DE2116977C3 - Verfahren zur Herstellung von 3-Aryl-1.1 -dihalogenpropenen-O) - Google Patents
Verfahren zur Herstellung von 3-Aryl-1.1 -dihalogenpropenen-O)Info
- Publication number
- DE2116977C3 DE2116977C3 DE2116977A DE2116977A DE2116977C3 DE 2116977 C3 DE2116977 C3 DE 2116977C3 DE 2116977 A DE2116977 A DE 2116977A DE 2116977 A DE2116977 A DE 2116977A DE 2116977 C3 DE2116977 C3 DE 2116977C3
- Authority
- DE
- Germany
- Prior art keywords
- propane
- carbon atoms
- chloride
- aryl
- ccl
- 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 18
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 35
- 239000000460 chlorine Substances 0.000 description 26
- 238000009835 boiling Methods 0.000 description 19
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000001294 propane Substances 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 9
- 239000002841 Lewis acid Substances 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 150000007517 lewis acids Chemical class 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- -1 benzyl halides Chemical class 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VKEIPALYOJMDAC-UHFFFAOYSA-N 3,3,3-trichloroprop-1-ene Chemical compound ClC(Cl)(Cl)C=C VKEIPALYOJMDAC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- AZASTUXQEBZETA-UHFFFAOYSA-N 1-chloro-4-(3,3-dichloroprop-2-enyl)benzene Chemical compound ClC(Cl)=CCC1=CC=C(Cl)C=C1 AZASTUXQEBZETA-UHFFFAOYSA-N 0.000 description 1
- SCLPYLCGFNBMNA-UHFFFAOYSA-N 2-bromo-3,3,3-trichloroprop-1-ene Chemical compound ClC(Cl)(Cl)C(Br)=C SCLPYLCGFNBMNA-UHFFFAOYSA-N 0.000 description 1
- YMZKHRBTRZQMQC-UHFFFAOYSA-N 2-chloro-3-(4-chlorophenyl)propanoyl chloride Chemical compound ClC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YMZKHRBTRZQMQC-UHFFFAOYSA-N 0.000 description 1
- AIZNASPCDNJRSP-UHFFFAOYSA-N 3,3,3-trichloro-2-methylprop-1-ene Chemical compound CC(=C)C(Cl)(Cl)Cl AIZNASPCDNJRSP-UHFFFAOYSA-N 0.000 description 1
- FIROAKDNSCQSTG-UHFFFAOYSA-N 3,3-dichloro-3-fluoroprop-1-ene Chemical compound FC(Cl)(Cl)C=C FIROAKDNSCQSTG-UHFFFAOYSA-N 0.000 description 1
- YJKIALIXRCSISK-UHFFFAOYSA-N Chlorfenprop-methyl Chemical compound COC(=O)C(Cl)CC1=CC=C(Cl)C=C1 YJKIALIXRCSISK-UHFFFAOYSA-N 0.000 description 1
- MYEMHDRTVHHLJN-UHFFFAOYSA-N ClC(CCC(C=CC(Cl)=C1)=C1Cl)(Cl)Cl Chemical compound ClC(CCC(C=CC(Cl)=C1)=C1Cl)(Cl)Cl MYEMHDRTVHHLJN-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 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
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 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
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- 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
- 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
- C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
-
- 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
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2116977A DE2116977C3 (de) | 1971-04-07 | 1971-04-07 | Verfahren zur Herstellung von 3-Aryl-1.1 -dihalogenpropenen-O) |
| RO197270347A RO58732A (OSRAM) | 1971-04-07 | 1972-03-31 | |
| SU1768164A SU444357A1 (ru) | 1972-04-04 | Способ получени 1,1-дигалоид3-арилпропена-1 | |
| DD162044A DD99152A5 (OSRAM) | 1971-04-07 | 1972-04-04 | |
| IL7239137A IL39137A (en) | 1971-04-07 | 1972-04-04 | Process for the preparation of 3-aryl-1,1-dihalopropenes-(1)and certain new such compounds |
| NL7204546A NL7204546A (OSRAM) | 1971-04-07 | 1972-04-05 | |
| IT89541/72A IT967045B (it) | 1971-04-07 | 1972-04-05 | Procedimento per la preparazione di 3 aril 1 i di alogeno propeni 1 |
| CH493572A CH574886A5 (OSRAM) | 1971-04-07 | 1972-04-05 | |
| GB1595772A GB1325127A (en) | 1971-04-07 | 1972-04-06 | Process for the preparation of 3-aryl-1,1-dihalopropenes-1 |
| PL1972154590A PL81985B1 (OSRAM) | 1971-04-07 | 1972-04-06 | |
| BE781736A BE781736A (fr) | 1971-04-07 | 1972-04-06 | Procede de preparation de 3-aryl-1,1-dihalogenopropenes-(1) |
| CS2334A CS167978B2 (OSRAM) | 1971-04-07 | 1972-04-07 | |
| CS620*[A CS167979B2 (OSRAM) | 1971-04-07 | 1972-04-07 | |
| FR7212326A FR2132776B1 (OSRAM) | 1971-04-07 | 1972-04-07 | |
| HUBA2724A HU164563B (OSRAM) | 1971-04-07 | 1972-04-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2116977A DE2116977C3 (de) | 1971-04-07 | 1971-04-07 | Verfahren zur Herstellung von 3-Aryl-1.1 -dihalogenpropenen-O) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2116977A1 DE2116977A1 (de) | 1972-10-19 |
| DE2116977B2 DE2116977B2 (de) | 1978-10-12 |
| DE2116977C3 true DE2116977C3 (de) | 1979-05-31 |
Family
ID=5804127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2116977A Expired DE2116977C3 (de) | 1971-04-07 | 1971-04-07 | Verfahren zur Herstellung von 3-Aryl-1.1 -dihalogenpropenen-O) |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE781736A (OSRAM) |
| CH (1) | CH574886A5 (OSRAM) |
| CS (2) | CS167979B2 (OSRAM) |
| DD (1) | DD99152A5 (OSRAM) |
| DE (1) | DE2116977C3 (OSRAM) |
| FR (1) | FR2132776B1 (OSRAM) |
| GB (1) | GB1325127A (OSRAM) |
| HU (1) | HU164563B (OSRAM) |
| IL (1) | IL39137A (OSRAM) |
| IT (1) | IT967045B (OSRAM) |
| NL (1) | NL7204546A (OSRAM) |
| PL (1) | PL81985B1 (OSRAM) |
| RO (1) | RO58732A (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2536504C3 (de) * | 1975-08-16 | 1985-06-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Halogendienen |
-
1971
- 1971-04-07 DE DE2116977A patent/DE2116977C3/de not_active Expired
-
1972
- 1972-03-31 RO RO197270347A patent/RO58732A/ro unknown
- 1972-04-04 IL IL7239137A patent/IL39137A/xx unknown
- 1972-04-04 DD DD162044A patent/DD99152A5/xx unknown
- 1972-04-05 IT IT89541/72A patent/IT967045B/it active
- 1972-04-05 NL NL7204546A patent/NL7204546A/xx unknown
- 1972-04-05 CH CH493572A patent/CH574886A5/xx not_active IP Right Cessation
- 1972-04-06 GB GB1595772A patent/GB1325127A/en not_active Expired
- 1972-04-06 BE BE781736A patent/BE781736A/xx unknown
- 1972-04-06 PL PL1972154590A patent/PL81985B1/pl unknown
- 1972-04-07 CS CS620*[A patent/CS167979B2/cs unknown
- 1972-04-07 HU HUBA2724A patent/HU164563B/hu unknown
- 1972-04-07 CS CS2334A patent/CS167978B2/cs unknown
- 1972-04-07 FR FR7212326A patent/FR2132776B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU444357A3 (ru) | 1974-09-25 |
| IL39137A (en) | 1975-12-31 |
| CH574886A5 (OSRAM) | 1976-04-30 |
| BE781736A (fr) | 1972-10-06 |
| RO58732A (OSRAM) | 1976-11-15 |
| FR2132776B1 (OSRAM) | 1977-04-01 |
| HU164563B (OSRAM) | 1974-03-28 |
| IT967045B (it) | 1974-02-28 |
| PL81985B1 (OSRAM) | 1975-10-31 |
| CS167979B2 (OSRAM) | 1976-05-28 |
| DE2116977A1 (de) | 1972-10-19 |
| DE2116977B2 (de) | 1978-10-12 |
| DD99152A5 (OSRAM) | 1973-07-20 |
| CS167978B2 (OSRAM) | 1976-05-28 |
| NL7204546A (OSRAM) | 1972-10-10 |
| IL39137A0 (en) | 1972-06-28 |
| FR2132776A1 (OSRAM) | 1972-11-24 |
| GB1325127A (en) | 1973-08-01 |
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