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
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 (xx) | 1977-01-03 |
| NO135467C NO135467C (xx) | 1977-04-13 |
Family
ID=25288880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4193/69A NO135467C (xx) | 1969-07-18 | 1969-10-22 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4058555A (xx) |
| JP (1) | JPS4914204B1 (xx) |
| AT (1) | AT301578B (xx) |
| BE (1) | BE741803A (xx) |
| BR (1) | BR7016945D0 (xx) |
| CH (1) | CH526504A (xx) |
| DE (1) | DE2001100C2 (xx) |
| ES (1) | ES373890A1 (xx) |
| FR (1) | FR2051826B1 (xx) |
| GB (1) | GB1282927A (xx) |
| IE (1) | IE33335B1 (xx) |
| LU (1) | LU59826A1 (xx) |
| NL (1) | NL6916083A (xx) |
| NO (1) | NO135467C (xx) |
| SE (1) | SE368390B (xx) |
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 |
| JP6058650B2 (ja) | 2011-06-17 | 2017-01-11 | インビスタ テクノロジーズ エス．アー．エール．エル． | 廃棄流中のモノマー含有量を増大させるためのヒドロラーゼの使用 |
| US9650653B2 (en) | 2011-06-30 | 2017-05-16 | Invista North America S.A.R.L. | Bioconversion process for producing nylon-7, nylon-7,7 and polyesters |
| 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 |
| 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 |
| 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 |
| US9637764B2 (en) | 2012-12-31 | 2017-05-02 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via carbon chain elongation associated with cyclohexane carboxylate synthesis |
| 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 |
| EP2938736A2 (en) | 2012-12-31 | 2015-11-04 | Invista Technologies S.A R.L. | Methods of producing 7-carbon chemicals via c1 carbon chain elongation associated with coenzyme b synthesis |
| EP2938734A2 (en) | 2012-12-31 | 2015-11-04 | Invista Technologies S.A R.L. | Methods of producing 7-carbon chemicals via aromatic compounds |
| 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 |
| US9738911B2 (en) | 2012-12-31 | 2017-08-22 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via pyruvate and succinate semialdehyde aldol condensation |
| EP2938732A1 (en) | 2012-12-31 | 2015-11-04 | Invista Technologies S.à.r.l. | Methods of producing 7-carbon chemicals from long chain fatty acids via oxidative cleavage |
| CN106574283A (zh) | 2014-05-15 | 2017-04-19 | 英威达技术有限责任公司 | 使用2,6‑二氨基庚二酸作为2‑氨基庚二酸的前体生产6‑碳化学品的方法 |
| WO2015195707A1 (en) | 2014-06-16 | 2015-12-23 | Invista Technologies S.A.R.L. | Methods, reagents and cells for biosynthesizing compounds |
| WO2015195611A2 (en) | 2014-06-16 | 2015-12-23 | Invista Technologies S.À.R.L. | Methods, reagents and cells for biosynthesizing compound |
| CN106795536A (zh) | 2014-06-16 | 2017-05-31 | 英威达技术有限责任公司 | 用于生物合成化合物的方法、试剂和细胞 |
| BR112016029471A2 (pt) | 2014-06-16 | 2017-10-24 | Invista Tech Sarl | método para biosintetizar éster de metil glutarato em um hospedeiro recombinante, método para preparar glutarato, célula hospedeira recombinante, hospedeiro recombinante, produto bioderivado, produto de base biológica ou produto derivado de fermentação e método para aumentar a atividade de um polipeptídeo tendo atividade carboxilato reductase sobre um ácido dicarboxílico c4-c8 substituído ou não-substituído |
| CN115734963A (zh) | 2020-08-07 | 2023-03-03 | 英威达纺织（英国）有限公司 | 二腈的生产 |
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 (xx) | 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 |
|---|---|
| IE33335L (en) | 1971-01-18 |
| AT301578B (de) | 1972-09-11 |
| FR2051826A1 (xx) | 1971-04-09 |
| IE33335B1 (en) | 1974-05-29 |
| NO135467C (xx) | 1977-04-13 |
| DE2001100C2 (de) | 1983-02-10 |
| BE741803A (xx) | 1970-05-04 |
| SE368390B (xx) | 1974-07-01 |
| CH526504A (fr) | 1972-08-15 |
| DE2001100A1 (de) | 1971-01-28 |
| NL6916083A (xx) | 1971-01-20 |
| FR2051826B1 (xx) | 1973-03-16 |
| BR7016945D0 (pt) | 1973-05-03 |
| JPS4914204B1 (xx) | 1974-04-05 |
| ES373890A1 (es) | 1972-02-16 |
| GB1282927A (en) | 1972-07-26 |
| LU59826A1 (xx) | 1970-01-19 |
| US4058555A (en) | 1977-11-15 |
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