GB975355A - Production of neutral terephthalic acid esters - Google Patents
Production of neutral terephthalic acid estersInfo
- Publication number
- GB975355A GB975355A GB10743/63A GB1074363A GB975355A GB 975355 A GB975355 A GB 975355A GB 10743/63 A GB10743/63 A GB 10743/63A GB 1074363 A GB1074363 A GB 1074363A GB 975355 A GB975355 A GB 975355A
- Authority
- GB
- United Kingdom
- Prior art keywords
- terephthalate
- acid
- neutral
- salt
- anhydride
- 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
- 230000007935 neutral effect Effects 0.000 title abstract 7
- 150000003503 terephthalic acid derivatives Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 4
- 230000032050 esterification Effects 0.000 abstract 4
- 238000005886 esterification reaction Methods 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- LRUDDHYVRFQYCN-UHFFFAOYSA-L dipotassium;terephthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 LRUDDHYVRFQYCN-UHFFFAOYSA-L 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 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
- 150000002148 esters Chemical class 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- BPWIVQHIJYRBSR-UHFFFAOYSA-M potassium;hydron;terephthalate Chemical compound [K+].OC(=O)C1=CC=C(C([O-])=O)C=C1 BPWIVQHIJYRBSR-UHFFFAOYSA-M 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 2
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 1
- MCQXGKSTPTWGSF-UHFFFAOYSA-N cadmium;terephthalic acid Chemical compound [Cd].OC(=O)C1=CC=C(C(O)=O)C=C1 MCQXGKSTPTWGSF-UHFFFAOYSA-N 0.000 abstract 1
- AAEHPKIXIIACPQ-UHFFFAOYSA-L calcium;terephthalate Chemical compound [Ca+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 AAEHPKIXIIACPQ-UHFFFAOYSA-L 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000011437 continuous method Methods 0.000 abstract 1
- FFPQSNUAVYJZDH-UHFFFAOYSA-N diazanium;terephthalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 FFPQSNUAVYJZDH-UHFFFAOYSA-N 0.000 abstract 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB66488A DE1155112B (de) | 1962-03-23 | 1962-03-23 | Verfahren zur Herstellung von Terephthalsaeureestern |
| DEB69029A DE1195289B (de) | 1962-09-29 | 1962-09-29 | Verfahren zur Herstellung von Terephthalsaeuremonoglykolester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB975355A true GB975355A (en) | 1964-11-18 |
Family
ID=25966199
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10743/63A Expired GB975355A (en) | 1962-03-23 | 1963-03-19 | Production of neutral terephthalic acid esters |
| GB37474/63A Expired GB977727A (en) | 1962-03-23 | 1963-09-24 | Production of monoglycol terephthalate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37474/63A Expired GB977727A (en) | 1962-03-23 | 1963-09-24 | Production of monoglycol terephthalate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3320303A (en, 2012) |
| AT (1) | AT243253B (en, 2012) |
| BE (2) | BE629973A (en, 2012) |
| CH (2) | CH421073A (en, 2012) |
| DE (1) | DE1155112B (en, 2012) |
| GB (2) | GB975355A (en, 2012) |
| NL (2) | NL290433A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6818160B2 (en) | 2000-11-16 | 2004-11-16 | E. I. Du Pont De Nemours And Company | Method to improve properties of poly(trimethylene terephthalate) film |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935238A (en) * | 1973-01-15 | 1976-01-27 | Sun Research And Development Co. | Preparation of phthalate esters |
| US3954840A (en) * | 1973-02-14 | 1976-05-04 | Teijin Ltd. | 1,3,5,7-Naphthalenetetracarboxylic acids and process for preparation thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1081877B (de) | 1955-12-09 | 1960-05-19 | Basf Ag | Verfahren zur Abscheidung von cyclischen Dicarbonsaeuren |
| US2841615A (en) * | 1956-01-05 | 1958-07-01 | Henkel & Cie Gmbh | Process for the recovery of terephthalic acid from solutions containing alkali metal salts of terephthalic acid |
| DE1063593B (de) | 1956-01-05 | 1959-08-20 | Henkel & Cie Gmbh | Verfahren zur UEberfuehrung von Dialkaliterephthalaten, die durch thermische Umlagerung von Salzen anderer Benzolcarbonsaeure erhalten worden sind, in Terephthalsaeure |
-
0
- BE BE637948D patent/BE637948A/xx unknown
- NL NL297999D patent/NL297999A/xx unknown
- NL NL290433D patent/NL290433A/xx unknown
- BE BE629973D patent/BE629973A/xx unknown
-
1962
- 1962-03-23 DE DEB66488A patent/DE1155112B/de active Pending
-
1963
- 1963-03-14 CH CH324863A patent/CH421073A/de unknown
- 1963-03-19 US US266208A patent/US3320303A/en not_active Expired - Lifetime
- 1963-03-19 GB GB10743/63A patent/GB975355A/en not_active Expired
- 1963-09-11 CH CH1123163A patent/CH419088A/de unknown
- 1963-09-24 GB GB37474/63A patent/GB977727A/en not_active Expired
- 1963-09-27 AT AT779163A patent/AT243253B/de active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6818160B2 (en) | 2000-11-16 | 2004-11-16 | E. I. Du Pont De Nemours And Company | Method to improve properties of poly(trimethylene terephthalate) film |
Also Published As
| Publication number | Publication date |
|---|---|
| CH421073A (de) | 1966-09-30 |
| NL290433A (en, 2012) | |
| US3320303A (en) | 1967-05-16 |
| DE1155112B (de) | 1963-10-03 |
| AT243253B (de) | 1965-11-10 |
| BE629973A (en, 2012) | |
| GB977727A (en) | 1964-12-09 |
| NL297999A (en, 2012) | |
| BE637948A (en, 2012) | |
| CH419088A (de) | 1966-08-31 |
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