CA1297888C - Process for preparing bis (ethoxythiocarbonyl)sulfide - Google Patents
Process for preparing bis (ethoxythiocarbonyl)sulfideInfo
- Publication number
- CA1297888C CA1297888C CA000554442A CA554442A CA1297888C CA 1297888 C CA1297888 C CA 1297888C CA 000554442 A CA000554442 A CA 000554442A CA 554442 A CA554442 A CA 554442A CA 1297888 C CA1297888 C CA 1297888C
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- sodium
- xanthate
- sulfide
- ethanol
- 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
Links
- ALGQDBJUFSYDLA-UHFFFAOYSA-N o-ethyl ethoxycarbothioylsulfanylmethanethioate Chemical compound CCOC(=S)SC(=S)OCC ALGQDBJUFSYDLA-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims abstract description 16
- RZFBEFUNINJXRQ-UHFFFAOYSA-M sodium ethyl xanthate Chemical compound [Na+].CCOC([S-])=S RZFBEFUNINJXRQ-UHFFFAOYSA-M 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- MYXNWWDJRWCURH-UHFFFAOYSA-N ethoxymethanethioic s-acid Chemical compound CCOC(S)=O MYXNWWDJRWCURH-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- -1 ETHOXYTHIO-CARBONYL Chemical class 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94353686A | 1986-12-18 | 1986-12-18 | |
| US943,536 | 1986-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1297888C true CA1297888C (en) | 1992-03-24 |
Family
ID=25479827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000554442A Expired - Lifetime CA1297888C (en) | 1986-12-18 | 1987-12-16 | Process for preparing bis (ethoxythiocarbonyl)sulfide |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11490898B2 (en) | 2019-10-18 | 2022-11-08 | Depuy Synthes Products, Inc | Surgical saw blade |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354980A (en) * | 1981-06-04 | 1982-10-19 | Crozier Ronald D G | Process for producing alkyl xanthogen alkylformates |
-
1987
- 1987-02-17 ZA ZA879455A patent/ZA879455B/xx unknown
- 1987-12-15 EP EP87311015A patent/EP0274876B1/en not_active Expired - Lifetime
- 1987-12-15 JP JP62317289A patent/JPS63179854A/ja active Granted
- 1987-12-15 AT AT87311015T patent/ATE60577T1/de not_active IP Right Cessation
- 1987-12-15 DE DE8787311015T patent/DE3767865D1/de not_active Expired - Lifetime
- 1987-12-15 ES ES87311015T patent/ES2019948B3/es not_active Expired - Lifetime
- 1987-12-16 CA CA000554442A patent/CA1297888C/en not_active Expired - Lifetime
- 1987-12-17 AU AU82656/87A patent/AU593414B2/en not_active Ceased
- 1987-12-17 MX MX981487A patent/MX168553B/es unknown
- 1987-12-17 DK DK664987A patent/DK169405B1/da not_active IP Right Cessation
- 1987-12-17 IE IE343187A patent/IE60136B1/en not_active IP Right Cessation
-
1991
- 1991-01-31 GR GR91400098T patent/GR3001414T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE873431L (en) | 1988-06-18 |
| ATE60577T1 (de) | 1991-02-15 |
| AU593414B2 (en) | 1990-02-08 |
| ES2019948B3 (es) | 1991-07-16 |
| JPS63179854A (ja) | 1988-07-23 |
| DK664987A (da) | 1988-06-19 |
| EP0274876A1 (en) | 1988-07-20 |
| EP0274876B1 (en) | 1991-01-30 |
| ZA879455B (en) | 1989-07-26 |
| JPH0413338B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-03-09 |
| GR3001414T3 (en) | 1992-09-25 |
| DK664987D0 (da) | 1987-12-17 |
| DK169405B1 (da) | 1994-10-24 |
| DE3767865D1 (de) | 1991-03-07 |
| MX168553B (es) | 1993-05-31 |
| IE60136B1 (en) | 1994-06-01 |
| AU8265687A (en) | 1988-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |