IL27103A - Process for the production of alpha,beta-dichlorostilbenes - Google Patents

Process for the production of alpha,beta-dichlorostilbenes

Info

Publication number: IL27103A
Authority: IL; Israel
Prior art keywords: parts; volume; tetrachloro; mixture; added
Prior art date: 1965-12-21

Application number

IL2710366A

Other languages

English (en)

Original Assignee

Geigy Ag J R

Priority date (The priority date 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 date listed.)

1965-12-21

Filing date

1966-12-20

Publication date

1970-06-17

1966-12-20 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1970-06-17 Publication of IL27103A publication Critical patent/IL27103A/en

Links

238000000034 method Methods 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title claims description 6
FTIHFTVXYNBUSM-UHFFFAOYSA-N (1,2-dichloro-2-phenylethenyl)benzene Chemical class C=1C=CC=CC=1C(Cl)=C(Cl)C1=CC=CC=C1 FTIHFTVXYNBUSM-UHFFFAOYSA-N 0.000 title 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
229910052742 iron Inorganic materials 0.000 claims description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
238000006298 dechlorination reaction Methods 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
239000000956 alloy Substances 0.000 claims description 4
229910045601 alloy Inorganic materials 0.000 claims description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
QVYYOKWPCQYKEY-UHFFFAOYSA-N [Fe].[Co] Chemical compound [Fe].[Co] QVYYOKWPCQYKEY-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000000706 filtrate Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
239000000155 melt Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
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 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
OFTPEPKEBMRIQQ-UHFFFAOYSA-N (1,1,2,2-tetrachloro-2-phenylethyl)benzene Chemical class C=1C=CC=CC=1C(Cl)(Cl)C(Cl)(Cl)C1=CC=CC=C1 OFTPEPKEBMRIQQ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000000197 pyrolysis Methods 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
AHJKRLASYNVKDZ-UHFFFAOYSA-N DDD Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 AHJKRLASYNVKDZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
102000005936 beta-Galactosidase Human genes 0.000 description 1
108010005774 beta-Galactosidase Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000000382 dechlorinating effect Effects 0.000 description 1
150000001470 diamides Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000001629 stilbenes Chemical class 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000004753 textile Substances 0.000 description 1
230000017105 transposition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL2710366A 1965-12-21 1966-12-20 Process for the production of alpha,beta-dichlorostilbenes IL27103A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1759265A CH456571A (de)	1965-12-21	1965-12-21	Verfahren zur Herstellung von a,B-Dichlor-stilbenen

Publications (1)

Publication Number	Publication Date
IL27103A true IL27103A (en)	1970-06-17

Family

ID=4426569

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2710366A IL27103A (en)	1965-12-21	1966-12-20	Process for the production of alpha,beta-dichlorostilbenes

Country Status (4)

Country	Link
CH (1)	CH456571A (de)
DE (1)	DE1282638B (de)
FR (1)	FR1505290A (de)
IL (1)	IL27103A (de)

1965
- 1965-12-21 CH CH1759265A patent/CH456571A/de unknown
1966
- 1966-12-20 DE DEG48802A patent/DE1282638B/de active Pending
- 1966-12-20 IL IL2710366A patent/IL27103A/en unknown
- 1966-12-21 FR FR88370A patent/FR1505290A/fr not_active Expired

Also Published As

Publication number	Publication date
FR1505290A (fr)	1967-12-08
CH456571A (de)	1968-07-31
DE1282638B (de)	1968-11-14

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US2969372A (en)	1961-01-24	Cycloalkylpyrazolo [3, 4-alpha] inden-4 [1h]-one derivatives
Johnson et al.	1963	Reactions of Indole. IV. 1 The Synthesis of Some Aminoindoles
JPS6210219B2 (de)	1987-03-05
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