JPS5817738B2 - ビス（ヒドロキシ−ジ−第三プチル−フエニル）−アルカン酸エステルの製法 - Google Patents
ビス（ヒドロキシ−ジ−第三プチル−フエニル）−アルカン酸エステルの製法Info
- Publication number
- JPS5817738B2 JPS5817738B2 JP50011981A JP1198175A JPS5817738B2 JP S5817738 B2 JPS5817738 B2 JP S5817738B2 JP 50011981 A JP50011981 A JP 50011981A JP 1198175 A JP1198175 A JP 1198175A JP S5817738 B2 JPS5817738 B2 JP S5817738B2
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- phenyl
- hydroxy
- acid
- 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 hydroxy-di-tert-butyl-phenyl Chemical group 0.000 title claims description 20
- 239000002253 acid Substances 0.000 title claims description 17
- 150000002148 esters Chemical class 0.000 title description 5
- 150000005690 diesters Chemical class 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004807 desolvation Methods 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N laevulinic acid Natural products CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- 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
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
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)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7403523 | 1974-02-01 | ||
| FR7403523A FR2259809B1 (en, 2012) | 1974-02-01 | 1974-02-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50116460A JPS50116460A (en, 2012) | 1975-09-11 |
| JPS5817738B2 true JPS5817738B2 (ja) | 1983-04-09 |
Family
ID=9134385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50011981A Expired JPS5817738B2 (ja) | 1974-02-01 | 1975-01-30 | ビス（ヒドロキシ−ジ−第三プチル−フエニル）−アルカン酸エステルの製法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4052364A (en, 2012) |
| JP (1) | JPS5817738B2 (en, 2012) |
| AR (1) | AR205559A1 (en, 2012) |
| AT (1) | AT333737B (en, 2012) |
| BE (1) | BE825116A (en, 2012) |
| BR (1) | BR7500606D0 (en, 2012) |
| CA (1) | CA1053254A (en, 2012) |
| DE (1) | DE2503050A1 (en, 2012) |
| DK (1) | DK34575A (en, 2012) |
| FR (1) | FR2259809B1 (en, 2012) |
| GB (1) | GB1493984A (en, 2012) |
| IE (1) | IE40633B1 (en, 2012) |
| IT (1) | IT1031318B (en, 2012) |
| LU (1) | LU71765A1 (en, 2012) |
| NL (1) | NL7500919A (en, 2012) |
| ZA (1) | ZA75656B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2706937A1 (de) * | 1977-02-18 | 1978-08-24 | Hoechst Ag | Verfahren zur herstellung von bis-(3',5'-di-tert.-butyl-4'-hydroxy- phenyl)-alkylcarbonsaeureestern |
| US4579900A (en) * | 1984-08-31 | 1986-04-01 | Shell Oil Company | Polymeric composition useful for hot water pipe service |
| US4746692A (en) * | 1986-05-05 | 1988-05-24 | Shell Oil Company | Polyolefin compositions for use with water systems |
| DE3940572A1 (de) * | 1989-12-08 | 1991-06-20 | Hoechst Ag | Verfahren zur herstellung eines bis(3,3-bis(4-hydroxy-alkylphenyl)-butansaeure) diolesters |
| US6846866B2 (en) | 2001-06-05 | 2005-01-25 | Invista North America S.A.R.L. | Spandex containing a mixture of phenolic |
| CN113443991A (zh) * | 2020-03-26 | 2021-09-28 | 优禘股份有限公司 | 一种低迁移受阻酚抗氧化合物、制备方法及组合物 |
| CN111689856B (zh) * | 2020-07-17 | 2023-08-22 | 天津利安隆新材料股份有限公司 | 受阻酚类抗氧剂及其中间体的制备方法 |
| CN113603614B (zh) * | 2021-07-09 | 2023-04-07 | 吉林奥来德光电材料股份有限公司 | 一种化合物及其组成的化合物、应用和显示面板 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL271550A (en, 2012) * | 1960-11-25 | |||
| US3206431A (en) * | 1964-09-15 | 1965-09-14 | Shell Oil Co | Thermoplastic polymers containing 3,5-dialkyl-4-hydroxybenzoic acid esters as u.v. stabilizers |
| JPS427789Y1 (en, 2012) * | 1965-02-19 | 1967-04-18 |
-
1974
- 1974-02-01 FR FR7403523A patent/FR2259809B1/fr not_active Expired
-
1975
- 1975-01-25 DE DE19752503050 patent/DE2503050A1/de not_active Withdrawn
- 1975-01-27 NL NL7500919A patent/NL7500919A/xx not_active Application Discontinuation
- 1975-01-30 BR BR606/75A patent/BR7500606D0/pt unknown
- 1975-01-30 US US05/545,532 patent/US4052364A/en not_active Expired - Lifetime
- 1975-01-30 LU LU71765A patent/LU71765A1/xx unknown
- 1975-01-30 JP JP50011981A patent/JPS5817738B2/ja not_active Expired
- 1975-01-30 IT IT19786/75A patent/IT1031318B/it active
- 1975-01-30 GB GB4091/75A patent/GB1493984A/en not_active Expired
- 1975-01-31 DK DK34575*#A patent/DK34575A/da unknown
- 1975-01-31 IE IE196/75A patent/IE40633B1/xx unknown
- 1975-01-31 AT AT74375*#A patent/AT333737B/de not_active IP Right Cessation
- 1975-01-31 ZA ZA00750656A patent/ZA75656B/xx unknown
- 1975-01-31 CA CA219,114A patent/CA1053254A/en not_active Expired
- 1975-02-03 BE BE152999A patent/BE825116A/xx unknown
-
1976
- 1976-05-14 AR AR20555976D patent/AR205559A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA75656B (en) | 1976-01-28 |
| AR205559A1 (es) | 1976-05-14 |
| NL7500919A (nl) | 1975-08-05 |
| ATA74375A (de) | 1976-04-15 |
| LU71765A1 (en, 2012) | 1977-01-27 |
| IE40633L (en) | 1975-08-01 |
| CA1053254A (en) | 1979-04-24 |
| US4052364A (en) | 1977-10-04 |
| FR2259809B1 (en, 2012) | 1978-08-11 |
| BR7500606D0 (pt) | 1975-11-11 |
| IT1031318B (it) | 1979-04-30 |
| AU7775475A (en) | 1976-08-05 |
| BE825116A (nl) | 1975-08-04 |
| DK34575A (en, 2012) | 1975-10-13 |
| JPS50116460A (en, 2012) | 1975-09-11 |
| AT333737B (de) | 1976-12-10 |
| DE2503050A1 (de) | 1975-08-07 |
| FR2259809A1 (en, 2012) | 1975-08-29 |
| IE40633B1 (en) | 1979-07-18 |
| GB1493984A (en) | 1977-12-07 |
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