JPS63198645A - ブラシル酸ジ低級アルキルエステルの製造法 - Google Patents

ブラシル酸ジ低級アルキルエステルの製造法

Info

Publication number: JPS63198645A
Authority: JP; Japan
Prior art keywords: lower alkyl; brassylic acid; alkyl ester; halogenated; reaction
Prior art date: 1987-02-13
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.): Granted

Application number

JP62029696A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0417939B2 (cs

Inventor

Toshiaki Sakaguchi

坂口　登志昭

Toru Watanabe

徹渡辺

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takasago International Corp

Takasago Corp

Original Assignee

Takasago Perfumery Industry Co

Takasago Corp

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.)

1987-02-13

Filing date

1987-02-13

Publication date

1988-08-17

1987-02-13 Application filed by Takasago Perfumery Industry Co, Takasago Corp filed Critical Takasago Perfumery Industry Co

1987-02-13 Priority to JP62029696A priority Critical patent/JPS63198645A/ja

1988-08-17 Publication of JPS63198645A publication Critical patent/JPS63198645A/ja

1992-03-26 Publication of JPH0417939B2 publication Critical patent/JPH0417939B2/ja

Status Granted legal-status Critical Current

Links

DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 title claims abstract description 25
125000005907 alkyl ester group Chemical group 0.000 title claims abstract description 23
238000004519 manufacturing process Methods 0.000 title claims description 10
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 title description 15
-1 undecylenic acid ester Chemical class 0.000 claims abstract description 23
229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 12
239000007868 Raney catalyst Substances 0.000 claims abstract description 10
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims abstract description 10
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 5
150000003512 tertiary amines Chemical class 0.000 claims description 12
238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 24
238000006243 chemical reaction Methods 0.000 abstract description 18
239000000126 substance Substances 0.000 abstract description 13
239000002994 raw material Substances 0.000 abstract description 8
239000001257 hydrogen Substances 0.000 abstract description 7
229910052739 hydrogen Inorganic materials 0.000 abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
241000402754 Erythranthe moschata Species 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 4
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 abstract description 4
239000002904 solvent Substances 0.000 abstract description 4
229960002703 undecylenic acid Drugs 0.000 abstract description 4
150000001412 amines Chemical class 0.000 abstract description 3
239000004359 castor oil Substances 0.000 abstract description 2
235000019438 castor oil Nutrition 0.000 abstract description 2
239000007789 gas Substances 0.000 abstract description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract description 2
238000005979 thermal decomposition reaction Methods 0.000 abstract description 2
238000004517 catalytic hydrocracking Methods 0.000 abstract 2
150000001875 compounds Chemical class 0.000 abstract 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
239000002304 perfume Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
238000001819 mass spectrum Methods 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000000034 method Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
IFKANGOXGBPILW-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-6-carboxylic acid Chemical compound O1CCCC2=CC(C(=O)O)=CC=C21 IFKANGOXGBPILW-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000003205 fragrance Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
WWSBQOYADFGDQE-UHFFFAOYSA-N tridecanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCCCCCC(=O)OC WWSBQOYADFGDQE-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
VATGVFHNUYPZDV-UHFFFAOYSA-N dimethyl 4-chlorotridecanedioate Chemical compound COC(=O)CCCCCCCCC(Cl)CCC(=O)OC VATGVFHNUYPZDV-UHFFFAOYSA-N 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
ANLABNUUYWRCRP-UHFFFAOYSA-N 1-(4-nitrophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C#N)CCCC1 ANLABNUUYWRCRP-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
244000309464 bull Species 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
HVKQOPBXSVRTFF-UHFFFAOYSA-N n,n-dibutyl-2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN(CCCC)CCCC HVKQOPBXSVRTFF-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 2
XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 2
ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
FXNFFCMITPHEIT-UHFFFAOYSA-N Ethyl 10-undecenoate Chemical compound CCOC(=O)CCCCCCCCC=C FXNFFCMITPHEIT-UHFFFAOYSA-N 0.000 description 1
XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
238000006612 Kolbe reaction Methods 0.000 description 1
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
235000019484 Rapeseed oil Nutrition 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 1
150000001954 decanoic acid esters Chemical class 0.000 description 1
KYACNNYLFZGWTO-UHFFFAOYSA-N diethyl tridecanedioate Chemical compound CCOC(=O)CCCCCCCCCCCC(=O)OCC KYACNNYLFZGWTO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000007342 radical addition reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229940075466 undecylenate Drugs 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

JP62029696A 1987-02-13 1987-02-13 ブラシル酸ジ低級アルキルエステルの製造法 Granted JPS63198645A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP62029696A JPS63198645A (ja)	1987-02-13	1987-02-13	ブラシル酸ジ低級アルキルエステルの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62029696A JPS63198645A (ja)	1987-02-13	1987-02-13	ブラシル酸ジ低級アルキルエステルの製造法

Publications (2)

Publication Number	Publication Date
JPS63198645A true JPS63198645A (ja)	1988-08-17
JPH0417939B2 JPH0417939B2 (cs)	1992-03-26

Family

ID=12283271

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62029696A Granted JPS63198645A (ja)	1987-02-13	1987-02-13	ブラシル酸ジ低級アルキルエステルの製造法

Country Status (1)

Country	Link
JP (1)	JPS63198645A (cs)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1323541A2 (en)	2001-12-27	2003-07-02	Eastman Kodak Company	Thermal dye transfer receiver element with microvoided support
EP1431055A2 (en)	2002-12-20	2004-06-23	Eastman Kodak Company	Voided polyester sheet for thermal recording materials
EP1452336A1 (en)	2003-02-26	2004-09-01	Eastman Kodak Company	Therma dye-transfer receiver element with microvoided layer
US7078367B2 (en)	2004-02-20	2006-07-18	Eastman Kodak Company	Thermal-dye-transfer receiver element with polylactic-acid-based sheet material

1987
- 1987-02-13 JP JP62029696A patent/JPS63198645A/ja active Granted

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1323541A2 (en)	2001-12-27	2003-07-02	Eastman Kodak Company	Thermal dye transfer receiver element with microvoided support
EP1431055A2 (en)	2002-12-20	2004-06-23	Eastman Kodak Company	Voided polyester sheet for thermal recording materials
US6867168B2 (en)	2002-12-20	2005-03-15	Eastman Kodak Company	Microbead and immiscible polymer voided polyester for thermal imaging medias
EP1452336A1 (en)	2003-02-26	2004-09-01	Eastman Kodak Company	Therma dye-transfer receiver element with microvoided layer
US6890884B2 (en)	2003-02-26	2005-05-10	Eastman Kodak Company	Thermal dye-transfer receiver element with microvoided layer
US7078367B2 (en)	2004-02-20	2006-07-18	Eastman Kodak Company	Thermal-dye-transfer receiver element with polylactic-acid-based sheet material

Also Published As

Publication number	Publication date
JPH0417939B2 (cs)	1992-03-26

Publication	Publication Date	Title
JPH1192423A (ja)	1999-04-06	トリフルオロ酢酸及びクロロジフルオロ酢酸のメチルエステル又はエチルエステルの製造方法
CN114096513A (zh)	2022-02-25	新的季铵化合物
JPS63198645A (ja)	1988-08-17	ブラシル酸ジ低級アルキルエステルの製造法
EP0258967B2 (en)	1996-08-21	Process for producing optically active alcohols
JPH0246590B2 (cs)	1990-10-16
JP2502936B2 (ja)	1996-05-29	新規なアセチレン系誘導体
JP3254746B2 (ja)	2002-02-12	末端アセチレン化合物およびその製造法
JPH0250101B2 (cs)	1990-11-01
JP2782513B2 (ja)	1998-08-06	トリシクロ〔４．３．１．１ ▲上２▼’▲上５▼〕ウンデカ−７−エン及びその製造法
JP2736916B2 (ja)	1998-04-08	シベトンの製造法
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