GB920988A - Production of derivatives of 1, 4-bis-(styryl)-benzene - Google Patents
Production of derivatives of 1, 4-bis-(styryl)-benzeneInfo
- Publication number
- GB920988A GB920988A GB2780160A GB2780160A GB920988A GB 920988 A GB920988 A GB 920988A GB 2780160 A GB2780160 A GB 2780160A GB 2780160 A GB2780160 A GB 2780160A GB 920988 A GB920988 A GB 920988A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- benzene
- groups
- free
- hydrogen
- 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
- IJAAWBHHXIWAHM-UHFFFAOYSA-N 1,4-bis(2-phenylethenyl)benzene Chemical class C=1C=CC=CC=1C=CC(C=C1)=CC=C1C=CC1=CC=CC=C1 IJAAWBHHXIWAHM-UHFFFAOYSA-N 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- -1 p-cyanostyryl Chemical group 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- WQLKAHBHPFUKOJ-UHFFFAOYSA-N (2,4-dichlorophenyl)methylphosphonic acid Chemical class OP(O)(=O)CC1=CC=C(Cl)C=C1Cl WQLKAHBHPFUKOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- NGQSLSMAEVWNPU-UHFFFAOYSA-N 1,2-bis(2-phenylethenyl)benzene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1C=CC1=CC=CC=C1 NGQSLSMAEVWNPU-UHFFFAOYSA-N 0.000 abstract 1
- YCXMSKMWUUSLQH-UHFFFAOYSA-N 1,4-bis[2-(4-chlorophenyl)ethenyl]benzene Chemical compound C1=CC(Cl)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(Cl)C=C1 YCXMSKMWUUSLQH-UHFFFAOYSA-N 0.000 abstract 1
- IUAFWEIVTUQPPR-UHFFFAOYSA-N 1,4-bis[2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(OC)C=C1 IUAFWEIVTUQPPR-UHFFFAOYSA-N 0.000 abstract 1
- QEMXVOZFCBVEDQ-UHFFFAOYSA-N 1,4-dichloro-2,5-bis(2-phenylethenyl)benzene Chemical compound ClC=1C=C(C=CC=2C=CC=CC=2)C(Cl)=CC=1C=CC1=CC=CC=C1 QEMXVOZFCBVEDQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 abstract 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 abstract 1
- 229920002521 macromolecule Polymers 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000003223 protective agent Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- 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
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Compounds of the 1,4-bis-(styryl)-benzene series are prepared by reacting a benzylphosphonic acid which is not substituted in paraposition by a free or esterified carboxylic acid group and whose carbon atom attached to the phosphorus atom bears at least one hydrogen atom, or an ester of the same, with a 1,4-diacylbenzene (acyl includes -CHO) in the presence of a proton acceptor. An inert solvent, especially a polar solvent, may be used. The phosphonic compound may be of formula <FORM:0920988/IV(a)/1> where R, R1, R2 and R3 may be hydrogen, aliphatic groups, especially alkyl, halogen, free, esterified or etherified hydroxy, sulphonic acid, sulphonic acid amide, nitrile, carboxylic amide, or, except for R, free or esterified carboxylic groups. R and R1, R and R2 or R and R3 may also be members of 5- or 6-membered cyclic diethers annellated with the benzene ring through the oxygen atoms, the carbon atoms in the ether rings being substituted if desired. R4, R5 and R6 may be hydrogen or aliphatic, especially alkyl, groups; R5 and R6 may also be aryl or may be linked in a ring with the phosphorus. The benzene ring may form part of a naphthalene system. Carboxylic amide groups may be N-substituted, e.g. by C1-6 alkyl or by alkylene completing a ring with the nitrogen. The diacylbenzenes may be of formula <FORM:0920988/IV(a)/2> where R7, R8 and R9 may be hydrogen, or aliphatic or araliphatic, especially alkyl, groups. R7 and R8 may also be halogen, free, etherified or esterified hydroxy, or sulphonic acid groups. The bis-(styryl)-benzenes may be of use as optical bleaches for synthetic and natural macromolecular substances, and as light protective agents, stabilizers, pesticides and dyes. Examples describe the preparation of: 1,4-bis-(31,41-methylenedioxystyryl)benzene; 1,4-bis-(m- and p-cyanostyryl)benzenes; 1,4-bis - (p - methoxystyryl)benzene; 1,4-bis-(31,41-dichlorostyryl)benzene; 1,4-bis(p-chlorostyryl) benzene; 1,4-bis(21,41-dichlorostyryl)benzene; and 1,4-distyryl-2,5-dichlorobenzene. The diethyl esters of the following benzylphosphonic acids are prepared as starting materials from triethyl phosphite and appropriate benzyl halides: 3,4-methylenedioxybenzyl; m- and p-cyanobenzyl; p-methoxy-benzyl; 3,4-dichlorobenzyl; p-chlorobenzyl; and 2,4-dichlorobenzyl phosphonic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB54400A DE1112072B (en) | 1959-08-12 | 1959-08-12 | Process for the preparation of compounds of the 1,4-bis (styryl) -benzene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB920988A true GB920988A (en) | 1963-03-13 |
Family
ID=6970585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2780160A Expired GB920988A (en) | 1959-08-12 | 1960-08-11 | Production of derivatives of 1, 4-bis-(styryl)-benzene |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH389585A (en) |
| DE (1) | DE1112072B (en) |
| GB (1) | GB920988A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163621A (en) * | 1960-10-26 | 1964-12-29 | Basf Ag | Polyamides stabilized with styryl benzenes or stilbenes |
| US4009193A (en) * | 1973-12-22 | 1977-02-22 | Basf Aktiengesellschaft | Bisstyrylaryl compounds |
| US4380514A (en) | 1980-01-12 | 1983-04-19 | Basf Aktiengesellschaft | Preparation of optical brighteners |
| US4785128A (en) * | 1979-12-13 | 1988-11-15 | Ciba-Geigy Corporation | Process for the preparation of bis-styrylbenzenes |
| US4918215A (en) * | 1981-03-31 | 1990-04-17 | Ciba-Geigy Corporation | 4-halogenostilbene derivatives and processes for their preparation |
| US5152922A (en) * | 1986-07-01 | 1992-10-06 | Ciba-Geigy Corporation | 1,4-distyrylbenzene compounds and mixtures thereof with other 1,4-distyrybenzene compounds |
| EP0680947A2 (en) * | 1994-05-02 | 1995-11-08 | Basf Aktiengesellschaft | Process for the preparation of optical brighteners on the basis of stilbenes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2929599A1 (en) * | 1979-07-21 | 1981-02-05 | Hoechst Ag | MIXTURES OF OPTICAL BRIGHTENERS, THEIR PRODUCTION AND USE |
-
1959
- 1959-08-12 DE DEB54400A patent/DE1112072B/en active Pending
-
1960
- 1960-07-25 CH CH847860A patent/CH389585A/en unknown
- 1960-08-11 GB GB2780160A patent/GB920988A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163621A (en) * | 1960-10-26 | 1964-12-29 | Basf Ag | Polyamides stabilized with styryl benzenes or stilbenes |
| US4009193A (en) * | 1973-12-22 | 1977-02-22 | Basf Aktiengesellschaft | Bisstyrylaryl compounds |
| US4785128A (en) * | 1979-12-13 | 1988-11-15 | Ciba-Geigy Corporation | Process for the preparation of bis-styrylbenzenes |
| US4380514A (en) | 1980-01-12 | 1983-04-19 | Basf Aktiengesellschaft | Preparation of optical brighteners |
| EP0032254B1 (en) * | 1980-01-12 | 1984-05-16 | BASF Aktiengesellschaft | Method for the preparation of bis-styrylbenzenes |
| US4464284A (en) * | 1980-01-12 | 1984-08-07 | Basf Aktiengesellschaft | Mixtures of optical brighteners |
| US4918215A (en) * | 1981-03-31 | 1990-04-17 | Ciba-Geigy Corporation | 4-halogenostilbene derivatives and processes for their preparation |
| US5152922A (en) * | 1986-07-01 | 1992-10-06 | Ciba-Geigy Corporation | 1,4-distyrylbenzene compounds and mixtures thereof with other 1,4-distyrybenzene compounds |
| EP0680947A2 (en) * | 1994-05-02 | 1995-11-08 | Basf Aktiengesellschaft | Process for the preparation of optical brighteners on the basis of stilbenes |
| EP0680947A3 (en) * | 1994-05-02 | 1995-11-29 | Basf Ag |
Also Published As
| Publication number | Publication date |
|---|---|
| CH389585A (en) | 1965-03-31 |
| DE1112072B (en) | 1961-08-03 |
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