DE1283849B - Verfahren zur Herstellung von reinen Arylestern von Dicarbonsaeuren - Google Patents
Verfahren zur Herstellung von reinen Arylestern von DicarbonsaeurenInfo
- Publication number
- DE1283849B DE1283849B DEC30667A DEC0030667A DE1283849B DE 1283849 B DE1283849 B DE 1283849B DE C30667 A DEC30667 A DE C30667A DE C0030667 A DEC0030667 A DE C0030667A DE 1283849 B DE1283849 B DE 1283849B
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- alkyl
- parts
- weight
- preparation
- 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
- 150000007860 aryl ester derivatives Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000004780 naphthols Chemical class 0.000 claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims description 3
- 150000002989 phenols Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- -1 aryl carboxylic acid esters Chemical class 0.000 description 4
- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 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
- 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 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940049953 phenylacetate Drugs 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30667A DE1283849B (de) | 1963-08-10 | 1963-08-10 | Verfahren zur Herstellung von reinen Arylestern von Dicarbonsaeuren |
| AT283964A AT244936B (de) | 1963-08-10 | 1964-04-01 | Verfahren zur Herstellung von reinen Arylestern von Di- und Polycarbonsäuren |
| CH463964A CH440316A (de) | 1963-08-10 | 1964-04-09 | Verfahren zur Herstellung von reinen Arylestern von Di- und Polycarbonsäuren |
| NL6406196A NL130840C (OSRAM) | 1963-08-10 | 1964-06-02 | |
| FR981661A FR1400944A (fr) | 1963-08-10 | 1964-07-15 | Procédé de préparation d'esters aryliques purs d'acides di- et polycarboxyliques |
| GB31476/64A GB1009485A (en) | 1963-08-10 | 1964-08-04 | Improvements in or relating to the preparation of esters |
| US387788A US3471549A (en) | 1963-08-10 | 1964-08-05 | Process for the preparation of pure aryl esters of di- and polycarboxylic acids |
| BE651475D BE651475A (OSRAM) | 1963-08-10 | 1964-08-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30667A DE1283849B (de) | 1963-08-10 | 1963-08-10 | Verfahren zur Herstellung von reinen Arylestern von Dicarbonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1283849B true DE1283849B (de) | 1968-11-28 |
Family
ID=7019460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC30667A Pending DE1283849B (de) | 1963-08-10 | 1963-08-10 | Verfahren zur Herstellung von reinen Arylestern von Dicarbonsaeuren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3471549A (OSRAM) |
| AT (1) | AT244936B (OSRAM) |
| BE (1) | BE651475A (OSRAM) |
| CH (1) | CH440316A (OSRAM) |
| DE (1) | DE1283849B (OSRAM) |
| GB (1) | GB1009485A (OSRAM) |
| NL (1) | NL130840C (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0104815A1 (en) * | 1982-09-24 | 1984-04-04 | Celanese Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| EP0104814A1 (en) * | 1982-09-24 | 1984-04-04 | Celanese Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| EP0104813A1 (en) * | 1982-09-24 | 1984-04-04 | Celanese Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN1078582C (zh) * | 1995-12-12 | 2002-01-30 | 宇部兴产株式会社 | 草酸二芳基酯的制备方法 |
| US5731453A (en) * | 1996-03-12 | 1998-03-24 | Ube Industries, Ltd. | Process for producing a diaryl carbonate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH353731A (de) * | 1956-01-26 | 1961-04-30 | Ciba Geigy | Verfahren zur Herstellung von Estern |
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 |
| NL129495C (OSRAM) * | 1963-08-03 |
-
1963
- 1963-08-10 DE DEC30667A patent/DE1283849B/de active Pending
-
1964
- 1964-04-01 AT AT283964A patent/AT244936B/de active
- 1964-04-09 CH CH463964A patent/CH440316A/de unknown
- 1964-06-02 NL NL6406196A patent/NL130840C/xx active
- 1964-08-04 GB GB31476/64A patent/GB1009485A/en not_active Expired
- 1964-08-05 US US387788A patent/US3471549A/en not_active Expired - Lifetime
- 1964-08-06 BE BE651475D patent/BE651475A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH353731A (de) * | 1956-01-26 | 1961-04-30 | Ciba Geigy | Verfahren zur Herstellung von Estern |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0104815A1 (en) * | 1982-09-24 | 1984-04-04 | Celanese Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| EP0104814A1 (en) * | 1982-09-24 | 1984-04-04 | Celanese Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
| EP0104813A1 (en) * | 1982-09-24 | 1984-04-04 | Celanese Corporation | Process of manufacturing diaryl esters of dicarboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| CH440316A (de) | 1967-07-31 |
| GB1009485A (en) | 1965-11-10 |
| NL6406196A (OSRAM) | 1965-02-11 |
| AT244936B (de) | 1966-02-10 |
| NL130840C (OSRAM) | 1970-10-15 |
| US3471549A (en) | 1969-10-07 |
| BE651475A (OSRAM) | 1964-12-01 |
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