NL193281C - Werkwijze voor het winnen van butaandiolen uit waterige oplossing. - Google Patents

Werkwijze voor het winnen van butaandiolen uit waterige oplossing. Download PDF

Info

Publication number: NL193281C
Authority: NL; Netherlands
Prior art keywords: steps; butanediol; nickel; hba; mpg
Prior art date: 1982-07-07

Application number

NL8302428A

Other languages

English (en)

Dutch (nl)

Other versions

NL8302428A (nl

NL193281B (nl

Original Assignee

Kuraray Co

Daicel Chem

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.)

1982-07-07

Filing date

1983-07-07

Publication date

1999-05-06

1983-07-07 Application filed by Kuraray Co, Daicel Chem filed Critical Kuraray Co

1984-02-01 Publication of NL8302428A publication Critical patent/NL8302428A/nl

1999-01-04 Publication of NL193281B publication Critical patent/NL193281B/xx

1999-05-06 Application granted granted Critical

1999-05-06 Publication of NL193281C publication Critical patent/NL193281C/nl

Links

CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 title claims abstract description 31
238000000034 method Methods 0.000 title claims abstract description 28
239000007864 aqueous solution Substances 0.000 title claims abstract description 23
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 100
PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 claims abstract description 55
238000009835 boiling Methods 0.000 claims abstract description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
238000004821 distillation Methods 0.000 claims abstract description 30
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 24
239000000203 mixture Substances 0.000 claims abstract description 24
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims abstract description 21
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 18
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 12
239000002244 precipitate Substances 0.000 claims abstract description 9
229910052759 nickel Inorganic materials 0.000 claims description 49
239000007788 liquid Substances 0.000 claims description 42
239000000047 product Substances 0.000 claims description 17
238000000926 separation method Methods 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 11
238000010438 heat treatment Methods 0.000 claims description 11
239000012535 impurity Substances 0.000 claims description 11
239000000243 solution Substances 0.000 claims description 9
239000006227 byproduct Substances 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
238000011084 recovery Methods 0.000 claims description 8
238000007037 hydroformylation reaction Methods 0.000 claims description 7
238000004508 fractional distillation Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000006286 aqueous extract Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000010409 thin film Substances 0.000 claims description 3
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
239000012430 organic reaction media Substances 0.000 claims description 2
238000001704 evaporation Methods 0.000 description 16
230000000052 comparative effect Effects 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 6
238000012545 processing Methods 0.000 description 6
238000010626 work up procedure Methods 0.000 description 6
239000000470 constituent Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
UIKQNMXWCYQNCS-UHFFFAOYSA-N 2-hydroxybutanal Chemical compound CCC(O)C=O UIKQNMXWCYQNCS-UHFFFAOYSA-N 0.000 description 1
QUQPOXQBSBPDMV-UHFFFAOYSA-N 2-methyl-3-(oxolan-2-yloxy)propan-1-ol Chemical compound OCC(C)COC1CCCO1 QUQPOXQBSBPDMV-UHFFFAOYSA-N 0.000 description 1
NMPJHMFXHISVBR-UHFFFAOYSA-N 4-(oxolan-2-yloxy)butan-1-ol Chemical compound OCCCCOC1CCCO1 NMPJHMFXHISVBR-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000010408 film Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
229910001453 nickel ion Inorganic materials 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002407 reforming Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8302428A 1982-07-07 1983-07-07 Werkwijze voor het winnen van butaandiolen uit waterige oplossing. NL193281C (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP57117945A JPS5910537A (ja)	1982-07-07	1982-07-07	ブタンジオ−ルの取得法
JP11794582		1982-07-07

Publications (3)

Publication Number	Publication Date
NL8302428A NL8302428A (nl)	1984-02-01
NL193281B NL193281B (nl)	1999-01-04
NL193281C true NL193281C (nl)	1999-05-06

Family

ID=14724113

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8302428A NL193281C (nl)	1982-07-07	1983-07-07	Werkwijze voor het winnen van butaandiolen uit waterige oplossing.

Country Status (3)

Country	Link
US (1)	US4465873A (fr)
JP (1)	JPS5910537A (fr)
NL (1)	NL193281C (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102826969B (zh) *	2011-06-17	2015-07-22	中国石油化工股份有限公司	一种烯烃氢甲酰化反应液相排出物的分离方法
WO2013005748A1 (fr) *	2011-07-04	2013-01-10	三菱化学株式会社	Procédé pour produire du 1,4-butanediol
WO2015034948A1 (fr)	2013-09-03	2015-03-12	Myriant Corporation	Procédé de fabrication d'acide acrylique, d'acrylonitrile et de 1,4-butanediol à partir de 1,3-propanediol
CN115500751A (zh) *	2022-09-20	2022-12-23	深圳市杉川机器人有限公司	基站的控制方法和具有其的基站

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4064145A (en) *	1975-10-20	1977-12-20	Celanese Corporation	Production of tetrahydrofuran
US4083882A (en) *	1976-08-26	1978-04-11	Celanese Corporation	Production of 1,4-butanediol
DE2728407A1 (de) *	1977-06-24	1979-01-04	Basf Ag	Verfahren zur behandlung von butandiol, das als kondensat bei der herstellung von polybutylenterephthalaten erhalten wurde
US4200501A (en) *	1978-03-24	1980-04-29	Basf Wyandotte Corporation	Silicate fouling control during dihydric alcohol distillation
DE2842942A1 (de) *	1978-10-02	1980-04-17	Basf Ag	Verfahren zur herstellung von 2-methylpentandiol-(2,4)
JPS55151521A (en) *	1979-05-15	1980-11-26	Toyo Soda Mfg Co Ltd	Preparation of alcohol

1982
- 1982-07-07 JP JP57117945A patent/JPS5910537A/ja active Granted
1983
- 1983-07-06 US US06/511,419 patent/US4465873A/en not_active Expired - Lifetime
- 1983-07-07 NL NL8302428A patent/NL193281C/nl not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH038326B2 (fr)	1991-02-05
JPS5910537A (ja)	1984-01-20
NL8302428A (nl)	1984-02-01
NL193281B (nl)	1999-01-04
US4465873A (en)	1984-08-14

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1990-08-01	BA	A request for search or an international-type search has been filed
1991-03-01	BB	A search report has been drawn up
1991-07-01	BC	A request for examination has been filed
2003-09-01	V4	Lapsed because of reaching the maximum lifetime of a patent	Effective date: 20030707

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