WO2000012456A1 - Method of reducing ring chlorination in the manufacture of a trichloromethoxybenzene - Google Patents
Method of reducing ring chlorination in the manufacture of a trichloromethoxybenzene Download PDFInfo
- Publication number
- WO2000012456A1 WO2000012456A1 PCT/GB1999/002156 GB9902156W WO0012456A1 WO 2000012456 A1 WO2000012456 A1 WO 2000012456A1 GB 9902156 W GB9902156 W GB 9902156W WO 0012456 A1 WO0012456 A1 WO 0012456A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent
- mixture
- phenol
- anisole
- chlorine
- Prior art date
Links
- FXLOVSHXALFLKQ-UHFFFAOYSA-N Cc1ccc(C=O)cc1 Chemical compound Cc1ccc(C=O)cc1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
Definitions
- This invention relates to a method of making a trichloromethoxybenzene by reacting a methoxybenzene, such as anisole or p-chloroanisole, with chlorine
- trichloromethoxybenzene such as ⁇ , ⁇ , ⁇ -trichloromethoxybenzene (TCMB) or
- TCMCB ⁇ , ⁇ , ⁇ -trichloromethoxy-p-chlorobenzene
- U.S. Patent No. 5,773,668 discloses a process for making TCMB by
- methoxybenzene results in ring chlorination and dioxin formation, and that ring
- methoxybenzene that contains phenol is first purified to reduce the amount of phenol to below 20 ppm.
- step B (B) preparing a mixture of said methoxybenezene from step A and a source of chlorine free radicals in a solvent selected from the group consisting of benzotrifiuoride, orthochlorobenzotrifluoride, metachlorobenzotrifluoride,
- Preferably said mixture is heated to the reflux temperature of said solvent.
- said source of chlorine free radicals is chlorine gas.
- the solvent may be benzotrifiuoride and preferably is
- the methoxybenzene is anisole.
- the method includes the additional last step of reacting said
- the amount of said methoxybenzene is about 10 to about 60
- said process is performed in contact with metal and about 5
- the invention also provides A method of making ⁇ , ⁇ , ⁇
- the actinic radiation is ultraviolet light.
- said anisole and said chlorine gas are added separately to said solvent.
- a small amount of said solvent is first mixed with said anisole.
- the invention also provides A method of making ⁇ , ⁇ , ⁇ - trichloromethoxybenzene comprising
- the solvent may be benzotrifiuoride or parachlorobenzotrifluoride.
- Anisole can be made by reacting phenol with dimethyl sulfate or with a
- methoxybenzenes i.e., anisole, p-chloroanisole, and
- chloromethoxybenzene that contain at least 20 ppm of phenol.
- methoxybenzene contains at least 1000 ppm of phenol as those grades are less
- methoxybenzene feed is reduced to less than 20 ppm and preferably to less than
- the methoxybenzene can be passed through a bed of basic alumina, clay, or zeolite. Purification can also be accomplished by distillation.
- the methoxybenzenes are liquids which can be mixed with the BTF based
- methoxybenzene (based on total solvent plus methoxybenzene weight) should be
- concentration of methoxybenzene is about 30 to about 50 wt%.
- BTF based solvents that can be used in this invention
- PCBTF parachlorobenzotrifluoride
- dichlorobenzotrifluoride dichlorobenzotrifluoride
- PCBTF are preferred.
- the use of these solvents is essential to reducing ring chlorination.
- the source of chlorine free radicals can be, for example, elemental
- gaseous or liquefied chlorine or liquid sulfuryl chloride SO 2 CI 2
- gaseous chlorine is preferred as it results in fewer byproducts, it is inexpensive, and it
- radicals is needed (i.e., 3 moles Cl 2 per mole of the methoxybenzene), but a
- the methoxybenzene, solvent, and chlorine free radical source can be any organic radical source.
- Chlorine free radicals can be produced by exposing the source of chlorine
- actinic radiation examples include, for example, ultraviolet light, radio
- Free radical initiators can also be used to generate
- An ultraviolet wavelength of about 320 to about 340 nm is
- the light does not penetrate deeply into the mixture, the light
- the mixture should be stirred to expose all portions of the mixture to the
- reaction mixture is in contact with a metal, it may be desirable to add
- Suitable metal scavengers include N,N-dialkyl amides (sold as
- reaction can be performed as a batch, continuous, or semi- continuous process, but a continuous process is preferred as it is more efficient
- the TCMB product is useful as a chemical intermediate. For example, it
- TCMCB product is useful
- Example 1 was repeated with 326 g of benzotrifiuoride and 81 g of anisole
- Chlorine was added at a rate of 275 cc/min for approximately 3 hours. Chlorine flow was stopped when approximately 3.1
- Example 2 was repeated with 82 g of the anisole that contained less than 20
- Chlorine was added at a rate of 275 cc/min for
- Example 2 was repeated with 82 g of the anisole that contained less than 20
- Chlorine was added at a rate of 275 cc/min for
- dichloromethoxybenzene 47.5 wt% TCMB, and 25.2 wt% of various ring chlorinated methoxybenzenes.
- Example 5 Anisole containing 1200 ppm phenol, which was used in Example 1 , was
- Chlorine was added at a rate of 275 cc/min for approximately 3 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000567491A JP2002523481A (en) | 1998-08-31 | 1999-07-06 | A method for reducing ring chlorination in the production of trichloromethoxybenzene. |
EP99929578A EP1109771A1 (en) | 1998-08-31 | 1999-07-06 | Method of reducing ring chlorination in the manufacture of a trichloromethoxybenzene |
CA002341539A CA2341539A1 (en) | 1998-08-31 | 1999-07-06 | Method of reducing ring chlorination in the manufacture of a trichloromethoxybenzene |
AU46363/99A AU4636399A (en) | 1998-08-31 | 1999-07-06 | Method of reducing ring chlorination in the manufacture of trichloromethoxybenzene |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14379798A | 1998-08-31 | 1998-08-31 | |
US09/143,797 | 1998-08-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000012456A1 true WO2000012456A1 (en) | 2000-03-09 |
Family
ID=22505687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1999/002156 WO2000012456A1 (en) | 1998-08-31 | 1999-07-06 | Method of reducing ring chlorination in the manufacture of a trichloromethoxybenzene |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1109771A1 (en) |
JP (1) | JP2002523481A (en) |
AR (1) | AR020282A1 (en) |
AU (1) | AU4636399A (en) |
CA (1) | CA2341539A1 (en) |
WO (1) | WO2000012456A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105085202A (en) * | 2014-05-22 | 2015-11-25 | 刘世伟 | Synthetic method for trichloromethoxybenzene |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06340562A (en) * | 1993-06-02 | 1994-12-13 | Central Glass Co Ltd | Side chain chlorination of aromatic compound |
EP0860416A1 (en) * | 1997-02-24 | 1998-08-26 | Occidental Chemical Corporation | Method of making trichloromethoxybenzene |
-
1999
- 1999-07-06 EP EP99929578A patent/EP1109771A1/en not_active Withdrawn
- 1999-07-06 WO PCT/GB1999/002156 patent/WO2000012456A1/en not_active Application Discontinuation
- 1999-07-06 CA CA002341539A patent/CA2341539A1/en not_active Abandoned
- 1999-07-06 AU AU46363/99A patent/AU4636399A/en not_active Abandoned
- 1999-07-06 JP JP2000567491A patent/JP2002523481A/en active Pending
- 1999-08-27 AR ARP990104302A patent/AR020282A1/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06340562A (en) * | 1993-06-02 | 1994-12-13 | Central Glass Co Ltd | Side chain chlorination of aromatic compound |
EP0860416A1 (en) * | 1997-02-24 | 1998-08-26 | Occidental Chemical Corporation | Method of making trichloromethoxybenzene |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Section Ch Week 9509, Derwent World Patents Index; Class B05, AN 95-063792, XP002067102 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105085202A (en) * | 2014-05-22 | 2015-11-25 | 刘世伟 | Synthetic method for trichloromethoxybenzene |
Also Published As
Publication number | Publication date |
---|---|
AR020282A1 (en) | 2002-05-02 |
AU4636399A (en) | 2000-03-21 |
CA2341539A1 (en) | 2000-03-09 |
EP1109771A1 (en) | 2001-06-27 |
JP2002523481A (en) | 2002-07-30 |
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