CH632734A5 - Process for the preparation of bis-(3',5'-di-tert.-butyl-4'-hydroxy-phenyl)-alkylcarboxylic acid esters - Google Patents

Process for the preparation of bis-(3',5'-di-tert.-butyl-4'-hydroxy-phenyl)-alkylcarboxylic acid esters Download PDF

Info

Publication number: CH632734A5
Authority: CH; Switzerland
Prior art keywords: bis; tert; butyl; acid esters; hydroxy
Prior art date: 1977-02-18

Application number

CH166078A

Other languages

German (de)

English (en)

Inventor

Norbert Dr Mayer

Hartmut Dr Wiezer

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1977-02-18

Filing date

1978-02-15

Publication date

1982-10-29

1978-02-15 Application filed by Hoechst Ag filed Critical Hoechst Ag

1982-10-29 Publication of CH632734A5 publication Critical patent/CH632734A5/de

Links

238000000034 method Methods 0.000 title claims description 15
150000002148 esters Chemical class 0.000 title claims description 10
239000002253 acid Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 5
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 20
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 11
239000000047 product Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
238000005804 alkylation reaction Methods 0.000 claims description 6
-1 alkyl carboxylic acid esters Chemical class 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
238000004140 cleaning Methods 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000012043 crude product Substances 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
125000005910 alkyl carbonate group Chemical group 0.000 claims 2
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims 1
239000004215 Carbon black (E152) Substances 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
150000001733 carboxylic acid esters Chemical class 0.000 claims 1
238000004440 column chromatography Methods 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
238000011005 laboratory method Methods 0.000 claims 1
239000005011 phenolic resin Substances 0.000 claims 1
229920001568 phenolic resin Polymers 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
YMWSWQXYQSMSAU-UHFFFAOYSA-N 3,3-bis(3,5-ditert-butyl-4-hydroxyphenyl)butanoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(C)(CC(O)=O)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 YMWSWQXYQSMSAU-UHFFFAOYSA-N 0.000 description 1
RXZAPQOBZRGPGZ-UHFFFAOYSA-N CCCCCCCCOC(=O)CC(C)(C1=CC(=C(C=C1)O)C(C)(C)C)C2=CC(=C(C=C2)O)C(C)(C)C Chemical compound CCCCCCCCOC(=O)CC(C)(C1=CC(=C(C=C1)O)C(C)(C)C)C2=CC(=C(C=C2)O)C(C)(C)C RXZAPQOBZRGPGZ-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
UNEPLCDONLXLBE-UHFFFAOYSA-N butyl 3,3-bis(3,5-ditert-butyl-4-hydroxyphenyl)butanoate Chemical compound C(CCC)OC(CC(C)(C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=O UNEPLCDONLXLBE-UHFFFAOYSA-N 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
JDRVJRJCGGEVSN-UHFFFAOYSA-N ethyl 3,3-bis(3,5-ditert-butyl-4-hydroxyphenyl)butanoate Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1C(C)(CC(=O)OCC)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JDRVJRJCGGEVSN-UHFFFAOYSA-N 0.000 description 1
GYMIENTWMRYMLE-UHFFFAOYSA-N ethyl 3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoate Chemical compound C=1C=C(O)C(C(C)(C)C)=CC=1C(C)(CC(=O)OCC)C1=CC=C(O)C(C(C)(C)C)=C1 GYMIENTWMRYMLE-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AVVPOKSKJSJVIX-UHFFFAOYSA-N methyl 5-oxohexanoate Chemical compound COC(=O)CCCC(C)=O AVVPOKSKJSJVIX-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
LCPRAKOLISTCFN-UHFFFAOYSA-N octadecyl 3,3-bis(3,5-ditert-butyl-4-hydroxyphenyl)butanoate Chemical compound C(CCCCCCCCCCCCCCCCC)OC(CC(C)(C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=O LCPRAKOLISTCFN-UHFFFAOYSA-N 0.000 description 1
GDLVIJQMWGDXFW-UHFFFAOYSA-N octadecyl 3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoate Chemical compound C(CCCCCCCCCCCCCCCCC)OC(CC(C)(C1=CC(=C(C=C1)O)C(C)(C)C)C1=CC(=C(C=C1)O)C(C)(C)C)=O GDLVIJQMWGDXFW-UHFFFAOYSA-N 0.000 description 1
NMSGDNYFQNBMIZ-UHFFFAOYSA-N octyl 3,3-bis(3,5-ditert-butyl-4-hydroxyphenyl)butanoate Chemical compound C(CCCCCCC)OC(CC(C)(C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=O NMSGDNYFQNBMIZ-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000008096 xylene Substances 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
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH166078A 1977-02-18 1978-02-15 Process for the preparation of bis-(3',5'-di-tert.-butyl-4'-hydroxy-phenyl)-alkylcarboxylic acid esters CH632734A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772706937 DE2706937A1 (de)	1977-02-18	1977-02-18	Verfahren zur herstellung von bis-(3',5'-di-tert.-butyl-4'-hydroxy- phenyl)-alkylcarbonsaeureestern

Publications (1)

Publication Number	Publication Date
CH632734A5 true CH632734A5 (en)	1982-10-29

Family

ID=6001527

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH166078A CH632734A5 (en)	1977-02-18	1978-02-15	Process for the preparation of bis-(3',5'-di-tert.-butyl-4'-hydroxy-phenyl)-alkylcarboxylic acid esters

Country Status (5)

Country	Link
BE (1)	BE864113A (it)
CH (1)	CH632734A5 (it)
DE (1)	DE2706937A1 (it)
FR (1)	FR2381019A1 (it)
IT (1)	IT1095357B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4267358A (en) *	1980-03-13	1981-05-12	Borg-Warner Corporation	Phenolic ester inhibitor
DE4015541A1 (de) *	1990-05-15	1991-11-21	Bayer Ag	Tert.-alkylester-bisphenole, verfahren zu ihrer herstellung und ihre verwendung
US7727944B2 (en)	2004-08-18	2010-06-01	The Lubrizol Corporation	Lubricant compositions containing seal conditioning agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE757796A (fr)	1969-10-23	1971-04-21	Hoechst Ag	Procede de preparation de produits de condensation de phenols et d'esters aceto-acetiques
FR2259809B1 (it) *	1974-02-01	1978-08-11	Nobel Hoechst Chimie
DE2615764C3 (de) *	1976-04-10	1979-07-05	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Bis-(3'3'-di-tert-butyl-4'-hvdroxyphenyO-alkansäurediestern

1977
- 1977-02-18 DE DE19772706937 patent/DE2706937A1/de not_active Withdrawn
1978
- 1978-02-15 CH CH166078A patent/CH632734A5/de not_active IP Right Cessation
- 1978-02-16 IT IT20346/78A patent/IT1095357B/it active
- 1978-02-20 BE BE185298A patent/BE864113A/xx not_active IP Right Cessation
- 1978-02-20 FR FR7804706A patent/FR2381019A1/fr active Pending

Also Published As

Publication number	Publication date
IT7820346A0 (it)	1978-02-16
FR2381019A1 (fr)	1978-09-15
BE864113A (fr)	1978-08-21
DE2706937A1 (de)	1978-08-24
IT1095357B (it)	1985-08-10

Legal Events

Date	Code	Title	Description
1984-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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