NO135467B - - Google Patents
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- Publication number
- NO135467B NO135467B NO4193/69A NO419369A NO135467B NO 135467 B NO135467 B NO 135467B NO 4193/69 A NO4193/69 A NO 4193/69A NO 419369 A NO419369 A NO 419369A NO 135467 B NO135467 B NO 135467B
- Authority
- NO
- Norway
- Prior art keywords
- salicylic acid
- aluminum
- water
- alcoholate
- solvent
- Prior art date
Links
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 92
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 46
- 229960004889 salicylic acid Drugs 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 229910052782 aluminium Inorganic materials 0.000 claims description 37
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 13
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 7
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 5
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000002035 prolonged effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 27
- 239000000126 substance Substances 0.000 description 24
- 238000003756 stirring Methods 0.000 description 12
- 229940068372 acetyl salicylate Drugs 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- WUBBRNOQWQTFEX-UHFFFAOYSA-M 4-aminosalicylate(1-) Chemical compound NC1=CC=C(C([O-])=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- -1 hydroxyl compound Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940024546 aluminum hydroxide gel Drugs 0.000 description 2
- SMYKVLBUSSNXMV-UHFFFAOYSA-K aluminum;trihydroxide;hydrate Chemical compound O.[OH-].[OH-].[OH-].[Al+3] SMYKVLBUSSNXMV-UHFFFAOYSA-K 0.000 description 2
- 229940069428 antacid Drugs 0.000 description 2
- 239000003159 antacid agent Substances 0.000 description 2
- 230000001458 anti-acid effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 2
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229940024545 aluminum hydroxide Drugs 0.000 description 1
- GKJRJGXKDYCFNF-UHFFFAOYSA-K aluminum;2-acetyloxybenzoate Chemical compound [Al+3].CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC1=CC=CC=C1C([O-])=O GKJRJGXKDYCFNF-UHFFFAOYSA-K 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
- WHOPEPSOPUIRQQ-UHFFFAOYSA-N oxoaluminum Chemical compound O1[Al]O[Al]1 WHOPEPSOPUIRQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JZLOKWGVGHYBKD-UHFFFAOYSA-M sodium;2-acetyloxybenzoate Chemical compound [Na+].CC(=O)OC1=CC=CC=C1C([O-])=O JZLOKWGVGHYBKD-UHFFFAOYSA-M 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
- C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/843,028 US4058555A (en) | 1969-07-18 | 1969-07-18 | Process for the purification of mixed acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135467B true NO135467B (Direct) | 1977-01-03 |
| NO135467C NO135467C (Direct) | 1977-04-13 |
Family
ID=25288880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4193/69A NO135467C (Direct) | 1969-07-18 | 1969-10-22 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4058555A (Direct) |
| JP (1) | JPS4914204B1 (Direct) |
| AT (1) | AT301578B (Direct) |
| BE (1) | BE741803A (Direct) |
| BR (1) | BR7016945D0 (Direct) |
| CH (1) | CH526504A (Direct) |
| DE (1) | DE2001100C2 (Direct) |
| ES (1) | ES373890A1 (Direct) |
| FR (1) | FR2051826B1 (Direct) |
| GB (1) | GB1282927A (Direct) |
| IE (1) | IE33335B1 (Direct) |
| LU (1) | LU59826A1 (Direct) |
| NL (1) | NL6916083A (Direct) |
| NO (1) | NO135467C (Direct) |
| SE (1) | SE368390B (Direct) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4192399A (en) * | 1976-03-12 | 1980-03-11 | Dana Corporation | Safety vacuum valve and electric switch for speed control systems |
| US4339596A (en) * | 1979-11-15 | 1982-07-13 | El Paso Products Company | Treatment of byproduct stream from adipic acid manufacture |
| WO1997047579A1 (en) * | 1996-06-10 | 1997-12-18 | Renewable Energy Development Corporation | Methods for synthesis of high purity carboxylic and fatty acids |
| GB0325530D0 (en) * | 2003-10-31 | 2003-12-03 | Davy Process Techn Ltd | Process |
| EP2720997A1 (en) | 2011-06-17 | 2014-04-23 | Invista Technologies S.à.r.l. | Use of hydrolases to increase monomer content in waste stream |
| CN104011216A (zh) | 2011-06-30 | 2014-08-27 | 英威达技术有限责任公司 | 用于生产尼龙-7、尼龙-7,7和聚酯的生物转化工艺 |
| US9102958B2 (en) | 2011-12-16 | 2015-08-11 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage |
| US9102960B2 (en) | 2011-12-16 | 2015-08-11 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage |
| WO2014093847A2 (en) | 2012-12-14 | 2014-06-19 | Invista North America S.A.R.L. | METHODS OF PRODUCING 7-CARBON CHEMICALS VIA CoA-DEPENDENT CARBON CHAIN ELONGATION ASSOCIATED WITH CARBON STORAGE |
| EP2938731A2 (en) | 2012-12-31 | 2015-11-04 | Invista Technologies S.A R.L. | Methods of producing 7-carbon chemicals via carbon chain elongation associated with cyclohexane carboxylate synthesis |
| WO2014105797A2 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via pyruvate and succinate semialdehyde aldol condensation |
| CN105189764A (zh) | 2012-12-31 | 2015-12-23 | 英威达技术有限责任公司 | 通过与辅酶b合成相关的c1碳链延伸生产7-碳化学物的方法 |
| WO2014105796A2 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via aromatic compounds |
| WO2014105793A1 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals from long chain fatty acids via oxidative cleavage |
| US9580733B2 (en) | 2012-12-31 | 2017-02-28 | Invista North America S.A.R.L. | Methods of producing 6-carbon chemicals via methyl-ester shielded carbon chain elongation |
| US10196657B2 (en) | 2012-12-31 | 2019-02-05 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via methyl-ester shielded carbon chain elongation |
| BR112016026461A2 (pt) | 2014-05-15 | 2017-12-12 | Invista Tech Sarl | métodos de produção de produtos químicos com 6 carbonos com uso de 2,6-diaminopimelato como precursor para 2-aminopimelato |
| EP3155106A2 (en) | 2014-06-16 | 2017-04-19 | Invista Technologies S.à.r.l. | Methods, reagents and cells for biosynthesizing compound |
| WO2015195682A1 (en) | 2014-06-16 | 2015-12-23 | Invista Technologies S.À.R.L. | Methods, reagents and cells for biosynthesizing compounds |
| US9920339B2 (en) | 2014-06-16 | 2018-03-20 | Invista North America S.A.R.L. | Methods, reagents and cells for biosynthesizing compounds |
| EP3155107A1 (en) | 2014-06-16 | 2017-04-19 | Invista Technologies S.à.r.l. | Methods, reagents and cells for biosynthesizing compounds |
| WO2022029583A1 (en) | 2020-08-07 | 2022-02-10 | Inv Nylon Chemicals Americas, Llc | Production of dinitriles |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE705578C (de) * | 1936-05-12 | 1941-05-03 | Holzhydrolyse Akt Ges | Verfahren zur Herstellung von Laevulinsaeure oder ihren Estern |
| US2824122A (en) * | 1955-05-24 | 1958-02-18 | Cp Hall Co | Purification of alpha, omega alkanedioic acids by partial esterification |
| US2968674A (en) * | 1957-09-25 | 1961-01-17 | Gulf Research Development Co | Process for hydrolyzing dibasic acid esters while inhibiting the formation of color materials |
| NL243096A (Direct) | 1958-09-09 | 1900-01-01 | ||
| US3329712A (en) * | 1962-11-07 | 1967-07-04 | Monsanto Co | Separation of dibasic acids |
| US3365490A (en) * | 1966-08-05 | 1968-01-23 | Du Pont | Process for the production of dicarboxylic acids |
-
1969
- 1969-07-18 US US05/843,028 patent/US4058555A/en not_active Expired - Lifetime
- 1969-10-07 IE IE1387/69A patent/IE33335B1/xx unknown
- 1969-10-10 GB GB49898/69A patent/GB1282927A/en not_active Expired
- 1969-10-22 NO NO4193/69A patent/NO135467C/no unknown
- 1969-10-24 NL NL6916083A patent/NL6916083A/xx unknown
- 1969-11-13 JP JP44090506A patent/JPS4914204B1/ja active Pending
- 1969-11-17 LU LU59826D patent/LU59826A1/xx unknown
- 1969-11-17 BE BE741803D patent/BE741803A/xx not_active IP Right Cessation
- 1969-11-18 FR FR696939679A patent/FR2051826B1/fr not_active Expired
- 1969-11-19 CH CH1721469A patent/CH526504A/fr not_active IP Right Cessation
- 1969-11-25 ES ES373890A patent/ES373890A1/es not_active Expired
-
1970
- 1970-01-12 DE DE2001100A patent/DE2001100C2/de not_active Expired
- 1970-01-13 AT AT29170A patent/AT301578B/de active
- 1970-02-24 BR BR216945/70A patent/BR7016945D0/pt unknown
- 1970-07-17 SE SE09937/70A patent/SE368390B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH526504A (fr) | 1972-08-15 |
| GB1282927A (en) | 1972-07-26 |
| SE368390B (Direct) | 1974-07-01 |
| BE741803A (Direct) | 1970-05-04 |
| ES373890A1 (es) | 1972-02-16 |
| NO135467C (Direct) | 1977-04-13 |
| BR7016945D0 (pt) | 1973-05-03 |
| FR2051826B1 (Direct) | 1973-03-16 |
| DE2001100C2 (de) | 1983-02-10 |
| DE2001100A1 (de) | 1971-01-28 |
| FR2051826A1 (Direct) | 1971-04-09 |
| LU59826A1 (Direct) | 1970-01-19 |
| JPS4914204B1 (Direct) | 1974-04-05 |
| IE33335L (en) | 1971-01-18 |
| US4058555A (en) | 1977-11-15 |
| IE33335B1 (en) | 1974-05-29 |
| AT301578B (de) | 1972-09-11 |
| NL6916083A (Direct) | 1971-01-20 |
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