BE498176A - - Google Patents
Info
- Publication number
- BE498176A BE498176A BE498176DA BE498176A BE 498176 A BE498176 A BE 498176A BE 498176D A BE498176D A BE 498176DA BE 498176 A BE498176 A BE 498176A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- cyclopentadiene
- acetylene
- reaction
- reaction zone
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 41
- ZSWFCLXCOIISFI-UHFFFAOYSA-N Cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 230000005484 gravity Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000002045 lasting Effects 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 118
- 238000002360 preparation method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 125000004429 atoms Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- -1 cyclic dienes Chemical class 0.000 description 3
- 230000000749 insecticidal Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000003068 static Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VUNCWTMEJYMOOR-UHFFFAOYSA-N Hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- IHAXIFZOERJWDF-UHFFFAOYSA-N 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hepta-2,5-diene Chemical compound C1=CC2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl IHAXIFZOERJWDF-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-Cycloheptadiene Chemical class C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- AJVNVNXTHQJGQK-UHFFFAOYSA-N C1=CC=CC1.C#C Chemical group C1=CC=CC1.C#C AJVNVNXTHQJGQK-UHFFFAOYSA-N 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N Norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Phenylacetylene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002238 attenuated Effects 0.000 description 1
- MKOSBHNWXFSHSW-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-en-5-ol Chemical compound C1C2C(O)CC1C=C2 MKOSBHNWXFSHSW-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002234 fulvenes Chemical class 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- OGQVROWWFUXRST-UHFFFAOYSA-N heptadiene group Chemical class C=CC=CCCC OGQVROWWFUXRST-UHFFFAOYSA-N 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000000670 limiting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002790 naphthalenes Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000087 stabilizing Effects 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/27—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with a bicyclo ring system containing seven carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/30—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by a Diels-Alder synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/50—Diels-Alder conversion
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/26—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with a bicyclo ring system containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE498176A true BE498176A (xx) |
Family
ID=140930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE498176D BE498176A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE498176A (xx) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2804483A (en) * | 1954-01-12 | 1957-08-27 | Velsicol Chemical Corp | Production of alpha, alpha, alpha, 2, 3, 4-hexachlorotoluene |
| US2813915A (en) * | 1955-08-10 | 1957-11-19 | Shell Dev | Production of 1, 2, 3, 4, 7, 7-hexachlorobicyclo[2.2.1]-2, 5-heptadiene |
| US2881223A (en) * | 1954-06-17 | 1959-04-07 | Universal Oil Prod Co | Bicyclic compounds containing nuclearly substituted halogen |
| US2900419A (en) * | 1956-09-24 | 1959-08-18 | Shell Dev | Reaction of halocyclopentadienes with acetylene |
| DE1069147B (de) * | 1959-11-19 | N. V. Die Bataafsche Petroleum Maatsichappij, Den Haag | Verfahren zur Herstellung von 1, 4, 5, 6, 7, 7 - Hexachlorbicyclo-[2, 2, l]--heptadien-(2,5) | |
| US2925445A (en) * | 1952-12-22 | 1960-02-16 | Shell Dev | Production of chlorinated bicyclic hydrocarbons |
| US2930781A (en) * | 1957-09-30 | 1960-03-29 | Universal Oil Prod Co | Preparation of resins |
| US2930782A (en) * | 1957-09-30 | 1960-03-29 | Universal Oil Prod Co | Preparation of resins |
| DE1112737B (de) * | 1959-02-11 | 1961-08-17 | Velsicol Chemical Corp | Verfahren zur Herstellung chlorierter 5-AEthinylbicyclo-[2,2,1]-heptene-(2) |
-
0
- BE BE498176D patent/BE498176A/fr unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069147B (de) * | 1959-11-19 | N. V. Die Bataafsche Petroleum Maatsichappij, Den Haag | Verfahren zur Herstellung von 1, 4, 5, 6, 7, 7 - Hexachlorbicyclo-[2, 2, l]--heptadien-(2,5) | |
| US2925445A (en) * | 1952-12-22 | 1960-02-16 | Shell Dev | Production of chlorinated bicyclic hydrocarbons |
| US2804483A (en) * | 1954-01-12 | 1957-08-27 | Velsicol Chemical Corp | Production of alpha, alpha, alpha, 2, 3, 4-hexachlorotoluene |
| US2881223A (en) * | 1954-06-17 | 1959-04-07 | Universal Oil Prod Co | Bicyclic compounds containing nuclearly substituted halogen |
| US2813915A (en) * | 1955-08-10 | 1957-11-19 | Shell Dev | Production of 1, 2, 3, 4, 7, 7-hexachlorobicyclo[2.2.1]-2, 5-heptadiene |
| DE1418334B1 (de) * | 1955-08-10 | 1971-01-07 | Shell Oil Co | Verfahren zur Herstellung von 1,2,3,4,7,7-Hexachlorbicyclo[2,2,1]-2,5-heptadien aus Hexachlorcyclopentadien und Acetylen |
| US2900419A (en) * | 1956-09-24 | 1959-08-18 | Shell Dev | Reaction of halocyclopentadienes with acetylene |
| US2930781A (en) * | 1957-09-30 | 1960-03-29 | Universal Oil Prod Co | Preparation of resins |
| US2930782A (en) * | 1957-09-30 | 1960-03-29 | Universal Oil Prod Co | Preparation of resins |
| DE1112737B (de) * | 1959-02-11 | 1961-08-17 | Velsicol Chemical Corp | Verfahren zur Herstellung chlorierter 5-AEthinylbicyclo-[2,2,1]-heptene-(2) |
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