JP4226906B2 - 低級オレフィンによる不飽和脂肪酸エステルまたは不飽和脂肪酸の複分解 - Google Patents
低級オレフィンによる不飽和脂肪酸エステルまたは不飽和脂肪酸の複分解 Download PDFInfo
- Publication number
- JP4226906B2 JP4226906B2 JP2002576183A JP2002576183A JP4226906B2 JP 4226906 B2 JP4226906 B2 JP 4226906B2 JP 2002576183 A JP2002576183 A JP 2002576183A JP 2002576183 A JP2002576183 A JP 2002576183A JP 4226906 B2 JP4226906 B2 JP 4226906B2
- Authority
- JP
- Japan
- Prior art keywords
- unsaturated fatty
- fatty acid
- catalyst
- metathesis
- olefin
- 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
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
- B01J31/1658—Polymer immobilised coordination complexes, e.g. organometallic complexes immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
- B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/825—Osmium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
上式で、MはRuまたはOsであり、Lはそれぞれ独立にMの結合と電荷の所要量を釣り合わせるいずれかの組合せで中性および陰イオン配位子から選択され、aは配位子Lの合計数を表す整数、好ましくは1〜約4であり、R′は水素、直鎖または枝分れアルキル、シクロアルキル、アリール、および置換アリール基から選択され、YはNomenclature of Inorganic Chemistry: Recommendations 1990, G. J. Leigh編, Blackwell Scientific Publications刊(1990)中にIUPACによって参照として載せられている周期表の15または16族中の元素の電子供与体基、別の呼び方でルイス塩基としても知られるものであり、Yはより好ましくはO、S、N、またはPであり、R″はそれぞれ独立にYの原子価を満たすのに十分な、好ましくはYが見掛け上中性になるように水素、アルキル、シクロアルキル、アリール、および置換アリール基から選択され、bはR″基の合計数を表す整数、好ましくは0〜約2であり、またZは二座配位子を形成するようにYとカルベン炭素(C)の両方に結合する有機二価基であって、この配位子はM原子と共に原子約4〜約8個の環を形成する。二座配位子は金属原子に対する2個の結合部位を有する。より好ましくはLはそれぞれ独立に、ハロゲン化物、最も好ましくはフッ化物、塩化物、臭化物、およびヨウ化物;シアン化物;チオシアン酸塩;式PR3のホスフィン;式NR3のアミン;水および式OR2のエーテル;式SR2のチオエーテル;および次式IIおよびIII
上式のいずれかのRはそれぞれ独立に、水素、アルキル、好ましくはC1〜15アルキル、シクロアルキル、好ましくはC3〜8シクロアルキル、アリール、好ましくはC6〜15アリール、置換アリール、好ましくはC6〜15置換アリール基からなる群から選択される。上記配位子Lのいずれかの混合物も式Iの任意の所与の種において使用することができる。より好ましくはR′は、水素、C1〜15アルキル、C3〜8シクロアルキル、およびC6〜15アリール基からなる群から選択される。より好ましくはR″それぞれ独立に、C1〜15アルキル、C3〜8シクロアルキル、およびC6〜15アリール基からなる群から選択される。好ましくはZは二価基、すなわち下記のエチレン(IV)、ビニレン(V)、フェニレン(VI)、置換ビニレン(VII)、置換フェニレン(VIII)、ナフチレン(IX)、置換ナフチレン(X)、ピペラジンジイル(XI)、ピペリジイル(XII)から選択され、
本発明の方法では第一生成物オレフィンおよびエステル官能基化または酸官能基化された第二生成物オレフィンの収率もまた、使用される特定のオレフィン試薬、特定の触媒、および特定のプロセス条件次第で変わる可能性がある。本発明の目的では「収率」は、供給材料中の不飽和脂肪酸エステルまたは不飽和脂肪酸の最初のモル数に対する形成される生成物オレフィンのモル百分率として定義することにする。一般にα-オレフィンの収率は約35モル%を超え、好ましくは約50モル%を超えるはずである。一般にエステル官能基化または酸官能基化α-オレフィンの収率は約35モル%を超え、好ましくは約50モル%を超えるはずである。
用語解説:
用語「配位子」は、錯体すなわち配位化合物中の中心原子、一般には金属原子に結合または付着した分子、イオン、または原子を意味するものとする。配位子は、中性、正、または負のいずれにも荷電することができる。配位子は、単一原子、単一イオン、または無機もしくは有機分子、例えばハロゲン化物またはトリアルキルホスフィンであることができる。
1平方インチ当たりのポンドの単位で表す圧力(ゲージ)(psig)は、次のようにpsigに6.895を乗ずることによりキロパスカル(kPa)の単位で表す圧力に換算される(例、50psig x 6.895 = 345kPa)。
下記の実施例は本発明の方法の例示として提供するが、どのようなやり方でも本発明を限定するものと解釈されるべきではない。当業技術者ならば、本明細書中の開示に照らして本発明の範囲内にある試薬、触媒、および複分解プロセス条件における変更形態を理解するはずである。
キレート配位子を有するルテニウム錯体を、J. S. Kingsbury等の論文、Journal of the American Chemical Society, 121 (1999), 791の文献の手順に従って調製した。具体的には調製された錯体は、式XIIIを有し、2つのハロゲン部分が塩化物である{ジクロロ[2(1-メチレンエトキシ-α-O)フェニル]メチレン-α-C](トリシクロヘキシルホスフィン)ルテニウム} であった。このキレート配位子は、その両方がRu原子と結合することができる1個のカルベン部分およびイソプロポキシ部分を有する。
実施例1のキレート化ルテニウム触媒の代わりに、式(XV)の[ジクロロ(フェニルメチレン)ビス(トリシクロヘキシルホスフィン)ルテニウム]を用いたことを除いて実施例1を繰り返した(式XV中のPCy3はトリシクロヘキシルホスフィンを表す)。この触媒はStrem Chemicals, Inc.から購入した。比較用の触媒中の配位子はすべて単座配位子であったことに注目されたい。
ポリスチレンで支持されたキレート化ルテニウム錯体を次のように調製した。まず架橋ポリスチレンを官能化した。脱ガスした無水ジメチルスルホキシド約30mLに溶かした2, 3-ジヒドロベンゾフラン(1.44g、11.9mモル)の溶液を、カニューレを介してナトリウムアミド(0.466g、11.9mモル)に室温で加えた。得られた淡黄色の溶液を室温で4時間攪拌した。次いでこの溶液を、脱ガスした無水テトラヒドロフラン50mLで膨潤させた架橋ポリスチレン樹脂(メリフィールド樹脂3.0g、1 g当たりCl 1.95mモル、1%架橋)にカニューレを介して加えた。得られた混合物を室温で夜通し攪拌した。次いでこの混合物を55℃で3時間加熱した。その後この混合物を室温まで冷却し、メタノール(100mL)を加えた。ポリマー生成物を濾過により単離し、テトラヒドロフラン、水、再びテトラヒドロフランで洗浄し、次いで真空中で夜通し乾燥して官能化した架橋ポリスチレンを得た。
トリシクロヘキシルホスフィン(キレート触媒1当量当たり1当量)を安定化配位子として工程に加えたことを除いて、実施例1の工程を繰り返した。実施例1と同じ工程条件下においてこの触媒は、2時間で1-デセンの収率53%、5時間で収率57%、また23時間で収率66%を達成した。第二オレフィン生成物9-デセン酸メチルも同様の結果を得た。
この実施例は、実施例1のキレート化ルテニウム触媒を用いたオレイン酸メチルの複分解に及ぼすエチレン圧の影響を示す。この実施例は実施例1と同様のやり方で行い、結果を表2に示した。
Claims (22)
- ルテニウムまたはオスミウムとキレート配位子とを含み、前記キレート配位子がカルベン部分と周期表の 15 族または 16 族の元素の電子供与体部分とを含む、複分解触媒の存在下において、第一オレフィン生成物およびエステル官能基化または酸官能基化された第二オレフィン生成物を調製するのに十分なプロセス条件下で不飽和脂肪酸エステルまたは不飽和脂肪酸を低級オレフィンと接触させるステップを含むオレフィンの複分解法。
- 前記不飽和脂肪酸が、8個を超え50個未満の炭素原子を含有し、かつ少なくとも1個の炭素−炭素二重結合を含有する、請求項1に記載の方法。
- 前記不飽和脂肪酸がオレイン酸である、請求項1または2に記載の方法。
- 前記不飽和脂肪酸エステルが、少なくとも1個の炭素−炭素二重結合を有するC8-50不飽和脂肪酸セグメントとC1-20アルコールセグメントとから誘導される、請求項1に記載の方法。
- 前記不飽和脂肪酸エステルがオレイン酸メチル又はグリセリドである、請求項1または4に記載の方法。
- 前記低級オレフィンがC2-8オレフィンである、請求項1〜5のいずれか一項に記載の方法。
- 前記低級オレフィンがエチレンであり、また、エチレンと不飽和脂肪酸エステルまたは不飽和脂肪酸とのモル比が0.8 / 1を超え、20 / 1未満である、請求項1〜6のいずれか一項に記載の方法。
- 前記複分解触媒が、式
上式で、MはRuまたはOsであり、Lはそれぞれ独立にMの結合と電荷の所要量を釣り合わせる組合せで中性および陰イオン配位子から選択され、aは1〜4の整数であり、R′は水素、アルキル、シクロアルキル、アリール、および置換アリール基から選択され、Yは周期表の15または16族中の元素であり、R″はそれぞれ独立にYの原子価を満たすのに十分な水素、アルキル、シクロアルキル、アリール、および置換アリール基から選択され、bは0〜2の整数であり、またZは二座配位子を形成するようにYとカルベン炭素(C)の両方に結合する有機二価基であって、この配位子がM原子と共に原子4〜8個の環を形成する、請求項1〜7のいずれか一項に記載の方法。 - Mがルテニウムであり、また場合により、Lがハロゲン化物およびトリアルキルホスフィンから選択され、Zがフェニレンである、請求項8に記載の方法。
- 前記触媒をシリカ類、アルミナ類、シリカ−アルミナ類、アルミノケイ酸塩類、チタニア類、ジルコニア、酸化マグネシウム、炭素、および架橋網状ポリマー樹脂類からなる群から選択される触媒担体で支持する、請求項1〜11のいずれか一項に記載の方法。
- 前記触媒を、触媒と担体の合計重量に対して触媒金属が0.01重量%を超え、20重量%未満である量で担体上に装填する、請求項12に記載の方法。
- トリアルキルホスフィン、トリアリールホスフィン、ジアリールアルキルホスフィン、アリールジアルキルホスフィン、エーテル、ピリジン、酸化ホスフィン、ホスフィナイト、ホスホナイト、ホスホルアミダイト、およびそれらの混合物からなる群より選択される安定化配位子をプロセスに加える、請求項1〜13のいずれか一項に記載の方法。
- 安定化配位子/触媒のモル比が0.05 / 1を超え、2.0 / 1未満である、請求項14に記載の方法。
- 前記方法を、0℃を超え150℃未満の温度、かつ5psig(34.5kPa)を超え1,000psig(6,895kPa)未満の合計圧力で行う、請求項1〜15のいずれか一項に記載の方法。
- 前記方法を不飽和脂肪酸エステルまたは不飽和脂肪酸/触媒のモル比が10 : 1を超え、10,000,000 : 1未満のバッチ式反応器中で行うか、あるいは前記方法を不飽和脂肪酸エステルまたは不飽和脂肪酸の重量毎時空間速度が0.04h-1を超え、100 h-1未満の連続または間欠フロー式反応器中で行う、請求項1〜16のいずれか一項に記載の方法。
- 前記脂肪酸エステルがオレイン酸メチルであるか、または前記脂肪酸がオレイン酸であり、その複分解生成物が1-デセンおよびそれぞれ9-デセン酸メチルまたは9-デセン酸である、請求項1〜17のいずれか一項に記載の方法。
- 前記キレート配位子が、カルベン部分および周期表の15または16族元素の第二供与体部分を含有する、請求項1〜18のいずれか一項に記載の方法。
- 有機金属錯体および触媒担体を含む不均一触媒組成物であって、前記有機金属錯体がルテニウムまたはオスミウム原子とキレート配位子とを含み、前記キレート配位子がカルベン部分と周期表の15族または16族の元素の電子供与体部分とを有し、前記カルベン部分と前記電子供与体部分の両方がルテニウムまたはオスミウム原子と結合しており、さらに、前記触媒担体が架橋ポリスチレン担体であり、前記有機金属錯体がベンジル結合を介して前記担体と結合している、不均一触媒組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27891401P | 2001-03-26 | 2001-03-26 | |
PCT/US2002/005894 WO2002076920A1 (en) | 2001-03-26 | 2002-02-27 | Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004525934A JP2004525934A (ja) | 2004-08-26 |
JP2004525934A5 JP2004525934A5 (ja) | 2005-07-28 |
JP4226906B2 true JP4226906B2 (ja) | 2009-02-18 |
Family
ID=23066924
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002576183A Expired - Fee Related JP4226906B2 (ja) | 2001-03-26 | 2002-02-27 | 低級オレフィンによる不飽和脂肪酸エステルまたは不飽和脂肪酸の複分解 |
Country Status (14)
Country | Link |
---|---|
US (2) | US7119216B2 (ja) |
EP (1) | EP1377537B1 (ja) |
JP (1) | JP4226906B2 (ja) |
KR (2) | KR100898876B1 (ja) |
CN (3) | CN100509155C (ja) |
AR (1) | AR033202A1 (ja) |
AU (1) | AU2002252124B2 (ja) |
BR (1) | BR0208639A (ja) |
CA (1) | CA2441980C (ja) |
DE (1) | DE60232062D1 (ja) |
MX (1) | MXPA03008323A (ja) |
PE (1) | PE20021029A1 (ja) |
RU (1) | RU2289568C2 (ja) |
WO (1) | WO2002076920A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8394361B1 (en) | 2001-12-21 | 2013-03-12 | Rhodia Operations | Stable surfactant compositions for suspending components |
Families Citing this family (90)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60232062D1 (de) | 2001-03-26 | 2009-06-04 | Dow Global Technologies Inc | Metathese-reaktion von ungesättigten fettsäurestern oder fettsäuren mit niedermolekularen olefinen |
EP1489106B1 (en) * | 2002-03-11 | 2012-05-09 | Japan Science and Technology Agency | Arene-ruthenium complexes immobilized on polymers, catalysts consisting of the complexes, and processes for organic syntheses with the same |
WO2003093215A1 (en) | 2002-04-29 | 2003-11-13 | Dow Global Technologies Inc. | Intergrated chemical processes for industrial utilization of seed oils |
US7960599B2 (en) * | 2003-01-13 | 2011-06-14 | Elevance Renewable Sciences, Inc. | Method for making industrial chemicals |
ATE400542T1 (de) * | 2003-10-09 | 2008-07-15 | Dow Global Technologies Inc | Verbessertes verfahren zur synthese ungesättigter alkohole |
DE102004033312A1 (de) * | 2004-07-08 | 2006-01-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Kontinuierliches Metatheseverfahren mit Ruthenium-Katalysatoren |
BRPI0514756A (pt) | 2004-09-02 | 2008-06-24 | Eastman Chem Co | processo para produzir ácidos dicarboxìlicos aromáticos, e, aparelhagem |
FR2878246B1 (fr) | 2004-11-23 | 2007-03-30 | Inst Francais Du Petrole | Procede de co-production d'olefines et d'esters par ethenolyse de corps gras insatures dans des liquides ioniques non-aqueux |
AU2006205023C1 (en) | 2005-01-10 | 2012-05-24 | Elevance Renewable Sciences, Inc. | Candle and candle wax containing metathesis and metathesis-like products |
EP1896385B1 (en) * | 2005-06-06 | 2013-08-28 | Dow Global Technologies LLC | Metathesis process for preparing an alpha, omega -functionalized olefin |
JP2008545021A (ja) * | 2005-07-01 | 2008-12-11 | オリカ オーストラリア プロプライアタリー リミティド | 架橋方法 |
WO2007081987A2 (en) | 2006-01-10 | 2007-07-19 | Elevance Renewable Sciences, Inc. | Method of making hydrogenated metathesis products |
FR2896498B1 (fr) * | 2006-01-24 | 2008-08-29 | Inst Francais Du Petrole | Procede de co-production d'olefines et de diesters ou de diacides a partir de corps gras insatures. |
RU2008132757A (ru) * | 2006-02-09 | 2010-03-20 | Елевансе Реневал Сайенсез, Инк. (US) | Антибактериальные составы, способы и системы |
WO2007092632A2 (en) * | 2006-02-09 | 2007-08-16 | Elevance Renawable Sciences, Inc. | Surface coating compositions and methods |
WO2007103460A2 (en) * | 2006-03-07 | 2007-09-13 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
CN102525829B (zh) * | 2006-03-07 | 2014-08-06 | 埃莱文斯可更新科学公司 | 含有复分解不饱和多元醇酯的组合物 |
CN101563434B (zh) * | 2006-07-12 | 2012-01-25 | 埃莱文斯可更新科学公司 | 包含复分解不饱和多元醇酯蜡的热熔性胶粘剂组合物 |
WO2008008440A2 (en) * | 2006-07-12 | 2008-01-17 | Elevance Renewable Sciences, Inc. | Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like |
WO2008010961A2 (en) | 2006-07-13 | 2008-01-24 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
RU2311231C1 (ru) * | 2006-08-15 | 2007-11-27 | ООО "Объединенный центр исследований и разработок" | Катализатор для получения эфиров акриловой кислоты по реакции метатезиса диалкилмалеатов (варианты) и каталитическая композиция на его основе |
DE102006040569A1 (de) * | 2006-08-30 | 2008-03-06 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuken |
US8614344B2 (en) * | 2006-10-13 | 2013-12-24 | Elevance Renewable Sciences, Inc. | Metathesis methods involving hydrogenation and compositions relating to same |
WO2008140468A2 (en) * | 2006-10-13 | 2008-11-20 | Elevance Renewable Sciences, Inc. | METHODS OF MAKING α, ω -DICARBOXYLIC ACID ALKENE DERIVATIVES BY METATHESIS |
WO2008048520A2 (en) * | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
WO2008048522A1 (en) * | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making monounsaturated functionalized alkene compounds by metathesis |
CN106083579A (zh) * | 2006-10-13 | 2016-11-09 | 埃莱文斯可更新科学公司 | 通过烯烃复分解由内烯烃合成末端烯烃的方法 |
US7691258B2 (en) * | 2007-06-04 | 2010-04-06 | Emirates National Oil Company Limited (Enoc) Llc | Process for treating hydrocarbon liquid compositions |
WO2009003085A1 (en) * | 2007-06-27 | 2008-12-31 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins via metathesis |
MX2010001614A (es) | 2007-08-09 | 2010-04-22 | Elevance Renewable Sciences | Metodos quimicos para tratar un material de alimentacion para la metatesis. |
FR2921362B1 (fr) * | 2007-09-20 | 2012-09-21 | Arkema France | Procede de synthese d'acides gras omega-insatures |
US20090203950A1 (en) * | 2008-02-12 | 2009-08-13 | Halsey Richard B | Metathesis process using a fluidized bed reactor |
EP2350159A1 (en) | 2008-10-31 | 2011-08-03 | Dow Global Technologies LLC | Olefin metathesis process employing bimetallic ruthenium complex with bridging hydrido ligands |
EP2352712B1 (en) * | 2008-11-26 | 2018-06-27 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through metathesis reactions |
CN102227489B (zh) * | 2008-11-26 | 2015-04-15 | 埃莱文斯可更新科学公司 | 通过氧解反应用天然油原料制备喷气式发动机燃料的方法 |
US8071799B2 (en) | 2009-01-29 | 2011-12-06 | Energy & Environmental Research Center Foundation | Chain-selective synthesis of fuel components and chemical feedstocks |
US9169447B2 (en) * | 2009-10-12 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9382502B2 (en) | 2009-10-12 | 2016-07-05 | Elevance Renewable Sciences, Inc. | Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks |
US9000246B2 (en) | 2009-10-12 | 2015-04-07 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US8735640B2 (en) * | 2009-10-12 | 2014-05-27 | Elevance Renewable Sciences, Inc. | Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks |
US9051519B2 (en) | 2009-10-12 | 2015-06-09 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US9222056B2 (en) | 2009-10-12 | 2015-12-29 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9365487B2 (en) | 2009-10-12 | 2016-06-14 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US9175231B2 (en) | 2009-10-12 | 2015-11-03 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils and methods of producing fuel compositions |
RU2565057C2 (ru) * | 2009-10-12 | 2015-10-20 | Елевансе Реневабле Сайенсез, Инк. | Способы очистки и производства топлива из натурального масляного исходного сырья |
US8329921B2 (en) | 2009-11-09 | 2012-12-11 | Exxonmobil Chemical Patents Inc. | Metathesis catalyst and process for use thereof |
US8237003B2 (en) | 2009-11-09 | 2012-08-07 | Exxonmobil Chemical Patents Inc. | Metathesis catalyst and process for use thereof |
US8809563B2 (en) | 2009-11-09 | 2014-08-19 | Exxonmobil Chemical Patents Inc. | Metathesis catalyst and process for use thereof |
EP2498909B1 (en) * | 2009-11-09 | 2014-08-27 | ExxonMobil Chemical Patents Inc. | Metathesis catalyst and process for use thereof |
US9024034B2 (en) * | 2009-11-09 | 2015-05-05 | Exxonmobil Chemical Patents Inc. | Metathesis catalysts and processes for use thereof |
CA2785897C (en) | 2010-02-12 | 2014-01-28 | Exxonmobil Chemical Patents Inc. | Metathesis catalyst and process for use thereof |
US9115076B2 (en) | 2010-04-26 | 2015-08-25 | The United States Of America, As Represented By The Secretary Of Agriculture | Process for preparing saturated branched chain fatty acids |
WO2011136903A1 (en) * | 2010-04-26 | 2011-11-03 | The United States Of America As Represented By The Secretary Of Agriculture | Process for preparing saturated branched chain fatty acids |
US8748641B2 (en) | 2010-05-05 | 2014-06-10 | The United States Of America, As Represented By The Secretary Of Agriculture | Process for preparing saturated branched chain fatty acids |
JP5868962B2 (ja) | 2010-05-28 | 2016-02-24 | ソラザイム, インコーポレイテッドSolazyme Inc | 組み換え従属栄養性微生物から産生された用途に応じた油 |
CA2809353C (en) | 2010-08-31 | 2019-03-19 | Biosynthetic Technologies, Llc | High- and low-viscosity estolide base oils and lubricants |
US8227371B2 (en) | 2010-09-24 | 2012-07-24 | Exxonmobil Chemical Patents Inc. | Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof |
US9249436B2 (en) | 2011-02-02 | 2016-02-02 | Solazyme, Inc. | Tailored oils produced from recombinant oleaginous microorganisms |
US20120289617A1 (en) * | 2011-05-10 | 2012-11-15 | Saudi Arabian Oil Company | Hybrid Catalyst for Olefin Metathesis |
US9181360B2 (en) | 2011-08-12 | 2015-11-10 | Exxonmobil Chemical Patents Inc. | Polymers prepared by ring opening / cross metathesis |
AU2012355690B2 (en) | 2011-12-19 | 2017-02-02 | Biosynthetic Technologies, Llc | Processes for preparing estolide base oils and oligomeric compounds that include cross metathesis |
US9169174B2 (en) | 2011-12-22 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9133416B2 (en) | 2011-12-22 | 2015-09-15 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9139493B2 (en) | 2011-12-22 | 2015-09-22 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
CA2861848A1 (en) | 2012-01-10 | 2013-06-28 | Monika Mujkic | Renewable fatty acid waxes and methods of making |
GB201204715D0 (en) | 2012-03-18 | 2012-05-02 | Croda Int Plc | Metathesis of olefins using ruthenium-based catalytic complexes |
ES2744868T3 (es) | 2012-04-18 | 2020-02-26 | Corbion Biotech Inc | Aceites hechos a medida |
JPWO2013175894A1 (ja) * | 2012-05-21 | 2016-01-12 | 日本ゼオン株式会社 | 架橋環状オレフィン樹脂フィルム、積層体及びそれらの製造方法 |
US8586771B1 (en) | 2012-06-18 | 2013-11-19 | Biosynthetic Technologies, Llc | Processes of preparing estolide compounds that include removing sulfonate residues |
AU2013277107B2 (en) | 2012-06-20 | 2018-03-08 | Wilmar Trading Pte Ltd | Natural oil metathesis compositions |
PL400162A1 (pl) * | 2012-07-27 | 2014-02-03 | Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia | Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy |
JP6460994B2 (ja) * | 2012-10-09 | 2019-01-30 | エレヴァンス リニューアブル サイエンシズ インコーポレイテッドElevance Renewable Sciences, Inc. | 天然油原料から二塩基酸エステル類及び二塩基酸類を精製及び製造する方法 |
US9388098B2 (en) | 2012-10-09 | 2016-07-12 | Elevance Renewable Sciences, Inc. | Methods of making high-weight esters, acids, and derivatives thereof |
BR112015026948A8 (pt) | 2013-04-26 | 2017-10-03 | Solazyme Inc | "composições, lubrificante, tensoativo, solvente, formulação de limpeza, composição de borracha reticulável ou reticulada, tira de pneu, espuma de poliuretano e seu método de preparação |
SG10201802834YA (en) | 2013-10-04 | 2018-05-30 | Terravia Holdings Inc | Tailored oils |
US20160244397A1 (en) * | 2015-02-20 | 2016-08-25 | Biosynthetic Technologies, Llc. | Processes for preparing estolide base oils and biobased compounds that include ethyleneolysis |
MX2017012800A (es) | 2015-04-06 | 2018-04-11 | Terravia Holdings Inc | Microalgas oleaginosas que tienen una ablación de lpaat. |
CN105419941B (zh) * | 2015-11-18 | 2017-08-22 | 天津斯瑞吉高新科技研究院有限公司 | 从棉籽油来制取高附加值产品的一种有效预处理方法 |
CN114106057B (zh) | 2016-10-19 | 2023-06-23 | 优美科股份公司及两合公司 | Ru亚烷基络合物的合成与表征 |
JP7143289B2 (ja) * | 2016-10-25 | 2022-09-28 | ウィルマー トレーディング ピーティーイー リミテッド | 再生可能に得られたポリアミド、およびその製造方法 |
US11471867B2 (en) * | 2017-06-23 | 2022-10-18 | Gwangju Institute Of Science And Technology | Ligand for forming ruthenium complex, ruthenium complex catalyst, production method therefor and use thereof |
CN109364998B (zh) * | 2018-10-15 | 2021-07-06 | 天津科技大学 | 一种用于烯烃复分解反应的催化剂及其制备和应用方法 |
EP3650436A1 (en) | 2018-11-06 | 2020-05-13 | Skotan S.A. | Method of preparing a mixture of 9-decenoic acid ethyl and 1-decene in an ethenolysis reaction from a raw material of technical purity |
EP4115975A4 (en) * | 2020-03-03 | 2024-05-15 | Takasago Perfumery Co Ltd | ACTIVATED CARBON CATALYST WITH RUTHENIUM COMPLEX ADSORBED THEREOF AND METHOD FOR PRODUCING A REDUCTION PRODUCT USING THE SAME |
EP4182423A1 (de) | 2020-07-17 | 2023-05-24 | Werner & Mertz GmbH | Verfahren zur herstellung eines biobasierten produkts, entsprechendes produkt und verwendungen |
DE102020119024A1 (de) | 2020-07-17 | 2022-01-20 | Werner & Mertz Gmbh | Verfahren zur Herstellung eines biobasierten Produkts, entsprechendes Produkt und Verwendungen |
EP3974499A1 (en) | 2020-09-28 | 2022-03-30 | Indian Oil Corporation Limited | Production of linear alpha olefins |
CN112876360A (zh) * | 2021-01-25 | 2021-06-01 | 南京工业大学 | 一种植物油多元醇及其制备方法与应用 |
BR102021002671A2 (pt) | 2021-02-11 | 2022-08-16 | Petróleo Brasileiro S.A. - Petrobras | Processo para coprodução de olefinas e ésteres c10 a c13 a partir de ésteres de ácidos graxos metílicos |
US11858872B2 (en) * | 2021-03-30 | 2024-01-02 | ExxonMobil Technology and Engineering Company | High yield jet fuel from mixed fatty acids |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE281594C (ja) | ||||
JPS5677243A (en) | 1979-11-29 | 1981-06-25 | Takasago Corp | Production of 9-octadecenedioic acid diester |
EP0328230A3 (en) | 1981-11-19 | 1990-03-21 | Fuji Oil Company, Limited | Method for the modification of fats and oils |
EP0084437A1 (en) | 1982-01-13 | 1983-07-27 | BP Chemicals Limited | Dismutation of functionalised olefins |
US4560792A (en) * | 1982-07-20 | 1985-12-24 | Phillips Petroleum Company | Disproportionation of functional olefins |
CA1219596A (en) | 1982-07-20 | 1987-03-24 | Dennis S. Banasiak | Disproportionation of functional olefins |
US4545941A (en) * | 1983-06-20 | 1985-10-08 | A. E. Staley Manufacturing Company | Co-metathesis of triglycerides and ethylene |
DE3612539A1 (de) * | 1986-04-14 | 1987-10-15 | Huels Chemische Werke Ag | Verfahren zur herstellung von technisch reinem, chlorfreiem cyclohexadecadien |
US4943397A (en) * | 1988-09-22 | 1990-07-24 | Shell Oil Company | Metathesis of functional olefins |
US5342985A (en) * | 1988-12-10 | 1994-08-30 | Hoechst Ag | Organic derivatives of rhenium oxides and their preparation and use for the metathesis of olefins |
JPH0366725A (ja) | 1989-08-04 | 1991-03-22 | Japan Synthetic Rubber Co Ltd | 重合体の製造方法 |
DE4006540A1 (de) * | 1990-03-02 | 1991-09-05 | Huels Chemische Werke Ag | Katalysatoren fuer die metathese von olefinen und funktionalisierten olefinen |
DE4006539A1 (de) * | 1990-03-02 | 1991-09-05 | Huels Chemische Werke Ag | Verfahren zur metathese von olefinen und funktionalisierten olefinen |
EP0522067B1 (de) | 1990-03-28 | 1995-06-28 | Hoechst Aktiengesellschaft | Verwendung von organischen derivaten von rheniumoxiden als katalysatoren zur äthenolytischen metathese olefinischer verbindungen und verfahren zur äthenolytischen metathese von olefinischen verbindungen mit hilfe dieser katalysatoren |
DE4107056A1 (de) | 1991-03-06 | 1992-09-10 | Huels Chemische Werke Ag | Rheniumkatalysatoren fuer die metathese von olefinen und funktionalisierten olefinen |
US5312940A (en) * | 1992-04-03 | 1994-05-17 | California Institute Of Technology | Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization |
WO1996004289A1 (en) * | 1992-04-03 | 1996-02-15 | California Institute Of Technology | High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof |
US5352812A (en) * | 1993-07-08 | 1994-10-04 | E. I. Du Pont De Nemours And Company | Metathesis of acyclic olefins using an iridium/silver catalyst composition |
US5539060A (en) * | 1993-07-30 | 1996-07-23 | Nippon Zeon Co., Ltd. | Method for hydrogenation of metathesis polymers |
US5831108A (en) | 1995-08-03 | 1998-11-03 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
US6225426B1 (en) * | 1996-04-10 | 2001-05-01 | Uniroyal Chemical Company, Inc. | Process for producing polyolefin elastomer employing a metallocene catalyst |
US6159890A (en) | 1996-04-30 | 2000-12-12 | Bp Amoco Corporation | Ruthenium-containing catalyst system for olefin metathesis |
US6156692A (en) * | 1996-04-30 | 2000-12-05 | Bp Amoco Corporation | Ruthenium-containing catalyst composition for olefin metathesis |
DE19654074C2 (de) * | 1996-12-23 | 2001-01-25 | Bayer Ag | Verfahren zur Herstellung hydrierter ringgeöffneter Metathesepolymeren |
US6197894B1 (en) * | 1997-05-28 | 2001-03-06 | Mitsui Chemicals, Inc. | Preparation of hydrogenated product of cyclic olefin ring-opening metathesis polymer |
US6306987B1 (en) * | 1997-06-27 | 2001-10-23 | Ciba Specialty Chemicals Corporation | Ruthenium and osmium catalysts |
DE19815275B4 (de) * | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
DE69941219D1 (de) | 1998-09-10 | 2009-09-17 | Univ New Orleans Foundation | Katalysatorkomplex mit phenylindenyliden-ligand |
US6426419B1 (en) | 1999-03-31 | 2002-07-30 | California Institute Of Technology | Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity |
CA2372746C (en) | 1999-05-24 | 2012-10-02 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
DE10041345A1 (de) | 2000-08-23 | 2002-03-07 | Basf Ag | Verfahren zur Synthese von terminalen Olefinen mit enger Molgewichtsverteilung |
DE60232062D1 (de) | 2001-03-26 | 2009-06-04 | Dow Global Technologies Inc | Metathese-reaktion von ungesättigten fettsäurestern oder fettsäuren mit niedermolekularen olefinen |
WO2003093215A1 (en) | 2002-04-29 | 2003-11-13 | Dow Global Technologies Inc. | Intergrated chemical processes for industrial utilization of seed oils |
US7147749B2 (en) | 2002-09-30 | 2006-12-12 | Tokyo Electron Limited | Method and apparatus for an improved upper electrode plate with deposition shield in a plasma processing system |
ATE400542T1 (de) | 2003-10-09 | 2008-07-15 | Dow Global Technologies Inc | Verbessertes verfahren zur synthese ungesättigter alkohole |
EP1817097A2 (en) | 2004-10-21 | 2007-08-15 | Dow Gloval Technologies Inc. | Membrane separation of a metathesis reaction mixture |
EP1896385B1 (en) | 2005-06-06 | 2013-08-28 | Dow Global Technologies LLC | Metathesis process for preparing an alpha, omega -functionalized olefin |
US8048961B2 (en) | 2006-08-25 | 2011-11-01 | Dow Global Technologies Llc | Production of metathesis products by amorphous polymer segment interchange |
US8557921B2 (en) | 2006-08-25 | 2013-10-15 | Dow Global Technologies Llc | Production of meta-block copolymers by polymer segment interchange |
US8530579B2 (en) | 2006-08-25 | 2013-09-10 | Dow Global Technologies Llc | Production of metathesis products by high melting polymer segment interchange |
US7956132B2 (en) | 2006-08-25 | 2011-06-07 | Dow Global Technologies Llc | Production of telechelic compounds by metathesis depolymerization |
-
2002
- 2002-02-27 DE DE60232062T patent/DE60232062D1/de not_active Expired - Lifetime
- 2002-02-27 RU RU2003131325/04A patent/RU2289568C2/ru active
- 2002-02-27 AU AU2002252124A patent/AU2002252124B2/en not_active Expired
- 2002-02-27 MX MXPA03008323A patent/MXPA03008323A/es not_active Application Discontinuation
- 2002-02-27 WO PCT/US2002/005894 patent/WO2002076920A1/en active Application Filing
- 2002-02-27 JP JP2002576183A patent/JP4226906B2/ja not_active Expired - Fee Related
- 2002-02-27 CA CA2441980A patent/CA2441980C/en not_active Expired - Lifetime
- 2002-02-27 CN CNB2005101080146A patent/CN100509155C/zh not_active Expired - Lifetime
- 2002-02-27 CN CN028073797A patent/CN1501906B/zh not_active Expired - Lifetime
- 2002-02-27 KR KR1020087012895A patent/KR100898876B1/ko active IP Right Grant
- 2002-02-27 EP EP02721181A patent/EP1377537B1/en not_active Revoked
- 2002-02-27 KR KR1020037012499A patent/KR100869981B1/ko active IP Right Grant
- 2002-02-27 BR BR0208639-5A patent/BR0208639A/pt not_active Application Discontinuation
- 2002-02-27 US US10/469,321 patent/US7119216B2/en not_active Expired - Lifetime
- 2002-02-27 CN CN201110031972.3A patent/CN102146031B/zh not_active Expired - Lifetime
- 2002-03-25 AR ARP020101077A patent/AR033202A1/es active IP Right Grant
- 2002-03-26 PE PE2002000236A patent/PE20021029A1/es not_active Application Discontinuation
-
2003
- 2003-09-26 US US10/528,472 patent/US7696398B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8394361B1 (en) | 2001-12-21 | 2013-03-12 | Rhodia Operations | Stable surfactant compositions for suspending components |
Also Published As
Publication number | Publication date |
---|---|
EP1377537B1 (en) | 2009-04-22 |
KR100869981B1 (ko) | 2008-11-24 |
DE60232062D1 (de) | 2009-06-04 |
CA2441980C (en) | 2011-07-19 |
CN102146031A (zh) | 2011-08-10 |
RU2289568C2 (ru) | 2006-12-20 |
US20050070750A1 (en) | 2005-03-31 |
JP2004525934A (ja) | 2004-08-26 |
EP1377537A1 (en) | 2004-01-07 |
KR20030086323A (ko) | 2003-11-07 |
MXPA03008323A (es) | 2003-12-11 |
CN1748864A (zh) | 2006-03-22 |
AU2002252124B2 (en) | 2007-09-06 |
CA2441980A1 (en) | 2002-10-03 |
KR20080066829A (ko) | 2008-07-16 |
PE20021029A1 (es) | 2002-11-07 |
KR100898876B1 (ko) | 2009-05-25 |
RU2003131325A (ru) | 2005-01-27 |
US20060167326A1 (en) | 2006-07-27 |
CN102146031B (zh) | 2014-08-06 |
CN1501906A (zh) | 2004-06-02 |
WO2002076920A1 (en) | 2002-10-03 |
US7119216B2 (en) | 2006-10-10 |
AR033202A1 (es) | 2003-12-10 |
CN1501906B (zh) | 2012-07-04 |
BR0208639A (pt) | 2004-08-10 |
CN100509155C (zh) | 2009-07-08 |
US7696398B2 (en) | 2010-04-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4226906B2 (ja) | 低級オレフィンによる不飽和脂肪酸エステルまたは不飽和脂肪酸の複分解 | |
AU2002252124A1 (en) | Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins | |
JP4779121B2 (ja) | 不飽和アルコールの改良合成方法 | |
US6803429B2 (en) | Selective ring-opening cross-metathesis of cycloolefins | |
CA2442368C (en) | Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts | |
US8227371B2 (en) | Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof | |
WO2004035596A1 (en) | Ruthenium complexes as (pre)catalysts for metathesis reactions | |
WO2012040088A2 (en) | A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof | |
WO2012166259A2 (en) | A novel class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050225 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080201 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080219 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080516 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080523 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080818 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20081028 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20081127 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111205 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4226906 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111205 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121205 Year of fee payment: 4 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121205 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131205 Year of fee payment: 5 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |