CA1097676A - Manufacture of n-alkylcarbamates - Google Patents

Manufacture of n-alkylcarbamates

Info

Publication number: CA1097676A
Authority: CA; Canada
Prior art keywords: reaction; formula; alkyl; chloride; naphthyl
Prior art date: 1977-01-21
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

CA293,294A

Other languages

English (en)

French (fr)

Inventor

Christian Reitel

Karl-Heinz Koenig

Dietrich Mangold

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.)

BASF SE

Original Assignee

BASF SE

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.)

1977-01-21

Filing date

1977-12-16

Publication date

1981-03-17

1977-12-16 Application filed by BASF SE filed Critical BASF SE

1981-03-17 Application granted granted Critical

1981-03-17 Publication of CA1097676A publication Critical patent/CA1097676A/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 17
239000002904 solvent Substances 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
238000002844 melting Methods 0.000 claims abstract description 7
230000008018 melting Effects 0.000 claims abstract description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 6
239000007788 liquid Substances 0.000 claims abstract description 5
-1 carbamyl chlorides Chemical class 0.000 claims description 15
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000011261 inert gas Substances 0.000 claims description 4
239000000155 melt Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 abstract 1
CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 6
LPCJHUPMQKSPDC-UHFFFAOYSA-N 3,5-diethylphenol Chemical compound CCC1=CC(O)=CC(CC)=C1 LPCJHUPMQKSPDC-UHFFFAOYSA-N 0.000 description 6
229940054025 carbamate anxiolytics Drugs 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 4
150000004780 naphthols Chemical class 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
HUNDISMVCBSIKO-UHFFFAOYSA-N (3,5-diethylphenyl) n-methylcarbamate Chemical compound CCC1=CC(CC)=CC(OC(=O)NC)=C1 HUNDISMVCBSIKO-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
150000007824 aliphatic compounds Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
JGFZITGNFAVSKU-UHFFFAOYSA-N 3,5-dimethyl-4-(methylsulfanyl)phenol Chemical compound CSC1=C(C)C=C(O)C=C1C JGFZITGNFAVSKU-UHFFFAOYSA-N 0.000 description 1
ZDWSNKPLZUXBPE-UHFFFAOYSA-N 3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1 ZDWSNKPLZUXBPE-UHFFFAOYSA-N 0.000 description 1
ZDUIHRJGDMTBEX-UHFFFAOYSA-N 3-methyl-5-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC(O)=C1 ZDUIHRJGDMTBEX-UHFFFAOYSA-N 0.000 description 1
SZBIKNXBDIVHKY-UHFFFAOYSA-N 4-(dimethylamino)-3-methylphenol Chemical compound CN(C)C1=CC=C(O)C=C1C SZBIKNXBDIVHKY-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
229960001867 guaiacol Drugs 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical class CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids

Landscapes

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

CA293,294A 1977-01-21 1977-12-16 Manufacture of n-alkylcarbamates Expired CA1097676A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772702372 DE2702372A1 (de)	1977-01-21	1977-01-21	Verfahren zur herstellung von n-alkylcarbamaten
DEP2702372.9		1977-01-21

Publications (1)

Publication Number	Publication Date
CA1097676A true CA1097676A (en)	1981-03-17

Family

ID=5999198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,294A Expired CA1097676A (en)	1977-01-21	1977-12-16	Manufacture of n-alkylcarbamates

Country Status (13)

Country	Link
JP (1)	JPS5392714A (de)
BE (1)	BE863017A (de)
CA (1)	CA1097676A (de)
DD (1)	DD133793A5 (de)
DE (1)	DE2702372A1 (de)
FR (1)	FR2378002A1 (de)
GB (1)	GB1594422A (de)
HU (1)	HU175440B (de)
IL (1)	IL53600A0 (de)
IT (1)	IT1103262B (de)
NL (1)	NL7800740A (de)
SU (1)	SU860694A1 (de)
ZA (1)	ZA78364B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6294502B1 (en)	1998-05-22	2001-09-25	Bayer Aktiengesellschaft	Thermally-responsive record material
US6015771A (en) *	1998-05-22	2000-01-18	Bayer Aktiengesellschaft	Thermally-responsive record material

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB191325971A (en) *	1913-11-12	1914-03-05	Bruno Beckmann Chem Fab G M B	Improved Manufacture of Carbamic Acid Ester of alpha-dichlorhydrin.
CH383945A (de) *	1960-04-14	1964-11-15	Geigy Ag J R	Verfahren zur Herstellung von neuen Arylcarbamaten und deren Verwendung zur Insektenbekämpfung
GB1054673A (de) *	1962-08-23
GB1042203A (en) *	1963-04-09	1966-09-14	Robert J Geary	Substituted phenyl carbamates and their use as plant growth regulants

1977
- 1977-01-21 DE DE19772702372 patent/DE2702372A1/de not_active Withdrawn
- 1977-12-13 IL IL53600A patent/IL53600A0/xx unknown
- 1977-12-16 CA CA293,294A patent/CA1097676A/en not_active Expired
1978
- 1978-01-09 JP JP60578A patent/JPS5392714A/ja active Pending
- 1978-01-16 SU SU782566402A patent/SU860694A1/ru active
- 1978-01-18 IT IT47692/78A patent/IT1103262B/it active
- 1978-01-18 BE BE184400A patent/BE863017A/xx unknown
- 1978-01-19 DD DD7800203306A patent/DD133793A5/de unknown
- 1978-01-20 HU HU78BA3617A patent/HU175440B/hu unknown
- 1978-01-20 FR FR7801658A patent/FR2378002A1/fr not_active Withdrawn
- 1978-01-20 NL NL7800740A patent/NL7800740A/xx not_active Application Discontinuation
- 1978-01-20 ZA ZA00780364A patent/ZA78364B/xx unknown
- 1978-01-20 GB GB2348/78A patent/GB1594422A/en not_active Expired

Also Published As

Publication number	Publication date
ZA78364B (en)	1979-01-31
IL53600A0 (en)	1978-03-10
NL7800740A (nl)	1978-07-25
FR2378002A1 (fr)	1978-08-18
IT1103262B (it)	1985-10-14
SU860694A1 (ru)	1981-08-30
HU175440B (hu)	1980-08-28
DD133793A5 (de)	1979-01-24
GB1594422A (en)	1981-07-30
JPS5392714A (en)	1978-08-15
BE863017A (fr)	1978-07-18
IT7847692A0 (it)	1978-01-18
DE2702372A1 (de)	1978-07-27

Legal Events

Date	Code	Title	Description
1998-03-17	MKEX	Expiry

Publication	Publication Date	Title
CA1058203A (en)	1979-07-10	Process for the preparation of aromatic carbonates
GB2091730A (en)	1982-08-04	Preparation of aromatic urethanes
US4501915A (en)	1985-02-26	Preparation of N-alkyl-monosubstituted carbamates
US4381403A (en)	1983-04-26	Process for the preparation of N-monosubstituted carbamic acid esters
US3311655A (en)	1967-03-28	Process for the preparation of urethanes
HU185896B (en)	1985-04-28	New process for producing 7-hydroxy-2,2-dimethyl-2,3-dihydro-bracket-benzo-furane-bracket closed
CA1097676A (en)	1981-03-17	Manufacture of n-alkylcarbamates
US4384115A (en)	1983-05-17	Process for preparing tetrahydro-1,3-oxazin-2-ones
JP2569351B2 (ja)	1997-01-08	芳香族カーボネート化合物を製造する方法
Gaylord et al.	1953	The reactions of carbamates with alcohols
EP0403528B1 (de)	1993-02-10	Verfahren zur herstellung von alkyl-3-alcoxypropionaten
US3819683A (en)	1974-06-25	N-acyl carbamate production
JPS6113466B2 (de)	1986-04-14
US5326899A (en)	1994-07-05	Process for preparation of iodopropargyl carbamates
US3937738A (en)	1976-02-10	(perhaloalkyl) thio-substituted aldehydes and ketones
US4613683A (en)	1986-09-23	Preparation of alkyl gallates
FR2481699A1 (fr)	1981-11-06	Preparation de carbamates n-monosubstitues
US4272441A (en)	1981-06-09	Preparation of carbamates
US5457238A (en)	1995-10-10	Process for the preparation of fluoroketones
US4095034A (en)	1978-06-13	Manufacture of α-naphthyl-N-methyl-carbamate
EP0496347B1 (de)	1996-09-04	Verfahren zur Herstellung von Fluorbenzolderivaten und verwandter Verbindungen
US4541960A (en)	1985-09-17	Method for preparing cyanacetaldehyde acetals
ES8206461A1 (es)	1982-09-01	Procedimiento de fabricacion de tiocloroformiatos mediante accion del fosgeno sobre un mercaptan en presencia de un catalizador .
EP0203827B1 (de)	1989-04-05	Verfahren zur Herstellung von ortho-Alkylthiophenolen
EP0163533B1 (de)	1988-05-25	Herstellung von Additionsprodukten von Alkoholen, Ethern und Estern mit 1,2-Dichlordifluoräthylen