JPS6230971B2 - - Google Patents

Info

Publication number: JPS6230971B2
Authority: JP; Japan
Prior art keywords: reaction; selectivity; catalyst; citronellal; geraniol
Prior art date: 1979-12-12
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

Application number

JP54161272A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5683434A (en

Inventor

Shuji Tsucha

Hideo Suzuki

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.)

Nissan Chemical Corp

Original Assignee

Nissan Chemical 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.)

1979-12-12

Filing date

1979-12-12

Publication date

1987-07-06

1979-12-12 Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp

1979-12-12 Priority to JP16127279A priority Critical patent/JPS5683434A/ja

1981-07-08 Publication of JPS5683434A publication Critical patent/JPS5683434A/ja

1987-07-06 Publication of JPS6230971B2 publication Critical patent/JPS6230971B2/ja

Status Granted legal-status Critical Current

Links

238000006243 chemical reaction Methods 0.000 claims description 25
239000003054 catalyst Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 8
239000003999 initiator Substances 0.000 claims description 5
239000011261 inert gas Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 34
NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 18
150000001299 aldehydes Chemical class 0.000 description 11
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
229930003633 citronellal Natural products 0.000 description 9
235000000983 citronellal Nutrition 0.000 description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 8
239000005792 Geraniol Substances 0.000 description 8
GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 8
229940113087 geraniol Drugs 0.000 description 8
239000000203 mixture Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000002994 raw material Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
-1 aromatic mercaptans Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000006317 isomerization reaction Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
CRDAMVZIKSXKFV-YFVJMOTDSA-N (2-trans,6-trans)-farnesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO CRDAMVZIKSXKFV-YFVJMOTDSA-N 0.000 description 1
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
BOTWFXYSPFMFNR-HMMYKYKNSA-N (e)-3,7,11,15-tetramethylhexadec-2-en-1-ol Chemical compound CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-HMMYKYKNSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical compound SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 description 1
ITBYWGRSPHMAEE-UHFFFAOYSA-N 3,7,11-trimethyldodeca-6,10-dienal Chemical compound O=CCC(C)CCC=C(C)CCC=C(C)C ITBYWGRSPHMAEE-UHFFFAOYSA-N 0.000 description 1
229930008411 3,7-dimethylocta-2,6-dien-1-ol Natural products 0.000 description 1
YNWSTXBQNLCEPJ-UHFFFAOYSA-N 3-decyl-3h-dithiole Chemical compound CCCCCCCCCCC1SSC=C1 YNWSTXBQNLCEPJ-UHFFFAOYSA-N 0.000 description 1
WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
229910017518 Cu Zn Inorganic materials 0.000 description 1
229910017752 Cu-Zn Inorganic materials 0.000 description 1
229910017813 Cu—Cr Inorganic materials 0.000 description 1
229910017943 Cu—Zn Inorganic materials 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
229940043350 citral Drugs 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
239000001307 helium Substances 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
230000000366 juvenile effect Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000003012 phosphoric acid amides Chemical class 0.000 description 1
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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

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

JP16127279A 1979-12-12 1979-12-12 Preparation of aldehyde Granted JPS5683434A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16127279A JPS5683434A (en)	1979-12-12	1979-12-12	Preparation of aldehyde

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16127279A JPS5683434A (en)	1979-12-12	1979-12-12	Preparation of aldehyde

Publications (2)

Publication Number	Publication Date
JPS5683434A JPS5683434A (en)	1981-07-08
JPS6230971B2 true JPS6230971B2 (cs)	1987-07-06

Family

ID=15731944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16127279A Granted JPS5683434A (en)	1979-12-12	1979-12-12	Preparation of aldehyde

Country Status (1)

Country	Link
JP (1)	JPS5683434A (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10029969B2 (en)	2013-03-06	2018-07-24	Takasago International Corporation	Method of producing optically-active aldehyde

1979
- 1979-12-12 JP JP16127279A patent/JPS5683434A/ja active Granted

Also Published As

Publication number	Publication date
JPS5683434A (en)	1981-07-08

Publication	Publication Date	Title
Wallace et al.	1965	The base-catalysed oxidation of aliphatic and aromatic thiols and disulphides to sulphonic acids
Suzuki et al.	1982	Bis (trimethylsilyl) peroxide for the Baeyer-Villiger type oxidation
JPS6215536B2 (cs)	1987-04-08
JPS63104953A (ja)	1988-05-10	２，６−ジ第三ブチル−４−メルカプトフェノールの製法
US3960966A (en)	1976-06-01	Ketoisophorone manufacture
JPS6230971B2 (cs)	1987-07-06
KR20010078767A (ko)	2001-08-21	촉매 제조방법 및 이들을 사용한 촉매 산화 공정
US5274145A (en)	1993-12-28	α-hydroxy-acids, preparation process and the use thereof
EP0005452B1 (de)	1980-10-01	Acyloxy-2-butene, ihre Herstellung und ihre Verwendung zur Herstellung von 4-Acetoxytiglinaldehyd
Aizpurua et al.	1984	Reagents and synthetic methods. 31. Silylations with N-trimethylsilyl-2-oxazolidinone (TMSO)
KR870001316B1 (ko)	1987-07-13	올레핀산 및 에스테르의 제조방법
US4124633A (en)	1978-11-07	Tellurium catalyzed decomposition of peroxide intermediates resulting from the autoxidation of unsaturated aldehydes
JPS6230970B2 (cs)	1987-07-06
US3654354A (en)	1972-04-04	Process for the oxidation of unsaturated hydrocarbons
EP0475801B1 (fr)	1994-11-09	Procédé de fabrication du thiophène
US4049706A (en)	1977-09-20	Selective oxidation of chrysanthemyl alcohol
US4700004A (en)	1987-10-13	Conversion of mercaptans to disulfides with soluble cobalt catalyst system
CA1128955A (fr)	1982-08-03	Procede pour la preparation d'esters
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EP0024770B1 (en)	1983-11-09	Hydrolysis of allyl ethers and ketones thus prepared
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US5981792A (en)	1999-11-09	Process for the production of 1-functional allylalcohol carboxylic esters
EP0291033A1 (en)	1988-11-17	Preparation of 4-pentenoates by isomerization
Hirano et al.	1998	Synthesis of disulfides by the oxidative coupling of thiols with calcium hypochlorite and silica gel in hexane