CA1171878A - Methods for preparing eutectic mixtures of p- hydroxybenzoic acid esters - Google Patents
Methods for preparing eutectic mixtures of p- hydroxybenzoic acid estersInfo
- Publication number
- CA1171878A CA1171878A CA000385636A CA385636A CA1171878A CA 1171878 A CA1171878 A CA 1171878A CA 000385636 A CA000385636 A CA 000385636A CA 385636 A CA385636 A CA 385636A CA 1171878 A CA1171878 A CA 1171878A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxybenzoate
- mixture
- butyl
- isopropyl
- alcohol
- 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
- 239000000374 eutectic mixture Substances 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 48
- 150000005168 4-hydroxybenzoic acids Chemical class 0.000 title abstract description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 198
- 239000000203 mixture Substances 0.000 claims abstract description 104
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims abstract description 99
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 230000032050 esterification Effects 0.000 claims abstract description 27
- 238000005886 esterification reaction Methods 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 238000011065 in-situ storage Methods 0.000 claims abstract description 21
- 238000010791 quenching Methods 0.000 claims abstract description 16
- 230000000171 quenching effect Effects 0.000 claims abstract description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 90
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 81
- CMHMMKSPYOOVGI-UHFFFAOYSA-N Isopropylparaben Chemical compound CC(C)OC(=O)C1=CC=C(O)C=C1 CMHMMKSPYOOVGI-UHFFFAOYSA-N 0.000 claims description 55
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 51
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 46
- XPJVKCRENWUEJH-UHFFFAOYSA-N Isobutylparaben Chemical compound CC(C)COC(=O)C1=CC=C(O)C=C1 XPJVKCRENWUEJH-UHFFFAOYSA-N 0.000 claims description 45
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 claims description 44
- 238000010992 reflux Methods 0.000 claims description 39
- 229960004592 isopropanol Drugs 0.000 claims description 30
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 23
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 18
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 230000005496 eutectics Effects 0.000 claims description 10
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 5
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000306 component Substances 0.000 claims 3
- 230000002730 additional effect Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 18
- 238000002156 mixing Methods 0.000 abstract description 4
- 230000008018 melting Effects 0.000 abstract description 2
- 238000002844 melting Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- 238000004811 liquid chromatography Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 229940083608 sodium hydroxide Drugs 0.000 description 10
- 229940032330 sulfuric acid Drugs 0.000 description 9
- 238000004821 distillation Methods 0.000 description 7
- -1 amyl alcohols Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- ZUOTXZHOGPQFIU-UHFFFAOYSA-N butan-2-yl 4-hydroxybenzoate Chemical compound CCC(C)OC(=O)C1=CC=C(O)C=C1 ZUOTXZHOGPQFIU-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005809 transesterification reaction 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
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- ZNSSPLQZSUWFJT-UHFFFAOYSA-N pentyl 4-hydroxybenzoate Chemical compound CCCCCOC(=O)C1=CC=C(O)C=C1 ZNSSPLQZSUWFJT-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229940123150 Chelating agent Drugs 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ZLVSYODPTJZFMK-UHFFFAOYSA-M sodium 4-hydroxybenzoate Chemical compound [Na+].OC1=CC=C(C([O-])=O)C=C1 ZLVSYODPTJZFMK-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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 |
|---|---|---|---|
| US199,719 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1171878A true CA1171878A (en) | 1984-07-31 |
Family
ID=22738740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000385636A Expired CA1171878A (en) | 1980-10-23 | 1981-09-10 | Methods for preparing eutectic mixtures of p- hydroxybenzoic acid esters |
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 |
| FR2492817B1 (enExample) | 1984-12-28 |
| US4309564A (en) | 1982-01-05 |
| JPS6055055B2 (ja) | 1985-12-03 |
| GB2085879A (en) | 1982-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |