NL1007829C2 - Werkwijze voor de bereiding van benzylalcohol. - Google Patents

Werkwijze voor de bereiding van benzylalcohol. Download PDF

Info

Publication number: NL1007829C2
Authority: NL; Netherlands
Prior art keywords: benzyl; hydrolysis; process according; acid; benzyl alcohol
Prior art date: 1997-12-18

Application number

NL1007829A

Other languages

English (en)

Dutch (nl)

Inventor

Christiaan Johanne Stoelwinder

Hendricus Johannes Rozie

Jacob Van Soolingen

Alexander Peter Marie Vrinzen

Abram Peet

Otto Gerrit Plantema

Original Assignee

Dsm Nv

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.)

1997-12-18

Filing date

1997-12-18

Publication date

1999-06-21

1997-12-18 Application filed by Dsm Nv filed Critical Dsm Nv

1997-12-18 Priority to NL1007829A priority Critical patent/NL1007829C2/nl

1998-12-14 Priority to EP98204221A priority patent/EP0924179A1/en

1998-12-17 Priority to CN98126533A priority patent/CN1116263C/zh

1998-12-17 Priority to EE9800361A priority patent/EE03822B1/et

1998-12-18 Priority to JP10360114A priority patent/JPH11246452A/ja

1998-12-18 Priority to US09/215,244 priority patent/US6326521B2/en

1999-06-21 Application granted granted Critical

1999-06-21 Publication of NL1007829C2 publication Critical patent/NL1007829C2/nl

Links

WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title claims abstract description 79
238000000034 method Methods 0.000 title claims abstract description 32
235000019445 benzyl alcohol Nutrition 0.000 title claims abstract description 27
238000002360 preparation method Methods 0.000 title claims abstract description 6
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims abstract description 44
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 29
229960002903 benzyl benzoate Drugs 0.000 claims abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
239000002253 acid Substances 0.000 claims abstract description 20
230000007062 hydrolysis Effects 0.000 claims abstract description 19
-1 benzyl ester Chemical class 0.000 claims abstract description 15
239000011541 reaction mixture Substances 0.000 claims abstract description 15
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims abstract description 14
239000007791 liquid phase Substances 0.000 claims abstract description 12
239000008346 aqueous phase Substances 0.000 claims abstract description 7
229940007550 benzyl acetate Drugs 0.000 claims abstract description 7
239000012074 organic phase Substances 0.000 claims abstract description 7
QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 claims abstract description 5
238000005191 phase separation Methods 0.000 claims abstract description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 23
239000005711 Benzoic acid Substances 0.000 claims description 22
235000010233 benzoic acid Nutrition 0.000 claims description 22
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 18
UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
238000000605 extraction Methods 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
235000011054 acetic acid Nutrition 0.000 claims description 2
238000004821 distillation Methods 0.000 claims description 2
235000019253 formic acid Nutrition 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
238000009835 boiling Methods 0.000 description 8
239000011269 tar Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000003780 insertion Methods 0.000 description 3
230000037431 insertion Effects 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
239000011273 tar residue Substances 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
GTKWHQWJTVWORA-UHFFFAOYSA-N (2-benzylphenyl)methanol Chemical compound OCC1=CC=CC=C1CC1=CC=CC=C1 GTKWHQWJTVWORA-UHFFFAOYSA-N 0.000 description 1
ISKVDROBICOSMM-UHFFFAOYSA-N (3-benzylphenyl)methanol Chemical compound OCC1=CC=CC(CC=2C=CC=CC=2)=C1 ISKVDROBICOSMM-UHFFFAOYSA-N 0.000 description 1
MHZOFWFRCQRXIH-UHFFFAOYSA-N (4-benzylphenyl)methanol Chemical compound C1=CC(CO)=CC=C1CC1=CC=CC=C1 MHZOFWFRCQRXIH-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
MIYKHJXFICMPOJ-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine Chemical compound C=1C=CC=CC=1CN=CC1=CC=CC=C1 MIYKHJXFICMPOJ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids

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)

NL1007829A 1997-12-18 1997-12-18 Werkwijze voor de bereiding van benzylalcohol. NL1007829C2 (nl)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
NL1007829A NL1007829C2 (nl)	1997-12-18	1997-12-18	Werkwijze voor de bereiding van benzylalcohol.
EP98204221A EP0924179A1 (en)	1997-12-18	1998-12-14	Process for the preparation of benzyl alcohol
CN98126533A CN1116263C (zh)	1997-12-18	1998-12-17	苯甲醇的制备方法
EE9800361A EE03822B1 (et)	1997-12-18	1998-12-17	Meetod bensüülalkoholi valmistamiseks
JP10360114A JPH11246452A (ja)	1997-12-18	1998-12-18	ベンジルアルコ―ルの製造法
US09/215,244 US6326521B2 (en)	1997-12-18	1998-12-18	Process for the preparation of benzyl alcohol

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
NL1007829		1997-12-18
NL1007829A NL1007829C2 (nl)	1997-12-18	1997-12-18	Werkwijze voor de bereiding van benzylalcohol.
US21524498		1998-12-18
US09/215,244 US6326521B2 (en)	1997-12-18	1998-12-18	Process for the preparation of benzyl alcohol

Publications (1)

Publication Number	Publication Date
NL1007829C2 true NL1007829C2 (nl)	1999-06-21

Family

ID=26642715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1007829A NL1007829C2 (nl)	1997-12-18	1997-12-18	Werkwijze voor de bereiding van benzylalcohol.

Country Status (6)

Country	Link
US (1)	US6326521B2 (et)
EP (1)	EP0924179A1 (et)
JP (1)	JPH11246452A (et)
CN (1)	CN1116263C (et)
EE (1)	EE03822B1 (et)
NL (1)	NL1007829C2 (et)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10218243A1 (de) *	2002-04-24	2003-11-06	Bayer Ag	Verfahren zur Herstellung von Benzylalkoholen
JP4406301B2 (ja) *	2004-02-13	2010-01-27	トヨタ自動車株式会社	１級アミンの製造方法
US7851551B2 (en) *	2004-03-25	2010-12-14	Xerox Corporation	Polymer processes
CN101811936B (zh) *	2009-11-12	2013-11-06	山东聊城中盛蓝瑞化工有限公司	一种苯甲醇连续水解工艺及其使用的设备
CN104368385A (zh) *	2014-10-11	2015-02-25	江苏常州酞青新材料科技有限公司	一种醋酸苄酯的水解催化剂制备方法
CN206204081U (zh) *	2016-02-24	2017-05-31	湖北绿色家园材料技术股份有限公司	一种苯甲醇生产废水综合利用的循环生产装置
CN108130188A (zh) *	2018-01-12	2018-06-08	潜江新亿宏有机化工有限公司	一种香料乙酸苄酯的精制方法
CN110903162B (zh) *	2018-09-15	2022-09-02	天津大加化工有限公司	一种苯甲醇的生产工艺

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4088823A (en) *	1975-10-07	1978-05-09	Phillips Petroleum Company	Promoted liquid phase oxidation of alkyl aromatic compounds
NL7903876A (nl) *	1979-05-17	1980-11-19	Stamicarbon	Werkwijze voor het bereiden van een zuiver alkali- metaalbenzoaat naast benzylalcohol.
SU960159A1 (ru) *	1979-11-22	1982-09-23	Предприятие П/Я А-7815	Способ получени бензилацетата и/или бензилового спирта
EP0778257A2 (en) *	1995-12-04	1997-06-11	Tosoh Corporation	Process for producing benzyl acetate and benzyl alcohol

Family Cites Families (7)

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Publication number	Priority date	Publication date	Assignee	Title
NL7614458A (nl) *	1976-12-28	1978-06-30	Stamicarbon	Werkwijze voor het verwerken van een benzylbenzoaatbevattende teer.
PT67457B (en) *	1976-12-28	1979-05-25	Stamicarbon	Process for preparing oxidation products of monoalkyl benzene compounds
FR2413348A1 (fr) *	1977-12-31	1979-07-27	Dynamit Nobel Ag	Procede pour l'obtention d'alcools benzyliques
NL7805415A (nl) *	1978-05-19	1979-11-21	Stamicarbon	Werkwijze voor het bereiden van een alkalimetaalbenzoaat naast een benzylalkohol.
US4250344A (en) *	1978-10-25	1981-02-10	Chem Systems Inc.	Cracking process for styrene
US4281178A (en) *	1979-12-03	1981-07-28	Tenneco Chemicals, Inc.	Process for the production of benzoic acid from process residues that contain benzyl benzoate
CA2025044C (en) *	1989-09-22	1999-12-21	Michael Siskin	Process for converting and upgrading organic resource materials in aqueous environments

1997
- 1997-12-18 NL NL1007829A patent/NL1007829C2/nl not_active IP Right Cessation
1998
- 1998-12-14 EP EP98204221A patent/EP0924179A1/en not_active Withdrawn
- 1998-12-17 EE EE9800361A patent/EE03822B1/et not_active IP Right Cessation
- 1998-12-17 CN CN98126533A patent/CN1116263C/zh not_active Expired - Fee Related
- 1998-12-18 JP JP10360114A patent/JPH11246452A/ja active Pending
- 1998-12-18 US US09/215,244 patent/US6326521B2/en not_active Expired - Fee Related

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4088823A (en) *	1975-10-07	1978-05-09	Phillips Petroleum Company	Promoted liquid phase oxidation of alkyl aromatic compounds
NL7903876A (nl) *	1979-05-17	1980-11-19	Stamicarbon	Werkwijze voor het bereiden van een zuiver alkali- metaalbenzoaat naast benzylalcohol.
SU960159A1 (ru) *	1979-11-22	1982-09-23	Предприятие П/Я А-7815	Способ получени бензилацетата и/или бензилового спирта
EP0778257A2 (en) *	1995-12-04	1997-06-11	Tosoh Corporation	Process for producing benzyl acetate and benzyl alcohol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 98, no. 9, 28 February 1983, Columbus, Ohio, US; abstract no. 71662b, page 589; XP002073594 *

Also Published As

Publication number	Publication date
EE03822B1 (et)	2002-08-15
JPH11246452A (ja)	1999-09-14
US20010014762A1 (en)	2001-08-16
CN1116263C (zh)	2003-07-30
EP0924179A1 (en)	1999-06-23
EE9800361A (et)	1999-08-16
US6326521B2 (en)	2001-12-04
CN1227213A (zh)	1999-09-01

Legal Events

Date	Code	Title	Description
1999-08-02	PD2B	A search report has been drawn up
2002-09-02	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20020701

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