CA1064526A - Procede pour la preparation d'-tetramethylphenylene-biscarbinols - Google Patents

Procede pour la preparation d'-tetramethylphenylene-biscarbinols

Info

Publication number: CA1064526A
Authority: CA; Canada
Prior art keywords: torr; temperature; biscarbinols; distilled; phenylene
Prior art date: 1975-01-29
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

CA244,293A

Other languages

English (en)

Other versions

CA244293S (en

Inventor

Hans-Josef Buysch

Jurgen Heuser

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1975-01-29

Filing date

1976-01-27

Publication date

1979-10-16

1976-01-27 Application filed by Bayer AG filed Critical Bayer AG

1979-10-16 Application granted granted Critical

1979-10-16 Publication of CA1064526A publication Critical patent/CA1064526A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims abstract description 11
239000003513 alkali Substances 0.000 claims abstract description 11
230000003647 oxidation Effects 0.000 claims abstract description 10
238000007254 oxidation reaction Methods 0.000 claims abstract description 10
239000011541 reaction mixture Substances 0.000 claims abstract description 8
238000004508 fractional distillation Methods 0.000 claims abstract description 4
238000005406 washing Methods 0.000 claims abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
239000001301 oxygen Substances 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 3
239000007864 aqueous solution Substances 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000004821 distillation Methods 0.000 description 9
150000001875 compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229920003987 resole Polymers 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 2
SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
208000005156 Dehydration Diseases 0.000 description 2
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
150000003938 benzyl alcohols Chemical group 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
230000006207 propylation Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229920003264 Maprenal® Polymers 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
241000193803 Therea Species 0.000 description 1
239000011717 all-trans-retinol Substances 0.000 description 1
235000019169 all-trans-retinol Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000009434 installation Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
230000000135 prohibitive effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
-1 tetramethyl-phenylene Chemical group 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation

Landscapes

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

CA244,293A 1975-01-29 1976-01-27 Procede pour la preparation d'-tetramethylphenylene-biscarbinols Expired CA1064526A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2503539A DE2503539C3 (de)	1975-01-29	1975-01-29	Verfahren zur Gewinnung von reinen a , a , a', a' -Tetramethylphenylenbiscarbinolen

Publications (1)

Publication Number	Publication Date
CA1064526A true CA1064526A (fr)	1979-10-16

Family

ID=5937557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA244,293A Expired CA1064526A (fr)	1975-01-29	1976-01-27	Procede pour la preparation d'-tetramethylphenylene-biscarbinols

Country Status (8)

Country	Link
JP (1)	JPS51100034A (fr)
BE (1)	BE837983A (fr)
CA (1)	CA1064526A (fr)
DE (1)	DE2503539C3 (fr)
FR (1)	FR2299299A1 (fr)
GB (1)	GB1479127A (fr)
IT (1)	IT1053541B (fr)
NL (1)	NL7600917A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP7493942B2 (ja) *	2020-01-10	2024-06-03	住友化学株式会社	ビス（２－ヒドロキシ－２－プロピル）ベンゼンの製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1491862A (fr) *	1965-09-08	1967-08-11	Bayer Ag	Procédé de préparation d'alpha, d'alpha, alpha', alpha'-tétraméthylxylylène dicarbinols

1975
- 1975-01-29 DE DE2503539A patent/DE2503539C3/de not_active Expired
1976
- 1976-01-27 CA CA244,293A patent/CA1064526A/fr not_active Expired
- 1976-01-27 JP JP51007196A patent/JPS51100034A/ja active Pending
- 1976-01-27 IT IT47808/76A patent/IT1053541B/it active
- 1976-01-27 GB GB3051/76A patent/GB1479127A/en not_active Expired
- 1976-01-28 BE BE163858A patent/BE837983A/fr unknown
- 1976-01-29 FR FR7602445A patent/FR2299299A1/fr active Granted
- 1976-01-29 NL NL7600917A patent/NL7600917A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
NL7600917A (nl)	1976-08-02
DE2503539B2 (de)	1980-01-17
DE2503539C3 (de)	1980-09-18
JPS51100034A (ja)	1976-09-03
BE837983A (fr)	1976-07-28
IT1053541B (it)	1981-10-10
FR2299299A1 (fr)	1976-08-27
DE2503539A1 (de)	1976-08-05
GB1479127A (en)	1977-07-06
FR2299299B1 (fr)	1979-07-20

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