US2270257A - Preparation of dixanthogens - Google Patents
Preparation of dixanthogens Download PDFInfo
- Publication number
- US2270257A US2270257A US370684A US37068440A US2270257A US 2270257 A US2270257 A US 2270257A US 370684 A US370684 A US 370684A US 37068440 A US37068440 A US 37068440A US 2270257 A US2270257 A US 2270257A
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- US
- United States
- Prior art keywords
- xanthate
- temperature
- alkali metal
- sodium
- dixanthogen
- 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.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
Definitions
- This invention relates to the preparation of dixanthogens, and has as its principal object the oxidation of an alkali metal xanthate with alkali metal hypochlorite under such conditions that good yields of a dixanthogen are obtained.
- an aqueous solution of 29.8 gm. of sodium hypochlorite was placed in a dropping funnel and slowly added to an aqueous solution of 64.7 gm. of sodium isopropyl xanthate, the temperature of the reaction mixture being maintained between 15 and 20 C.
- the light yellow crystalline product was separated from the reaction mixture and dried.
- a 63% yield of pure diisopropyl dixanthogen was obtained.
- the yields were decreased by more than 10%. Materially decreased yields were also obtained by performing the oxidation in the temperature range between 35 and 40 C.
- Any alkali metal xanthate such as sodium ethyl xanthate, sodium n-propyl xanthate, sodium sec.-butyl xanthate, sodium act.-amyl xanthate, potassium cyclohexyl xanthate, potassium benzyl xanthate, etc. may be oxidized to the corresponding dixanthogen by the method of this invention.
- Any alkali metal hypochlorite may be employed, although sodium or potassium hypochlorite will ordinarily be selected for economic reasons.
- the temperature may be maintained within the desired range by any desired method of cooling. Since the oxidation is performed in aqueous solution, it is convenient to cool the reaction mixture to 15-25 C. by merely adding ice, and to maintain the temperature within this range by adding more ice as needed during the course of the reaction.
- the method of oxidizing an alkali metal xanthate to a dixanthogen which comprises adding an alkali metal hypochlorite to an aqueous solution of the xanthate and maintaining the temperature within the approximate range of from 15 to 25 C. throughout the oxidation.
- the method of oxidizing a sodium xanthate to a dixanthogen which comprises adding sodium hypochlorite to an aqueous solution of the xanthate and maintaining the temperature within the approximate range of from 15 to 25 0. throughout the oxidation.
- the method of oxidizing sodium isopropyl xanthate to diisopropyl dixanthogen which comprises adding sodium hypochlorite to an aqueous solution of the xanthate and maintaining the temperature within the approximate range of from 15 to 25 C. throughout the oxidation.
- the method of oxidizing an alkali metal xanthate to a dixanthogen which comprises adding an alkali metal hypochlorite to an aqueous solution of the xanthate and maintaining the temperature at about 20 C. throughout the oxidation.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 20, 1942 PREPARATION OF DIXANTHOGENS George L. Browning, Jr., Akron, Ohio, assignor to The B. F. Goodrich Company, New York, N. Y., a corporation of New York No Drawing. Application December 18, 1940, Serial No. 370,684
4 Claims.
This invention relates to the preparation of dixanthogens, and has as its principal object the oxidation of an alkali metal xanthate with alkali metal hypochlorite under such conditions that good yields of a dixanthogen are obtained.
When alkali metal xanthates are oxidized to dixanthogens by means of an alkali metal hypochlorite and no attempt is made to remove the heat generated by the reaction, rather low yields of product are obtained. Even when an efficient cooling system is employed and the temperature is kept down to about C., no improvement in yield is observed. I have found that contrary to expectations, when the temperature is maintained in the approximate range of from -25 0., and preferably about C., higher yields of dixanthogen are obtained.
In one experiment, an aqueous solution of 29.8 gm. of sodium hypochlorite was placed in a dropping funnel and slowly added to an aqueous solution of 64.7 gm. of sodium isopropyl xanthate, the temperature of the reaction mixture being maintained between 15 and 20 C. The light yellow crystalline product was separated from the reaction mixture and dried. A 63% yield of pure diisopropyl dixanthogen was obtained. When the same oxidation was performed at a temperature below 10 C., the yields were decreased by more than 10%. Materially decreased yields were also obtained by performing the oxidation in the temperature range between 35 and 40 C.
Any alkali metal xanthate such as sodium ethyl xanthate, sodium n-propyl xanthate, sodium sec.-butyl xanthate, sodium act.-amyl xanthate, potassium cyclohexyl xanthate, potassium benzyl xanthate, etc. may be oxidized to the corresponding dixanthogen by the method of this invention. Any alkali metal hypochlorite may be employed, although sodium or potassium hypochlorite will ordinarily be selected for economic reasons.
The temperature may be maintained within the desired range by any desired method of cooling. Since the oxidation is performed in aqueous solution, it is convenient to cool the reaction mixture to 15-25 C. by merely adding ice, and to maintain the temperature within this range by adding more ice as needed during the course of the reaction.
Various modifications of the above procedure which will be apparent to those skilled in the art are within the spirit and scope of the invention as defined in the appended claims.
I claim:
1. The method of oxidizing an alkali metal xanthate to a dixanthogen which comprises adding an alkali metal hypochlorite to an aqueous solution of the xanthate and maintaining the temperature within the approximate range of from 15 to 25 C. throughout the oxidation.
2. The method of oxidizing a sodium xanthate to a dixanthogen which comprises adding sodium hypochlorite to an aqueous solution of the xanthate and maintaining the temperature within the approximate range of from 15 to 25 0. throughout the oxidation.
3. The method of oxidizing sodium isopropyl xanthate to diisopropyl dixanthogen which comprises adding sodium hypochlorite to an aqueous solution of the xanthate and maintaining the temperature within the approximate range of from 15 to 25 C. throughout the oxidation.
4. The method of oxidizing an alkali metal xanthate to a dixanthogen which comprises adding an alkali metal hypochlorite to an aqueous solution of the xanthate and maintaining the temperature at about 20 C. throughout the oxidation.
GEORGE L. BROWNING, JR.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US370684A US2270257A (en) | 1940-12-18 | 1940-12-18 | Preparation of dixanthogens |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US370684A US2270257A (en) | 1940-12-18 | 1940-12-18 | Preparation of dixanthogens |
Publications (1)
Publication Number | Publication Date |
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US2270257A true US2270257A (en) | 1942-01-20 |
Family
ID=23460719
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US370684A Expired - Lifetime US2270257A (en) | 1940-12-18 | 1940-12-18 | Preparation of dixanthogens |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2676974A (en) * | 1951-01-02 | 1954-04-27 | Phillips Petroleum Co | Production of disulfides |
US2676973A (en) * | 1951-01-02 | 1954-04-27 | Phillips Petroleum Co | Production of disulfides |
EP0053319A1 (en) * | 1980-11-28 | 1982-06-09 | Bayer Ag | Process for preparation of xanthogen disulphides and their use as molecular-weight regulators in the polymerisation of chloroprene |
RU2713402C1 (en) * | 2019-11-07 | 2020-02-05 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Method of producing diisopropylxanthogen disulphide |
-
1940
- 1940-12-18 US US370684A patent/US2270257A/en not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2676974A (en) * | 1951-01-02 | 1954-04-27 | Phillips Petroleum Co | Production of disulfides |
US2676973A (en) * | 1951-01-02 | 1954-04-27 | Phillips Petroleum Co | Production of disulfides |
EP0053319A1 (en) * | 1980-11-28 | 1982-06-09 | Bayer Ag | Process for preparation of xanthogen disulphides and their use as molecular-weight regulators in the polymerisation of chloroprene |
RU2713402C1 (en) * | 2019-11-07 | 2020-02-05 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Method of producing diisopropylxanthogen disulphide |
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