RU2005116313A - Способ алкилирования салициловой кислоты - Google Patents
Способ алкилирования салициловой кислоты Download PDFInfo
- Publication number
- RU2005116313A RU2005116313A RU2005116313/04A RU2005116313A RU2005116313A RU 2005116313 A RU2005116313 A RU 2005116313A RU 2005116313/04 A RU2005116313/04 A RU 2005116313/04A RU 2005116313 A RU2005116313 A RU 2005116313A RU 2005116313 A RU2005116313 A RU 2005116313A
- Authority
- RU
- Russia
- Prior art keywords
- elevated temperature
- acid
- olefin
- propylene
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 title claims abstract 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 title claims abstract 5
- 229960004889 salicylic acid Drugs 0.000 title claims abstract 5
- 230000029936 alkylation Effects 0.000 title 1
- 238000005804 alkylation reaction Methods 0.000 title 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract 11
- 150000001336 alkenes Chemical class 0.000 claims abstract 7
- 239000002253 acid Substances 0.000 claims abstract 5
- 239000003054 catalyst Substances 0.000 claims abstract 5
- -1 alkyl salicylic acids Chemical class 0.000 claims abstract 4
- 230000002378 acidificating effect Effects 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 239000004927 clay Substances 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims 10
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims 8
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims 8
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 8
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims 8
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims 8
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 claims 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 4
- 229940069096 dodecene Drugs 0.000 claims 4
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 claims 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 4
- ZDLBWMYNYNATIW-UHFFFAOYSA-N tetracos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCC=C ZDLBWMYNYNATIW-UHFFFAOYSA-N 0.000 claims 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (12)
1. Способ производства алкилсалициловых кислот, включающий взаимодействие салициловой кислоты с олефином, содержащим, по меньшей мере, четыре атома углерода, при повышенной температуре в присутствии перфторалкилсульфоновой кислоты, алкилсульфоновой кислоты или кислой глины в качестве катализатора.
2. Способ по п.1, в котором катализатором является безводная метансульфоновая кислота.
3. Способ по п.1, в котором олефин выбирают из группы, состоящей из изобутилена, тримера пропилена, тетрамера пропилена, 1-гексена, 1-октена, 1-децена, 1-додецена, 1-тетрадецена, 1-гексадецена, 1-октадецена, 1-эйкозена, 1-докозена, 1-тетракозена и их смесей.
4. Способ по п.2, в котором олефин выбирают из группы, состоящей из изобутилена, тримера пропилена, тетрамера пропилена, 1-гексена, 1-октена, 1-децена, 1-додецена, 1-тетрадецена, 1-гексадецена, 1-октадецена, 1-эйкозена, 1-докозена, 1-тетракозена и их смесей.
5. Способ по п.1, в котором указанная повышенная температура составляет, по меньшей мере, около 50°С.
6. Способ по п.1, в котором указанная повышенная температура составляет от около 120 до около 160°С.
7. Композиция, содержащая алкилсалициловую кислоту, полученную способом, включающим взаимодействие салициловой кислоты с олефином, содержащим, по меньшей мере, четыре атома углерода, при повышенной температуре в присутствии перфторалкилсульфоновой кислоты, алкилсульфоновой кислоты или кислой глины в качестве катализатора.
8. Композиция по п.7, где катализатором является безводная метансульфоновая кислота.
9. Композиция по п.7, где олефин выбран из группы, состоящей из изобутилена, тримера пропилена, тетрамера пропилена, 1-гексена, 1-октена, 1-децена, 1-додецена, 1-тетрадецена, 1-гексадецена, 1-октадецена, 1-эйкозена, 1-докозена, 1-тетракозена и их смесей.
10. Композиция по п.8, где олефин выбран из группы, состоящей из изобутилена, тримера пропилена, тетрамера пропилена, 1-гексена, 1-октена, 1-децена, 1-додецена, 1-тетрадецена, 1-гексадецена, 1-октадецена, 1-эйкозена, 1-докозена, 1-тетракозена и их смесей.
11. Композиция по п.7, где указанная повышенная температура составляет, по меньшей мере, около 50°С.
12. Композиция по п.11, где указанная повышенная температура составляет от около 120 до около 160°С.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42249202P | 2002-10-31 | 2002-10-31 | |
| US60/422,492 | 2002-10-31 | ||
| US10/691,390 US7045654B2 (en) | 2002-10-31 | 2003-10-21 | Method for the alkylation of salicylic acid |
| US10/691,390 | 2003-10-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005116313A true RU2005116313A (ru) | 2006-01-20 |
| RU2331631C2 RU2331631C2 (ru) | 2008-08-20 |
Family
ID=32314455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005116313/04A RU2331631C2 (ru) | 2002-10-31 | 2003-10-22 | Способ алкилирования салициловой кислоты |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7045654B2 (ru) |
| EP (1) | EP1556326B1 (ru) |
| JP (1) | JP4205671B2 (ru) |
| AT (1) | ATE342247T1 (ru) |
| AU (1) | AU2003284326A1 (ru) |
| DE (1) | DE60309060T2 (ru) |
| RU (1) | RU2331631C2 (ru) |
| WO (1) | WO2004041766A1 (ru) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008013752A2 (en) * | 2006-07-28 | 2008-01-31 | Exxonmobil Research And Engineering Company | Improving lubricant air release rates |
| WO2008013754A2 (en) * | 2006-07-28 | 2008-01-31 | Exxonmobil Research And Engineering Company | Lubricant compositions, their preparation and use |
| EP2049634B1 (en) * | 2006-07-28 | 2018-09-19 | ExxonMobil Research and Engineering Company | Improvment of rates of air release of lubricant compositions |
| WO2008013753A2 (en) * | 2006-07-28 | 2008-01-31 | Exxonmobil Research And Engineering Company | Novel application of thickeners to achieve favorable air release in lubricants |
| US7770914B2 (en) * | 2007-07-31 | 2010-08-10 | Autoliv Asp, Inc. | Passenger airbag mounting apparatus |
| DE102009034984A1 (de) * | 2008-09-11 | 2010-07-01 | Infineum International Ltd., Abingdon | Detergens |
| CN102260169B (zh) | 2011-06-09 | 2016-04-13 | 无锡南方石油添加剂有限公司 | 一种润滑油清净剂及其生产工艺 |
| RU2477784C1 (ru) * | 2011-10-25 | 2013-03-20 | Открытое акционерное общество "Всероссийский нефтегазовый научно-исследовательский институт имени академика А.П. Крылова" (ОАО "ВНИИнефть") | Способ разработки нефтегазового месторождения с применением водогазового воздействия |
| CN104098466B (zh) * | 2013-04-03 | 2016-01-20 | 中国石油天然气股份有限公司 | 一种烷基水杨酸盐的制备方法 |
| CN108463455B (zh) | 2015-11-10 | 2021-06-15 | 巴斯夫欧洲公司 | 再加工链烷磺酸的方法 |
| RU2627768C1 (ru) * | 2016-10-14 | 2017-08-11 | Публичное акционерное общество "Нефтяная компания "Роснефть" | Способ получения алкилсалициловой кислоты |
| WO2019014255A1 (en) | 2017-07-11 | 2019-01-17 | Si Group, Inc. | PROCESS FOR THE PREPARATION OF ALKYLSALICYLIC ACID AND PRODUCTS THEREOF |
| RU2697198C1 (ru) * | 2018-05-30 | 2019-08-13 | Публичное акционерное общество "Средневолжский научно-исследовательский институт по нефтепереработке" (ПАО "СвНИИНП") | Способ очистки алкилсалициловых кислот |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE293108C (ru) | ||||
| DE269619C (ru) | ||||
| US1998750A (en) * | 1931-12-30 | 1935-04-23 | Resinous Prod & Chemical Co | Salicylic acid derivative |
| DE689600C (de) | 1934-12-23 | 1940-04-12 | Hydrierwerke Akt Ges Deutsche | , die eine olefinische Doppelbindung im Molekuel enthalten, mit aromatischen oder gemischt aromatisch-alicyclischen Kohlenwasserstoffen |
| US2490444A (en) * | 1946-09-13 | 1949-12-06 | Shell Dev | Alkylated aromatic compounds of improved color from impure starting materials |
| GB786167A (en) * | 1954-09-27 | 1957-11-13 | Shell Res Ltd | Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts |
| US3337616A (en) * | 1964-12-18 | 1967-08-22 | Dow Chemical Co | Preparation of salicylic acids |
| GB1094609A (en) * | 1965-08-23 | 1967-12-13 | Lubrizol Corp | Oil soluble basic alkaline earth metal salts of phenol sulfides |
| US3557198A (en) * | 1967-04-12 | 1971-01-19 | Tenneco Chem | Process for the production of alkali metal salicylates |
| US3438899A (en) * | 1968-02-23 | 1969-04-15 | Chevron Res | Alkenyl succinimide of tris (aminoalkyl) amine |
| GB1184020A (en) * | 1968-12-19 | 1970-03-11 | Shell Int Research | Salts of Polyvalent Metals and Alkylsalicylic Acids |
| US3853956A (en) * | 1969-03-20 | 1974-12-10 | Universal Oil Prod Co | Reaction of phenols with olefins and cupric halide |
| CH579579A5 (ru) * | 1972-11-22 | 1976-09-15 | Ciba Geigy Ag | |
| US4060535A (en) * | 1976-08-31 | 1977-11-29 | Tenneco Chemicals, Inc. | Process for the production of metal salts of organic acids |
| US4544491A (en) * | 1983-08-24 | 1985-10-01 | Claypro Associates | Recovery of hydrocarbon oil from filter cakes |
| US4910334A (en) * | 1983-08-24 | 1990-03-20 | Claypro Corporation | Recovery of overbased alkaline earth metal additives from centrifugates |
| GB8703549D0 (en) * | 1987-02-16 | 1987-03-25 | Shell Int Research | Preparation of basic salt |
| GB8714922D0 (en) * | 1987-06-25 | 1987-07-29 | Shell Int Research | Lubricating oil composition |
| GB8716159D0 (en) * | 1987-07-09 | 1987-08-12 | Shell Int Research | Basic salt |
| GB8814008D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Lubricating oil additives |
| JPH0291043A (ja) | 1988-09-29 | 1990-03-30 | Yoshitomi Pharmaceut Ind Ltd | サリチル酸誘導体の製造方法 |
| US5049685A (en) * | 1988-11-22 | 1991-09-17 | Sanko Kaihatsu Kagaku Kenkyusho | Nuclear substituted salicylic acids and their salts |
| US5225588A (en) * | 1992-02-03 | 1993-07-06 | Ethyl Corporation | Process for alkylating salicylates with polyalphaolefin |
| US5652203A (en) * | 1992-09-10 | 1997-07-29 | Kao Corporation | Process of overbasing a salicylic ester and product thereof |
| TW278098B (ru) * | 1992-09-18 | 1996-06-11 | Cosmo Sogo Kenkyusho Kk | |
| US5259966A (en) * | 1992-11-10 | 1993-11-09 | The Lubrizol Corporation | Low chlorine overbased calcium salts |
| US5434293A (en) * | 1993-12-23 | 1995-07-18 | Chevron Chemical Company | Alkylation of alkyl salicylate using a long chain carbon feed |
| US5415792A (en) * | 1993-12-23 | 1995-05-16 | Chevron Chemical Company | Overbased alkylated alkyl salicylates |
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| GB9522359D0 (en) * | 1995-11-01 | 1996-01-03 | Bp Chemicals Additives | Alkylation process |
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-
2003
- 2003-10-21 US US10/691,390 patent/US7045654B2/en not_active Expired - Lifetime
- 2003-10-22 EP EP03776507A patent/EP1556326B1/en not_active Expired - Lifetime
- 2003-10-22 WO PCT/US2003/033498 patent/WO2004041766A1/en active IP Right Grant
- 2003-10-22 AU AU2003284326A patent/AU2003284326A1/en not_active Abandoned
- 2003-10-22 JP JP2004550076A patent/JP4205671B2/ja not_active Expired - Fee Related
- 2003-10-22 RU RU2005116313/04A patent/RU2331631C2/ru not_active IP Right Cessation
- 2003-10-22 AT AT03776507T patent/ATE342247T1/de not_active IP Right Cessation
- 2003-10-22 DE DE60309060T patent/DE60309060T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU2331631C2 (ru) | 2008-08-20 |
| US7045654B2 (en) | 2006-05-16 |
| DE60309060T2 (de) | 2007-02-22 |
| ATE342247T1 (de) | 2006-11-15 |
| EP1556326A1 (en) | 2005-07-27 |
| DE60309060D1 (de) | 2006-11-23 |
| JP2006518329A (ja) | 2006-08-10 |
| US20040127743A1 (en) | 2004-07-01 |
| WO2004041766A1 (en) | 2004-05-21 |
| EP1556326B1 (en) | 2006-10-11 |
| AU2003284326A1 (en) | 2004-06-07 |
| JP4205671B2 (ja) | 2009-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20131023 |