CA1094099A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1094099A
Authority: CA; Canada
Prior art keywords: butadiene; gas; pressure; tower; fed
Prior art date: 1976-06-10
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

CA280,060A

Other languages

English (en)

Inventor

Yasuo Tanabe

Jun Toriya

Ikuo Kasahara

Tetsuo Shirao

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.)

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Industries Ltd

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.)

1976-06-10

Filing date

1977-06-07

Publication date

1981-01-20

1977-06-07 Application filed by Mitsubishi Chemical Industries Ltd filed Critical Mitsubishi Chemical Industries Ltd

1981-01-20 Application granted granted Critical

1981-01-20 Publication of CA1094099A publication Critical patent/CA1094099A/fr

Status Expired legal-status Critical Current

Links

MWWXARALRVYLAE-UHFFFAOYSA-N 2-acetyloxybut-3-enyl acetate Chemical compound CC(=O)OCC(C=C)OC(C)=O MWWXARALRVYLAE-UHFFFAOYSA-N 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 39
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 290
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 222
239000007789 gas Substances 0.000 claims abstract description 151
235000011054 acetic acid Nutrition 0.000 claims abstract description 78
238000010521 absorption reaction Methods 0.000 claims abstract description 74
238000006137 acetoxylation reaction Methods 0.000 claims abstract description 61
239000007788 liquid Substances 0.000 claims abstract description 58
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 32
239000001301 oxygen Substances 0.000 claims abstract description 32
229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
238000011084 recovery Methods 0.000 claims abstract description 32
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 23
238000000926 separation method Methods 0.000 claims abstract description 21
239000011541 reaction mixture Substances 0.000 claims abstract description 16
239000003054 catalyst Substances 0.000 claims abstract description 11
229910052763 palladium Inorganic materials 0.000 claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims abstract description 8
239000011261 inert gas Substances 0.000 claims abstract description 7
150000001243 acetic acids Chemical class 0.000 claims abstract 4
229960000583 acetic acid Drugs 0.000 description 62
238000004064 recycling Methods 0.000 description 10
239000002912 waste gas Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000007789 sealing Methods 0.000 description 7
230000006835 compression Effects 0.000 description 6
238000007906 compression Methods 0.000 description 6
238000004821 distillation Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VIRPYONDKXQHHU-UHFFFAOYSA-N 4-acetyloxybut-3-enyl acetate Chemical compound CC(=O)OCCC=COC(C)=O VIRPYONDKXQHHU-UHFFFAOYSA-N 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000007599 discharging Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
239000004480 active ingredient Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004880 explosion Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
229910052714 tellurium Inorganic materials 0.000 description 2
238000005406 washing Methods 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
229910001570 bauxite Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
-1 nitrogen or argon Chemical compound 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA280,060A 1976-06-10 1977-06-07 Traduction non-disponible Expired CA1094099A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP68097/1976		1976-06-10
JP6809776A JPS52151115A (en)	1976-06-10	1976-06-10	Preparation of diacetoxybutene

Publications (1)

Publication Number	Publication Date
CA1094099A true CA1094099A (fr)	1981-01-20

Family

ID=13363884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA280,060A Expired CA1094099A (fr)	1976-06-10	1977-06-07	Traduction non-disponible

Country Status (3)

Country	Link
JP (1)	JPS52151115A (fr)
CA (1)	CA1094099A (fr)
DE (1)	DE2726125A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5839141B2 (ja) *	1978-02-08	1983-08-27	ジェイエスアール株式会社	ジアセトキシブテンの製造方法
JPS57139038A (en) *	1981-02-23	1982-08-27	Mitsubishi Chem Ind Ltd	Preparation of diacetoxybutene
JP2530333B2 (ja) *	1987-04-23	1996-09-04	三菱化学株式会社	不飽和グリコ−ルジエステルの製造方法

1976
- 1976-06-10 JP JP6809776A patent/JPS52151115A/ja active Granted
1977
- 1977-06-07 CA CA280,060A patent/CA1094099A/fr not_active Expired
- 1977-06-10 DE DE19772726125 patent/DE2726125A1/de not_active Ceased

Also Published As

Publication number	Publication date
JPS52151115A (en)	1977-12-15
DE2726125A1 (de)	1977-12-22
JPS5542057B2 (fr)	1980-10-28

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

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US3068256A (en)	1962-12-11	Process for producing carboxylic acids
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JPH0572371B2 (fr)	1993-10-12
CN109701360B (zh)	2022-07-08	低碳烯烃与醋酸共氧化产品气中二氧化碳的脱除与利用装置与方法
CA1095928A (fr)	1981-02-17	Traduction non-disponible
JP2795360B2 (ja)	1998-09-10	炭酸ジメチルの連続的製法
US4152525A (en)	1979-05-01	Method of recovering butadiene gas from an acetoxylation process
US3725459A (en)	1973-04-03	Process for purifying adiponitrile
CA2072827A1 (fr)	1993-01-04	Procede de carboxylation continuelle d'acetylenes
US4228301A (en)	1980-10-14	Process for the preparation of diacetoxybutene
EP0057090B1 (fr)	1984-08-01	Procédé pour la préparation de monoxyde de carbone
JP2962454B2 (ja)	1999-10-12	炭酸ジメチルの連続製造法