IL106872A - Production of cinnamic acid history - Google Patents

Production of cinnamic acid history

Info

Publication number: IL106872A
Authority: IL; Israel
Prior art keywords: alkyl; acid; amine; alkanoic acid; formula
Prior art date: 1992-09-03

Application number

IL10687293A

Other languages

English (en)

Hebrew (he)

Other versions

IL106872A0 (en

Original Assignee

Givaudan Roure Int

Priority date (The priority date 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 date listed.)

1992-09-03

Filing date

1993-09-02

Publication date

1996-10-16

1993-09-02 Application filed by Givaudan Roure Int filed Critical Givaudan Roure Int

1993-12-28 Publication of IL106872A0 publication Critical patent/IL106872A0/xx

1996-10-16 Publication of IL106872A publication Critical patent/IL106872A/en

Links

150000001851 cinnamic acid derivatives Chemical class 0.000 title claims abstract description 18
238000004519 manufacturing process Methods 0.000 title claims abstract description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 55
239000002253 acid Substances 0.000 claims abstract description 41
238000006243 chemical reaction Methods 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 28
229910052763 palladium Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000003054 catalyst Substances 0.000 claims abstract description 20
150000001412 amines Chemical class 0.000 claims abstract description 18
150000003863 ammonium salts Chemical class 0.000 claims abstract description 17
-1 heterocyclic amine Chemical class 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
150000003335 secondary amines Chemical class 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
125000005270 trialkylamine group Chemical group 0.000 claims abstract description 5
238000006845 Michael addition reaction Methods 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 22
SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 claims description 12
YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 12
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
125000005396 acrylic acid ester group Chemical group 0.000 claims description 10
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
150000001555 benzenes Chemical class 0.000 claims description 8
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
150000003235 pyrrolidines Chemical class 0.000 claims description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 3
229940043279 diisopropylamine Drugs 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
150000008424 iodobenzenes Chemical class 0.000 claims 1
239000002537 cosmetic Substances 0.000 abstract description 3
239000000516 sunscreening agent Substances 0.000 abstract description 3
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
125000001931 aliphatic group Chemical group 0.000 abstract 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
229930016911 cinnamic acid Natural products 0.000 abstract 1
235000013985 cinnamic acid Nutrition 0.000 abstract 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 5
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 3
QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
VEZIKIAGFYZTCI-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(OC)C=C1 VEZIKIAGFYZTCI-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
VDNROWDPOHVTJT-UHFFFAOYSA-N CC(CC(C)(C)C)(C)NC(C(=O)OCC(CCCC)CC)C Chemical compound CC(CC(C)(C)C)(C)NC(C(=O)OCC(CCCC)CC)C VDNROWDPOHVTJT-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
229940107816 ammonium iodide Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960001679 octinoxate Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
230000000475 sunscreen effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL10687293A 1992-09-03 1993-09-02 Production of cinnamic acid history IL106872A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH277192		1992-09-03
EP93111812		1993-07-23

Publications (2)

Publication Number	Publication Date
IL106872A0 IL106872A0 (en)	1993-12-28
IL106872A true IL106872A (en)	1996-10-16

Family

ID=25691362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10687293A IL106872A (en)	1992-09-03	1993-09-02	Production of cinnamic acid history

Country Status (10)

Country	Link
US (1)	US5457226A (da)
EP (1)	EP0612310B1 (da)
JP (1)	JP3539730B2 (da)
AT (1)	ATE144242T1 (da)
AU (1)	AU659570B2 (da)
DE (1)	DE69305491T2 (da)
DK (1)	DK0612310T3 (da)
ES (1)	ES2095073T3 (da)
IL (1)	IL106872A (da)
WO (1)	WO1994005621A1 (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5274171A (en) *	1992-01-22	1993-12-28	Givaudan-Roure Corporation	Process for the palladium catalyzed coupling of a diazonium salt with an olefinic bond
IL118817A (en) *	1995-08-24	1999-06-20	Bromine Compounds Ltd	Process for the preparation of octyl p-methoxy cinnamate
US5827805A (en) *	1996-02-29	1998-10-27	The Lubrizol Corporation	Condensates of alkyl phenols and glyoxal and products derived therefrom
US6624197B1 (en)	1998-05-08	2003-09-23	Calyx Therapeutics, Inc.	Diphenylethylene compounds
US20080108825A1 (en) *	1999-11-08	2008-05-08	Theracos, Inc.	Compounds for treatment of inflammation, diabetes and related disorders
US20020002200A1 (en) *	2000-02-04	2002-01-03	Bishwagit Nag	Novel diphenylethylene compounds
US7323496B2 (en) *	1999-11-08	2008-01-29	Theracos, Inc.	Compounds for treatment of inflammation, diabetes and related disorders
US20080103302A1 (en) *	2000-02-04	2008-05-01	Theracos, Inc.	Compounds for treatment of inflammation, diabetes and related disorders
US6413504B1 (en) *	2000-06-30	2002-07-02	Calyx Therapeutics, Inc.	Alpha-arylated cinnamic esters and 1,4-bis(alpha-carboxyl-beta-styryl)benzene esters an UV-blocking agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4965361A (en) *	1989-02-27	1990-10-23	Eastman Kodak Company	Preparation of 4-substituted aryl olefins
US4970332A (en) *	1989-03-09	1990-11-13	Mallinckrodt, Inc.	Process for producing 2-ethylhexyl-p-methoxycinnamate
JP2803386B2 (ja) *	1991-04-16	1998-09-24	株式会社明電舎	電縫管溶接管理方法およびその装置

1993
- 1993-08-27 DK DK93919198.7T patent/DK0612310T3/da active
- 1993-08-27 WO PCT/EP1993/002317 patent/WO1994005621A1/en not_active Ceased
- 1993-08-27 EP EP93919198A patent/EP0612310B1/en not_active Expired - Lifetime
- 1993-08-27 AU AU49545/93A patent/AU659570B2/en not_active Ceased
- 1993-08-27 DE DE69305491T patent/DE69305491T2/de not_active Expired - Fee Related
- 1993-08-27 US US08/232,131 patent/US5457226A/en not_active Expired - Lifetime
- 1993-08-27 AT AT93919198T patent/ATE144242T1/de not_active IP Right Cessation
- 1993-08-27 ES ES93919198T patent/ES2095073T3/es not_active Expired - Lifetime
- 1993-08-27 JP JP50684594A patent/JP3539730B2/ja not_active Expired - Fee Related
- 1993-09-02 IL IL10687293A patent/IL106872A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0612310B1 (en)	1996-10-16
AU659570B2 (en)	1995-05-18
JP3539730B2 (ja)	2004-07-07
DE69305491T2 (de)	1997-05-15
WO1994005621A1 (en)	1994-03-17
DE69305491D1 (de)	1996-11-21
EP0612310A1 (en)	1994-08-31
JPH07500847A (ja)	1995-01-26
IL106872A0 (en)	1993-12-28
DK0612310T3 (da)	1997-03-24
AU4954593A (en)	1994-03-29
US5457226A (en)	1995-10-10
ATE144242T1 (de)	1996-11-15
ES2095073T3 (es)	1997-02-01

Legal Events

Date	Code	Title
1997-03-18	FF	Patent granted
1997-07-13	KB	Patent renewed
2000-01-31	KB	Patent renewed
2000-07-16	HP	Change in proprietorship
2003-11-23	KB	Patent renewed
2008-06-05	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US6156925A (en)	2000-12-05	Process for the preparation of halogenated phenylmaloates
US4675442A (en)	1987-06-23	Method of making methacrylamides
EP0612310B1 (en)	1996-10-16	Process for the manufacture of cinnamic acid derivatives
HU211773B (en)	1995-12-28	Process for producing dialkyl-(2,3-pyridinedicarboxylate) derivatives
US5750766A (en)	1998-05-12	Process for the preparation of arylmalonates
JPH06298670A (ja)	1994-10-25	芳香族オレフィンの製造方法
US4310470A (en)	1982-01-12	Process for preparing a dialkyl propanediimidate dihydrohalide
US20020183515A1 (en)	2002-12-05	Asymmetric synthesis of a key intermediate for making benazepril and analogues thereof
HU225459B1 (en)	2006-12-28	Process for preparing substituted imidazopyridine compound
US5663365A (en)	1997-09-02	Process for the preparation of pyrazolones
US4567261A (en)	1986-01-28	Preparation of riboflavin
JPH0537140B2 (da)	1993-06-02
JPH02129159A (ja)	1990-05-17	Ｎ―置換アクリルアミドとｎ―置換メタクリルアミドの改良触媒合成方法
US5516932A (en)	1996-05-14	Halogenated cinnamic acids and esters thereof, processes for the preparation thereof and halogenated aryldiazonium salts
Goswami et al.	2001	Cycloaddition–hydrogenolysis strategy for the synthesis of 2, 4-disubstituted pyroglutamates
US5675034A (en)	1997-10-07	Process for preparing 2-(p-fluorophenyl)-2 methyl-propionic acid and 3-(p-fluorophenyl)-2-methylpropionic acid derivatives
GB2036723A (en)	1980-07-02	Mercaptoacylpiperazine carboxylic acid compounds
JPH07258192A (ja)	1995-10-09	メチル化合物の製造法
US20040249163A1 (en)	2004-12-09	Process for preparing beta-ketoester compound
JP4213244B2 (ja)	2009-01-21	ケト酸の精製方法
JP2991791B2 (ja)	1999-12-20	３−カルボキシアミド−５−ビニル−２−ピロリドンの製造方法
US6570015B2 (en)	2003-05-27	Process for producing 2-substituted thiopyrimidine-4-carboxylate
KITAGAWA et al.	1989	Convenient synthesis of amides, esters, and thioesters using 2, 2'-oxalyldi (2, 3-dihydro-3-oxobenzisosulfonazole)
US5322964A (en)	1994-06-21	Process for the preparation of alpha-aminoketone salts
JPH06157418A (ja)	1994-06-03	還元的脱ハロゲン化法