US3686266A - Esters of substituted phenoxyphthalic acids - Google Patents
Esters of substituted phenoxyphthalic acids Download PDFInfo
- Publication number
- US3686266A US3686266A US745707A US3686266DA US3686266A US 3686266 A US3686266 A US 3686266A US 745707 A US745707 A US 745707A US 3686266D A US3686266D A US 3686266DA US 3686266 A US3686266 A US 3686266A
- Authority
- US
- United States
- Prior art keywords
- esters
- phenoxyphthalic
- acid
- substituted
- alkali metal
- 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 - Lifetime
Links
- HRMCXDSWURAYFR-UHFFFAOYSA-N 3-phenoxyphthalic acid Chemical class OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1C(O)=O HRMCXDSWURAYFR-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000002148 esters Chemical class 0.000 title description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 8
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 5
- 239000004033 plastic Substances 0.000 abstract description 5
- 229920003023 plastic Polymers 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 150000001340 alkali metals Chemical class 0.000 abstract description 4
- 239000004014 plasticizer Substances 0.000 abstract description 4
- 239000003750 molluscacide Substances 0.000 abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 2
- 239000003495 polar organic solvent Substances 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 alkali metal salts Chemical class 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- MNUOZFHYBCRUOD-UHFFFAOYSA-N 3-hydroxyphthalic acid Chemical class OC(=O)C1=CC=CC(O)=C1C(O)=O MNUOZFHYBCRUOD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002013 molluscicidal effect Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- USFYQEDSCKKGPH-UHFFFAOYSA-N 4-(4-nitrophenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 USFYQEDSCKKGPH-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- PBOFZMZFAKSEEK-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylphthalic acid Chemical compound CC1=CC(C(O)=O)=C(C(O)=O)C(C)=C1O PBOFZMZFAKSEEK-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
- 206010008583 Chloroma Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- JPVQDAGVARKAFY-UHFFFAOYSA-N diethyl 3-hydroxybenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(O)=C1C(=O)OCC JPVQDAGVARKAFY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Definitions
- esters of phenoxyphthalic acid are obtained when alkali metal salts or alkaline earth metal salts of hydroxyphthalic acid esters are reacted in a polar organic solvent, at temperatures of between 50 and 200 C., with derivatives of benzene which are both halogenated and substituted by electrophilic radicals.
- the end products prepared in this way may be used as molluscicides.
- the dimethyl ester of 4'-nitro-4-phenoxy-phthalic acid is particularly suitable for this purpose.
- the product of this invention can be used as plasticizers for polyvinylchloride and similar plastics.
- R and R denote any aliphatic or aromatic hydrocarbon radical which may be the same or different, and they preferably represent alkyl radicals with 1 to 6 carbon atoms. If the alkali metal salts or alkaline earth metal salts of these compounds are used in this invention, the OH group is replaced by MeO, Me denoting an alkali metal or an alkaline earth metal, preferably sodium or potassium. Examples of these compounds are dimethyl 4'hydroxyphthalate, diethyl-3-hydroxyphthalate and their sodium or potassium salts.
- R is preferably an alkyl radical having 1 to 6 carbon atoms or an aryl radical e.g. phenyl and naphthyl.
- the electron attracting radical is defined as a radical which has a s p-value according to the Hammet equation greater than 0.20.
- X is preferably in the por o-position to R
- these compounds are: p-nitrochlorobenzene, o-nitrofluorobenzene, p-cyanochlorobenzene and p- 3,686,266 Patented Aug. 22, 1972 fiuorobenzophenone; chloroand fluoronitrobenzene are particularly suitable.
- phenoxyphthalic acid esters obtained by the process according to the invention are dimethyl 4- nitro-4-phenoxy-phthalate, diethyl 2'-nitro 3 phenoxyphthalate, dimethyl 4'-cyano-4-phenoxy-phthalate and diethyl 4'-benzoyl-4-phenoxy-phthalate.
- Solvents in which the process may be carried out include organic solvents such as dimethylsulphone, dimethylsulphoxide, dimethylformamide and acetonitrile. Dimethylsulphoxide is particularly suitable.
- the process is usually carried out by first reacting a hydroxyphthalic acid ester, dissolved in an inert organic solvent such as toluene or benzene, with an aqueous alkali metal hydroxide or an alkali metal alcoholate or an alkali metal to form the corresponding alkali metal salt.
- alkali metal compounds alkaline earth metal compounds may be used. Preferably, sodium or sodium compounds are used.
- the resulting alkali metal salt or alkaline earth metal salt of the hydroxyphthalic acid ester is then reacted with the halogenated benzene in one of the aforesaid polar solvents.
- This reaction is generally carried out at 50 to 200 C.
- This stage is preferably carried out with the complete exclusion of water.
- the water formed during the reaction is distilled off azeotropically together with the organic solvent which is then returned to the reaction system after removal of the water.
- the completion of the reaction can be detected by the neutral reaction of the reaction mixture.
- the end products can be isolated from this mixture by removal, for example from the alkali metal halide or alkaline earth metal halide formed in the reaction, by filtration. The remaining solution can then be concentrated by evaporation.
- the end products prepared in this way may be used as molluscicides.
- the dimethyl ester of 4'-nitro-4-phen0xyphthalic acid is particularly suitable for this purpose.
- the products of this invention can also be used as plasticizers for polyvinylchloride and similar plastics. They may be incorporated e.g. on a crew extruder as is usual with incorporating additives in plastics and may be used in amounts of from 5 to 50% by weight, preferably 10 to 20% by weight. These additives exert the same plasticizing effect as normally used phthalic acid esters. Their main advantage is in the fact that the substituent on the aromatic nucleus reduces their migration so that plastics which contain the products of this invention as plasticizers especially polyvinylchloride will not give off these additives in the course of time.
- the instant compounds are also intermediates for producing coating materials, such as lacquers and films, resistant to high temperatures, as disclosed and claimed in copending US. application Ser. No. 745,401, filed July 17, 1968, now Pat. No. 3,503,928.
- the dimethyl ester of 4-amino-4-phenoxyphthalic acid is saponified in a methanolic solution of potassium hydroxide under refiux in an atomsphere of nitrogen.
- the hydrochloride of 4'-amino-4-phenoxyphthalic acid is prepared by introducing the methanolic solution dropwise into a mixture of 50% water and 50% concentrated hydrochloric acid, and it is then recrystallised from water. 5 g. of the hydrochloride of 4'-amino-4-phenoxyphthalic acid are suspended in purified thionyl chloride at room temperature and stirred until no further evolution of gas can be observed (6 to 8 hours).
- the thionyl chloride is re moved by evaporation and the chloride of 4'ammonium- 4-phenoxy-phthalic acid anhydride remaining behind is dissolved in 25 ml. of anhydrous pyridine without further purification and stirred for 4 hours at 25 C.
- a viscous solution is obtained which is divided into two halves. One half is poured on a glass plate and heated under nitrogen, first at 150 C. for one hour and then at 300 C. for 30 minutes. The resulting film can withstand temperatures above 400 C. without visible damage.
- the second half of the solution is introduced dropwise into dilute acetic acid and the resulting precipitate of polyamidocarboxylic acid is filtered off, washed with methanol and water and dried under vacuum.
- the product can be stored for some time in this form.
- 1 g. of the polyamidocarboxylic acid is dissolved in 4 ml. of dimethyl formamide and converted as described above into a polyimide film which has the same properties.
- Heat distortion temperature 560 C.
- Example 1 was repeated using a solution of 4.0 g. (0.1 mol) of sodium hydroxide in 10 ml. of water in place of the sodium methylate. The water was distilled off azeotropically with toluene, and the solution of p-chlorom'trobenzene was then added. Yield: 25 g.
- R* is alkyl of 1 to 6 carbon atoms, phenyl or naphthyl.
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 |
|---|---|---|---|
| DEF0053060 | 1967-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3686266A true US3686266A (en) | 1972-08-22 |
Family
ID=7105965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US745707A Expired - Lifetime US3686266A (en) | 1967-07-26 | 1968-07-18 | Esters of substituted phenoxyphthalic acids |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3686266A (forum.php) |
| BE (1) | BE718564A (forum.php) |
| CH (1) | CH499483A (forum.php) |
| DE (1) | DE1643333A1 (forum.php) |
| FR (1) | FR1573736A (forum.php) |
| GB (1) | GB1202166A (forum.php) |
| NL (1) | NL6810545A (forum.php) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873593A (en) * | 1971-01-20 | 1975-03-25 | Gen Electric | Process for making aryloxy compositions |
| US3884955A (en) * | 1972-01-17 | 1975-05-20 | Ciba Geigy Corp | Process for the manufacture of substituted O-cyanobenzoic acid esters |
| US4395570A (en) * | 1981-11-16 | 1983-07-26 | Rohm And Haas Company | Preparation of 5-(2-halo-4-trifluoromethylphenoxy)-2-nitrobenzoic acid and salts and esters and amides |
-
1967
- 1967-07-26 DE DE19671643333 patent/DE1643333A1/de active Pending
-
1968
- 1968-04-18 CH CH575068A patent/CH499483A/de not_active IP Right Cessation
- 1968-06-13 GB GB28091/68A patent/GB1202166A/en not_active Expired
- 1968-07-18 US US745707A patent/US3686266A/en not_active Expired - Lifetime
- 1968-07-25 BE BE718564D patent/BE718564A/xx unknown
- 1968-07-25 NL NL6810545A patent/NL6810545A/xx unknown
- 1968-07-26 FR FR1573736D patent/FR1573736A/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873593A (en) * | 1971-01-20 | 1975-03-25 | Gen Electric | Process for making aryloxy compositions |
| US3884955A (en) * | 1972-01-17 | 1975-05-20 | Ciba Geigy Corp | Process for the manufacture of substituted O-cyanobenzoic acid esters |
| US4395570A (en) * | 1981-11-16 | 1983-07-26 | Rohm And Haas Company | Preparation of 5-(2-halo-4-trifluoromethylphenoxy)-2-nitrobenzoic acid and salts and esters and amides |
Also Published As
| Publication number | Publication date |
|---|---|
| CH499483A (de) | 1970-11-30 |
| DE1643333A1 (de) | 1971-03-25 |
| BE718564A (forum.php) | 1968-12-31 |
| NL6810545A (forum.php) | 1969-01-28 |
| GB1202166A (en) | 1970-08-12 |
| FR1573736A (forum.php) | 1969-07-04 |
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