公开(公告)号：US09567283B2

公开(公告)日：2017-02-14

申请号：US15105047

申请日：2014-12-15

Applicant: RHODIA OPERATIONS

Inventor： Laurent Garel ,  Stephanie Normand ,  Stephanie Foucher ,  Dominique Horbez ,  Morad Assam

IPC: C07C51/47 ,  B01D15/08 ,  C07C51/41 ,  C07C45/29 ,  C07C45/61

CPC classification number: C07C51/47 ,  B01D15/08 ,  C07C45/29 ,  C07C45/512 ,  C07C45/61 ,  C07C51/367 ,  C07C51/41 ,  C07C59/52 ,  C07C47/58

Abstract: The invention describes a method for separating a mandelic compound in salified form from an aqueous reaction medium resulting from the condensation reaction of a hydroxylated aromatic compound with glyoxylic acid in a basic medium, said method comprising a) decanting said reaction medium in such a way as to recover an organic phase formed from the excess of said aromatic compound and an aqueous phase formed from said mandelic compound and a quantity of the excess of said aromatic compound and b) bringing said aqueous phase into contact with an adsorbent support, resulting in the selective adsorption of said aromatic compound and the recovery of an aqueous flow comprising said mandelic compound in salified form, which is subjected to an oxidation step before being converted into hydroxyaromatic aldehyde by electrodialysis.

Abstract translation: 本发明描述了一种从碱性介质中羟基化芳族化合物与乙醛酸的缩合反应产生的水性反应介质中分离成盐形态的扁桃酸化合物的方法，所述方法包括：a）将所述反应介质以如 回收由过量的所述芳族化合物形成的有机相和由所述扁桃酸化合物形成的水相和一定量的所述芳族化合物，以及b）使所述水相与吸附剂载体接触，导致选择性 所述芳香族化合物的吸附和含有所述扁桃酸化合物的盐水形式的水溶液的回收，所述盐水经过氧化步骤，然后通过电渗析转化为羟基芳族醛。

公开(公告)号：US08933274B2

公开(公告)日：2015-01-13

申请号：US14349842

申请日：2012-10-05

Applicant: Rhodia Operations

Inventor： Laurent Garel ,  Martine Vibert ,  Corine Cochennec ,  François Metz

IPC: C07C45/71 ,  C07C45/64

CPC classification number: C07C45/64 ,  C07C47/575

Abstract: A method for preparing a compound of formula (I) which is a vanillin derivative, of dimer type, called 3-(4-hydroxy-3-methoxybenzyl)-4-hydroxy-5-methoxybenzaldehyde, such method comprising a reaction of vanillin and vanillyl alcohol in the presence of a base.

Abstract translation: 制备称为3-（4-羟基-3-甲氧基苄基）-4-羟基-5-甲氧基苯甲醛的二聚体型香草醛衍生物的式（I）化合物的方法，该方法包括香草醛和 香草醇在碱的存在下。

公开(公告)号：US20230203345A1

公开(公告)日：2023-06-29

申请号：US17999522

申请日：2021-05-10

Applicant: RHODIA OPERATIONS

Inventor： Guillaume Gody ,  Isabelle Storet ,  Laurent Garel ,  Marie-Pierre Labeau

IPC: C09J5/04 ,  C08F220/06 ,  C08F212/14 ,  C09J5/02 ,  C08F2/10

CPC classification number: C09J5/04 ,  C08F220/06 ,  C08F212/24 ,  C09J5/02 ,  C08F2/10 ,  C09J2301/50 ,  C09J2400/166

Abstract: The instant invention concerns the use of polymers obtained by radical copolymerization of a mixture of (1) acrylic acid; (2) methacrylic acid; and (3) at least one allylcatechol selected from 4-allylbenzene-1,2-diol, 3-allylbenzene-1,2-diol; methylated forms thereof (eugenols); and mixtures thereof, for treating a metallic surface intended to be adhesive-bonded to another surface, in order to impart a resistance to the adhesive failure to the resulting bonding.

公开(公告)号：US10544081B2

公开(公告)日：2020-01-28

申请号：US15036871

申请日：2014-11-14

Applicant: RHODIA OPERATIONS

Inventor： Laurent Garel ,  Flavie Sarrazin ,  Olivier Back ,  Kevin Olivon ,  Mathieu Pucheault

IPC: C07C51/367 ,  C07C45/39

Abstract: A process for preparing an aromatic compound or compounds where at least one mandelic group —CHOH—COOH is described, comprising a reaction for condensation of at least one aromatic compound with glyoxylic acid or derivatives thereof, wherein said condensation reaction is carried out substantially in the absence of any acid or any base added to the reaction medium. The condensation reaction is followed by an oxidation reaction in order to obtain aromatic aldehyde.

公开(公告)号：US20170253547A1

公开(公告)日：2017-09-07

申请号：US15598400

申请日：2017-05-18

Applicant: Rhodia Operations ,  CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.)

Inventor： Thibaut Corre ,  Belen Albela ,  Laurent Bonneviot ,  Laurent Garel

IPC: C07C37/60 ,  B01J35/02 ,  C07C37/58 ,  C07C39/08 ,  B01J37/08 ,  B01J35/00 ,  C01B37/00 ,  B01J29/89

CPC classification number: C07C37/60 ,  B01J29/89 ,  B01J35/0013 ,  B01J35/006 ,  B01J35/023 ,  B01J37/08 ,  C01B37/005 ,  C01B39/065 ,  C01B39/36 ,  C01P2004/61 ,  C01P2006/12 ,  C01P2006/16 ,  C07C37/58 ,  C07C39/08

Abstract: The present invention relates to a process for hydroxylation of a compound of formula (I) by reacting the compound of formula (I) with an oxidizing agent, in the presence of a titanium silicalite zeolite prepared by crystallization preceded by a maturing step. The present invention also relates to a titanium silicalite zeolite and to the process for preparing same.

公开(公告)号：US09650322B2

公开(公告)日：2017-05-16

申请号：US15150028

申请日：2016-05-09

Applicant: Rhodia Operations

Inventor： Laurent Garel

IPC: C07C45/00 ,  C07C51/00 ,  C07C41/16 ,  C07C41/42 ,  C07C45/54 ,  C07C51/367

CPC classification number: C07C41/16 ,  C07C41/42 ,  C07C45/54 ,  C07C51/367 ,  Y02P20/582 ,  C07C43/23 ,  C07C59/64 ,  C07C47/58

Abstract: Processes may include producing at least one alkoxyhydroxybenzaldehyde compound from at least one hydroxyphenol compound, wherein processes include the steps of: (i) synthetizing at least one alkoxyphenol from said at least one hydroxyphenol in the presence of at least one O-alkylating agent; (ii) recovering said at least one alkoxyphenol and impurities, wherein said impurities includes a dialkoxybenzene compound; (iii) separating said dialkoxybenzene from the alkoxyphenol; (iv) condensing the alkoxyphenol with glyoxylic acid and obtaining the corresponding mandelic compound; (v) oxidizing said mandelic compound to give the corresponding alkoxyhydroxy-benzaldehyde; and (vi) recovering said alkoxyhydroxybenzaldehyde.

公开(公告)号：US09334216B2

公开(公告)日：2016-05-10

申请号：US14417015

申请日：2013-07-12

Applicant: RHODIA OPERATIONS

Inventor： Laurent Garel

IPC: C07C45/38 ,  C07C51/353 ,  C07C41/06 ,  C07C41/16 ,  C07C51/367 ,  C07C45/54

CPC classification number: C07C45/38 ,  C07C41/06 ,  C07C41/16 ,  C07C45/54 ,  C07C51/353 ,  C07C51/367 ,  Y02P20/582 ,  C07C43/23 ,  C07C59/64 ,  C07C47/58 ,  C07C47/575

Abstract: The invention relates to a method for producing alkoxyphenol from hydroxyphenol, comprising an O-alkylation reaction of at least one hydroxyphenol into at least one alkoxyphenol, said reaction being carried out using an O-alkylating agent, an aqueous solvent containing a Bröensted base, and an organic solvent, with a base/O-alkylating agent ratio of between 0.5 and 1.5 in moles of base per mole of O-alkylating agent, an O-alkylating agent/hydroxyphenol ratio of between 0.5 and 2 moles of O-alkylating agent per mole of hydroxyphenol, and an organic solvent/hydroxyphenol ratio of less than 280 mL, preferably between 10 and 250 mL and more preferably still between 50 and 150 mL of organic solvent per mole of hydroxyphenol. The invention also relates to a method for producing at least one alkoxy-hydroxybenzaldehyde from at least one hydroxyphenol compound.

Abstract translation: 本发明涉及一种由羟基苯酚生产烷氧基苯酚的方法，其中包括至少一种羟基苯酚与至少一种烷氧基苯酚的O-烷基化反应，所述反应使用O-烷基化试剂，含有布朗斯台德碱的含水溶剂和 一种有机溶剂，碱/ O-烷基化剂的比例为每摩尔O-烷基化剂0.5至1.5摩尔碱，O-烷基化剂/羟基苯酚的比例为0.5-2摩尔的O-烷基化剂/ 摩尔的羟基苯酚，有机溶剂/羟基苯酚的比例小于280mL，优选为10至250mL，更优选为50至150mL有机溶剂/摩尔羟基苯酚。 本发明还涉及从至少一种羟基苯酚化合物制备至少一种烷氧基 - 羟基苯甲醛的方法。

公开(公告)号：US09284247B2

公开(公告)日：2016-03-15

申请号：US14417010

申请日：2013-07-12

Applicant: RHODIA OPERATIONS

Inventor： Laurent Garel ,  Hubert Gayet

IPC: C07C45/32 ,  C07C45/38 ,  C07C41/09 ,  C07C41/42 ,  C07C45/39 ,  C07C51/367 ,  C07C51/353

CPC classification number: C07C45/38 ,  C07C41/09 ,  C07C41/42 ,  C07C45/39 ,  C07C51/353 ,  C07C51/367 ,  Y02P20/582 ,  C07C47/58 ,  C07C47/575 ,  C07C65/21 ,  C07C43/23

Abstract: The invention relates to a method for producing at least one alkoxy-hydroxybenzaldehyde (AHBA) from at least one hydroxyphenol (HP), said method being characterized in that it comprises the formation of at least one alkoxyphenol (AP) and alkyl-alkoxyphenol (AAP) and the separation (S) of AP from AAP, said separation (S) being carried out prior to obtaining AHBA.

Abstract translation: 本发明涉及从至少一种羟基苯酚（HP）制备至少一种烷氧基 - 羟基苯甲醛（AHBA）的方法，其特征在于其包括形成至少一种烷氧基苯酚（AP）和烷基 - 烷氧基苯酚（AAP ）和AP与AAP的分离（S），所述分离（S）在获得AHBA之前进行。

公开(公告)号：US20150183702A1

公开(公告)日：2015-07-02

申请号：US14417015

申请日：2013-07-12

Applicant: RHODIA OPERATIONS

Inventor： Laurent Garel

IPC: C07C45/38 ,  C07C51/353 ,  C07C41/06

CPC classification number: C07C45/38 ,  C07C41/06 ,  C07C41/16 ,  C07C45/54 ,  C07C51/353 ,  C07C51/367 ,  Y02P20/582 ,  C07C43/23 ,  C07C59/64 ,  C07C47/58 ,  C07C47/575

Abstract: The invention relates to a method for producing alkoxyphenol from hydroxyphenol, comprising an O-alkylation reaction of at least one hydroxyphenol into at least one alkoxyphenol, said reaction being carried out using an O-alkylating agent, an aqueous solvent containing a Bröensted base, and an organic solvent, with a base/O-alkylating agent ratio of between 0.5 and 1.5 in moles of base per mole of O-alkylating agent, an O-alkylating agent/hydroxyphenol ratio of between 0.5 and 2 moles of O-alkylating agent per mole of hydroxyphenol, and an organic solvent/hydroxyphenol ratio of less than 280 mL, preferably between 10 and 250 mL and more preferably still between 50 and 150 mL of organic solvent per mole of hydroxyphenol. The invention also relates to a method for producing at least one alkoxy-hydroxybenzaldehyde from at least one hydroxyphenol compound.

Abstract translation: 本发明涉及一种由羟基苯酚生产烷氧基苯酚的方法，其中包括至少一种羟基苯酚与至少一种烷氧基苯酚的O-烷基化反应，所述反应使用O-烷基化试剂，含有布朗斯台德碱的含水溶剂和 一种有机溶剂，碱/ O-烷基化剂的比例为每摩尔O-烷基化剂0.5至1.5摩尔碱，O-烷基化剂/羟基苯酚的比例为0.5-2摩尔的O-烷基化剂/ 摩尔的羟基苯酚，有机溶剂/羟基苯酚的比例小于280mL，优选为10至250mL，更优选为50至150mL有机溶剂/摩尔羟基苯酚。 本发明还涉及从至少一种羟基苯酚化合物制备至少一种烷氧基 - 羟基苯甲醛的方法。