DE2064944A1 - Neue p-Sulfophenoxymalonate. Ausscheidung aus: 2043046 - Google Patents
Neue p-Sulfophenoxymalonate. Ausscheidung aus: 2043046Info
- Publication number
- DE2064944A1 DE2064944A1 DE19702064944 DE2064944A DE2064944A1 DE 2064944 A1 DE2064944 A1 DE 2064944A1 DE 19702064944 DE19702064944 DE 19702064944 DE 2064944 A DE2064944 A DE 2064944A DE 2064944 A1 DE2064944 A1 DE 2064944A1
- Authority
- DE
- Germany
- Prior art keywords
- malonate
- methyl
- sulfophenoxy
- salt
- carbon atoms
- 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.)
- Pending
Links
- QXPAUZHNJMFPEG-UHFFFAOYSA-N OC(C(C(O)=O)OC(C=C1)=CC=C1S(O)(=O)=O)=O Chemical class OC(C(C(O)=O)OC(C=C1)=CC=C1S(O)(=O)=O)=O QXPAUZHNJMFPEG-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 9
- 229920001634 Copolyester Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 5
- -1 aliphatic glycols Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FJDJALCDARBKLM-UHFFFAOYSA-N 2-phenoxy-2-sulfopropanedioic acid Chemical class OC(=O)C(S(O)(=O)=O)(C(O)=O)OC1=CC=CC=C1 FJDJALCDARBKLM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SXIZBNZXRTYSBL-UHFFFAOYSA-N CCCOC(=O)C(Cl)C(=O)OCCC Chemical compound CCCOC(=O)C(Cl)C(=O)OCCC SXIZBNZXRTYSBL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 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
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VBPRCPAJVAYMNK-UHFFFAOYSA-N dibutyl 2-propylpropanedioate Chemical compound CCCCOC(=O)C(CCC)C(=O)OCCCC VBPRCPAJVAYMNK-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- CSLQAXTUGPUBCW-UHFFFAOYSA-N diethyl 2-bromo-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(Br)C(=O)OCC CSLQAXTUGPUBCW-UHFFFAOYSA-N 0.000 description 1
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
- KZLOHBHRWOICLP-UHFFFAOYSA-N dimethyl 2-bromo-2-ethylpropanedioate Chemical compound COC(=O)C(Br)(CC)C(=O)OC KZLOHBHRWOICLP-UHFFFAOYSA-N 0.000 description 1
- YQTLPVHRPGZEJE-UHFFFAOYSA-N dimethyl 2-bromo-2-methylpropanedioate Chemical compound COC(=O)C(C)(Br)C(=O)OC YQTLPVHRPGZEJE-UHFFFAOYSA-N 0.000 description 1
- NEMOJKROKMMQBQ-UHFFFAOYSA-N dimethyl 2-bromopropanedioate Chemical compound COC(=O)C(Br)C(=O)OC NEMOJKROKMMQBQ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XDDDDXAGOCDWDL-UHFFFAOYSA-L disodium;4-oxidobenzenesulfonate Chemical compound [Na+].[Na+].[O-]C1=CC=C(S([O-])(=O)=O)C=C1 XDDDDXAGOCDWDL-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86737569A | 1969-10-17 | 1969-10-17 | |
| US3783870A | 1970-05-15 | 1970-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2064944A1 true DE2064944A1 (de) | 1971-11-18 |
Family
ID=26714542
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702064944 Pending DE2064944A1 (de) | 1969-10-17 | 1970-08-31 | Neue p-Sulfophenoxymalonate. Ausscheidung aus: 2043046 |
| DE19702043046 Pending DE2043046A1 (enExample) | 1969-10-17 | 1970-08-31 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702043046 Pending DE2043046A1 (enExample) | 1969-10-17 | 1970-08-31 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4935259B1 (enExample) |
| DE (2) | DE2064944A1 (enExample) |
| ES (2) | ES384352A1 (enExample) |
| FR (1) | FR2064385B1 (enExample) |
| GB (1) | GB1324811A (enExample) |
-
1970
- 1970-07-28 GB GB3656670A patent/GB1324811A/en not_active Expired
- 1970-08-31 DE DE19702064944 patent/DE2064944A1/de active Pending
- 1970-08-31 DE DE19702043046 patent/DE2043046A1/de active Pending
- 1970-09-23 FR FR7034515A patent/FR2064385B1/fr not_active Expired
- 1970-10-03 JP JP8655370A patent/JPS4935259B1/ja active Pending
- 1970-10-09 ES ES384352A patent/ES384352A1/es not_active Expired
- 1970-10-09 ES ES384353A patent/ES384353A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES384353A1 (es) | 1973-02-16 |
| JPS4935259B1 (enExample) | 1974-09-20 |
| ES384352A1 (es) | 1973-02-16 |
| FR2064385A1 (enExample) | 1971-07-23 |
| DE2043046A1 (enExample) | 1971-06-09 |
| GB1324811A (en) | 1973-07-25 |
| FR2064385B1 (enExample) | 1974-03-22 |
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