DE869063C - Verfahren zur Herstellung von ª‡-Alkyl-3, 4-dichlorstyrolen - Google Patents
Verfahren zur Herstellung von ª‡-Alkyl-3, 4-dichlorstyrolenInfo
- Publication number
- DE869063C DE869063C DEP32061A DEP0032061A DE869063C DE 869063 C DE869063 C DE 869063C DE P32061 A DEP32061 A DE P32061A DE P0032061 A DEP0032061 A DE P0032061A DE 869063 C DE869063 C DE 869063C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- catalyst
- zinc oxide
- propylene
- dichlorostyrenes
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 18
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 16
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000011787 zinc oxide Substances 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- NYCKJGRASIXRFK-UHFFFAOYSA-N 1,2-dichloro-3-propan-2-ylbenzene Chemical class CC(C)C1=CC=CC(Cl)=C1Cl NYCKJGRASIXRFK-UHFFFAOYSA-N 0.000 description 6
- ZPVVNLOZNJMZMS-UHFFFAOYSA-N 1,2-dichloro-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(Cl)C(Cl)=C1 ZPVVNLOZNJMZMS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DQZUIRYHGMGWFY-UHFFFAOYSA-N 1,2-dichloro-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(Cl)C(Cl)=C1 DQZUIRYHGMGWFY-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- MLFRJNDWWVGFKR-UHFFFAOYSA-N benzene;cumene Chemical compound C1=CC=CC=C1.CC(C)C1=CC=CC=C1 MLFRJNDWWVGFKR-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US652618XA | 1946-11-06 | 1946-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE869063C true DE869063C (de) | 1953-03-02 |
Family
ID=22061470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP32061A Expired DE869063C (de) | 1946-11-06 | 1949-01-21 | Verfahren zur Herstellung von ª‡-Alkyl-3, 4-dichlorstyrolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE477127A (en(2012)) |
| DE (1) | DE869063C (en(2012)) |
| FR (1) | FR955119A (en(2012)) |
| GB (1) | GB652618A (en(2012)) |
| NL (1) | NL71363C (en(2012)) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54115328A (en) * | 1978-02-27 | 1979-09-07 | Ishihara Sangyo Kaisha Ltd | Preparation of 3,5-dichloro-alpha-methylstyrene |
-
0
- FR FR955119D patent/FR955119A/fr not_active Expired
- NL NL71363D patent/NL71363C/xx active
- BE BE477127D patent/BE477127A/xx unknown
-
1947
- 1947-10-21 GB GB28156/47A patent/GB652618A/en not_active Expired
-
1949
- 1949-01-21 DE DEP32061A patent/DE869063C/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE477127A (en(2012)) | |
| GB652618A (en) | 1951-04-25 |
| NL71363C (en(2012)) | |
| FR955119A (en(2012)) | 1950-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2510531A1 (de) | Verfahren zur herstellung von allylalkohol | |
| EP0129900B1 (de) | Verfahren zur Gewinnung von 1-Buten aus 2-Butene enthaltenden C4-Kohlenwasserstoffgemischen | |
| DE2705538A1 (de) | Verfahren zur reindarstellung von methyl-tert.-butylaether | |
| Cope et al. | The Introduction of Substituted Vinyl Groups. I. Isopropenyl Alkyl Malonic Esters | |
| DE869063C (de) | Verfahren zur Herstellung von ª‡-Alkyl-3, 4-dichlorstyrolen | |
| DE2052782B2 (de) | Verfahren zur Herstellung von olefinisch ungesättigten Verbindungen durch Dehydratisierung von Alkoholen | |
| DE2031900C3 (de) | Verfahren zur Herstellung von Isopren | |
| DE2225443C3 (de) | Verfahren zur Herstellung von Thiophenen | |
| DE1928632A1 (de) | Verfahren zur Herstellung von Isopren | |
| DE1793455B1 (de) | Verfahren zur Herstellung von Isopren | |
| DE2461922A1 (de) | Verfahren zur herstellung von tetrahydrofuran | |
| DE844442C (de) | Verfahren zur Herstellung von 1, 1-Dihalogen-1, 3-alkadienen | |
| DE859616C (de) | Verfahren zur Darstellung zweifach ungesaettigter aliphatisch-cyclischer 2-Methylbutanalverbindungen | |
| DE3034421A1 (de) | Verfahren zur herstellung von alkylestern gesaettigter aliphatischer carbonsaeuren | |
| DE895594C (de) | Verfahren zur Herstellung von 4-Chlor-3-methyl-ª‡-methylstyrol und 3-Chlor-4-methyl-ª‡-methylstyrol | |
| DE1468555A1 (de) | Verfahren zur Herstellung von Monoolefinen | |
| DE1088948B (de) | Verfahren zur Herstellung von Cyclohexadien | |
| DE1793330C3 (de) | Verfahren zur Herstellung Methylbutenen | |
| DE925715C (de) | Verfahren zur Abtrennung von 2, 4-Dimethyl-6-tert.-butylphenol aus Gemischen | |
| EP0564979B1 (de) | Verfahren zur Herstellung von Dixylylpropan | |
| CH495309A (de) | Verfahren zur Herstellung von Dihydromyrcenol | |
| DE869059C (de) | Verfahren zur Herstellung von Olefinen | |
| DE953973C (de) | Verfahren zur Herstellung von ungesaettigten AEthern | |
| DE2004785C3 (en(2012)) | ||
| DE857369C (de) | Verfahren zur Herstellung von 1, 4-Dichlorbuten-2 oder dessen Substitutionsprodukten, gegebenenfalls neben ungesaettigten Chloralkoholen |