← Back to Patent Explorer
US3896183A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the liquid phase chlorination of c6' c18 alpha-olefin hydrocarbons

Assignee: Dover Chemical Corp
•
Filing: 1974-03-11
•
Granted: 1975-07-22
•
Expires: 1994-03-11
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract An improved process for the liquid phase chlorination of a normally liquid hydrocarbon mixture is provided which is capable of yielding a product of enhanced quality through the elimination of an undesirable side reaction in the gaseous mixture which is in contact with the liquid mass where the desired chlorination reaction is carried out. The hydrocarbon feed contains on the average 6 to 18 carbon atoms per molecule and consists mainly of normal alpha-olefins. A minor quantity of an additive (e.g. carbon tetrachloride) is provided in the reaction zone and is at least partially present in the gaseous mixture where an undesirable reaction between hydrocarbon vapor and gaseous chlorine is eliminated. An improved chlorinated hydrocarbon product is formed in the reaction zone.

Inventors

  • 👤 Albert J Henderson
  • 👤 John E Krol

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 23:02
CPC Classifications
C; C07; C07C; C07C17/00

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 228 words
AN IMPROVED PROCESS FOR THE PRODUCTION OF CHLORINATED HYDROCARBONS CONTAINING ABOUT 20 TO 73 PERCENT CHLORINE BY WEIGHT COMPRISING CHLORINATING IN THE ABSENCE OF A LEWIS ACID CATALYST A HYDROCARBON MIXTURE WHICH IS A LIQUID AT ROOM TEMPERATURE CONTAINING ON THE AVERAGE 6 TO 1, CARBON ATOMS PER MOLECULE AND CONSISTING MAINLY OF NORMAL ALPHA-OLEFINS WHILE PRESENT IN THE LIQUID STATE AT A TEMPERATURE OF ABOUT 25* TO 120*C. IN A REACTION ZONE WHEREIN A GASEOUS MIXTURE COMPRISING A MINOR PROPORTION OF HYDROCARBON VAPOR AND GASEOUS CHLORINE EXISTS IN CONTACT WITH SAID LIQUID HYDROCARBON DURING AT LEAST A PORTION OF THE CHLORINATION REACTION WHILE PROVIDING IN SAID REACTION ZONE ABOUT 2 TO 20PERCENT BY WEIGHT BASED UPON THE WEIGHT OF SAID HYDROCARBON MIXTURE OF AN ADDITIVE SELECTED FROM THE GROUP CONSISTING OF CARBON TETRACHLORIDE, CHLOROFORM, ETHYLENE DICHLORIDE, 1,1,1-TRICHLOROETHANE, 1,1,2TRICHLOROETHANE, AND PERCHLOROETHANE AND WITH NO SOLVENT FOR SAID HYDROCARBON MIXTURE EING PRESENT IN SAID REACTION ZONE OTHER THAN SAID MINOR CONCENTRATION OF SAID ADDITIVE WHICH PRIMARILY SERVES A ROLE OTHER THAN A SOLVENT AND WHICH IS AT LEAST PARTIALLY VOLATILIZED AND PRESENT IN SAID GASEOUS MIXTURE IN CONTACT WITH SAID LIQUID HYDROCARBON WHERE IT SERVE TO ELIMINATE AN UNDESIRABLE REACTION BETWEEN SAID HYDROCARBON VAPOR AND SAID GASEOUS CHLORINE THEREBY IMPROVING THE QUALITY OF THE RESULTING CHLORINATED HYDROCARBON PRODUCT, AND THEREAFTER SUBSTANTIALLY REMOVING SAID ADDITIVE FROM SAID CHLORINATED HYDROCARBON PRODUCT.
Claim 2
Dependent Claim 228 words
AN IMPROVED PROCESS FOR THE PRODUCTION OF CHLORINATED HYDROCARBONS CONTAINING ABOUT 20 TO 73 PERCENT CHLORINE BY WEIGHT COMPRISING CHLORINATING IN THE ABSENCE OF A LEWIS ACID CATALYST A HYDROCARBON MIXTURE WHICH IS A LIQUID AT ROOM TEMPERATURE CONTAINING ON THE AVERAGE 6 TO 1, CARBON ATOMS PER MOLECULE AND CONSISTING MAINLY OF NORMAL ALPHA-OLEFINS WHILE PRESENT IN THE LIQUID STATE AT A TEMPERATURE OF ABOUT 25* TO 120*C. IN A REACTION ZONE WHEREIN A GASEOUS MIXTURE COMPRISING A MINOR PROPORTION OF HYDROCARBON VAPOR AND GASEOUS CHLORINE EXISTS IN CONTACT WITH SAID LIQUID HYDROCARBON DURING AT LEAST A PORTION OF THE CHLORINATION REACTION WHILE PROVIDING IN SAID REACTION ZONE ABOUT 2 TO 20PERCENT BY WEIGHT BASED UPON THE WEIGHT OF SAID HYDROCARBON MIXTURE OF AN ADDITIVE SELECTED FROM THE GROUP CONSISTING OF CARBON TETRACHLORIDE, CHLOROFORM, ETHYLENE DICHLORIDE, 1,1,1-TRICHLOROETHANE, 1,1,2TRICHLOROETHANE, AND PERCHLOROETHANE AND WITH NO SOLVENT FOR SAID HYDROCARBON MIXTURE EING PRESENT IN SAID REACTION ZONE OTHER THAN SAID MINOR CONCENTRATION OF SAID ADDITIVE WHICH PRIMARILY SERVES A ROLE OTHER THAN A SOLVENT AND WHICH IS AT LEAST PARTIALLY VOLATILIZED AND PRESENT IN SAID GASEOUS MIXTURE IN CONTACT WITH SAID LIQUID HYDROCARBON WHERE IT SERVE TO ELIMINATE AN UNDESIRABLE REACTION BETWEEN SAID HYDROCARBON VAPOR AND SAID GASEOUS CHLORINE THEREBY IMPROVING THE QUALITY OF THE RESULTING CHLORINATED HYDROCARBON PRODUCT, AND THEREAFTER SUBSTANTIALLY REMOVING SAID ADDITIVE FROM SAID CHLORINATED HYDROCARBON PRODUCT.
Claim 3
Dependent Claim 26 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said hydrocarbon mixture contains at least 90 percent normal alpha-olefins by weight.
Claim 4
Dependent Claim 28 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said hydrocarbon mixture contains on the average 11 to 14 carbon atoms per molecule.
Claim 5
Dependent Claim 27 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said hydrocarbon mixture during said chlorination is provided at about 70* to 110*C.
Claim 6
Dependent Claim 41 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said additive is present in said reaction zone in a concentration of about 5 to 10 percent by weight based upon the weight of said hydrocarbon mixture.
Claim 7
Dependent Claim 19 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said additive is carbon tetrachloride.
Claim 8
Dependent Claim 27 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said additive is dissolved in said liquid hydrocarbon mixture prior to said chlorination.
Claim 9
Dependent Claim 22 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said additive is under reflux during said chlorination.
Claim 10
Dependent Claim 29 words
An improved process for the production of chlorinated hydrocarbons according to claim 1 wherein said resulting chlorinated paraffin hydrocarbon product contains about 40 to 70 percent chlorine by weight.
Claim 11
Dependent Claim 215 words
An improved process for the production of chlorinated hydrocarbons containing about 40 to 70 percent chlorine by weight comprising chlorinating in the absence of a Lewis acid catalyst a hydrocarbon mixture which is a liquid at room temperature containing on the average 6 to 18 carbon atoms per molecule and consisting mainly of normal alpha-olefins while present in the liquid state at a temperature of about 25* to 100*C. in a reaction zone wherein a gaseous mixture comprising a minor proportion of hydrocarbon vapor and gaseous chlorine exists in contact with said liquid hydrocarbon during at least a portion of the chlorination reaction while providing in said reaction zone about 5 to 10 percent by weight based upon the weight of said hydrocarbon mixture of carbon tetrachloride additive and with no solvent for said hydrocarbon mixture being present in said reaction zone other than said minor concentration of said additive which primarily serves a role other than a solvent and which is at least partially volatilized and present in said gaseous mixture in contact with said liquid hydrocarbon where it serves to eliminate an undesirable reaction between said hydrocarbon vapor and said gaseous chlorine thereby improving the quality of the resulting chlorinated hydrocarbon product, and thereafter substantially removing said additive from said chlorinated hydrocarbon product.
Claim 12
Dependent Claim 215 words
An improved process for the production of chlorinated hydrocarbons containing about 40 to 70 percent chlorine by weight comprising chlorinating in the absence of a Lewis acid catalyst a hydrocarbon mixture which is a liquid at room temperature containing on the average 6 to 18 carbon atoms per molecule and consisting mainly of normal alpha-olefins while present in the liquid state at a temperature of about 25* to 100*C. in a reaction zone wherein a gaseous mixture comprising a minor proportion of hydrocarbon vapor and gaseous chlorine exists in contact with said liquid hydrocarbon during at least a portion of the chlorination reaction while providing in said reaction zone about 5 to 10 percent by weight based upon the weight of said hydrocarbon mixture of carbon tetrachloride additive and with no solvent for said hydrocarbon mixture being present in said reaction zone other than said minor concentration of said additive which primarily serves a role other than a solvent and which is at least partially volatilized and present in said gaseous mixture in contact with said liquid hydrocarbon where it serves to eliminate an undesirable reaction between said hydrocarbon vapor and said gaseous chlorine thereby improving the quality of the resulting chlorinated hydrocarbon product, and thereafter substantially removing said additive from said chlorinated hydrocarbon product.
Claim 13
Dependent Claim 29 words
An improved process for the production of chlorinated hydrocarbons according to claim 10 wherein said hydrocarbon mixture contains on the average of 11 to 14 carbon atoms per molecule.
Claim 14
Dependent Claim 26 words
An improved process for the production of chlorinated hydrocarbons according to claim 10 wherein said hydrocarbon mixture contains at least 95 percent normal alpha-olefins by weight.
Claim 15
Dependent Claim 29 words
An improved process for the production of chlorinated hydrocarbons according to claim 10 wherein said carbon tetrachloride additive is dissolved in said liquid hydrocarbon mixture prior to said chlorination.
Claim 16
Dependent Claim 26 words
An improved process for the production of chlorinated hydrocarbons according to claim 10 whErein gaseous chlorine is continuously introduced into said hydrocarbon mixture during said chlorination.
Claim 17
Dependent Claim 24 words
An improved process for the production of chlorinated paraffin hydrocarbons according to claim 10 wherein said carbon tetrachloride is under reflux during said chlorination.

References Cited (Backward Citations)

US1129165A Cited
US3338982A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-07-21 1979-01-20 1979-07-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-07-21 1983-01-20 1983-07-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-07-21 1987-01-20 1987-07-22 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag