GB1009484A - Manufacture of aryl esters of aromatic dicarboxylic acids - Google Patents
Manufacture of aryl esters of aromatic dicarboxylic acidsInfo
- Publication number
- GB1009484A GB1009484A GB31475/64A GB3147564A GB1009484A GB 1009484 A GB1009484 A GB 1009484A GB 31475/64 A GB31475/64 A GB 31475/64A GB 3147564 A GB3147564 A GB 3147564A GB 1009484 A GB1009484 A GB 1009484A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- phenol
- ester
- anhydride
- aromatic dicarboxylic
- 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
- -1 aromatic dicarboxylic acids Chemical class 0.000 title abstract 4
- 150000007860 aryl ester derivatives Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 238000005809 transesterification reaction Methods 0.000 abstract 2
- NAQNEMNLLODUCG-UHFFFAOYSA-N 2,3-dichloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1Cl NAQNEMNLLODUCG-UHFFFAOYSA-N 0.000 abstract 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 abstract 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 abstract 1
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 abstract 1
- PLPFTLXIQQYOMW-UHFFFAOYSA-N 5-chlorobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CC(C(O)=O)=C1 PLPFTLXIQQYOMW-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- 229910000410 antimony oxide Inorganic materials 0.000 abstract 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 abstract 1
- PTZZYDVLRWPZNJ-UHFFFAOYSA-N bis(3-methylphenyl) benzene-1,3-dicarboxylate Chemical compound CC1=CC=CC(OC(=O)C=2C=C(C=CC=2)C(=O)OC=2C=C(C)C=CC=2)=C1 PTZZYDVLRWPZNJ-UHFFFAOYSA-N 0.000 abstract 1
- HWZUNHMTOHHEIE-UHFFFAOYSA-N bis(3-methylphenyl) benzene-1,4-dicarboxylate Chemical compound CC1=CC=CC(OC(=O)C=2C=CC(=CC=2)C(=O)OC=2C=C(C)C=CC=2)=C1 HWZUNHMTOHHEIE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 abstract 1
- HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- 150000003739 xylenols Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30618A DE1289532B (de) | 1963-08-03 | 1963-08-03 | Verfahren zur Herstellung einheitlicher Diarylester aromatischer Dicarbonsaeuren |
| DEG0030618 | 1963-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1009484A true GB1009484A (en) | 1965-11-10 |
Family
ID=25969725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31475/64A Expired GB1009484A (en) | 1963-08-03 | 1964-08-04 | Manufacture of aryl esters of aromatic dicarboxylic acids |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3413336A (OSRAM) |
| BE (1) | BE651332A (OSRAM) |
| CH (1) | CH435312A (OSRAM) |
| DE (1) | DE1289532B (OSRAM) |
| GB (1) | GB1009484A (OSRAM) |
| NL (1) | NL6404085A (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2324613A1 (fr) * | 1975-09-18 | 1977-04-15 | Dynamit Nobel Ag | Procede pour l'obtention d'esters benzoiques d'alcools superieurs a partir de fractions contenant du benzoate de methyle de la fabrication du terephtalate de dimethyle |
| US4587054A (en) * | 1982-09-28 | 1986-05-06 | The Procter & Gambel Company | Synthesis of hydrophilic phenol ester derivatives |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3440158A (en) * | 1966-06-30 | 1969-04-22 | Sun Oil Co | Preparation of esters of alpha,alpha'-dimethylmuconic acid |
| US3705186A (en) * | 1968-01-31 | 1972-12-05 | Chemische Werke Witten Gmbh | Process for the preparation of diphenyl terephthalate |
| WO1982000290A1 (en) * | 1980-07-18 | 1982-02-04 | Gen Electric | Process for preparing diphenyl isophthalate and diphenyl terephthalate |
| WO1982000289A1 (en) * | 1980-07-18 | 1982-02-04 | Gen Electric | Process for the preparation of diaryl esters |
| DE3037093C1 (de) * | 1980-10-01 | 1981-11-12 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Cycloocten-4-ol-1 aus Cyclooctadien-1,5 |
| US4482733A (en) * | 1982-09-24 | 1984-11-13 | Occidental Chemical Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| US4451664A (en) * | 1982-09-24 | 1984-05-29 | Occidental Chemical Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| US4482732A (en) * | 1982-09-24 | 1984-11-13 | Occidental Chemical Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| US4737569A (en) * | 1986-12-30 | 1988-04-12 | General Electric Company | Process for the production of substantially monoester-free diaryl esters of aromatic dicarboxylic acids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB314646A (en) * | 1928-05-14 | 1929-07-04 | Consortium Elektrochem Ind | Improvements in the manufacture of esters |
| NL214035A (OSRAM) * | 1956-01-26 |
-
1963
- 1963-08-03 DE DEC30618A patent/DE1289532B/de active Pending
-
1964
- 1964-04-15 NL NL6404085A patent/NL6404085A/xx unknown
- 1964-05-04 CH CH582564A patent/CH435312A/de unknown
- 1964-07-31 US US386728A patent/US3413336A/en not_active Expired - Lifetime
- 1964-08-03 BE BE651332D patent/BE651332A/xx unknown
- 1964-08-04 GB GB31475/64A patent/GB1009484A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2324613A1 (fr) * | 1975-09-18 | 1977-04-15 | Dynamit Nobel Ag | Procede pour l'obtention d'esters benzoiques d'alcools superieurs a partir de fractions contenant du benzoate de methyle de la fabrication du terephtalate de dimethyle |
| US4587054A (en) * | 1982-09-28 | 1986-05-06 | The Procter & Gambel Company | Synthesis of hydrophilic phenol ester derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH435312A (de) | 1967-05-15 |
| BE651332A (OSRAM) | 1964-12-01 |
| US3413336A (en) | 1968-11-26 |
| DE1289532B (de) | 1969-11-20 |
| NL6404085A (OSRAM) | 1965-02-04 |
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