GB840658A - Improvements in the manufacture of thiolactones - Google Patents
Improvements in the manufacture of thiolactonesInfo
- Publication number
- GB840658A GB840658A GB27874/56A GB2787456A GB840658A GB 840658 A GB840658 A GB 840658A GB 27874/56 A GB27874/56 A GB 27874/56A GB 2787456 A GB2787456 A GB 2787456A GB 840658 A GB840658 A GB 840658A
- Authority
- GB
- United Kingdom
- Prior art keywords
- beta
- gamma
- chloride
- propionyl chloride
- bromo
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 150000004820 halides Chemical class 0.000 abstract 5
- -1 Alkali metal sulphides Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 229910052976 metal sulfide Inorganic materials 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- PVZDNGBOEMTHPG-UHFFFAOYSA-N oxetane-2-thione Chemical compound S=C1CCO1 PVZDNGBOEMTHPG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002002 slurry Substances 0.000 abstract 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- XVDKXSXPKUZSGB-UHFFFAOYSA-N 2-(bromomethyl)pentanoyl chloride Chemical compound C(CC)C(C(=O)Cl)CBr XVDKXSXPKUZSGB-UHFFFAOYSA-N 0.000 abstract 1
- ZVDKTPOXSAEUQU-UHFFFAOYSA-N 3-bromo-2-methylpropanoyl chloride Chemical compound BrCC(C)C(Cl)=O ZVDKTPOXSAEUQU-UHFFFAOYSA-N 0.000 abstract 1
- HLQATVNBENMQCZ-UHFFFAOYSA-N 3-bromo-2-phenylpropanoyl chloride Chemical compound ClC(=O)C(CBr)C1=CC=CC=C1 HLQATVNBENMQCZ-UHFFFAOYSA-N 0.000 abstract 1
- USWSCNMIXXOFJQ-UHFFFAOYSA-N 3-bromoheptanoyl chloride Chemical compound C(CCC)C(CC(=O)Cl)Br USWSCNMIXXOFJQ-UHFFFAOYSA-N 0.000 abstract 1
- OPYFTKZPJVSHJK-UHFFFAOYSA-N 3-bromopentanoyl bromide Chemical compound C(C)C(CC(=O)Br)Br OPYFTKZPJVSHJK-UHFFFAOYSA-N 0.000 abstract 1
- IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 abstract 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 abstract 1
- POSKIQSQBNUUAV-UHFFFAOYSA-N 3-iodo-3-phenylpropanoyl chloride Chemical compound C1(=CC=CC=C1)C(CC(=O)Cl)I POSKIQSQBNUUAV-UHFFFAOYSA-N 0.000 abstract 1
- BVGKKICUUAFHFE-UHFFFAOYSA-N 3-iodopropanoyl chloride Chemical compound ClC(=O)CCI BVGKKICUUAFHFE-UHFFFAOYSA-N 0.000 abstract 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- KMSNYNIWEORQDJ-UHFFFAOYSA-N Dihydro-2(3H)-thiophenone Chemical compound O=C1CCCS1 KMSNYNIWEORQDJ-UHFFFAOYSA-N 0.000 abstract 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- CJDPJFRMHVXWPT-UHFFFAOYSA-N barium sulfide Chemical class [S-2].[Ba+2] CJDPJFRMHVXWPT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 229910010272 inorganic material Inorganic materials 0.000 abstract 1
- 239000011147 inorganic material Substances 0.000 abstract 1
- 229940057995 liquid paraffin Drugs 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 229910052712 strontium Inorganic materials 0.000 abstract 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Solid polymers believed to have the general formula <FORM:0840658/IV(a)/1> wherein n is 1 or 2, the R's represent hydrogen or alkyl or aryl radicals, and y is greater than 1, are obtained in the preparation of beta- or gamma-thiolactones by reacting a beta- or gamma halo acid halide of the general formula <FORM:0840658/IV(a)/2> wherein X represents a halogen and n and R are as defined above, with a normal metalsulphide having not more than about 4 mols. of combined water and under substantially anhydrous conditions (see Group IV (b)).ALSO:The invention comprises beta-thiopropiolactone and a method of making beta- and gammathiolactones having the general formula <FORM:0840658/IV(b)/1> wherein the Rs represent hydrogen or the same or different alkyl or aryl radicals and n is 1 or 2 by reacting a beta- or gamma-halo acid halide <FORM:0840658/IV(b)/2> in which X is a halogen, with a normal metal sulphide having not more than about 4 mols. of combined water and under substantially anhydrous conditions. Alkali metal sulphides are preferred but ferrous, ferric, zinc, copper, calcium, magnesium, strontium and barium sulphides may also be used. The acid halide alone or in solution may be added to dry metal sulphide or a slurry thereof; alternatively, the sulphide may be added to the acid halide or both reagents diluted or not may be fed simultaneously into a reactor. Suitable diluents are carbon disulphide and liquid paraffin and aromatic hydrocarbons. The reagents are normally used in equimolar amounts at temperatures from about - 10 DEG to about 75 DEG C. The products are recovered by filtration to remove inorganic material followed by fractional distillation or crystallization. In typical examples: (1) a carbon disulphide solution of beta-bromopropionyl chloride is slowly added to a cooled stirred slurry of anhydrous sodium sulphide in carbon disulphide to form beta-thio propiolactone: (3) gamma-chloro butyryl chloride is similarly reacted with sodium sulphide yielding gamma-thiobutyrolactone. Other specified acid halides include beta-chloro propionyl chloride, beta-iodopropionyl chloride, 2-methyl-3 - bromo propionyl chloride, 3 - ethyl - 3-bromo propionyl bromide, 2 : 3-dimethyl-3-bromo-propionyl chloride, 3-butyl-3-bromo propionyl chloride, 2 - propyl - 3 - bromo propionyl chloride, 2 - phenyl - 3 - bromo propionyl chloride, 3 - phenyl 3 - iodo propionyl chloride and the analogous gamma-halogenated butyryl halides.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US840658XA | 1955-09-20 | 1955-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB840658A true GB840658A (en) | 1960-07-06 |
Family
ID=22182672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27874/56A Expired GB840658A (en) | 1955-09-20 | 1956-09-12 | Improvements in the manufacture of thiolactones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB840658A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367921A (en) * | 1965-09-07 | 1968-02-06 | Du Pont | Propiothiolactone polymers |
| US4906759A (en) * | 1986-09-24 | 1990-03-06 | Lonza Ltd. | Process for the production of 4-alkoxy-2(5H) thiophenones |
| US4997957A (en) * | 1985-01-16 | 1991-03-05 | Lonza, Ltd. | Process for the production of thiotetronic acid |
-
1956
- 1956-09-12 GB GB27874/56A patent/GB840658A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367921A (en) * | 1965-09-07 | 1968-02-06 | Du Pont | Propiothiolactone polymers |
| US4997957A (en) * | 1985-01-16 | 1991-03-05 | Lonza, Ltd. | Process for the production of thiotetronic acid |
| US5093503A (en) * | 1985-01-16 | 1992-03-03 | Lonza Ltd. | Process for the production of thiotetronic acid |
| US4906759A (en) * | 1986-09-24 | 1990-03-06 | Lonza Ltd. | Process for the production of 4-alkoxy-2(5H) thiophenones |
| US4906765A (en) * | 1986-09-24 | 1990-03-06 | Lonza Ltd. | Process for the production of 4-alkoxy-2(5H) thiophenones |
| US4931570A (en) * | 1986-09-24 | 1990-06-05 | Lonza Ltd. | Process for the production of 4-alkoxy-2(5H) thiophenones |
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