CA2629557C - An alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals and method of making the same - Google Patents
An alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals and method of making the same Download PDFInfo
- Publication number
- CA2629557C CA2629557C CA2629557A CA2629557A CA2629557C CA 2629557 C CA2629557 C CA 2629557C CA 2629557 A CA2629557 A CA 2629557A CA 2629557 A CA2629557 A CA 2629557A CA 2629557 C CA2629557 C CA 2629557C
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- mixture
- hydroxyaromatic
- hydroxyaromatic compound
- alkylated
- 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 - Fee Related
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- 238000006317 isomerization reaction Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000027758 ovulation cycle Effects 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- RQFVHGAXCJVPBZ-UHFFFAOYSA-N propylene pentamer Chemical compound CC=C.CC=C.CC=C.CC=C.CC=C RQFVHGAXCJVPBZ-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000011121 vaginal smear Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/10—Polyhydroxy benzenes; Alkylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/64—Environmental friendly compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/741,687 | 2007-04-27 | ||
| US11/741,687 US8207380B2 (en) | 2007-04-27 | 2007-04-27 | Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals and method of making the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2629557A1 CA2629557A1 (en) | 2008-10-27 |
| CA2629557C true CA2629557C (en) | 2016-06-21 |
Family
ID=39816934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2629557A Expired - Fee Related CA2629557C (en) | 2007-04-27 | 2008-04-21 | An alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals and method of making the same |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8207380B2 (enExample) |
| EP (1) | EP1995229B1 (enExample) |
| JP (2) | JP5710857B2 (enExample) |
| CN (1) | CN101306985B (enExample) |
| CA (1) | CA2629557C (enExample) |
| SG (1) | SG147396A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7943796B2 (en) * | 2008-07-31 | 2011-05-17 | Chevron Oronise Company LLC | Lubricating oil additive and lubricating oil composition containing same |
| US8486877B2 (en) * | 2009-11-18 | 2013-07-16 | Chevron Oronite Company Llc | Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals |
| US8580717B2 (en) * | 2009-11-24 | 2013-11-12 | Chevron Oronite Company Llc | Process for making an overbased, sulfurized salt of an alkylated hydroxyaromatic compound |
| JP2013518970A (ja) * | 2010-02-03 | 2013-05-23 | シェブロン・オロナイト・カンパニー・エルエルシー | 潤滑油添加剤およびそれを含む潤滑油組成物 |
| US8704006B2 (en) * | 2010-12-10 | 2014-04-22 | Chevron Oronite Company Llc | Skewed and middle attached linear chain alkylphenol and method of making the same |
| US20140228265A1 (en) | 2011-10-20 | 2014-08-14 | The Lubrizol Corporation | Bridged Alkylphenol Compounds |
| SG11201404656RA (en) | 2012-02-08 | 2014-09-26 | Lubrizol Corp | Method of preparing a sulfurized alkaline earth metal dodecylphenate |
| EP2682451B1 (en) | 2012-07-06 | 2015-11-18 | Infineum International Limited | Detergent modification |
| CN111825818B (zh) | 2013-10-17 | 2023-11-21 | Si集团有限公司 | 原位烷基苯酚-醛树脂 |
| HK1222190A1 (zh) | 2013-10-17 | 2017-06-23 | Si Group, Inc. | 通過水楊酸穩定的改性烷基苯酚-醛樹脂 |
| CN106103673A (zh) | 2014-01-10 | 2016-11-09 | 路博润公司 | 润滑内燃机的方法 |
| US20160326452A1 (en) | 2014-01-10 | 2016-11-10 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
| WO2015183685A1 (en) | 2014-05-28 | 2015-12-03 | The Lubrizol Corporation | Alkylphenol detergents |
| KR102608828B1 (ko) | 2015-02-26 | 2023-11-30 | 더루브리졸코오퍼레이션 | 방향족 세제 및 이의 윤활 조성물 |
| JP5960311B2 (ja) * | 2015-03-06 | 2016-08-02 | シェブロン・オロナイト・カンパニー・エルエルシー | 潤滑油添加剤およびそれを含む潤滑油組成物 |
| BR112017019385A2 (pt) | 2015-03-09 | 2018-04-24 | Lubrizol Corp | método de lubrificação de um motor de combustão interna |
| WO2017087384A1 (en) | 2015-11-17 | 2017-05-26 | The Lubrizol Corporation | Toxicologically acceptable alkylphenol detergents as friction modifiers in automotive lubricating oils |
| CA3007127A1 (en) | 2015-12-15 | 2017-06-22 | The Lubrizol Corporation | Sulfurized catecholate detergents for lubricating compositions |
| EP3472278A1 (en) | 2016-06-17 | 2019-04-24 | The Lubrizol Corporation | Lubricating compositions |
| SG11201810337PA (en) | 2016-06-17 | 2018-12-28 | Lubrizol Corp | Lubricating compositions |
| SG11201810335VA (en) | 2016-06-17 | 2018-12-28 | Lubrizol Corp | Polyisobutylene-substituted phenol, derivatives thereof, and lubricating compositions containing the polyisobutylene-substituted phenol and its derivatives |
| EP3472277A1 (en) | 2016-06-17 | 2019-04-24 | The Lubrizol Corporation | Lubricating compositions |
| US10260019B2 (en) | 2016-06-30 | 2019-04-16 | The Lubrizol Corporation | Hydroxyaromatic succinimide detergents for lubricating compositions |
| CN111433331A (zh) * | 2017-12-04 | 2020-07-17 | 路博润公司 | 烷基酚清洁剂 |
| CN111479908A (zh) | 2017-12-15 | 2020-07-31 | 路博润公司 | 烷基酚清洁剂 |
| WO2021161199A1 (en) * | 2020-02-14 | 2021-08-19 | Chevron Oronite Company Llc | Alkyl-substituted hydroxyaromatic compounds with highly- structured alkyl branches |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS509779B1 (enExample) * | 1966-08-25 | 1975-04-16 | ||
| CS226912B1 (cs) | 1981-11-02 | 1984-04-16 | Pac Jiri | Substituované fenoly |
| US4708809A (en) * | 1982-06-07 | 1987-11-24 | The Lubrizol Corporation | Two-cycle engine oils containing alkyl phenols |
| DE3368606D1 (en) * | 1982-12-13 | 1987-02-05 | Shell Int Research | Alkylxylene sulphonate compounds, their preparation and use |
| US4475001A (en) * | 1983-03-17 | 1984-10-02 | Koppers Company, Inc. | Process for alkylating phenolic compounds to produce ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylated phenols |
| JPS60228438A (ja) * | 1984-04-27 | 1985-11-13 | Osuka Kagaku Kk | モノアルキルフェノールの製造方法 |
| US4643838A (en) * | 1985-09-18 | 1987-02-17 | Chevron Research Company | Normally liquid C18 to C24 monoalkyl catechols |
| JP2548934B2 (ja) * | 1986-06-10 | 1996-10-30 | 住友化学工業株式会社 | ヒドロキシ含有アルキル芳香族化合物の製造法 |
| JPH02500978A (ja) * | 1986-10-24 | 1990-04-05 | エクソン リサーチ アンド エンヂニアリング コムパニー | 分解石油留出物によるフェノールアルキル化経由アルキルフェノールおよびそれらの誘導体 |
| US4973764A (en) * | 1986-10-24 | 1990-11-27 | Exxon Research And Engineering Company | Alkylphenols and derivatives thereof via phenol alkylation by cracked petroleum distillates |
| US5663457A (en) * | 1996-02-16 | 1997-09-02 | The Lubrizol Corporation | Methods for preparing alkylated hydroxyaromatics |
| CA2204461C (en) * | 1996-05-14 | 2006-07-04 | Thomas V. Harris | Process for producing an alkylated, non-oxygen-containing aromatic hydrocarbon |
| US6191317B1 (en) * | 1999-08-31 | 2001-02-20 | Huntsman Petrochemical Corporation | Process for preparation of polyalkyl hydroxyaromatics |
| US6670513B1 (en) * | 1999-12-03 | 2003-12-30 | Chevron Oronite Company, Llc | Process for producing alkylated hydroxyl-containing aromatic compounds |
| US6765106B2 (en) * | 2001-02-15 | 2004-07-20 | Shell Oil Company | Process for preparing a branched olefin, a method of using the branched olefin for making a surfactant, and a surfactant |
| MXPA04001319A (es) * | 2001-08-17 | 2004-05-20 | Shell Int Research | Proceso de produccion de olefinas ramificadas a partir de una fuente de olefinas/parafinas lineales. |
| JP4208543B2 (ja) * | 2002-10-11 | 2009-01-14 | 三井化学株式会社 | 分岐型極性基含有オレフィン共重合体 |
| US7041864B2 (en) | 2002-12-11 | 2006-05-09 | Shell Oil Company | Linear and branched olefin production from cyclic olefin feedstocks |
| US7041884B2 (en) * | 2003-01-09 | 2006-05-09 | Syngenta Participations Ag | Inbred maize line 291B |
| US8188020B2 (en) | 2003-12-22 | 2012-05-29 | Chevron Oronite S.A. | Lubricating oil composition containing an alkali metal detergent |
| US7435709B2 (en) | 2005-09-01 | 2008-10-14 | Chevron Oronite Company Llc | Linear alkylphenol derived detergent substantially free of endocrine disruptive chemicals |
-
2007
- 2007-04-27 US US11/741,687 patent/US8207380B2/en active Active
-
2008
- 2008-03-26 EP EP08251077A patent/EP1995229B1/en active Active
- 2008-04-21 CA CA2629557A patent/CA2629557C/en not_active Expired - Fee Related
- 2008-04-22 SG SG200803075-1A patent/SG147396A1/en unknown
- 2008-04-24 JP JP2008114308A patent/JP5710857B2/ja active Active
- 2008-04-25 CN CN200810142815.8A patent/CN101306985B/zh active Active
-
2014
- 2014-11-14 JP JP2014231949A patent/JP2015052008A/ja not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015052008A (ja) | 2015-03-19 |
| EP1995229B1 (en) | 2012-08-29 |
| US8207380B2 (en) | 2012-06-26 |
| JP2008273967A (ja) | 2008-11-13 |
| JP5710857B2 (ja) | 2015-04-30 |
| SG147396A1 (en) | 2008-11-28 |
| CN101306985A (zh) | 2008-11-19 |
| EP1995229A2 (en) | 2008-11-26 |
| CA2629557A1 (en) | 2008-10-27 |
| EP1995229A3 (en) | 2009-04-22 |
| CN101306985B (zh) | 2014-06-25 |
| US20080269351A1 (en) | 2008-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130422 |
|
| MKLA | Lapsed |
Effective date: 20210421 |