US1045139A - Process of making chlorinated hydrocarbons - Google Patents
Process of making chlorinated hydrocarbons Download PDFInfo
- Publication number
- US1045139A US1045139A US64800011A US1911648000A US1045139A US 1045139 A US1045139 A US 1045139A US 64800011 A US64800011 A US 64800011A US 1911648000 A US1911648000 A US 1911648000A US 1045139 A US1045139 A US 1045139A
- Authority
- US
- United States
- Prior art keywords
- chlorinated hydrocarbons
- making
- making chlorinated
- hydrocarbons
- olefinic
- 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
- 238000000034 method Methods 0.000 title description 8
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 title description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MOUDFOLIRVUWKC-UHFFFAOYSA-N 3,3-dichloropentane Chemical compound CCC(Cl)(Cl)CC MOUDFOLIRVUWKC-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Definitions
- My present invention consistsin a process reaction varies for diflerenthydrocarbons
- the sulfurous acid which is set free during the reaction remains dissolved in the reaction product andis driven 0H and can be used again for the manufacture of sulfuryl .chlorid.
- the following example will serve to illustrate further the nature of my invention, which, however, is not confined to this. example.
- the parts' are by weight. Thoroughly cool about'eighty partsof trimethylethylene (amylene) and add. to it- (slowly and while stirring well) about one hundred and thirty-five parts of cold sulfuryl chlorid, regulating the temperature so that Specification of Letters Patent.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
NTTED STTES OTTO GRAUL, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, ASSIGNOR 'IO BADISCHE ANILIN & SODA FABRIK, 0F LUDWIGSHAFEN-ON-THE-RI-IINE, GERMANY, A GOR- IORATION.
PROCESS OF MAKING GHLORINATED HYDROGARBONS.
1,045,139. No Drawing.
To all whom it may concern:
Be it known that I, O'r'ro GRAUL, subject of the Duke of Anhalt, residing at Lud- Wi shafen-on-the-Rhine, Germany, have invented new and useful Improvements in Processes of Making Chlorinated Hydrocarbons, of which the following is a specification.
When olefinic hydrocarbons, such as the olefins themselves C H, are treated with a halogen, there is a difference in the result, as is well known, according to whether chlorin or bromin is used. The reaction with bro- .min results in the smoothproduction of the compounds containing two additional bro-' -min atoms, whereas the addition of chlorin has hitherto always been'accompanied by the formation of considerable quantities of substitution products.
My present invention consistsin a process reaction varies for diflerenthydrocarbons,
but can readily be ascertained. The sulfurous acid which is set free during the reaction remains dissolved in the reaction product andis driven 0H and can be used again for the manufacture of sulfuryl .chlorid.
' The following example will serve to illustrate further the nature of my invention, which, however, is not confined to this. example. The parts' are by weight. Thoroughly cool about'eighty partsof trimethylethylene (amylene) and add. to it- (slowly and while stirring well) about one hundred and thirty-five parts of cold sulfuryl chlorid, regulating the temperature so that Specification of Letters Patent.
I witnesses.
Patented Nov. 26, 1912.
Application filedfieptember 6, 1911. Serial No. 648,000.
tween minus two degrees and zero centigrade. Continue stirring for some time after the addition is effected. Distii off the sulfurous acid and the excess of trimethylethylene and purify the residue, if desired, by distilling in vacuo. The dichlor-pentane thus obtained boils at from forty-eight to fifty-two degrees Centigrade at fortyeight millimeters pressure. This example can, be varied in many respects, for instance if it is desired to produce the dichlorid continuously, the reagents can be separately cooled and run together in a worm in which they gradually assume the temperature at which the reaction takes place. My invention can also be similarly applied to the ghlorination of the other olefinic hydrocarone.
Now what I claim is 1. The process of making chlorinated hydrocarbons by treating olefinic hydrocarbons with sulfuryl chlorid.
2. The process of making chlorinated hydrocarbons by treating an excess of olefinic hydrocarbon with sulfuryl chlorid, distilling oil? the sulfur dioxid and excess of olefinic hydrocarbon and purifying the resulting chlorinated hydrocarbon by distillation.
3. The process of making chlorinated hydrocarbons by treating amylene with sulfuryl chlorid. s
4. The process of making chlorinated hy-v In testimony whereof I have hereunto setmy hand in the presence of two subscribing o '0TT0 GRAUL. Witnesses:
J. ALEC. LLoYD,
J osnrn Fame.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64800011A US1045139A (en) | 1911-09-06 | 1911-09-06 | Process of making chlorinated hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64800011A US1045139A (en) | 1911-09-06 | 1911-09-06 | Process of making chlorinated hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1045139A true US1045139A (en) | 1912-11-26 |
Family
ID=3113413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US64800011A Expired - Lifetime US1045139A (en) | 1911-09-06 | 1911-09-06 | Process of making chlorinated hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1045139A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2549425A (en) * | 1947-12-31 | 1951-04-17 | Standard Oil Dev Co | Condensation of alkylated naphthalene with a sulfur oxyhalide in presence of friedel-crafts catalyst and mineral oil compositions containing same |
| US2698348A (en) * | 1952-04-02 | 1954-12-28 | Ethyl Corp | Halogenation |
| US2698347A (en) * | 1951-01-30 | 1954-12-28 | Ethyl Corp | Manufacture of halogen compounds |
| US3304336A (en) * | 1964-05-27 | 1967-02-14 | Detrex Chem Ind | Dehydrochlorination of polychlorinated hydrocarbons |
-
1911
- 1911-09-06 US US64800011A patent/US1045139A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2549425A (en) * | 1947-12-31 | 1951-04-17 | Standard Oil Dev Co | Condensation of alkylated naphthalene with a sulfur oxyhalide in presence of friedel-crafts catalyst and mineral oil compositions containing same |
| US2698347A (en) * | 1951-01-30 | 1954-12-28 | Ethyl Corp | Manufacture of halogen compounds |
| US2698348A (en) * | 1952-04-02 | 1954-12-28 | Ethyl Corp | Halogenation |
| US3304336A (en) * | 1964-05-27 | 1967-02-14 | Detrex Chem Ind | Dehydrochlorination of polychlorinated hydrocarbons |
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