JPS6055055B2 - Ｐ−オキシ安息香酸エステルの共融混合物の製造方法 - Google Patents
Ｐ−オキシ安息香酸エステルの共融混合物の製造方法Info
- Publication number
- JPS6055055B2 JPS6055055B2 JP56167974A JP16797481A JPS6055055B2 JP S6055055 B2 JPS6055055 B2 JP S6055055B2 JP 56167974 A JP56167974 A JP 56167974A JP 16797481 A JP16797481 A JP 16797481A JP S6055055 B2 JPS6055055 B2 JP S6055055B2
- Authority
- JP
- Japan
- Prior art keywords
- oxybenzoate
- mixture
- alcohol
- ratio
- butyl
- 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
- 239000002253 acid Substances 0.000 title claims description 102
- 239000000374 eutectic mixture Substances 0.000 title claims description 89
- 150000002148 esters Chemical class 0.000 title description 21
- 238000004519 manufacturing process Methods 0.000 title description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 94
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 93
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 56
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 54
- 125000005907 alkyl ester group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 47
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 46
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 42
- 238000010992 reflux Methods 0.000 claims description 40
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000005886 esterification reaction Methods 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 21
- 230000032050 esterification Effects 0.000 claims description 20
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000011065 in-situ storage Methods 0.000 claims description 16
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 7
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims 6
- 230000001502 supplementing effect Effects 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 28
- 239000012153 distilled water Substances 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- 238000004811 liquid chromatography Methods 0.000 description 17
- 239000008346 aqueous phase Substances 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000005496 eutectics Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US199719 | 1980-10-23 | ||
| US06/199,719 US4309564A (en) | 1980-10-23 | 1980-10-23 | Methods for preparing eutectic mixtures of p-hydroxybenzoic acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57122044A JPS57122044A (en) | 1982-07-29 |
| JPS6055055B2 true JPS6055055B2 (ja) | 1985-12-03 |
Family
ID=22738740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56167974A Expired JPS6055055B2 (ja) | 1980-10-23 | 1981-10-22 | Ｐ−オキシ安息香酸エステルの共融混合物の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4309564A (enExample) |
| JP (1) | JPS6055055B2 (enExample) |
| CA (1) | CA1171878A (enExample) |
| DE (1) | DE3141404C2 (enExample) |
| FR (1) | FR2492817A1 (enExample) |
| GB (1) | GB2085879B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357258A (en) * | 1980-10-23 | 1982-11-02 | Mallinckrodt, Inc. | Stable emulsions of p-hydroxybenzoic acid esters and method of preparation |
| JP4845225B2 (ja) | 2008-04-11 | 2011-12-28 | ローム アンド ハース カンパニー | 低融解性殺生物配合物 |
| DE102008054615A1 (de) * | 2008-12-15 | 2010-06-17 | Robert Bosch Gmbh | Verfahren zur Herstellung eines Esters sowie Bindersystem |
| CA2947064A1 (en) * | 2014-05-01 | 2015-11-05 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Simultaneous recovery of organic compounds and extractants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2350326A (en) * | 1941-04-26 | 1944-06-06 | Dow Chemical Co | Condensation product of p-hydroxy benzoic acid |
| US3097131A (en) * | 1959-04-09 | 1963-07-09 | Ueno | Eutectic liquid preservatives |
| US3321509A (en) * | 1964-03-02 | 1967-05-23 | Washine Chemical Corp | Preparation of alkyl esters of parahydroxybenzoic acid |
-
1980
- 1980-10-23 US US06/199,719 patent/US4309564A/en not_active Expired - Lifetime
-
1981
- 1981-09-10 CA CA000385636A patent/CA1171878A/en not_active Expired
- 1981-10-19 DE DE3141404A patent/DE3141404C2/de not_active Expired
- 1981-10-22 FR FR8119837A patent/FR2492817A1/fr active Granted
- 1981-10-22 JP JP56167974A patent/JPS6055055B2/ja not_active Expired
- 1981-10-22 GB GB8131894A patent/GB2085879B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3141404A1 (de) | 1982-06-24 |
| FR2492817A1 (fr) | 1982-04-30 |
| GB2085879B (en) | 1984-04-18 |
| DE3141404C2 (de) | 1985-01-31 |
| JPS57122044A (en) | 1982-07-29 |
| CA1171878A (en) | 1984-07-31 |
| FR2492817B1 (enExample) | 1984-12-28 |
| US4309564A (en) | 1982-01-05 |
| GB2085879A (en) | 1982-05-06 |
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