US3290370A - Process for the preparation of metahalosulfonylbenzoyl halide - Google Patents
Process for the preparation of metahalosulfonylbenzoyl halide Download PDFInfo
- Publication number
- US3290370A US3290370A US283571A US28357163A US3290370A US 3290370 A US3290370 A US 3290370A US 283571 A US283571 A US 283571A US 28357163 A US28357163 A US 28357163A US 3290370 A US3290370 A US 3290370A
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- US
- United States
- Prior art keywords
- acid
- preparation
- halide
- reaction
- chlorine
- 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 - Lifetime
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- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000004820 halides Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 description 11
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic carboxylic acids Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HWJPHQNEWARZLH-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluoro-6,6-bis(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F HWJPHQNEWARZLH-UHFFFAOYSA-N 0.000 description 1
- XWEBTVZIZWEJOO-UHFFFAOYSA-N 3-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 XWEBTVZIZWEJOO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- FVIRGMIYFJWRGC-UHFFFAOYSA-N sulfurobromidic acid Chemical compound OS(Br)(=O)=O FVIRGMIYFJWRGC-UHFFFAOYSA-N 0.000 description 1
- MVDRXYIEGOGRAI-UHFFFAOYSA-N tribromomethylbenzene Chemical compound BrC(Br)(Br)C1=CC=CC=C1 MVDRXYIEGOGRAI-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
Definitions
- the present invention is concerned with a process for the preparation of m-halosulfonylbenzoyl halides. More specifically, the present invention relates to the reaction of benzotrihalide and a sulfonating agent.
- benzotrihalide is reacted with a sulphonating agent in the presence of heat.
- the reaction may be exemplified by the following equation:
- X is a halogen selected from the group consisting of chlorine and bromine. It is surprisingly found that no substantial excess of halosulfonic acid is required, and that the dibasic acid dihalide is obtained directly in good yield and under moderate conditions. This result is especially surprising in view of the well known deactivating effect of a trihalomethyl group toward electrophilic substitution on the aromatic ring.
- Illustrative examples of the benzotrihalide starting reagent include benzotrichloride and benzotribromide.
- the sulfonating agents which may be utilized to practice the present invention are chlorosulfonic acid and bromosulfonic acid.
- reaction temperatures will vary with the reactivity of the particular starting reactants. Such a temperature will generally be in the range of from about 50 degrees centigrade to about 200 degrees centigrade.
- the preferred temperature employed in the practice of the present invention is in the range of about 60 degrees centigrade to about 150 degrees centigrade.
- the reagents are generally utilized in substantially equimolar amounts, but may be varied if desired. Generally ice the molar ratio of halosulfonic acid to benzotrihalide is in the range of less than 1:1 to about 6:1 with the preferred range being about 2 moles of halosulfonic acid to about 1 mole of benzotrichloride.
- Pressures employed in effecting the processes of the present invention are conveniently about atmospheric but subor super-atmospheric pressures may be employed.
- the pressure can obviously be as low as the vapor pressure of the halosulfonic acid starting reactant at operating temperatures. Pressures as high as those obtained in autoclaves e.g. 1,000 atmospheres, can be employed.
- a solvent is not generally necessary but one can be used to moderate or facilitate the reaction.
- the solvents which may be used are sulfonation-resistant solvents such as chlorobenzenes, nitrobenzenes, nitroalkanes, chloroalkanes, and the like.
- Other solvents of high enough boiling point to maintain the required reaction temperature and which do not react with either of the selected starting reagents may be utilized.
- benzotrichloride is added to chlorosulfonic acid in the presence of heat until the evolution of hydrogen halide has been completed and the resulting mixture is then purified, which may be done conveniently by distillation or other suitable means.
- the reaction may be illustrated by the following equation:
- Example 1 for preparing m-chlorosulfonylbenzoylchloride from benzotrichloride 543 grams (4.65 moles) of chlorosulfonic acid were heated to a temperature of about 60 degrees centigrade in a flask equipped with mechanical stirrer, reflux condenser, thermometer and addition funnel, and 392 grams (2 moles) benzotrichloride were added dropwise to the warm chlorosulfonic acid with stirring. The addition was accompanied by evolution of hydrogen chloride gas, which continued for about two hours after the addition was completed. After the addition was complete the temperature of the reaction mixture was brought to about 130 degrees centigrade for about two hours, until little or no further evolution of hydrogen chloride wa observed.
- X is a substituent selected from the group consisting of chlorine and bromine comprising contacting a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine with a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine.
- a process for the preparation of a compound of the formula COX wherein X is a substituent selected from the group consisting of chlorine and bromine comprising contacting a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine with a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine in the presence of heat.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,290,370 PROCESS FOR THE PREPARATION OF META- HALOSULFONYLBENZOYL HALIDE Edward D. Weil, Lewiston, N.Y., and Robert J. Lisanke,
Sr., Pitman, N.J., assignors to Hooker Chemical Corggoraition, Niagara Falls, N.Y., a corporation of New or No Drawing. Filed May 27, 1963, Ser. No. 283,571 6 Claims. (Cl. 260-544) The present invention is concerned with a process for the preparation of m-halosulfonylbenzoyl halides. More specifically, the present invention relates to the reaction of benzotrihalide and a sulfonating agent.
It has been known that sulphonyl chlorides are formed by the action of chlorosulfonic acid on aromatic hydrocarbons and that the yields of sulphonyl chlorides obtained may be increased by increasing the chlorosulfonic acid used, as is disclosed in Berichte der deutschen Chemischen Gesellschaft, volume 42, page 1802.. Therefore, in the large scale manufacture of sulphonyl chlorides of aromatic hydrocarbons, chlorosulphonic acid is generally employed in a large excess, or to avoid this necessity, the sulphonylchlorides are prepared from the sulphonic acids by reaction with phosphorus chlorides.
It has also been known that sulphonyl chlorides of aromatic carboxylic acids are obtained by the action of chlorosulphonic acid in large excess upon aromatic carboxylic acids, as, for example, in the conversion of an aromatic carboxylic acid chloride into the sulphonylchloride of the aromatic carboxylic acid by means of a large excess (14 mols) of chlorosulphonic acid (J. Chem. Soc. (London), 1934).
These processes yield chlorosulfonyl aroyl acids. Further reaction with an acylating agent such as PCl S Cl and the like, is required to convert the product to chlorosulfonyl aroyl chloride. Ingeneral, therefore, these processes are multi-step, requiring the utilization of costly reagents and equipment.
In accordance with the present invention benzotrihalide is reacted with a sulphonating agent in the presence of heat. The reaction may be exemplified by the following equation:
' o ox heat xso n 2 SOzX wherein X is a halogen selected from the group consisting of chlorine and bromine. It is surprisingly found that no substantial excess of halosulfonic acid is required, and that the dibasic acid dihalide is obtained directly in good yield and under moderate conditions. This result is especially surprising in view of the well known deactivating effect of a trihalomethyl group toward electrophilic substitution on the aromatic ring. Illustrative examples of the benzotrihalide starting reagent include benzotrichloride and benzotribromide. Among the sulfonating agents which may be utilized to practice the present invention are chlorosulfonic acid and bromosulfonic acid.
The reaction is generally accomplished by heating and stirring mixtures of the reactants until the evolution of hydrogen halide ceases. Reaction temperatures will vary with the reactivity of the particular starting reactants. Such a temperature will generally be in the range of from about 50 degrees centigrade to about 200 degrees centigrade. The preferred temperature employed in the practice of the present invention is in the range of about 60 degrees centigrade to about 150 degrees centigrade.
The reagents are generally utilized in substantially equimolar amounts, but may be varied if desired. Generally ice the molar ratio of halosulfonic acid to benzotrihalide is in the range of less than 1:1 to about 6:1 with the preferred range being about 2 moles of halosulfonic acid to about 1 mole of benzotrichloride.
Pressures employed in effecting the processes of the present invention are conveniently about atmospheric but subor super-atmospheric pressures may be employed. The pressure can obviously be as low as the vapor pressure of the halosulfonic acid starting reactant at operating temperatures. Pressures as high as those obtained in autoclaves e.g. 1,000 atmospheres, can be employed.
A solvent is not generally necessary but one can be used to moderate or facilitate the reaction. Among the solvents which may be used are sulfonation-resistant solvents such as chlorobenzenes, nitrobenzenes, nitroalkanes, chloroalkanes, and the like. Other solvents of high enough boiling point to maintain the required reaction temperature and which do not react with either of the selected starting reagents may be utilized.
In a preferred embodiment benzotrichloride is added to chlorosulfonic acid in the presence of heat until the evolution of hydrogen halide has been completed and the resulting mixture is then purified, which may be done conveniently by distillation or other suitable means. The reaction may be illustrated by the following equation:
heat m 0180 11 S0201 21101 In order that those skilled in the art may better understand the present invention, the manner in which it may be practiced, the following specific examples are given.
Example 1.-Pr0cess for preparing m-chlorosulfonylbenzoylchloride from benzotrichloride 543 grams (4.65 moles) of chlorosulfonic acid were heated to a temperature of about 60 degrees centigrade in a flask equipped with mechanical stirrer, reflux condenser, thermometer and addition funnel, and 392 grams (2 moles) benzotrichloride were added dropwise to the warm chlorosulfonic acid with stirring. The addition was accompanied by evolution of hydrogen chloride gas, which continued for about two hours after the addition was completed. After the addition was complete the temperature of the reaction mixture was brought to about 130 degrees centigrade for about two hours, until little or no further evolution of hydrogen chloride wa observed. Distillation of the mixture results in about a percent yield of metachlorosulfonyl benzoyl chloride, of boiling point of 161-3 degrees centigrade at 9 mm. mercury. Approximately 60 parts of chlorosulfonic acid is recovered in the foreshot, along with a little HCl and S0 Example 2 Similar to Example 1, 196 grams benzotrichloride was added over a two hour period to 175 grams of chlorosulfonic acid at to 127 degrees centigrade with agitation. The temperature was maintained at 120 degrees centigrade for 2.5 hours and the product was distilled. 193 grams of rnetachloros-ulfonyl benzoyl chloride was obtained as identified by infrared analysis.
While there have been described various embodiments of the invention, the methods and elements described are not intended to be understood as limiting the scope of the invention, as it is realized that changes therewithin are possible, and it is further intended that each element recited in any of the following claims is to be understood as referring to all equivalent elements for accomplishing substantially the same results in substantially the same or equivalent manner, it being intended to cover the invention broadly in whatever form its principle may be utilized.
What is claimed is: 1. A process for the preparation of a compound of the formula COX SOzX
wherein X is a substituent selected from the group consisting of chlorine and bromine comprising contacting a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine with a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine.
2. A process in accordance with claim 1 wherein X is chlorine.
3. A process for the preparation of a compound of the formula COX wherein X is a substituent selected from the group consisting of chlorine and bromine comprising contacting a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine with a compound of the formula wherein X is a substituent selected from the group consisting of chlorine and bromine in the presence of heat.
4. A process in accordance with claim 3 wherein the substituent X is chlorine.
5. A process in accordance with claim 3 wherein the temperature employed is from about 60 degrees :centigrade References Cited by the Examiner UNITED STATES PATENTS 1,557,154- 11/1925 George 260544 2,273,974 2/ 1942 Meiser 260507 X 3,203,987 8/1965 Hoefle 260544 X Y LORRAINE A. WEINBERGER, Primary Examiner.
RICHARD K. JACKSON, Assistant Examiner.
Claims (1)
1. A PROCESS FOR THE PREPARATION OF A COMPOUND OF THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US283571A US3290370A (en) | 1963-05-27 | 1963-05-27 | Process for the preparation of metahalosulfonylbenzoyl halide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US283571A US3290370A (en) | 1963-05-27 | 1963-05-27 | Process for the preparation of metahalosulfonylbenzoyl halide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3290370A true US3290370A (en) | 1966-12-06 |
Family
ID=23086664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US283571A Expired - Lifetime US3290370A (en) | 1963-05-27 | 1963-05-27 | Process for the preparation of metahalosulfonylbenzoyl halide |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3290370A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110373A (en) * | 1977-10-03 | 1978-08-29 | Hooker Chemicals & Plastics Corp. | Process for the preparation of benzoyl halide and halosulfonylbenzoyl halide |
| FR2404617A1 (en) * | 1977-10-03 | 1979-04-27 | Hooker Chemicals Plastics Corp | PROCESS FOR PREPARATION OF BENZOYL HALOGENIDES AND HALOGENOSULFONYLBENZOYL HALOGENIDES |
| US4212819A (en) * | 1978-07-10 | 1980-07-15 | Hooker Chemicals & Plastics Corp. | Process for the preparation of benzoyl halide and halosulfonylbenzoyl halide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1557154A (en) * | 1924-07-22 | 1925-10-13 | Mathieson Alkali Works Inc | Manufacture of benzoyl chloride |
| US2273974A (en) * | 1938-09-17 | 1942-02-24 | Gen Aniline & Film Corp | Sulphonataing process |
| US3203987A (en) * | 1962-05-28 | 1965-08-31 | Parke Davis & Co | 4-halo-3-sulfamoylbenzamides and methods of preparing the same |
-
1963
- 1963-05-27 US US283571A patent/US3290370A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1557154A (en) * | 1924-07-22 | 1925-10-13 | Mathieson Alkali Works Inc | Manufacture of benzoyl chloride |
| US2273974A (en) * | 1938-09-17 | 1942-02-24 | Gen Aniline & Film Corp | Sulphonataing process |
| US3203987A (en) * | 1962-05-28 | 1965-08-31 | Parke Davis & Co | 4-halo-3-sulfamoylbenzamides and methods of preparing the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110373A (en) * | 1977-10-03 | 1978-08-29 | Hooker Chemicals & Plastics Corp. | Process for the preparation of benzoyl halide and halosulfonylbenzoyl halide |
| FR2404617A1 (en) * | 1977-10-03 | 1979-04-27 | Hooker Chemicals Plastics Corp | PROCESS FOR PREPARATION OF BENZOYL HALOGENIDES AND HALOGENOSULFONYLBENZOYL HALOGENIDES |
| US4212819A (en) * | 1978-07-10 | 1980-07-15 | Hooker Chemicals & Plastics Corp. | Process for the preparation of benzoyl halide and halosulfonylbenzoyl halide |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: OCCIDENTAL CHEMICAL CORPORATION Free format text: CHANGE OF NAME;ASSIGNOR:HOOKER CHEMICALS & PLASTICS CORP.;REEL/FRAME:004109/0487 Effective date: 19820330 |