 26.23 g of triphenylphosphine oxide and the mixture is then fused at c. 70°C and heated, with stirring, to 170°C. Subsequently, 2.4 mol (232.8 g) of phosgene are introduced under normal pressure over 4 to 5 hours. The reaction mixture is degassed with nitrogen and cooled, giving, in a rotation evaporator at 0.1 mbar and 120 to 140°C, the desired o-chloro¬ methylbenzoyl chloride in a yield of more than 94% of crude product and having a purity of at least 98%. A mixture of phosphine and phosphine oxide remains in the residue which can be reused.
Claims
1. A process for the preparation of o-chloromethylbenzoyl chloride of formula
wherein R is identical or different substituents selected from the group consisting of hydrogen, d-C6alkyl and halogen, and n = 0 to 4, preferably 0, which comprises reacting an aromatic lactone of formula II
wherein R and n have the meanings stated for formula I, with a chlorinating agent with or without a solvent in the temperature range from 100 to 240°C in the presence of 0.1 to 10 mol % of a phosphine and/or phosphine oxide, based on the amount of lactone.
2. A process according to claim 1 , wherein the aromatic lactone is phthalide.
3. A process according to claim 1 , wherein the catalyst is arylphosphine or alkylphosphine and/or the corresponding phosphine oxides.
4. A process according to claim 3, wherein the catalyst is trialkylphosphine and/or triaryl- phosphine.
5. A process according to claim 4, wherein the catalyst is triarylphosphine.
6. A process according to claim 5, wherein the catalyst is triphenylphosphine.
7. A process according to claim 3, wherein the catalyst is trialkylphosphine oxide and/or triarylphosphine oxide.
8. A process according to claim 7, wherein the catalyst is triarylphosphine oxide.
9. A process according to claim 8, wherein the catalyst is triphenylphosphine oxide.
10. A process according to claim 1 , which comprises carrying out the reaction without solvent or diluent.
11. A process according to claim 1 , which comprises carrying out the reaction in the temperature range from 100-200°C.
12. A process according to claim 1 , wherein the chlorinating agent is chloro, phthaloyl chloride, thionyl chloride, sulfuryl chloride, phosphorus oxychloride, phosphorus penta- chloride, phosphorus trichloride or phosgene.
13. A process according to claim 12, which comprises carrying out the reaction with phosgene.
14. A process according to claim 1 , which comprises reusing the added catalyst which remains in the reaction mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU72123/96A AU7212396A (en) | 1995-10-03 | 1996-09-21 | Process for the preparation of chloromethyl carbonyl chlorides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH278795 | 1995-10-03 | ||
| CH2787/95 | 1995-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997012854A1 true WO1997012854A1 (en) | 1997-04-10 |
Family
ID=4241592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1996/004137 WO1997012854A1 (en) | 1995-10-03 | 1996-09-21 | Process for the preparation of chloromethyl carbonyl chlorides |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU7212396A (en) |
| TW (1) | TW337519B (en) |
| WO (1) | WO1997012854A1 (en) |
| ZA (1) | ZA968272B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042183A3 (en) * | 1999-12-06 | 2002-05-02 | Basf Ag | Method for producing o-chloromethyl benzenecarbonyl chlorides |
| WO2001042185A3 (en) * | 1999-12-07 | 2002-05-02 | Basf Ag | Method for producing o-chloromethyl benzoic acid chlorides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0413264A1 (en) * | 1989-08-17 | 1991-02-20 | BASF Aktiengesellschaft | Process for the preparation of chlorocarboxylic acid chlorides |
-
1996
- 1996-09-03 TW TW085110719A patent/TW337519B/en active
- 1996-09-21 AU AU72123/96A patent/AU7212396A/en not_active Abandoned
- 1996-09-21 WO PCT/EP1996/004137 patent/WO1997012854A1/en active Application Filing
- 1996-10-02 ZA ZA968272A patent/ZA968272B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0413264A1 (en) * | 1989-08-17 | 1991-02-20 | BASF Aktiengesellschaft | Process for the preparation of chlorocarboxylic acid chlorides |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042183A3 (en) * | 1999-12-06 | 2002-05-02 | Basf Ag | Method for producing o-chloromethyl benzenecarbonyl chlorides |
| JP2003516374A (en) * | 1999-12-06 | 2003-05-13 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing o-chloromethylbenzoyl chloride |
| US6734322B1 (en) | 1999-12-06 | 2004-05-11 | Basf Aktiengesellschaft | Method for producing o-chloromethyl benzenecarbonyl chlorides |
| WO2001042185A3 (en) * | 1999-12-07 | 2002-05-02 | Basf Ag | Method for producing o-chloromethyl benzoic acid chlorides |
| JP2003516375A (en) * | 1999-12-07 | 2003-05-13 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing o-chloromethylbenzoyl chloride |
| US7034181B1 (en) | 1999-12-07 | 2006-04-25 | Basf Aktiengesellschaft | Method for producing o-chloromethyl benzoic acid chlorides |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7212396A (en) | 1997-04-28 |
| ZA968272B (en) | 1997-04-03 |
| TW337519B (en) | 1998-08-01 |
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