DE2410248C3 - Stabilisierung eines aromatischen Chlorkohlenwasserstoffs - Google Patents
Stabilisierung eines aromatischen ChlorkohlenwasserstoffsInfo
- Publication number
- DE2410248C3 DE2410248C3 DE2410248A DE2410248A DE2410248C3 DE 2410248 C3 DE2410248 C3 DE 2410248C3 DE 2410248 A DE2410248 A DE 2410248A DE 2410248 A DE2410248 A DE 2410248A DE 2410248 C3 DE2410248 C3 DE 2410248C3
- Authority
- DE
- Germany
- Prior art keywords
- aluminum
- reaction
- chloride
- stabilization
- chlorinated hydrocarbon
- 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
- -1 aromatic chlorinated hydrocarbon Chemical class 0.000 title claims description 6
- 230000006641 stabilisation Effects 0.000 title claims description 3
- 238000011105 stabilization Methods 0.000 title claims description 3
- 229910052782 aluminium Inorganic materials 0.000 description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000004821 distillation Methods 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 125000004971 nitroalkyl group Chemical group 0.000 description 8
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 6
- 229940073608 benzyl chloride Drugs 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UZXMJXJSWUMRDH-UHFFFAOYSA-N 1-(1,2-dichloroethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1C(Cl)CCl UZXMJXJSWUMRDH-UHFFFAOYSA-N 0.000 description 2
- MZMVVHAHSRJOEO-UHFFFAOYSA-N 1-chloropropylbenzene Chemical compound CCC(Cl)C1=CC=CC=C1 MZMVVHAHSRJOEO-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- FCDQNUZMWWZPJO-UHFFFAOYSA-N 1,1-dichloroprop-2-enylbenzene Chemical compound C=CC(Cl)(Cl)C1=CC=CC=C1 FCDQNUZMWWZPJO-UHFFFAOYSA-N 0.000 description 1
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 1
- ZUQSDNDLOOHHCN-UHFFFAOYSA-N 1-nitroethane;nitromethane Chemical compound C[N+]([O-])=O.CC[N+]([O-])=O ZUQSDNDLOOHHCN-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- JJTUJRVKTPSEFZ-UHFFFAOYSA-N 3-chloroprop-2-enylbenzene Chemical compound ClC=CCC1=CC=CC=C1 JJTUJRVKTPSEFZ-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 229910001094 6061 aluminium alloy Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US337941A US3919335A (en) | 1973-03-05 | 1973-03-05 | Stabilization of chloroaromatics |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2410248A1 DE2410248A1 (de) | 1974-09-12 |
| DE2410248B2 DE2410248B2 (de) | 1979-01-04 |
| DE2410248C3 true DE2410248C3 (de) | 1979-09-06 |
Family
ID=23322691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2410248A Expired DE2410248C3 (de) | 1973-03-05 | 1974-03-04 | Stabilisierung eines aromatischen Chlorkohlenwasserstoffs |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3919335A (enExample) |
| JP (1) | JPS5339414B2 (enExample) |
| BE (1) | BE811887A (enExample) |
| CA (1) | CA999309A (enExample) |
| DE (1) | DE2410248C3 (enExample) |
| FR (1) | FR2220494B1 (enExample) |
| GB (1) | GB1455641A (enExample) |
| IT (1) | IT1008977B (enExample) |
| NL (1) | NL7402378A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1071239A (en) * | 1975-09-19 | 1980-02-05 | Rohm And Haas Company | Inhibitors for vinylbenzyl chloride and vinyltoluene decomposition |
| US4198276A (en) * | 1977-06-24 | 1980-04-15 | The Henkel Corporation | Process for thermally stabilizing sterols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2440100A (en) * | 1945-08-24 | 1948-04-20 | Du Pont | Solvent for degreasing iron and aluminum |
| US2517894A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Metal degreasing composition |
| US2567621A (en) * | 1950-05-23 | 1951-09-11 | Diamond Alkali Co | Stabilized tetrachloroethylene composition |
| US3060125A (en) * | 1958-11-28 | 1962-10-23 | Ethyl Corp | Stable solvent composition |
| US3549715A (en) * | 1959-05-13 | 1970-12-22 | Ppg Industries Inc | Stabilization |
-
1973
- 1973-03-05 US US337941A patent/US3919335A/en not_active Expired - Lifetime
-
1974
- 1974-02-18 CA CA192,802A patent/CA999309A/en not_active Expired
- 1974-02-21 NL NL7402378A patent/NL7402378A/xx unknown
- 1974-03-01 IT IT48865/74A patent/IT1008977B/it active
- 1974-03-04 FR FR7407239A patent/FR2220494B1/fr not_active Expired
- 1974-03-04 DE DE2410248A patent/DE2410248C3/de not_active Expired
- 1974-03-05 GB GB987974A patent/GB1455641A/en not_active Expired
- 1974-03-05 BE BE141655A patent/BE811887A/xx not_active IP Right Cessation
- 1974-03-05 JP JP2487574A patent/JPS5339414B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3919335A (en) | 1975-11-11 |
| JPS5339414B2 (enExample) | 1978-10-21 |
| NL7402378A (enExample) | 1974-09-09 |
| GB1455641A (en) | 1976-11-17 |
| FR2220494B1 (enExample) | 1977-09-30 |
| DE2410248A1 (de) | 1974-09-12 |
| IT1008977B (it) | 1976-11-30 |
| BE811887A (fr) | 1974-09-05 |
| FR2220494A1 (enExample) | 1974-10-04 |
| DE2410248B2 (de) | 1979-01-04 |
| CA999309A (en) | 1976-11-02 |
| JPS49117432A (enExample) | 1974-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |