GB929436A - Benzyl phosphoric acid derivatives and improvements in the production of compounds of the 1,4-bis-(para-carboxystyryl)-benzene series - Google Patents
Benzyl phosphoric acid derivatives and improvements in the production of compounds of the 1,4-bis-(para-carboxystyryl)-benzene seriesInfo
- Publication number
- GB929436A GB929436A GB2607760A GB2607760A GB929436A GB 929436 A GB929436 A GB 929436A GB 2607760 A GB2607760 A GB 2607760A GB 2607760 A GB2607760 A GB 2607760A GB 929436 A GB929436 A GB 929436A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzene
- ester
- alkyl
- diethyl ester
- bis
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 3
- HWQRBPRNBFBONX-UHFFFAOYSA-N 4-[2-[4-[2-(4-carboxyphenyl)ethenyl]phenyl]ethenyl]benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(C(O)=O)C=C1 HWQRBPRNBFBONX-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- YTFJQDNGSQJFNA-UHFFFAOYSA-N benzyl dihydrogen phosphate Chemical class OP(O)(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000370 acceptor Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 2
- KEOJOAVYGLGAIM-UHFFFAOYSA-N 1-diethoxyphosphorylbutane Chemical compound CCCCP(=O)(OCC)OCC KEOJOAVYGLGAIM-UHFFFAOYSA-N 0.000 abstract 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 abstract 1
- PXUYTXWZQRKUAV-UHFFFAOYSA-N C(C)OP(OCC)=O.C(=O)(OC)C=1C=CC=CC1C(=O)OC Chemical compound C(C)OP(OCC)=O.C(=O)(OC)C=1C=CC=CC1C(=O)OC PXUYTXWZQRKUAV-UHFFFAOYSA-N 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000005325 alkali earth metal hydroxides Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 238000005282 brightening Methods 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 1
- AGAGZRSHHXLVEK-UHFFFAOYSA-N dimethyl 4-(chloromethyl)benzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(CCl)C=C1C(=O)OC AGAGZRSHHXLVEK-UHFFFAOYSA-N 0.000 abstract 1
- JVFYYXFQXVQDBX-UHFFFAOYSA-N ethyl 4-(diethoxyphosphorylmethyl)-3-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(CP(=O)(OCC)OCC)C(F)=C1 JVFYYXFQXVQDBX-UHFFFAOYSA-N 0.000 abstract 1
- OFUCEQWVGVURAS-UHFFFAOYSA-N ethyl 4-(diethoxyphosphorylmethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CP(=O)(OCC)OCC)C=C1 OFUCEQWVGVURAS-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- FZPWOYLNTQIILA-UHFFFAOYSA-N methyl 2,5-dichloro-4-(diethoxyphosphorylmethyl)benzoate Chemical compound C(C)OP(OCC)(=O)CC1=C(C=C(C(=C1)Cl)C(=O)OC)Cl FZPWOYLNTQIILA-UHFFFAOYSA-N 0.000 abstract 1
- JYRMLIYMFJQZDX-UHFFFAOYSA-N methyl 3-bromo-4-(diethoxyphosphorylmethyl)benzoate Chemical compound CCOP(=O)(OCC)CC1=CC=C(C(=O)OC)C=C1Br JYRMLIYMFJQZDX-UHFFFAOYSA-N 0.000 abstract 1
- SATDLKYRVXFXRE-UHFFFAOYSA-N methyl 4-(chloromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCl)C=C1 SATDLKYRVXFXRE-UHFFFAOYSA-N 0.000 abstract 1
- IGTOJTIOIGZJBM-UHFFFAOYSA-N methyl 4-(dimethoxyphosphorylmethyl)benzoate Chemical compound COC(=O)C1=CC=C(CP(=O)(OC)OC)C=C1 IGTOJTIOIGZJBM-UHFFFAOYSA-N 0.000 abstract 1
- PKAQDUGAIWAFJZ-UHFFFAOYSA-N methyl 4-[2-[4-[2-(4-methoxycarbonylphenyl)ethenyl]phenyl]ethenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(C(=O)OC)C=C1 PKAQDUGAIWAFJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0929436/IV(a)/1> in which R represents hydrogen, an aliphatic or aralkyl radical, the R1 radicals, which may be identical or different, represent hydrogen, alkyl, aryl, halogen, alkoxy or carboxylic ester groups, R11 represents hydrogen or alkyl with one to four carbon atoms, R111 represents hydrogen or alkyl, RIV represents hydrogen or alkyl, or RIII and RIV, when taken together with <FORM:0929436/IV(a)/2> , represent a heterocyclic ring and a process for the production of compounds of the 1,4-bis-(para-carboxystyryl)-benzene series wherein a benzylphosphonic acid, substituted in para-position by a carboxy group, the carbon atom attached to phosphorus of which bears at least one hydrogen atom, or an ester of such an acid, is reacted in the presence of a proton acceptor with a 1,4-diformyl-benzene with the replacement of each of the two carbonyl oxygen atoms in the 1,4-diformyl benzene by a benzal radical. Representative of the benzylphosphonic esters specified for use as starting materials are p-carbethoxybenzyl phosphonic diethyl ester, a -(p-carb-butoxy phenyl) butyl phosphonic diethyl ester, 2,5-dichlor-4-carbmethoxy-benzyl phosphonic diethyl ester, 3-methoxy-, 3-phenyl and 2-brom-4-carbmethoxy benzyl phosphonic diethyl ester and 2-fluor-4-carbethoxy-benzyl-phosphonic acid diethyl ester. Diformyl benzenes specified for use as starting materials include 1,4-diformyl benzene optionally further substituted with alkyl, aralkyl, halogen, alkoxy or sulphonic acid groups. Proton acceptors specified include alkali and alkali earth metal hydroxides, alcoholates and amides, strongly basic amines and ion exchange resins. Many solvents for use in the process are listed. The examples relate to the preparation of 1,4-bis(p-carbmethoxy-styryl)-benzene and 1,4-bis-(31,41-dicarbomethoxy-styryl)-benzene. The products are brightening and light protection agents. p-Carbomethoxy-benzyl phosphonic acid dimethyl ester is obtained by reacting p-chloromethylbenzoic acid methyl ester with triethyl phosphite. 3,4- Dicarbomethoxybenzene phosphonic acid diethyl ester is obtained by heating 3,4-dicarbomethoxybenzyl chloride with triethyl phosphite.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB54219A DE1129947B (en) | 1959-07-29 | 1959-07-29 | Process for the preparation of 1,4-bis (p-carboxystyryl) -benzenes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB929436A true GB929436A (en) | 1963-06-26 |
Family
ID=6970530
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2607760A Expired GB929436A (en) | 1959-07-29 | 1960-07-27 | Benzyl phosphoric acid derivatives and improvements in the production of compounds of the 1,4-bis-(para-carboxystyryl)-benzene series |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE593452A (en) |
CH (1) | CH388294A (en) |
DE (1) | DE1129947B (en) |
GB (1) | GB929436A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51133701A (en) * | 1975-05-16 | 1976-11-19 | Hitachi Ltd | Non-magnetic retainer ring for supporting rotor |
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 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1154617B (en) * | 1960-10-26 | 1963-09-19 | Basf Ag | Stabilized molding compositions containing carbonamide groups |
JPS57150853A (en) * | 1981-03-13 | 1982-09-17 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
US4537985A (en) * | 1982-04-16 | 1985-08-27 | Standard Oil Company (Indiana) | Process for the manufacture of 1,4-bis[2-(4'-carbomethoxystyrenyl)] benzene |
-
1959
- 1959-07-29 DE DEB54219A patent/DE1129947B/en active Pending
-
1960
- 1960-07-07 CH CH775560A patent/CH388294A/en unknown
- 1960-07-27 BE BE593452A patent/BE593452A/en unknown
- 1960-07-27 GB GB2607760A patent/GB929436A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51133701A (en) * | 1975-05-16 | 1976-11-19 | Hitachi Ltd | Non-magnetic retainer ring for supporting rotor |
JPS569225B2 (en) * | 1975-05-16 | 1981-02-27 | ||
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 |
Also Published As
Publication number | Publication date |
---|---|
BE593452A (en) | 1961-01-27 |
CH388294A (en) | 1965-02-28 |
DE1129947B (en) | 1962-05-24 |
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