WO2007022718A1 - Alcools alkylaryle, leurs derives et leur procede de preparation - Google Patents

Alcools alkylaryle, leurs derives et leur procede de preparation Download PDF

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Publication number
WO2007022718A1
WO2007022718A1 PCT/CN2006/002151 CN2006002151W WO2007022718A1 WO 2007022718 A1 WO2007022718 A1 WO 2007022718A1 CN 2006002151 W CN2006002151 W CN 2006002151W WO 2007022718 A1 WO2007022718 A1 WO 2007022718A1
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group
compound
alkyl
formula
integer
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PCT/CN2006/002151
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English (en)
Chinese (zh)
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WO2007022718A8 (fr
WO2007022718B1 (fr
Inventor
Chunde Liu
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Chunde Liu
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Priority claimed from CN200510092891.9A external-priority patent/CN1919438A/zh
Priority claimed from CN200510092889.1A external-priority patent/CN1919830A/zh
Priority claimed from CN200510092890.4A external-priority patent/CN1919831A/zh
Priority claimed from CN 200510093709 external-priority patent/CN1923873A/zh
Priority claimed from CN 200510104852 external-priority patent/CN1935760A/zh
Priority claimed from CN 200510104851 external-priority patent/CN1935759A/zh
Application filed by Chunde Liu filed Critical Chunde Liu
Priority to CNA2006800298476A priority Critical patent/CN101243029A/zh
Publication of WO2007022718A1 publication Critical patent/WO2007022718A1/fr
Publication of WO2007022718B1 publication Critical patent/WO2007022718B1/fr
Publication of WO2007022718A8 publication Critical patent/WO2007022718A8/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/38—Alcohols, e.g. oxidation products of paraffins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
    • C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/14—Derivatives of phosphoric acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines

Definitions

  • This invention relates to a novel alkylaryl mercapto alcohol and related products. Background technique
  • High-grade fatty alcohols are very important raw materials in organic chemicals, and their application fields are very wide.
  • Higher fatty alcohols are classified into plasticizer alcohols and detergent alcohols according to commercial use.
  • Higher fatty alcohols for plasticizers is c 8 ⁇ c 1Q alcohols and monocarboxylic acids, dicarboxylic acids and polycarboxylic acids obtained by reacting ester; and higher fatty alcohols for detergents are c 12 ⁇ c 18 Alcohol, its derivative c 12 ⁇ c 18 alcohol polyoxyethylene ether, is an important nonionic surfactant, mainly used in liquid detergents, cleaning agents and textile auxiliaries.
  • Alcohol ether sulfates are important fatty alcohol derivatives, mainly used in shampoos, dishwashing detergents, liquid detergents, foaming agents, and the like.
  • the hydroxyl structure in the chemical structure of the terpene fatty alcohol is very high, and it can react with many substances to further become higher fatty amines and higher fatty acids, thereby deriving an anionic surfactant, a betaine surfactant, and an amino acid surface.
  • Active agent, cationic surfactant and the like since the higher aliphatic alcohol has a large carbon number, the melting point is ⁇ , and it does not flow under normal temperature conditions, and the application is very inconvenient, and its application in some aspects is limited.
  • An object of the present invention is to provide a mercaptoarylalkyl alcohol and related products which are excellent in fluidity at normal temperature.
  • Another object of the present invention is to provide the above novel alkylarylalkyl alcohols, related products thereof and their use in various fields.
  • the inventors of the present invention found that by using mercaptobenzene, alkylnaphthalene, alkylbiphenyl, decyl diphenyl ether as raw materials, it is possible to synthesize a sulfhydryl group which has good fluidity at normal temperature.
  • the decyl alcohol and its related products lead to the completion of the present invention.
  • the present invention provides the following aspects:
  • n is any integer from 2 to 30;
  • n is any one of 1 to 12;
  • Ar is any of phenyl, nonylphenyl, naphthyl, nonylnaphthyl, biphenyl, nonylbiphenyl, diphenyl ether, diphenylmethylalkyl and 1,2-diphenylethenyl one kind; wherein the alkyl group is alkyl with 12 ⁇ C any one of an alkyl naphthyl group alkyl with arbitrary d ⁇ C 16 of one, and the biphenyl group embankment The alkyl group is d ⁇ . Any of 16 ; and
  • Q is any one of -OH, -(NR!Ra), and 3 ⁇ 4, where
  • any of R , -c3 ⁇ 4, ee QH , ⁇ is any integer
  • R is any one of -H, -CH 2 C00M, -S0 3 M, -R'-S0 3 M and - P0 3 M 2 ;
  • R' is any one of sulfhydryl groups;
  • M is any one of sodium, potassium, amine, lithium, monoethanolamine, diethanolamine, and triethanolamine.
  • n is any one of 8 to 12;
  • n is any one of 1 to 6;
  • Ar is any one of a phenyl group, an alkylphenyl group, a naphthyl group, a decylnaphthyl group, a biphenyl group, a fluorenylbiphenyl group, and a diphenyl ether; wherein the alkyl group in the alkylphenyl group is ⁇ C Any one of 6 wherein the alkyl group in the alkylnaphthyl group is
  • Ci to C 6 and the alkyl group in the indenylbiphenyl group is any one of C, ⁇ C 6 ;
  • Q is any one of -OH, -(NRiR 2 ), and a, where
  • any of H, -0H S and + C C 0 H , ⁇ is 1; is any of - H , — c ⁇ CM ⁇ O - ⁇ B, y is 1; q is 0 to 50 Any one of the integers; R is any one of -H, -CH 2 C00M, -S0 3 M, -R'-S0 3 M and -P0 3 M 2 ; R' is any alkyl group of ⁇ C 6 And M is any one of sodium, potassium, amine, lithium, monoethanolamine, diethanolamine, and triethanolamine.
  • n is any one of 8 to 12;
  • n is any one of 2 to 6;
  • Ar is any one of a phenyl group, a naphthyl group, a biphenyl group, and a diphenyl ether;
  • Q is any one of - ⁇ , - (NR!Rz) and 1, where any one of -H and -CH 3 is any one of -11 and -CH 3 ;
  • q is 0 to 25 Any one of the integers;
  • R is any one of -H, -C3 ⁇ 4C00M, -S0 3 M and -R'-S0 3 M;
  • R' is any one of ⁇ C 6 ;
  • M is sodium, potassium, amine Any one of monoethanolamine, diethanolamine and triethanolamine.
  • n is any one of 8 to 12;
  • n is any one of 2 to 6;
  • Ar is any one of a phenyl group and a naphthyl group
  • Q is -OH, Any one of them, where is -. 3 ⁇ 4 , R 2 is -CH 3 ; q is an integer of any one of 0 to 15; R is any one of -H, -C3 ⁇ 4C00M, -S0 3 M; and M is sodium, potassium, amine, monoethanolamine Any one of diethanolamine and triethanolamine.
  • m 12;
  • n 2;
  • Ar is a phenyl group
  • Q is any one of -OH and q;
  • R is -H.
  • m is any one of 2 to 30;
  • n is any one of 1 to 12
  • Ar is any of phenyl, nonylphenyl, naphthyl, nonylnaphthyl, biphenyl, nonylbiphenyl, diphenyl ether, diphenylmethylalkyl and 1,2-diphenylethenyl one kind; wherein the phenyl embankment embankment group is any one of 12 d ⁇ C one of an alkyl naphthyl group is ⁇ C 16 alkyl with any one of a, biphenyl group and the alkyl The alkyl group is any one of Ci to C 16 ;
  • the method includes: The compound of the following formula ( ⁇ ) is reacted with a dihalogenated anthracene of the following formula (III),
  • n is as defined above, and X represents a halogen atom
  • the compound of formula (IV) is hydrolyzed to provide a compound of formula (I).
  • Figure 1 is an infrared spectrum of the dodecyl phenylbutanol synthesized in Example 2. Detailed ways
  • n is any one of 1 to 12;
  • Ar is any one of a phenyl group, an alkylphenyl group, a naphthyl group, an alkylnaphthyl group, a biphenyl group, an alkylbiphenyl group, a diphenyl ether group, and a diphenylmethylalkyl group; wherein, in the nonylphenyl group, The alkyl group is any one of d to C 12 , the alkyl group in the mercapto naphthyl group is any one of ⁇ to C 16 , and the alkyl group in the alkyl biphenyl group is in d to c 16 Any one;
  • Q is -OH, -(NR!R and q, where 1 ⁇ is
  • ⁇ , X is any integer in the middle; - H, -C3 ⁇ 4 ⁇ CH JC H S 0 ⁇ - H in which arbitrary - a, y is any one of an integer l ⁇ 50; q 3 ⁇ 4 any one of an integer from 0 to 50; R & lt is -H, -CH 2 Any one of C00M, -S0 3 M, -R'-S0 3 M and - P0 3 M 2 ; R' is any alkyl group; and M is sodium, potassium, amine, lithium, monoethanolamine, two Any of ethanolamine and triethanolamine.
  • m is preferably any one of 8 to 12
  • n is an integer of 2 to 4
  • Ar is a phenyl group, a naphthyl group, a biphenyl group, a diphenyl ether. Any one of them;
  • Q is -0H, -(NR!R 2 ) - 0 -4- C3 ⁇ 4C3 ⁇ 40 - -R
  • R' is any alkyl group of ⁇ C 6 ; and M is any one of sodium, potassium, amine, lithium, monoethanolamine, diethanolamine, and triethanolamine.
  • n is 2 to 2.
  • Ar is a phenyl group, a naphthyl group;
  • Q is -0H, -( ⁇ 2) and
  • Ri -CH Ri -CH ; R 2 is -C3 ⁇ 4 ; q is any integer from 0 to 15; R is any one of -H, -CH 2 C00M and -S0 3 M; Any of sodium, potassium, amine, monoethanolamine, diethanolamine, and triethanolamine.
  • m is 12, n is 2, Ar is a phenyl group, and Q is -0H.
  • the compound of the present invention has a large carbon number, it contains an aryl group, and the melting point is greatly lowered, and the application is very convenient.
  • the raw material is derived from mercaptobenzene or alkylnaphthalene, and the cost is low, and it can replace the higher fatty alcohol.
  • novel mercaptoaryl alcohols can be used alone or in combination with other materials in various fields.
  • the alkylarylalkyl polyoxyethylene ether or the alkylarylalkyl polyoxypropylene ether can be obtained by reacting the mercaptoarylalkyl alcohol of the present invention with an ethylene oxide or a propylene oxide as an intermediate.
  • the alkylarylalkyl alcohol of the present invention is used as a raw material, and further oxidized to form an alkylarylalkyl acid, and the acid is neutralized to form a soap, which can be converted into an anionic surfactant.
  • the alkylarylalkyl alcohol of the present invention is used as a raw material, which is sulfonated and neutralized to form a mercaptoarylalkyl sulfonate.
  • Using the alkylarylalkyl alcohol of the present invention as a raw material further reacting into an alkylarylalkylamine, further with sodium chloroacetate, sodium hydroxyacetate, sodium hydroxypropionate, methyl acrylate, hydrogen peroxide, halogen
  • the reaction such as substitution or the like becomes a structure of a betaine type surfactant, an amino acid type surfactant, a cationic surfactant, and the like.
  • the application of the above structure is still within the scope of the invention.
  • Higher fatty alcohols are classified into plasticizer alcohols and detergent alcohols according to commercial use, and the mercaptoarylalkyl alcohols of the present invention have It has the properties of higher fatty alcohols and can be used in various fields instead of higher fatty alcohols.
  • the high-fat alcohol has a large carbon number, the melting point is high, and it does not flow under normal temperature conditions, and the application is very inconvenient, and is limited in some aspects, and the novel mercaptoarylalkyl alcohol of the present invention contains a large amount of carbon, but contains aromatic Ring, the point is not high, the fluidity is good under normal temperature conditions, the application is very convenient, and the raw material is derived from alkylbenzene, which is low in cost and can replace high-grade fatty alcohol.
  • the product was hydrolyzed at 150 ° C to obtain mercaptophenylethanol, and the obtained nonylphenylethanol was dehydrated under reduced pressure at 110 ° C.
  • the dehydrated sulfhydryl group was dehydrated under the condition of nitrogen gas protection in the reaction vessel.
  • the phenylethyl alcohol is mixed with a basic catalyst (NaOH) to a temperature of 160 ° C and then charged with liquid or gaseous epoxy acetam.
  • the partial pressure of the epoxy oxime was maintained at about 0.4 to 0.5 MPa, and the number of moles of epoxy oxime added was 10 moles until the desired addition of the epoxy oxime was completed.
  • the obtained dodecyl phenylethanol is used in a highly active and selective catalyst (CuO on silica gel). /Cr 2 0 3 catalytic system) heated to 240 ° C in the presence of conditions, a mixture of dimethylamine and hydrogen gas into the liquid phase system heated to the reaction temperature, the water formed by the reaction process, vaporized and carried away by hydrogen , the reaction is allowed to proceed completely. Filtered and dried, the final product was 223 g of dimercaptophenethyl dimethylamine.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des alcools alkylarylalkyle, leurs dérivés et leur procédé de préparation représentés par la formule (I) dans laquelle m, n, Ar et Q sont tels que définis dans la revendication 1. Le procédé consiste à: faire réagir un composé de formule (II) CmG2m+1-Ar et un composé de formule (III) CnH2n-1-X2, puis à l'hydrolyser afin d'obtenir le produit final. De tels composés font preuve d'une bonne fluidité à température ambiante et ont les caractéristiques des alcools très gras. Applications dans différents domaines en remplacement des alcools très gras.
PCT/CN2006/002151 2005-08-25 2006-08-23 Alcools alkylaryle, leurs derives et leur procede de preparation WO2007022718A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CNA2006800298476A CN101243029A (zh) 2005-08-25 2006-08-23 一种烷基芳基烷基醇及其相关产物

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
CN200510092891.9A CN1919438A (zh) 2005-08-25 2005-08-25 一种烷基苯烷基醇聚氧乙烯醚及其改性产物
CN200510092890.4 2005-08-25
CN200510092889.1A CN1919830A (zh) 2005-08-25 2005-08-25 一种烷基苯烷基胺及其应用
CN200510092890.4A CN1919831A (zh) 2005-08-25 2005-08-25 一种烷基萘烷基胺及其应用
CN200510092891.9 2005-08-25
CN200510092889.1 2005-08-25
CN200510093709.1 2005-08-29
CN 200510093709 CN1923873A (zh) 2005-08-29 2005-08-29 一种烷基萘烷基醇聚氧乙烯醚及其改性产物
CN200510104852.6 2005-09-23
CN200510104851.1 2005-09-23
CN 200510104852 CN1935760A (zh) 2005-09-23 2005-09-23 一种新型烷基苯烷基醇及其应用
CN 200510104851 CN1935759A (zh) 2005-09-23 2005-09-23 一种新型烷基萘烷基醇及其应用

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WO2007022718A1 true WO2007022718A1 (fr) 2007-03-01
WO2007022718B1 WO2007022718B1 (fr) 2007-04-05
WO2007022718A8 WO2007022718A8 (fr) 2007-05-18

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102531846A (zh) * 2010-12-17 2012-07-04 中国石油天然气股份有限公司 一种芳基脂肪醇及其制备方法

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US3896255A (en) * 1972-07-14 1975-07-22 Fuji Photo Film Co Ltd Recording sheet
US4613622A (en) * 1983-09-09 1986-09-23 Henkel Kommanditgesellschaft Auf Aktien Sebosuppressive preparations containing benzyl alcohol derivatives
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US4808572A (en) * 1985-12-06 1989-02-28 Ciba-Geigy Corporation α-Hydroxy thioethers
US5238832A (en) * 1992-06-08 1993-08-24 Board Of Governors Of Wayne State University Aryl aliphatic acids
JPH0641770A (ja) * 1992-07-27 1994-02-15 Daikin Ind Ltd シリコンウエハ表面の処理方法
US5604229A (en) * 1992-10-21 1997-02-18 Yoshitomi Pharmaceutical Industries, Ltd. 2-amino-1,3-propanediol compound and immunosuppressant
WO2003062252A1 (fr) * 2002-01-18 2003-07-31 Merck & Co., Inc. Agonistes du recepteur edg
US6605744B2 (en) * 1998-11-11 2003-08-12 Novartis Ag Production of 2-amin-2-[2-(2-(40-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols
DE10355169A1 (de) * 2003-11-26 2005-06-23 Studiengesellschaft Kohle Mbh Verfahren zur Herstellung von substituierten Arylverbindungen

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GB788881A (en) * 1954-10-29 1958-01-08 Rohm & Haas Improvements in quaternary ammonium compounds and use thereof
US3896255A (en) * 1972-07-14 1975-07-22 Fuji Photo Film Co Ltd Recording sheet
US4613622A (en) * 1983-09-09 1986-09-23 Henkel Kommanditgesellschaft Auf Aktien Sebosuppressive preparations containing benzyl alcohol derivatives
CN85108591A (zh) * 1984-07-27 1987-06-03 弗·哈夫曼—拉罗切有限公司 苯基-壬四烯酸衍生物的制备
US4808572A (en) * 1985-12-06 1989-02-28 Ciba-Geigy Corporation α-Hydroxy thioethers
US5238832A (en) * 1992-06-08 1993-08-24 Board Of Governors Of Wayne State University Aryl aliphatic acids
JPH0641770A (ja) * 1992-07-27 1994-02-15 Daikin Ind Ltd シリコンウエハ表面の処理方法
US5604229A (en) * 1992-10-21 1997-02-18 Yoshitomi Pharmaceutical Industries, Ltd. 2-amino-1,3-propanediol compound and immunosuppressant
US6605744B2 (en) * 1998-11-11 2003-08-12 Novartis Ag Production of 2-amin-2-[2-(2-(40-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols
WO2003062252A1 (fr) * 2002-01-18 2003-07-31 Merck & Co., Inc. Agonistes du recepteur edg
DE10355169A1 (de) * 2003-11-26 2005-06-23 Studiengesellschaft Kohle Mbh Verfahren zur Herstellung von substituierten Arylverbindungen

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KOIDE Y. ET AL.: "Development of Novel EDG3 Antagonists Using a 3D Database Search and Their Structure-Activity Relationships", JOURNAL OF MEDICINAL CHEMISTRY, vol. 45, no. 21, 2002, pages 4629 - 4638 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102531846A (zh) * 2010-12-17 2012-07-04 中国石油天然气股份有限公司 一种芳基脂肪醇及其制备方法

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